Horizons Pod with Nate Desmond

Listen now on YouTube, Spotify, and Apple.

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Leslie Venetz is a respected B2B sales strategist, keynote speaker, and the founder of The Sales-Led GTM Agency. With 15+ years of experience as a top-performing B2B sales professional and three-time Head of Sales, Leslie has established herself as an authority on outbound sales, email strategy, and creating buyer-centric sales experiences.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 The Money Myth: Top sellers aren't primarily motivated by commission• Once basic financial needs are met, money drops to 3rd-5th priority• Recognition, meaningful work, and team culture rank higher• Key insight: Build incentive structures around more than just cash2/ 🎧 Active Listening > Passive Silence • It's not just about not interrupting• Resist the urge to pre-plan your response• Focus on understanding vs. sharing your "similar story"• Use the 4R framework (including Resist) to improve listening skills3/ 💪 Earn The Right Before You Sell• Start by providing value before asking for attention• Apply this mindset to every interaction (emails, calls, meetings)• Test: "What have I done to earn the right to make this ask?"4/ 📊 Quality > Quantity for Account Load• Enterprise/ABM: ~50 accounts per rep• Transactional sales: 400-500 accounts• Work backward from revenue goals to determine actual needs5/ 🎯 Incentive Design Drives Behavior• Make quota attainment feel achievable• Structure bigger payouts at higher performance tiers• Allow reps breathing room for strategic territory management6/ 🤝 Marketing vs Sales: Partners Not Nemeses• Both face rejection and campaign failures• Attribution battles usually stem from executive pressure• Best results come from true cross-functional collaboration7/ 📝 Cold Email Excellence = Reduced Cognitive Load• Write at 3rd-5th grade reading level• Create visual space in messages• Make calls-to-action crystal clear• Focus on relevance to recipient8/ 📈 Product Led vs Sales Led: Choose Based on Price• PLG works best for products <$200/month• Higher price points justify full sales motion• Consider hybrid approach as you scale

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Where to find Leslie Venetz:

* The Sales-Led GTM Agency: https://salesledgtm.com/

* LinkedIn: https://www.linkedin.com/in/leslievenetz/

* X: https://x.com/B2B_SalesCoach

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In this episode, we cover:

00:00 Leslie Venetz: Journey to Sales Leadership 01:46 Understanding Sales as a Helping Profession 06:45 Lessons from Early Sales Jobs 10:55 Navigating Product-Market Fit Challenges 16:46 Sales Strategies for Growth 19:51 Finding Product-Market Fit 24:36 The Art of Cold Outreach 32:35 Multi-Channel Sales Outreach Strategies 36:18 Multi-Channel Outreach Strategy 38:09 The Importance of Data Providers 39:43 Understanding Customer Acquisition Costs 42:41 Sales Development Rep Workload 46:25 Backtracking to Revenue Goals 48:05 The Misconceptions of Sales Motivation 51:17 Motivating Sales Teams Beyond Money 53:10 The Power of Active Listening 57:48 Incentive Design for Sales Teams 01:02:51 Earning the Right to Ask 01:06:55 The Role of MQLs in Sales

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Sam Preston is the CEO of Service Scalers, a specialized marketing agency focused on helping home service businesses grow through digital marketing.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Your numbers tell the real story > Your gut instincts- Track the full funnel: leads → appointments → deals → revenue- One client went from $200k to $10M after switching budget between keywords based on revenue data (not just lead volume)- Key metrics: lead volume, appointment rate, close rate, revenue per lead source2/ 📞 Phone Calls > Form Fills for Service Businesses - Get prospects on the phone to build rapport and set appointments- Use call tracking numbers to attribute leads to marketing channels- Consider tools like CallRail to dynamically swap numbers based on traffic source3/ 🤝 Annual Contracts > Monthly Retainers- Predictable revenue enables hiring better talent- Better talent drives better results for clients- Creates positive feedback loop of growth- Similar to how service businesses can benefit from maintenance packages4/ 👥 Hiring Philosophy: Values + Skills > Just Skills- Key interview questions reveal values alignment:- "What rule did you break at your last job?"- "When have you put your job at jeopardy?"- Look for people willing to do the right thing, even when difficult5/ 🎨 Simple Website > Fancy Design- Clear services and location- Strong call-to-actions (not "Learn More")- Basic social proof- Job-to-be-done focused copy- Mobile-first design with persistent click-to-call6/ 🔄 Test Lead Sources Before Scaling- Start with Facebook groups for free leads- Graduate to aggregators for paid leads- Move to Google Ads once you have budget- Add broader marketing channels at scale7/ 💼 Perfect Agency Partnership = High Standards + Good Treatment- Don't just "pay and get out of the way"- Don't micromanage either- Hold accountable while treating team well- Think of agency as extension of your team8/ 🎯 Track Metrics That Matter- Lead source performance (volume AND revenue)- Appointment set rate- Close rate- Return on ad spend- Give every role ONE key metric to optimize

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Where to find Sam Preston:

* Service Scalers: https://www.servicescalers.com/

* LinkedIn: https://www.linkedin.com/in/sampreston/

* X: https://x.com/HeySamPreston

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In this episode, we cover:

00:00 Introduction and Personal Insights 00:52 Understanding Home Service Businesses 06:56 Marketing Strategies for Home Service Businesses 15:03 Hiring and Budgeting for Marketing 21:41 Tracking Leads and Optimizing Websites 25:22 Effective Marketing Strategies for Home Services 27:12 The Power of Story Branding 29:23 Converting Leads into Sales 31:40 The Importance of First Impressions 33:36 Optimizing for Mobile Experience 34:38 Understanding Jobs to Be Done 36:15 The Role of Social Proof 38:13 Scaling a Home Service Business 39:25 Hiring for Growth 42:15 Identifying the Right Talent 48:42 Creating a Positive Work Culture 51:49 Balancing Automation and Hiring 55:30 Tailoring Marketing Strategies for Home Services 58:17 The Importance of Client Retention and Revenue Predictability 01:01:13 Creating Recurring Revenue Streams in Home Services 01:04:19 Managing Staffing and Demand in Service Businesses 01:05:31 Identifying Pain Points for Business Growth 01:09:02 Building Effective Partnerships with Agencies 01:11:39 Key Performance Indicators for Home Service Businesses

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Brian Austgen is the Director of Demand Generation at Maxio, a B2B billing and financial reporting platform, and has over a decade of experience in digital marketing. (including a time when we both worked at the same education technology company)

Here’s some of my takeaways from this week’s episode…

1/ 🚀 The best-performing B2B marketing channel in 2025? Webinars. At $20k per event, they're delivering 4x expected results. Pro tip: Focus on timely messaging + strong partners/influencers + strategic promotion timing2/ 🎯 Your budget = your strategy. When allocating funds, map spending to company goals first, then use data for established channels and gut instinct (backed by experience) for new ones3/ 🧠 Want better marketing instincts? Test with discipline. Set clear hypotheses, define success metrics upfront, and ensure failures create actionable feedback → knowledge → power4/ 🤝 Agency management golden rule: If you're constantly pushing back on their recommendations, you've either hired the wrong agency or you're being stupid. They should drive strategy while you provide context5/ 📊 PLG (Product Led Growth) is transforming B2B marketing. Converting users to a free trial > booking sales calls. Focus on the first 2 minutes of product experience to start the flywheel6/ 🎨 Color testing in ads is surprisingly impactful. Simple color changes can dramatically affect performance - sometimes more than messaging tweaks7/ 🤖 AI sweet spots: Creative asset generation, video editing, and campaign planning. But garbage in = garbage out. Experienced marketers get better AI outputs because they feed it better inputs8/ 🎯 Top B2B marketing mistake? Assuming what worked before will keep working. Great marketers have multiple playbooks ready when the current one stops performing

