The most expensive mistake I see sellers make isn't in the negotiation. It's in the timing.

They decide they're ready to sell. They call a broker. They list within 90 days. And then they spend the next 12 months watching buyers walk away from problems that were entirely fixable — if only they'd had the time to fix them.

Why "when I'm ready" is too late

The issues that kill deals or reduce sale price almost universally fall into one of two categories: things that take time to fix, and things that require proof of a track record.

Owner dependency takes 12–24 months to meaningfully reduce. You can't transfer key customer relationships in 90 days. You can't build a management layer in a quarter. You can't create 18 months of clean financials in 6 months.

Tax issues that have been accumulating for years don't resolve quickly. A lease that's expiring in 18 months becomes a deal-breaker if you don't have a renewal in place before you list. Employee agreements and non-competes need to predate the sale conversation by long enough to be credible.

When sellers start preparing the day they decide to sell, they're stuck with their business as-is. And businesses as-is — especially founder-led businesses in the $1M–$5M range — have predictable problems that buyers discount heavily.

What the 12–24 month window actually buys you

Time to build systems. Document your key processes. Build the reporting that lets someone other than you understand how the business is performing. Create the infrastructure that proves the business can run without you.

Time to clean up the financials. Work with your CPA to understand what your books look like to a buyer or lender. Address the inconsistencies. Separate the personal expenses. Build the add-back schedule.

Time to fix the easy legal issues. Get your customer contracts in order. Make sure your key employees have agreements in place. Resolve any outstanding disputes. Confirm your business licenses and registrations are current.

Time to grow into a better multiple. Businesses that have shown consistent or growing revenue over 2–3 years sell for better multiples than businesses that are flat or declining. The trend matters. If you have time to demonstrate upward momentum, use it.

The businesses that close at the right price

When I work with clients who started preparing 18–24 months before they wanted to list, the deals look different. The financials are cleaner. The customer base is more diversified. The key employees are locked in. The owner has been systematically stepping back from day-to-day operations.

These businesses attract more buyers, move through due diligence faster, and close at higher multiples. Not because the sellers got lucky — because they used the time they had.

The question isn't "when should I start preparing?" The answer to that is always "earlier than you think." The real question is: how much of the premium you're leaving on the table are you willing to give back in exchange for not having started yet?

What to do right now

If you're 1–3 years from wanting to sell, the single most valuable thing you can do is get an honest assessment of where your business stands today. Not from your broker — they're incentivized to list you — but from someone whose job is to tell you what a buyer is going to find.

The issues you find now, you have time to fix. The ones you find in the data room, you don't.