Craig Hatkoff is hard to categorize.
The 60-year-old is an entrepreneur, best-selling children’s book author, banker, real estate mogul, cofounder of the Tribeca Film Festival (with his wife, Jane Rosenthal, and Robert DeNiro), and cofounder of The Disruptor Foundation (with Harvard Business School professor Clayton Christensen and famous speaker and author Rabbi Irwin Kula.
But though Hatkoff’s career iterations may seem disparate, they all have one thing in common: They’re all about disrupting the norm, challenging the status quo—and being willing to try anything, even if it means failing wildly.
Here, he shares his unconventional path to success:
"Disruption is in my genes. My father owned one of the first discount toy stores, Duane’s Toyland, in Albany and Schenectady, near where I grew up. Discount was always a huge disruptor—it disrupted Sears Roebuck.
Like my dad, I was also a disruptor, though there wasn’t a name for it at the time. But I was your classic early adopter. I took computers in high school. I would do all my own programming, But I didn’t see the future of computers for anything other than data processing. Who was going to use a computer for communications?
I expected to join my father in business, but my brother-in-law, venture capitalist Alan Patricof, convinced me to go to Manhattan instead. So I went to Columbia Business school and in 1979, when I was 26, I took a job as a lender at Chemical Bank, now JP Morgan Chase. It was an utter disaster, an abysmal failure. I was a fish out of water. I couldn’t follow the rules. I asked too many questions. Memos to the board of directors weren’t supposed to be funny.
And oh, yeah: I was arrogant.
One day, I was summoned to an emergency meeting with the powers that be. They suggested that I give serious consideration to other career alternatives in different industries. I had never been so humiliated. For the first time in my life I had failed at something.
Instead of wallowing in self pity, I wrote up one of my "silly new ideas" in a succinct and compelling two page memo that were some of the seeds for one of the most radical ideas in the annals of banking: Asset securitization. The memo simply suggested that construction loans and other commercial real estate loans could be "sliced and diced" —cut up into different securities and risk preferences and selling off the funding risk, credit risk and interest rate different parties.
This two-page memo became my ticket out of hell. Within a couple of months I had gone from being a total flop to a virtual rock star. I had bombed out as a traditional lender, but it seemed I did have some other valuable talents that emerged from this trauma. By the time I was 29 I was co-head of real estate investment banking at Chemical Bank. I spent the next 20 years in the real estate finance business. Life was good.
But in 2000, I quit. I wanted to do something completely different. All I knew was that I loved technology, I loved innovation, I loved music and I wanted to write children’s books. So I began to immerse myself in all of these fields, all at the same time. Since then, My two daughters and I have written and published 15 children's books with Scholastic.
In December of 2001, after September 11th, my wife, Jane Rosenthal, and Robert DeNiro asked me if I would help them create the Tribeca Film Festival. The idea was to revitalize lower Manhattan. We would show films on piers, in highs schools. It was all about the community. We wanted it to be accessible to everybody.
But there was a catch. We needed to launch the festival in the next 120 days—it was the only slot on the film festival calendar that could work. It was crazy. We didn’t even have a business plan.
It was an epic struggle, but we never lost faith. We weren’t brave—maybe we were just oblivious. This April we concluded the 13th annual Tribeca Film Festival. It really can’t be explained in conventional terms. It was a total leap of faith. But it worked.
The point of all this is that my career has been a process of discovery. Steve Jobs talked about "connecting the dots." He said that you can only connect the dots looking backward. I disagree. I believe that if you simply have enough dots to connect, you can begin to connect them looking forward. With enough dots in your network of experiences the dots actually begin to connect themselves.
That’s how I feel about the experiences I’ve had in all these industries: banking, book publishing, the film festival. I have always tried to live by the "awe principle." That is: Can I find awe, wonder and enchantment in the most mundane things conceivable?
When I talk to people just starting out, I advise them to meet the most interesting people they can, people who are completely unlike them. When you become a one trick pony in your personal life or professional life—only talking to other people in the same stable—it gets stale. You’re certainly going to bore yourself to death. Or worse: you’ll bore others.
I’m especially interested in the idea of multiple fluid identities. Why just do one thing? Because whatever you think is certain today, is definitely not certain. The duration of the average Fortune 500 company is 15 years. It used to be 67 years. What does that tell you about the decisions you’re going to make?
Abraham Maslow said that "When your only tool’s a hammer every problem starts looking like a nail." I say, have a really big tool kit. Know as many disciplines and as many people as you can. Have as many dots as you can. The more dots you have, the better chance you’ll have of connecting them.
—Abby Ellin regularly writes feature articles for the Health, Style and Business sections of the New York Times. She the author of Teenage Waistland: A Former Fat Kid Weighs in On Living Large, Losing Weight and How Parents Can (and Can’t) Help. Reach her at abbyellin.com, or on Twitter.