My Next Big Bet

Why I’m Going All In on Small Business Acquisitions

In partnership with

This Week at a Glance:

  • Why should you consider small businesses?

  • What should your first acquisition look like?

  • How can you pay for it without going broke?

Why I’m Buying Small Businesses

Small businesses…get it? I crack myself up.

I’ve been pretty successful in the public equities market.

My edge came from focusing on long-term outcomes and keeping emotional control — that’s how I found underpriced equities and squeezed return out of them.

Now I’m shifting my focus to buying small private businesses.

Why? Because it’s a far less efficient market.

You can’t buy a great local business on Robinhood. That means I’m not competing with day traders or get-rich-quick gamblers.

Private businesses also offer more direct control. When I buy one, I can improve operations, implement better systems, and directly influence outcomes — something no public stock gives you.

And they’re harder to find. When most people think of buying a business, they think of BizBuySell or Flippa — but ~90% of businesses will never be listed publicly.
If you’re willing to put in the work to source deals, build trust with owners, and operate the business well — there’s incredible opportunity.

That’s my thought process and why I’m on my mission.

Thanks for joining me.

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What Business Am I Looking For?

Gotta be diligent with your due diligence.

If I were a pro, I’d know exactly what business I want to buy.

I’d have a tight buy box, a list of targets, and I’d be making phone calls every day until I found the right deal.

But here’s the reality: I’m operating way outside my comfort zone.

If someone handed me a machine shop free and clear tomorrow, sure — I could figure out how to run it. But it would be a steep learning curve — and a very painful one.

While I could do it, that’s not the kind of risk I want to take on my first acquisition.

To properly de-risk my investment, my first business needs to be something I can understand — and ideally something that plays to my strengths.

That’s the filter I’m using right now:
Understandable economics
Simple operations
Not wildly outside my experience base

The goal is to build a solid first win — and from there, I can take bigger swings.

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How Can I Afford to Buy a Business?

How to get creative financially.

Buying a business isn’t like buying a stock — you don’t just click “buy” and own it. You have to structure the deal.

And to make matters more complicated, they aren’t cheap. The business I’m looking for is likely going to be a minimum of $1M.

That’s a lot to handle, so here’s how I’m thinking about it:

1️⃣ Seller Financing
Many small business owners are open to carrying a note — meaning they’ll finance part of the purchase price over time. It’s often a win-win: they pay less taxes and I get more flexible terms.

2️⃣ Small Business Loans
There are lenders — including SBA lenders — who specialize in financing small business acquisitions. Leveraging a smart amount of debt is one way to amplify returns, while still being prudent.

3️⃣ Outside Investors (LPs)
For the right deal, I may bring in outside investors to co-invest alongside me. That could mean raising a small equity check to close a deal that’s too big to do solo — or partnering on larger opportunities down the road.

If you’re an accredited investor and you’d like to see the kinds of deals I pursue — or potentially invest alongside me — you can apply to join my private investor list here.

For my first acquisition, I’ll probably use a combination of the first two. As I continue to scale, I’d like to leverage all three.