Most of you will skip this one, and it's the article that matters most.
Everyone obsesses over the cold email. Almost nobody prepares for what happens after it works. The owner replies, the buyer gets excited, and inside two messages he asks for three years of financials and blows up the best lead he's had all year.
What the first conversation is for
One call. Twenty to thirty minutes. One job: find out whether this is a fit, and leave the owner wanting the next conversation.
It is not a pitch. It is not a valuation. It is not a document request. Go in trying to accomplish more than that and you'll accomplish less.
Open by saying who you are
Your name and your role, in one breath. If you're the buyer, say buyer. If you work for a firm, say what you do there.
Owners tell the truth to people who tell the truth first.
Then, in about ninety seconds, frame three things and stop:
Who you are as a buyer. Not institutional private equity, if that's true. An operator. A self-funded buyer. Someone who exited one business and is looking for the next. Owners have strong feelings about who takes over what they built, and most of them have already decided how they feel about PE.
Who pays you, if that's relevant. If you're a firm working for a buyer, say it out loud. "We're paid by the buyer, so this isn't a broker situation where you give up a percentage of your proceeds to be represented." That single sentence reframes the entire call.
What you're optimizing for. "We want to make it a good deal for everyone involved." Plain. Then stop. Don't stack a fourth point.
Ask permission before you ask questions
This is the move that makes everything after it work.
Tell them you have a set of questions, tell them roughly how many, and give them the exit before they need it:
"Anytime during these, you can say let's wait until an NDA, and I'll just note it and move on. It's basic stuff about the business and it helps me know whether I'm even the right fit for you. Good to run through a few?"
Two things happen. You've framed the questions as a fit test for them, not diligence from you. And you've removed the pressure that makes owners stonewall.
Offer the NDA door and most owners walk right past it. We've had owners who raised an NDA before we got to the questions answer every single one, including margin and EBITDA, without ever invoking it. Because we gave them the out.
Trust before numbers
Say this again, because it's the whole thing.
You do not open with revenue. You do not open with EBITDA. You do not open with "what are you looking to get."
You earn the numbers conversation by first establishing who you are and how you protect them. Once that's done, the numbers question is easy and it usually gets answered.
When you do ask, soften it and mean it:
"Do you have a sense of your SDE or EBITDA, even roughly? You don't have to give me a number. Just tell me what you feel would be useful."
That softener is what produces the answer.
The order of the questions
Move from easy to sensitive. Never reorder.
The business. What it does, how it makes money, years in operation, headcount and key roles, how involved the owner is day to day.
The numbers. Profitability, revenue trend, whether financials are current.
The sale. What has him thinking about it, what timeline feels right, whether he has a number in mind, whether he's talked to anyone else.
Risk. Customer concentration, key people, the lease, legal issues.
Fit. What the right buyer looks like to him, whether he'd consider an earn-out or staying on, and whether anyone else is part of the decision.
Three rules that cost the most when broken
Ask, then be silent. The most common failure I see, including from us. You ask "do you have current P&Ls and tax returns?" and then fill the pause with "I figured you probably do." Now you have no answer on the record. Ask the question. Let it sit.
Never write down a number they didn't say. Not in your notes, not in a summary, not in an email to a partner. "Not stated" is a legitimate answer. An estimate you invented becomes a fact three weeks later, and then it's wrong in a model.
When they defer to the NDA, mark it and move on. No push. No "well, ballpark?" Write "to be discussed once the NDA is in place" and go to the next question.
The questions they'll ask you
Three come up almost every time. Have them ready.
"What are businesses like mine trading at?" Give a range, attach it to the buyer, don't commit. Something like: three to four is typical, up to five depending on the buyer, and a strategic changes the math. Then stop talking. Owners frequently price themselves out loud if you give them the range first and stop talking.
"Can we do an NDA before I share numbers?" Yes. Immediately. No negotiating, no explaining why it isn't necessary. Yes, and here's what we can do in the meantime.
"What would you expect from me after closing?" Answer it straight, and use it to pulse-check size at the same time.
How to close the call
Three parts.
Name what happens next, with a person attached to it. Vague next steps kill momentum.
Take the pressure off the timeline: "If the fit isn't there right now, that's fine. This could be a now conversation or a next-year conversation. I'm just glad you're on my radar." That's what keeps a "not right now" from becoming a dead lead.
Confirm the boring stuff before you hang up. Full name spelled out, legal company name, direct line, best email. Sounds trivial. You'll regret skipping it.
After the call
Same day, write it up from the recording, not from memory. Every field, including the ones marked not stated. Then send one short follow-up that thanks them, names what happens next, and asks for nothing.
No homework at the end of a first call. No forms, no document requests, no questionnaires.
You're building the right to a second conversation. That's all a first call ever is.