20VC: THE PINTEREST MEMO: BESSEMER’S JEREMY LEVINE ON THE SECRET TO SUCCESS WITHIN USER GENERATED CONTENT PLAYS, WHERE MOST INVESTORS MAKE MISTAKES WHEN ANALYSING CONSUMER SOCIAL AND HOW THE PINTEREST DEAL WOULDN’T HAVE HAPPENED WITHOUT A DIVERSE PARTNERSHIP

Jeremy Levine is a Partner @ Bessemer Venture Partners, one of the leading venture firms of the last two decades. Their portfolio includes the likes of Pinterest, Shopify, LinkedIn, Yelp, Twilio and many more. As for Jeremy, five of his early-stage investments—LinkedIn, MindBody, Pinterest, Shopify and Yelp—grew into billion-dollar publicly traded companies. He has featured on the Forbes Midas List for several years running.

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In Today’s Episode with Jeremy Levine on Pinterest You Will Learn:

1.) How Jeremy came to make one great decision and make one big mistake all in one rainy afternoon in Palo Alto? What was the story behind meeting the Pinterest team for the first time? Who was there? How did it go down?

2.) Market

How did Jeremy analyse the market at the time of the investment? What are the core lessons Jeremy learned about making successful user-generated content plays? Where was Jeremy wrong in how he analysed the market? In what way is Jeremy surprised with how the market evolved? How does Jeremy analyse market timing today?

3.) Team

Jeremy has previously called Ben Silberman a “product visionary”, what made Jeremy say this about Ben? How did Jeremy get over the concern of many VCs that Pinterest did not have a technical co-founder? Having seen Ben change over the last decade, what have been the biggest changes in Ben’s leadership style over the last 10 years?

4.) Traction

When evaluating traction, where does Jeremy think so many investors make mistakes today? How should founders determine what is their core North Star metric? What gave Jeremy the confidence Pinterest could “cross the chasm”? How did the early Pinterest cohorts look both from usage and retention? What elements surprised and impressed him?

5.) Pre and Post Mortem

What did Jeremy see as the likely reasons Pinterest would not work? How did Jeremy think through what it took for UGC platforms to monetise at the time? Where was he wrong here? What did Jeremy see as the upside? What did he believe Pinterest could be if all the stars aligned?

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