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Contrarian Thinking

You Need a Bobby

May 30, 2025
3 min read
“A small team of A+ players can run circles around a giant team of B and C players.”
Steve Jobs black and white photo

-Steve Jobs

Everyone wants a business that runs like a machine.

High-performing team. Fast-moving org. People who just get sh*t done.

So what do most builders do to foster this?

They take the MBA-approved route:

  • Write “core values” no one remembers
  • Host offsites where Tim from finance gets blackout on margs
  • Slap “Excellence. Integrity. Teamwork. Family.” on the wall
A black-and-white cartoon of a man sitting at a desk, staring at a sign that says “WE ARE A FAMILY.” His thought bubble reads, “People actually believe this shit?”—a satirical take on corporate culture slogans.

We’ve all heard the line: “Culture starts at the top.”

Cool, then explain why your team acts nothing like you.

Here’s the real reason:

Culture doesn’t drip down. It radiates out.

It spreads like a cold — person to person, desk to desk.

It’s the people sitting 3 seats over.

The ones employees text when you know what hits the fan.

The ones they see online at 8pm and think, “Damn, I guess we’re still going.”

That’s who drives the tempo.

That’s who sets the tone.

You know the person.

That’s your Bobby.

Our Bobby runs BizScout, our platform for buying and selling small businesses.

The man is a Swiss Army knife with caffeine for blood.

A boxing scene showing "Bobby" dodging a punch from "The Competition." Labels point to each person, symbolizing Bobby outmaneuvering competitors with agility and skill.

But (literally) kicking ass isn’t what makes Bobby special.

This is:

When we interviewed Bobby, we thought we were vetting him.

Nope.

He was vetting us.

“How big do you think this company’s going to get, and why?”

“What’s your 10-year vision?”

“What’s the worst thing someone who’s partnered with you would say about you?”

“When’s the last time you fired someone for underperformance?”

“What will you do if this company runs out of cash?”

He even asked about our summer plans. (Still not quite sure why…)

Point is, finding someone like Bobby is an absolute cheat code for business builders.

The moment Bobby showed up, things moved. Not because we told him to. Not because he had a fancy title. But because he operates like the business has his name on it.

(He’s also going to hate this. He prefers to build, not be talked about…)

We call that The Bobby Mindset.

And once you see the difference, you can’t unsee it.

A comparison table with two columns: “Employee Mindset” and “Bobby Mindset.” The chart contrasts passive employee behaviors (e.g., waits to be asked, avoids feedback) with proactive traits attributed to Bobby (e.g., acts before being asked, builds systems).
It works like dominoes…

The people around Bobby start to level up.

Momentum spreads.

Then the whole org starts to move.

Urgency kicks in. Systems sharpen.

Ownership becomes the norm. The business hums.

It’s how BizScout managed to go from a napkin sketch to 56,000 listings and 21,000 buyer-broker connections. And starting soon, BizScout will have exclusive deals that can only be found there.

Real Talk

A builder’s biggest competitive edge isn’t AI or distribution or even capital.

It’s whether or not they have a Bobby on their team.

So here’s the play:

Go find your Bobby.

And if you already have one?

Get out of their way.

Team Contrarian
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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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