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, Co-Founder @ FPV Ventures

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.

In Today’s Episode with Wes Chan

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?

Items Mentioned in Todays Episode:

Wes’ Favourite Book: Liar’s Poker