Exploring the world’s greatest startup stories.
Get a behind the scenes look into the founding stories of your favorite companies. Learn how the industries they operate in actually work, and learn playbooks and tactics you can use to launch and scale your own business.
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Benchmark’s Eric Vishria on Going Zero to $100M ARR in 12 Months, Archetypes of Top AI Founders, Why Storytelling is a Superpower, How Benchmark Makes New Investments
Eric Vishria is a General Partner at Benchmark Capital.
Our conversation goes inside the new class of startups going zero to $100 million ARR in 12 months, the ways AI is changing company building, and how Eric and Benchmark make new investments.
We get into the risk rewards of Series As today, how Benchmark competes to work with founders, and and why the best storytellers win.
We also talk about parallels between the 90’s, 2000’s, and today, and how the archetype of successful founders has changed in the age of AI.
Thanks to Spenser Skates, Sajith Wickramasekara, Bobby DeSimone, and Semil Shah for help brainstorming topics for Eric!
Special thanks to this episode’s sponsors:
- Bolt: Help them break a world record for the largest hackathon - up to $1m in prizes. Sign-up here.
- Numeral: The end-to-end platform for sales tax and compliance. Try it here.
Timestamps:
(5:17) What gets Eric excited about a new investment
(7:48) Backing learning machines
(12:34) Backing Cerebras at inception
(16:20) Why the best storytellers win
(21:17) How Eric works with founders
(26:38) Companies going zero to $100m in 12 months
(31:09) Revenue quality of AI products
(32:41) Moats and business models in AI
(38:41) AI margins and runway
(41:14) Parallels between winners of the 90’s and today
(44:54) Archetypes of the best AI founders
(50:43) SaaS companies successfully pivoting to AI
(53:43) LLMs are most comparable to transistors in the 1950s
(56:19) Ways Eric uses AI personally
(58:05) How VC has changed over the past decade
(1:01:40) VC is a hustler’s business
(1:03:20) Backing extraordinary companies is all that matters
(1:09:36) What makes Benchmark unique
(1:17:03) How Benchmark makes investment decisions
(1:18:38) Skipping senior year of high school
(1:20:21) Working with Ben Horowitz and Marc Andreessen ‘00-’08
(1:24:42) Starting RockMelt, selling to Yahoo
(1:26:28) Joining Benchmark in 2014
(1:28:08) Investing in Confluent one month later
(1:28:50) Lessons from Spenser at Amplitude
(1:29:36) Fireworks AI’s hyper growth
(1:30:49) Pricing in AI changing from tokens to outcomes
(1:32:23) Ways Eric’s perception of VCs changed after becoming one
(1:34:07) How to build a management team
(1:38:21 )The best CEOs make new mistakes
(1:39:50) Why there should be more public companies
(1:44:03) “Even great companies can be overvalued”
Referenced
Ben Thompson + Mark Zuckerberg Interview
Andy Price at Artisinal Talent
Follow Eric
Follow Turner
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Samsara’s Journey to $26B Public Company | Sanjit Biswas, Co-founder and CEO
Sanjit Biswas is the Co-founder and CEO of Samsara, the fleet management and safety platform.
At the time of publication, Samsara is a public company worth over $26 billion, and we unpack how exactly they went from zero to run rating at over $1.5 billion in revenue in ten years.
We get into using AI to impact the physical world, how Samsara uses AI internally, and how their products prevent over 200,000 deaths per year.
Sanjit has built two unicorns, and he shares everything he’s learned along the way, including what most founders and investors get wrong about hardware, thinking customer-first instead of product-first, how to know when you have product market fit, mastering sales as a technical founder, and how to spend more time with your customers.
We also talk about getting his high school online in the 90’s, and the research project that turned into Sanjit’s first company, Meraki, and its $1.2 billion dollar sale to Cisco in 2012.
Thanks to Bolt for supporting this episode. Help them break a world record for the largest hackathon (up to $1m in prizes): https://bit.ly/ThePeelBoltHackathon
Timestamps:
(4:26) Samsara: Helping the world of physical operations
(8:44) Preventing 200,000 deaths per year
(11:19) AI opportunities in transportation
(14:43) Samsara’s internal AI tools
(16:58) What people get wrong when building hardware
(19:04) Starting Samsara customer-first instead of product-first
(22:23) Find adjacent products for your customers
(26:28) How to know you have product market fit
(34:52) How to spend more time with customers and build feedback loops
(43:00) 70-20-10 framework for allocating capital
(45:07) Importance of selling new products to existing customers
(49:15) Revisiting the product roadmap based on new technology
(50:38) Why Sanjit credits focus to hitting $1B revenue in nine years
(53:41) Learning to love sales as a technical founder
(57:06) Getting his high school online in the 90’s
(1:01:46) The research project that turned into Sanjit’s first company, Meraki
(1:04:01) Importance of asymmetric risk when starting a company
(1:05:41) Early days of Meraki taking off
(1:09:19) Surviving and doubling during the financial crisis
(1:16:00) Cisco acquiring Meraki for $1.2B
(1:18:15) Meraki’s post-acquisition integration
(1:20:48) Differences between 1st and 2nd company
(1:24:19) Almost starting an renewable energy company
(1:25:52) The power of small teams
(1:28:49) One-shotting Bill Gates’ biography at 10-years old
Referenced
Samsara: https://samsara.com/
Meraki: https://meraki.cisco.com/
Arduino: https://www.arduino.cc/
Raspberry Pi: https://www.raspberrypi.com/
Hard Drive: Bill Gates and the Making of the Microsoft Empire: https://www.amazon.com/Hard-Drive-Making-Microsoft-Empire/dp/0887306292
No Priors Podcast: https://www.youtube.com/@NoPriorsPodcast
Follow Sanjit
LinkedIn: https://www.linkedin.com/in/sanjitbiswas/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Michael Kim @ Cendana | Lessons from the Top VCs, How Cendana Does Diligence, Portfolio Construction Best Practices, the 60x Rule, How Seed Funds Compete vs Multi-stage, Inside Cendana's Early Days
Michael Kim is the Founder of Cendana Capital, a fund of funds that makes anchor investments in very early stage VC funds.
We talk characteristics of the best investors, how Cendana does diligence on fund managers, portfolio construction best practices, Michael’s “60x rule”, and why high ownership to fund size is the main driver of returns.
We also get in to how VCs are using AI, the competition between Seed and multi-stage investors, why US endowments are under siege, and how secondaries are driving most early stage venture returns today.
Michael also opens up about the early days of starting Cendana, the 18 month grind raising Cendana Fund 1, the day he almost died, and ranking in the top 2% globally in Call of Duty.
Special thanks to Roger Ehrenberg, Kevin Hartz, Semil Shah, Jeff Claviar, Beezer Clarkson, Jack Altman, Jeff Morris Jr, Sheel Mohnot, Nichole Wischoff, Ted Alling, and Rick Zullo for their help putting this episode together.
Thanks to Bolt for supporting this episode. Help them break a world record for the largest hackathon (up to $1m in prizes): https://bit.ly/ThePeelBoltHackathon
Timestamps:
(4:24) The day Michael almost died
(5:10) Call of Duty & video games
(9:34) Hiring @ Cendana
(10:31) How Cendana uses structured and unstructured data
(16:51) How VCs are using AI
(19:55) Why secondaries are driving most early stage venture returns
(22:01) Deciding when to sell secondaries
(24:28) Best performing venture funds ever
(27:26) The best VCs have amazing access to the best founders
(33:42) Why Cendana backs Solo GPs
(35:57) How to invest over time and hype cycles
(41:35) Why multi-stage firms are investing earlier
(44:45) Cendana’s current thesis: High ownership % to fund size
(45:51) Why Cendana started backing non-lead VCs
(48:41) How Cendana does diligence on fund managers
(52:22) VC NPS Scores and Ron Conway’s Silver Bullet
(53:49) Good vs bad new VC firm strategies
(56:36) Determining defensibility of a strategy
(57:57) “Messy middle” software buyout fund
(1:03:25) Portfolio construction best practice
(1:08:11) Michael’s 60x Rule
(1:14:28) How Seed funds compete with multi-stage funds
(1:20:05) Should you collect logos writing small checks?
(1:21:07) Becoming an LP for the city of SF
(1:24:42) Taking 18+ months to raise Cendana Fund 1 in the GFC
(1:26:48) Warehousing the first Cendana Fund 1 investments
(1:29:56) How to do a first close
(1:34:29) Why it’s hard to kill a VC firm
(1:37:00) What happens to ZIRP tourist fund managers
(1:40:22) How to raise a Fund 2 or 3 today
(1:42:07) “US endowments are under siege”
(1:44:55) What the best GP LP relationships look like
(1:46:41) What Fund of Funds get wrong
(1:50:43) The three most interesting trends in venture today
Referenced
Check out Cendana https://www.cendanacapital.com/
Deep Checks https://www.deepchecks.vc/
Prior episode with Eric at Bolt https://www.youtube.com/watch?v=7Q6n1vqUrF4
Follow Michael
Twitter: https://x.com/MKRocks
LinkedIn: https://www.linkedin.com/in/michael-kim-cendana-capital/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
How AI Changes Governments & Business Models, From $11 to $187M Exit | Mike Vichich, Pursuit
Mike Vichich is the Co-founder and CEO of Pursuit, which helps companies generate more revenue from the public sector.
We talk about how AI is changing Helmer’s 7 Powers, how it’s impacting the government, if DOGE is actually working, building a startup in the Midwest, and how to disagree with your team.
We also get into Mike’s prior company Wisely, and how they went from $11 in the bank account and unable to pay payroll for six months, to over $10 million ARR and a $187 million exit to Olo, a public company.
Thanks to Jack Altman and Blake Robbins for their help brainstorming topics for Mike!
Timestamps:
(3:21) How AI changes Helmer’s 7 Powers
(17:06) What becomes important in AI-first economy
(21:02) How AI interfaces with the government
(24:02) “The rules intended to save taxpayer money ironically cause taxpayer money to be wasted”
(29:34) How change orders impact public sector costs
(33:20) Why DOGE has not impacted US government spending yet
(38:15) Three pieces of wisdom from 2nd-time founders
(41:44) Starting Pursuit to make selling to the public sector as easy as the private sector
(45:35) Why cities grow expenses 5x faster than tax revenue
(51:42) Pros + Cons of building startups in Ann Arbor, MI
(57:43) Hiring talent density in the Midwest
(59:30) Starting his first company to fix consumer credit cards
(1:08:50) Pivoting Wisely to restaurant loyalty
(1:12:49) $11 in the bank, missing payroll for six months
(1:15:21) Embarrassing demo at an Ann Arbor tech meetup
(1:18:18) Why CEOs don’t always have to be right
(1:20:54) How to disagree
(1:25:48) Hiring at Pursuit
(1:28:30) “A bad day with customers is better than the best day in the office”
(1:31:33) Crashing their first customer’s PoS on Labor Day Weekend
(1:35:55) Using “The Cadence” to hit $10M ARR
(1:41:55) Selling Wisely to Olo for $187M
Referenced
- Check out Pursuit: https://www.pursuit.us/
- The Four Steps to the Epiphany by Steve Blank: https://www.amazon.com/Four-Steps-Epiphany-Steve-Blank/dp/0989200507
- Ann Arbor New Tech Meetup: https://www.meetup.com/a2newtech/
- How to Disagree: https://www.paulgraham.com/disagree.html
- The Cadence by David Sacks: https://sacks.substack.com/p/the-cadence-how-to-operate-a-saas-startup-436aa8099e8
Follow Mike
Twitter: https://x.com/mikevichich
LinkedIn: https://www.linkedin.com/in/mikevichich
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Ultimate Startup Growth Playbook, Using AI to Automate Operations | Sam Ross, Numeral
Sam Ross is the Co-founder and CEO of Numeral.
This conversation is a master class on all things growth at the zero to one stage. We talk early growth lessons from Airbnb, and stories from being one of the largest, earliest Facebook advertisers.
We get into working backwards from pockets of strong demand to find business ideas, how to establish early social proof around your product, why you shouldn’t hire a growth person as your first growth hire, how he raised Numeral’s Series A in four days, and why sales tax is so complicated and how they’re using AI to make it easy.
Timestamps:
(3:03) Why sales tax is so complicated
(8:06) Running crazy Facebook ads in 2013
(11:58) Why you need to be aggressive on new growth channels
(16:55) How strong retention unlocks massive businesses
(18:24) Using pockets of demand to find business ideas
(21:34) Balancing performance vs brand marketing
(25:45) How to build a brand from scratch
(29:11) When cold outbound actually works
(36:18) Building early social proof around your product
(43:33) Don’t hire career growth people for growth roles
(49:31) Lessons building a jewelry business doing $30m in revenue
(58:44) How the 2018 Wayfair v South Dakota decision led to Numeral
(1:05:04) Hacking an early product together with spreadsheets
(1:07:32) Automating the product
(1:15:26) What happens if you don’t pay sales tax
(1:20:41) How Numeral uses AI and LLMs internally
(1:26:41) How to compete against non-technical incumbents
(1:32:57) Why they raised VC for Numeral
(1:38:19) Raising a Series A in four days
(1:45:43) How big can a sales tax company really be?
(1:48:55) Creating a better global tax system
(1:54:31) How San Francisco is losing its soul
Referenced
Check out Numeral: https://www.numeralhq.com/
South Dakota v Wayfair: https://en.wikipedia.org/wiki/South_Dakota_v._Wayfair,_Inc.
Follow Sam
Twitter: https://x.com/SpamRoss
LinkedIn: https://www.linkedin.com/in/sambross/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Scaling Amplitude to $300M ARR with Co-founder and CEO Spenser Skates
Spenser Skates is the Co-founder and CEO of Amplitude.
Our conversation gets into the importance of data in product design and company building, how Amplitude is thinking about AI, and the future of user responsive software.
We also get into the early days of building Amplitude, when to go multi-product, how to construct your board as a startup, hiring executives at various company stages, lessons from closing three acquisitions, lessons scaling to $300 million in ARR, inside Amplitude’s 2021 IPO, and what most people get wrong about Founder Mode.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:45) Using data to build great products
(8:31) Why data is existential to every business
(13:14) How to go multi-product
(15:48) Every startup becomes a distribution company
(19:29) Lessons from three acquisitions
(29:09) AI hasn’t changed B2B SaaS yet
(31:24) Challenges of incorporating AI in B2B SaaS
(33:09) Amplitude’s AI experiments
(36:29) Navigating technology hype cycles as a public company
(39:40) Amplitude’s opportunity in LLMs
(43:08) User responsive software
(46:16) Surprising things that slow your speed of execution
(51:27) What people get wrong about Founder Mode
(59:48) Pivoting into Amplitude after YC
(1:04:42) Nine months to raise Amplitude’s first round
(1:08:31) Surprises from closing the first customers
(1:12:46) Two sales lessons for technical founders
(1:13:44) Scaling to $300M+ ARR
(1:17:14) How to choose board members
(1:19:55) Inside Amplitude’s IPO
(1:21:56) “Stock price is an output of the business”
(1:26:36) Evolving from startup founder to public company CEO
(1:31:54) How hiring execs changes as you scale
(1:34:32) Why DEI is important at Amplitude
(1:39:46) Relevance of gaming and startups
Referenced
Try Amplitude: https://amplitude.com/
Careers at Amplitude: https://amplitude.com/careers
Moxie Marlinspike’s web3 article:https://moxie.org/2022/01/07/web3-first-impressions.html
Sheep Logic: https://www.epsilontheory.com/sheep-logic/
Follow Spenser
Twitter: https://x.com/spenserskates
LinkedIn: https://www.linkedin.com/in/spenserskates
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Lessons Going Zero to $40M ARR in Two Years | Dan Lorenc, Chainguard
Dan Lorenc is the Co-founder and CEO of Chainguard, the safe source for open source.
The internet runs on free, open source software. But as its risen in popularity, its become the latest attack point targeted by hackers and nation states.
This conversation with Dan gets into the history of open source software, cloud computing, Linux, the software supply chain, how AI will impact it, and what the next big cyber attack will look like.
Dan is an engineer, but he also loves sales and go-to-market. We unpack how Chainguard went from zero to 150 customers and a $40m ARR in two years.
Chainguard just announced a $350 million Series D led by Kleiner and IVP, and Dan unpacks the round, plus shares his secret methodology for valuing the company.
A big thank you to Dan’s Co-founder Kim Lewandowski, to Clay Fischer @ Spark, Bogomil Balkansky & Andrew Reed @ Sequoia, and Tom Loverro @ IVP for their help brainstorming topics for Dan.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(3:26) A safe source for open source
(4:57) The software supply chain
(7:19) Can you trust open source code with contributors in Russia?
(9:43) Malware attack that almost took down the entire internet
(12:40) What the next big cyber attack will look like
(15:12) How will AI impact the software supply chain
(17:53) The history of cloud computing
(21:42) Why all cloud computing runs on Linux
(23:16) How Linux + Linux distros work
(29:28) Automating open source security
(32:43) Chainguard roadmap: Libraries and VMs
(36:40) Focusing on FedRAMP
(42:44) Impact of DOGE
(44:06) Zero to $40m ARR in two years
(45:40) Learning to love sales as a technical founder
(47:24) Lessons from Frank Slootman
(51:15) How to create urgency in sales
(53:16) How to build a sales team
(58:23) Hiring Ryan Carlson from Wiz & Okta
(1:01:45) Inside Chainguard’s $350m Series D
(1:07:41) Vibe coding + Dan’s software stack
(1:09:51) Cutting his hair in front of the entire company
(1:10:27) Wearing a different suit to each board meeting
(1:12:32) Bogomil, world’s best SDR
Referenced
Check out Chainguard: https://www.chainguard.dev/
Jobs at Chainguard: https://www.chainguard.dev/careers
Prior episode with Dan: https://www.youtube.com/watch?v=AC4cOJ9n_Z8
Linux Origin Email: https://www.reddit.com/r/linux/comments/mmmlh3/linux_has_a_interested_history_this_is_one_of/
The Qualified Sales Leader: https://www.amazon.com/Qualified-Sales-Leader-Proven-Lessons/dp/0578895064
Julius, AI data analysis: https://julius.ai/
Claude Code: https://www.anthropic.com/claude-code
World’s best SDR: https://x.com/BogieBalkansky/status/1913269714882814350
2025 Chainguard Assemble Keynote: https://www.youtube.com/watch?v=adfU9LJg3I0
Follow Dan
Twitter: https://x.com/lorenc_dan
LinkedIn: https://www.linkedin.com/in/danlorenc/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Surviving Two Seed Extensions, Fixing Auth for AI Agents | Clerk Founder & CEO Colin Sidoti
Colin Sidoti is the Co-founder and CEO of Clerk, the best way to build authentication and user management.
I loved this conversation, because Colin is currently in the arena building Clerk. It has not been easy, and he takes us inside some of the harder moments of the past six years.
We hit on three main themes: authentication; lessons raising multiple hard Seed extensions in the early days, including a recap before the A, and the demo that got a16z to invest; and things AI and MCP.
We also talk founding a company with his brother, building a compound startup, why components are the new APIs, and what he learned about audacious goals from John Collison @ Stripe
A big thank you to Reid Christian @ CRV, Paul Klein @ Browserbase, and Joseph Nelson @ Roboflow for helping brainstorm topics for Colin.
Timestamps:
(3:39) The best developer tool for authentication and user management
(5:45) The easiest way to set up billing
(7:13) Building a compound startup
(9:15) Lesson on audacious goals from John Collison
(12:40) Developer tools are now trusted category experts
(13:47) How auth impacts billing, CRM, marketing, analytics
(19:44) Why auth is always changing
(25:40) Coming up with the idea for Clerk
(29:24) What its like starting a company with your brother
(30:58) Living in a basement during Clerks early days
(35:33) Getting early users narrowing focus in South Park Commons
(40:10) Fundraising lessons from struggling to raise
(43:46) The trick that raised Clerk’s first round from S28
(45:09) Launching + the first Seed extension
(50:15) Sequoia’s feedback that improved conversion rates
(52:22) Why a16z led Clerk’s 2nd Seed extension
(58:11) How to do a recap before Series A
(1:03:34) Changing Clerk’s pitch to scare investors
(1:08:56) Fundraising advice “Why partner alignment is all that matters”
(1:11:42) Fast Series A and breaking 7%/week growth
(1:16:32) Negotiating Clerk’s Series B at the bar
(1:22:15) Investors in the arena vs in their mansions
(1:27:57) The three ways AI is changing authentication
(1:31:21) Why AI agents all try to steal free AI credits
(1:33:09) Remember to have fun
(1:36:24) Building a better product to compete in a crowded market
Referenced
Try Clerk: https://clerk.com/
Jobs at Clerk: https://clerk.com/careers
Martin Casado’s tweet https://x.com/martin_casado/status/1558134697753841664
Try Inngest: https://www.inngest.com/
Follow Colin
Twitter: https://x.com/tweetsbycolin
LinkedIn: https://www.linkedin.com/in/colin-sidoti-751a219
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Building Verkada, the $4.5B Physical Security Company | Filip Kaliszan, Founder and CEO
Filip Kaliszan is the Founder & CEO of Verkada, the physical security company.
Verkada started in 2016 by building the best camera for physical security teams, and has since evolved into a full suite of security products for buildings. Filip takes us inside Verkada’s rapid growth to almost a billion in annual revenue, over 2,000 employees, and raising capital from investors like Sequoia, Meritech, First Round, General Catalyst, and Next47.
We get into how AI and LLMs are changing hardware, the power of customer therapy, how Filip iterated on early startup ideas, inside Verkada’s very difficult first funding round, how signing their first big customers changed the trajectory of the business, and how to think about adding new products over time.
We also talk through Verkada’s commitment to in-person work in the summer of 2020, how you should evaluate joining a startup as an employee, Verkada’s “software zero” employee bonus policy, and building a rooftop bar for the office.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:20) Verkada, the physical security technology company + Demo!
