Key Principle
Selling is not an event; it is a sequenced process of discovery, run in ordered phases. Preparation and early disclosure — not negotiation cleverness — determine the outcome. Diagnose whether to sell before how; reduce owner reliance before going to market; disclose flaws before they are discovered; read every offer as amount × timing × probability of cash, not a number; and treat the buyer's character and funding as load-bearing because most consideration is deferred and discretionary. A misdiagnosed motivation produces a mis-built deal.
Why This Matters
Selling is usually a once-in-a-lifetime event for the least-experienced person in the room, facing repeat-player buyers. The marketplace is messy — opaque, low-trust, disorganized. Fewer than 25% of sub-$15M-EBITDA deals close after the LOI. The owner who runs this as an improvised, price-maximizing scramble loses control of the one transaction they cannot redo. The owner who runs it as a disciplined, phased process — quarterbacking their own deal while extending capacity through advisors — keeps control, surfaces deal-killers when they are still cheap, and lands a deal that actually serves their reason for selling.
The Playbook (Phase by Phase)
Phase 1 — Decide (do you actually want to sell?)
- Run the seven root motivations test: personality/skills, exhaustion, freedom, health, obligations, risk, legacy. If your driver is money, stop — "You'll almost always do better financially, assuming the company continues to perform, by not selling" (Do You Actually Want to Sell?).
- Reject the false eighth motivation, "timing the sale." Trying to top-tick a cycle is fool's gold and selects for bad-faith buyers. "Be a seller that attracts a great buyer" (Do You Actually Want to Sell?).
- Answer the Magic Wand / "What does winning look like?" question across role, the company's future (close / 3yr / 10yr), process, stakeholders, and finances (What Does Winning Look Like?).
- Complete the Purposeful-Path Self-Assessment (cash range net of debt/tax/fees, years willing to stay, post-sale role, ideal buyer values, % of equity to sell). Can't answer? That gap is the signal you're not ready.
- Biggest pitfall: Selling for money. A sale trades an indefinite earning stream for finite, partly-deferred proceeds — passive returns rarely match the business you gave up.
Phase 2 — Prepare
- Reduce owner reliance — the single biggest suppressor of both price and probability of closing. Build a leadership team that can stand on its own.
- Clean up financials and inventory deal-killers across the five categories (management, operations, financial, legal, non-business); disclose them early, "warts and all." The same fact is a priced risk if disclosed early and a deal-killer if discovered late.
- Lower expectations deliberately — happiness = reality − expectations.
- Plan stakeholder communication: everyone's first thought is "What does this mean for me?" Preempt the fear; never lie. Hold announcements until "the ink is dry and the check clears."
- Biggest pitfall: Hiding flaws to protect the price. Concealment converts a manageable, priced risk into a trust-destroying deal-killer or re-trade in diligence.
Phase 3 — Assemble the team
- Hire an intermediary (makes the market + manages diligence), an M&A attorney (not a generalist — "purchase agreements are different beasts"), and a tax advisor (proceeds allocation: capital gains vs. ordinary income).
- Pick advisors deliberately (six traits; Larry Bird method); avoid being a whale, minnow, or guinea pig; treat info-hiding by an advisor as a signal to "run."
- Quarterback your own deal. "Assemble enough people with great expertise to... extend your capacity, but do not delegate judgment" (Appendix B).
- Keep the circle of trust as small as the workload allows; have a senior financial employee — not you — quarterback the diligence data pull.
- Biggest pitfall: Delegating judgment. Advisors walk away whole regardless of outcome; you don't.
Phase 4 — Go to market
- Pick a market-creation approach: Auction, Hyper-Target, or Likely Market — matched to your confidentiality tolerance and buyer universe.
- Build the document stack: blind teaser → NDA → CIM → operating documents. Present financials as "reality with context"; lead with defensible add-backs and cash-flow ("beer money"), not rosy forecasts.
- Create a market even if you think you know your buyer — a credible alternative is your leverage.
- Biggest pitfall: "An offering for everyone attracts no one." A vague, un-targeted process generates motion without qualified buyers.
Phase 5 — Negotiate
- Read every offer as amount × timing × probability of cash, decomposed through the waterfall and capital stack — never as a headline number.
- Trade terms, not just price: "you set the price, I'll set the terms." Earnouts, seller notes, NWC peg, caps/baskets all allocate real risk.
- Vet the buyer's funding source — committed capital signals they can actually close; fundless sponsors close ~1 in 10.
- Check your BATNA and lead with proof-of-health over projections; negotiate as swaps, not a single-axis fight.
- Biggest pitfall: Chasing the highest number. The biggest price often carries the worst terms, the weakest funding, and the lowest probability of cash.
Phase 6 — Diligence
- Provide a shared reality: diligence converts your tacit knowledge into verifiable words and numbers. "No one sane is going to pay millions of dollars for something they have not verified to be valuable" (Appendix B).
- Expect <25% of post-LOI deals to close. Diligence reshapes the deal (timeline step 6) — it is not a pass/fail gate on a fixed price.
- Watch for re-trading (bad-faith downward renegotiation) and distinguish it from legitimate re-pricing of newly discovered facts.
- Remember it's a bilateral audition: you're previewing "how the buyer is to work with."
- Biggest pitfall: Treating diligence as adversarial paperwork to survive, missing that the buyer you're vetting controls your deferred consideration.
Phase 7 — Close & transition
- Use exclusivity (60–120 days) as a forcing function, not a deadline — momentum, not a finish line.
- Work the pre-close checklist and accept the "new normal": usually more work, a 1–3-year wind-down, and a new partner — not get-the-money-and-run.
- Keep a Decision Notebook — write down why you sold while the reasons are vivid; it's the antidote to near-inevitable seller's remorse.
- Biggest pitfall: Announcing or mentally checking out before close — you may spook the company for a deal that then collapses.
Common Execution Pitfalls
- Selling for money, or trying to "time" the sale — both produce mis-built deals and attract bad-faith buyers.
- Going to market still indispensable — owner reliance suppresses price and kills closings.
- Concealing flaws — early disclosure prices a risk; late discovery kills the deal or triggers a re-trade.
- Reading a price as a number instead of amount × timing × probability of cash.
- Vetting the checkbook but not the buyer's character or committed capital.
- Optimizing price over terms.
- Delegating judgment to advisors who bear none of the consequences.
- Announcing before the check clears; underestimating the post-close "new normal."
Key Quotes
"You'll almost always do better financially, assuming the company continues to perform, by not selling your company. It's counterintuitive, but correct." — Brent Beshore, (Do You Actually Want to Sell?)
"Be a seller that attracts a great buyer." — Brent Beshore, (Do You Actually Want to Sell?)
"The buyer wants to see that the company's leadership can stand on their own." — Brent Beshore, (Big News / What Does Winning Look Like?)
"Assemble enough people with great expertise to... extend your capacity, but do not delegate judgment." — Brent Beshore, (Appendix B)
"No one sane is going to pay millions of dollars for something they have not verified to be valuable." — Brent Beshore, (Appendix B)
Rules of Thumb
- Decide whether before how; if the answer is "money," keep the company.
- Disclose early: a flaw priced is survivable; a flaw discovered is fatal.
- Reduce owner reliance before anyone reads a teaser.
- Quarterback the deal; delegate the load, never the judgment.
- A number is never a number — it's amount, timing, and probability.
- You set the price, I'll set the terms.
- Assume the deal dies (>75% do post-LOI); manage exclusivity as momentum.
- Don't announce until the ink is dry and the check clears; keep a Decision Notebook.