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He Went Bankrupt at 16. Now He Makes Every NFL & NBA Jersey.
Success doesn’t wait for permission.
Michael Rubin didn’t have a pedigree. He didn’t have elite training or generational capital. He barely had a license to drive. What he did have was a work ethic that refused to quit and instincts that only sharpened under pressure.
By 12, he had a ski shop in his parents’ basement. By 14, a retail store with inventory he didn’t technically own. By 16, he’d been sued over a hundred times, buried in debt, and told to shut it all down. He didn’t. He flipped the inventory. Flipped the business model. Built it all back again.
Every misstep taught him how to move faster. Every early win reminded him what he was good at. He never stopped betting on that.
Today, Rubin runs Fanatics, a killer sports platform that’s vertically integrated, fan-obsessed, and holding its own against Amazon.
He started with grit. He built with failure. And he never waited for anyone to tell him it was okay to try.
Rubin’s method is chaotic, driven, and refreshingly direct. And if you’re ready to stop waiting for permission, you’ll want to steal a few pages from it.
Turn chaos into compounding interest.
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[the spark]
Play the Hand, Not the Heat
Michael Rubin learned the rules by breaking them.
At 14, he was running a profitable ski shop without anyone realizing he was still in high school. At 16, he lost it all after a snowless season, a Porsche he couldn’t legally drive, and 100 lawsuits from vendors he couldn’t pay.
He should’ve quit. Instead, he cracked a new play.
He took a risky loan to keep his head above water, cold-called ski shops out of the Yellow Pages, and flipped the inventory wholesale. He managed to pay off the high-interest loan in weeks and walked away with a blueprint: move fast, sell smarter, and never rely on perfect conditions.
By 21, he was the largest wholesaler of closeout footwear in the world. By 38, he sold GSI Commerce to eBay for $2.4 billion and bought back Fanatics, the consumer businesses they didn’t want.
Then came the power move: he rebuilt Fanatics as a vertical platform, controlling the product, the brand, and the customer relationship. Today, it's a $10 billion platform that's defensible, even against the likes of Amazon.
Rubin didn't wallow in his failure. He weaponized it.
The goal is to make each loss push the process further.
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[the science]
Dig Deep, Finish Strong
In the mid-2000s, psychologist Angela Duckworth set out to discover why some people achieve more than others, even when talent or intelligence seemed equal.
Her research led to the concept of “grit” – a combination of passion and perseverance for long-term goals. Studying high achievers in challenging arenas from West Point Military Academy to the National Spelling Bee, Duckworth found that dogged perseverance often outshines raw talent as a predictor of success.
At the elite West Point Academy, Duckworth found that a simple grit score turned out to be the best predictor of which cadets would endure the punishing summer training (“Beast Barracks”).
She studied top candidates from Scripps' National Spelling Bee and noted that the grittiest students, not the smartest, got the furthest in the competition, as the sheer force of their effort and determination paid off over time.
From these findings, Duckworth identified two key components behind extraordinary achievement:
- Passion for long-term goals – Champions maintain a deep, enduring commitment to their vision, keeping interest and enthusiasm alive over the long haul.
- Perseverance – They put in sustained, hard work and push through setbacks or failures without giving up.
So, Duckworth found that success is often less about some innate genius and more about the drive to keep going when others quit. It's the daily grind that hones the edge that champions use to turn goals into reality.
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[the takeaways]
1) Make the Pivot the Plan Don’t aim for perfect conditions. Build a model that adapts under pressure and adjusts fast when the landscape shifts.
2) Take Action Before It’s Safe Rubin didn’t wait for permission; he just moved. Calculated risk, taken quickly, beats hesitation every time.
3) Let Failure Rewire You Each collapse reveals a better path. Use breakdowns to test assumptions, expose weaknesses, and evolve the strategy.
4) Own More of the Process Vertical control gave Rubin the power and clarity to build his dream. When you own more, you learn faster and win bigger.
5) Train for the Long Haul Success compounds when effort is sustained. Grit is a system: commit to the work, push through friction, and keep showing up.
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