Corporate America Was Crushing His Soul . . . So He Quit and Created UNTUCKit

Here at Notes to an Entrepreneur, we are experimenting with stories less about famous entrepreneurs and more about famous brands and the less-well-known (but maybe more relatable) entrepreneurs who started them.

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Chris Riccobono was doing well on paper.

He had an MBA. A stable job in corporate America doing medical sales. He made good money. He was safe, stable, secure.

And bored silly.

The job felt soul-crushing. He spent his days in khakis and stiff, boxy shirts, sweating through client meetings and dreaming of doing something, anything, he actually cared about.

One day, he noticed something small that really bugged him:

He was supposed to wear his shirt tucked in, but on those occasions he didn’t, he looked… sloppy. Not just casual. Messy. The shirts were too long, the tails flapped awkwardly, and he felt like a kid playing dress-up.

So he googled it.

Nothing.

There was no brand that made shirts designed to be worn untucked. Which, he thought, was stupid. Men had started dressing this way, more casually, more and more at work but no one had built a business around that idea.

That was the spark.

Turning it Around

Chris decided this was his moment, his chance, his big idea.

So he started to save his money. He also started taking fashion design classes at night.

People around Chris thought him nuts. “You’re not a designer,” they said. “You don’t even know how to sew.” True.

Factories did not want to work with him. Friends told him no one would pay premium prices for untucked casual shirts.

But he kept going.

Entrepreneur, he.

The Big Payoff

Cheris found a partner (Aaron Sanandres), they pooled their savings, and launched UNTUCKit in 2011. They sold direct-to-consumer at first, online only, with one style, and a lot of praying.

The early reviews came in: Men loved it.

After much trial nd error, they had hit upon a style of shirt that was just the right length and fit. Not sloppy. Not tight. Designed to look good untucked.

The real tipping point came when they began opening retail stores (a bold move for an online brand), and then scored media features and celebrity placements.

Word spread. Investors came knocking, the world suddenly went untucked.

For Chris, and millions others, the Untuckit life sure beat the corporate one.

The Takeaway

Your “dumb” idea, that one you think is too obvious or too small, might be your ‘get out of jail free’ card. Chris did not invent shirts. He just paid attention to a specific, common frustration. Then he solved that problem really well.

That is entrepreneurship in a nutshell.

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Steal This Strategy!

📖 Book – Shoe Dog by Phil Knight
A gritty, honest account of building a clothing line from nothing, but with plenty of soul and struggle.

🎥 Video – How UNTUCKit Built a $200M Brand
A short interview with the founders explaining their journey and decision to bootstrap.

🌐 Website – UNTUCKit.com
Great example of a simple product, clear brand story, and smart positioning.

🛠️ Tool – KickoffLabs
Run a viral waitlist or product launch the way UNTUCKit did to build early momentum.

About Steve

Steve Strauss is the best-selling author of The Small Business Bible (and 17 other books), Inc.’s small business columnist, a lawyer (non-practicing), and an entrepreneur. He sold his last venture, TheSelfEmployed.com to Mark Cuban & Zen Business. Need a ghostwriter or a newsletter for your business? Contact Steve!