20VC: Why Market Always Wins Over the Founder & Why I Do Not Do Market Sizing | Why it is not the Best Time to be Investing but it is the Best Time to Have a Fund & The Type of Deals to do Today | Why The Best Founders Have 100 Year Plans with Wes Chan, C

Wes Chan is the Co-Founder and Managing Partner at FPV Ventures, a $450M early-stage fund, launched earlier this year. Wes is an investor in five $10B+ "decacorns," his most notable being Canva where he is a member of the board of directors and led the Series A and C rounds. Wes also wrote the first or very early check into Plaid, Flexport, Gusto, Lucid, and RobinHood. Before FPV Wes was a Managing Director at Felicis Ventures and before Felicis Wes founded GV's seed investing program. If that was not enough, as an operator, Wes co-founded Google Analytics and Google Voice and holds 18 US patents for his work in creating Google AdWords.

1.) From Founding Google Analytics to Venture:

• How did Wes make his way from founding Google Voice and Google Analytics to starting GV's seed investing program?
• What are 1-2 of the single biggest product takeaways from working closely with Larry and Sergey @ Google?
• How did Wes make his way from Google to Felicis and scaling the firm with Aydin Senkut?

2.) Market vs Founder: Why Market Sizing is BS:

• Why does Wes believe that the market always wins over the founder?
• That said, what does Wes mean when he says "the best founders have 100 year plans?"
• How does Wes question and analyse 100 year plans? What makes the best? What makes the worst?
• Why does Wes not do market sizing? Why does Wes not do outcome scenario planning?
• What does Wes believe is the biggest fallacy of outcome scenario planning?

3.) The Venture Landscape:

• Does Wes believe that now is really the best time to be investing?
• Why does Wes believe there are some treacherous deals being done now? What are the signs that these deals are challenging?
• What advice does Wes give founders fundraising in these markets?
• What does Wes believe are elements that traditional VCs decide to do, which prevents founders from choosing to work with them?
• Does Wes believe VCs on board truly provide value? If so, which ones and why them?

4.) FPV: Firm Building and Portfolio Construction:

• With the new $450M fund, what is the portfolio construction that Wes chose?
• Why does Wes prefer to have more lines in the portfolio than a concentrated portfolio?
• Does Wes believe you can increase your ownership in your best companies over time?
• How does Wes think about capital concentration on a per company basis?
• What have been Wes' biggest lessons from his biggest hits and misses?

Wes' Favourite Book: Liar's Poker