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Where to find Brian Austgen:

* Maxio billing software: https://www.maxio.com/

* LinkedIn: https://www.linkedin.com/in/brianaustgen/

* X: https://x.com/brianaustgen

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In this episode, we cover:

00:00 Introduction and Setup 01:41 Undervalued Marketing Channels 05:26 Balancing Focus and Experimentation 08:06 Improving Marketing Intuition 09:12 Testing Methodologies in Marketing 09:42 Leveraging Data for Marketing Decisions 19:09 The Power of Webinars in Marketing 28:28 Building Credibility in Leadership 36:16 Navigating Rebranding Challenges 43:26 Building an Effective Marketing Team 46:22 Navigating Agency Relationships 49:33 Managing Agency vs. Direct Reports 53:56 Impressing Leadership as an Employee 55:49 Best Practices for Agency Interactions 57:53 Strategic Marketing Allocation 01:00:58 Common Growth Mistakes in Scaling 01:03:58 Sales and Marketing Alignment 01:08:04 B2B vs. B2C Marketing Dynamics

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Jacqueline Freedman is the CEO and Founder of Monarch Advisory Partners, a full-stack marketing consultancy specializing in GTM, MarOps, and MarTech. Prior to launching her consultancy, Jacqueline was the 5th marketing hire at WeWork during their hypergrowth phase and the 1st Marketing Operations hire at Grammarly during their transition to a B2C2B model.

Here’s some of my takeaways from this week’s episode…

1/ 📊 Process trumps perfection: When scaling marketing ops, focus on creating foolproof processes rather than expecting perfect execution. Create clear documentation, role-based access controls, and simplified workflows that even non-marketers can follow successfully.2/ 🎯 Community over metrics: Sometimes the most valuable marketing initiatives don't have clear KPIs. WeWork's building newsletters focused on community-building rather than specific metrics, showing how brand value can outweigh immediate measurable results.3/ 🔄 Post-mortems are gold mines: After mistakes, focus on "what happened, how it happened, why it happened, and how to prevent it." Document learnings and use them to improve processes. The response to failure matters more than the failure itself.4/ 💰 Daily data syncs = massive savings: Small operational improvements can yield huge returns at scale. Example: Updating paid ad suppression lists daily instead of monthly saved millions in ad spend by preventing mistargeting of existing customers.5/ 🎨 B2B doesn't mean boring: B2B companies can (and should) be more playful with their brand voice. While you don't need to chase every trend, establish a clear brand persona and don't default to overly formal communication.6/ 📈 Personalization needs substance: Move beyond basic "{first_name}" personalization. Focus on meaningful data points that provide value to users, while being mindful of privacy boundaries.7/ 🤝 Vendor partnerships matter: Build strong relationships with your marketing tech vendors. Join customer advisory boards and provide detailed feedback - you know the problems, they know how to build solutions.8/ 👥 Cross-functional translation is key: Marketing ops pros must be "global translators" between teams. Success comes from ability to communicate technical concepts to non-technical stakeholders and vice versa.

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Where to find Jacqueline Freedman:

* Monarch Advisory Partners: https://www.monarchadvisorypartners.com/

* The Martech Weekly: https://themartechweekly.com/

* LinkedIn: https://www.linkedin.com/in/jacquelinefreedman/

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In this episode, we cover:

00:00 Optimizing Ad Spend & Intro Jacqueline Freedman 01:11 Early Career: Jacq of All Trades & Remote Work Pioneer 02:58 Scaling WeWork's Hyper-Localized Newsletters (500 Buildings!) 04:22 The "Why" Behind WeWork's Emails: Community Over KPIs 06:16 The Unmeasurable Value of Brand Marketing 07:33 The Tech & Process Behind 500 Weekly Emails 09:30 Empowering 500 Non-Marketers to Be Marketers 11:46 Hyper-Localization: Beyond Countries to Buildings 13:09 Joining Grammarly: Building B2B Marketing Ops from Scratch 15:00 Hot Take: Why MQLs Aren't Dead (If Done Right) 19:19 Defining Your Ideal Customer Profile (ICP) 22:08 Grammarly's B2C to B2B Pivot: Finding the New ICP 24:15 AI in Writing: Tool, Threat, or Transformation? 26:54 Grandfather's Wisdom: Clients & Stakeholders Make or Break Your Day 27:30 The Power of Stakeholder Relationships & Listening Tours 30:16 Bridging the Gap: Marketing & Engineering Collaboration 33:02 Being "Dangerously" Technical as a Marketer 37:06 Facing Pay Inequity & Advocating for Fair Compensation 39:23 The Art & Discomfort of Negotiating for Yourself 43:06 Confessions of a Recovering Workaholic: Boundaries & Balance 45:35 Learning from Mistakes: A Post-Mortem Tale ("Winner of AB Test Here") 51:28 Blameless Post-Mortems & Process Improvement Culture 53:15 How You Leave Matters: Employees & Unsubscribers 55:58 Beyond First Names: Creating Impactful, Personalized Campaigns (WeWork Year in Review) 1:01:37 Should B2B Brands Be More Playful? 1:03:57 Saving Millions: Daily Data Syncs & Ad Suppression at Grammarly 1:08:07 Partnering with Vendors to Shape MarTech's Future 1:10:10 Where to Find Jacqueline & Final Thoughts

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Alexey Komissarouk is a growth engineering pioneer who's generated hundreds of millions in revenue through data-driven experimentation at companies like MasterClass and Opendoor.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Good friction > No frictionWhen done right, adding strategic friction (like onboarding quizzes) can actually increase conversion by building user intent. MasterClass saw this when they made users go through a quiz that showcased their full content library before hitting the $180 price tag.2/ 📊 Simple metrics > Complex metrics The best metrics are trivially explainable. While it's tempting to create complex formulas that capture every edge case, stick to metrics that everyone can understand and act on. MasterClass used "expected LTV per homepage visit" - sophisticated but still clear.3/ 🧪 Pattern matching > First principlesDon't waste time reinventing the wheel. Start by copying what works in your industry - the win rate on proven tactics is much higher than novel ideas. Once you've exhausted the obvious wins, then innovate.4/ 🚪 Fake doors unlock real insightsWhen testing major changes (like pricing), use creative "fake door" tests. MasterClass tested lower price tiers by showing them but upgrading users to premium "for free" - getting real data without the engineering investment.5/ 📈 Process > OutcomesCelebrate velocity and good experiment design over wins. Build a culture that praises rapid iteration and learning rather than just successful tests. This keeps teams motivated through the inevitable failures.6/ 🎯 Structured decisions > Gut callsUse formal prioritization frameworks (like RICE) to evaluate experiments. This makes decision-making transparent, coachable, and helps surface non-obvious winners that might get overlooked.7/ 🔍 Business metrics > Vanity metricsDon't trust surface-level engagement metrics (opens, clicks). One push notification test looked like a 10% loser on engagement but drove 10% more orders. Always measure what matters to the business.8/ 👥 Leadership taste > Perfect metricsWhile good metrics matter, having leadership with strong product taste is crucial for maintaining quality. The best defense against growth tactics degrading product quality is experienced leaders who can spot and stop harmful optimization.

