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 timing, valuation, and life after the exit. ⚡ What You'll Learn: Why most earnouts never get paid — and how to protect yourself. The hidden risks behind LOIs, retrades, and exclusivity windows. How a dev-shop equity arrangement fueled 20 years of bootstrapped growth… until it didn’t. How interest rate spikes in 2022 instantly destroyed a great LOI. Why Eric ran three processes before landing the final buyer. How to evaluate PE buyers and spot red flags during diligence. Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode100&utm_id=%24100M++Exits Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode100&utm_id=%24100M++Exits 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 an accomplished startup CEO with over two decades of experience leading and scaling SaaS companies. As the founder and CEO of eSkill Corporation, he built the company from concept to successful exit—achieving 20 consecutive years of revenue growth without outside funding. Under his leadership, eSkill became a leader in the HR technology space, serving global clients such as PepsiCo, GE, Deloitte, Stanford University, Zappos, the United Nations, and the U.S. State Department. He brings deep expertise in lean operations, sustainable growth strategy, and product-market adaptation. His ability to lead through both stable and volatile market conditions has made him a trusted operator in the SaaS space. His approach blends strategic discipline with operational agility—adapting go-to-market models and product fit in response to shifting customer and market needs. You can reach out to Eric through: LinkedIn: https://www.linkedin.com/in/eric-friedman-604258/ ABOUT JASON KIRBY Jason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+ You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT $100M EXITS My goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
