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$5M - $50M Business Exits & What You Should Know with Anthony Franco
Episode 340
In this power-packed episode, Jaryd Krause sits down with serial founder and dealmaker Anthony Franco, a man who knows exits inside and out. Having built and sold seven companies—six of them successfully, including two to publicly listed firms—Anthony brings rare, battle-tested wisdom to the table.
Together, they dig into what it really takes to engineer a successful exit in the $5M–$50M range. From preparing your business to maximize valuation, to structuring deals that minimize risk for both buyers and sellers, Anthony shares the strategies he’s used to navigate countless transactions. He doesn’t sugarcoat it either—every deal has “hair” on it, and this conversation unpacks exactly how to handle those messy, unexpected challenges that can tank a deal if you’re not prepared.
You’ll learn:
✔️ How to structure an exit so you walk away with more security and better terms
✔️ Why taking your foot off the gas before closing can destroy your valuation
✔️ How buyers can avoid catastrophic mistakes by spotting risk early
✔️ What makes a business truly attractive to both strategic and financial buyers
✔️ The evolving role of AI in business growth, exits, and even the future of work
Whether you’re eyeing a future sale, planning to acquire, or just want to build a business that’s more valuable and resilient, this episode is a masterclass in deal-making straight from someone who’s been through it all.
🎧 Tune in now to hear how to prepare, structure, and execute smarter exits.
Episode Highlights
04:50 – Clean books, systems, and reduced key-person dependency: the essentials for any exit.
06:50 – Why every exit is messy—buyers always renegotiate during LOI.
08:30 – Sophisticated vs. inexperienced buyers: how the right questions signal experience.
09:35 – Knowing what really matters in due diligence vs. what’s just “wonky” small-business noise.
11:20 – Why trust and fairness between buyer and seller are critical when numbers vary near close.
12:50 – Sellers must keep operating like they won’t exit—taking the foot off the gas can kill deals.
18:00 – Why tax planning is just as important as negotiating the sale price.
25:40 – Selling fast matters—waiting too long risks copycat competitors and valuation drops.
27:40 – Regulation, trucking, and AI adoption: why safety perception, not data, drives adoption speed.
Key Takeaways
➥ Prepare early. Clean financials, diversified revenue streams, and reduced key-person dependency are critical to maximizing valuation.
➥ Buyers are risk-averse. Expect tough questions in due diligence—not personal attacks. Sophisticated buyers ask the right way, but all buyers are trying to mitigate risk.
➥ Deal structures matter. Cash is king for sellers. Earn-outs, seller notes, and rollover equity all come with risks—align them with your personal life stage and goals.
➥ Don’t take your foot off the gas. Deals can drag on for months. Keep running your business as though it won’t sell; growth during due diligence strengthens your negotiating power.
➥ Surround yourself with the right advisors. A good CPA and financial advisor can save millions in taxes and structure your exit properly.
➥ AI is changing the game. It will automate “crappy work,” commoditize parts of business, and put greater emphasis on distribution, brand, and audience trust.
➥ Faster is better. Once you decide to sell, speed matters—because markets and competitors don’t wait.
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Published on 12 hours ago