IBA, as the premier business brokerage firm in the Pacific Northwest, is firmly established as a respected professional service firm in the legal, accounting, banking, mergers & acquisitions, real estate, and financial planning communities. Periodically, we will post guest blogs from professionals with knowledge to share for the good of owners of privately held companies & family businesses. The following blog article has been provided by Rachel Lugo of Stella and Main (https://stellaandmain.com/):
Selling Your Business Is Going to be Harder Than You Think — Here’s How to be Ready for It
You’ve spent years building something. Maybe decades. You made payroll when it was hard, stayed late when everyone else went home, and made decisions that kept the doors open through things that would have broken a lot of people. Your business isn’t just a revenue stream. It’s woven into who you are.
So when you decide to sell — really decide — the assumption is that the hard part is behind you. You built it. Now someone’s going to pay you for it. What’s left to navigate?
A lot!
Due Diligence Is Not a Compliment
When a buyer submits a letter of intent and due diligence begins, you’re going to be handed a list of questions. Financial records. Contracts. Employee details. Operational documentation. Customer concentration data. Tax returns. The list seems endless.
One seller I spoke with — a 25-year founder who built a specialized services company and knew his business inside and out — described the due diligence process as feeling like getting “smacked in the face.” Not because the questions were unfair. But because they felt obvious to him, almost patronizing. Why are they asking me this? I’ve been doing this for 25 years.
That reaction is more common than most people admit. And it matters, because how you respond to it — emotionally, not just logistically — can affect the outcome of your deal. A seller who becomes defensive, who drags their feet on documentation, or who takes the questions personally gives buyers exactly what they’re looking for: evidence that the business is harder to understand from the outside than it should be.
The due diligence list isn’t an attack. It’s a buyer trying to confirm that what they’re paying for is what they think it is. The more prepared you are going in, the less it stings — and the less leverage they have to lower your price.
You’re Not Just Selling a Business. You’re Losing Part of Your Identity.
This part is rarely talked about in business sales conversations, and it probably should be.
For most founders, the business and the identity are the same thing. You are the owner. You are the expert. You are the one people call. When that ends — whether it ends on closing day or six months later when a transition period wraps up — there’s a version of yourself that disappears with it.
That transition tail, the period after the sale where you’re still involved but no longer in charge, is often where sellers struggle most. I spoke with a couple who sold their home inspection company — a business they’d built to nearly a thousand five-star reviews — to a friend and longtime customer. The deal was structured well. The buyer was someone they trusted. And yet the husband found himself stuck in an open-ended training period that dragged on far longer than expected. They couldn’t launch the next chapter of their lives until it was over. What should have felt like freedom put them in limbo for a while.
How long the tail is, how clearly it’s defined, and whether you have something waiting on the other side of it — these things matter enormously to whether sellers feel good about their exit a year later, or whether they spend that year second-guessing.
Seller Regret Is Real, and It’s Preventable
Studies on seller satisfaction after a business exit consistently show that a meaningful percentage of sellers regret the sale within the first year. Not because they got a bad price. Not because the buyer turned out to be terrible. But because they weren’t ready for what came next.
The financial readiness and the emotional readiness are two different things, and most of the focus goes into the financial side. What will I net after taxes? Is the multiple fair? Will the SBA loan come through?
The sellers who come out the other side feeling good about their decision tend to share a few things in common. They went into the process clear on why they were selling. They had a plan for what came next — not a vague idea, but an actual plan. They understood the transition period upfront and negotiated its terms carefully. And they didn’t let the due diligence process catch them off guard.
How to Not Be One of the Statistics
The way to avoid regret isn’t to talk yourself out of selling. It’s to go in prepared.
Get clear on your number — not just the asking price, but what you actually need to walk away with after taxes, broker fees, and any seller financing you’re carrying. Know that before you list.
Define your transition period before you sign anything. Open-ended commitments to train the new owner sound reasonable when the deal is exciting. They feel like a trap six months later when the buyer keeps extending. Put a hard end date in the agreement.
Know what comes next. The sellers who transition well almost universally had something they were moving toward — a new project, a retirement they’d actually designed, a next chapter with real shape to it. The ones who struggle didn’t plan what came after their exit.
And start getting your business ready — not when you decide to sell, but years before. Not because buyers are unreasonable, but because a business that’s clean, documented, and not dependent on you personally gives you options. You can sell when you want to, to the buyer you want, at a price that reflects what you actually built — rather than whatever a buyer can negotiate you down to when they find the gaps you didn’t fix.
The sale of your business should be one of the best outcomes of your working life. With the right preparation — financial and emotional — it can be!
If you have questions relating to the content of this article, Rachel Lugo, founder of Stella and Main, would welcome the opportunity to connect. Stella and Main is a Puyallup-based firm specializing in operational exit readiness for founder-led businesses with $1M–$5M in revenue. Rachel works with business owners in the years before they go to market — addressing owner dependency, undocumented processes, revenue concentration, and the operational gaps that tend to cost sellers money or kill deals in diligence. Rachel can be reached at (253) 314-4335 or [email protected].
IBA, the Pacific Northwest’s premier business brokerage firm since 1975, is available as an information resource to the media, business brokerage, mergers & acquisitions, and real estate communities on subjects relevant to the purchase & sale of privately held companies and family businesses. IBA is recognized as one of the best business brokerage firms in the nation based on its long track record of successfully negotiating “win-win” business sale transactions in environments of full disclosure employing “best practices”.