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EP 100: The Earnout Trap: What This Founder Learned After Selling His Company

After 20 years of steady, bootstrapped growth, Eric Friedman sold his company, eSkill, an online skills testing platform used by employers worldwide.

In this episode, Eric breaks down how he built a profitable SaaS business with no outside funding, ran three separate sales processes, and closed a deal with private equity in 2024. He shares what founders should know about earnouts, how to choose the right investment bank, and the red flags he learned to spot during M&A negotiations.

If you’re a founder thinking about selling a bootstrapped company, this episode is packed with real lessons on…

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