50 - Billion Dollar Lessons from a $800M Mistake with Elizabeth Knopf

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Join me, Nik (https://x.com/CoFoundersNik), as I talk with Elizabeth Knopf ( https://x.com/leveragedupside ), a venture capitalist turned operator who has scaled startups in Latin America, worked on billion-dollar unicorns, and is now hunting for cash-flowing software businesses.

In this episode, Elizabeth shares lessons from passing on companies like Shopify, key metrics for evaluating SaaS companies, and how she leverages AI to transform small businesses. We also dive into spotting the next billion-dollar idea and avoiding the 'what if' game with investments. 

Questions this Episode Answers:

• What lessons did Elizabeth learn from passing on companies like Shopify?
• How does Elizabeth evaluate SaaS companies?
• How is AI transforming small businesses?
• How do you know when you've found the next billion-dollar idea?

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This week we covered:

00:19 The What If Game: Hypothetical Investment Scenarios

01:33 Guest Introduction: Elizabeth Knopf's Background

03:06 Elizabeth's Investment Journey: From Hedge Funds to Venture Capital

04:20 Deep Dive into Venture Capital: Sourcing Deals and Missed Opportunities

13:40 Evaluating SaaS Companies: Key Metrics and Lessons Learned

18:46 Elizabeth's Transition to Operations and Entrepreneurship

23:55 Leaving Axon and New Ventures

25:35 The M&A Journey Begins

27:22 Investment Strategies and Challenges

36:11 AI and Automation in Business

42:50 Rapid Fire Questions and Wrap-Up