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Where to find Alexey Komissarouk:

* Blog: https://alexeymk.com/

* LinkedIn: https://www.linkedin.com/in/alexeymk/

* X: https://x.com/alexeymk

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In this episode, we cover:

00:00 Introduction and Background 01:15 Experimentation and Growth Engineering 01:33 Measuring Experiment Success 04:22 Defining Growth Engineering 07:15 When to Hire Growth Engineers 26:55 Understanding SaaS Business Metrics 28:06 Industry Variations in Growth Strategies 29:59 Navigating Regulatory Challenges in Growth Engineering 30:40 The Intersection of Marketing and Engineering 34:26 Skills for Growth Engineering 36:19 Learning from Others in Growth Engineering 39:22 Counterintuitive Experiment Results 41:56 The Importance of Metrics in Marketing 44:33 Incentive Design in Business 46:51 Leadership and Quality Control in Growth Engineering 49:09 Balancing Short-Term and Long-Term Goals 51:35 Building a Culture of Experimentation 57:46 Innovative Pricing Strategies 01:02:05 Growth Engineering Beyond Subscriptions

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Mike Taylor is the CEO and Co-Founder of Rally, an AI audience simulation platform that allows marketers to run synthetic focus groups. Before founding Rally, Mike co-founded Ladder, a 50-person growth marketing agency, as well as Vexpower, a simulation-based learning platform for marketers.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Live in the Future, Act in the PresentThe future exists, it's just not evenly distributed. Make intentional trips to tech hubs like SF/NYC to soak up emerging trends, then bring those insights back home. You don't need to live there, but you do need to visit regularly.2/ 💰 Status vs. Money: Choose Your PathWant status? Get in super early. Want profit? Join right before mainstream. But always optimize for money first—it buys freedom to pursue what truly interests you later. The sweet spot is often right before mass adoption.3/ 🤖 AI Automation = Creative Freedom When you automate the mundane parts of your job, you have two choices: work less or work on more interesting things. The real opportunity is using that freed-up time to pursue creative projects that AI can't replicate.4/ 🎯 The NCO EffectPosition yourself as the "non-commissioned officer" between AI strategy and execution. Humans excel at making creative, contextual decisions that bridge high-level planning and ground-level implementation.5/ 📝 Content Marketing 2.0The future isn't about pumping out 3500-word SEO articles—AI can do that. Success lies in finding and amplifying authentic stories, acting more like a journalist than a content factory.6/ 🎨 Test Small, Scale SmartStart by doing things manually, then automate once you've proven the process works. The progression: Do it manually → Create saved prompts → Automate with no-code tools → Build custom solutions.7/ 🎯 The 60/90 RuleBlog posts drove 60% of direct leads but influenced 90% of all deals. Don't write for decision-makers—write for the experts who influence them. Your content builds credibility with the recommenders.8/ 🤝 Network Like a ConnectorEvents aren't about meeting clients directly—they're about meeting people who know potential clients. Focus on being someone others are excited to recommend rather than selling directly.

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Where to find Mike Taylor:

* Rally: https://askrally.com/

* LinkedIn: https://www.linkedin.com/in/mjt145/

* X: https://x.com/hammer_mt

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In this episode, we cover:

00:00 Intro and Welcome 00:39 The Journey into AI and Marketing 03:23 Navigating the AI Landscape 06:17 Status vs. Money in Business 09:06 The Birth of Rally 12:30 Understanding Rally's Purpose and Functionality 25:10 Experimenting with AI and Predicting Viral Headlines 27:59 Understanding Human Behavior Through AI 29:51 The Art of Prompt Engineering 37:04 Building an Uno Game with AI 45:55 Automating Tasks with AI 52:52 The Future of Creativity and AI 58:19 Value-Based Pricing and Client Perceptions 01:00:22 Automation and Freedom in Writing 01:01:17 AI's Role in Marketing Synthesis 01:03:29 The Future of Marketing Roles 01:07:45 The Evolution of Marketing Strategies 01:11:23 Insights from Working with Major Brands 01:17:07 Creative Hiring Strategies for Agencies

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Ryan Delk is the CEO and Founder of Primer, a platform that helps the top 1% of teachers launch microschools in their communities, and he’s spent the last decade building tech companies like Square, Gumroad, and Omni.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 High Agency > High Experience: The best leaders aren't just experienced—they believe they can shape outcomes through action. Look for people who take ownership and drive results, regardless of their background or years of experience.

2/ 🔄 Unit Economics Are Physics: No amount of growth can overcome broken unit economics. At Omni, even with best-in-class optimization, delivery costs couldn't compete with Amazon-normalized pricing expectations. Know your numbers before scaling.

3/ 🎓 Teachers Are Natural Entrepreneurs: Great educators already have key founder traits—managing ""customers"" (parents), handling budgets, and leading teams. The key is giving them tools and removing bureaucracy to let their entrepreneurial spirit thrive.

4/ 🔍 Talent Discovery > Talent Competition: Build structural advantages by finding exceptional people from non-traditional backgrounds. Focus on undiscovered talent (young or career-switchers) rather than competing for the same Stanford/Google pool.

5/ 🏗️ Market Problems Need Market-Level Solutions: When facing regulatory roadblocks, sometimes you need to change the system instead of just working within it. Primer's success in changing Florida education law shows the power of tackling root causes.

6/ 💪 Quality Control Through Technology: Scale quality by building systems that automate quality control. Primer's platform tracks learning velocity and suggests corrections, allowing less-experienced teachers to deliver consistent results.

7/ ⚡ Speed vs. Quality is a False Choice: Top performers can maintain extremely high quality while moving quickly. The key is finding truly exceptional people and giving them the tools and autonomy to execute.

8/ 🎯 Mission Drives Retention: When tackling universal problems few are addressing (like education), mission alignment becomes your strongest retention tool. Top talent will choose impact over traditional career paths when given real agency to drive change.

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Where to find Ryan Delk:

* Primer Microschools: https://primer.com/

* LinkedIn: https://www.linkedin.com/in/delk/

* X: https://x.com/delk

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In this episode, we cover:

00:00 The Journey Begins: From Banking to Tech 05:07 Square's Hyper-Growth: Lessons Learned 09:27 The Talent Advantage: Attracting Undiscovered Talent 14:24 Building a Team: The Importance of Barrels 20:32 Gumroad: Navigating Growth and Pricing Strategies 27:08 The Indie Creator Movement: Word of Mouth Success 37:21 Sustainable Growth: Avoiding Reliance on Big Launches 37:35 Navigating Different Business Models 38:58 Lessons from Building Omni 42:17 The Trojan Horse of Rentals 45:09 Customer Acquisition Strategies 48:15 Understanding Business Equations 49:56 The Birth of Primer 53:09 Pivoting to Micro Schools 56:58 The Entrepreneurial Spirit of Teachers 59:31 High Agency in Education 01:02:23 Lightning Round

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Jesse Hanley is a marketer-turned-founder who went from running digital marketing at Gold's Gym Australia to building Bento, where he's proving that email marketing platforms don't need venture funding or aggressive growth to deliver enterprise-grade capabilities.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Keep It Simple, Keep It Consistent: The most profitable email accounts aren't complex snake-tree automations—they're ""caveman"" approaches focused on consistent, valuable communication. Success comes from knowing your customers well and maintaining regular touchpoints.

2/ 🧪 A/B Testing Is Often Busy Work: Most A/B testing in email marketing suffers from flawed metrics (like open rates affected by bots) and insufficient sample sizes. Focus on revenue and conversions instead of getting lost in headline optimization.

3/ 📈 North Star = ""Expected & Wanted"": Every email decision should pass two tests: Do users expect this email? Do they want it? This simple framework helps cut through the noise on everything from image usage to send frequency.

