If We Really Loved Cinderella Stories, We’d Invest in Cinderellas

It’s March. Ok, now it’s April. But it’s not called April Madness…

I started this post when the Hogs were still alive and I didn’t send it because, while I am not superstitious, I’m a little stitious.

So, I come to you hours before the ball is tipped for the last time in this year’s college basketball season. Pardon any mistakes, I’m not missing the game for a newsletter. So, it’s a 40 Minutes of Hell approach today.

You filled out a bracket or two. So did I. We talk ourselves into a few upsets, and convince ourselves this is the year the underdog makes a run.

We believe in it. We root for it.

But when we go to work, we bet on favorites. Again and again.

Let’s be honest. Even in March, we don’t really bet on chaos. We pick a few upsets, enough to feel sharp, but we anchor to the higher seeds because it’s safer, because it’s defensible.

And in business? We don’t even pretend.

We bet on track records.
We bet on known names.
We saddle up next to winners.

We call it strategy.

Sometimes it is.

But, a lot of times, it’s just safe. Safe is comfortable

When you only bet on winners, you don’t necessarily reduce risk. But you definitely reduce you own dynamism. You default to consensus over conviction. You prioritize pedigree over potential.

And over time, something shifts.

You stop asking:
What do we believe?

And start asking:
What can we defend?

That’s Where Culture Slips

Because “We Play it Safe!” isn’t exactly an inspiring personal or professional tagline.

There’s a better chance a business proclaims, “We Innovate!” “We Take the Shot!” “We Believe!”

But culture isn’t what you say, it’s what you invest in. It’s who you believe in. It’s what and who you support.

If your culture is built on trying new things, on trusting your people, then blindly betting on the favorite, especially when it doesn’t align, isn’t strategy. It’s drift.

Why We Still Love the Underdog

Underdogs reminds us of who we think we are. It’s a story we tell ourselves on tough days and sleepless nights.

In March, we see talent without resources. We see leadership without infrastructure.

“They’re good enough to win. They just haven’t had the chance to prove it yet.”

And sometimes…that’s true.

Not every Cinderella fades. Some of them rewrite the game.

In 1985, Villanova Wildcats, an 8 Seed, beat the Georgetown Hoyas. The ultimate glass slipper that never broke.

Not more talent, but better execution. They had absolutely precise passing to break the Hoya’s press and went 22 off 28 field. They slowed the game down to a trickle. Bad TV but killer strategy.

Unexpected execution and belief.

Netflix wasn’t the obvious bet when Blockbuster owned the market.

One had scale. One had a better read.

Airbnb didn’t fit the model. Too small. Too early. Until it wasn’t.

Crystal Bridges Museum of American Art wasn’t a safe, or even traditionally feasible, investment.

It was a belief that reshaped a region and redefined how art is experienced and who gets that access.

These weren’t lucky breaks. These were big bets by aligned teams with deep commitment.

They didn’t look like winners yet, but they operated like them.

When we only believe in winners, when we only invest in people, processes, or products that are already in place, over time, something subtle happens. The market passes us by. More over, we doubt our own dreams and dedication. Even more, your business gets boring.

When we pass on things we believe in because they aren’t validated yet, when we ignore signals because they don’t fit the model, we do so under the umbrella of “strategy.” Is it strategy?

Sometimes it’s just fear.

The Real Miss

The mistake isn’t believing in underdogs. The mistake is waiting until they’re no longer one.

If you say you value creativity and boldness then your decisions have to reflect that.

Especially when it’s uncomfortable. Especially when it’s not obvious.

Do the work…

Look at your last few decisions.

Where did you choose safe over aligned? Where did you follow instead of lead?

And where might you be one decision away from either reinforcing your culture or quietly eroding it, sharpening your edge or dulling it?