Why 70-90% of Founders Regret Their Exit, and How to Avoid It

Tenacity with Sonia C is a podcast for founders building real companies. Each episode explores how founders decide what to build, how they prioritize, and how they navigate uncertainty as they move from idea to product and from product to growth.Most founders obsess over building the product, but not when they exit, and that’s where they lose leverage, leave money on the table, and sometimes watch their company’s culture get dismantled after the deal.In this episode of Tenacity with Sonia C., Sonia sits down with Kevon Saber (multi-exit founder and the mind behind Legacy Outcomes) to unpack the uncomfortable truth: the M&A system favours repeat buyers, not first-time sellers. Kevon shares what he learned after multiple exits, why smart founders still get outmaneuvered, how to prepare your company years before a sale, and how to protect your people and mission when private equity or a strategic buyer comes knocking.You’ll learn:Why founders often get “intoxicated” by the idea of an exit, and how it costs themThe difference between selling and achieving a peak outcome (right buyer, right price, right terms)What buyers actually value (hint: it’s not always the flashy partnerships)The 3 pillars to build with exit in mind: team, systems/documentation, and unit economicsHow to improve metrics before going to market, and why a good advisor may tell you to wait 6–12 monthsHow to reduce regret by defining your seller objectives before emotions take overHow founders can put commitments in writing (employees, pricing, community/charity) and why buyer character matters even moreA real founder lesson: you can change skills, but you can’t change character, and why co-founder alignment is everythingWhat “spark” interest from a big company really means, and what a realistic timeline to close actually looks likeIf you’re bootstrapping, pre-revenue, scaling fast, or simply building something you care deeply about, this conversation is your reminder: exit strategy isn’t a last-minute event, it’s a leadership decision.If you enjoyed this conversation, follow Tenacity with Sonia C for more honest discussions with founders who share the realities of entrepreneurship, leadership, growth, and resilience, without the highlight reel.Follow Our Socials:Website: https://soniacouto.com/podcast YouTube: https://www.youtube.com/@TenacitywithSoniaCHost IG: https://www.instagram.com/soniactechAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy