The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless

45 snips
May 15, 2024
Dan Siroker, Co-founder and CEO of Limitless, shares his insights from his experience scaling Optimizely and securing a massive Series A valuation. He emphasizes that serial entrepreneurs are often more successful, highlighting their advantages in focus and team dynamics. Fundraising tactics are dissected, including how to create urgency and respond strategically to investor inquiries. Siroker also discusses the importance of understanding equity, navigating the AI investment landscape, and balancing parenthood with entrepreneurial ambitions.
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ADVICE

Serial Entrepreneur Advantage

  • Prioritize backing serial entrepreneurs over first-time founders.
  • Serial founders possess valuable experience, better networks, and increased perseverance.
ANECDOTE

Benchmark's Flexible Investment

  • Dan Siroker got Benchmark to invest in Optimizely's Series A for under their typical minimum ownership.
  • This was possible because the company was performing well, allowing Siroker to negotiate effectively.
ADVICE

Negotiation Tips

  • Be willing to compromise on valuation during fundraising negotiations.
  • Empathize with investors and give them wins to build a positive long-term relationship.
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