Acquisition advice for a risk-averse family man

Your W2 job isn’t as safe as you think.

Feb 11, 2025
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Ben Kelly

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A curious commenter on one of my Instagram stories asks:

“How does a risk-averse person with a growing family start doing acquisitions?”

I’m glad this question came up, because I know a lot of people are in this situation... and because as a father of four, this is exactly where I was when I started.

But before I explain the “how,” I want to address that word — “risk-averse.”

Avoiding unnecessary risk is smart. But most people have a skewed idea of what’s actually risky and what’s not.

Everything in life that gives an extraordinary outcome will have risk.

Achieving financial freedom for your family is an extraordinary outcome. And that means you’ll need to take extraordinary actions, doing things that other people aren’t willing to.

So the question shouldn’t be “what can I do to avoid risk entirely?”

Rather, it should be:

“What do I want my financial future to look like? And what amount of risk am I willing to take on to get there?”

Not to mention, if your goal is to achieve financial freedom, then relying solely on a W2 salaried job is already a risky decision.

You can get laid off or fired at any moment. It happens to good employees all the time, even at prestigious companies. There’s no true security there. And, scaling your income quickly is extremely difficult.

Back to the “how”:

I am not advocating for dumping your life’s savings into a hail-mary business deal to try and get rich quick. That’s called gambling. What I do recommend is treating business-buying as a slow, long-term financial and career investment.

The key to making this work is:

You do not need to quit your day job!

It’s totally possible to do your first acquisition in your spare time, and only leave your 9-5 once your new business is turning a steady profit.

This is exactly what I did. In fact, I worked at JP Morgan full-time all the way through my first two acquisitions before quitting.

So if you’re brand new to the acquisition game, here’s what I recommend for first steps, even if you have kids:

Read books (especially Buy Then Build by Walker Deibel), watch YouTube videos (I show you all the basics you need to know on my channel), and learn everything you can from free resources online.

It’s the same as mastery of any other skill — it just takes repetition plus time. If you have a growing family, it’ll simply be more difficult. But it is doable.

The important thing is to pick a direction and get started.

With that in mind...

If you’re interested in buying a small business in the near future:

Tell me more about your goals in this quick survey here, and you’ll be the first to know if I come across deals that match your budget.

Or, if you want to sell your business and want to find qualified buyers, let me know here.

Catch you in the next issue,

— Ben Kelly