Re-Imagineer: Jacob Lewis

You seem to be a committed Re-Imagineer. You spent 14 years in magazine publishing, 12 of those years as the Managing Editor of The New Yorker, but you stepped out of that world to become an entrepreneur by launching Figment, an online community for teens and young adults. What provoked that change?

I had wanted to be an entrepreneur for years but it was a professional inflection point that really spurred on the change for me. I had, as you mentioned, worked at The New Yorker for twelve years, followed by another two years at Condé Nast Portfolio, a new business magazine. I really loved my time working in magazines, especially at The New Yorker. It was, in many ways, where I grew up and got an education. It taught me what it means to be a great editor, and I learned so much about business and management. In 2009, Portfolio was shut down after running headlong into the financial crisis. The ad market, as you know, just fell off a cliff. Condé Nast offered me a job at a different magazine, but I viewed it as a now or never opportunity. If I was ever going to take the leap to be an entrepreneur, this was the moment. 

Making that leap was incredibly difficult, and financially risky. I really had to reorient my whole way of thinking about and approaching work. I didn’t, at the time, have a mentor or a blueprint for how to move forward so it was initially very disorienting. I essentially had to teach myself how to start and build a new business. But I had a lot of drive—I felt I needed to prove to myself that I could build something from scratch—and that really propelled me forward. I had successfully led a relatively large team in a corporate environment, and I wanted to build something from scratch. I wanted to see if I could exist as someone with their own ideas, their own drive, their own initiative. 

It was, without question, the best step forward I ever took. It required a lot to find the will and momentum but it fundamentally changed my career and life for the better. 

After four years of running Figment, you spent nine years involved in other entrepreneurial activities, including starting two other companies, and as a start-up advisor and consultant. What advice would you give to people who want to set off on their own to build a professional portfolio?

Leaving the corporate world and launching Figment allowed me to have a career where I was truly in charge of my own destiny and my day-to-day existence. For me being who I am and especially at that time, this was the right decision. It enabled me to push myself and the boundaries of what I was capable of.

In 2013, I sold Figment to Penguin Random House, and subsequently worked there as a book publisher for a couple of years. That experience, in book publishing, was the only other corporate position I have held since Condé Nast. I have no regrets about returning to publishing, but my experience there really drove home that my independence in business was fundamentally important to me. 

I have, since then, co-founded two other companies, and worked as an advisor and consultant to a number of other start-ups. 

I believe entrepreneurship is truly one of the best experiences for people inclined toward it. You have to be ready to make all the decisions (even the bad ones). You have to be able to manage incredible peaks and valleys. You have to have a vision and be a strong operator. But it can be incredibly rewarding and gratifying even though the risks are real. The rewards, for those who can handle the uncertainty, are well worth it.

The key factor is trusting yourself. Even more than having a good idea for a new business  – ideas, after all, are a dime a dozen – is the belief that you can execute on a vision and move the ball forward on your own initiative. That’s not only about success. It also means your ability to handle and overcome adversity. Because sometimes it does feel like an endless stream of mistakes and hurdles and bad luck. 

I think a lot of people have the mental fortitude and the skillset to go out on their own, but sometimes just need that extra push or jump in order to set the ball in motion.  

But the big news is your new Re-Imagineer play! You have just completed a Wilderness EMT course. Why and how did you decide to do this and where will it lead you in this new chapter?

Of course, all things change. This past year, I made the decision to start a new chapter. I left my most recent entrepreneurial venture and I have dedicated myself to working outdoors. I have spent a good portion of my working life looking for periods of time to escape in order to go hiking, backpacking, and backcountry skiing. It brings me an incredible amount of joy to be in nature and experience natural beauty.

As much as I loved being an entrepreneur, I am acutely aware of my age. I don’t say that because it’s a limiting factor, but I want to give myself the time to experience and be involved in the activities and environments I love. And there’s only so much time I can stare at a screen! 

My first step was to become certified as a Wilderness EMT, which means I’m trained as an EMT as well as in wilderness first aid. My plan is to use these skills to work on ski patrol, join on search and rescue missions, and guide trips into the backcountry. I am going to endeavor to spend as much time as I can spend in the wilderness, and combine it with helping others, for the foreseeable future. 

In some ways, it’s not too dissimilar from my decision to become an entrepreneur. In 2022, I took a now or never approach and pushed myself to make a change that is scary and risky, but will make me happy and enable me to find adventure in this one life I have. 

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