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Contrarian Thinking

A Practical Framework for Thinking Bigger

May 23, 2025
4 min read
“Only those who will risk going too far can possibly find out how far one can go.”
TS Eliot

-T.S. Eliot

Meet Steven.

Codie Sanchez and Steven Montgomery

Steven runs one of the fastest-growing home service franchise groups in America — and we proudly own a piece of it.

He started with $12 in his bank account.

No trust fund, no pedigree, just a ridiculous work ethic… and one rule that most people would laugh at:

Every quarter, Steven has his team set goals that sound — and this is his word — ridiculous.

Not ambitious. Not “stretch.”

Ridiculous.

As he puts it:

I was once told that my goals were ridiculous. So I decided that every quarter we'd set ridiculous goals.

Why?

Because he understands something most owners never figure out:

Big Goals Create Gravity

We call it Goal Gravity — the force that pulls everything in your business toward the target.

The Goal-Gravity Principle

Small goals? Your org drifts.

Big goals? Priorities sharpen. People step up. Or get out of the way.

Even if you miss — and you probably will — you land somewhere you couldn’t have reached playing it small.

The Startup Crowd Gets This, Kind Of

There’s a lot of hate tossed around about startup culture. Some of it is fair…

Too many founders are playing milestone bingo, and too many investors are rewarding vibe or vanity over viability.

But let’s not pretend Silicon Valley doesn’t have something figured out. At their best, venture-backed startup builders are world-class at one thing:

Thinking bigger than the current reality.

We see it all the time.

Our venture fund backs founders trying to reshape entire industries. Some will win. Some won’t.

But if they’re not swinging big? We’re not writing a check.

On the other end, we invest in the small and sturdy, like Steven’s brands across window painting, roofing, garages, and more, and guess what we’ve learned?

The small, “boring” businesses that actually scale? Their owners are thinking BIG, too.

The real trap is often the scale of their thinking. But thinking big isn’t just a mindset.

It’s a choice you have to make, constantly.

So How Do You Expand That Mindset?

Every builder — whether they run a massive startup or a small service business — faces the same tradeoff, over and over:

Do I double down on what’s working?

Or try something that might break everything, but also might change everything?

That’s the quiet fork in the road most people never talk about. In more technical terms, it’s this:

  • Exploitation = Repeat what already works.
  • Exploration = Try what might work better.
KDnuggets

Both have utility. But here’s the catch:

Exploitation gets you efficiency. Exploration gets you breakthroughs.

And right now, almost everything — school, jobs, algorithms — nudges us toward being better exploiters:

  • Memorize the right answer.
  • Optimize for what’s worked before.
  • Don’t question the playbook.
  • Definitely don’t risk looking dumb.

Everything nudges you toward refining, not rethinking. That’s fine… Until you realize your whole business is built on habits you stopped questioning 3 years ago.

And right now? The world’s got a surplus of exploiters.

But There’s a Shift Happening

For a long time, it felt like only VCs and startup founders were allowed to think big. But that monopoly on ambition? It’s breaking.

We’re seeing a new kind of builder rise up. Owners of small businesses asking big questions:

“Why not us?”

“Why not set some goals that scare the room a little?”

Steven did. Now he’s scaling to hundreds of locations across America.

The world needs more small businesses, but it doesn’t need more small thinkers.

It needs more owners like these, with gravitational pull.

Contrarian Community

PS. If You’re One of Those Owners…

You might like this thing we’re doing in Miami, June 27-29.

It’s our growth accelerator workshop for a small group of serious operators looking to scale smarter, systemize, and stop doing everything themselves.

It’s confidential. Operator-led. Zero fluff. Think: playbooks, bottleneck breakdowns, 1:1 time with Codie’s team, and a custom 90-day scale plan built around your business.

If that sounds useful, learn more here.

If not, you know the drill — just keep being ridiculous.

Team Contrarian
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DOPAMINE HIT

The information contained here is educational, may not be typical, and does not guarantee returns. Background, education, effort, and application will affect your experience and the profitability of any business. Individual results may vary.

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