With a few dozen software exits under his belt (including Box, Square, Mulesoft & JFrog), nobody knows enterprise investing like Sapphire Ventures’ President + PartnerJai Das. Likewise, Floodgate co-founder + Partner Mike Maples Jr. is often credited with pioneering seed investing as we know it, with names like Twitter, Twitch and Lyft in his portfolio. Together, they join Nick Chirls, GP at Asylum Ventures,  and Beezer Clarkson, LP at Sapphire Partners, to share how they pick winners at their respective stages. What does it take to spot someone who sees the future before it’s here? How do inflection points like AI impact an investor’s thesis? And are there more opportunities in the market for VCs today? Plus, Jai and Mike discuss the one throughline from seed to growth to lead to a successful exit: the management team.

Learn more about Sapphire Partners: sapphireventures.com/sapphire-partners

Learn more about OpenLP: openlp.vc

Learn more about Asylum Ventures: asylum.vc

Learn more about Sapphire Ventures: sapphireventures.com

Learn more about Floodgate: floodgate.com

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CHAPTERS:

0:00-Introduction & the Burning Question4:08-Intro to Sapphire Ventures

6:02-Intro to Floodgate7:56-Setting the Stage at Seed

10:30-Inflection Points: We're Going Through a Sea Change of Mass Cognition

13:43-What’s Happening at the Growth Stage

15:17-More Choice in the Market

16:10-Importance of Management Team

17:44-Mike’s New Book “Pattern Breakers”

23:09-The Three Things Floodgate Looks for in a Founder

25:25-Founder Future Fit & Pivots

27:56-In Enterprise Software, You Don’t Always Have to Build a New Category29:52-AI: Over-Valued? Under-Valued?

32:50-Is There Anything Left in AI Non-Consensus?

34:37-How Sapphire Approaches GenAI Investing

37:31-The Exit Market Today

44:10-How to Approach Founder Liquidity