(11:02) Building software powered hardware
(12:56) LLM opportunities in cameras
(15:49) Filip’s lifelong fascination with photography
(17:57) Taking one year to come up with the idea for Verkada
(22:27) Building his own home security system to learn the $16B market
(27:14) Why hardware experimentation is cheaper and easier than you’d think
(30:36) The importance of customer therapy
(32:37) How to get your first customers, importance of quick time to demo
(35:06) Why early fundraising was so hard
(40:38) Verkada’s first big customer
(42:23) How to decide what startup to join
(45:45) The opportunity in “smart building tech”
(50:34) How to launch new product lines
(58:07) Re-architecting the security industry to be software-native
(1:02:31) How hiring and managing a team changes as you scale
(1:08:55) Why each team at Verkada has its own recruiters
(1:14:00) Adding senior leaders to the team as you scale
(1:17:06) Evolving from introverted engineer to CEO of multi-thousand person company
(1:21:59) Verkada’s cool office and focus on in-person work during COVID
(1:28:12) Building a rooftop bar on the office
(1:32:20) Verkada’s Software Zero employee bonus program with 40x ROI
(1:36:00) How Filip thinks about IPO vs staying private
Referenced
Verkada: https://www.verkada.com/
Open roles at Verkada: https://www.verkada.com/careers/
Follow Filip
LinkedIn: https://www.linkedin.com/in/kaliszan/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Forage: The Trillion Dollar Opportunity in Restricted Payments | Ofek Lavian
Ofek Lavian is the Co-founder and CEO of Forage, the mission driven payments company.
This is a special episode, because I’m an investor in Forage, and Ofek shares everything he’s learned building the company. We go deep on food stamps, also known as EBT or SNAP, the government program that provides over $200 billion dollars per year in benefits that help 42 million low income Americans buy food.
Our conversation gets into lessons from Ofek’s time leading payments teams at Uber and Instacart, building Instacart’s EBT program up to 40 employees and 10% of its total revenue, and why Ofek is so passionate about helping low income Americans.
We get into the history of food stamps, market dynamics that led to low online adoption, the days Ofek thought Forage might not make it all the way to now working with the biggest players in online grocery, like Uber and DoorDash, and the long-term opportunity Forage has to build the rails the government uses to distribute trillions of dollars of restricted consumer benefits.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:53) Forage: Helping 42m Americans buy food
(5:24) History of food stamps & EBT
(9:26) Growing up as an immigrant family with low food access
(11:39) 90% of EBT recipients are elderly, disabled, or working parents
(12:39) How Forage sells revenue to its customers
(14:15) Building Instacart’s EBT program during COVID
(18:25) Why no one built an EBT payments product
(22:13) Joining Forage as a Co-founder
(25:01) Why government payments are so hard
(30:25) Growing 15x in six months
(33:52) Underdiscussed mental health challenges of startups
(37:06) How the political environment impacts EBT
(43:20) Why Forage charges more than competitors
(45:58) Seasonality in EBT spend
(46:59) Why early investors passed on Forage
(48:10) The trillion dollar opportunity in restricted payments
(50:56) “ There's no single idea that has destroyed more business value on planet Earth than the idea that micromanagement is bad.”
(54:45) Why Forage doesn’t care about job titles
(58:51) Lessons backpacking across 28 countries after college
(1:02:09) How to travel on a budget
(1:04:24) Importance of health
(1:06:15) Saving a friends life on Mount Everest
Referenced
Forage: https://www.joinforage.com/
Ofek’s viral tweet: https://x.com/OfekLavian/status/1766950034581700697
Follow Ofek
Twitter: https://x.com/OfekLavian
LinkedIn: https://www.linkedin.com/in/ofeklavian/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
How the World’s Most Active Angel Investor Operates | Ed Lando, Founder of Pareto Holdings
Ed Lando is the Co-founder of Pareto, where he’s been an early investor in over 25 unicorns, started and incubated over 10 companies, and was recently named the most active angel investor in the world according to Crunchbase.
We get into how Ed first got started angel investing, how he built up deal flow, why he’s historically kept a low profile, and why he hasn’t raised outside capital.
We also talk concentration vs diversification, why there’s many ways to build successful companies, advice on hiring your first employees, and his playbook for incubating companies at Pareto, which is where he focuses most of his time.
Timestamps:
(0:00) Intro
(2:51) Getting into angel investing
(3:58) Debating high vs low PR strategies
(8:27) How to start building deal flow when angel investing
(10:00) Pareto: first investor in people leaving school or their job
(12:05) Evolving from angel to fund
(14:57) Why Ed didn’t raise outside capital
(20:33) Concentration vs diversification
(28:29) Investing in non-sexy categories
(32:50) There’s no one right way to build a company
(36:03) When to go against traditional wisdom
(39:36) Lessons from his anti-portfolio
(45:59) Ed’s close relationship with his parents(
(49:04) How we’re using AI
(54:04) Incubating companies
(58:38) Investing beyond spreadsheets and DCF models
(1:05:49) How to trust your intuition investing
(1:09:47) How to move fast
(1:14:24) What most people get wrong when incubating companies
(1:18:40) How to hire your first employees
(1:26:27) Navigating hype when building and investing
1:29:59 Venture math and the Power Law
1:35:33 How Ed and Pareto’s strategy might break
1:38:45 Differences between the US and Europe
Referenced
Pareto: https://pareto20.com/
Misfit Market: https://www.misfitsmarket.com/
Catalina Crunch: https://catalinacrunch.com/
Zamp: https://zamp.com/
Magnus Carlsen on Joe Rogan: https://www.youtube.com/watch?v=ybuJ_nIXwGE
Follow Ed
Twitter: https://x.com/edwardlando
LinkedIn: https://www.linkedin.com/in/edwardlando/
Substack: https://edwardlando.substack.com/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Alloy’s Unconventional Path to $1.5B with Tommy Nicholas, Co-founder and CEO
Tommy Nicholas is the Co-founder and CEO of Alloy, the identity and fraud prevention platform trusted by over 700 financial service companies.
Our conversation explores the early days of fintech, why more consumer financial protections actually lead to more fraud, and gets into the weeds of various tactics he’s learned building a technical platform company like Alloy.
We talk about embracing that the hard parts of company building are actually the best parts, why you’re most likely to give up when things first start getting better, using hands-on sales implementations in the early days to gave Alloy product market fit on steroids, how hiring changes as you scale, getting 100’s of no’s over 20 months raising their Seed round, and why TAM doesn’t matter.
Thanks to Charley Ma for his help brainstorming topics for Tommy!
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try them here: https://bit.ly/NumeralThePeel
Timestamps:
(3:56) The platform to manage fraud
(5:48) What fintech risk was like in the early 2010’s
(14:34) Why company building never gets easier
(19:30) Reasons the hard stuff is actually the good stuff
(24:00) You’re most likely to give up when things start getting better
(33:47) Doing hands-on sales implementation to get PMF on steroids
(42:26) Deciding when PLG or hands-on sales will work best
(52:33) Why more consumer financial protections leads to more fraud
(58:14) 20 months to raise $2m vs $200m from a spreadsheet
(1:06:32) “Make yourself look like a good investment”
(1:10:14) Why TAM doesn’t matter
(1:14:35) How to hire collaborative problem solvers
(1:24:38) Why Alloy didn’t do much marketing early on
Referenced
Try Alloy: https://www.alloy.com/
Charley Ma’s Pod Episode: https://youtu.be/5cxgB1_q2lw
Try Artie: https://www.artie.com/
Follow Tommy
Twitter: https://x.com/tommyrva
LinkedIn: https://www.linkedin.com/in/tommynicholas
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
The $750 Billion AI Opportunity in Customer Service | Mike Murchison, Co-founder and CEO of Ada
Mike Murchison is the Co-founder and CEO of Ada, the AI-powered customer service automation platform.
Ada’s product and scale puts Mike at the forefront at how AI is changing software and labor markets, and this conversation felt like both a glimpse into the future, and a look into the past, at a story of pure grit and determination, working seven customer service jobs at once.
We talk about why management capabilities becomes even more important in AI-native companies, how customer service is changing from a cost center to a revenue driver, and how to talk to customers more as you scale.
We also get into why AI is still underhyped, what truly AI native software looks like, the realities of selling enterprise AI software today, and advice for anyone building an AI agent from scratch.
Thanks to Boris Wertz and Fahd Ananta for their help brainstorming topics for Mike!
Timestamps:
(00:00) Intro
(03:49) Making customer service extraordinary for everyone
(05:44) Management becomes more important in AI-first companies
(12:13) From customer inquiry to solution in production, fully autonomously
(16:01) Why companies talk to customers less as they grow
(20:36) Creating new products from customer service data
(22:45) Broken incentives in customer service
(26:10) Working 7 customer service agent jobs at once for a year
(37:19) Why pivoting to Ada felt like failure
(46:11) How Mike would build an AI agent from scratch today
(49:15) Ways AI will change how we build and manage companies
(56:44) Why the best managers are great users of AI
(1:00:27) How the top 1% of people are using LLMs
(1:06:22) Realities of selling enterprise AI software today
(1:11:02) Building a sales team from scratch
(1:15:21) Reflecting on Ada’s scale + doubling the last six months
(1:16:41) Biggest software category of all-time ($750B)
(1:19:51) Why AI is still under hyped
(1:21:01) Ego is the biggest inhibitor to AI adoption
(1:23:33) How AI will fuel explosion of creativity and productivity
(1:25:20) Large companies will benefit the most from AI
(1:27:41) Multi-modal language models and autonomous (computers
Referenced
Try Ada: https://www.ada.cx/
Follow Mike
Twitter: https://twitter.com/mimurchison
LinkedIn: https://www.linkedin.com/in/mikemurchison
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
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Why Founders are Moving to Chattanooga, Tennessee to Lock-in | Cam Doody at Brickyard
Cam Doody is the Co-founder and General Partner of Brickyard, the venture capital firm moving founders to Chattanooga, Tennessee to lock-in with no distractions until they find product market fit.
Brickyard is one of the most unique venture firms you’ll ever come across, and we get into how it how it was inspired by a 16x fund based in Chattanooga, why Cam and his co-founders started it during ZIRP, and why they hope everyone copies their model.
We also get into Cam’s startup Bellhops, which he started in 2011 and has since grown into the third largest moving company in the US. We talk running a local services business, why 5-star review systems don’t work, and how U-Haul almost killed Bellhops overnight back in 2016.
Thanks to Nader Khalil, Matt Harb, Austin Beveridge, and Spencer Levitt for their help brainstorming topics for Cam!
Timestamps:
(0:00) Intro
(03:33) Chattanooga: Dirty manufacturing city to high tech
(05:23) Brickyard’s precursor, the Lamp Post Group (a 16x fund)
(09:46) How ZIRP screwed up early stage investing
(13:49) What is Brickayrd?
(21:14) Getting Brickyard off the ground in 2021
(26:25) 100+ year old rug warehouse + maintenance nightmares
(33:13) Cam wants everyone to copy Brickyard
(36:31) Why economic development startup programs don’t work
(38:59) YC teams doing Brickyard to escape the Trough of Sorrow
(44:07) How Brickyard companies raise Series As
(46:10) Nvidia acquiring Brev
(52:18) How to deal with a co-founder breakup
(55:45) Starting Bellhop to build a better moving company
(1:02:27) How U-Haul almost killed them overnight
(1:06:54) Marketing tactics for a local services business
(1:12:05) Why 5-star review systems don’t work
(1:18:16) How Cam’s view of VC’s changed after becoming one
(1:20:37) Ways VC’s actually add value
(1:25:05) The thesis for Bitcoin
(1:39:21) Cam’s annual remote desert island vacation
Referenced
Check out Brickyard: https://www.justlaybrick.com/
The Trough of Sorrow: https://andrewchen.com/after-the-techcrunch-bump-life-in-the-trough-of-sorrow/
Bellhops: https://www.getbellhops.com/
Follow Cam
Twitter: https://www.twitter.com/camdoody
LinkedIn: https://www.linkedin.com/in/cam-doody-b489a124
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Zero to $20m ARR in Two Months: Inside Bolt’s 7-Year Journey to Overnight Success | Eric Simons, Co-founder & CEO
Eric Simons is the Co-founder and CEO of StackBlitz, best known for its breakout product Bolt, letting anyone build full stack apps from text, in the browser.
Bolt launched in October of 2024, quickly growing from zero to a $20 million revenue run rate in two months, making it one of the fastest growing products ever. But Eric will be the first to tell you it wasn’t an overnight success - the product didn’t even work the first time they tried building it.
We go behind the scenes of the seven year journey building the tech that eventually led to Bolt, how to avoid distractions, being capital efficient, living in a frat house for $100/month, and squatting in AOL’s headquarters for $1/day when he was 19.
Eric also takes us inside the weeks after Bolt’s viral launch, figuring out a new business model on the fly, his strategy for fundraising and PR, why you should open source your code, Bolt’s playbook for building a community around the product that enabled their viral launch, and how AI is changing software forever.
Timestamps:
(0:00) Intro
(2:24) Building full stack apps from text, in your browser
(4:19) Running an operating system in the browser
(11:48) Why Bolt failed the first time, almost shutting down the company last summer
(20:18) How Bolt went viral from one tweet
(28:33) Differences between ChatGPT, Claude, Cursor
(39:38) Why AI code gen changes the software world order
(42:01) What happened inside Bolt going from zero to $20m ARR in two months
(47:32) Not sharing fundraises publicly + his PR strategy
(58:57) Why the team never gave up for seven years
(1:01:07) Living in a frat house for $100/month
(1:04:07) How to be capital efficient
(1:09:00) Living on $1/day in AOL’s HQ when he was 19
(1:14:01) Inside Bolt’s Series B
(1:21:03) Bolt’s hiring and product roadmap
(1:32:58) Creating a new inference-based AI business model
(1:38:07) Eric's playbook for building a community of users
(1:44:05) Why you should open source your code
Referenced
Try Bolt: https://bolt.new/
Bolt on X: https://x.com/boltdotnew
Check out Webcontainers: https://webcontainers.io/
$0 to $4m ARR case study with Anthropic: https://www.anthropic.com/customers/stackblitz
Bolt’s open source code: https://www.bolt.diy/
Bolt / StackBlitz is hiring! https://stackblitz.com/careers
Eric’s favorite cafe, The Lighthouse SF: https://thelighthousessf.com/
Lady Gaga’s “one person” montage: https://www.youtube.com/watch?v=iRxsX_30tjs
Living inside AOL HQ at 19 years old: https://www.cnet.com/tech/tech-industry/meet-the-tireless-entrepreneur-who-squatted-at-aol/
Bloomberg coverage of StackBlitz Series B: https://www.bloomberg.com/news/articles/2025-01-21/ai-speech-to-code-startup-stackblitz-is-in-talks-for-a-700-million-valuation?embedded-checkout=true
Joel Spolsky’s blog: https://www.joelonsoftware.com/
Follow Eric
Twitter: https://x.com/ericsimons40
LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Rick Zullo on Building Equal Ventures, Why Traction is Overrated, Advice for Emerging Managers
Rick Zullo is the Founder of Equal Ventures. Our conversation gets into Equal’s unique approach to venture capital, thinking more like public market and private equity investors, and why they also think traction is overrated at Seed.
We talk through Equal’s thesis-driven model, employing a team of product owners, only investing in only 3 to 5 themes at once, and Rick’s admiration of Charlie Munger.
We also talk AI - who will benefit the most, what he does and doesn’t like in terms of investing in the space, why venture capital is not really venture capital anymore, and why it sucks to be a Seed investor right now.
Rick also runs the Emerging Manager Circle, a group for emerging fund managers. We get into the origin story of the group, his own struggles raising his first fund, and why talent is leaving the mega funds.
Timestamps:
(00:00) Intro
(03:38) Why venture capital isn’t venture capital anymore
(11:33) How founders should approach raising a Seed round
(14:13) The realities of downrounds
(15:55) Rick’s favorite founders that raised little capital
(18:54) Biggest fundraising mistake founders make
(21:21) Why we need to stop funding AI companies
(28:34) How AI will benefit private equity the most
(33:30) Three levels of opportunity in AI right now
(38:36) Why traction is overrated at Seed
(41:38) Investing in businesses with compounding returns on capital
(52:07) VC lessons from PE firms
(56:24) Why Seed investing sucks right now
(1:04:15) The beauty of small exits
(1:12:52) How failing to start a fund in college led to Equal Ventures
(1:20:06) The struggle raising Equal’s $55m Fund 1
(1:23:23) Why the best talent is leaving mega VC firms
(1:30:16) The Emerging Managers Circle
Referenced
* Equal Ventures: https://www.equal.vc/
* EMC Summit: https://www.emcsummit.com/
Follow Rick
Twitter: https://x.com/Rick_Zullo
LinkedIn: https://www.linkedin.com/in/rickzullo/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Illegal Immigrant to $160m Fund 1: Inside Villi Iltchev’s Journey Building Category Ventures
Villi Iltchev is the founder of Category Ventures, where he invests early in enterprise software startups. And he’s done it longer than almost anyone, building Salesforce’s corporate venture arm and investing early in companies like Airtable, Zapier, GitLab, Remote, Hubspot, Gusto, and Box.
Fresh off raising his $160m Fund 1, we get into the opportunity he saw to start Category, and how San Francisco and Silicon Valley have changed over the past 30 years.
He also shares his story growing up as an illegal immigrant in Greece, moving to the US by himself in high school, the biggest mistake of his career, advice for founders selling their company, why unit economics and profitability always matters, how developer tools went from terrible to amazing businesses, the mistake that almost killed GitLab after he invested, and why you should raise your seed round from a seed fund.
Timestamps:
(00:00) Intro
(03:22) Illegally immigrating from Bulgaria to Greece
(05:14) Moving to the US by himself in high school
(13:15) Moving to SF in the Dot Com Bubble
(15:49) How SF changed over the last 25 years
(22:27) Why HP fell from the top of Silicon Valley
(25:36) Building Salesforce’s corporate VC arm
(30:29) Why SaaS was so transformative
(34:35) Angel investing in Airtable
(39:52) The biggest mistake of his career
(42:13) Why unit economics always matter
(47:20) Biggest mistake when selling a tech company
(49:00) Almost starting a software PE firm and landing in VC
(55:45) Lessons from August Capital + Evolution of venture
(59:22) Early days of dev tools + Investing in GitLab
(1:09:50) Why being contrarian is dumb
(1:11:45) How GitLab almost died and emerged stronger
(1:16:48) Villi’s journey to starting Category
(1:25:22) Category’s thesis
(1:30:48) Why startups always come in batches
(1:31:57) The importance of track record in venture
(1:35:32) Deciding a $160m fund size
(1:39:26) Why you should raise seed rounds from seed firms
(1:43:40) What Villi looks for in a startup
Referenced
Category VC: https://www.categoryvc.com/
Category’s $160m Fund 1: https://www.forbes.com/sites/alexkonrad/2024/12/17/villi-iltchev-raises-160-million-debut-fund-category/
Aaron Levie (Box) on The Peel: https://youtu.be/cLn_tqPvNf4
GitLab’s Recovery Stream: https://www.youtube.com/watch?v=v0TRHLvYGE0
Guy Podjarny (Snyk) on The Peel: https://youtu.be/BzKlZ_v4uCw
Why SaaS won’t consolidate: https://medium.com/@villispeaks/why-saas-consolidation-is-not-happening-2b9b722e0250
Follow Villi
Twitter: https://x.com/villi
LinkedIn: https://www.linkedin.com/in/villi04/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
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Govtech + Drones Crash Course, Lessons From 2 Exits | Rahul Sidhu
Rahul Sidhu is the co-founder of SPIDRTech and Aerodome, two companies in the public safety space.
He’s sold both of them, and our conversation unpacks all the lessons he learned, what he did differently with his second company Aerodome, and why he sold only 17 months after starting it.
If you tuned into last week’s episode, Paul told us to never talk to the cops. Rahul gives us the other side of the story, sharing his playbook for selling to police, the government, how he met Nikita Bier in high school, and why he’s still bullish on drones, robotics, and AI in the physical world.
Timestamps:
(00:00) Intro
(04:07) What its like testifying to Congress
(08:06) Why 90% of what he knew about police was wrong
(13:15) How to sell to police departments
(15:24) His first business selling WoW accounts
(19:00) Meeting Nikita Bier in high school
(21:29) Starting SPIDRTech to improve police + community relationships
(27:45) Two biggest mistakes building SPIDR
(31:47) How startups break down when scaling
(34:19) Selling SPIDR instead of raising a Series B
(40:12) Why Aerodome was so much easier to start
(42:55) Why Rahul loves unsexy markets with founder market fit
(46:03) Starting Aerodome, drones as first responders
(53:39) Building a capital efficient hardware startup
(56:46) How regulatory changes made an opening for Aerodome
(01:00:13) Inside Aerodome’s Series A
(01:03:57) Selling Aerodome to Flock Safety within 17 months
(01:09:31) Saying “would I work for this team?” when getting acquired
(01:14:35) Seeing a homeless guy in an Aerodome shirt
(01:17:02) The massive Robotics + AI opportunity this decade
(01:21:42) What’s really happening with drones in New Jersey
Referenced:
SPIDRTech: https://www.spidrtech.com
Aerodome: https://www.aerodome.com/
Nikita Bier’s Ted Talk: https://www.youtube.com/watch?v=k9QTVII_lkg
Follow Rahul:
Twitter: https://x.com/rahoolsidoo
LinkedIn: https://www.linkedin.com/in/rahulsidhu/
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Infrastructure for AI Browsers with Paul Klein, Founder + CEO of 🅱️ Browserbase
Paul Klein is the Founder and CEO of Browserbase, building infrastructure for AI browsers.
