FOR FIRST-TIME SELLERS
What selling actually looks like.
Most owners sell a company once. If you’ve never been through it, the process can feel deliberately opaque: a series of requests and terms nobody explains, arriving while you’re still running the business. Here’s the honest version, start to finish.
THE PROCESS
Every deal is different, but this is the shape of most of them.
01 — A first conversation: No NDA, no financials, no materials. Thirty minutes to understand what you’ve built and what you want out of the next few years. Nothing binding, and plenty of people have this conversation two years before they’re ready to do anything.
02 — Confidentiality and a first look at the numbers: If it makes sense to keep talking, we sign an NDA and you share the basics: two or three years of profit and loss, revenue by customer, headcount. Usually a week or two, and enough for me to tell you whether this is real.
03 — A preliminary range: I come back with a value range and the reasoning behind it. Not an offer, and not binding, but it tells you early whether we’re in the same neighborhood, before you’ve invested months.
04 — Letter of intent: This sets price, structure, your role afterward, and a timeline. It’s non-binding on the deal itself, but the exclusivity and confidentiality provisions do bind, so it’s the point where you stop talking to other buyers. Usually two to four weeks to negotiate, and worth taking seriously: most of what matters gets decided here, not later.
05 — Diligence: The longest and hardest stretch, typically sixty to ninety days. A quality of earnings review examines your financials in detail, particularly your add-backs. Legal counsel reviews contracts, corporate records, and litigation. There’s a customer and contract review, an insurance and benefits review, and in this industry a real compliance component: DOT, chain of custody, HIPAA, credentialing, and whatever else your specific work touches.
06 — Documentation and financing: Purchase agreement, disclosure schedules, and the working capital peg, the amount of working capital that has to be in the business at close. It sounds technical and it’s worth understanding, because a peg set badly is a price reduction by another name.
07 — Close and transition: Funds move, ownership changes, and the part that actually matters starts. What that looks like depends on what we agreed, which is why your role after close is a letter-of-intent conversation rather than an afterthought.
Total timeline: typically four to seven months from a serious first conversation to close, though it can move faster when the business is well documented and the parties are aligned.
I should be clear about one thing. Everything above describes a direct sale to a single buyer, which is what a conversation with me looks like. A banked process runs differently. Your investment banker prepares a confidential information memorandum. You give management presentations. Several buyers submit indications of interest. Both the timeline and the work on your end go up. Both routes are legitimate. They just aren’t the same, and this page describes the one I’m part of.
WHERE DEALS STALL
Diligence is where deals die, and in this industry it’s usually the same six things.
Every list like this one carries add-backs and customer concentration. Here’s the version specific to healthcare logistics, and what you can do about each one before anyone is looking.
Driver classification — If your drivers are 1099 contractors, this is the most common single reason a courier acquisition falls apart. Buyers assume they’ll inherit any classification exposure, and they price accordingly. WHAT TO DO: Have an employment attorney compare your driver agreements to how the work actually runs day to day. The practice is what gets tested, not the wording.
Contract assignability and change of control — Hospital system and GPO agreements often carry change-of-control provisions. WHAT TO DO: Pull your top contracts and read the assignment and change-of-control clauses now. You just need to know which ones will need consent and who signs.
Credentialing and chain of custody — Background checks, HIPAA training, immunization records, facility badging, signature capture, and temperature logs are part of what the customer is buying. WHAT TO DO: Pick your largest customer and try to reconstruct a complete chain of custody for one ordinary day of work. Whatever’s hard to produce is exactly what a buyer will ask for.
DOT files and compliance history — Driver qualification files, drug and alcohol testing, CSA scores, and vehicle maintenance records get reviewed in every transportation deal. WHAT TO DO: Audit your driver qualification files against current requirements and close what’s missing.
Contracted routes versus handshake volume — Revenue running on relationships is real, but buyers value it differently than contracted work. WHAT TO DO: Map what share of revenue sits under a signed agreement with a remaining term, and what’s running on trust. Paper any renewal you can before a sale.
Add-backs and owner dependence — Personal vehicles on the books, family on payroll, and a dispatcher relationship that’s really just you all get tested. WHAT TO DO: Write down what only you do, then hand one of them to someone else this quarter. Keep backup for your add-backs, and ask your CPA for an accrual view if your books are cash basis.
None of this is unfixable. All of it is far cheaper to fix now than to explain in the middle of diligence.
Two things worth knowing.
Get your own advisors — An attorney with transaction experience and a CPA who understands your books. I’d rather negotiate with a well-advised seller: deals with a competent counterparty on the other side close more often, not less.
The tiring part isn’t the negotiation — It’s diligence. It arrives while you’re still running the company, and it goes on for weeks. Knowing that going in is most of what makes it survivable.
If any of this raises questions about your own situation, ask me. I’m happy to walk through it whether or not we ever do a deal.
WHAT DRIVES VALUE
What actually moves the number in these businesses.
I won’t put multiples on a website. They move with the market and they vary enormously by what you’ve built. Anyone quoting you one without seeing your financials is guessing. What I can tell you is what a buyer is looking at while they build the number.
Route density — How much revenue you produce per mile driven. Two companies with identical revenue can have very different margins depending on how tightly the stops cluster. Density is also hard for a competitor to replicate quickly.
Contracted volume — Revenue under a signed agreement with a remaining term is worth more than the same revenue running month to month. That’s most of the gap between two businesses that look the same on a profit and loss.
Customer concentration — One health system at sixty percent of revenue isn’t automatically a problem, particularly if it’s contracted and the relationship is decades old. It does tend to change the structure.
Driver model — W-2 with low turnover is worth more than 1099 with high turnover. Classification risk is only part of why. A stable bench is what lets a business absorb new volume without breaking.
Customer and payer mix — Hospital systems, reference labs, retail pharmacy, and specialty pharma don’t behave alike. They pay on different terms and renew on different cycles. Their growth curves don’t look alike either.
Contract length and renewals — A three-year agreement with two prior renewals tells a buyer more than almost anything in the financials. It’s evidence the customer keeps choosing you when they have the chance not to.
Almost none of these move in a month. Most of them move over a year or two, which is a good argument for having this conversation before you’re ready rather than after.
FAQ
Questions owners think but don’t always ask.
Will you keep my people? — I’m not buying a business in order to cut it. The team is most of what I’m paying for.
Can I stay involved? — If you want to, yes, in a continuing role, advisory seat, or equity in what comes next. It’s a preference, not a condition.
Can I keep a piece of the business? — Yes. Rollover equity lets you sell most of the company while retaining a minority stake in what it becomes.
Do I need to hire an investment banker? — Not to talk to me. You should have your own attorney and CPA before signing anything.
How do I know you can actually close? — Capital is committed before we talk, and I’m happy to show you how it’s structured.
What happens if we don’t agree on price? — Then we don’t do a deal. I’d rather find that out in week two than week twelve.
Is this confidential? — Completely. Nothing moves faster than you want it to.
How long does this take? — Typically four to seven months from a serious first conversation to close.
What if I’m not ready to sell? — Reach out anyway. Many people I speak with are two or three years out.
What if my business isn’t exactly what you described? — Reach out. The criteria are a guide rather than a filter.
Let’s talk about your business.
If you’ve built a business in healthcare logistics and you’re starting to think about what comes next, I’d like to hear from you. A first conversation carries no obligation and no timeline.