I still remember the call. It was 11:47 p.m. on a Tuesday, and a business owner I have known for years was on the other end of the line, talking fast. He had signed a letter of intent that morning. By dinner, he was sweating through his shirt.
His words stuck with me: “I thought I could wing it. I built this company from nothing, so how hard can selling it be?”
Hard. Really hard, actually. 😅
That call is why I keep preaching the same sermon to founders: start your exit planning two years early. Not six months. Not “when the market feels right.” Two years. Here is why that gap between now and the closing table is the difference between a clean handshake and a slow-motion panic attack.
Why a Last-Minute Sale of Your Business Quietly Costs You Money
Let me be blunt, friend to friend. A last-minute sale does not just feel stressful. It bleeds value.
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Buyers can smell desperation. When you are rushing, they know it, and they price accordingly.
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Due diligence becomes a fire drill. Every missing document and messy contract turns into a negotiation chip against you.
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Your team senses something is off. Key people start polishing their resumes before you have even told them what is happening.
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You accept the first decent offer because you have no leverage and no time to wait for a better one.
A friend of my who works at Tampa Business Brokers Lab (tampabusinessbrokerslab.com) told me how he has watched owners leave real money on the table simply because they showed up to the party late. It is like selling a house with a leaky roof and hoping nobody notices. They notice.
What Two Years of Exit Planning Actually Buys You
Here is the part people miss. Exit planning is not about picking a buyer. It is about making your business worth buying, well before anyone knocks.
1. Clean Books Make Buyers Relax
Nothing kills momentum faster than a buyer’s accountant squinting at your financials like they are decoding a secret language. Two years gives you time to clean up your records, separate personal expenses from business ones, and get a professional review done. Do that early and watch how differently buyers treat you.
2. Recurring Revenue Sells Itself
Buyers pay a premium for predictable income. If your revenue depends on you personally charming every client, that is a red flag. Spend your runway building contracts, retainers, and systems that keep money coming in whether you are in the room or not.
3. Your Team Becomes Part of the Story
A business that runs without you is worth more. Full stop. Use those two years to hand off real responsibility, document processes, and let leaders step up. When a buyer sees a team that operates smoothly without the founder hovering, the pitch gets a whole lot easier.
4. You Get to Choose Your Timing
When you plan early, you are never forced to sell. You can walk away from lowball offers, wait out a rough quarter, and negotiate from a position of strength. That is worth more than any clever negotiation tactic, honestly.
The Math That Changes Everything
Think about it this way. Say your business sells for a multiple of its earnings. A rushed sale might land at the low end, or worse, trigger a discount for “risk.” A well-prepared exit at the top end of the range can mean a difference that dwarfs any savings from cutting corners early.
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Rushed exit: buyer names the terms, you nod along.
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Planned exit: you name the terms, buyers compete.
That gap is often seven figures. For real. I have seen it.
The Prep Checklist I Wish Every Owner Used
Nothing fancy here. Just the stuff that matters.
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Get a valuation done now, not later. You cannot improve what you have not measured.
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Fix your financial house. Clean statements, clear add-backs, no mystery expenses.
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Reduce your dependence on you. Document what only you know.
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Build recurring revenue. Contracts beat handshakes.
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Assemble your team early. A good advisor and an accountant who has done deals before will save you a fortune.
Start on that list today and you will sleep a lot better. Trust me on that one. 😴
A Quick Word on What Not to Do
Do not tell your entire staff you are planning to sell two years out. Loose lips sink deals, and panic spreads fast. Keep your inner circle tight, work with advisors who have done this before, and let the plan stay quiet while the business gets stronger.
Also, do not confuse activity with progress. Spending two years “thinking about it” is not planning. I have met plenty of owners who talked about exiting for a decade and never did one concrete thing. Do not be that person.
Final Thoughts
That 11:47 p.m. caller? He got lucky. His deal closed, but only after he paid a price he did not need to pay. Six months later he told me the same thing I am telling you now: “I should have started earlier.”
Starting early does not just protect your money. It protects your sanity, your team, and your legacy. Give yourself those two years. Your future self will thank you, probably with a much nicer boat. 🚤
Frequently Asked Questions
How early should I start exit planning?
Two years is the sweet spot. It gives you time to clean up your financials, reduce your dependence on yourself, build recurring revenue, and choose your timing instead of reacting to it.
Can I sell my business in six months instead?
You can, but you will likely pay for it. Rushed sales tend to attract lower offers, tougher due diligence, and buyers who know you are under pressure.
What is the single most important step?
Get a valuation done early. You cannot improve what you have not measured, and it sets the baseline for every decision that follows.
Should I tell my team?
Be selective. Keep the plan inside a small circle of trusted advisors until the deal is real, then communicate carefully and clearly.
Does exit planning only matter if I actually sell?
Nope. A business that is ready to sell is usually a better business to run. Clean books, strong teams, and recurring revenue help you every single day, whether you exit or not.