When people start thinking about buying a business, they go looking for information everywhere.

Some of it’s solid. A lot of it isn’t.

The truth is, the best lessons don’t come from gurus or Twitter threads. They come from people who’ve actually been in the arena – buyers who’ve searched, negotiated, closed, and lived through the first 90 days of ownership.

Or put in a different way, they come from the members of the Acquisition Lab.

Recently, my co-founder Chelsea Wood hosted a live panel with two members who’ve closed deals and are now on the other side of the search. These are real stories from real buyers – how they weighed buying big versus starting small, the challenges they faced, and the lessons they’d pass on.

Chelsea has guided hundreds of buyers through the emotional and practical realities of acquisition entrepreneurship, and her perspective – along with the insights she draws out from members – is incredibly valuable.

If you’ve ever attended one of my Office Hours, you know I work hard to make them practical and tangible. My goal is always to give you insights you can actually use in your own search – not just theory.

For this session, I wanted to try something new.

Instead of me telling you what matters, I wanted you to hear directly from people who were exactly where you are now – searching, making trade-offs, dealing with uncertainty – and who ultimately closed on a business.

So we put together a panel with two recent buyers:

• David Bregman, who shifted from wanting to buy big to realizing a smaller deal was the right fit.
• Brian Hartman, who not only bought his first business but has already moved into growth through acquisition.

 

Their stories reveal some of the biggest questions buyers wrestle with:

Should I buy big or start small? When is the right time to do a second deal? How do you balance risk, family, and freedom with the reality that business ownership is hard work?

Along the way, I’ll also share a third story from another member who couldn’t attend but wanted their experience highlighted – because it underscores an important lesson about aligning the type of business you buy with who you are.

 

Starting Big – or Starting Smart

We’ll start with David Bregman, who lives in Southern California and spent three decades in tech.

 

 

Like many of you, he hadn’t planned on leaving that world anytime soon. Then a layoff upended everything.

Instead of jumping back into tech, David started asking harder questions:

What do I want next? Do I even want another W-2 job? 

The answer was no.

That’s what led him to acquisition entrepreneurship – and eventually to the Lab.

At first, David was looking for a business with $3–4 million in revenue and upwards of $1 million in SDE. His logic was sound: if you want autonomy and wealth creation, why not go big?

But as he got deeper into the search, he realized something else: the bigger the business, the bigger the loan, and the more stress that came with it.

“I didn’t want to bet the farm,” he told us. “I wanted a business that could grow, but not one that was going to keep me up at night worried about a $500,000 SBA loan payment.”

So David pivoted. He focused on finding a company that was big enough to provide stability but small enough that the downside wouldn’t crush him. The result? He acquired Third Wheel Podcast Studio, with three locations in Los Angeles and Seattle.

 

 

The best part? It tied back to his early career in radio and television. “I didn’t buy it for that reason,” David said. “But when I stepped into the studio, it felt like coming home.”

The impact was immediate – not just on his balance sheet but on his quality of life. A college friend told him recently, “You sound happier than you have in years.”

His biggest takeaway for other buyers: There’s no right answer between big and small. The right answer is what lets you sleep at night.

 

Growing Through Acquisition

Next up was Brian Hartman, who joined the Lab in Cohort 11 – back when we were just getting started.

 

 

Like David, Brian had spent years growing businesses for other people. But after watching one of those companies exit, he made a promise: Next time, I’m doing this for myself.

That decision led him to buy Northside Tree Professionals in Atlanta, Georgia, in 2022. Unlike David, Brian bought in an industry he knew cold – one he’d been in since he was 22. That experience gave him confidence, but it didn’t eliminate the challenges.

His first 90 days as an owner went relatively smoothly – strong cash flow, happy employees, a supportive team. But six months later, growth nearly crushed him.

“We doubled revenue in our first year,” Brian said. “But our accounts receivable ballooned from $53,000 to over $500,000. The bank account didn’t look profitable even though the business was.”

The culprit was working capital. Commercial clients paid net-60 or net-90, while payroll and equipment costs hit immediately. For a new owner with fresh SBA debt, that mismatch is brutal.

Brian’s solution was to pause business development temporarily, lean harder into residential work (which paid faster), and inject additional capital into the company. Painful in the moment – but ultimately the right call.

That discipline paid off. By 2024, Northside Tree Professionals was thriving.

 

 

And just recently, Brian closed on a second acquisition in Dallas, Texas – a near carbon copy of his first business.

His lesson for other buyers: Don’t rush to build a Holdco. Start with one. Prove you can run it. Then add when the business – and your team – can handle it.

 

When Fit Matters More Than Numbers

The third story came from another member who couldn’t join live. On paper, their deal was a unicorn: closed within two years, strong growth, solid financials. But in practice, they were miserable.

Why? Two reasons.

First, they bought a business with only one key employee and a set of contractors. Coming from a corporate background with large teams, the isolation was crushing.

Second, the business was purely commercial B2B. It generated cash, but it didn’t generate meaning. There was no connection between the owner’s personal values and the day-to-day work.

They don’t consider it a mistake – the company is thriving, and financially, it was the right move. But the lesson they wanted others to hear was this: don’t underestimate cultural fit. It’s not enough to buy a profitable business. You have to buy a business that fits you.

 

What It All Means

Looking across these three stories, some clear themes emerge:

• Risk Tolerance Matters. Buying big isn’t always better. The right size is the one you can manage without losing sleep.
• Team Is Everything. Whether it’s Brian’s production managers or David’s studio staff, the people you inherit will make or break your success.
• Skills Transfer. Management experience, delegation, and communication are non-negotiable. You can’t learn them on the fly while protecting historical performance with a personally guaranteed loan.
• Fit Fuels Fulfillment. If you hate the work or feel disconnected from it, no amount of SDE will make you happy.

At the Lab, we say this all the time: the goal isn’t just to buy a business. It’s to buy the right business for you – and to do it in a way that doesn’t put your family, your health, or your sanity at risk.

 

Final Thoughts

The stories David and Brian shared – and the third member’s experience – remind us that acquisition entrepreneurship isn’t just financial. It’s deeply personal.

For some, the right path is buying big. For others, it’s buying small. For everyone, it requires honest self-reflection, discipline, and the willingness to put in the work.

As one member put it: “Sales won’t kill you. Terms will.” But I’d add this: the wrong fit will too.

At the end of the day, success isn’t defined by EBITDA multiples or transaction size. It’s defined by whether the business you buy helps you build the life you actually want.

Ready to acquire a business in the next 12 months? The Acquisition Lab is your first stop. Reach out to us today and get on the fast track to becoming an acquisition entrepreneur.