4/ 🎭 Brand > Performance Marketing: While performance metrics matter, brand-building through multiple channels creates compound effects. Don't dismiss ""old school"" marketing—conferences, sponsorships, and broad brand presence often drive unexpected value.

5/ 🎨 Personalization Is Often Overkill: For most businesses (especially with <10k subscribers), complex personalization flows aren't worth the effort. Focus on nailing the basics: clear welcome series, consistent newsletters, and timely transactional emails.

6/ 🎯 Measure What Matters: Skip vanity metrics like open rates. Focus on concrete business outcomes: credit card signups, revenue, or specific conversion actions that tie directly to business growth.

7/ 🤖 AI Should Enhance, Not Replace: The best AI implementations subtly improve existing workflows rather than creating flashy new features. Focus on reducing friction in common tasks versus building AI-powered bells and whistles.

8/ 📊 Quality > Quantity in List Building: Resist the urge to rapidly scale your email list through paid growth or cross-promotion networks. A smaller, highly-engaged list often drives more revenue than a large, unengaged one.

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Where to find Jesse Hanley:

* Bento: https://bentonow.com/

* LinkedIn: https://www.linkedin.com/in/jessehanley/

* X: https://x.com/jessethanley/

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In this episode, we cover:

00:00 Introduction and Backgrounds 05:09 The Journey of Learning to Code 15:08 Building Bento and Early Challenges 25:40 Customer Engagement and Support Strategies 27:31 Crafting Effective Marketing Emails 35:38 Balancing Marketing Strategies for Growth 41:27 The Art of Personalization in Email Marketing 50:06 Metrics That Matter: Evaluating Email Campaign Success 55:31 Balancing Value and Promotion in Email Content 58:09 Scaling Email Marketing Efforts Effectively 01:05:42 Integrating AI for Enhanced Email Marketing

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Maja Voje is the author of Go-To-Market Strategist and founder of Growth Lab, both of which build on her experience with 400+ launches across hundreds of companies.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Early Customer Profile > Ideal Customer Profile• Your first 50 customers won't be your ideal ones - and that's OK• Focus on finding customers with: burning pain points, willingness to pay now, adjacency to ideal customers, and low barriers to entry• Start with segments you can actually access and understand, then move upmarket2/ 🧪 Test, Don't Guess• Run actual experiments instead of endless analysis• Use ads to test messaging even before website traffic• Test one variable at a time (positioning, pricing, etc.)• When in doubt, talk to 5-10 customers3/ 💰 Price for Value, Not Competition• Capture 20-30% of the value you create• Start with competitor benchmarking if needed• For AI products, benchmark against human alternatives• Don't waste time finding the "perfect" price before having customers4/ 🎥 Social Proof is Your Best Bet• Real customer testimonials matter more than ever in the AI era• Record testimonials at events when possible• Focus on showing authentic enthusiasm and results• Use this as your first major testing variable5/ 🔄 Seven Go-to-Market Motions• Inbound (content, organic)• Paid acquisition• Outreach/sales• Community building• Account-based marketing• Product-led growth• Events/partnerships6/ 📞 Cold Outreach Still Works• Use data enrichment for mass personalization• Reference specific details about prospects• Start with warm outreach on LinkedIn• Focus on adding value before pitching7/ 🎮 Make Products "Perfect Enough"• For AI products, go beyond bare MVP• Focus on core value delivery• Ensure first impression drives retention• Test with high-touch onboarding initially8/ 📈 When to Add New Channels• When seeing diminishing returns in primary channel• When introducing new products/price points• When entering new market segments• Consider hiring experts vs learning yourself

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Where to find Maja Voje:

* Maja’s free GTM checklist: https://gtmstrategist.com/gtm-checklist

* LinkedIn: https://www.linkedin.com/in/majavoje/

* X: https://x.com/majavoje

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In this episode, we cover:

00:00 Introduction to Go-To-Market Strategies 01:39 Shifts in Go-To-Market Approaches 07:14 Identifying Product-Market Fit 12:16 Understanding Customer Profiles 16:54 Case Study: Loom's Customer Profile 23:17 Overcoming Analysis Paralysis 31:13 The Power of Cold Outreach 42:19 Pricing Strategies for Startups 47:13 Proof of Product-Market Fit 53:06 Handling Failure and Learning 56:38 Structuring Experiments for Results 01:01:32 When to Level Up Growth Strategies 01:05:12 Lightning Round: Quick Decisions

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Sherry Jiang is the founder and CEO of Peek, an AI-powered personal finance platform helping users track and grow their net worth. Previously at Google, where she worked on Google Pay's growth in India, Sherry made the bold decision to leave big tech in 2021 to pursue entrepreneurship in Singapore.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Master One Channel Before ScalingThe first $1M in revenue can come from mastering a single marketing channel. Don't spread yourself too thin across multiple platforms—go deep before going wide. For Peek, LinkedIn organic was the golden ticket, driving hundreds of beta signups through authentic storytelling.2/ 🧪 Right-Size Your ExperimentsThink like a poker player: Make small bets to test hypotheses before going all-in. Start with minimal viable experiments that let you validate assumptions without depleting resources. A good rule: If an experiment fails, it shouldn't threaten your core business.3/ 👥 The "15 Core Users" Rule Rather than trying to deeply understand hundreds of users, focus on 15 power users you know "as well as your siblings." Look for users who proactively provide feedback and engage with your product—they'll give you the insights needed to build something great.4/ 📱 Prototype > PerfectBuild quick, throwaway prototypes to validate ideas fast. One prototype per month is a good cadence. Don't worry about perfect branding or polish—focus on getting behavioral validation from real users. As Sherry says, "I don't care if the colors aren't on brand."5/ 💡 Local > Global Don't confuse "US market" with "global." Start with geographic focus and expand strategically. The world has 8B people—the US has 300M. Regional focus lets you deeply understand users and build for their specific needs before expanding.6/ 🎭 AI as Writing PartnerUse AI as a writing assistant and research accelerator, not a replacement. Feed it your "word vomit" and let it help structure thoughts. For research, use it to spot patterns and generate insights that would take humans weeks to compile.7/ 📊 Story > StatsDon't just show data—tell stories with it. Even with limited data (like one month of transactions), you can craft meaningful narratives about spending patterns and behaviors. Focus on progressive revelation of information with clear hooks and resolutions.8/ 🎬 Content Format Follows PlatformDifferent platforms demand different approaches: LinkedIn rewards professional insight, TikTok needs extreme authenticity, Reddit requires pure value-add with zero self-promotion. Don't copy-paste content across platforms—adapt to each one's native language.

