#6 | Charlie Calise: Private Equity Overpaid and the Math Fails

Charlie Calise thinks private equity overpaid across the last cycle, and the companies underneath those deals may never make the math work.More on Charlie Calise and this episode: thedealtablepodcast.com/episodes/charlie-caliseHe is blunt about what cheap money did to deal math, and about a consequence buyers rarely price in: overpaying does not just produce a bad return, it breeds toxicity inside the operating company. He walks through what actually makes an acquisition accretive, and tells the story of a client that bought a company for its store-door delivery model without ever checking whether there was room left on the truck.Calise is the CEO of Calise Partners and chairman of Imaginuity, which he acquired in order to own the full customer journey rather than build the capability internally. He has done multiple acquisitions and runs a family office, so the conversation moves easily between buying capability, integrating culture, and what happens to a family's money afterward.Also covered: owner dependency and the exit-planning trap, family operating agreements and generational wealth, the cost of a bad hire and how hiring standards changed after COVID, and where AI is genuinely changing agency economics rather than just headcount.Charlie Calise is the CEO of Calise Partners and the chairman of Imaginuity, a Dallas marketing and technology firm he acquired. He is a veteran marketing strategist who has run multiple acquisitions and oversees a business handling millions of transactions a year, alongside a family office.KEY MOMENTS00:00 Why the multiples do not survive07:05 Data against gut in marketing calls10:20 What AI actually does to efficiency18:15 Buying Imaginuity instead of building22:40 The capital strategy behind the deals34:20 Culture clash and why integrations fail39:45 Owner dependency and the exit trap50:35 Valuation myths and truck math01:04:00 The real cost of a bad hire01:20:45 The power of family operating agreementsNewsletter: thedealtablepodcast.com/connectAs a Man Thinketh: amzn.to/4i4Y1GgLane Carrick on selling a business, The Optima Advantage: amzn.to/48nLElWInstagram: instagram.com/thedealtablepodcast/LinkedIn: linkedin.com/company/the-deal-table/The Deal Table is hosted by Ryan Harper and Lane Carrick, filmed in Dallas, and produced by Harper Belmont Media.