Am I an Imposter?

The Weary Souls of Entrepreneurs

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Banks Benitez said it perfectly.

When I was interviewing Banks about his work as the VP of Global Expansion at the Unreasonable Institute, a start-up school for social entrepreneurs, one of his founders shared about what it feels like to be an entrepreneur: “It’s like I just joined the very front of the parade and people are cheering me on.”

He continued, “Today it seems like entrepreneurship is almost this embodiment of the American dream. You have this small idea and then you figure it out along the way and you grow and become really wealthy and successful – and you’ll also solve a global problem. Everybody wants you to become like Tesla, and the world is cheering you on…”

But on the inside, being an entrepreneur is fraught with emotional pain and difficulty. One of his founders said in a post-experience survey, “I don’t deserve to have this platform. People don’t really know who I am, and once they really find out who I am they’re going to be unimpressed.”

That’s it. Exactly.

I started Denver Institute for Faith & Work in 2012. As I look back, I think it was a combination of luck and lots of God’s grace. Board members joined, a handful of donors got behind the idea, and we started holding public events. It was odd at our first event to say, “We at Denver Institute…” What is Denver Institute? Just a fiction? We have only a couple thousand dollars in the bank, and yet I’m acting like this is somehow real?

As the organization grew, we began to hire a few staff, got a foundation to underwrite much of our work, and moved into our office. And it was a very odd feeling: in the period of 12 months I went from working in an old, decaying shopping mall at a small Christian school to getting connected to millionaires and city leaders. What just happened to me?

My public persona was growing – often despite myself – and yet tension followed me almost every single day. I would watch the bank account. “We have exactly 6 months until we’re out of money, and then we close the doors, I would think to myself.” Where am I going to get more money to keep this going? Donors, staff are depending on me…

I felt a strain on my relationship with my wife, and with my kids. My work had been consuming. Until one day, divinely, my six-year-old daughter even called me out for making my work an idol.  I felt an acute sense of shame.

And I got into this work because I’m driven by a conviction, that I could solve a key problem in the world. But now I’m leading a staff team, reading P&L statements, trying to manage sales with operations with finance, and I’m afraid to let me know know I don’t really know what I’m doing. I feel like a top that is spinning, and is soon to tip over.

​The contrast between my internal world and my external reputation was creating a chasm, often void of peace and hope… and of God.

Imposter. Once they found out who I really am…

A couple years in, I realized I wasn’t alone. One article in The Economist called it Founder’s blues. All of us founders are filled with energy and entrepreneurial fury. But underneath the fervor is a world of uncertainty. “In the morning you feel everything is on the right track and in the evening everything seems in the gutter,” said Shawn Zvinis, the co-founder of Tab, a London startup which eventually closed down.  The stress can sometimes even become grimmer. Tragically, some entrepreneurs buckle under the pressure and take their own lives. This happened to an entrepreneur in Denver just last year.

As I searched for answers, I was both glad to see the problem being acknowledged – but I found the answers coming from the secular world were painfully insufficient. Much of the counsel coming to entrepreneurs takes into account how to build a lean start-up or access venture capital, but little of the questions that were plaguing my soul. How long can I sustain this kind of life? What will I do if I fail? Where is God in this process (didn’t he call me to start this, anyway)? Who am I becoming? Good advice or tropes like “fail fast” weren’t enough.

Because these questions were gnawing away at my soul, this spring I decided to gather a group of friends and peers to talk about “Caring for the Soul of Entrepreneurs,” one of our breakout sessions at the June 15 event “For Whose Glory: Exploring Faithful Practice in Life, Leadership and Business.”

Of course, I invited Banks, my friend, a 5280 Fellow, and a key leader at the Unreasonable Institute. I also invited Reilly Flynn, Managing Partner at GAN Ventures and fellow follower of Christ. As a venture capitalist, Reilly works with entrepreneurs every day. And as he evaluates new deals, he also recognizes that entrepreneurs are people, with hopes and dreams and frailties and failures.

My Tuesday morning prayer partner, John Paasonen, CEO of tech start-up Maxwell, will also be there (assuming kid #2 doesn’t arrive on that day!). As a Duke MBA, former executive for American Express and PayPal, he came to the start-up world with a unique resume and amount of experience. Yet still, the tension of spending investment capital, hiring staff, and scrambling for new customers, even amidst having a killer product – well, he’s felt what we all do this space. Tension.

I also invited both Henry Kaestner, founder of Sovereign’s Capital, and his colleague, Russell Bjorkman, to join us. Sovereign’s is unique: not only do they work exclusively with Christian entrepreneurs, but their unique niche in this space is caring for the souls and emotional health of their entrepreneurs. Reilly has said that Henry is one of the most faithful thinkers/practitioners in the land on this topic.

Finally, my friend Drew Yancey, who is President of Yancey’s, a food service company, and doing a PhD in both theology and business right now, will be there facilitating the discussion. His research interest in the moral formation of entrepreneurs – yet his heart has also been deeply impacted by his own failures in the world of entrepreneurship.

The Front Range lacks a place for Christian entrepreneurs to come together both for business support and spiritual direction. As a nonprofit entrepreneur who has felt the tensions of both heart and hand, spirit and strategy, I hope this small gathering is the beginning of something bigger… for the sake of our city, and, quite selfishly, for my own life.  

Learn more and join us for conversation on June 15>>