Our conversation gets into the future of software and AI agents, why authentication is a huge problem in AI, how the best infrastructure companies become product companies, and the memo he wrote that convinced him to start Browserbase despite not wanting to build another company.
A year ago, Paul was a relatively unknown commodity, and definitely did not want to raise venture capital again. He shares the playbook he used to go from zero to raising $27 million in nine months “as a non-famous person” (his words).
He shares all his lessons learned in the arena as he’s processing them, like what he thinks will unlock better AI agents, why you should like your own tweets, and how Browserbase competes with incumbents.
Timestamps:
(00:00) Intro
(02:39) How LLMs unlock automation online
(08:34) The future of software (AI agents)
(11:21) Why AI agents need better authentication
(12:59) Lessons from Twilio on building an infrastructure company
(17:27) Learnings from his first startup
(19:56) Bubbles, and how they drive innovation
(20:37) Reasons this moment in AI is special
(29:58) Why technical founders love post-PMF
(31:55) The memo that started Browserbase
(34:09) Why a startup should be a means of last resort
(36:53) Being a solo founder
(42:24) Importance of in-person culture
(45:56) The best place to find engineers
(48:34) How Paul hired a contractor army to build Browserbase
(50:16) Why you can’t hire mercenaries
(54:28) The power of emojis in marketing
(57:39) Browserbase's early growth playbook (3 videos)
(01:04:00) Benefits of sharing an office with other startups
(01:06:00) Sales lessons from his parents
(01:08:07) Why startups are like video games
(01:13:43) Successful founders work the hardest and are shameless
(01:18:44) Customer support is a startups greatest differentiator
(01:22:06) Paul’s playbook that raised $27m in nine months as a non-famous person
(01:29:03) How investors make decisions
(01:33:10) Risks help startups avoid competition
(01:36:37) Great infrastructure needs its own frameworks
(01:39:05) Long-term thinking in LLMs will enable mass AI agents
(01:42:21) Avoiding tech debt with AI moving so fast
(01:43:48) Infrastructure companies need to become product companies
(01:46:54) The Sine Wave philosophy to startups
Referenced:
Browserbase: https://www.browserbase.com/
An Internet Browser for AI: https://memos.hawkhill.ventures/p/an-internet-browser-for-ai
Rise of the Product Engineer: https://memos.hawkhill.ventures/p/rise-of-the-product-engineer
Death to the Backend: https://memos.hawkhill.ventures/p/death-to-the-backend
The three Browserbase marketing videos
Pre-Seed: https://x.com/pk_iv/status/1775183751800377344
Seed: https://x.com/pk_iv/status/1798731220005883935
Series A: https://x.com/pk_iv/status/1851270308701106383
Follow Paul:
Twitter: https://x.com/pk_iv
LinkedIn: https://www.linkedin.com/in/paulkleiniv/
Follow Turner:
Twitter: https://x.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
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Robinhood Co-founder Baiju Bhatt on the Journey to $40B, Building Space Solar Power with Lasers
You’re probably familiar with Baiju Bhatt’s work as the co-founder of Robinhood. But he’s also obsessed with space, and recently started Aetherflux, a space solar power company.
We get into the physics of using lasers to beam solar power to the Earth, Aetherflux’s early roadmap, and how he went from zero to one going from building software to physical products.
We also talk through the early days of Robinhood, getting turned down by hundreds of early investors, the accidental launch, how to know if you really have product market fit, how Aaron Levie at Box helped get Robinhood.com, the value of creativity and design, Baiju’s philosophies on combining qualitative and quantitative user research, and his favorite animal and classic car. He also tried to cut my hair.
Timestamps:
(00:00) Intro
(02:31) Aetherflux: a space solar energy company
(02:50) Origins of space solar power in the 40's & 70's
(10:31) Safely beaming energy from space to Earth with lasers
(13:46) Building floating space solar farms
(21:27) Aetherflux's early roadmap
(27:08) Growing up with dad as a Physics professor
(32:18) Going zero to one building physical products
(35:15) Baiju's favorite car, attempting a haircut, contemplating mustaches
(38:27) Trying to prove Einstein wrong
(41:42) Meeting Robinhood Co-founder Vlad at Stanford
(44:10) Starting an algorithmic trading company
(46:41) The beginnings of Robinhood
(52:04) Getting turned down by hundreds of early investors
(56:49) How they convinced Tim Draper to invest
(59:39) Getting Robinhood.com because of Aaron Levie
(01:01:28) Accidentally launching on a Friday afternoon
(01:03:09) How to know if you have Product Market Fit
(01:06:35) Combining qualitative and quantitative user research
(01:14:23) Loving cats despite being allergic
Referenced:
Robinhood: https://www.robinhood.com
Aetherflux: https://www.aetherflux.com/
TechCrunch coverage: https://techcrunch.com/2024/10/09/billionaire-robinhood-co-founder-launches-aetherflux-a-space-based-solar-power-startup/
Seinfeld mustache scene: https://www.youtube.com/watch?v=DzZsLaLChRg
The Michelson–Morley experiment: https://en.wikipedia.org/wiki/Michelson%E2%80%93Morley_experiment
Episode with Aaron Levie @ Box: https://www.youtube.com/watch?v=cLn_tqPvNf4
Follow Baiju:
X/Twitter: https://x.com/BaijuBhatt
LinkedIn: https://www.linkedin.com/in/bprafulkumar
Follow Turner:
X/Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Sheel Mohnot on All Things Fintech, Starting Better Tomorrow Ventures
Sheel Mohnot is the Co-founder of Better Tomorrow Ventures, an early stage fintech focused fund leading rounds in pre-seed and seed-stage companies.
Our conversation weaves through Sheel’s two decades of building and investing in fintech, starting BTV, and why they started a fintech-focused accelerator, The Mint.
Fun facts on Sheel, he was a contestant on the Zoom Bachelor during COVID lockdowns, in a Justin Bieber music video, got married in the Taco Bell Metaverse, and was once banned from Uber.
We talk lessons competing against Stripe before selling his first company, common fintech startup pitfalls, and the trick every VC should use when fundraising.
Timestamps:
(00:00) Intro
(03:13) Why fintech makes disproportionate positive change
(07:49) Most interesting opportunities in fintech today
(09:09) The accountant shortage
(12:59) Common early fintech startup pitfalls
(16:09) Building Fee Fighters to cut payment processing fees
(21:15) Lessons competing with Stripe
(21:57) Getting acquired by Groupon and adding $600m in market cap
(25:11) Biggest first-time startup mistakes
(29:21) Getting $10k in Uber credit via paid Google ads
(32:13) Investing in Flexport
(36:19) Navigating hot vs underhyped rounds
(43:39) Sheel’s domain auction company
(53:18) How he started angel investing
(54:57) Spotify acquiring his podcast “The Pitch”
(59:55) Why accelerators succeed and fail
(01:06:07) The Mint, BTV’s fintech-focused accelerator
(01:09:56) Camp BTV in the Santa Cruz Mountains
(01:11:41) Early days of NerdWallet
(01:14:55) Raising $75m BTV Fund 1 with Jake to fill a gap in the market
(01:18:36) Understanding Fund of Funds incentives
(01:22:15) References in VC fundraising
(01:24:02) $150m BTV Fund 2
(01:27:13) Importance of following-on when leading rounds
Referenced:
BTV: https://www.btv.vc/
The Mint: https://www.themint.vc/
Fee Fighters: https://techcrunch.com/2011/09/23/feefighters-launches-payment-gateway-samurai/
Follow Sheel:
Twitter: https://x.com/pitdesi
LinkedIn: https://www.linkedin.com/in/smohnot/
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Life360's 17-Year Journey to $3B | Chris Hulls, Founder and CEO
Chris Hulls is the co-founder and CEO of Life360, the social network for families. At the time of recording, its the 15th largest app in the US, with over $330 million in annual revenue, and valued at over $3 billion in the public markets.
We go inside the two decade journey building Life360, competing against Sam Altman and Woz, almost getting cancelled on TikTok, and going public twice - first in Australia, then again in the US.
Timestamps:
(00:00) Intro
(02:04) Why CEO’s are getting more authentic
(04:59) Building a social network for family
(08:14) Starting Life360 after Hurricane Katrina
(12:23) $30k from mom and a professor
(13:52) $300k grant from Google
(16:13) Launching on the first Android phones
(18:20) Competing against Sam Altman, Steve Wozniak
(19:06) “If we trusted the data, we would’ve shut down”
(24:22) Why doubters lead to less competition
(25:49) Fundraising in an unsexy market
(32:21) Almost getting cancelled on TikTok
(41:42) Building a contextual advertising business
(48:36) Acquiring Tile, launching hardware products
(52:41) Defeating patent trolls
(57:22) IPO’ing in Australia and the US
(01:01:00) Why its hard to go public below a certain size
(01:07:50) 70% drop in downloads during COVID
(01:10:03) Get to know your competitors
(01:15:05) Lean Startup philosophy went too far
Referenced:
Try Life360: https://www.life360.com/
Wheels of Zeus: https://en.wikipedia.org/wiki/Wheels_of_Zeus
Chris’ TikTok journey: https://www.entrepreneur.com/leadership/how-life360s-founder-dealt-with-teens-mocking-him-on-tiktok/457879
Chris’ TikTok: https://www.tiktok.com/@life360ceo
Follow Chris:
Twitter: https://x.com/ChrisHulls
LinkedIn: https://www.linkedin.com/in/chrishulls/
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Unlocking AGI With Visual AI Agents | Joseph Nelson, Roboflow
Joseph Nelson is the Co-founder and CEO of Roboflow, making the world programmable by building computer vision tools for developers and enterprises.
We talk about how computer vision creates a new paradigm to program the world, and how visual AI is the missing piece of AGI.
Joseph also shares multiple live product examples, how computer vision unlocks new data sources, lessons from Stripe and Palantir, building business models in developer tools, his experience working with David Sacks, and developer marketing tactics and how Roboflow consistently gets to the front page of Hacker News.
Timestamps:
(00:00) Intro
(03:34) Computer vision is the missing piece for AGI
(05:59) Vision as a new paradigm to collect data
(10:55) Live examples of computer vision
(13:45) How a Magic Sudoku solver app led to Roboflow
(18:13) Using computer vision for automation
(24:49) Computer vision in sports
(27:02) How vision unlocks new data sources
(28:24) Inside developer tool business models
(33:32) The "Collison Install" and hands-on customer service
(36:45) When to adopt Palantir's Forward Deployed Engineers
(43:44) Why AI companies need to combine PLG and enterprise sales
(50:12) Advice on developer marketing
(52:30) Roboflow's greatest hits on Hacker News
(01:02:19) Benefits of David Sacks as AI & Crypto Czar
(01:05:32) Why all new technology has bad actors
(01:07:07) Why over-regulation holds back innovation
(01:12:01) How to get on the front page of Hacker News
(01:19:43) Multi modality, time recognition, and agentic vision
(01:28:36) Image-to-image prompting
(01:30:42) Growing up in Iowa
(01:32:20) Making TI-84 calculator games in high school
(01:36:32) Pioneer: hunger games for startups
(01:40:16) Why Roboflow does weekly Ship Lists + Ship and Tell
(01:42:46) Hiring former founders and "full stack people"
(01:45:16) Designing a bottoms-up organization while scaling
(01:50:35) Why candidates build with Roboflow in hiring process
(01:55:08) Hiring someone to help with the podcast
Referenced:
Robowflow: https://roboflow.com/
Roboflow Universe: https://universe.roboflow.com/
Paint.wtf: https://paint.wtf/
Roboflows NeurIPS Presentations: https://blog.roboflow.com/neurips-2023-papers-highlights/
Careers at Roboflow: https://roboflow.com/careers
Follow Joseph:
Twitter: https://x.com/josephofiowa/
LinkedIn: https://www.linkedin.com/in/josephofiowa
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
How Morning Brew Grew to 6 Million Subscribers and $70 Million Revenue in Six Years | Austin Rief, Co-founder & CEO
Austin Rief is the Co-founder & CEO of Morning Brew, building the Wall Street Journal for the next generation. They started the company in 2017, and grew it to 6 million subscribers and $70 million in revenue in six years.
We talk through the journey starting Morning Brew with Co-founder Alex Lieberman while students at the University of Michigan, and Austin's playbook for starting a new media company from scratch today. We get into the creator economy, early stage investing, ad based business models, being the first advertiser on Instagram Stories, advice for hiring, and his secret for sourcing remote talent in Sri Lanka.
Timestamps:
(00:00) Intro
(03:42) How to start a media company from scratch today
(13:01) Future of the creator economy is niche products
(14:42) Opportunity in B2B media today
(17:05) Reflecting on investing during ZIRP
(21:30) Why its starting to feel like 2021 again
(23:16) Talking VC portfolio math
(27:09) Starting Morning Brew with Wall Street interview prep
(33:35) Being so dumb that they never pivoted from being a newsletter
(35:29) How newsletter business models works
(38:32) Morning Brew’s first viral Instagram post
(40:37) Acquiring subscribers for two cents on Instagram Stories
(42:29) Nik Sharma’s poor mans paid ads strategy
(44:32) Landing Discover as their first big sponsor
(46:06) How agencies and ad buying works
(49:49) Why sales roles are so hard to hire for
(53:04) Importance of offsheet references
(57:43) Sourcing talent in Sri Lanka with Oceans
(01:04:23) Austin and Alex’s unique co-founder dynamics
(01:07:16) Dental plans, rotisserie chickens, and company laptops
(01:10:00) Building WSJ for the next generation
Referenced:
Morning Brew: https://www.morningbrew.com
Try Oceans: https://www.oceanstalent.com/
Kevin Espiritu episode: https://www.youtube.com/watch?v=FefGL-qPzDo
Craig Fuller episode: https://www.youtube.com/watch?v=oPPqO8eBq2M
Forbes article: https://www.forbes.com/sites/hayleycuccinello/2019/02/07/morning-brew/
Follow Austin:
Twitter: https://x.com/austin_rief
LinkedIn: https://www.linkedin.com/in/austin-rief/
Newsletter: https://www.theaustinbrief.com/
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
The Startup Teaching 2-Year Olds to Read | Niels Hoven, Mentava
Niels Hoven is the founder of Mentava, building software to accelerate kids’ education, starting with teaching two year old’s to read.
We talk about how public education isn’t designed for ambitious kids, the power of hater marketing, product design from zero to one, how too much data leads to Frankenstein products, Seed stage fundraising advice, parenting hacks, why AI won’t have a big impact on education, and the future of elite higher ed.
For full show notes, visit: https://highlightai.com/share/0a0869a7-c345-4974-ba2b-726bacf7a534
Timestamps:
(00:00) Intro
(03:49) Why schools don’t challenge overachievers
(11:58) How a hater made Mentava go viral
(18:14) The secret that teaches little kids to read
(24:22) How people actually learn to read
(27:35) 2/3 of 4th graders can’t read proficiently
(29:29) The downfall of one-size fits all education
(33:44) How California almost banned middle school algebra
(40:41) SF’s lottery system and how it impacts low income families
(42:41) How COVID changed education
(47:41) Early prototypes and going all-in on Mentava
(50:56) Best practices from gaming in education
(55:10) Raising a party round from lots of angels
(01:03:03) Designing business models in education
(01:13:19) Being pro-tech + anti-screens for kids
(01:18:04) Top parenting hacks
(01:22:53) How data-driven product design leads to Frankenstein products
(01:25:34) Why gaming’s the best industry to learn how to build product
(01:27:46) The trick Niels used to find startup ideas for 20 years
(01:31:03) Why AI won’t be that impactful in education
(01:36:28) What happens to elite higher education over the next decade
(01:43:15) Admiring Stripe
Referenced:
Mentava: https://www.mentava.com/
Ryan Delk podcast episode: https://open.spotify.com/show/3QqtxGHqsPnKTG4CS7NgX5 | https://youtu.be/GTfsMEOIIxQ
How Neils raised Mentava’s Seed round: https://www.mentava.com/blog/how-i-got-50-high-profile-angel-investors-to-join-our-seed-round
Mentava’s Alphabet Book: https://www.mentava.com/alphabet-sounds-book | https://www.amazon.com/Mentavas-Alphabet-Sounds-Niels-Hoven/dp/B0DKTQ9FW4
Follow Niels:
X / Twitter: https://x.com/NielsHoven
LinkedIn: https://www.linkedin.com/in/nielshoven
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
How Nextdoor Grew to 100M Neighbors + Why Founding CEO Nirav Tolia Returned Six Years Later
Nirav Tolia is the co-founder and two-time CEO of Nextdoor. He started the company in 2011, stepped down as CEO in 2018, watched the company go public in 2021, and re-joined as CEO the summer of 2024. He also founded Epinions which IPO’d in 2004, and before that was an early employee at Yahoo.
We go inside the decision to re-join the company after he thought he’d never come back, and how Nextdoor’s trying to act like a startup while running a public company. He also takes us back to the very early days of Nextdoor, the deliberate product decisions that made growth hard but led to 100M+ neighbors on the platform, the lessons learned operating his first company through the Dot Com Bubble, and what it was like being a guest shark on Shark Tank.
For full show notes, visit: https://highlightai.com/share/d7bcd655-9b2f-47f7-a6e3-fdf3e109c97e
Recommended Podcast:
🎙️Unpack Pricing
Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more.
Apple: https://podcasts.apple.com/us/podcast/id1765716600
Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg
Timestamps:
(00:00) Intro
(02:39) Leaving Nextdoor in 2018
(07:30) Coming back in 2024
(10:31) The importance of family in career decisions
(17:37) Why you have to listen to learn
(24:47) The Founders Mentality
(26:45) “Develop and Deliver”
(32:03) Local, the last remaining consumer opportunity
(36:58) Why being a founder is so hard
(39:21) Going to the high school from Friday Night Lights
(42:07) What Nirav learned at Stanford
(46:22) Working at Yahoo from $500m to $100B
(49:37) Starting Epinions with Naval in 1999
(51:11) Operating through the Dot Com Bubble
(56:34) How Bill Gurley’s challenge led to Nextdoor
(58:16) Early product experimentation
(01:05:19) Why early growth was so hard, and scaling to 100 million neighbors
(01:10:10) The opportunity in local news
(01:12:14) Being a Shark on Shark Tank
Referenced:
Nextdoor: https://nextdoor.com/
The Founder’s Mentality: https://www.amazon.com/Founders-Mentality-Overcome-Predictable-Crises/dp/1633691160
Follow Nirav:
Twitter: https://x.com/niravtolia
LinkedIn: https://www.linkedin.com/in/niravtolia
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to get new episodes + transcript in your inbox every week: https://www.thespl.it/
Recruiting From Zero to One with Nakul Mandan, Co-founder of Audacious Ventures
Nakul Mandan is the founder of Audacious Ventures. Prior to Audacious, he was a partner at Lightspeed, joining from Battery, which he joined in ‘09 in the middle of the financial crisis while living in India.
This conversation explores his journey immigrating to Silicon Valley and building an early stage venture firm from the ground up.
We get into why most VCs aren’t helpful with recruiting at the zero to one stage, his thesis on starting an early stage venture firm to help founders hire A+ teams, a crash course on early stage recruiting and building a sales team, and how COVID hit right after he left Lightspeed to raise Audacious Fund 1.
Timestamps:
(00:00) Intro
(03:43) Evolution of VC platform teams
(09:53) How Audacious runs in-house recruiting processes
(15:16) The reason large firms can’t help with Seed stage recruiting
(17:06) Immigrating from India to the US mid-financial crisis
(21:59) Silicon Valley's secret weapon
(25:59) The opportunity to start a recruiting-focused Seed firm
(30:14) Raising Audacious $90m Fund 1 in April of 2020
(36:58) The new guard of Seed firms
(39:23) Why $50-75m is the minimum viable institutional fund size
(41:48) How to work with the best founders
(45:30) Navigating deal dynamics, term sheets, and valuations
(52:24) The two hardest parts about starting your own fund
(54:32) Lessons applied raising Audacious $125m Fund 2 in 2023
(58:46) Evolving from a PMF-first to Founder-first investor
(01:02:09) Five traits of force of nature founders
(01:07:05) How to build an A+ team
(01:11:46) The importance of backchanneling
(01:13:54) Why everyone thinks they’re a good people reader
(01:14:35) Two most common mistakes in recruiting
(01:20:59) Determining urgency of a customer’s problem
(01:22:55) Hiring and scaling your first sales team
(01:25:55) Why marketing is the hardest role to hire for
(01:31:59) What good sales people look like
(01:35:43) How to move up market + how to do pilots
(01:43:40) Why Nakul admires Rafael Nadal
Referenced:
Audacious: https://www.audacious.co/
Nakul’s immigration journey: https://www.nakulmandan.com/blog/2024/an-immigrant-living-the-american-dream
Force of nature founders: https://www.nakulmandan.com/blog/2024/traits-i-look-for-in-founders
Early GTM hiring: https://www.nakulmandan.com/blog/2023/initial-gtm-hiring-for-saas-startups
Follow Nakul:
Twitter: https://x.com/nakul
LinkedIn: https://www.linkedin.com/in/nakulmandan
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it
Inside Rent the Runway’s Early Days and the Future of Commerce with Co-founder Jenny Fleiss
Jenny Fleiss is the Co-founder of Rent the Runway, and more recently started Roll Rider with her three kids.
We get into the early insights that led to Rent the Runway, building the company with no fashion or tech background, fundraising advice, what she’s thinking about the future of AI and commerce, and the latest company she’s building with her kids, Roll Rider.
