Most owners start thinking about their exit 6 months before they want to sell. That's about 5 years too late.

I'm a business broker and I work with owners in the $2-30M range (usually $1m+ ebitda). The biggest mistake I see — over and over — is owners coming to me ready to sell, only to find out they left serious money on the table because they didn't plan ahead. A few things that need years to set up properly: QSBS (Qualified Small Business Stock) — If you're structured right, you could exclude up to $10M in capital gains from federal tax when you sell. But you need to have held qualifying stock for at least 5 years. If you're not set up for this now, you can't retroactively fix it at closing. Owner dependency — Buyers pay more for businesses that run without the owner. If you're the rainmaker, the key relationship holder, and the only one who knows the passwords, that takes 2-3 years to unwind properly. Clean financials — I can't tell you how many deals fall apart in diligence because the books are a mess. Running personal expenses through the business, inconsistent reporting, no real P&L. Getting 2-3 years of clean, tax-ready financials before going to market makes a massive difference in valuation. Customer concentration — If one client is 30%+ of your revenue, that's a risk factor that tanks your multiple. Diversifying your revenue base takes time. Even if you're not planning to sell for 5-10 years, the things that make your business sellable are the same things that make it a better business to run. Start the exit planning now. Future you will be grateful. Happy to answer any questions about the process — I've seen a lot of deals go right and a lot go sideways.