Today in 5 minutes or less:

✔️ The #1 Way to Stay Stuck (Don’t Do This)

✔️ 8 Ways to Protect Your Downside

✔️ 1 Thing No One Wants to Admit

The #1 Way to Stay Stuck (Don’t Do This)

If you’re looking for a rock-solid plan to stay stuck in 2025 — financially, emotionally, professionally — here it is:

Step 1: Don’t Take Any Risks

• Do the minimum
• Collect the paycheck
• Let someone else decide your trajectory

Plenty of people build real wealth and ownership inside their day job:

• They negotiate equity
• They invest their earnings
• They build skills and launch projects that make them indispensable

They own their role.

But if you’re clocking in and out, never asking for more, never raising your hand, and never seeing your job as an opportunity to build?

Then you’re not working — you’re waiting. Waiting for someone else to notice you. Waiting for “one day” when you’ll take the lead. And “one day” is the most expensive day on the calendar.

Step 2: Take Risks You Barely Understand

Ambition without reason? Turns out, that’s delusion:

• You buy a business you’ve never seen.
• You jump at an investment you can’t explain.
• You take on a project without devising a strategy
• You leap, but you don’t know where you’ll land.

Recklessness doesn’t make you bold. It makes you broke.

The Formula You Should Follow

Take calculated risks. Smart risks. Risks you’ve:

• Studied
• Questioned
• Prepared for

Here’s the thing: Ownership requires risk, but smart risk requires understanding.

The guy who digs into the books, learns the trade, buys a landscaping business, and locks in 3 HOA contracts? Smart risk.

The guy who buys a food truck because “it sounds fun” without knowing the first thing about a balance sheet? A recipe for drowning in debt.

So, if ownership is the game and risk is the ticket, the real question becomes:

How do you make sure the risk doesn’t knock you the f*ck out?

8 Ways to Protect Your Downside

You can never remove risk entirely. All you can do with it is:

• Take it
• Mitigate it

But the best deal is a bad deal avoided. So here are 8 quick tips on mitigating risks in dealmaking + spotting a deal you should avoid…

1. Simplicity = Green Flag

Dealmaking can get incredibly complex. Smart buyers:

• Ask simple questions.
• Find simple answers.
• Don’t give into the temptation to over-complicate.

Smart buyers know:

• Hope is not a business strategy
• You pay for current profits, not potentials
• Growth is a potential, not a guarantee

We go by numbers, not feelings.

2. The Employee Exodus

A unique risk in acquisitions:

Key employees walking out the door — taking clients, knowledge, and revenue with them.

Some buyers learn too late that the entire value of a biz can walk out with the staff. Smart buyers price in human risk.

Get an understanding of key employees & the intangible value they add. Then set in place incentives to keep around those people you need. Here are a few ways to structure that:

3. Equipment Failure

In asset-heavy businesses, outdated equipment isn't just an expense. It's an existential threat.

Every piece of machinery has a replacement date. Ignore at your peril. Manage this risk by:

• Factoring equipment conditions into the purchase price
• Having backup suppliers ready
• Building replacement reserves
• Mapping out upgrade cycles

The tech cliff isn’t a matter of if but when. Plan for it.

4. Customer Concentration

A deadly trap?

When 1 client represents 15%+ of revenue. That's not a business, that’s a hostage situation. And you’re the hostage.

Imagine you’ve just bought a biz that served the same client for 20+ years. A new CEO joins the client company.

1 meeting. 1 decision. For whatever reason, you’re gone.

A business with 1 big client can be a great foundation — but it’s only stable if you’re building on it, not leaning on it.

5. The Working Capital Trap

Many buyers will see profits but look past the liquid cash needed to operate and grow.

Working capital needs can sink you. Always keep these in mind:

• Growth requirements
• Payroll obligations
• Inventory costs

Most buyers forget: Growth and operations can eat cash faster than profit feeds it.

6. Regulation Risk

Every business faces regulatory risk. One legal change can set back years work.

I’ve seen entire niche industries crumble because owners didn’t see a legislative storm coming.

The best protection for smart buyers:

Where you can, don’t put all your eggs in one basket.

Diversify your revenue stream with satellites. And keep your strategy ahead of compliance.

One signature shouldn’t be able to end your business.

7. The Systems Nightmare

A common red flag in boomer biz’s:

You take over operations, just to realize everything was in the old owner’s head. No systems, no manuals… just chaos.

Sure, the financials look great, but if the whole operation falls apart the second the owner retires to Florida? Congrats, you just bought a dumpster fire with decent margins.

A business with excellent financials but no SOPs can make you regret your buy. Smart buyers price in systems.

If the business can’t run without the previous owner, that’s a discount tag on the purchase price.

(Let this be a warning to anyone out there trying to sell a business…)

8. The Life-Fit Trap

The worst rookie mistake in business buying?

Forgetting that you actually have to live with the thing you buy.

Sure, that septic tank cleaning company might cash-flow nicely, but if you’re the one scrubbing sh*t and quickly realize it’s not for you… Well, good luck.

Smart buyers know the drill. 5 things to outline before your search:

• What do you obsess over?
• What size of business is right for you?
• How much can you realistically afford?
• How much does the business need to pay you to sleep at night?
• Where you uniquely have the best likelihood to succeed?

The wrong business won’t just cost you money. It will own you, not the other way around.

1 Thing No One Wants to Admit

Avoiding risk is increasingly a privilege of a world that no longer exists.

Inflation is mugging you every time you buy groceries, AI is sharpening its knives for your job, and “job security” might as well be a punchline at this point.

In 2025, your only risk greater than taking one will be avoiding risk entirely. Don’t let this be you:

So the key isn’t to avoid risk — it’s to take smarter risk.

The longer you wait, the bigger the bill.

Your Next Move Starts HERE

Tired of sitting on the sidelines? The Contrarian Community is where serious minds go take smarter action, scale faster, and build ownership with confidence.

Inside, you’ll access expert guidance, proven strategies, and a network of ambitious dealmakers to help you buy and scale Main Street businesses.

Click here to talk to our team now.

1 Last (Big) Thing...

Our friend Chris Voss, former lead FBI hostage negotiator and bestselling author of Never Split the Difference, is headlining his first-ever Negotiation Mastery Summit. Two days. Life-changing strategies. The tools you need to own every negotiation. Dont miss out.

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