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Where to find Sherry Jiang:

* Peek: https://peek.money/

* LinkedIn: https://www.linkedin.com/in/sherrypeek/

* X: https://x.com/SherryYanJiang

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In this episode, we cover:

00:00 Introduction and Background 05:37 Learning AI Coding as a Non-Technical Founder 11:16 Onboarding Challenges in Personal Finance Apps 16:55 User Acquisition and Building Trust 19:51 Understanding the Founder Journey 21:10 Navigating Switching Costs in Startups 22:36 Assessing Product-Market Fit 26:33 The Art and Science of Founding 29:32 Merging Data and Intuition 33:19 Thinking in Bets: Lessons from Poker 36:19 Marketing Strategies and LinkedIn Success 38:30 Building a Personal Brand 44:26 Customer Retention and Insights 49:47 Prototyping and Testing for Product Market Fit 50:59 Channel Optimization Post Product Market Fit 53:15 Localization Strategies for Diverse Markets 55:07 Underrated Marketing Channels: Insights and Opportunities 57:15 The Impact of AI on Personal Finance Management 01:02:50 Lightning Round: Quickfire Marketing Insights

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

—

Gastón is a poetry-obsessed CMO whose marketing campaigns are powered by literature and code - leading him from Google to wonky vegetables, with successful stops at dating apps and AI news along the way.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Brand First, Growth Second: A strong brand narrative naturally drives growth metrics. Don't chase numbers at the expense of story—focus on building a compelling narrative that resonates with your audience and the metrics will follow.2/ 🗣️ Customer Understanding > Dashboard Data: While analytics are valuable, nothing beats direct customer observation and feedback. Post-checkout surveys asking "why did you join?" and "what concerns did you have?" provide deeper insights than surface-level metrics.3/ 🎨 B2B ≠ Boring-to-Boring: Business buyers are humans first. They're thinking about promotions, career growth, and personal success—not your product features. Connect with the human truth behind business decisions.4/ 🔄 Consistency ≠ Repetition: Brand consistency isn't about parroting the same phrases—it's about staying true to core values while varying your expression. Use different words to convey the same meaning to keep messaging fresh and engaging.5/ 🌍 Local > Global in Marketing: When scaling internationally, empower local marketing teams over centralized control. While less efficient, local teams better understand cultural nuances and market opportunities.6/ 💡 Make the Familiar Strange: The best marketing makes familiar things unfamiliar (and vice versa). Like literature, great campaigns help people see everyday things in new ways.7/ 🎭 Values > Neutrality: Don't fall into the trap of neutral, bland messaging when expanding to new markets. Local brands succeed because they speak authentically to their audience.8/ 🎓 Growth vs. Efficiency is a Trade-off: There's no perfect solution in marketing—just trade-offs. Choose whether to optimize for growth (local control, higher costs) or efficiency (central control, lower costs) based on business objectives.

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Where to find Gastón Tourn:

* LinkedIn: https://www.linkedin.com/in/gtourn/

* Oddbox: https://www.oddbox.co.uk/

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In this episode, we cover:

00:00 Introduction and Background 03:20 The Importance of Meaning in Marketing 13:48 Combining Literature and Technology 25:29 Insights from Startup Marketing 28:57 The Importance of Marketing in Product Success 32:03 Cultural Insights in Dating and Marketing 34:11 Challenges of Global Marketing Localization 36:46 The Risks of Big Brand Marketing 39:32 Balancing Centralization and Localization in Marketing 42:04 Trade-offs in Marketing Strategies 46:26 B2B Marketing: Connecting with Real People 48:47 Consistency vs. Repetition in Brand Messaging 54:24 Understanding Customer Motivations at Oddbox 57:13 The Value of Teaching and Learning from Students

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

—

Andrew Littlefield is a content marketing veteran who's helped build audiences from scratch at multiple startups and established brands, including the robotic tiny homes company Ori.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Content Success = More At-BatsThe key to content marketing isn't perfection—it's volume of attempts. Like baseball, even Hall of Famers only succeed 1/3 of the time. Focus on getting more "at-bats" by publishing frequently and experimenting constantly, rather than trying to make every piece perfect.2/ 🌱 Early Success Signs MatterWhen something's really working, you'll often see clear positive signals very early—like unexpectedly high engagement or enthusiastic audience feedback. Don't waste months trying to force mediocre results when you could be exploring new directions.3/ 🎨 Hire for Hunger, Not Credentials Look for candidates who show creativity, attention to detail, and drive to succeed—regardless of their educational background. Hidden application instructions (like "use the word 'wiggle' in your cover letter") help identify detail-oriented folks who'll go the extra mile.4/ 📊 Blog Strategy = Compound InterestDon't chase viral hits. Build a library of solid content that each brings in steady traffic. 100 posts getting 5 views/day > 1 post getting 100 views/day. The cumulative effect compounds over time as your content library grows.5/ 🎬 Search > SocialPrioritize platforms where users actively search for solutions (like YouTube) over pure social feeds. Search-based content has longer shelf life and attracts more intentional audiences seeking specific solutions.6/ 🎭 Gate StrategicallySave gating for truly valuable, exclusive content like live events or original research. The bar for what people will trade their contact info for has risen dramatically—make sure you're offering genuine value.7/ 🔄 Adapt or DieWhat works in content marketing constantly evolves. Be ready to abandon strategies that stop working and experiment with new approaches. Success comes from staying flexible and responsive to changing audience behaviors.8/ 🎯 B2B2C MarketingSometimes the path to B2B success requires building consumer demand first. Create broad awareness and desire for your product among end users to drive business customer adoption.

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Where to find Andrew Littlefield:

* LinkedIn: https://www.linkedin.com/in/andrewlittlefield/

* X: https://x.com/fsuandrew

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In this episode, we cover:

00:00 Introduction and Background 05:26 Early Successes in Marketing 09:05 The Recipe for Success in Content Marketing 15:18 Iterating and Adapting Strategies 16:08 The Addiction of Content Creation 19:50 Navigating the Content Marketing Landscape 22:43 The Art of Experimentation in Marketing 27:01 Overcoming Barriers to Creativity 29:47 Accountability in Pursuing Dreams 35:36 The Early Days of Marketing at We Did It 44:04 The Persistence of Ideas 45:24 Identifying Winning Strategies 47:21 Building a Talented Team 49:34 Innovative Hiring Practices 52:30 The Value of Hunger in Candidates 57:18 Gated vs. Ungated Content 01:03:24 The B2B2C Approach to Marketing 01:03:53 Lightning Round Insights

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Ina Herlihy is the founder and CEO of AddGlow, helping brands increase revenue. They've started with an onsite community. She brings unique insights from building products at Walmart and driving early growth at Zumper.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Rejection builds resilience: Early experiences with rejection (like getting press passes as a teen) can be invaluable training for founder life. The key is viewing rejection as a normal part of the process rather than a roadblock.2/ 🔍 Founder-led sales are crucial early on: Don't delegate sales too quickly in the early stages. Direct customer conversations provide invaluable learning that shapes product development and company direction.3/ 🧪 Test manually before automating: Start with manual processes to validate hypotheses before investing in automation. At Zumper, Ina manually personalized emails first, proved the impact, then found tools to scale it.4/ 🤝 Network effects compound over time: Your professional network isn't just about immediate opportunities—it's about future hires, investors, and advisors. Focus on excellence in your current role to build strong references.5/ 📊 Data capture drives personalization: Collecting first-party data during community signup enables better email personalization and higher revenue. Partner integrations (like with CRMs) multiply the value.6/ 🎨 Default > Custom: Keep user interfaces familiar when possible. Just like how Starbucks uses consistent layouts globally, default reactions/emojis reduce friction and increase engagement.7/ 🔄 Community engagement is a gradual build: Focus first on awareness and accessibility, then layer in engagement drivers like weekly digest emails and point-based rewards with smart limitations.8/ 🎬 Customer promises ≠ commitments: Be wary of building features just because potential customers say they'll buy if you do. Focus on features that benefit multiple customers rather than one-off requests.