For full show notes, visit: https://highlightai.com/share/9bc59c07-05ab-41aa-b37e-f35a7c92092d
Timestamps:
(00:00) Intro
(05:31) How social media was Rent the Runway’s first tailwind
(07:21) Being early to sustainable fashion
(09:21) Starting the company at HBS in 2008
(12:36) Launching with no fashion or tech background
(14:49) The three biggest early surprises
(18:44) Using “show don’t tell” to fundraise
(20:06) Why customer social proof was so important
(23:04) Spending only 10% of revenue on marketing
(25:12) Getting the NYT to cover their launch
(29:43) Early mistakes
(31:29) Re-building the product a few weeks before launch
(33:11) Why building their own logistics was so important
(38:59) Subscriptions, retail, and other key product decisions
(45:15) How the internet makes it harder to shop
(49:30) Building conversational commerce at Walmart
(53:48) Lessons from starting a company with her kids
(58:38) Favorite startups in AI and commerce
Referenced:
Rent the Runway: https://www.renttherunway.com/
NYT’s Launch Coverage: https://www.nytimes.com/2009/11/09/technology/09runway.html
Check out Roll Rider: https://rollrider.com/
Use code TURNER15 for 15% off
Follow Jenny:
Twitter: https://x.com/Jenny_RTR
LinkedIn: https://www.linkedin.com/in/jennifer-fleiss-18577314
Follow Turner:
Twitter: https://x.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Startup Marketing Masterclass: How OpenPhone Grew to 100k Customers | Daryna Kulya
Daryna Kulya is the Co-founder of OpenPhone, the world’s best business phone
This episode is a masterclass on startup marketing, chronicling the first six years of OpenPhone, how they acquired their first customers, and inside all the different channels they used to scale the business to over 100k customers, including FB Groups, Reddit, SEO, and cold outbound.
We also get into why founder-led content is so important today, and why design is a crucial core competency.
For full show notes, visit: https://highlightai.com/share/28b95226-9936-4ae9-882d-6c68a1b578d5
Timestamps:
(00:00) Intro
(02:10) OpenPhone’s new API launch
(06:41) Why a better business phone is a big deal
(13:18) Immigrating from Ukraine to the US and building OpenPhone
(15:39) Hacking a custom business phone
(25:29) How OpenPhone got its first customers from Facebook Groups
(33:02) Tricks for unlocking word of mouth
(39:11) Transitioning from free to paid users
(43:05) How OpenPhone cracked word of mouth on Reddit
(46:29) OpenPhone’s YC experience
(49:01) Why the Seed round was hard to raise
(53:49) Using Slack to aggregate all customer feedback across the internet
(57:38) How YC helped redefine their ICP
(01:01:33) Tactics for sending cold emails
(01:06:24) How to get and benefit from press
(01:12:18) Daryna’s “behind the scenes” approach to founder-led content
(01:16:26) Using long-tail keywords to kickstart an SEO strategy in 2020
(01:23:05) When to do founder-led content vs SEO
(01:28:38) How your customers should pull you up-market
(01:30:18) Why OpenPhone cares about design
Referenced:
OpenPhone: https://openphone.com/ Ahrefs: https://ahrefs.com/
Follow Daryna: Twitter: https://twitter.com/darynakulya LinkedIn: https://www.linkedin.com/in/darynakulya
Follow Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Beating the Market 15 Years in a Row, Lessons from Jeff Bezos | Lisa Rapuano
Lisa Rapuano outperformed the market 15 years in a row in the 90’s and 2000’s. We go deep on how she did it, including early investments in AOL, Dell, and owning 24% of Amazon in 2002.
She shares what she learned from Jeff Bezos and Michael Dell, what makes a good investor, plus her experience as a startup CFO and how it influenced how she thinks about investing.
For full show notes, visit: https://highlightai.com/share/883f2cc9-9771-4331-9a42-6ae236f50344
Timestamps: (00:00) Intro (03:18) Growing up middle class while dad worked at NASA (12:31) Moving to Baltimore to work for Bill Miller (18:12) What Lisa learned from Bill (19:41) How value investing changed over the last 30 years (26:40) Investing in internet stocks in the 90’s and 00’s (29:50) Thinking a 13x win on AOL in 1996 would be the biggest of her career (37:33) Teaching Barry Diller about the internet (41:30) How Dell reinvented PC manufacturing and created a negative cash conversion cycle (46:46) How Amazon survived the Dot Com Crash (51:53) Buying 24% of Amazon in 2002 (53:15) Why companies get the investors they deserve (57:22) What Lisa learned from Jeff Bezos (1:04:31) Lessons from raising too much money (1:07:57) Running her own fund from 2006-2016 (1:13:32) Why fees in asset management are too high (1:15:20) Joining Facet out of retirement 2017 (1:20:20) What she learned about investing from operating (1:23:47) Why women are better investors than men (1:26:43) How to hire outlier candidates (1:35:06) Why no one can be the next Warren Buffett (1:39:54) When to sell your winners
Follow Lisa:
LinkedIn: https://www.linkedin.com/in/lisa-rapuano/
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Gokul Rajaram | Lessons from Zuck, Jack Dorsey, Sergey Brin + Defining your ICP, Evolution of Seed Investing
Gokul Rajaram is an early stage technology investor. As a product leader, operator and board member, he’s helped build seven generational technology companies, including Alphabet, Block, Coinbase, DoorDash, Meta, Pinterest, and The Trade Desk.
We talk about lessons learned from Zuck, Sergey Brin, and Jack Dorsey, when big acquisitions can go well, how to define your ICP, why you should always size markets bottoms-up, having a fast response time, how seed investing has changed since 2007, and Gokul’s hot takes on titles at a startup.
Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at https://bit.ly/WorkOS-Turpentine-Network.
Timestamps:
(00:00) Intro
(02:14) Common thread of success between the founders of Google, DoorDash, Facebook, and Square
(05:50) Gokul’s first job in Silicon Valley
(07:46) How Serendipity led to PMing Adsense, one of Google’s biggest products
(12:20) Lesson from Sergey Brin on reducing friction before a products magic moment
(18:50) How Zuck used founder mode to beat Google Plus in 2011
(22:51) When big acquisitions can go well
(24:47) How Gokul switches from startup helper to public company board member
(28:09) The evolution of Seed investing since 2007
(33:27) How to have a fast response time
(37:40) Lessons from Jack Dorsey always selling
(39:54) How to define your ICP
(42:40) Using bottoms-up to size a market
(44:05) Why Director and VP titles are bad for startups
Referenced:
Who’s Got the Monkey? https://hbr.org/1999/11/management-time-whos-got-the-monkey
Getting Things Done: The Art of Stress-Free Productivity https://www.amazon.com/Getting-Things-Done-Stress-Free-Productivity/dp/0142000280
How to Size a Market in 30 Minutes https://blog.blingcap.com/2023/02/13/How-to-Size-a-Market/
Follow Gokul:
Twitter: https://x.com/gokulr
LinkedIn: https://www.linkedin.com/in/gokulrajaram1
Follow Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
How to Build in AI, Lessons From Early Days of Snyk with Founder Guy Podjarny
Guy Podjarny is the founder of Blaze, Snyk, and now Tessl. He’s spent decades building at the center of developers and security. His newest company Tessl is reimagining software development, helping shape a new paradigm he calls AI Native Development.
We talk through his four quadrant framework for building and investing in AI, plus go into the early days of Blaze and Snyk. He shares lessons on marketing to developers, hiring when no one wanted to work for him, overcoming multiple difficult funding rounds, and lessons from multiple M&A processes.
Timestamps:
(00:00) Intro
(02:21) The four quadrants of building and investing in AI
(14:59) Why AI startups are riskier than non-AI startups
(19:42) When to sell your company vs keep building
(24:57) Why hiring the early team is so hard
(26:32) Early marketing tricks from Guy’s first company, Blaze
(29:09) Strategies for using conferences to grow your brand
(33:33) Getting three days of free PR
(38:04) Moving to Ottawa
(42:11) Why Sales Engineer is an underrated founder stepping stone
(45:49) What he learned as CTO of Akamai
(48:31) Starting his third company Tessel, and why there’s no satisfaction without struggle
(50:41) How Snyk got started
(54:10) Creating developer-first security
(59:59) Secrets for developer marketing
(01:02:31) Why podcasts work so well for marketing
(01:06:26) Snyk’s failed Series A
Referenced
Tessl: https://tessl.io/
Snyk: https://snyk.io/
Charting Your AI Native Journey: https://www.tessl.io/blog/charting-your-ai-native-journey
Secure Developer Podcast: https://snyk.io/podcasts/the-secure-developer/
AI Native Dev Podcast: https://www.tessl.io/podcast
We didn’t mention it in the podcast, but Guy just announced the AI Native Dev Conference, a virtual conference on Thurs, November 21st. Join him + many others here https://ai-native-devcon.heysummit.com/
Follow Guy
Twitter: https://x.com/guypod
LinkedIn: https://uk.linkedin.com/in/guypo
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
The Rise of AI-Powered Services + Ultimate Sales Crash Course for Founders | Chris Hladczuk, Hanover
Chris Hladczuk is the Co-founder and CEO of Hanover, where he’s building 1-click migration and 1-minute time to value fund administration for the $8 trillion in private market assets.
Chris takes us through his story of building an audience online at nights while working at Goldman, breaking into tech and going from an IC to Chief Revenue Officer at a Series A startup in nine months.
This episode is packed with advice on sales, getting your first startup role, and everything he’s up to at Hanover.
Timestamps
(00:00) Intro
(02:11) Why B2B SaaS is dead
(07:20) Competing against companies that have “IT departments”
(11:37) Going from 0 to 100k on Twitter in one year
(19:06) The ASS networking framework
(25:17) Interviewing at 50 startups before quitting Goldman to join Meow
(28:41) Lessons going from sales IC to Chief Revenue Officer in nine months
(32:47) Using SSS to send good cold emails
(35:51) Learnings as a first-time manager
(40:46) How to make a good first impression
(47:22) Why sales and copywriting are underrated
(49:17) Navigating the startup idea maze to fund admin
(56:47) 1-click fund admin migration, 1-minute time to value
(59:46) Turning down Hanover’s first term sheet with no backup plan
(01:03:28) Using polite persistence to get customers
(01:08:41) Why the best companies are cults
(01:11:01) John D Rockefeller and vertical integration
(01:13:26) Doing culture fit questions at the beginning of the hiring process
(01:15:34) Chris’ favorite AI tools
(01:17:58) How to make founder-led content
Referenced
Check out Hanover: https://www.hanover.co/
Brick: https://getbrick.app/
Alex Hormozi’s Sales Podcast: https://open.spotify.com/show/6YNopzKDGDwf0auIpPTIID
Sweetgreen: https://www.sweetgreen.com/
Chipotle: https://www.chipotle.com/
Eight Sleep: https://www.eightsleep.com/
Turner’s episode with Jonathan Neman at Sweetgreen: https://open.spotify.com/episode/1Emm6VOq6MCEfQlXv05q6U?si=hJMc8LhBTeeonYJGza4gxQ
The Hanover Manifesto: https://www.hanover.co/manifesto
Claude Sonet: https://claude.ai/
Cursor: https://www.cursor.com/
Hemingway Editor: https://www.hemingwayapp.com
Follow Chris
Twitter: https://twitter.com/chrishlad
LinkedIn: https://www.linkedin.com/in/chris-hladczuk-b09204153
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
Lessons Building Five Unicorns + Building Pathlight Ventures | Charley Ma & Mahdi Raza
Charley Ma and Mahdi Raza are the Co-founders of Pathlight Ventures, and were early employees at five unicorns, Plaid, Ramp, Alloy, Robinhood, and Stytch.
They share tactical advice for early stage startup employees, lessons getting Plaid and Ramp their first customers, and deciding to build Pathlight together.
Timestamps
(00:00) Intro
(02:30) Growing up in basements
(05:15) Charley’s journey to first biz hire at Plaid
(15:01) Advice on being a good startup employee
(19:34) Mahdi’s path to Robinhood
(26:33) Deciding between joining an early or late stage startup
(32:39) Why Charley joined Plaid despite VCs telling him not to
(38:52) Benefits of case studies in hiring
(39:58) Why every hyper growth company is a shit show
(44:24) Startup comp: equity, QSBS, early exercise, vesting
(49:59) Joining Ramp as the first Head of Growth
(58:35) How Ramp got its first customers
(01:02:06) Advice and common traps on early GTM strategies
(01:05:04) Why $1M ARR does not mean you have PMF
(01:06:51) Meeting when Robinhood bought, churned, then returned to Plaid
(01:09:54) Deciding to build Pathlight together
(01:23:06) Raising Fund 1 in 2021 and how bad timing almost killed it
(01:29:55) Reasons founders work with Pathlight
(01:32:04) Why most investors add no value and give bad advice
(01:36:44) Founders Pathlight invests in + Artie case study
(01:44:44) Competing with incumbent funds
(01:53:57) Raising a $75m Fund 2 in 2023
(02:02:22) Are Seed extensions good investments?
(02:07:45) Discussing startup valuations
(02:09:09) Mahdi’s 10-minute market outlook (as of 8/8/24)
Referenced
https://www.pathlight.vc/
https://plaid.com/
https://robinhood.com/us/en/
https://ramp.com/
https://stytch.com/
https://www.alloy.com/
https://www.artie.com/
Follow Charley
Twitter: https://twitter.com/charleyma
LinkedIn: https://www.linkedin.com/in/charleyma
Follow Mahdi
Twitter: https://twitter.com/mahdirazamr
LinkedIn: https://www.linkedin.com/in/mahdirazany
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
How ClickUp Bootstrapped to $10m ARR and Scaled to 9-figures in Revenue with Zeb Evans
Building an enterprise-ready SaaS app? WorkOS has got you covered with easy-to-integrate APIs for SAML, SCIM, and more. Start now at https://bit.ly/WorkOS-Turpentine-Network.
He’s had six near death experiences, and we talk about how those influenced him throughout life. We also talk about some of his early businesses, including one that had the FBI at his house when he was a kid, and lessons driving the monorail at Disney.
We also get into the founding story of ClickUp, bootstrapping to $10m in ARR, hiring mistakes from scaling too fast, why Zeb likes hiring users, how ClickUp shipped generative AI features so fast, its new chat product launched earlier this week, and the trend of software convergence.
Timestamps:
(00:00) Intro
(02:11) Zeb’s first near death experience
(08:19) Childhood businesses that had the FBI at his house
(18:23) Lessons from driving the monorail at Disney
(25:19) Mistakes scaling from 100 to 800 employees in one year
(31:04) Dropping out of college after being robbed at gunpoint
(33:19) How building a CraigsList competitor led to ClickUp
(35:32) Three waves of ClickUp’s product evolution
(39:25) How the product slowly got worse over time
(44:45) Hiring the guy who built Microsoft Teams to rebuild ClickUp
(48:11) Zeb’s favorite interview question
(49:59) Daily 5am standups in the first year
(54:28) How ClickUp got its first customers
(57:16) Bootstrapping to $10m in ARR with strong retention
(58:13) Zeb’s best kept secret, user surveys (and how to run them)
(1:02:42) The trend of software convergence
(1:08:26) Reasons Zeb likes hiring users
(1:12:19) Why VCs didn’t invest, and why it led to a better business
(1:19:02) Raising from Craft, Georgian, and a16z
(1:21:08) Peter Thiel: “I think you’re right”
(1:24:35) How ClickUp was early to AI
(1:28:03) Launching chat and video calls to hit ClickUp's original vision
(1:32:02) What Zeb’s excited and cautious about in AI
(1:37:24) Why Zeb journals every day
Referenced:
ClickUp: https://www.clickup.com
ClickUp’s new chat feature: https://clickup.com/features/chat
Follow Zeb
Twitter: https://x.com/dj_curfew
LinkedIn: https://www.linkedin.com/in/zebevansclickup
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
Teen Hacker to Founder, Building an Open Source Security Company | Bobby DeSimone, CEO of Pomerium
Bobby DeSimone is the Founder and CEO of Pomerium, the best way to authenticate, authorize, monitor, and secure user access to any application without a VPN.
Bobby explains why access control is so important, how it led to the biggest corporate hack ever, how its related to the day CrowdStrike took down the global economy, and how AI will change security.
Pomerium has a unique open source approach, and Bobby takes us inside the early days of building the product, how he got the first customers, lessons learning enterprise sales as a technical founder, and inside his funding rounds, including a recent Series A led by Eric Vishria at Benchmark.
Timestamps
(00:00) Intro
(02:02) Access Control: a sneaky large problem
(07:22) How an unsecure air conditioner led to the biggest credit card breach in history
(10:23) Google’s internal security software inspiring Pomerium
(16:41) Making his first money online selling a WoW bot
(19:24) How CrowdStrike took down the global economy in July, 2024
(22:29) Deep dive on access control and security
(29:39) How access controls impacted Google vs Uber’s self-driving lawsuit
(30:52) Why Zero Trust security is marketing bullshit
(32:09) Advice for building access control
(34:39) How open source built early trust with customers
(41:39) Missing a 7-figure deal because he didn’t use LinkedIn
(44:52) Everything he’s learned about sales as a technical founder
(50:06) Inside Pomerium’s Series A
(51:41) Advice on evaluating potential investors
(56:06) How AI will change security
(01:01:15) Getting in trouble at the first Pomerium board meeting
(01:02:15) How to hire good engineers
(01:04:00) When to scale back IC work as a founder
(01:06:56) Favorite new AI tools
(01:11:09) Why Meta’s open sourcing its AI models
(01:12:32) Life lessons from Charlie Munger
Referenced
Check out Pomerium: https://www.pomerium.com/
Crowdstrike outage post-mortem: https://www.crowdstrike.com/falcon-content-update-remediation-and-guidance-hub/
Pomerium on GitHub: https://github.com/pomerium/pomerium
Follow Bobby
Twitter: https://x.com/bdd_io
LinkedIn: https://www.linkedin.com/in/bobby-desimone/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
Inside the beehiiv Playbook with Tyler Denk, Co-founder and CEO
Tyler Denk is the Co-founder and CEO of beehiiv, the newsletter platform built for growth.
We go inside beehiiv’s early days, including joining MorningBrew as the second employee, lessons scaling to 3.5 million subscribers, the $75 million sale to Business Insider, and why I didn’t invest in beehiiv despite being an early customer.
Tyler takes us inside the playbook that grew to $1.5m in monthly revenue in less than three years, including how they first positioned the product in a crowded market, how beehiiv ships so fast, when a co-founder passing away less than one year into building the business, and the day GoDaddy took the entire beehiiv platform offline for 8 hours.
Timestamps
(00:00) Intro
(01:36) Why Turner didn’t invest in beehiiv (twice)
(03:04) Joining MorningBrew as the first employee
(15:28) Why newsletters are so powerful
(19:40) Scaling MorningBrew to 3.5 million subscribers and exiting to Business Insider
(23:14) Difference between startups and big companies
(26:26) Why beehiiv has two days of no meetings
(27:53) The initial insight to start beehiiv
(35:39) Building a programmatic newsletter ad marketplace
(39:52) Dissecting beehiiv’s nearly $20m rev run rate business model
(45:21) Inside beehiiv’s first funding round
(46:58) Where Turner’s reference check went wrong
(50:45) Litquidity and beehiiv’s initial product positioning
(52:59) How beehiiv builds in public
(57:41) Banning meetings two days per week
(01:00:13) Why the best remote teams always beat in-person
(01:06:19) The impact of a co-founder dying one year into the business
(01:11:50) Raising a Series A despite operating at breakeven
(01:16:14) Why Tyler writes public investor updates
(01:21:04) Moving fast, and “why perfect kills all momentum”
(01:26:03) When GoDaddy took beehiiv down for 8 hours
(01:29:57) Why Tyler writes a newsletter
(01:32:21) His Big Desk Energy Spotify playlist
(01:36:08) Why you never regret firing bad hires
(01:39:53) Looking up to Elon and Brian Chesky
(01:41:34) Monk mode in Columbia
Referenced
The Power of Investor Updates: https://mail.bigdeskenergy.com/p/power-investor-updates
beehiiv’s old investor updates: https://mail.bigdeskenergy.com/c/beehiiv-investor-journey
The BDE Spotify Playlist: https://open.spotify.com/playlist/5s8443tfYUq3LLARJwGeYP
Where to find Tyler
Twitter: https://twitter.com/denk_tweets
LinkedIn: https://www.linkedin.com/in/tyler-denk
Newsletter: https://mail.bigdeskenergy.com
Where to find Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it
The Future of Software, AI, and Tax, Lessons Scaling Zero to One | Michelle Valentine, CEO of Anrok
Michelle Valentine is the Co-founder and CEO of Anrok, the sales tax platform for software companies.
We talked trends in software consolidation, lessons working with Anrok’s first customers, advice on fundraising, scaling a sales team, and early tricks for founders to avoid future tax-related headaches.
Timestamps
(00:00) Intro (02:19) The trend of software consolidation (03:00) Why billings and payments isn’t consolidating (06:09) Early tricks for avoiding future tax headaches (08:42) Founder lessons from first being a VC (09:28) The two catalysts that led to Anrok (17:15) How software companies used to figure out sales tax (22:51) Raising Anrok’s Seed round in 48 hours (25:42) How to join a VC's scout program (28:24) Fundraising lessons from being an investor (34:24) Surprising results from the very first “easy file” product (38:30) Lessons getting the first customers from outbound (40:19) Why you should make your first two sales hires at the same time (41:50) Sales advice when scaling into enterprise customers (46:19) How your Seed round helps raise your A and B (47:24) The reason AI and LLMs are so hard to predict (50:58) Michelle’s favorite Claude use cases (53:51) Predicting market sizes, and why Figma’s seemed small (57:39) How to invest in AI right now (1:01:01) Advice on changing your opinion (1:04:10) Getting outside your comfort zone (1:05:04) Michelle’s go-to interview question (1:34:50) The most ridiculous SPACs (1:07:23) Lessons from Scott Cook, the founder of Intuit
Referenced Check out Anrok: https://bit.ly/3YTb0ED Anrok’s Journal Entries Newsletter: https://bit.ly/3AxrtUV Anrok Mid-year SaaS Sales Tax Review: https://www.anrok.com/resources/mid-year-saas-sales-tax-review-2024 Michelle’s Article on AI, Part 1: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-one-michelle-valentine Part 2: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-two-michelle-valentine Part 3: https://www.linkedin.com/pulse/fog-ai-what-investors-missing-part-three-michelle-valentine Superintelligence: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/1501227742
Where to find Michelle: Twitter: https://twitter.com/_vltn LinkedIn: https://www.linkedin.com/in/michellevalentinehk/
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
ShipHero’s Journey to $12B | Aaron Rubin, Founder and CEO
Inside the Logan Bartlett Show, Investing Through Market Cycles + Bubbles, Dissecting VC Frameworks
Logan Bartlett is a Managing Director at Redpoint.
