Tim Guleri - Legendary VC & Tech Founder with Multiple IPO Exits | Building Billion-Dollar Tech Companies

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Tim Guleri is a seasoned venture capitalist and managing partner at Sierra Ventures, a Silicon Valley-based early-stage technology-focused venture capital firm. With over two decades of experience in the technology industry, he has a strong track record of identifying and nurturing successful startups. Before joining Sierra Ventures, he co-founded Scopus Technology, which went public in 1995 and was later acquired by Siebel Systems for $460 million, and Octane Software, which was acquired by E.piphany in 2000 for $3.2 billion. 

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➡️ Talking Points

00:00 - Intro

05:23 - The Common Thread in Tim’s Journey

08:01 - Born Entrepreneur or Learned Skill?

10:31 - How Entrepreneurs Find Their Focus

18:30 - Tim’s Career & Investment Philosophy

22:08 - Sponsor Break

24:46 - The Evolution of Sierra Ventures

30:27 - Founder Traps in Venture Capital

35:08 - Managing Risk at Sierra Ventures

40:57 - Finding Investors: Tips for Founders

49:50 - Sponsor Break

52:03 - The Biggest Challenge for First-Time Entrepreneurs

57:24 - Riding Trends vs. True Innovation

1:00:26 - Is There an Undiscovered Playbook for Distribution?

1:03:17 - Scaling Without Crashing

1:08:05 - Making High-Stakes Decisions with Confidence

1:12:28 - Smart Exit Strategies for Entrepreneurs

1:17:03 - Final Thoughts from Tim Guleri

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