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Where to find Ina Herlihy:

* Web: https://addglow.com/

* LinkedIn: https://www.linkedin.com/in/inaherlihy/

* X: https://x.com/inaherlihy

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In this episode, we cover:

00:00 The Journey to Founding AddGlow 07:28 Navigating the Challenges of Entrepreneurship 07:33 Marketing Strategies at Zumper 10:58 Balancing Brand Awareness and Short-Term Performance 10:58 Sales and Customer Engagement Strategies 12:53 User Conversations and Product Development 15:51 Email Marketing Insights from Zumper 17:16 Leadership and Team Development 19:27 Transitioning from Startup to Enterprise 21:33 Building Stakeholder Relationships 23:42 Networking and Career Growth 27:21 Relocating to New York and Its Impact 28:32 User Insights and Product Development 29:49 Launching Ad Glow and Community Building 31:31 Growing Communities from Scratch 32:50 Encouraging Community Engagement 34:36 Balancing Incentives in Community Building 38:19 The Value of Community for Brands 38:41 Moderation and Community Management 40:33 Lightning Round: Quickfire Questions

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

—

Stephen Stouffer is Director of Automation Solutions at Tray.ai, bringing over a decade of experience in markops, revops, and digital transformation. Starting his career as a web developer, Stephen has grown through various marketing technology roles, both in-house and in-agency, and he’s particularly known for his work in marketing automation and AI implementation.

Some takeaways:

1/ 🎯 Keep It Simple

Break down complex systems into their simplest form. Early-career Stephen over-engineered email nurture campaigns; experienced Stephen focuses on fewer, higher-quality touchpoints that are easier to test, manage, and measure.

2/ 🏃 Agency Work = Career Accelerator

Working at an agency is the ultimate career hack. You'll learn multiple tools, industries, and use cases in a compressed timeline. Just remember: burnout is real—set boundaries early and often.

3/ 🤝 Sales-Marketing Alignment Needs Physical Proximity

The best solutions often come from walking across the room. Have marketing join sales stand-ups, move BDRs under marketing's umbrella, and measure marketing by sales-accepted leads (not MQLs) to create true alignment.

4/ 🔧 Tools Don't Fix People Problems

The biggest misconception in digital transformation: thinking new tools will solve organizational issues. If sales imports bad data into Pardot, they'll do the same in Marketo. Focus on people and process first.

5/ 📊 Ditch Open Rates, Focus on Conversions

With Apple's privacy changes and AI skewing email metrics, open rates are increasingly unreliable. Measure success by actual conversions and downstream metrics that tie directly to business goals.

6/ 🌱 Start Small, Scale Smart

For small e-commerce: Start with just HubSpot + BigCommerce. Only add complexity (like Salesforce) when you actually need enterprise-grade features. Don't over-engineer early solutions.

7/ 🎮 Automation = Bridge Building

Success in automation isn't just technical skills—it's understanding both user needs and technical capabilities, then building simple bridges between them that people actually want to use.

8/ 🤖 AI Implementation Strategy

Don't start with code. Ask AI "What are the top 10 ways someone in [your role] at [your company] could use AI?" Then work down that list, starting with what looks most interesting.

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Where to find Stephen Stouffer:

* Web: https://sites.google.com/tray.io/revops-learning-hub/connect

* LinkedIn: https://www.linkedin.com/in/stephenstouffer/

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In this episode, we cover:

00:00 Career Beginnings and Accidental Marketing 03:33 The Puzzle of Marketing Automation 07:36 Simplifying Email Campaigns 11:30 The Role of AI in Development 15:01 Agency vs. In-House Experience 18:48 Navigating Client Relationships and Leadership 24:30 Understanding Digital Transformation Misconceptions 27:24 The Importance of Alignment in Teams 29:16 Integrating Operations and Technology 31:34 Balancing Work and Personal Life 37:33 Maintaining Company Culture During Growth 40:47 Rethinking Email Metrics and Measurement 46:06 Simplifying Marketing Operations for Startups 48:36 Building a Scalable Tech Stack 52:49 Navigating AI in Marketing Automation 55:43 The Dilemma of Automation and Employment 58:54 The Importance of Human Connection in MarTech 01:01:52 Aligning Sales and Marketing for Success 01:04:35 Bridging the Gap Between Sales and Marketing 01:06:30 Leveraging Tray.ai for E-commerce Automation 01:09:57 Lightning Round

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

—

Faisal AlKhalidi is a performance marketing veteran who's helped scale brands like DoorDash, Gainful, and Perfect Keto before founding Growth Minds, where he now helps D2C brands reduce their customer acquisition costs through data-driven creative development.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Mirror, Don't Window: Instead of showcasing your product immediately, reflect your customer's pain points and desires. For example, with joint supplements, lead with grandparents unable to play with grandchildren rather than product features. Only reveal your solution after establishing emotional connection.2/ 🧩 Modular Creative Testing Wins: Break ads into modular components (hook, body, CTA) and test combinations. One winning hook can be mixed with different bodies to create multiple successful variations—work smarter, not harder.3/ 📊 The 1-in-8 Rule: Only about 12% of ad creatives become winners. Plan your creative volume accordingly—for a $50k monthly ad spend, aim for 20+ new creative concepts monthly. Test each for at least 7 days with 5-7x AOV in spend.4/ 🎯 Focus Your Growth Stack: Sub-$10M companies should master three core channels instead of spreading thin: Meta ads, solid website/funnel, and lifecycle marketing (email/SMS). Master these before expanding.5/ 📱 Broad > Narrow Targeting: Platform algorithms have evolved—creative is your new targeting. Focus less on detailed audience settings and more on letting the creative and message attract the right viewers naturally.6/ 🔍 Mine Customer Reviews with AI: Use AI to analyze customer reviews at scale, identifying common pain points, desires, and unique product benefits. This data becomes your creative strategy foundation.7/ 📈 Hook Rate + Hold Rate: Aim for 30%+ hook rate (viewers watching past 3 seconds) and optimize your hold rate (continued engagement). These metrics predict overall ad performance.8/ 💡 Test Smart, Not Hard: Before ruling out an underperforming ad, analyze its components. A weak overall performance might hide a winning hook or other element worth keeping.

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Where to find Faisal AlKhalidi:

* Web: https://www.growthminds.co/

* LinkedIn: https://www.linkedin.com/in/faisalalkhalidi/

* X: https://x.com/faisalalkhalidi

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In this episode, we cover:

00:00 Inbound vs Outbound Marketing Strategies 06:14 Understanding B2B vs B2C Marketing Dynamics 11:13 Retention Strategies for Subscription Products 16:11 Transitioning from Products to Services 21:27 Navigating Multi-Touch Attribution 26:31 Creating Scroll-Stopping Ads 32:10 The Importance of Modular Ad Testing 37:40 Optimizing Ad Performance: Hook and Hold Rates 42:35 Mirroring Customer Needs in Advertising 47:55 Implementing Rapid Testing Cycles 52:11 Evaluating Ad Performance and Spend 57:02 Leveraging Customer Reviews for Insights 01:01:19 Innovative Marketing Practices Today

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

—

Lydia Davey is the co-founder of Attentio PR, where she helps the world's most interesting startups accelerate growth through high-impact earned media coverage. Her journey began as a U.S. Marine Combat Correspondent, built through her time working in Communications at Apple, and most recently continued through fractional Communications leadership roles at various startups.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Story > Stats: It's not just about lining up facts—it's about crafting a narrative that grabs hearts, minds, and wallets. Example: "The queen died, the king died" vs. "The queen died, and the king died of a broken heart." The second version creates emotional investment and curiosity.

2/ 🔍 Media Success = Research + Relationships: Newsrooms have shrunk 20% since pre-pandemic, and journalists now receive 500+ pitches daily. Success comes from deep research into where your story fits and making it dead simple for journalists to say "yes."

