20VC: Lessons from Investing $2BN and Returning $8BN in Cash | Why Most Venture Partnerships are Broken | We Sold Salesforce Early and Lost Out on Billions | Are The Best Deals Always Expensive and Competitive with Jake Saper @ Emergence Capital

Jake Saper is a General Partner @ Emergence Capital, one of the leading venture firms of the last 20 years. Their many wins include being early investors in Salesforce, Zoom, Veeva and more. In total, the firm has invested $2BN and returned an astonishing $8BN in cash with much more to come. 

In Today’s Episode We Discuss:

04:45 The Zoom Investment Story

10:21 Founder, Market, Traction: Rank Them

26:37 Why Market Pull is the Most Important Thing and How to Know

27:23 Are the Best Deals Always Expensive?

28:25 What is the One Framework Emergence Use for Every Investment

29:08 Lessons from the 16x DPI Zoom Fund

30:44 Why Does Every Partner Do Reference Calls on Every Deal?

35:16 We Have Lied to SaaS Founders: The Revenue Rules Changed

37:53 Where Will Value Accrue in a World of AI? 

41:37 Three Reasons Why AI Will Not Replace Vertical SaaS

46:38 Who Wins in AI: Startups or Incumbents?

50:09 Why Should Every Company Aim to Be a “Board Discussion”

55:12 Why is Jake Worried About AI’s FTX Moment?

56:00 What Losing Billions on Salesforce Taught Us About Selling

01:00:07 Why Most VC Partnerships are Broken

01:03:07 Grok vs Anthropic vs OpenAI: Buy and Sell?

01:14:25 Quickfire Round: Insights and Reflections