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Episode Summary
You don’t get to decide when you sell your business. The buyer does. And the day the LOI lands, everything changes: you go from prom queen to hostage in about 24 hours. Stuart Sorkin has watched this play out for 30+ years, and his book Expensive Mistakes (co-authored with Dick Stieglitz) is the one I wish I’d read before my dad and I sold our company. We got into the mistake that costs owners the most money: a vague exit strategy that ignores how tax planning, estate planning, financial planning, and corporate structure are one big Rubik’s Cube, not four separate buckets. We got into how to golden-handcuff your key team without writing checks that walk out the door at closing. Why 60% of deals at LOI never close (most often because nobody built the due diligence library before the buyer asked for it). And the punchline that should reframe how you think about your role: the most valuable version of your business is the one you’ve already stepped out of. Real numbers, real structures, and the lesson my family learned the hard way.
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## Top 10 Takeaways- Your business will sell when someone wants to buy it, not when you want to sell it. Be ready before the LOI.
- Run a Monte Carlo on your personal number first. Then compare it to the business value. The delta drives every decision.
- A positive delta unlocks tax structures that move money to family or charity instead of the IRS.
- Golden handcuffs that pay out at closing aren’t handcuffs. They’re severance.
- Make key employees buy their equity out of after-tax bonuses. The ones who won’t are paycheck players, not partners.
- Your due diligence library should be updated quarterly, not assembled the month after the LOI lands.
- Earnouts work only if you trust the buyer with your baby and you control what the formula actually measures.
- S-corps doing year-end tax planning during a sale year crater the acquirer’s financing model. Plan around it.
- Tax, estate, financial, and corporate structure are one Rubik’s Cube. Solve them together or pay for it twice.
- The most valuable version of your business is the one you’ve already stepped out of.
Sound Bites
“You’re all wrong. You’re going to sell it when someone wants to buy it. Therefore, you always have to be ready for sale.” (@TBD) — Stuart Sorkin
“Most entrepreneurs spend 99% working in their business and 1% on their business.” (@TBD) — Stuart Sorkin
“Until you get the LOI you are like the prom queen and everyone wants to date you. The minute you sign the LOI the shoe is on the other foot and the acquirer will do everything they can to potentially reduce the price.” (@TBD) — Stuart Sorkin
“The best way to sell your business is when you’re an absentee owner. That’s when the business is most valuable, because the one thing that’s going to happen after the acquisition is the owner isn’t going to be there.” (@TBD) — Stuart Sorkin
About This Episode
Stuart Sorkin is an M&A attorney and CPA with over 30 years advising small and mid-sized business owners on transactions, estate planning, and corporate structure. He holds a JD, LLM, and CPA, and is co-author of Expensive Mistakes When Buying or Selling a Business with Dick Stieglitz. The book catalogs 57 of the most common mistakes Stuart has watched owners make on both sides of a deal, published in 2010, the first year baby boomers turned 65. This episode is a working tour through the ones Ryan wishes he’d read before selling his own company.
Resources Mentioned
- Expensive Mistakes When Buying or Selling a Business — Stuart and Dick Stieglitz’s book covering 57 common deal mistakes.
- Stuart’s website — stuartsorkin.com
- Stuart’s email — ssorkin@shspc.com
- The Value Builder System (John Warrillow) — Referenced for the eight key drivers of company value.
- The Snowball by Alice Schroeder (on Warren Buffett) — Referenced for the Berkshire model of ownership: understand the business, delegate, read the financials.
- Todd Ganos (Ep. earlier in the feed) — Referenced on why specialists keep their continuing ed sharp and generalists don’t.
Connections
Phase + Module:
- Module 9 — Operator Transition — The absentee-owner thesis is the operator transition in one sentence
- Module 7 — Leadership Team — Stuart’s three-legged stool (finance, sales, delivery) maps directly to functional leaders
Milestones:
- Milestone 19 — Functional Leaders — Building the team so you’re not the biggest backup in the business
- Milestone 24 — Long-Term Value Plan — The equity-buy + stay-bonus + funded non-compete structure for key employees
- Milestone 3 — Net Worth & Valuation Targets — The personal number that anchors every sale-side decision
Concepts referenced:
- The Owner-Operator Trap™ — The owner as the biggest backup, surrounded by yes men
- Value Gap — The delta between what you need and what your business is worth
- The Four Value Levers — Transferable value as an explicit lever, not an accident