If you like startups and you listen to podcasts, you’re probably familiar with his podcast, the Logan Bartlett Show. We talk about how it first got started, plus all his tricks for growing the podcast, including his canonical episodes in 2022 that helped pop the web3 bubble.
We also talk market cycles and bubbles, and what Logan’s seeing in the data today, especially in AI, plus Logan’s philosophy’s on venture capital as an asset class, his favorite under the radar investors, and advice for his younger self.
Timestamps: (00:00) Intro (01:33) Not getting invited to Michael Rubin’s white party (04:29) Meeting on Twitter during COVID (11:09) How Logan and I benefited from Twitter (16:55) Early days of the Logan Bartlett Show (22:10) Why podcasts are so hard to grow, and how Logan did it (24:50) Learning YouTube’s the best for podcast growth (29:51) Inside Logan’s web3 episodes with Zach Weinberg (32:07) Lessons from studying history and market cycles (33:15) Producer Ben fact checking Logan's historical railroad statistics (39:42) How to invest in and around bubbles (51:00) Market data from Redpoint’s 2024 AGM update (55:12) Differences between companies valued at 100x and 5x ARR (1:00:04) The Barbell Theory of asset management and why Logan disagrees it will happen in VC (1:09:40) Ways VCs can actually add value (1:12:27) Redpoint’s founding story + greatest hits (1:18:14) The most underrated investors and founders (1:21:35) Advice for young people: pick a niche, go deep, stay focused
If you enjoy this conversation and you’re not already, make sure to like, comment, follow, and subscribe to my newsletter in the show notes to get future episodes in your inbox every week.
Referenced: Clearspace https://www.getclearspace.com/ Acquired’s TikTok episode https://www.acquired.fm/episodes/tiktok Gorilla Game https://www.amazon.com/Gorilla-Game-Picking-Winners-Technology/dp/0887309577 Redpoint’s AGM Update https://docs.google.com/presentation/d/1T3kGf-n4cmd6_UqOQNb79ZXFL723b9HdZyTnk9sLOlM/edit
Where to find Logan: Twitter: https://x.com/loganbartlett LinkedIn: https://www.linkedin.com/in/loganbartlett/
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Lessons From Two Exits + Building Electric to Automate IT Management | Ryan Denehy
Ryan Denehy is the founder and CEO of Electric, software that helps businesses manage their IT and IT support.
We talk through his first two startups from founding to exit, the early days of getting Electric off the ground, and Ryan’s frameworks for fundraising, recruiting, and sales.
Timestamps: (00:00) Intro (03:05) Building an ad network for extreme sports websites (11:07) Why a better pipeline solves all problems (13:24) Ryan’s trick for hiring executives (17:00) Selling the ad network to USA Today (18:11) Moving to SF to start a software company (21:33) Getting rid of his car to extend runway (24:23) Paying rent with credit cards (29:17) Struggling to raise a Series A (31:55) Using channel sales to grow the business (37:05) Almost running out of money before selling to Groupon (43:37) How cloud created the perfect timing to build Electric (48:33) Leveraging software and AI to automate manual human tasks (51:45) Why you should avoid buzzwords in marketing (53:57) Pros and cons of being a solo founder (56:14) Why Electric built a large initial board (01:02:41) Advice for picking lead investors (01:06:35) How VC fund dynamics have inflated Seed rounds (01:09:16) The downsides of high valuations (01:12:45) Almost wiring back the Seed round (01:16:37) Why every fundraise is a Pipeline problem (01:21:04) The reasons VCs actually pass on founders (01:26:42) Cutting the burn rate in 2022
Electric.ai: https://www.electric.ai/
Where to find Ryan: Twitter: https://twitter.com/DenehyXXL LinkedIn: https://www.linkedin.com/in/ryandenehy/
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Frank Rotman | Building Capital One ($58B) and QED Investors ($4B AUM)
Car Dealership Guy: From Anonymous VC-Backed CEO to B2B Media with Yossi Levi
Warp: Don’t let payroll and compliance hold your startup back: visit https://www.joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll.
Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.
Yossi Levi shares his incredible story: transforming a small family car lot into a $28 million dollar powerhouse, founding venture-backed Gettacar and growing it to $90 million in revenue, before returning the capital to investors and growing his anonymous Twitter account into Car Dealership Guy, a B2B automotive media empire.
Yossi takes us inside his early marketing strategies, the hard earned lessons from chasing product-market fit, and the playbook to building a lean, scalable B2B media machine.
Timestamps: (00:00) Intro (07:26) Helping at his dad’s used car lot (11:22) How car dealerships make money (14:32) $28m revenue with Facebook ads (17:48) Putting gifts in customer trunks and filming it (22:58) Starting Gettacar to sell cars online (25:04) When a VC pulled his first term sheet (31:08) Recruiting full-time hires with part-time consulting gigs (34:45) Personally guaranteeing the debt used to finance vehicles (36:50) Helping subprime consumers buy cars online (39:24) How 2021 tricked them into thinking they had a sustainable business (41:57) Why you can’t rush Product Market Fit (42:23) Pivoting Gettacar to a profitable, PE-backed business before winding it down (47:22) Starting an anonymous Twitter to share insights from his day-to-day (50:08) Turning Car Dealership Guy into a media business (53:38) Doxing himself with a 13-minute documentary (58:29) Why you have to consume to be a good creator (1:00:04) Screensharing CDGs content schedule (1:02:59) Why every employee needs to generate content or revenue (1:09:27) Creating a car / auto influencer agency (1:11:34) Building a B2B automotive ad network (1:14:50) Evolving into a holding company (1:20:27) Importance of moving fast (1:23:34) Why people actually like sponsored content (1:28:08) Wishing he pivoted to B2B faster
More on Car Dealership Guy: https://www.dealershipguy.com/
Referenced Who the F*ck is Car Dealership Guy: https://www.youtube.com/watch?v=_wTsAez_nMs Russ Flips Whips: https://russ.dealershipguy.com/ Freight Waves’ Craig Fuller on The Peel: https://youtu.be/oPPqO8eBq2M Epic Gardening’s Kevin Espiritu on The Peel: https://youtu.be/FefGL-qPzDo
Where to find Yossi: Twitter: https://twitter.com/GuyDealership YouTube: https://www.youtube.com/@CarDealershipGuy
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
The 26-Year Old Exposing $10B Public Companies | Edwin Dorsey, The Bear Cave
Warp: Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1,000 gift card when you first run payroll.
Get first-party targeting with Brave's private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.
Edwin Dorsey is the author of The Bear Cave, a weekly newsletter exposing publicly traded companies that are misleading investors and harming customers.
I’ve enjoyed Edwin’s writing since he launched his newsletter the Bear Cave in 2020, and he shares his best kept secret for doing customer research: FOIA requests. We also get into short selling more broadly, common corporate red flags, the economics of his media business, almost getting kicked out of Stanford for raising issues at Care.com his sophomore year, Planet Fitness’s illegal billing operation, Hershey’s Mr. Beast problem, and the creator economy more broadly.
(00:00) Intro (05:11) How shorting works (07:20) How short sellers exposed Enron (10:51) Edwin’s process for finding bad companies (15:52) Root Insurance and aggressive pricing (20:14) FOIA: the best kept secret for company research (24:30) Biggest corporate red flags (28:17) Most common industries for bad actors (29:32) Why scammers target minorities and low income consumers (31:46) Edwin’s $1B to $10B market cap sweet spot (34:03) The challenges of mainstream media (38:15) Exposing Care.com as a student at Stanford (45:25) Why immediate board resignations are a red flag (49:45) Launching The Bear Cave in Feb 2020 (49:37) Using podcast appearances to grow (56:06) The newsletter's business model (1:00:00) Experimenting with side-newsletters, job boards, and consumer surveys (1:10:04) Planet Fitness: gym or illegal billing operation? (1:18:45) Herbalife the pyramid scheme (1:21:05) Hershey’s MrBeast problem (1:28:15) Marketing and social signaling in CPG products (1:30:47) AgEagle Aerial Systems: $4B market cap, zero revenue (1:34:50) The most ridiculous SPACs (1:41:06) How Edwin differentiates his research (1:47:07) Favorite short sellers (1:47:59) Companies that will lose to AI (01:49:29) Why creator-led business will steal share from incumbents
Referenced The Bear Cave: https://thebearcave.substack.com/ FOIA Request Template (#13 here): https://www.readideabrunch.com/p/our-2023-hedge-fund-analyst-christmas SEC Full Text Search: https://www.sec.gov/edgar/search/ WSJ’s Care.com Story: https://www.wsj.com/articles/care-com-puts-onus-on-families-to-check-caregivers-backgroundswith-sometimes-tragic-outcomes-11552088138 Planet Fitness CEO resignation letter: https://x.com/StockJabber/status/1762220603715596460 Aurelius Value: https://x.com/AureliusValue Big River Capital: https://x.com/BigRiverCapita1 Marc Cahodes: https://x.com/AlderLaneEggs David Orr: https://x.com/orrdavid Citron Research: https://x.com/CitronResearch
Where to find Edwin: Twitter: https://twitter.com/StockJabber LinkedIn: https://www.linkedin.com/in/edwin-dorsey-a9195273/
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Silicon Valley's Secret 4-Week Visa with Lisa Wehden at Plymouth Street
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Lisa Wehden is the Founder and CEO of Plymouth Street, making fast and simple immigration for technologists. We go deep on the broken US immigration system, how its holding back US innovation, and the secret 0-1A Visa you can get in as fast as four weeks.
Lisa lived in a sawmill while building her first climate tech startup, and we go inside that journey, giving the VC money she raised back to start Plymouth, raising grants to fund it, and how she broke into Silicon Valley as an outsider.
Timestamps:
(00:00) Intro (04:51) The state of US immigration (09:26) Why immigrants are good founders (11:43) The secret O-1A Visa (12:18) Why the O-1A is easier to get (16:54) Founders that have gotten their O-1A (20:00) Getting a Visa in four weeks with Plymouth (22:01) The 500-page, physical paper Visa application (25:57) Lisa’s US immigration COVID hobby (27:58) Living in a Sawmill building a climate tech startup (30:59) Giving VCs their money back (32:19) Joining Interact in SF (33:51) Raising grant money instead of VC (34:40) Becoming a paralegal to learn the industry (37:24) The Plymouth 100 community (39:20) How Lisa raised grant funding from Eric Schmidt and Tyler Cowen (43:55) Talent is the bottleneck to AI development (46:04) How to break into Silicon Valley as an outsider (52:43) Hiring on hopes and fears (55:31) "Write it down, make it happen" (56:45) Benefits of doing a calendar audit (1:01:54) Anyone can be an entrepreneur (1:04:53) Why Lisa doesn’t work from her phone (1:06:38) How to fix the US immigration system
More on Plymouth Street: https://www.plymouthstreet.com/
Referenced:
Interact: https://joininteract.com
Lisa’s 0-1 Visa Guide: https://lisa-wehden.medium.com/a-guide-to-applying-for-the-o-1-visa-for-extraordinary-individuals-8ca5f22ff86b
Writing a forwardable email intro: https://also.roybahat.com/introductions-and-the-forward-intro-email-14e2827716a1
Where to find Lisa:
Twitter: https://twitter.com/lisawehden
LinkedIn: https://www.linkedin.com/in/lisa-wehden-aa111385/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Building Non-Addictive Apps for Kids | Melissa Cash, Pok Pok
Building boldstart ventures from $1M to $850M with Ed Sim
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Ed Sim is the Founder of boldstart ventures, which partners with bold founders reinventing the enterprise stack at the inception stage. Ed takes us inside the journey building boldstart, from its first $1m fund in 2010 up to $850m in AUM today.
Timestamps: (00:00) Intro (03:48) Evolution of early stage investing(05:11) Inception stage investing (10:32) Backing bold founders reinventing the enterprise stack(11:20) Repeatable ways to build enterprise businesses (12:04) The 5 P’s of early stage investing (14:12) Backing Guy Podjarny and Snyk (18:18) Knowing when to follow-on (19:18) The 3 Ch's of a good board member (22:01) How Ed’s board role changes over time (24:20) Balancing founder friendly with returns (27:20) How to build customer relationships (30:24) Advice for closing customers (33:47) Creating the Seed category in 2009/10 (37:31) boldstart’s $1m Fund 1 (39:00) Why Ed didn’t join a large firm in 2012 (39:55) boldstart’s $16.5m Fund 2 (40:26) Why LPs passed on the first funds (43:11) Leading rounds in Kustomer, Snyk, BigID, and Blockdaemon in Fund 3 (47:09) Why $112m Fund 4 was the hardest to raise(50:52) Ed’s approach to LP fundraising (55:12) Inside Meta’s acquisition of Kustomer and sale back to the founders (59:52) Backing Rahul from Superhuman a 2nd time (01:00:52) The different GTM playbooks (01:02:20) Importance of contract size and time to close (01:05:07) Why AI makes security more important (01:06:11) When to switch from founder-led sales(01:07:46) Backing ProtectAI after a conference (01:08:28) Balancing between inbound and outbound sales (01:09:55) Winners and losers in AI (01:15:26) Building the boldstart team (01:25:19) Lessons being an interim CEO (01:27:15) How ZIRP pulled revenue forward (01:29:08) The death of high growth software (01:32:58) Identifying startup opportunities incumbents won’t crush (01:35:00) Second order effects of AI (01:36:46) Using "Intuitive TAM" to size new markets (01:38:04) Investing before there’s a market map (01:38:57) Balancing family, fitness, and career
Referenced:
https://boldstart.vc/
Turning Down HBS: https://x.com/edsim/status/1315644287007240193
Ed’s tweet on raising Fund 4: https://x.com/edsim/status/1315644287007240193
Second Order Effects of AI: https://www.whatshotit.vc/p/whats-in-enterprise-itvc-379
Death of Hyper Growth: https://x.com/edsim/status/1797613384994623808
Where to find Ed:
Twitter: https://twitter.com/edsim
LinkedIn: https://www.linkedin.com/in/edsim/
Newsletter: https://www.whatshotit.vc/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Scaling Instacart to $10+ Billion with ex-President Nilam Ganenthiran
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Nilam Ganenthiran is the founder and CEO of Beacon Software. Previously, he was the 12th employee and President at Instacart.
We talk tactics for customer research, building customer relationships, balancing strategy and execution, how to serve on and manage a board, what happened when Amazon bought Instacart’s biggest customer Whole Foods, inside its COVID response, surviving eight months of runway in 2015, his new company Beacon Software, and more.
Timestamps:
(00:00) Intro (04:23) Inside Amazon acquiring Instacart’s biggest customer, Whole Foods (12:13) Lessons from quickly signing 8 of the top 10 grocers (13:06) Why grocers were slow to adopt ecommerce (15:29) Building “Shopify for grocers” (16:22) Sales = building relationships (19:05) Why Wegman’s is one of the best grocers in the world (20:43) Cold calling Wegman’s and signing them two years later (24:33) How to do customer research (26:59) Catching an Uber in suits on the highway (28:50) Why Instacart was possible back in 2013 (30:36) Launching Instacart’s advertising network (38:46) Growing 5x in 5 weeks during COVID (45:20) How Nilam started angel investing (47:56) Advice for sitting on boards (50:00) The roles and incentives of a board member (54:03) Deciding when to keep going and when to give up (56:02) Nilam’s framework around optionality (59:17) Seven years of weekly redeye flights (1:00:30) Almost running out of money 8 months after Instacart’s Series C (1:07:54) Why time is your scarcest resource & startups are default dead (1:10:00) Nilam’s new company, Beacon Software (1:11:28) Why he’s excited about AI (1:13:25) How AI makes human relationships more important (1:14:41) Turner’s investing lessons from family members
Beacon Software: https://beaconsoftware.ca/
Where to find Nilam:
Twitter: https://twitter.com/nilamg
LinkedIn: https://www.linkedin.com/in/nilamganenthiran/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
How the Smartest Companies Use AI | Ankur Goyal, Braintrust
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Ankur Goyal is the Founder and CEO of Braintrust, the end to end developer platform for building the world's best AI products. Their customers include companies like Instacart, Zapier, Notion, Airtable, Replit, and more.
We hit on the importance of LLM evals, advice for building AI products, why the best companies have two AI product roadmaps, and his non-conventional advice for founders.
Timestamps:
(00:00) Intro (04:04) Why everyone’s now an AI company (06:03) Reasons LLM evals are so important (08:10) Typescript becoming the language of AI (09:19) Replacing vibe checks with Braintrust (10:37) Making OpenAI’s protocols the standard (11:27) Why the best companies have two AI roadmaps (13:06) Building your product so each LLM release makes it better (14:54) Predicting AGI is impossible (15:54) Why people who work with LLMs aren’t worried about AI safety (16:52) The best developers are all-in on co-pilots (18:11) How AI is changing software development (21:09) Combining IDE, CIDC, and observability in one product (27:18) Are models more like CPU’s or relational databases? (30:14) How to pick an LLM (33:00) Advice for staying on top of new AI developments (34:30) Why tool calling is so important (38:02) Advice for young software engineers (40:25) Learning to code doing linear algebra homework (42:36) Lack of purpose interning in big tech (44:07) Working at MemSQL learning to be a founder (47:52) How to get a job at a startup (50:43) Building his first startups product on an international flight (52:39) Three lessons from his first failed startup (54:46) Don’t delegate what you’re good at (55:46) Why you should be careful listening to VCs advice (57:34) Tactics for successful delegation (59:36) Why Ankur doesn’t do any meetings (01:02:42) The importance of self-service in unlocking certain customer segments (01:05:14) How Braintrust got started (01:07:45) Advice on picking your target customers (01:10:35) How Braintrust hires with work trials (01:15:21) Balancing security with a modern UI (01:17:49) Why it’s hard to sell non-AI products right now (01:19:21) Advice for selling to large enterprises (01:23:10) Ankur’s favorite AI products
Referenced:
https://www.braintrustdata.com/
SICP Book
PDF: https://web.mit.edu/6.001/6.037/sicp.pdf
Hardcopy: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871
Linear’s guide to work trials: https://linear.app/blog/why-and-how-we-do-work-trials-at-linear
Where to find Ankur:
Twitter: https://twitter.com/ankrgyl
LinkedIn: https://www.linkedin.com/in/ankrgyl/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Lessons From 21 Years of VC Fund Investing | Alan Feld, Vintage Investment Partners
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeelAlan
Feld is the Founder and Managing Partner of Vintage Investment Partners. Vintage is one of the largest fund of funds in the world, managing over $4 billion across what is mostly investments into other venture funds, plus some secondary and direct startup investments at the growth stage.
Timestamps:
00:00 Intro 03:53 What is Vintage 05:40 Why VCs adding value can waste a founder’s time 09:01 VC, where the asset chooses the investor 10:14 Fund size is the enemy of returns in VC 14:57 What people get wrong about FoFs 16:01 The value FoFs bring to LPs 17:11 Why entrepreneurs drive VC returns 17:55 Vintage’s unique FoF model 19:05 Does replacing the founders with an outside CEO work? 21:39 Starting Vintage after the Dot Com Crash in 2002 23:41 Buying secondaries at 70-80% discounts 25:13 Biggest mistakes when buying secondaries 26:18 Research around what makes the best entrepreneurs 31:09 Lessons from six downturns 34:41 Comparisons between 2002 and 2022 37:07 Advice for raising your first VC fund 41:16 The importance of differentiation 45:57 Sustainable ways to differentiate 49:05 What Vintage looks for in new fund investments 49:57 Advice for scaling a VC firm 53:47 Succession planning 57:50 What Alan’s doing post-Vintage
Vintage Investment Partners: https://www.vintage-ip.com/
Where to find Alan:
Twitter: https://twitter.com/alanf_feld
LinkedIn: https://www.linkedin.com/in/alan-feld-1744389/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Fixing The Maternal Health Crisis with Anu Sharma at Millie
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Anu Sharma is the Co-founder and CEO of Millie, building a better care system from the inside out. Our conversation covers the existing maternal health system, how Millie is reinventing it, and how to succeed building a healthcare company.
Timestamps: (00:00) Intro (03:16) Problems in US maternity care (13:21) Why insurance reimbursement drives healthcare (16:11) How bundled care unlocks personalization (18:48) From fiction writer to 20 years in healthcare (24:22) Why consumers don’t act like consumers in healthcare (26:09) The reason scale matters (27:43) Bundled payments and new care design (32:16) What make Millie unique (35:58) Importance of picking regional markets in healthcare (37:08) The two paths for insurance reimbursement (41:08) Why distribution is the product in healthcare (44:25) Opportunities in cash pay care (48:28) How Anu fundraised without a product (51:06) The future of in-person, hybrid, and virtual healthcare (52:56) Building maternity clinics for $150k
Check out Millie: https://www.millieclinic.com/
Where to find Anu: Twitter: https://twitter.com/anu_anusharma1 LinkedIn: https://www.linkedin.com/in/anu-sharma-b169b12
Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Aaron Levie | The $1 Trillion AI Opportunity, Stories From Early Days of Box
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Aaron Levie is a co-founder and the CEO of Box. This conversation covers opportunities in AI, the early days of Box, and lessons Aaron's learned on his founder journey.
