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When we first conceived the My Big Break series, I immediately thought of Jason Hirschhorn. Given that Jason is one of the best storytellers I know, I just knew he’d have a great story about who (or what) got him started on the road to success. 

I was right.

In fact, when I call Jason to ask about his “big break” story it turns out he has several. The best one, though — his true big break — is the story of how he went from a web designer, working out of his apartment, churning out site for musicians like Madonna, to a senior executive at companies including MTV, MySpace and  Slingbox. (This seems like a good time to mention Jason publishes MediaREDEF, which is about the only email newsletter I read every day without fail. You should subscribe immediately.)

[Note: The My Big Break series is being sponsored by Braintree’s Ignition program, so you’ll only see their ads around “My Big Break” pieces. But the series was conceived, commissioned and edited entirely by Pando. Braintree had no input whatsoever in the editorial. For more on our policy towards single sponsor series like this one, see here.]

Jason’s story starts back in 1995, in the early days of the first dot com boom. Having discovered Lynx and Usenet at his college’s computer lab, Hirschhorn knew he didn’t want to follow his classmates to a career at Anderson Consulting or Goldman Sachs. The Internet “nurtured me… made me want to go down my own path.” That path meant founding his own web design company, Mischief New Media, which specialized in designing websites for record labels and artists like Madonna and Seal.

Business was good at first, but soon the labels started bringing their web development in house. “I started building my own series of music sites,” Hirschhorn tells me, “with audio streaming, communities, that kind of thing.” By day he’d work for the music labels, by night he’d build his own projects. It was that nocturnal work schedule that lead to his big break.

“One of my design clients was Sony. At 4am one night I sent them an email about something. The guy responded ‘what are you doing up at 4am?’ I told him about my music sites, and he said: ‘We’re looking to do something like that. Can we see it?’”

“They were expecting to find an office and there was just me in my apartment at 96th and 3rd avenue, in sweatpants, unshaven, surrounded by stacks of magazines and computers. They figured it’d be easy — they said ‘don’t call anyone. We want to buy your company.’”

Sony clearly thought they were dealing with a rube.

“The next day all this stuff arrived — Playstations, music, minidiscs… a contract the size of a Torah.” But Hirschhorn wasn’t a rube.

He called his best friend from school, who happened to be a lawyer. More importantly his father happened to be Michael Schulhof — the former CEO and President of Sony America. “Let me take a look at the contract,” Schulhof said.

What he read wasn’t good. “‘Here’s what you’ll have after taxes,’ he said, ‘And you’ll be an 100k per year employee.’” Hirschhorn’s next call was to the man who gave him his big break: Arthur Indursky, an entertainment lawyer who he knew from another school friend. “He wasn’t really a technology savvy guy at the time. ‘Give me keywords’ he said, ‘Let’s shop this around.’”

Indursky called the heads of BMG and MTV and pretty much everyone else. “He mixed up every word — like ‘we’re doing streaming community’ — but started a bidding war that got me an offer seven times larger than Sony’s, eventually from Viacom.”

But that wasn’t his big break moment. “The deal was for stock in the internet play at MTV — Viacom was spinning off the music assets into something called MTVi — but at the last minute they refused to guarantee the stock. I still wanted to do the deal but Indursky stopped me. I remember saying, ‘why do we need a guarantee? The market is on fire, Look at Amazon.’ He said ‘If I were 8ft tall I’d play basketball, we’re getting that guarantee.’ If not for the guarantee that he pushed for, I would have lost everything because after the bubble burst in 2000, they cancelled the IPO. I walked away with the payout, because I took his advice.”

By 2003, Hirschhorn was the youngest senior executive at Viacom’s MTV Networks division.

Recalling all this now, Hirschhorn says something that really resonates with me, as someone who has made a living out of telling stories about his life. It’s a quote from Joe Walsh in the History of the Eagles documentary, and it perfectly sums up how very often it’s only possible to identify your big break moment after the fact.

“As you live your life, it appears to be anarchy and chaos, and random events, nonrelated events, smashing into each other and causing this situation or that situation, and then, this happens, and it’s overwhelming, and it just looks like what in the world is going on. And later, when you look back at it, it looks like a finely crafted novel. But at the time, it don’t.”

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