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

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

Author: John Warrillow September 26, 2025 Duration: 58:43

Dave Sifry has founded nine companies, including Technorati and Linuxcare, raising more than $170 million along the way. In this episode of Built to Sell Radio, he reveals how he went from being worth more than $100 million on paper to watching that value disappear — and what he'd do differently if he had the chance again. 

Despite those scars, Sifry has built an extraordinary career. He has founded nine companies and today is founder and CEO of Warmstart, a platform that helps entrepreneurs turn old contacts into new business. 


For any entrepreneur, the idea of selling the company they've built is both a daunting prospect and a potential pinnacle of success. Built to Sell Radio, hosted by John Warrillow, steps into that complex space with a clear, practical focus. This isn't about abstract theory; it's a weekly conversation grounded in real experience. Every episode features a different founder who has recently navigated the sale of their business. The discussion goes straight to the heart of the matter: understanding the personal and strategic reasons behind the decision to sell. Listeners get an honest breakdown of what worked, from preparation and valuation to negotiation, and perhaps more importantly, the unforeseen pitfalls and mistakes made along the way. It’s that candid post-mortem, the lessons learned in the trenches of a transaction, that provides unparalleled value. By compiling these firsthand accounts, the podcast builds a comprehensive library of exit strategies and cautionary tales. Tuning in feels like gaining access to a private mastermind, where seasoned entrepreneurs share the unvarnished truth about cashing in their life's work. If you're contemplating your own eventual exit, this series offers the nuanced, peer-to-peer insights you need to think like a buyer, protect your interests, and ultimately, build a business that is truly desirable. Built to Sell Radio serves as an essential guide, transforming the opaque process of selling a business into a clearer, more manageable journey.
Author: Language: English Episodes: 100

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