Maximizing Value in the Middle Market: M&A Lessons from Alan Scharfstein

On this episode of Open for Business, Stuart and Norman welcome Alan Scharfstein, Founder and CEO of The DAK Group, one of the nation’s most trusted advisors to middle-market business owners navigating high-stakes M&A decisions. With more than 750 transactions completed across industries and borders, Alan shares what founders most need to know before they sell: why an unsolicited offer isn’t the same as a true market process, how the right advisor can locate buyers you’d never expect, and why buyers don’t “buy your past” — they buy a company’s future story and the roadmap to growth. You’ll also hear Alan’s candid take on: When it makes sense to not sell — and how the best bankers talk owners off the ledgeWhat sellers obsess over that doesn’t matter to buyers (and what buyers care about most)The most common ways founders unintentionally leave money on the tableWhy “due diligence” can feel like a “colonoscopy without anesthesia,” and how to manage it without losing momentum in the businessHow to evaluate value beyond price: employees, legacy, life-after-sale, and the emotional reality of closing dayRed flags in buyers, deal “retrades,” and how to protect yourself from terms that shift risk back onto the sellerA lightning round of hard-won lessons on handshakes, negotiation mistakes, and what owners should never say at the tableAlan also weighs in on what’s ahead for the deal market — private equity dry powder, increased international interest in U.S. businesses, and why strategic acquirers continue to rely on M&A for growth — plus how AI is reshaping diligence and deal execution without replacing the human judgment that closes great transactions. Whether you may be years from an exit or are getting approached right now, this conversation is a practical masterclass in preparing, positioning, and protecting what you’ve built — so you can maximize value and walk away feeling great about the outcome.Love the show? Subscribe, rate, review, & share! https://www.stevenslee.com/