He Quit the Best Job in the World. Then Built Something Better.
Jon Brod on risk, repetition, and the 30-year play that separates legends from everyone else.
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He Quit the Best Job in the World. Then Built Something Better
Jon Brod had a job most people would kill for.
As a marketing executive at the NBA, he helped launch the Toronto Raptors and Vancouver Grizzlies. He worked alongside David Stern and Adam Silver. He was living the dream.
And then he walked away.
Not because he failed. Not because he was pushed out. But because the entrepreneurial itch was real, and no amount of courtside seats could scratch it.
In this episode of Finding Peak, Jon and I dig into the psychology of risk, the power of positioning, and why the people you work with matter more than the idea you’re chasing.
Connect with Jon Brod:
LinkedIn: linkedin.com/in/jonbrod
The Risk Calculus
When Jon evaluates a new venture, he doesn’t start with the idea. He starts with the people.
His framework is simple:
Total Addressable Market (TAM) — Is the opportunity big enough?
The People — Do I want to work with these humans for the next decade?
Execution — Can this team actually pull it off?
The Idea — Only then does the concept itself matter.
Most entrepreneurs get this backwards. They fall in love with their idea and ignore everything else. Jon’s seen enough to know better.
The 30-Year Play
One story from the conversation stuck with me.
Jon asked David Stern why the NBA banned players from hanging on the rim after dunks. The answer wasn’t about showboating or sportsmanship.
It was about backboards.
Stern explained that in developing countries, basketball hoops are often attached to buildings or makeshift structures.
If kids see NBA players hanging on rims, they’ll do the same—and those backboards will break. Fewer backboards means fewer kids playing basketball. Fewer kids playing means a smaller global fanbase in 30 years.
That’s the kind of long-term thinking that separates legends from everyone else.
Repetition Is Your Friend
Jon spent time at AOL during its heyday. His job? Repeat everything. All the time.
Not because people are stupid. But because they’re busy. They’re distracted. They need to hear something seven times before it sticks.
This is the part most entrepreneurs hate. They get bored with their own message long before their audience has even heard it once.
But the greats—the Sterns, the Bezoses, the Musks—they say the same thing over and over until it becomes gospel.
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The Positioning Formula
Jon shared a fill-in-the-blank framework for positioning any product or brand:
“To [target audience], [product] is the [frame of reference] that offers [unique selling proposition].”
Simple. Brutal. Effective.
When he was launching the NBA in Canada, the question wasn’t “How do we sell basketball?”
It was “How do we position basketball against hockey, movies, concerts, and everything else competing for attention?”
The answer: entertainment, not just sports. Share of time, not just share of wallet.
The Rub
The line that hit hardest came near the end of our conversation.
Jon discussed the moment he decided to leave the NBA. He’d been wrestling with the decision for months. And then it clicked:
“This is our one big beautiful life. It’s not a dress rehearsal.”
If you’re sitting in a corporate job, wondering if you should take the leap, that line is either going to haunt you or free you.
Choose wisely.
This is the way.
Hanley
P.S. If you’re sick of feeling invisible and want to finally build a personal brand that will create leverage, influence, and growth for your business…I’m taking 1:1 clients. DM me today to learn more.
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The backboard example is such a perfect illustration of compounding leverage most operators completley miss. Most founders are obsessed with next quarter's metrics while Stern was engineering cultural adoption for kids who haven't even been born yet. Seen this firsthand managing infrastructure projects where the temptation is always to cut corners on durability to ship faster, but those shortcuts cost you the entire downstream market.