The business I own today started as one cold email to a stranger. No broker, no listing, no marketplace. In this post I will walk through exactly how that worked: the outreach numbers, the email itself, how the deal almost did not happen, how to tell a real seller from a tire-kicker, and the diligence metrics I would look at now that I could not see as a first-time buyer.
Context for the advice: I searched for about a year, bought System Six (an outsourced bookkeeping firm) through a self-funded SBA deal, and have run it since. Our firm now also keeps the books for dozens of other acquisition entrepreneurs, so I see how deals play out from both sides of the table.
The two channels: brokered listings and direct outreach
Every path to finding a business runs through one of two channels. Brokered listings (BizBuySell, broker networks, marketplaces) are real inventory with a process built in, but you are competing with every other buyer, and the broker runs the timeline. Direct outreach — what searchers call proprietary search — means building your own list of companies and emailing owners who are not (yet) selling.
I split my time: roughly 20 to 30 percent building broker relationships in my target geography, and the majority on direct outreach. The reason was not deal-flow math. It was trust:
I really felt like one of the most important things you can do is buy a business from a seller you have a ton of deep trust with. And the best way to build a lot of trust with a seller is to run more of your own process, versus going through a broker.
Chris Williams, Mundane Millionaires
Pick the industry first — you cannot change it later
Before any outreach, the highest-leverage decision is which industries you target. This became my North Star, and it is what I tell searchers now:
You’ve got to buy a business in a good industry, because you cannot change that. You may be able to buy the business from a bad seller and overcome that. But once you’re in an industry, you’re in it.
Chris Williams, Mundane Millionaires
Do real homework on a small number of industries before you send a single email. It focuses your list-building, and — as you will see below — it is also what makes your cold email land, because owners can smell a template from the subject line.
The cold email that found my business
Here is what my outreach actually looked like, with the numbers:
- Low volume, high touch: real, individually written emails — not thousands of templated sends per week. Roughly 80 percent reusable structure, 20 percent custom to that specific owner.
- A real hook: one line based on something specific — the owner’s LinkedIn, their business, their industry position.
- Credibility plus intent in two sentences: I have worked in finance; I want to buy a business in this industry because of the recurring revenue model — something that proves you know the industry.
- A direct ask: I would love to talk if you are ever interested in selling. No ‘I will cherish your legacy forever.’ As I put it on the podcast: just be a human.
It’s below a 10% response rate on the first email. If you do a good job of following up, I’ve heard of people getting it up to 20 or 30% over time.
Chris Williams, Mundane Millionaires
One honest confession: I never built a proper tech stack around my outreach, and I regret it. Take a week to set up your email tooling so you can track who to follow up with and when. But balance that against the opposite failure mode — spending six months building a system instead of sending emails. Do not wait for perfect.
Hang around the hoop: how the deal actually happened
The owner of System Six — Jeremy, an entrepreneur who had started the firm because he saw a good industry, not a CPA — responded to my cold email. When we first talked in November, he was not ready to sell. We stayed in touch.
Then his circumstances changed: a personal tragedy made him want more time with his family, other offers appeared, and he hired a broker to run a clean process. From LOI to close took 95 days.
You’ve got to hang around the hoop in search. If you get on the phone with a seller and have a decent conversation, just follow up every couple of months — because you might get lucky when circumstances change.
Chris Williams, Mundane Millionaires
Two honest notes on that story. First, luck is a real input; direct outreach just buys you more lottery tickets with better odds. Second, the 95-day close was only possible because the business had very clean books and no heavy assets or liabilities to diligence. Remember that detail — it is the difference between a 95-day close and a 9-month one.
How to tell a real seller from a tire-kicker
The most expensive failure mode in off-market search is spending months on someone who was never going to sell. The tells I trust:
- Meet the seller’s spouse, early. Take them both to dinner. Ask the spouse what they think about the business.
- Ask the retirement question: ‘What are you two going to do next?’ If neither has a real answer, they have not actually decided to sell — they are playing you for a number.
- Watch for process signals: a seller who engages advisors, produces documents promptly, and keeps momentum is real. One who stalls on every request is not.
They need to want to sell. If you think you’re going to get somebody off the street and convince them to sell their business, that’s pretty unlikely.
Chris Williams, Mundane Millionaires
What I would diligence now: unit economics a level deeper
As a first-time buyer I focused on the classics: revenue growth, EBITDA margins, client retention, average client size. All still matter. But three years of operating — and seeing the books of many acquired businesses — moved my diligence a level deeper:
It’s not revenue and margin numbers anymore, it’s a level deeper… average ticket size by customer, monthly recurring revenue per customer, and employee retention over certain periods of time… You can move some stuff around to make gross margin look better. Get to the fundamental unit economics of the business.
Chris Williams, Mundane Millionaires
Specifically, for any people-driven service business:
- Average ticket / MRR per customer, and its trend. Growing revenue by adding small clients and growing it by expanding ticket size are very different businesses. (In our own firm, moving average ticket from roughly $18K to $29K per year added 40-50% more revenue on the same number of new clients. [UPDATE: current figures.])
- Employee retention curves, not averages. Ask for tenure by employee. A business that loses people in the first six months but keeps them for years afterward has a hiring problem; one that loses tenured people has a culture problem. Only the second should scare you.
- Customer concentration and churn by cohort, not a single blended rate.
- Capital cushion: ‘It’s not just percentages and multiples — it’s how many dollars do I have to play with, and how forgiving will the lender be if things get hairy or I want to invest to grow.’ Do not structure an SBA deal so tight that one bad quarter forces bad decisions.
And on size: I am a believer in buying bigger when you can. An 18-person business can absorb a key departure; a 6-person business cannot. Things will happen.
Why clean books decide how fast you close
Every step of this playbook runs through the target’s financials. The cold email credibility, the valuation conversation, the LOI, the lender’s underwriting, the 95-day close — all of it moves at the speed of the seller’s books. I closed quickly because my seller’s books were clean. Many searchers are not that lucky: deals drag, retrade, or die because the numbers cannot be trusted.
This is now a meaningful part of what our firm does. We keep the books for dozens of search-acquired businesses — the hosts of the podcast this post is drawn from are clients themselves — representing a large portfolio of post-acquisition financials. [UPDATE: verify and use the current figure — cited as $180M+ of client revenue from search businesses on the episode.] If you are heading into diligence, get eyes on the target’s books early: what is clean, what is dressed up, and what will slow your close.
Buying a business? Get the target’s books reviewed before you close.
Frequently asked questions
How do I find businesses for sale?
Three channels: online marketplaces and brokered listings (BizBuySell and broker networks), building relationships with brokers in your target geography and industry, and direct outreach to owners who are not listed. Serious searchers run all three; the best deals often come from the third.
How do I find off-market businesses to buy?
Pick one or two industries, build a list of companies in your geography, and send personal, specific cold emails to owners. Expect under 10% response on the first email and follow up every couple of months. Off-market takes longer — plan a one-to-two-year runway.
What response rate should I expect from cold outreach to owners?
Below 10% on a first email, even when it is personal and well targeted. Disciplined follow-up over months can push cumulative response toward 20-30%. Volume templated blasts perform far worse — owners now receive them constantly and delete on sight.
What questions should I ask when buying a business?
Beyond the financials: Why are you selling, and what will you do next? Can I meet your spouse? What does employee tenure look like, person by person? What is your average ticket per customer and its trend? Who are your largest customers and what share of revenue are they?
How long does it take to buy a business?
Searching typically takes one to two years. Once under LOI, a clean deal can close in about 90 days — mine took 95 — but messy financials, financing friction, or an unprepared seller commonly stretch it to six months or more.
