The 18 Month Seller: How to Stay in Touch With an Owner Who Is Not Ready to Sell
An owner who says not yet is giving you a timeline. Here is the cadence and the exact texts that keep you the first call 12 to 24 months later.
By Brett Kaufman. 8 years using relationships to build sales pipelines, from political fundraising to a 7 figure business to running matchmaking for two communities. Over 1,000 introductions facilitated.
To stay in touch with a business owner who is not ready to sell, stop treating “not yet” as a no. Treat it as a date you do not know yet. Send short notes on a light, predictable rhythm, each tied to something real in his world, and never ask whether he has changed his mind.
That is the whole job. The hard part is doing it for 18 months while you work live deals.
You know the call. Good business, good owner, real chemistry. Then he says it. “I’m not there yet. Maybe in a couple of years, once my son decides if he wants it.” You say you understand. You mean it. Then six months go by, and you have not said a word to him since.
“Not yet” is the most common answer
Most owners are early, not unwilling. In an Exit Factor survey of 1,104 US small business owners run by Researchscape in August and September 2026, 47 percent said it feels too early to think about an exit. Only 15 percent had a formal, written exit plan. A third had taken no steps at all.
Read that as a buyer. Almost every owner you talk to is on a timeline he has not written down. He will not wake up one morning ready. Something will happen. A health scare, a partner who wants out, a key employee leaving, a kid who says no, a bad quarter, a great quarter. When it does, he calls someone he already trusts.
The Exit Planning Institute puts the stakes plainly: in its words, only 20 to 30 percent of businesses that go to market actually sell. The owner who sells quietly to someone he already trusts never has to find out which side of that number he lands on. You want to be that someone.
Write down the sentence he said
The owner always tells you what he is waiting for. Usually in one line. Usually you forget it.
“Once my son decides.” “After we renew the big contract.” “When my partner turns 65.” “Not until the new building is paid off.”
That sentence is your calendar. It tells you what to watch for and what to ask about later. Write it down within an hour of the call, word for word, with the date.
This is the one habit I would never skip. My whole career has run on it. After every conversation I write down what the person told me and what mattered to them, and I use it the next time we talk. People feel remembered, and they keep coming back. Eighteen months from now, “Did your son end up joining the business?” is a real question. “Just checking in” is not.
The 18 month cadence
You are not running a campaign. You are staying familiar. Each touch should take him 10 seconds to read and ask nothing of him.
This is my rule of thumb for the rhythm. Adjust it to the owner. The examples are illustrative, so swap in his details.
Month 1. Close the loop. Thank him and show you listened.
Thanks again for the time Tuesday. Really enjoyed hearing how you built the route business from two trucks. No agenda on my side, just glad we met. Talk soon.
Month 3. Bring something useful. An article about his industry, a vendor, a person worth knowing.
Saw this piece on fuel surcharges for regional carriers and thought of you. Curious if you are seeing the same thing. Also happy to connect you with a fleet CFO I know if useful.
Month 6. Ask about him, not the sale. Reference the sentence.
Hey Mike, been thinking about our conversation. How did the contract renewal with the county go? Hope it landed your way.
Month 12. Name the time, lightly. You can name the relationship without naming the deal.
Hard to believe it has been a year since we first talked. Still the best run shop I have seen in the space. Coffee next time I am in Tulsa? Would love to catch up.
After month 12, settle into roughly every three months, plus any time something happens in his world: a new hire, an award, a local news story, a competitor selling. The rhythm matters less than the reason. A note with a reason never feels like pressure.
None of these mention the acquisition. They do not need to. He remembers who you are. When the trigger hits, your name is the one already in his phone with a recent date next to it.
What not to send
- “Any change on your end?” He hears: are you ready yet. Every version of this resets the clock on trust.
- A valuation pitch nobody asked for. If he wants a number, he will ask.
- A mass newsletter. It tells him he is on a list. He is not on a list. He is one of a few owners you actually want.
- Silence, then a burst. Five notes in two weeks after nine months of nothing reads as desperation.
If you need language for the touches in between, see how to stay in touch without being pushy.
Watch for the turn
The owner rarely says “I’m ready.” He says something next to it.
He mentions he is tired. He asks what businesses like his are going for these days. He tells you his CPA brought up succession planning. He hires a COO. He posts about his partner retiring. He stops talking about next year’s plans.
Each one is a reason to suggest a real conversation. Not an offer. Coffee, or a call. “Sounds like a lot is changing. Want to grab lunch next month?” That is how an 18 month relationship becomes a first look.
The advisors around him are watching the same signals. His accountant often knows before he does, which is why CPAs are a deal source worth staying close to. Keep both relationships warm and you hear about the turn twice.
Why this is the real off market edge
Most writing on finding off market businesses for sale is about intermediaries: the attorney, the CPA, the broker who has not listed yet. That works, and it is competitive, because the intermediary calls whoever she heard from last.
The owner who told you “not yet” is different. Nobody else may know he is thinking about it. There is no short list yet. There is you, if you stayed, and there is whoever shows up after he finally calls a broker.
The math is simple, and this is illustrative. Say you have had real conversations with 30 owners in the last two years, and most of them said some version of not yet. If a few of them hit their trigger in the next 18 months, those are the deals. The only question is who they think of first.
Ten minutes a day
Holding 30 owners on an 18 month rhythm, by memory, while you work live deals, does not happen. The notes slip at month 4 and the relationship goes quiet. I tracked people by hand for years. It works, and it eats hours a week. That is why I built FRONT OF MIND.
It does the remembering. It opens on your 10 minutes for today, and each person comes with one line saying why today: he posted, his company was in the news, a follow up is due, or he is going cold. Each draft is a text style message, 40 words max, written in your voice. Nothing sends without your tap, and it learns from every edit. Capture lets you say his name and the sentence he told you out loud right after the call, so it is there when month 6 comes around.
Start free with your first 25 contacts and see which owner comes up first.