Timestamps (00:00) Intro (03:11) Why ChatGPT was an iPhone moment (04:37) Advice for large companies incorporating AI (11:16) Why AI will add jobs, not steal them (16:13) How AI is supercharging Box’s products (19:03) AI agents: the $1 trillion opportunity (25:27)Estimating size of new markets(29:58) Starting Box with high school friends (33:18) Living out of their first office (34:52) Why early investors passed on Box (37:24) Pivoting from consumer to B2B (39:53) How Box got its first customers (41:57) Should founders talk to Associates at VC firms? (43:26) How Mamoon at Kleiner saved Box at its Series B (46:25) Turning down an acquisition before IPO (50:51) Why Box’s IPO was so hard (54:11) Fending off an activist investor during COVID
Check out Box: https://www.box.com/
Where to find Aaron:
Twitter: https://twitter.com/levie
LinkedIn: https://www.linkedin.com/in/boxaaron/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Elad Gil on Conviction, AI, Biotech, Ambition, Speed of Execution, and Non-Obvious Startup Advice
How to Build a Biotech with Celine Halioua at Loyal
This episode is brought to you by Warp. Don’t let payroll and compliance hold your startup back: visit https://joinwarp.com/peel to get started and receive a $1000 gift card when you first run payroll.
Celine Halioua is the founder and CEO of Loyal, a biotech company developing medicine to help dogs live longer and healthier lives. And dogs are just the start - Celine thinks Loyal could one day do the same for humans.
She takes us inside what it’s like to build a biotech company from scratch. We talk through how Loyal’s longevity drugs work, the process of getting FDA approval, her biggest mistakes as a founder, how to approach building in a new market, lessons learned failing to raise her Series B, why rate of growth is all that matters in hiring, and almost not starting the company in the first place.
Timestamps: (00:00) Preview (03:30) How a longevity drug works (06:08) Predictions around longevity (08:26) Why Celine cares so much about not failing (12:05) Differences between biotech and software startups (14:15) Sizing a new market (16:53) Why biotech startups are more dilutive early on (20:22) Getting FDA approval (22:57) Why its hard to prove longevity drugs actually work (24:48) The reason Loyal started with dogs (25:27) How Loyal’s drug slows aging (33:42) Working on longevity to increase free will (34:25) Culture shock at Oxford and dropping out of her PhD (37:22) What makes Josh Koppelman a good VC (39:44) Celine’s two biggest mistakes as a founder (42:39) Why rate of growth is the best indicator of success but the hardest to predict (45:33) Self awareness & how being a CEO is both fun and miserable (48:11) How Laura Deming convinced her to start Loyal (50:18) Finding the science behind Loyal (54:21) Deciding it was the right path to start a company (56:30) Lessons from failing to raise a Series B initially (1:02:18) Why Silicon Valley can build 10x more deep tech startups (1:04:05) Doing big things that improve the world (1:04:50) What Celine looks for in startups Where to find Celine:
Twitter: https://twitter.com/celinehalioua
LinkedIn: https://www.linkedin.com/in/celinehh/
Celine's Website: https://www.celinehh.com/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Giving an AI a Computer with Rahul Sonwalkar, Founder and CEO of Julius AI
Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel Rahul Sonwalkar is the founder and CEO of Julius, an AI data scientist. He takes us inside his epic “Ligma Johnson” prank where he pretended to be fired from Twitter the day Elon acquired the company. He then goes inside his journey of building Julius, sharing lessons learned along the way and his vision for the product. Timestamps: (00:00) Preview
(04:16) The "Ligma Johnson" prank
(09:02) Meeting Elon
(13:10) Doing hackathons in college
(14:30) Scraping emails from Hacker News to get internships
(16:25) Using Twitter to learn and meet people
(22:26) Lessons from his first failed startup
(26:19) Taking too long to quit Big Tech & his failed startup idea in trucking
(32:12) Convincing Guillermo Rauch to invest with speed of execution
(34:48) How to avoid analysis paralysis
(36:15) Building Julius, the AI data scientist
(39:25) How COO of a hot tub company uses Julius
(40:40) Professor embracing AI, using Julius to teach his class
(42:47) Iterating on early versions of the product
(44:42) PMF is as much about the market as the product
(45:08) Building dozens of ChatGPT plugins to acquire Julius’ first users
(45:41) Using dev API keys and missing the first paying customers
(49:22) Talking to hundreds of early customers
(50:10) Why customers love when you ship new features every week
(52:14) The power of Julius’ small team
(54:38) Why Rahul gives his number to customers
(57:47) How to avoid idea backlogs
(59:27) Why Julius tests so many models
(01:01:44) Why it feels great when people love your product
(01:03:43) AI will write more code than humans
(01:06:33) Giving an AI a computer
(01:11:05) What happens to all the AI startups?
(01:12:36) Why you have to Ride the Tiger
(01:16:43) How NVIDIA beat 89 other graphics card startups
(01:20:14) Building a moat as a startup
(01:22:50) Rahul’s favorite AI companies
(01:25:11) Why Julius’ changes UI components based on the use case
(01:27:42) Benefits of lifting
(01:29:54) Why Rahul loves SF
(01:31:38) The early days of Microsoft
Referenced: https://julius.ai/ Guillermo’s tweet: https://x.com/rauchg/status/1773168477957919055 Where to find Rahul: Twitter: https://twitter.com/0interestrates LinkedIn: https://www.linkedin.com/in/rahulsonwalkar23 Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Zero to $90M Revenue in Five Years, How Athletic Brewing Created the Non-Alcoholic Beer Category with CEO Bill Shufelt
Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeel
Bill Shufelt is the Founder and CEO of Athletic Brewing, the craft brewer that created the non-alcohol beer market in the US.
Bill takes us inside the early days of starting the company, including realizing there was an opportunity to make non-alcoholic beer, finding a co-founder, struggling to find early investors, building multiple breweries, and getting into Whole Foods before launching. Our conversation is a case study on creating a new market - I hope you enjoy.
Timestamps:
(00:00) Preview
(04:10) Becoming the #1 beer in Whole Foods
(05:54) The history of non-alcoholic beer
(10:41) Why an outsider had to create this new category
(15:34) Health benefits of avoiding alcohol
(17:51) Turner tries the beer
(22:49) Bill’s wife pushing him to start Athletic Brewing
(26:38) Writing a 96 page white paper on non-alcoholic beer
(28:42) Quitting his job to start six months of research and networking
(30:21) Meeting the perfect co-founder after 100’s of meetings
(32:34) Putting his life savings into a warehouse and brewing equipment
(33:04) The importance of setting company values early on
(34:23) Brewing the first beer in Gatorade jugs
(36:16) Selling the first bottles to retailers
(37:42) Explosive growth in 2019
(39:39) Why new products and D2C helped them scale so fast
(40:39) Using TikTok to sell-out new product launches in 30 seconds
(42:00) The value of doing early customer service himself
(44:45) Getting to 61% market share in non-alcoholic beer
(46:10) Struggling to raise the first angel round
(48:34) Using consistent investor updates to easily raise the Seed, Series A, and Series B
(50:47) Transitioning to institutional capital for its Series C
(52:33) Betting on a new category to expand market size
(55:44) Information access is enabling healthier consumer behavior
(58:11) Bill’s early strategy for marketing the product
(1:01:43) The importance of over communicating with your investors
(1:03:44) Why retailers like Athletic Brewing’s unique omni channel approach
(1:06:16) How building its own breweries and supply chain enabled its unique strategy and better margins at scale
(1:09:04) Getting into Whole Foods before launching
(1:11:31) Doing unscaleable things over and over again
(1:13:50) Why entrepreneurship is a long game
(1:14:22) Most of Athletic’s new products come from the team
Check out Athletic Brewing: https://athleticbrewing.com/
Where to find Bill:
LinkedIn: https://www.linkedin.com/in/bill-shufelt-650059138
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
SMB Masterclass: Zero to $150M Revenue in Two Years with Dane Atkinson, Founder and CEO of Odeko
Josh Miller on How The Browser Company Started, How to Hire, Arc Search, and Building in Public
Josh Miller is CEO and co-founder of The Browser Company, which is building a new internet browser. He explains why effective hiring requires caring a lot and trusting your taste and why Arc Search, a default mobile browser, could be The Browser Company’s next act.
TIMESTAMPS:
(00:00:00) Intro
(00:02:35) Working for Obama
(00:03:55) Giving up 8-figures in Meta stock
(00:08:19) Barack Obama’s favorite web browser
(00:09:02) Why Arc released a mobile browser
(00:10:03) How Josh met Josh Kushner
(00:11:26) Becoming an EIR at Thrive Capital
(00:12:09) How The Browser Company got started
(00:15:51) Why they named it The Browser Company
(00:18:49) Pivoting to consumer when COVID hit
(00:20:37) Leaving Thrive to join as a Co-founder in February 2020
(00:21:05) Why COVID made browsers relevant
(00:22:42) How to hire a great team
(00:25:02) Hiring Josh Lee to edit their videos
(00:26:52) The biggest difference between Josh as a first-time and second-time founder
(00:28:46) Learning to delegate
(00:34:03) Why Thrive gave up double-digit equity back to the founders
(00:40:18) Launching
(00:40:52) Why build a web browser
(00:42:17) This history of browsers
(00:43:36) Why they’ve gotten worse over time
(00:50:26) The reasons people use Arc
(00:53:23) How Arc will make money
(00:56:45) Why Arc’s existential question is getting people to care about their browser
(00:59:47) The story behind Arc Search
(01:00:45) Arc’s potential growth flywheel
(01:09:17) Why Arc bet big on building in public on YouTube
(01:10:16) The publisher backlash to Arc Search
(01:11:33) Why praising your team publicly is so important
(01:13:39) How Josh hired Nate Parrott
More on The Browser Company:
www.youtube.com/c/TheBrowserCompany
Where to find Josh:
Twitter: https://twitter.com/joshm
LinkedIn: https://www.linkedin.com/in/josh-miller-b31259106
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Market Update: Peter Walker on 2023 VC Valuation Trends, Dry Powder, New Bubbles, Employee Trends
Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/ Brought to you by Attio, the next generation of CRM: https://bit.ly/AttioThePeel Peter Walker is Head of Insights at Carta and writes a newsletter called “The Data Minute”, a weekly newsletter highlighting data from over 43,000 private tech companies that use Carta’s platform to manage their cap table. He gives us into a deep dive on VC valuation trends, the fundraising landscape, and startup strategies. Timestamps:
(00:00) Intro
(04:50) Valuation trends in 2023
(08:10) Why Seed valuations went up over the past two years
(12:27) AI startups are getting higher valuations
(17:40) Why Biotech might be the next big bubble
(19:15) Boston as the 2nd largest VC ecosystem
(21:15) How SAFE’s work
(24:06) The impending SAFE reckoning
(26:13) Why startups don’t pay dividends
(28:31) Downrounds were 2x more common in 2023
(32:11) Almost half of all 2023 Series As were extensions
(35:34) Is there really a lot of dry powder?
(40:43) The emerging manager fundraising landscape
(48:19) Exit environment
(51:45) Why pre-Series B is the most common acquisition stage
(52:47) Liquidation preference & why an acquisition at Seed might make a founder more money than at a Series B
(55:59) Compensation market data
(56:38) Why the number of total startup employees shrank in 2023
(57:38) Why startup employees aren’t exercising their options
(1:00:57) Health of the secondary markets
(1:04:51) Most co-founder splits aren’t 50/50
(1:06:47) Why you should always vest co-founder equity
(1:09:30) 2023 record year for startup shutdowns
(1:17:19) Will other startup ecosystems ever catch Silicon Valley? Links: Carta’s Q4 ‘23 Private Market Report: https://carta.com/blog/state-of-private-markets-q4-2023/ Peter’s Newsletter: https://carta.com/subscribe/data-newsletter-sign-up/ Where to find Peter: Twitter: https://twitter.com/PeterJ_Walker LinkedIn: https://www.linkedin.com/in/peterjameswalker/ Where to find Turner: Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak/ Newsletter: https://www.thespl.it/
Chris Bakke on Selling to Elon, Small Exits, and Using Memes for Marketing
Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/
Chris Bakke has founded and sold three companies for between $25-100 million to Zillow, Indeed, and most recently Twitter / X. He shares how he convinced Elon to buy his company, what it's like working for Elon, exactly how the Twitter algorithm works, and all his meme making secrets.
— — — —
Timestamps:
(00:00) Intro
(02:52) Inside Twitter’s acquisition of Laskie
(05:38) Why Twitter / X works so well for recruiting
(08:11) A sneak peek at upcoming Premium features
(13:58) How the X algorithm works
(20:48) Why “dwell time” is the most important metric
(24:07) What it’s like reporting to Elon
(27:40) Elon’s crazy ability to context-switch
(29:16) Why you should consider selling your company for $25-100 million
(35:39) The reasons large M&A deals are so rare
(42:07) Surviving inside Big Tech as a founder
(46:23) Chris's philosophy on company building
(51:23) Why “Time in Market” is so underrated
(53:44) YC’s “sandwich incident”
(55:44) How to use memes for marketing
(58:55) Chris’ 100+ page Google Slide meme library
(1:01:46) His top three favorite meme templates
(1:03:48) His favorite proprietary trade secret at X
(1:05:03) Turning down jobs at Coinbase and WhatsApp
— — — —
Twitter jobs: https://twitter.com/jobs
— — — —
Where to find Chris
Twitter: https://twitter.com/ChrisJBakke
LinkedIn: https://www.linkedin.com/in/bakk3/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Inside Anchor’s Journey to Product Market Fit and 9-Figure Sale to Spotify with Mike Mignano
Eric Newcomer on Scaling to 80,000 Newsletter Subs, How to Pitch Reporters
Eric Newcomer is the founder of Newcomer, a publication he launched in October of 2020 to cover the business of startups and venture capital. He had just left Bloomberg after nearly six years, and was previously the first employee at The Information.
— — — —
Timestamps:
(00:00) Intro
(02:46) The current state of media
(05:59) Anchoring his 4th grade newscast
(07:21) Becoming the 1st employee at The Information
(09:34) How reporters get stories
(21:12) The moment he quit Bloomberg to start Newcomer
(26:02) Why he writes for VC insiders
(32:19) The VC top fund survey
(34:01) The Founders Choice VC leaderboard
(35:51) Why leaked documents grow his newsletter the fastest
(39:45) When Eric knew Newcomer was going to work
(43:31) How events become Newcomers most profitable business
(51:56) Why Eric invested in Substack
(57:42) Why its harder to cover tech’s downturn than boom times
(59:10) How to pitch a story to a reporter
(01:02:59) Why the internet incentivizes negative media coverage
(01:06:06) Advice for starting a media company
(01:10:33) Why media works so well to sell adjacent products
(01:12:55) Newcomer Banking Summit
(01:14:27) The $1.3B acquisition that happened at his first conference
(01:20:05) New products Eric’s thinking about
— — — —
Referenced:
Newcomer Passes $1m in Revenue: https://www.axios.com/2024/01/04/substack-writer-eric-newcomer-says-his-revenue-surpassed-1m-in-2023
Pragmatic Engineer Newsletter: https://blog.pragmaticengineer.com/
Lenny’s Newsletter: https://www.lennysnewsletter.com/
Mike Solana’s Pirate Wires: https://www.piratewires.com/
Mentioned Newcomer Articles:
VC Survey: https://www.newcomer.co/p/sequoia-founders-fund-usv-elad-gil
Founder's Choice: https://www.newcomer.co/p/founders-choice-vc-rankings-revealed
Paywalled Bill Gurley Interview: https://www.newcomer.co/p/above-the-crowd
SBF’s Leaked FTX Email: https://www.newcomer.co/p/exclusive-read-sam-bankman-frieds
Eric’s first article on Sequoia: https://www.newcomer.co/p/sequoias-political-paradox
— — — —
Where to find Eric:
Twitter: https://twitter.com/EricNewcomer
LinkedIn: https://www.linkedin.com/in/ericpnewcomer/
Newsletter: https://www.twitter.com/newcomer
Email: newcomer@newcomer.co
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Siqi Chen on How To Go Viral, Secrets to Storytelling, and Forgetting Best Practices
Siqi Chen is the Co-Founder and CEO of Runway, the modern and intuitive way to model, plan, and align your business for everyone on your team. Or, in Siqi’s words, “revolutionizing the $80 trillion business industry”.
A few months ago, Runway’s new website went viral across the internet. Siqi takes us inside how that happened. He’s no stranger to going viral, having previously built multiple companies that went from zero to millions of users within weeks, including the fastest growing product ever before ChatGPT took the crown in late 2022.
— — — —
Brought to you by Attio, the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioThePeel
— — — —
Timestamps:
(00:00) Intro
(02:00) Sponsor: Attio
(02:59) How Siqi goes viral
(06:13) Why conversion doesn’t always matter
(11:23) How to make B2B software more fun
(14:31) Working on the Curiosity and Spirit rovers at NASA
(16:50) Re-designing at the entire codebase and product at his first startup job
(21:13) Earning the nickname “FB Millz” making a million dollars building Facebook games
(25:11) Selling to Zynga and building the fastest growing product before ChatGPT
(28:36) Building a game with 90% Day 1 retention
(30:09) Being played by Kim Kardashian, Jack Dorsey, and shut down by Tim Cook
(32:10) Almost getting fired building a growth team at Postmates
(35:04) Building Sandbox VR: “escape rooms in VR”
(40:35) Meeting Kanye
(44:38) Getting the idea for Runway when COVID hit
(47:32) Why spreadsheets run every business
(54:40) Disrupting the $80 trillion business industry
(57:55) Making formulas 50x easier than Excel
(01:02:32) Why Runway’s building a painkiller
(01:06:32) How to fundraise
(01:08:32) Why the first question from an investor is the reason they won’t invest
(01:11:28) How to tell a company’s story
(01:15:23) The three layers of a story
(01:17:28) The importance of positioning in storytelling
(01:18:56) Runway’s flexible remote work strategy
(01:21:34) Why their hiring strategy changed over time
(01:22:39) Siqi’s single interview question & the three traits he looks for when hiring
(01:26:10) Unlearning consumer to learn B2B
(01:30:26) Navigating the first three years of no customers
(01:31:45) What surprised Dylan Field the most about building Figma
— — — —
Referenced:
Runway’s website: https://runway.com/
Reform Collective Design Agency: https://www.reformcollective.com/
Amplitude: https://amplitude.com/
SandboxVR: https://sandboxvr.com/
Lulu Cheng’s Android Playbook: https://www.piratewires.com/p/anduril-comms-strategy-early-days
— — — —
Where to find Siqi:
Twitter: https://twitter.com/blader
LinkedIn: https://www.linkedin.com/in/siqic/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Automating the $80 Billion SOC 2 Market with Shrav Mehta (Secureframe)
Shrav Mehta is the Founder and CEO of Secureframe, which empowers businesses to build trust with customers by automating information security and compliance. Shrav started the company in 2019 after being an early employee at Scale, Pilot, Lob, and Hired, and has since raised from investors like Kleiner Perkins, Backend Capital, Soma Capital, and Banana Capital.
Shrav takes us inside how Secureframe’s automating the compliance market, lessons learned on recruiting and scaling teams, and his contrarian take on finding product market fit.
— — — —
Timestamps: (00:00) Intro (2:10) Automating the $80 billion compliance market (15:49) Learning to program building Android apps (22:50) Joining Lob, Hired, and Scale early (27:25) Joining Pilot to learn marketing and growth (33:31) Shrav’s secret discount furniture supplier (35:04) Finishing three years of college in one year (39:06) Getting 30-40 customers before starting Secureframe (44:24) Non-intuitive fundraising advice from pre-product to IPO (50:08) Why the IPO isn't the ultimate goal (54:40) How Shrav approaches hiring (58:04) Tactics for effective reference checks (1:01:01) Why warm intros are so helpful (1:02:32) How to send good cold emails (1:05:31) Why you should not use LinkedIn “open to work” (1:06:54) Lessons learned scaling teams (1:13:45) Why finding PMF is a 24/7 job and never ends
— — — —
Referenced:
Secureframe: https://secureframe.com/
Lob: https://www.lob.com/
Hired: https://hired.com/
Scale: https://scale.com/
Zapier’s Secrets to PMF: https://www.youtube.com/watch?v=NJMjuYt9jEc
What it took to raise a Series A in 2023: https://news.crunchbase.com/venture/seed-to-series-a-funding-2023-jones-kruze — — — — Where to find Shrav:
Twitter: https://twitter.com/shravvmehtaa/
LinkedIn:https://www.linkedin.com/in/shravmehta/
Where to find Turner:
Twitter: https://twitter.com/turnernovak/
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
Epic Gardening's $100+ Million YouTube Playbook with Kevin Espiritu, Founder and CEO
Kevin Espiritu is the founder and CEO of Epic Gardening, which is, by multiple measures, one of the largest brands in gardening on the planet.What started in 2013 as a blog has since evolved into a gardening empire spanning YouTube, TikTok, Instagram, Facebook, 4,500 gardening stores, and three gardening books.
Epic raised a $17.5m Series A from The Chernin Group in 2021, and according to external sources did $27 million in revenue in 2022.
