Since the first acquisition I made in 2015, I’ve acquired over 40 businesses. Some of these are small content businesses, some are multi-million dollar agencies or direct response courses. Some of those acquisitions have been excellent. A couple have been painful. Most have been somewhere in between.
If I were starting over today, knowing what I know now, I’d do a lot of things differently. Not because we made catastrophic errors, but because the small decisions in the first deal set patterns that compound across every deal after it.
This isn’t a “top 10 tips” post. These are the specific things I wish someone had told me before my first acquisition, from someone who learned them by doing.
I would spend more time with the operator before closing
Every broker will tell you the financials matter most. They’re right, but they’re also selling you a transaction, not an outcome.
The single biggest risk in buying a small business isn’t the revenue declining or the market shifting. It’s the operator leaving and nobody being able to replace what they did.
I’ve seen businesses where the P&L looked bulletproof, the growth was real, and the margins were healthy. Then the founder left and within six months, the business was unrecognizable. Not because they took clients with them or sabotaged anything. Because they were making dozens of micro-decisions every week that kept everything running, and nobody documented any of it.
The difficult part is most founders downplay this role. Sometimes intentionally, mostly just because they don’t realize it is happening.
“I spend 4 hours a week running this business”.
Actually, you spend 4 hours running it, 15 hours thinking about it, and a new buyer would need to spend 40 just trying to keep up.
Now, before closing any deal, I want to understand exactly what the operator does every day. Not what they say they do in a two-hour call. What they actually do. The meetings they take, the fires they put out, the relationships they maintain, the decisions they make that nobody else sees.
If you can’t clearly see how the business runs without the current owner, you’re not buying a business. You’re buying a job.
I would not trust “Years of consistent revenue”
This is one of the most dangerous phrases in small business M&A.
A business that’s done $500K a year for four straight years looks stable. Brokers will pitch it as “proven and consistent.” The multiple reflects that stability.
But consistency in the past doesn’t predict durability in the future. What kept that business at $500K? Was it a founder grinding every day? A single marketing channel that could disappear overnight? A client base that’s quietly concentrating?
I’ve bought businesses with excellent historical consistency that started declining the moment market conditions shifted. The consistency wasn’t structural. It was the owner paddling hard enough to keep the boat steady.
Now I care more about what’s driving the revenue than how long it’s been there. I want to see where customers come from, how diversified the acquisition channels are, and what happens if you remove the owner from the marketing and sales process.
A business with two years of revenue from five different acquisition channels is more durable than a business with five years of revenue from one channel.
I would negotiate structure harder than price
First-time buyers obsess over the purchase price. I did too. “Is 3x too much? Should I push for 2.5x?”
The price matters, but it’s often the least interesting part of the deal.
What matters more is how you pay it. A $500K business at 3x ($1.5M) paid entirely in cash is a completely different risk profile than the same deal at 3.5x ($1.75M) with a seller note covering 40% and an earnout on the remaining 20%.
In the second scenario, you paid a higher multiple but put up less cash, kept the seller incentivized through the transition, and created a mechanism to adjust if the business underperforms. That’s a better deal despite the higher headline number.
We’ve used seller notes, earnouts, equity, and various combinations across our deals. Most of our acquisitions were cash-heavy, but the three we did with zero cash down would never have happened without creative structuring. And even on the cash deals, the non-cash components (earnouts, seller notes, transition terms) shaped the risk profile more than the price did.
If you’re capital-constrained (and most first-time buyers are), learning deal structuring is worth more than learning how to negotiate price.
I would be more honest about what I don’t know
There’s a temptation when you’re acquiring a business to project confidence. You want the seller to trust you. You want to feel like you know what you’re doing.
But the most expensive mistakes I’ve made came from not asking enough questions. Not because I didn’t care, but because I didn’t want to look inexperienced.
The seller knows more about their business than you ever will during diligence. They know which clients are thinking about leaving. They know which employees are unhappy. They know which revenue lines are softer than they look. They’ll often tell you, if you create space for honesty.
The best diligence conversations I’ve had started with some version of: “I’m going to ask you a lot of questions that might seem basic. That’s because I want to understand this as well as you do, not just well enough to sign.”
First-time buyers: you are allowed to ask questions that feel dumb. The people selling you a business expect it. The ones who get impatient with your questions are often the ones you should be most careful with.
I would plan for integration before I close
Most acquisition guides end at the close. Congratulations, you bought a business. Here’s the keys.
Nobody tells you what happens on day 31.
The first 100 days after closing determine whether the acquisition works. Not the diligence, not the LOI, not the price. The integration.
What systems are you putting in place? Who’s running what? How are you communicating with the existing team? When do you start making changes, and which changes should wait?
I’ve learned that the worst thing you can do is change everything immediately. The second worst thing is change nothing. The right answer is somewhere in between, and it depends entirely on the specific business.
Now we have a post-acquisition playbook. It covers the first week, the first month, and the first quarter. Different businesses need different approaches, but having a framework means you’re not figuring it out from scratch every time.
There’s a famous line from World War II: no plan survives contact with the enemy. Hopefully your brand new acquisition doesn’t turn out to be the enemy, but the principle holds. No post-acquisition plan survives contact with the actual business. You should absolutely make the best plan you can, and then be prepared for most of it to go sideways once you’re operating the thing.
But having a plan that goes sideways is still better than having no plan at all. If you’re about to close your first deal and you haven’t thought about what happens after, you’re not ready to close.
I would find people who’ve done it before
Buying a business is one of the loneliest decisions you can make. Your friends don’t understand it. Your family thinks you’re crazy. Your accountant is nervous.
The acquisition entrepreneur community has grown significantly in the past few years. There are people who’ve bought one business, five businesses, twenty businesses. They’ve made the mistakes you’re about to make.
Finding even two or three people who’ve been through it, who you can call when a deal gets complicated or a post-acquisition problem blindsides you, is worth more than any course or template.
I spent too long figuring things out alone. The best decisions I’ve made in the last two years came from conversations with people who’d already solved the same problem.
The honest summary
Buying a business is one of the best wealth-building strategies available to people who are willing to do the work. But the work isn’t just finding a deal and closing it. It’s understanding what makes businesses actually durable, structuring deals that protect you, planning for what happens after close, and being honest about what you don’t know.
If I were starting my first acquisition today, I’d spend less time on spreadsheets and more time understanding the humans running the business. I’d spend less time negotiating price and more time negotiating structure. And I’d find people who’d done it before and ask them every question I had.
The good news is it’s never been easier to start. There are more resources, more deal flow, and more people willing to help than at any point in history. The barrier isn’t information. It’s action.
If this was useful to you, it would probably be useful to someone you know. Feel free to share it or forward it to a friend. One of the hardest things about being a small public company is simply being discovered, and word of mouth goes further than anything else.
This post reflects my personal views and experiences. It is not investment advice. For the most current information about Onfolio Holdings, refer to our SEC filings at sec.gov.