3/ ⏰ The "Why Now?" Factor: Even great stories need timing. Whether it's a product launch, market expansion, or cultural moment, successful PR hinges on having a compelling reason for journalists to cover your story today rather than tomorrow.

4/ 🌟 Own It, Apologize, Overcorrect: The three pillars of crisis communications. When things go wrong, leadership needs to take ownership, show genuine remorse (when legally possible), and demonstrate meaningful change.

5/ 📊 ROI Isn't Optional: Top PR pros quantify their impact. It's not enough to say "I ran X campaign"—you need to show the lift in brand awareness, direct traffic, or sales. Track everything and tie it back to business outcomes.

6/ 🎭 Embargoed > Surprise Launches: Give journalists 3 weeks with the story under embargo. This creates a "shock and awe" moment when multiple high-quality stories drop simultaneously, versus trickling out one at a time.

7/ 🤖 AI + Human Judgment: Use AI to iterate quickly and generate ideas, but rely on human judgment for the final narrative. AI can stack facts but struggles to add the emotional context that makes stories compelling.

8/ 🌐 Local Knowledge Matters: For global brands, always hire local PR support. There are cultural nuances and sensitivities that even the best international team can't fully grasp.

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Where to find Lydia Davey:

* Web: https://www.attentiopr.com/

* LinkedIn: https://www.linkedin.com/in/lydiadavey/

* X: https://x.com/lm_davey

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In this episode, we cover:

00:00 From Marine to Media: Lydia's Journey 03:10 The Art and Science of Storytelling in PR 05:58 Building a PR Agency: Lessons from the Ground Up 08:41 Crafting Compelling Narratives: The Heart of PR 11:23 Finding the Right Story: Case Studies in PR Success 13:48 Navigating Crisis Communications: Strategies for Success 16:19 Measuring ROI in PR: Beyond the Headlines 18:54 The Role of Creativity in PR Campaigns 21:22 Understanding Negative PR: Lessons Learned 22:56 The Importance of Leadership Buy-In in PR 37:51 Navigating Media Opportunities 43:52 The Importance of Media Training 46:37 Starting PR on a Budget 50:01 In-House vs Agency PR 52:37 Hiring for PR Success 57:35 Finding the Right Agency 01:02:33 The Appeal of Agency Work 01:04:05 Managing Competing Priorities 01:06:31 Lightning Round Insights

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

—

Tosin Thomas is Head of Marketing at Financial Cents, where she transformed virtual events into a growth engine by bringing scientific rigor from her biochemistry background to B2B marketing.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Test Small, Scale SmartSuccessful marketing isn't about doing everything—it's about testing channels cheaply, measuring results rigorously, and doubling down on what works. Case in point: Their first brand conference cost under $10k as a test, then scaled after proving ROI.2/ 📊 Self-Reported Attribution > Assumptions Ask customers directly how they found you. When you consistently hear the same channel (like LinkedIn), that's your signal to invest more heavily. Combine this with traditional tracking for a complete picture.3/ 🎬 Virtual Events Need Unique Value PropsDon't compete with established in-person conferences. Instead, create something different—like multi-track sessions tailored to different company sizes or interactive "workflow roasts" that solve real problems live.4/ 🔄 Content Redistribution > CreationSocial media shouldn't be a channel for new content—it should redistribute existing content in new formats. Turn blog posts into carousels, event clips into short videos, and customer stories into memes.5/ 💪 Hire for Marketing Skills First, Industry Knowledge SecondWhen building a marketing team, prioritize hiring excellent marketers who can learn your industry rather than industry experts who know some marketing. The learning curve is steeper for marketing skills than industry knowledge.6/ 🎁 FOMO > Convenience Drive event attendance by emphasizing what attendees will miss—exclusive resources, live networking, speaker templates—rather than just promoting the recording access. Their events hit 40-60% attendance vs. industry standard 30%.7/ 🎨 Brand Building Makes Performance CheaperStrong brand presence reduces customer acquisition costs across all channels. When people recognize your brand from content or events, they're more likely to engage with ads and convert.8/ 🤝 Strategic Partnerships Amplify ReachPartner with complementary tools and communities to expand reach. Example: When featuring a customer using multiple tools, involve all those companies in promotion for exponential reach.9/ 📈 Focus Marketing Roles on Scale-Ready ChannelsOnly create dedicated roles for channels showing clear traction and ready for scaling. Each new hire should own a channel that's proven its worth but needs focused attention to grow.

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Where to find Tosin Thomas:

* Web: https://mainstack.me/tosinthomas

* LinkedIn: https://www.linkedin.com/in/tosinthomas/

* X: https://x.com/TosyneThomas

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In this episode, we cover:

00:00 Introduction and Background 00:41 Transitioning from Biochemistry to Marketing 06:49 Understanding MQLs and SQLs 12:25 Balancing Brand and Performance Marketing 18:01 Innovative Event Strategies 23:32 Engagement and Attendance Strategies 29:06 Event Strategy and Education Focus 31:05 Pinpoint Webinars and Demo Days 32:26 Quarterly Branded Events and Educational Focus 33:22 Innovative Event Formats and Community Engagement 34:57 Strategies for Event Attendance and Registration 37:50 Using Events for Customer Retention 39:15 The Power of Content Marketing 42:00 Building a Marketing Strategy 44:22 Choosing the Right Social Media Platforms 48:09 Marketing Attribution and Tracking 51:07 Content Creation for Social Media 56:04 Building a Marketing Team 01:02:35 Hiring for Skills vs. Industry Experience 01:04:45 Onboarding New Team Members 01:06:52 Fostering Team Culture 01:11:02 Lightning Round: Quickfire Questions

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

—

Pete Sena is a serial entrepreneur and creative strategist behind companies like Digital Surgeons - a consultancy he started in 2004, The Resonance - where he partners with leading experts to create new revenue streams, and District - a tech innovation campus in New Haven, Connecticut. He’s known today for being an AI expert helping people to build, grow, and scale companies using AI, creativity, branding, and storytelling.

Some takeaways:

1/ 🧠 Curiosity Beats CompetenceThe competitive advantage in the post-AI era will be creativity and curiosity, not just technical skills. Better questions create better outcomes. Start by asking "why" and going five levels deep to uncover core motivations and insights.2/ 🎯 Distribution + Creativity = SuccessThe next 20 years will be driven by two key factors: your ability to get people to care about what you think (distribution) and creativity. Master these and you can succeed regardless of age or background.3/ 🤖 AI = Junior EmployeeTreat AI like a junior team member - capable but needs clear direction and oversight. It excels at specific tasks but lacks wisdom and experience. Focus on giving clear instructions and iterative feedback to improve outputs.4/ 🔄 Chain Before AgentStart with simple chain-of-thought prompting before jumping into complex AI agents. String together simple prompts (input → output → new input) to create powerful workflows. Tools like Zapier make this accessible to non-technical users.5/ 🎨 Design Your Culture (Or It Designs You)Culture is like yogurt - you need the right starter culture. Intentionally design your organization's behaviors, rituals, and incentives. Clear expectations and consistent reinforcement shape stronger cultures than top-down mandates.6/ 🌱 Show Up + Do The Work90% of success is consistently showing up prepared. Under-promise and over-deliver. Build trust through reliability before seeking scale.7/ 💡 Unlearning > LearningFuture success requires unlearning old patterns and limiting beliefs. Stay adaptable and question "that's how we've always done it" thinking.8/ 🤝 Soft Skills Are The Hard SkillsEmotional intelligence and human connection matter more than technical expertise. Even in an AI world, people want to interface with people.

