Built to Sell Radio Ep 513 Exit Story: How Dave Sifry Lost $100 Million, Lessons from Starting 9 Companies, the Dangers of Raising Money, and Why He’s Doing It Differently with Warmstart
Sep 26, 2025
Dave Sifry, a nine-time founder known for Technorati and LinuxCare, shares his entrepreneurial journey and valuable lessons learned. He reflects on the regret of passing up a $100 million exit, the pressures of venture capital, and the risks of growth-driven strategies. Sifry emphasizes the importance of maintaining control and integrity while building companies. His latest venture, Warmstart, focuses on leveraging past contacts for new business opportunities, showcasing how innovative thinking can change the fundraising landscape.
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Web As Live Conversation
- Technorati indexed the "live web" and treated the internet as a set of conversations rather than a static library.
- Indexing content within 60 seconds enabled real-time tracking of blog conversations and influence.
Understand Investor Return Expectations
- Expect investors to reset exit expectations to much higher multiples than founders imagine.
- Plan strategy around those expectations before you accept venture capital to avoid misaligned goals.
Growth Mindset Versus Profitability
- Venture-backed thinking prioritizes growth over immediate profitability and often tolerates deliberate losses.
- That mindset changes hiring, spend, and product decisions compared with bootstrapped businesses.