Entrepreneurship is a full-contact sport, not a highlight reel.
After watching the Simone Biles and Ilia Malinin moments — when everything aligns, gravity seems to bend, and the world applauds — it’s easy to believe greatness is about perfect landings.
It isn’t.
What actually shapes you as a founder is what you do the day after you fall on the ice in front of millions.
That’s why I’d rather try and fail than not try at all.
When the Landing Hurts
American skater Ilia Malinin walked into the Olympics as the guy who does the “impossible.”
He’s the only person to land a quadruple axel in competition. He even has his own signature move — the raspberry twist — something no one else has attempted.
Expectations weren’t high. They were sky-high.
Then, in the men’s free skate, he crashed. He missed his hardest jumps. He fell twice. He left the ice in shock and heartbreak — and he couldn’t hide it.
If you’re an entrepreneur, you can relate.
A launched product flops.
A funding round doesn’t close.
A key hire doesn’t work out — maybe even a family member you trusted.
You don’t just lose the routine. You lose the story you already told yourself about how this was supposed to go.
From the outside, people say, “He choked.”
From the inside, it feels like, “Maybe I’m not who I thought I was.”
That’s the emotional reality of trying and failing in entrepreneurship.
The Message Every Founder Needs to Hear
In the stands that night was Simone Biles — the most decorated gymnast in history, with five skills named after her.
She knows what it’s like to be branded the GOAT — and then have a very public unraveling.
In Tokyo, she battled the “twisties,” lost herself midair, and withdrew from team competition under crushing expectations and scrutiny.
So when she saw Malinin fall, she didn’t send a motivational quote.
She sent bullet points:
- Validate his feelings
- Let him know he had support
- Remind him that “you can still come out on top”
Read that again from a founder’s perspective.
She didn’t say, “It’s not that bad.”
She didn’t say, “Just shake it off.”
She said:
You’re allowed to hurt.
You’re not alone.
This moment doesn’t define your career.
That’s the message most entrepreneurs never hear.
Instead, we’re told:
Grind harder.
Rise and grind.
Sleep when you’re dead.
What we actually need is perspective from tenured team members who can say:
“You did something remarkably hard. It didn’t work this time. Feel it. Learn from it. You’re not done.”
Trying and Failing in Entrepreneurship Is a Data Point, Not a Verdict
After Tokyo, Simone Biles didn’t disappear.
She regrouped.
She rebuilt her mental game.
She improved her work-life balance.
And she returned to win four medals — three gold and one silver.
Same person.
Different chapter.
That’s entrepreneurship.
The market trashes your first version.
The investor you were sure would say yes says no.
The team doesn’t execute as you hoped.
The question isn’t “Did you fail?”
The question is:
What do you do with the failure?
If you never attempt the “quadruple axel” of your business — the bold product launch, the new market expansion, the acquisition, the turnaround — you might avoid embarrassment.
But you also avoid upside.
Trying and failing in entrepreneurship is not a bug in the system.
It’s a feature of the process.
Building a Culture Where It’s Safe to Try
As a founder and leader, here’s what I take from Biles’s interaction with Malinin.
1. Normalize Big Risks
Malinin wasn’t failing at something easy.
He was attempting something only he could do.
In business, growth comes from bold moves — not safe reactions.
2. Acknowledge the Crash
When someone on your team misses badly, don’t rush to judgment.
Do what Biles did:
Acknowledge the pressure.
Acknowledge the disappointment.
Acknowledge the humanity.
People recover faster when they feel supported.
3. Separate Identity from Outcome
One bad Olympics didn’t erase who Biles was.
One failed product doesn’t erase who you are.
Help your team understand:
A failed project does not make a failed person.
4. Keep the Future Open
“You can still come out on top” isn’t false optimism.
It’s recognition that the story isn’t finished — as long as you’re willing to step back onto the ice.
As a founder, you are the chief storyteller.
If you treat failure as shameful, your team will hide theirs.
If you treat failure as expensive tuition, they will experiment.
Why I Will Keep Walking Onto the Ice
Trying and failing hurts.
But not trying at all is worse.
Not trying means letting fear override conviction.
It means choosing a smaller life so no one sees you fall.
Simone Biles and Ilia Malinin remind me:
The job isn’t to guarantee a perfect landing.
The job is to keep doing work worth falling for.
As entrepreneurs, we owe ourselves — and our teams — this commitment:
We will attempt hard things.
We will miss sometimes.
We will validate each other’s crashes.
We will step back out under the lights.
I’d rather try and fail in entrepreneurship than never know what might have been if I’d gone for the quadruple axel in my own business.
