Eric Friedman spent 20 years bootstrapping eSkill into one of the largest skills-testing platforms online. He ran three full exit processes, navigating retrades, ghosted buyers, rising interest rates, and mounting debt pressure from a dev-shop equity structure that suddenly changed ownership. His final sale to private equity included an earnout, and what he learned is something every founder needs to hear: earnouts rarely pay, and once you hand over control, you lose the ability to hit those targets.
In this episode, Eric breaks down how he evaluated LOIs, why he prioritized buyers who actually understood the business, and the red flags founders ignore when they're desperate to close. If you're thinking about selling your company, or even raising capital, this is a playbook on what to do, what to avoid, and what Eric would do differently.
👉 Watch now: YouTube link
Here’s what you’re in for:
00:00 Introduction
03:40 Choosing an Investment Bank
06:22 Running the Sale Process
15:42 Finalizing the Deal and Advice for Founders
19:59 Evaluating Potential Bosses and Partners
20:25 The Importance of Thorough Due Diligence
21:34 Transparency in Negotiations
23:22 Understanding and Negotiating Earnouts
24:47 Post-Acquisition Transition
35:39 Life After the Exit
37:21 Final Advice for Founders
ABOUT Eric Friedman
Eric Friedman is the founder of eSkill, a global leader in online skills testing trusted by thousands of employers. After bootstrapping the company for more than 20 years, Eric navigated multiple macro cycles, a complex dev-shop equity structure, and three full M&A processes before selling to private equity in 2024.
His experience spans product development, SaaS scaling, hiring, and exit strategy, with a unique behind-the-scenes look at earnouts, LOIs, and the realities of buyer behavior.
Get in touch with Eric:
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📝 - Playbook for Negotiating Term Sheets - Download it Here
💽 - Playbook for Setting Up and Sharing Your Data Room - Download it Here
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📞 - Guide to Nailing Your First Calls With Investors - Download it Here
📆 - Your 12-month Fundraising Plan- Download it Here
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