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Where to find Pete Sena:

* LinkedIn: https://www.linkedin.com/in/petersena/

* X: https://x.com/petesena

* Web: https://petesena.com/subscribe

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In this episode, we cover:

00:00 Introduction and Setup 00:34 The Journey of Entrepreneurship 07:24 The Evolution of Learning and Technology 09:44 Curiosity and Creativity in the AI Era 12:19 Understanding the Depth of 'Why' in Conversations 15:34 The Power of Distribution in the Digital Age 20:08 Scaling Success: The Importance of Consistency 22:40 Leveraging AI for Enhanced Marketing Efficiency 28:33 Driving Change: The Art of Transformation 32:40 Creating Conditions for Intrinsic Motivation 38:07 Getting Started with AI: Overcoming Fear and Hesitation 41:59 Common Mistakes in AI Application for Marketing 45:26 Getting Started with Agents and Automation 48:51 The Role of AI as Junior Employees 51:12 Data and Distribution: Keys to Success 53:05 Unlearning for Growth 55:46 Leadership and Operationalizing Ideas 59:03 Navigating the Challenges of Today's Youth 01:02:26 Optimizing Time with the Green Zone 01:09:15 Design-Driven Culture: Building the Right Environment

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

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Joe Wilkinson helped scale Lucid past $100M ARR and now advises early-stage startups on product-led growth and turning visitors into customers through his boutique consultancy Artisan Strategies.

Here’s some of my takeaways from this week’s episode…

1/ 🎯 Value First, Distribution Second• The best products create an amazing core experience that sells itself• Distribution becomes about showcasing that incredible experience• Start with making something people genuinely love, then figure out how to reach them2/ 🔄 Monthly > Annual Early On• Monthly subscriptions force everyone to focus on customer retention• Teams naturally optimize for keeping users happy and engaged• Build better products by allowing customers to "vote with their feet"3/ 📊 Data Should Serve Action, Not Vice Versa• Data alone never makes decisions - humans do• Avoid using data as an excuse for inaction• Better to ship without perfect data than to have perfect data and never ship4/ 🎨 Not All Clicks Are Equal• Remove friction that blocks value, not just any friction• Video games have long onboarding but users don't mind because it's valuable• Focus on maintaining momentum toward the core value proposition5/ 💼 The Power of Fractional Leadership• Get higher-caliber talent than you could afford full-time• Perfect for early-stage companies that need expertise but not full-time roles• Can be more impactful in 1 day/week than a full-time junior hire6/ 🎯 Operational Risk > Opportunity Risk• Focus on executable strategies with clear value vs speculative bets• Example: Master proven channels (SEO) vs chasing new unproven ones• Success comes from execution quality, not gambling on opportunities7/ 🌱 Solve The Now, Build For Later• Must survive today to thrive tomorrow• Make decisions that work now but inform future vision• Balance immediate revenue needs with long-term product development8/ 🎮 Product-Led Growth Requires Consumer-Grade Experience• Enterprise software needs to feel as good as consumer apps• Focus on individual user delight first• Let grassroots adoption drive enterprise sales

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Where to find Joe Wilkinson:

* LinkedIn: https://www.linkedin.com/in/josephwilkinson/

* Web: https://artisangrowthstrategies.com/

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In this episode, we cover:

00:00 Global Connections: The Power of the Internet 00:25 The Evolution of Podcasting and AI 01:55 Insights from Venture Capital: Learning from the Best 06:35 Growth Strategies: Lessons from Lucid 11:19 The Journey of Lucid: From Startup to Success 13:11 Lucid's Core Offerings and Innovations 13:58 Mindset for Growth and Experimentation 16:10 The Importance of Testing and Learning 17:07 A/B Testing Success Rates and Strategies 19:47 Achieving Statistical Significance in Testing 23:44 Frequentist vs Bayesian Approaches to Testing 30:03 Understanding Click Value in User Onboarding 34:17 The Concept of Product-Led Growth 36:02 Grassroots vs Traditional Sales Models 40:09 Common Misconceptions about Product-Led Growth 41:34 The Role of Data in Business Decisions 42:30 The Role of Data in Decision Making 47:21 Understanding Time Horizons in Business 50:24 Navigating the Middling Problem 57:11 The Rise of Fractional Work 01:03:51 Operational Risk vs Opportunity Risk

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.

Listen now on YouTube, Spotify, and Apple.

—

From studying mechanical engineering to leading Product at startups that have raised a combined $500 million, Kari Ostevik has deep experience shipping successful products in high-stakes environments. And from her time leading growth after a CMO left, Kari has a unique perspective on the Product/Marketing relationship.

Some takeaways:

1. 📢 Push Past the Squeaky Wheel Trap: In many orgs, decisions often default to "whoever shouts loudest." Combat this by bringing hard data + user interviews to the table.

Pro tip: Build a compelling narrative around why certain features deserve priority over what your noisiest stakeholder might want.

2. ⏱️ Meeting Hack Alert: Nobody reads pre-reads (shocking, we know). Instead of sending docs ahead, block dedicated "heads down" time during meetings.

Kari's move? Put on lo-fi beats and give everyone 5-10 mins to process + comment. Way more effective than hoping people did the homework.

3. 🧠 The "Crazy Eights" Brainstorming Tech: Need fresh product ideas? Fold paper into 8 squares, give everyone 8 minutes (1 min per square) to sketch solutions.

The magic? People work independently first = less groupthink, more innovation.

Bonus: Works for remote teams via Miro.

4. 🎯 Stop Being Data-Obsessed (Or At Least Pick The Right Metrics): While metrics matter, Kari warns against getting too tunnel-visioned on short-term data wins.

Hot take: Sometimes chasing metrics can actually wreck your user experience. Balance quantitative insights with maintaining product vision.Like we saw earlier with Sundar, consider defining better metrics that are more aligned with your long-term vision.

5. 👑 The Authority Paradox: PMs lead without direct authority (awkward). Kari's solution? Early 1:1s with team members to understand their past PM experiences + explicitly position yourself as their "umbrella" – there to help them do their best work.

6. 🎥 The Gong-Guerrilla Testing Matrix: Use this to identify what really matters to your decision making users (aka, ideal customer profile / ICP).

* B2B Move: Mine Gong (sales call recording) data for deep user insights

* B2C Move: Hit the streets for rapid guerrilla testing with random folks

Key difference? B2B requires more finesse (sales team gets nervous about customer access), while B2C lets you move fast and break things.

7. 📐 The "Two-by-Two" Priority Framework: Skip complex prioritization matrices. Plot features on two axes: ease vs. value. The real gold? It forces explicit conversations about why something ranks higher/lower than other options.

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Where to find Kari Ostevik:

* LinkedIn: https://www.linkedin.com/in/kariostevik/

* X: https://x.com/kariostevik

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In this episode, we cover:

00:00 Welcome 01:05 Transitioning Through Major Company Changes 02:40 Insights from B2B vs B2C Product Management 06:03 Prioritization Techniques in Product Development 09:36 Effective Cross-Functional Collaboration 11:34 Innovative Workshop Techniques for Product Teams 14:13 Collaborative Ideation Techniques 15:06 The Importance of Data in Product Management 15:21 Balancing Data-Driven Decisions with User Experience 16:58 Staying Connected to Industry Best Practices 20:49 Managing Teams and Building Relationships 21:19 Lessons from Teaching and Leadership 24:19 Advice for Aspiring Product Managers 24:33 Lightning Round Insights

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Obligatory disclaimer: I've worked at YouTube and Google for about a decade in various marketing teams. Nothing I say in my personal spaces is necessarily endorsed by them.