Dave Sifry on avoiding the $100 million mistake
“Dave Sifry founded nine companies raising more than $170M along the way. In this episode he talks about benefiting from the advice provided by his investors, reading an earn-out and judging how much your money is truly at risk,” shares Sam Thompson, a Minneapolis business broker and the president of M&A firm Transitions In Business. “He also mentions how to avoid the ego trap that leads business owners to pass on life-changing offers.”
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.
In this conversation, you discover how to:
- Decode how a new round quietly resets your exit bar to 5–10x the post-money.
- Recognize veto rights and preferences that can block a sale you want.
- Weigh majority control versus dilution when the board takes over.
- Avoid the ego trap that leads owners to pass on life-changing offers.
- Read an earn-out and judge how much of your price is truly at risk.
- Build the “business physics” of your company before hiring ahead of revenue.
- Use investor relations strategically to create leverage, not distractions.
Listen now to hear Dave Sifry’s hard-earned lessons on the real cost of waiting too long to sell.