— — — —
Brought to you by Attio, the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioThePeel
— — — —
Timestamps:
- (00:00) Intro
- (04:03) Sponsor: Attio
- (05:09) A deep dive on the history of YouTube
- (12:04) The YouTube algorithm and meta game
- (40:17) Using Reddit to drive initial blog traffic
- (46:56) How creator-led businesses have negative CAC
- (47:12) Why creator businesses must be very small or very large
- (49:38) How YouTube is changing today
- (50:00) Acquiring a gardening blog for $1k from an Indian VC
- (52:43) His process for doing acquisitions
- (53:38) Launching his first product
- (57:54) His biggest mistakes launching new products
- (58:30) Buying his own warehouse
- (59:04) Non-intuitive ways a product can influence your cost structure
- (1:03:00) Kevin’s approach to hiring
- (1:04:40) Why he raised a Series A as a YouTube creator
- (1:05:27) How to approach investing in AI
- (1:19:53) Why Kevin wrote three books
- (1:23:26) Why more people will grow food at home
- (1:25:20) How he approaches celebrity partnerships
— — — —
Referenced:
- Epic Homesteading: Your Guide to Self-Sufficiency on a Modern, High-Tech, Backyard Homestead https://www.amazon.com/Epic-Homesteading-Self-Sufficiency-High-Tech-Homestead/dp/0760383766
- MrBeast https://www.youtube.com/@MrBeast
- MrBeast's Feastables https://feastables.com/
- Logan Paul x KSI PRIME https://drinkprime.com/
- MatPat of @GameTheory https://www.youtube.com/channelUCo_IB5145EVNcf8hw1Kku7w
- Michelle Phan https://www.youtube.com/user/michellephan
- Ipsy: https://www.ipsy.com/ by Michelle Phan
- Matthew Beem https://www.youtube.com/channel/UCR_J_SntqJh5eXw66d5hJxA
- The Chernin Group https://tcg.co/
— — — —
Where to find Kevin / Epic Gardening
Twitter: https://twitter.com/KevinEspiritu
YouTube 1: https://www.youtube.com/user/kevinmespiritu
YouTube 2: https://www.youtube.com/@epicgardening
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/
How Kirsten Green Built Forerunner Ventures
The Great Media Arbitrage: How Craig Fuller Built FreightWaves
Craig Fuller is the Founder and CEO of FreightWaves, a media company and data provider for the global supply chain. He’s also the CEO of Flying Media Group, which he founded in 2021 to acquire Flying Magazine, the largest US-based print magazine for the aviation industry. This conversation is split into three parts: a crash course on logistics and supply chains, how to build and run a media company, and finally all things print magazines.
Topics discussed include:
- (00:00) Intro
- (02:39) Why logistics is the most important industry no one talks about
- (04:23) The rise of deglobalization
- (11:07) How Colombia benefits from US manufacturing
- (14:52) Why Craig’s watching US onshoring and Mexican nearshoring
- (18:18) How the supply chain function is changing
- (28:59) The US labor availability problem
- (32:40) Why AI will never fully replace humans in media
- (34:56) The early days of FreightWaves
- (41:04) Predicting recessions months before it shows up in data
- (48:51) Why logistics is the best barometer of the global economy
- (52:44) Taking 12+ months to raise FreightWaves first venture round
- (59:24) Surviving COVID with only two months of runway
- (01:05:20) How FreightWaves accidentally became a media business
- (01:08:15) Why the best startups make low risk, high upside decisions
- (01:13:27) Why media business are the arbitrage opportunity this decade
- (01:15:55) Getting 200%+ IRR’s buying print magazines, starting with flying
- (01:17:50) Building his own airport and flying community
- (01:30:16) Almost failing to turnaround his first magazine acquisition
- (01:39:06) His non-intuitive lessons from building media businesses
- (01:43:39) Craig’s favorite media businesses
- (01:48:50) How to build a brand in media
Referenced:
Where to find Craig:
Twitter: https://twitter.com/FreightAlley
LinkedIn: https://www.linkedin.com/in/incab
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Banana Capital: https://bananacapital.vc
Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Building a $510 Million Personal Care Giant with Danielle Cohen-Shohet, Founder & CEO of GlossGenius
Danielle Cohen-Shohet is the CEO and Founder of GlossGenius, the all-in-one booking, payments and POS solution that helps beauty and wellness professionals drive bookings and grow their business.
Danielle started the company in 2016 and has since grown it to a $510 million valuation. This is while taking a disciplined approach to fundraising, raising roughly $70 million throughout the life of the company.
—
Topics include:
- A crash course on the $160 billion beauty, health, and wellness market
- How the industry's shifting to time-based billing and upfront payments
- Why GlossGenius spends so much time on customer experience
- Surviving a 90% drop in revenue during COVID
- Why she credits talking to and listening to customers to GlossGenius success
- A look inside each funding round, and why Danielle kept them small
- How she learned to delegate as the company scaled
- Why the big picture is often made of little details
- Danielle’s secret for running a capital efficient business
- GlossGenius’ Hiring and Interviewing Manual
- Why most companies aren’t good at hiring
- Danielle’s favorite interview questions
—
Where to find Danielle:
- Twitter/X: https://twitter.com/dcohenshohet
- LinkedIn: https://www.linkedin.com/in/dcohenshohet
—
Where to find Turner:
- Newsletter: https://www.thespl.it
- Twitter/X: https://twitter.com/TurnerNovak
- Banana Capital: https://bananacapital.vc
—
Production and distribution by: https://www.supermix.io
—
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The Story of Nubank, The World’s Largest Neobank with Co-founder Cristina Junqueira
Cristina Junqueira is the Co-founder and Chief Growth Officer of Nubank, the largest neobank in Latin America – and in the world – with more than 80 million customers. She is also the second self-made female billionaire in Brazil.
Cristina and her co-founders David Vélez and Edward Wible launched Nubank in 2013, essentially building the fintech category in a market where it was nonexistent, and went on to release a no-fee credit card, app, and other banking products across Brazil, Mexico, and Colombia.
Cristina takes us through the rise of Nubank, from the scrappiest days building in a house in Sao Paulo to being backed by investors like Sequoia, Founders Fund, DST, TCV, Tiger Global, and Warren Buffett, and then on to their IPO in December 2021. We also touch on the impact of Nubank’s distinctive brand choices, how they navigated government regulations that nearly shut them down, and how they were able to spend $0 on marketing throughout most of their history.
— — — —
TIMESTAMPS:
(00:00) Preview
(02:38) Fintech and the preconditions for disrupting financial services in LatAm
(05:38) Educating investors on the opportunity for fintech in LatAm
(07:35) The scale of unbanked and underbanked populations in Brazil, Mexico, and other countries; and why expanding access to these products increases NuBank's market share
(08:21) Expanding the pie and just how profitable banks can be in LatAm
(15:37) Starting NuBank and the lessons Cristina learned from incumbent banks
(18:11) The biggest hurdle to starting NuBank
(19:33) Navigating Nubank’s first product from inception to successful credit card
(21:08) Spending $0 CAC in an industry with hugely expensive marketing pushes
(22:32) $0 on marketing and scrappy ethics
(26:40) The crazy circumstances around Nubank’s Series A fundraise
(36:54) Cristina’s reflections on the IPO in December 2021
(39:31) How Nubank navigates a changing macro environment
(40:40) The importance of Nubank’s distinctive brand
(42:57) Surviving an existential threat from Brazil’s government
(46:28) Scaling from a small scrappy team to a multinational global publicly traded company
(49:02) Personal growth and maintaining strong co-founder relationships
Referenced:
Nubank: https://nubank.com.br/en/
Nubank's IPO mints Cristina as a billionaire: https://www.forbes.com/sites/jeffkauflin/2021/12/09/
Where to find Cristina:
Twitter: https://twitter.com/junqueira_cris
LinkedIn: https://www.linkedin.com/in/crisjunqueira/
Where to find Turner:
Newsletter:https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Banana Capital: https://bananacapital.vc
Immigrant to $250M CEO: How Circle Powers the Creator Economy with Co-founder and CEO Sid Yadav
Sid Yadav is the Co-founder and CEO of Circle, the all-in-one community platform trusted by creators like Tiago Forte, David Perell, and Miles Snider. Sid started the tech blog Rev2 when he was a teenager in New Zealand, writing about the launch of YouTube and the iPhone. He was the founding engineer and designer of Teachable, which he helped scale to +25m+ in ARR before it was acquired in 2020. He started Circle in 2019 with co-founders Rudy Santino and Andrew Guttormsen, which they scaled to $16m in ARR by December of 2023.
Circle has since raised $31m from Investors like Tiger Global, Notation Capital, Bungalow, Todd Goldberg, Rahul Vohra, Scott Belsky, Josh Buckley, Ankur Nagpal, Wade Foster, and Dharmesh Shah.
Sid immigrated with his family from India to New Zealand as a teenager and to the US after college. His story is a perfect encapsulation of the American Dream, and I’m excited to share this conversation.
— — — —
Brought to you by Deel, the global HR + payroll platform used by 20,000+ teams. Deel’s in-house immigration team gets you and your team worldwide visas without the legwork.
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— — — —
Topics discussed include:
(03:53) Why the creator economy is booming despite negative sentiment
(13:22) Writing a popular tech blog as a teen in the mid 00’s
(23:16) Joining Teachable as the 2nd employee
(40:30) Why Teachable CEO Ankur Nagpal invested 90% of his liquid net worth in Circle’s $1.7m Pre-seed round
(48:44) Sid’s inside view at the creator economy before, during, and after COVID
(52:50) The magic of Lenny Rachitsky’s creator flywheel
(56:10) The reason Sid raised a Seed from lots of investors instead of one large check
(01:14:30) Inside raising a Series A from Tiger Global in 2021
(01:22:19) Why Sid writes an investor update every month
(01:25:15) Going from Zero to $16m ARR in four years
(01:27:28) How Circle approaches its product roadmap
(01:29:20) Building a community around your product
(01:37:03) Advice for running a remote-first team
(01:46:54) How Sid convinced the founder of Zapier to be his CEO coach
(01:54:20) Why founders need to deal with reality
Referenced:
“Cost of a meeting” tweet: https://twitter.com/0xgaut/status/1620815168921038850
Tiago Forte Building a Second Brain: https://www.buildingasecondbrain.com/foundation
PARA Method: https://fortelabs.com/blog/para/
Lenny’s interview with Brian Chesky: https://www.youtube.com/watch?v=4ef0juAMqoE
Turner’s interview with Wade Foster, Co-founder and CEO of Zapier: https://youtu.be/NJMjuYt9jEc
Myles Snyder: https://mylessnider.com/
Where to find Sid:
- Twitter: https://twitter.com/sidyadav
- LinkedIn: https://www.linkedin.com/in/sidyadav
Where to find Turner:
- Newsletter: https://www.thespl.it
- Twitter: https://twitter.com/TurnerNovak
- Banana Capital: https://bananacapital.vc
🎮 Growing Medal to 10+ Million Gamers | Pim de Witte (Co-founder and CEO, Medal)
How Unit Operates with Precision, with Itai Damti (Co-founder and CEO of Unit)
Itai Damti is the Co-founder and CEO of Unit, the platform that helps leading tech companies store, move, and lend money.Unit has raised over $170 million from investors like Better Tomorrow Ventures, Accel, Insight, and dozens of angels.
—
In this episode, we discuss:
- The first and second wave of fintech innovation
- How the second wave brings financial services inside other software
- How Unit beat the competition and raised $170 million by focusing on product and expanding the market size
- Itai’s framework for leveraging his investors
- His strategy for prioritizing as a founder
- How Unit operates with precision
- And why they haven’t built any crypto products
—
Brought to you by Artie, the real-time database replication solution that sets up in minutes and requires zero day-to-day maintenance.
Sign-up for a demo and get two weeks free: https://bit.ly/3uWTzWJ
—
Where to find Itai:
- Twitter: https://twitter.com/itaidamti
- LinkedIn: https://www.linkedin.com/in/itaidamti
—
Where to find Turner:
- Newsletter: https://www.thespl.it
- Twitter: https://twitter.com/TurnerNovak
- Banana Capital: https://bananacapital.vc
—
Production and distribution by: https://www.supermix.io
—
For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Pricing Lessons from the Fastest Growing Companies with Kevin Liu, Co-founder and CEO of Metronome
Kevin Liu is the Co-founder and CEO of Metronome, which enables software companies to launch, iterate, and scale their business models with billing infrastructure that works at any size and stage. Prior to Metronome, Kevin and his co-founder Scott Woody both sold their respective separate companies to Dropbox.
Kevin and Scott started Metronome in 2019, and have since raised over $30 million from investors like a16z, General Catalyst, Elad Gil, Lachy Groom, and dozens of other angels.
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In this episode, we discuss:
- The history and evolution of software business models
- A crash course on all things software pricing
- Kevin’s framework for iterating on new startup ideas
- His 2-days on, 1-day off strategy for early customer needfinding
- How he leveraged angels to raise Metronome’s Seed and Series A rounds
- The dangers of over-building a product
- Why Metronome sacrificed its own margins to scale with OpenAI
- How Kevin thinks founders should prioritize their time
- Frameworks for building a pricing model
- The biggest pricing mistakes companies make
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Referenced:
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Where to find Kevin:
- LinkedIn: https://www.linkedin.com/in/kevinyliu
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Where to find Turner:
- Newsletter: https://www.thespl.it
- Twitter: https://twitter.com/TurnerNovak
- Banana Capital: https://bananacapital.vc
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Production and distribution by: https://www.supermix.io
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Zapier’s Secrets to Product Market Fit with Wade Foster (Co-founder and CEO of Zapier)
How Solugen is Saving the $5 Trillion Chemical Industry (Co-founders Gaurab Chakrabarti & Sean Hunt)
Gaurab Chakrabarti and Sean Hunt are the Co-founders of Solugen, which replaces petroleum based products with plant-derived substitutes without sacrificing affordability or performance. They met playing poker in college, kickstarted the company with $10k from an MIT pitch competition, and have since scaled the business to over nine-figures in revenue.
Solugen has raised over $642 million from investors like Fifty Years, Lowercarbon Capital, Founders Fund, Refactor Capital, and Cantos Ventures.
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Topics discussed:
- How the chemicals industry touches 25% of US GDP
- Why the industry is like real estate: fragmented and focused on asset utilization
- The reason chemicals companies have terrible NPS scores
- How Solugen’s manufacturing process converts plants and C02 into chemicals
- Meeting over a game of poker while getting their PhD’s
- Winning $10k from an MIT pitch competition to capture 10% of the float spa market in Dallas, Texas
- Why the first wave of Cleantech startup fail
- Why logistics and supply chain are the biggest problems in Chemicals
- Their framework for thinking big, but taking little steps to get there
- Running their homemade metal catalyst reactor at YC Demo Day
- Launching, scaling, and selling a CPG wipes company to prove their chemicals worked
- Building their first factory (the BioForge) on the site of an exploded wax distillery
- Their strategy for getting large, multinational companies to try their products
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Referenced:
- YC Application video: https://www.youtube.com/watch?v=tItLPnLIH4o
- Solugen - The First Carbon Negative Molecule Factory: https://jeffburke.substack.com/p/solugen-the-first-carbon-negative
- Solugen - The Century of Biology: https://centuryofbio.com/p/solugen
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Where to find Gaurab:
- Twitter: https://twitter.com/gaurabc
- LinkedIn: https://www.linkedin.com/in/gaurabchakrabarti
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Where to find Sean:
- Twitter: https://twitter.com/TungstenSeanide
- LinkedIn: https://www.linkedin.com/in/huntsean
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Where to find Turner:
- Newsletter: https://www.thespl.it
- Twitter: https://twitter.com/TurnerNovak
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Production and distribution by: https://www.supermix.io
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For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Secrets of the $131 Billion Parking Industry with Jonathon Barkl (Co-founder and CEO of AirGarage)
Jonathon Barkl is the Co-founder and CEO of AirGarage, a full-stack parking management company that helps real estate owners increase their income.
Jonathon and his co-founders Chelsea and Scott started the company in 2017. They’ve since raised roughly $15 million from investors including Founders Fund, Floodgate, a16z, Abstract, and prior guest of the show Ryan Delk.
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Topics discussed:
- A crash course on the business model of parking
- Why parking lots make most of their money from tickets and towing
- The reason American cities dedicate up to 30% of space to parking
- How the $131 Billion parking industry evolved to be so complicated and outdated
- Why dynamic pricing in parking is harder than hotels and airlines
- The three primary business models for a parking lot
- Why Air Garage can increase a parking lots profitability by 4-5x
- How part of its business was inspired by scooter companies like Bird and Lime
- Starting “Airbnb for Driveways” in 2016 to solve their own problem as college students
- The sales lessons Jonathon learned doing door-to-door sales in the Arizona heat
- How getting scammed out of $6,000 led to pivoting their business model
- Moving to San Francisco with no connections and raising a Seed round
- How they closed a Series A in a week
- The importance of investor brand when hiring early employees
- Why Jonathon cares so much about branding as a parking company
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Referenced:
https://www.airgarage.com/
https://parkingreform.org/resources/parking-lot-map/- Mac vs PC ads: https://www.youtube.com/watch?v=0eEG5LVXdKo
- Never Split the Difference: https://www.amazon.com/Never-Split-Difference-Negotiating-Depended/dp/0062407805
https://en.wikipedia.org/wiki/Detroit
https://en.wikipedia.org/wiki/List_of_recessions_in_the_United_States
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Where to find Jonathon:
- Twitter: https://twitter.com/jonathonbarkl
- LinkedIn: https://www.linkedin.com/in/jonathonbarkl
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Where to find Turner:
- Newsletter: https://www.thespl.it
- Twitter: https://twitter.com/TurnerNovak
- Banana Capital: https://bananacapital.vc
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Production and distribution by: https://www.supermix.io
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Securing Open Source Software with Dan Lorenc, Co-founder & CEO of Chainguard
From Food Stamps to a $20 Million Fund with Nichole Wischoff
Nichole Wischoff is the founder of Wischoff Ventures, a Pre-Seed and Seed firm that invests up to $1 million in non sexy industries. Nichole closed her first fund in 2021, and previously was an early employee at Blend (NYSE:BLND), One (acquired by Walmart in 2022), and Built.
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Topics discussed include:
• Growing up on food stamps in Arkansas
• How studying abroad in Belgium changed Nichole’s life
• How falling in love with running got her into college and her first job
• Why Taylor Swift could be the first female President
• Opening a bakery to pay rent while teaching English in Spain
• Getting her first job at Citi’s non-profit housing financing team
• Leveraging that experience to get a job in fintech
• Making her first angel investment in Vesta
• How Nichole got One Financial its first 25k users
• Helping sell One Financial to Walmart
• How Lee Fixel and Chad Byers helped raise her first $5m fund
• Lessons learned going from a $5m to $20m fund in 2022
• Nichole’s advice for anyone raising their first fund
• Behind the scenes of her viral “Third Tier VC” moment
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Referenced:
•Taylor Swift (Acquired’s Version): https://www.acquired.fm/episodes/taylor-swift-acquireds-version
• Nichole’s $20m Fund Announcement https://techcrunch.com/2022/12/16/solo-gp-nichole-wischoff-raises-20m-fund-backed-by-peter-thiel-to-invest-in-unsexy-businesses/
• J Cal’s “3rd or 4th Investor in Uber” Montage: https://www.youtube.com/watch?v=OK4Mku_s4H4
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Where to find Nichole:
• Twitter: https://twitter.com/NWischoff
• LinkedIn: https://www.linkedin.com/in/nicholewischoff
• Wischoff Ventures: https://www.wischoff.com/
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Where to find Turner:
• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
• Banana Capital: https://bananacapital.vc
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Production and distribution by: https://www.supermix.io
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Lessons From Scaling Pilot to a $1.2 Billion Valuation with Co-founder and CEO Waseem Daher
Waseem Daher is the Co-founder and CEO of Pilot, the bookkeeping, CFO, and tax provider for startups and fast growing businesses. Prior to Pilot, Waseem and his co-founders Jeff and Jessica sold companies to Oracle and Dropbox.
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Waseem, Jeff, and Jessica started Pilot in 2017, and have since raised over $160 million from investors like Index Ventures, Stripe, Sequoia, Whale Rock, Jeff Bezos, and over 40+ angel investors.
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In this episode, we discuss:
• Why Waseem’s building a startup that does your accounting
• The reason he first started doing his own bookkeeping, and why he doesn’t recommend it to other founders
• When startups should build something themselves and when to outsource
• All the mistakes Waseem made building and selling his first two startups to Oracle and Dropbox
• How to avoid “fake work”
• How to get ROI from conferences
• His disastrous first ever meeting with a VC
• Why the best fundraising advice is to build a business that doesn’t need to raise money
• “Companies are bought, not sold” and his framework for startup M&A
• Why it’s a mistake to build your startup just to be acquired
• Why consensus startup ideas rarely work, and the best startups need some secret or structural change that no one else has noticed yet
• Why tech-enabled service businesses are so hard to scale
• How Pilot got its first customers
• Pilot’s unique approach to raising its Seed round
• The initial scare when raising their Series A
• Why its Series B was half of what they could have raised
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Where to find Waseem:
• Twitter: https://twitter.com/waseem
• LinkedIn: https://www.linkedin.com/in/wdaher
• Newsletter: https://waseem.substack.com/
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Where to find Turner:
• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
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Production and distribution by: https://www.supermix.io
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For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Bootstrapping Webflow to $10M ARR, and scaling to a $4B Valuation with Vlad Magdalin (Co-founder & CEO)
Vlad Magdalin is the Co-founder and CEO of Webflow, software that empowers designers to build websites without code. Vlad started the company with his co-founders Sergie Magdalin and Bryant Chou in 2013, and has since raised roughly $335 million supported by investors like Accel, Khosla Ventures, YCombinator, Capital G, and Eric Bahn.
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Disclaimer: Mercury is a financial technology company, not a bank. Banking services are provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC.
