That’s what she said to me. It was around 2004 and she was a mentor to me. I held her in such high regard, I admired her and when she spoke I listened. We were having lunch on a beautiful spring day in Harvard Square, dining on a restaurant patio. She was cultured, she had the pedigrees, she’d been around the world and back, and she’d totally kicked ass over her highly entrepreneurial career. Now, in her early 60s, she was as wise as she was inspiring. And she said, “you know, you can be very abrasive sometimes.” My fork stayed steady in my hand while I paused and humbly and sheepishly responded, “I know.” I sat back to hear her out.
A few years later I find myself far from the guy I was then, yet very much still that guy. I feel like I’ve come full circle in many ways. And only when you go on that journey do you really learn. A pattern has been revealed.
Today I start a new stage of my career. After two and a half years at Litle & Co., as their Vice President of Marketing, and through their late 2012 acquisition by publicly traded Vantiv, I’m getting back to what I do best – startups and entrepreneurship. My experience at Litle & Co. was nothing short of educational and enjoyable. I learned so much. Most of all, I proved something to myself, and that was the biggest gain.
For the most part I’m taking time off, to enjoy spring and summer, to see friends and family, to enjoy life, but also to make my next move a smart one. The next stage of my career is an important one. At 37 it has to be wise. Not conservative, mind you, but wise. I often fantasize about a totally different career path, one of journalism, or of science, always something that might make real change in the world. As one of my best friends often says, “the last thing we need is another app to help me find the pizza, review the pizza, get a deal on the pizza, take a picture of the pizza, and clip recipes of the pizza.” I’m often frustrated by the lack of real innovation out there, truly transformative stuff, specifically in the digital space. Stuff that really makes a difference. But it’s not enough to be frustrated, that breeds apathy. Instead I’m embarking on something new here. I’m also often frustrated by what I’ll call the cult of personality that’s come out of and surrounds the Internet’s entrepreneurial scene, here in Boston, in NY, in Silicon Valley. Scenesters, hipsters, hangers-on. Me toos. That stuff is just such a turn off. And none of it even really matters. But again, it’s not enough to be frustrated and annoyed by it.
So with that I’m launching an experiment, if you will. I call it Sure Shot Labs. Sure Shot Labs will be the vehicle that helps me navigate this transition, these bumpy roads. Through Sure Shot myself and a few trusted and passionate colleagues will try something new for all of us. We’ll build products and invest in ideas we have, on our terms. The traditional start-up model is gone. The lean startup is here. We will consult, yes, we will make our clients happy indeed, and we will take the proceeds from those engagements and invest them in the lab, in our experiments, in innovation and in products. This will be fun.
When I think about that conversation with my mentor nearly 10 years ago, I think about the young man I was. I think about how “abrasive” I was. It was unearned confidence and it was fear. Back then I had to compete with others who were smarter, bigger, stronger, more experienced, more wealthy, more well connected, and more educated. Today I still have to compete with those people. And they still might be bigger than me, stronger than me, smarter than me, wealthier than me, more well connected and more educated. But what they lack, and have never been able to compete with, is my endless tenacity, my ability to wear them out, like a wolf and its prey. And the street smarts, the innate will to work smarter, to work harder, to out-think and out-smart, to out-play, to outwit and out-will. I’ve always been out of my league. I’ve always been in over my head. I’ve rarely done things their way. I don’t plan on starting today.