by Jay 

Struggling and Broke, He Was Offered a Big Payday – But One Powerful Question Changed Everything

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I Can vs I Will Attitude

Jesse Itzler thought he’d struck gold.

Young, broke, and hustling like his life depended on it, he was out there writing theme songs for sports teams, sleeping on friends’ couches, trying to make something stick. 

It was then that he received an offer: a music manager willing to give him $10,000, in exchange for 10% of everything he’d ever earn.

So when a music manager slid a contract his way, offering $10,000 upfront for just 10% of everything he’d make, it felt like the big break he’d been waiting for.

To Jesse, who had been struggling for any kind of foothold, that amount of money was hard to turn down. 

Ten thousand dollars represented a way out, a chance to pay off his debts, a moment of breathing room.

It felt like the practical thing to do, maybe even the smart thing.

But something about it felt unsettling.

This wasn’t a contract for his songs or a project fee; it was a stake in his future, and that was a weighty prospect. 

Feeling conflicted, Jesse mentioned the offer to a friend.

She suggested he talk with her father, Lou Katz—a man who’d built a business from scratch and knew a thing or two about making it on your own terms.

So Jesse sat down with Lou, explained his situation, laid out the opportunity, and then waited for a green light.

But Lou didn’t bite. Instead, he looked at Jesse and asked, “Will you make this business work without the $10,000?”

Jesse, confident and ambitious, leaned in, “I know I can make it work. I’m onto something.”

That’s when Lou’s eyes hardened, and he threw his notebook down. “I didn’t ask if you can. I asked if you will.”

The words hit Jesse like a punch to the gut.

Lou explained that saying “I can” was easy, but saying “I will” was a promise you make with your whole self, a commitment that leaves no room for excuses. 

It was the difference between a wish and a decision, between a maybe and a must.

Jesse felt something shift.

Suddenly, the $10,000 felt smaller.

He realized this was more than money. It was about staking his future on his own belief, not a payout.

That $10,000 would’ve been a quick fix, a small win. But for Jesse, stepping into “I will” was the key that unlocked his true potential.

He walked back to the manager and told him to keep the cash.

And that’s the lesson: if you want to make something big happen, something only you can create, stop waiting for validation, for safety nets, for guarantees.

Decide that you will—and let that commitment drive you, even when the road gets tough.

Because in the end, it’s not the money, the luck, or the connections that keep you going.

It’s the unshakable decision to see it through, no matter what.

So next time you’re faced with a choice, ask yourself—not if you can, but if you will.

This post was inspired by Jesse Itzler's interview in My First Million podcast.

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Jay

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