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Topics discussed include:
• The history of web browsers, websites, and web design
• Why websites are the ultimate economic enablers
• How Webflow empowers anyone to design websites without code
• Why website design is a gateway into programming
• How the movement to CSS and web standards in the 2000’s and 2010’s created the opportunity for Webflow to build a product around responsive design
• Moving to the US with his parents and five siblings as refugees from the USSR at nine years old
• How losing half of their luggage and immigration documents in the move enabled his dad to buy the family’s first computer
• The first website Vlad ever designed for a Brad Pitt movie
• How his experience dropping out of a computer science degree to work in 3D animation at Pixar, then going back to school gave him the idea for Webflow
• Failing to build Webflow three times between 2005 and 2008
• Why the spouses and partners of founders are the unsung heroes of startups
• The moment he immediately quit his job and attempted Webflow for the fourth time
• Burning three months of runway on a Kickstarter that never went live
• Liquidating his retirement account, paying rent with credit cards, and selling and leasing back the family car’s to keep the business running
• Vlad’s exuberant optimism that kept him going for 10 years
• Failing to get into YC, and the crazy story behind getting accepted the second time
• The trajectory-altering customer and fundraising advice they got from Paul Graham
• The “Investing on Principle” contract they signed with Accel who led Webflow’s Series A
• Why Vlad thinks every startup founder should operate with the assumption they’ll never be able to raise money again
Referenced:
• Inventing on Principle (Video): https://www.youtube.com/watch?v=PUv66718DII
• Inventing on Principle (Transcript): https://jamesclear.com/great-speeches/inventing-on-principle-by-bret-victor
• The Infinite Game: https://simonsinek.com/books/the-infinite-game/
Where to find Vlad:
• Twitter: https://twitter.com/callmevlad
• LinkedIn: https://www.linkedin.com/in/vladmagdalin
Where to find Turner:
• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
Production and distribution by: https://www.supermix.io
Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
What is OpenStore? How Keith Rabois is Acquiring Shopify Brands
The $4 Trillion Business of Financial Crime with Natasha Vernier, Co-founder and CEO of Cable
Natasha Vernier is the Co-founder and CEO of Cable, the all-in-one effectiveness testing platform for financial services. Prior to Cable, Natasha joined UK neobank Monzo when it had less than 100 customers. She built and led their financial crime team for five years, and is one of the most knowledgeable individuals in the world on financial crime, which amounts to over $4 trillion per year, or 4% of global GDP.
Natasha started Cable in 2020 with her co-founder Katie Savitz, and has since raised over $16 million supported by investors like LocalGlobe, CRV, Stage 2, and Jump Capital.
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Topics discussed:
• How crime is a $4 trillion market
• Why 80% of crime is carried out for financial gains
• Why the UN estimates we only catch 0.2% of financial crime
• The reason banks are incentivized to stop fraud, but not crime
• Why it's so hard to stop financial crimes
• How $20B in financial crime was committed on crypto rails in 2022
• What “Synthetic ID Fraud” is, and why it's the fastest growing type of fraud in the US
• What Natasha thinks are the new frontiers of fraud
• Joining Monzo as one of the first employees and staying through a $4B valuation
• What it’s like to be fully invested in a startup when you’re not a founder
• Building Cable to enable regulatory and financial crime teams
• Raising a Pre-Seed round and signing the first customer without a product built
• Why compliance officers want to buy complicated products
• How Natasha diversified her cap table, raising a Seed round from CRV and a group of angels with broad skill sets, ethnicity, race, and sexuality
• How she got two funds to pre-empt her Series A
• Why founding a startup means getting punched in the face every day, and her biggest mistake is not enjoying the little things sooner
• The two founders she most looks up to
• The one interview question she asks every candidate at Cable
Referenced:
• Cable’s site: https://cable.tech
• Cable’s Seed round: https://community.cable.tech/weve-raised-5-3m-from-crv-localglobe-and-a-diverse-group-of-exceptional-angels/
• How They Built the Hoover Dam (Part 1): https://www.youtube.com/watch?v=rXFjLaUxpaw
• How Vegas Became VEGAS (Part 2): https://www.youtube.com/watch?v=3QNuYHEzS2o
Where to find Natasha:
• Twitter: https://twitter.com/natashavernier
• LinkedIn: https://www.linkedin.com/in/natashavernier
Where to find Turner:
• Newsletter: https://www.thespl.it
• Twitter: https://twitter.com/TurnerNovak
Production and distribution by: https://www.supermix.io
Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Growing Deel to $300M+ ARR in Four Years with Co-founder and CEO Alex Bouaziz
Alex Bouaziz is the Co-founder and CEO of Deel, a full stack global HR and payroll platform. But the company didn’t start that way, and we’ll talk through Alex and his co-founder Shuo’s journey from zero to one, starting with a product that helped startups hire international employees.
Alex and Shuo launched the company one week before YC Demo day in 2019, and have since scaled to 20,000+ customers and raised over $685 million. They’re supported by investors like YC, a16z, Spark Capital, Weekend Fund, Coatue, SV Angel, Soma Capital, Quiet Capital, and angels like Lachy Groom, Nat Friedman, Ryan Petersen, Alexis Ohanian, John Zimmer, Dara Khosrowshahi, Rex Salisbury, Justin Mateen, and more.
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In this episode, we discuss:
• The initial insight around remote work that started Deel in 2019
• How they initially built the wrong solution
• Pivoting one week before YC demo day
• Listening to customers to build a better product
• Growing 20% every month for a year
• Being a default optimist
• Dealing with the emotional ups and downs of building a startup
• Moving at “Deel Speed”, and how the team operates so fast
• Deel’s remote-first approach and its “WeWork Squads”
• His advice to other leaders building remote teams
• Why founders shouldn’t share too much information with early investors
• How Alex’s approach to fundraising changed through his Seed to Series D rounds
• Why founders should always be selling their product
• How picking board members is a form of marriage, and what founders should prioritize when picking them
• Why Deel raised a Series A and B in a three month span despite only burning $300k since closing its Seed round
• How deep pocketed investors unlock optionality as a company scales
• The benefits to taking on lots of angel investors
• How Deel prioritized international expansion as it grew
• Deel’s new Visa / immigration and HR AI products
• Two things Alex would do differently if he could start over
• The founders he most looks up to
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Read the transcript: https://www.thespl.it/p/growing-deel-to-300m-arr-in-four
Where to find Alex:
Twitter: https://twitter.com/Bouazizalex
LinkedIn: https://www.linkedin.com/in/alexbouaziz/
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Production and distribution by: https://www.supermix.io
For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
How Semil Shah Built Haystack
Semil Shah is the Founder of Haystack, an institutional venture capital firm that backs outlier founders at the earliest stages. Semil started Haystack in 2013, and has since invested in X unicorns like DoorDash, Instacart, Figma, HashiCorp, Ironclad, Carta, Applied Intuition, and Opendoor.
This episode takes us behind the scenes of Semil’s two decade journey building Haystack from scratch. We’ll dive into how he raised and deployed each of the first six Haystack funds, including all the mistakes made along the way, plus the details around Haystack’s new $75 million and $25 million funds announced the date this episode was published.
Read Haystack's announcement here: https://semilshah.com/2023/09/10/announcing-haystack-vii-same-model-fresh-funds-and-new-era/
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Listen to my conversation with Immad, the Co-founder and CEO of Mercury:
- Spotify: https://open.spotify.com/episode/24ujuXZ2uws48bvwOh9NcR
- Apple: https://podcasts.apple.com/us/podcast/lessons-from-building-mercury-with-immad-akhund-co/id1694440669?i=1000619360042
Disclaimer: Mercury is a financial technology company, not a bank. Banking services are provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC.
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Topics discussed include:
- Juggling multiple jobs while living paycheck to paycheck his first eight years in Silicon Valley
- Failing to get his first job in venture three times
- Investing in the Seed rounds of unicorns DoorDash, Instacart, Hashicorp, and Envoy within the first six months of starting Haystack
- Why he initially thought Haystack would be a short-term thing
- Turning down multiple lucrative job offers two years in
- How the best LPs evaluate VC funds on the “Entry Ownership to Fund Size” ratio
- Semil’s strategy of “crawl, walk, run” to increase Haystack’s check sizes over time
- The pain he felt failing to hit his target fund size on the first four fundraises and how he handled it
- Why everyone should “pre-market” a fundraise, and how to do it
- The things most founders don’t appreciate about raising a venture fund
- Fighting to invest in Ironclad’s Seed round before he had his next fund raised
- How LPs reference VCs, and how a VC can become referenceable
- Why Haystack Fund IV was the scariest fund to raise
- How Semil builds relationships with LPs
- The hardest questions he faced raising each fund and what other VCs should anticipate while raising their own fund
- How LP investment committees make decisions
- What’s going on behind the scenes at most large venture LPs today
- Why the traditional advice of “finding an anchor LP” makes no sense
- Spilling his secret on the best quarter to fundraise
- Why VCs should fundraise with a hard cap on fund size
- Why every VC should appreciate and remember how LPs supported them through the pandemic
- All the details on Haystack’s new $75 million and $25 million funds
- Semil’s plan for the next 10 years
- Three pieces of advice for emerging fund managers
Where to find Semil:
- Twitter: https://twitter.com/semil
- LinkedIn: https://www.linkedin.com/in/semilshah/
Where to find Turner:
- Newsletter: https://www.thespl.it
- Twitter: https://twitter.com/TurnerNovak
Production and distribution by: https://www.supermix.io/
For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
🧪 The Einstein of Ecommerce: Bootstrapping to 9-Figures in Revenue with Sean Frank (CEO, Ridge Wallet)
Sean Frank is the CEO of Ridge Wallet, a men’s wallet and accessories brand that does over 9-figures in annual revenue. The company started in 2012 and raised $266,000 in a Kickstarter campaign to sell the first 5,200 wallets. Ridge hasn’t raised a single dollar of outside capital since, and has also expanded into new categories like rings, knives, watches, backpacks, and keys, with dozens of more products coming soon. Sean is known in some circles as the “Einstein of Ecommerce”, and he gives us an inside look at running a consumer brand in 2023.
Brought to you by Packsmith, better fulfillment for growing brands: https://bit.ly/PacksmithBanana
In this episode, we discuss:
- Why wallets are a terrible product category
- How Ridge has 80% gross margins
- Why brands should generally not raise venture capital
- When a founder should step down as CEO, and how to hire a new one
- Why Ridge is one of the top 10 advertisers on Twitter
- When and how to hire a marketing agency
- Why Ridge never raised outside capital
- Closing clients in a 1991 Honda Civic
- A crash course on the men’s and women’s fashion markets
- Why Sean thinks women’s fashion will have 50% return rates this holiday season
- Investing in a watch manufacturer and building a factory in Arizona to vertically integrate
- Why every company needs a core competency
- The simple tech stack Ridge uses to run their business
- Why Crocs is a great business
- Sponsoring 5,000+ influencers
- Why Amazon shut down its private label program and every brand should sell on it
- Why influencer marketing performs so well, and how to start and scale an influencer marketing program
- Why more companies should incorporate creators in their content
- How FTX and other crypto companies inflated influencer marketing prices
- Paying $1,000,000 to hire a creator in-house
- How the Ridge Wallet has saved customers from a bullet and a chainsaw
Where to find Sean:
Twitter: https://twitter.com/SeanEcom
Substack: http://seanecom.substack.com/
Podcast: https://9operators.com/
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Referenced:
https://www.amazon.com/Great-CEO-Within-Tactical-Building-ebook/dp/B07ZLGQZYC
https://www.theloganbartlettshow.com/
https://www.maryruthorganics.com/
Production and distribution by: https://www.supermix.io
For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
Modern Treasury: How to Move Quadrillions of Dollars, with Co-founder and CEO Dimitri Dadiomov
The Business of Newsletters with Kendall Baker, “The Sports Newsletter Guy”
Kendall Baker currently leads Yahoo’s sports newsletter business. In 2017 he launched the first daily sports newsletter called Sports Internet, which he sold to Axios in 2019. Before Sports Internet, he convinced the founders of The Hustle to focus their online tech blog on a daily newsletter, which he wrote for a year and a half. And before The Hustle, he produced SportsCenter at ESPN. He’s spent nearly a decade at the intersection of daily news and sports, and this episode is packed with insights on both.
Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://bit.ly/3OwGdGC
Read the transcript: https://www.thespl.it/p/the-business-of-newsletters
In this episode, we discuss:
- The history of the newsletter industry
- Why the best writers delete more than they write
- How he got on ESPN SportsCenter
- A crash course on the sports media business
- How to write a daily newsletter
- The importance of experimenting
- How he got his first dollar of revenue
- Why Kendall spent $0 on growth
- Selling his “Sports Internet” newsletter to Axios
- Why Adam Silver, commissioner of the NBA, reads Kendall’s writing
- Why Yahoo’s the next rocketship
- The surging momentum in US soccer
- And the most underrated athletes (current and all-time)
Listen on other platforms:
Apple: https://podcasts.apple.com/us/podcast/the-business-of-newsletters-kendall-baker/id1694440669?i=1000624033211
YouTube: https://youtu.be/4es4p7sFMf0
Where to find Kendall:
Twitter https://twitter.com/kendallbaker
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Read the transcript: https://www.thespl.it/p/the-business-of-newsletters
Production and distribution by: https://www.supermix.io
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🏀 How Overtime Grew to 85 Million Fans | Dan Porter (Co-founder and CEO, Overtime)
Dan Porter is the Co-founder and CEO of Overtime, a sports network for the next generation of fans. OT reaches 85 million fans per month and runs a basketball league (Overtime Elite, OTE), a flag football league (OT7), and is launching a boxing league (OTX) the week this episode airs.
Dan started Overtime with his co-founder Zack Weiner in 2016, and has since raised over $215 million. OT is supported by investors like the late ex-NBA Commissioner David Stern, Jeff Bezos, Drake, Carmelo Anthony, Trae Young, over 25 other NBA players, Spark Capital, Redpoint, a16z, Greycroft, Afore Capital, and Banana Capital. [Turner Novak and Banana Capital are investors in Overtime].
Brought to you by Secureframe, the automated compliance platform built by compliance experts: http://bit.ly/3Qk4RNd
In this episode, we discuss:
Read the transcript: https://www.thespl.it/p/how-overtime-grew-to-85-million-fans
Where to find Dan: Twitter: https://twitter.com/tfadp LinkedIn: https://www.linkedin.com/in/danporter/
Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/TurnerNovak
Where to find The Peel: YouTube: https://www.youtube.com/@ThePeelPod Instagram: https://www.instagram.com/ThePeelPod TikTok: https://www.tiktok.com/@ThePeelPodcast
Read the full transcript: https://www.thespl.it/p/how-overtime-grew-to-85-million-fans
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🍫 How to Build a $70 Million Chocolate Factory | Nick Saltarelli (Co-founder, Mid-Day Squares)
🍕 The $1.3 Billion Pizza Business: How Ilir Sela (Founder & CEO, Slice) is Arming the Pizza Rebels
🏥 Making Healthcare a Product, Not a Service | Adrian Aoun (Founder and CEO, Forward)
Lessons From Building Mercury with Immad Akhund (Co-founder and CEO, Mercury)
Immad Akhund is the Co-founder and CEO of Mercury, a digitally native bank for startups. Mercury is supported by investors like a16z, Coatue, CRV, Chapter One, Ryan Peterson, Scott Belsky, Serena Williams, Terrence Rohan, Zach Coelius, Todd Goldberg, and more. Before Mercury, Immad was a part-time partner at YC, co-founded Heyzap which sold for $45 million, and co-founded and scaled Clickpass to millions of users.
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Read the transcript: https://www.thespl.it/p/the-future-of-banking-remote-work
In this episode, we discuss:
- The future of banking
- Why Mercury’s beautiful onboarding was an accident
- Cultural mistakes most startups make
- Two lessons from selling his first company for $45 million
- How to get free legal advice
- Why it’s better to build a network of entrepreneurs than investors
- How to fundraise
- Why its contrarian to start a non-AI company right now
- How Mercury is thinking about AI
- Why each operational team has its own engineering team
- The embarrassing pitch meeting that raised his Series A from a16z
- How crypto used up all its goodwill
- The hiring advice he gives every founder
Where to find Immad:
Twitter: https://twitter.com/immad
LinkedIn: https://www.linkedin.com/in/iakhund
Podcast: https://curiositypodcast.substack.com/
Where to find Turner:
Newsletter: https://www.thespl.it
Twitter: https://twitter.com/TurnerNovak
Mentioned in this episode:
Mercury https://www.mercury.com
The Logan Bartlett Show: https://www.youtube.com/watch?v=QcL_cjZDeFU
Timestamps:
(0:00) Intro
(5:58) Mercury's "accidentally great" onboarding experience
(8:13) The fundamental banking business model
(9:34) The basics of banking regulation
(11:07) How Mercury works with banks
(13:27) The future of banking
(19:34) Immad's previous startups
(22:30) What culture actually means
(27:06) Importance of ideas vs execution
(32:03) Learning banking from scratch
(35:54) Why the first banking partnership failed
(37:56) Why the second banking partnership worked
(39:24) The difference between compliance and risk teams
(42:08) Why compliance is so relevant for better banking
(50:13) The biggest mistake for doing remote work
(51:21) Mercury Raise
(53:33) The game theory of fundraising
(54:54) Playbook for generating fundraising momentum
(60:45) Common fundraising mistakes
(63:12) Hilarious fundraising mishap in front of a16z
(68:16) Companies that aren't like this shouldn't touch AI
(70:57) Who will win big from AI?
(72:10) Immad's take on crypto
(86:14) Outro
Read the transcript: https://www.thespl.it/p/the-future-of-banking-remote-work Production and distribution by: https://www.supermix.io For sponsorship inquiries: https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform
How Primer Turns Teachers Into Superheroes | Ryan Delk (Co-founder and CEO, Primer)
Ryan Delk is the Co-Founder and CEO of Primer, a startup helping ambitious kids unlock their potential by empowering teachers to launch and run their own micro-schools. Primer’s supported by investors like Founders Fund, Khosla Ventures, Village Global, Susa Ventures, Sam Altman, Naval, Ryan Peterson, Amjad Masad, Julie Zhuo, Tobias Lutke, Lachy Groom, Howie Liu, Dylan Field, Packy McCormick, and many more. Before Primer, Ryan was the COO at peer-to-peer rental marketplace Omni (sold to Coinbase), and prior to that led Growth and Partnerships at Gumroad from $10,000 to $50 million in GMV. Brought to you by Secureframe, the automated compliance platform built by compliance experts: https://secureframe.com/request-demo-4?utm_source=partner&utm_medium=newsletter&utm_campaign=062023-thesplit
Read the transcript: https://www.thespl.it/p/turning-techers-into-superheroes In this episode, we discuss: - How the $1 trillion US K-12 education system works - The broken incentive structures in education - Why teachers are superheroes - How to double a teacher’s income - Primer’s origin story - How to open a school - If online school works - Why founders make the best employees - How the US government wastes billions of dollars - Why everyone should care more about local politics Where to find Ryan: Twitter https://twitter.com/delk LinkedIn: https://www.linkedin.com/in/delk/
Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Timestamps: (3:42) The state of K-12 education in the US (6:35) The structural problem causing a radical misallocation of resources (8:00) The importance of teachers (9:34) The “totally flipped” incentive structure for teachers (12:22) The problem of bureaucracy in education (13:38) Primer’s thesis (14:52) How to start a school (16:00) How Primer helps teachers start their own schools (18:20) Using underutilized real estate to host micro-schools (20:05) Ryan’s take on digital vs in-person learning (21:59) How Primer supports teachers (23:21) Inspirational stories from Primer users (28:00) The underestimated entrepreneurship of teachers (29:12) How Primer stays affordable for all users (30:26) How Primer gets teachers on board (32:04) The role of after-school activities (33:07) How Primer sets its Curriculum (35:14) Ryan’s unique education and how it inspired Primer (38:39) Why someone hadn’t solved this problem yet (40:24) Primer’s initial strategy (41:30) The breakfast that changed everything (42:09) The concept of “Barrels” from Keith Rabois (42:36) Finding and recruiting Ian Bravo (43:31) How Primer recruits ex-founders (44:52) The 3 things Primer screens for in teachers (46:27) What Primer messed up when launching (48:19) Re-thinking school admissions from first principles (51:03) How they convinced the very first teachers to try Primer (51:59) The ineffective usage of education spending (53:28) Policymakers prioritizing “signal over outcomes” (57:21) The worst public schools are worse than you think (59:08) How the Government wastes billions of dollars and Ryan’s idea for solving this (61:31) The importance of increasing engagement with local politics (63:37) The vision for Primer
Read the transcript: https://www.thespl.it/p/turning-techers-into-superheroes
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Selling $100 Million in Dog Collars | Ken Ehrman (Co-founder, Halo Collar)
Ken Ehrman is the co-founder and Managing Partner of Halo Collar, a smart dog collar that tracks your dog with GPS. Halo Collar uses patented technology that allows customers to instantly create up to 20 unique virtual dog fences from their phone using GPS.
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Read the transcript: https://www.thespl.it/p/the-iphone-for-your-dog-ken-ehrman
In this episode, we discuss: - Working for Mike Markkula, the first investor in Apple - Building hardware and the importance of patents - Listening to customers, solving their problems, and sizing a market - Qualifying enterprise customers and selling with "calm confidence." - Early investors trying to buy 95% of his first company - Getting the US Post Office and Army to fund $15 million in R&D - Taking a company public in 1999 with $3 million in revenue - Using AI to train dog movements and make "the Apple Watch" for dogs - The crazy story of how he met his celebrity co-founder, Cesar Millan the Dog Whisperer - What happened when they met famous TikToker Charli D'Amelio Where to find Ken: LinkedIn: https://www.linkedin.com/in/ken-ehrman
Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak
Referenced: Buy the Halo Collar: https://www.halocollar.com/ Cesar Millan, 'the Dog Whisperer': https://www.cesarsway.com/ More on RFID tags: https://www.youtube.com/watch?v=Ukfpq71BoMo&ab_channel=ALLABOUTELECTRONICS Read the transcript: https://www.thespl.it/p/the-iphone-for-your-dog-ken-ehrman
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Sweetgreen: Building McDonald’s for the Next Generation, with Jonathan Neman (Co-founder and CEO)
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