Founder | Investor | Author of #BuyThenBuild Helping entrepreneurs buy businesses and build wealth through acquisition and private investing.
St Louis, MO
Joined July 2011
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Most entrepreneurs are playing a rigged game.
96% of businesses never reach $1M in revenue.
75% of VC-backed startups go completely to zero.
Yet we keep following the same playbook.
After buying 7 companies in 10 years, I discovered why: ⬇️
One question I think every business owner should ask before selling: could the business run without you?
I’ve seen how easy it is to get stuck in operator mode.
You buy a business to build wealth, but suddenly, you’re the one keeping everything moving.
I call this the Operator’s Dilemma. My goal is to build a business so I can step back and focus on allocating capital again.
In this week’s #WealthStackWeekly, I’m sharing a 3-step audit to help you start making that shift before year-end.
Get this week’s issue for free!
wealthstackweekly.com
I knew @sbabmarks was next level. I didn’t know he was specifically Level 3542!
And he just hangs out in the back row like no big deal!
You could fund the first 3 investments upfront, borrow against a portfolio, or build gradually.
The catch: Returns aren’t guaranteed. Deals can lose money, take longer than expected, or fail to return your capital. Future opportunities aren’t guaranteed either.
The goal is to make your capital work more than once, but the risks matter just as much as the math.
A business can look profitable on paper and still be a nightmare to run.
Take the one that made 108% of its annual earnings in December. The other 11 months? It lost money.
When buying a business, you're not just buying profits. You're buying its problems, too.
That’s why a higher multiple can make sense when the hard work of reducing risk is already done.
The SEC just put forward a major proposal for private market investing.
But will it actually create better opportunities for investors?
New rules can change the landscape, but what does that mean when you're trying to get into a deal?
This week’s #WealthStackWeekly breaks it down.
👇 Subscribe for free:
wealthstackweekly.com
You can spend 10 hours solving problems and still make zero progress on the questions that actually matter.
I had a day full of unexpected tax issues and transaction decisions. Everything needed an answer, so everything else got pushed aside.
The problem? Strategic thinking doesn’t come with a deadline attached.
Make time to ask yourself: Where are we going? What am I missing? What needs to happen next?
Otherwise, those questions might show up at 3 a.m.
I bought a “boring” business over a decade ago.
It became the cash cow everyone talks about today: six figures a year, debt-free, manager-run, and barely any of my time.
So why am I even considering selling it?
Because a great asset can stop being the right asset for you.
After 10+ years, I’ve seen how much has to go right for truly absentee ownership to work. The right business. The right manager. The right level of oversight.
And now my manager is approaching retirement.
Nothing is changing tomorrow, but it made me think about the risk that still sits with the owner when the person running the business leaves.
Then there’s opportunity cost.
My portfolio looks very different from what it did 10 years ago. What made perfect sense to own back then may not be the best use of my capital today.
I haven’t decided whether I’ll sell.
But it’s a useful reminder:
“Good business” and “good business for me to own” are two very different questions.
$105B for AI compute is a HUGE signal.
But I keep thinking about what happened during the telecom boom.
Nortel’s revenue fell 62%.
Equinix later grew 22x.
When an infrastructure cycle gets this big, the obvious winner isn’t always the one that captures the most value.
This week’s #WealthStackWeekly breaks down where AI’s value could actually settle.
Subscribe + get it in your inbox.
wealthstackweekly.com
Funny how an investment thesis can look completely wrong… until the market catches up.
In 2017, Will was talking to me about machine learning and engineers who understood the industries they were building for.
Then ChatGPT hit.
Codesmith got crushed. I voted for a ~$60M acquisition. Will passed.
Now AI has created a different problem: companies need people who can actually deploy it.
Codesmith just secured a $100M+ BPA with the U.S. Treasury to help hire, train, and deploy AI engineers.
11 years in, I’m very interested in what comes next.
Comment “AI,” and I’ll send you the full presentation + Deal Room.
One of the biggest mistakes in acquisitions?
Waiting until you have all the answers before making an offer.
I’m usually looking for 60–70% clarity:
What happens when the biggest problem in AI is no longer building the AI?
That’s the shift happening right now.
I watched one company go from $18.5M to $5M in 18 months, then become incredibly well positioned for this next phase of AI.
The constraint has changed:
Models → compute → deployment.
Now the question is whether companies can actually make AI work inside real businesses.
In today's #WealthStackWeekly, we’re digging into where the AI money could go next and why deployment may be the next major battleground.
Link below 🔽
wealthstackweekly.com/p/ai-m…
I keep coming back to this question:
What if you didn’t need to keep adding money to your investment portfolio to create income?
Say you put $450K into a deal targeting a 2x return over ~3 years.
If it works, you could take the $450K gain as income and roll the original $450K into the next deal.
Then repeat.
Nothing humbles you faster than sending an email with {first.name} still sitting in it. 😂
We definitely heard about it.
But after we apologized and fixed it, something surprised me: we got way more replies than usual, and most were incredibly kind.
It made me realize how easy it is to notice the criticism and miss the people quietly rooting for you.
Sometimes, you don’t see the community you’ve built until you give them a reason to show up.
Most people see an IPO as the beginning.
I see it as a potential exit.
The interesting part can happen long before a company hits the public markets.
I break down why in this week’s #WealthStackWeekly
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