The Dream and the Pain Cave

The Duality of Life as an Entrepreneur and as a Human

As our star rose, people would say:

You must be living the dream.

The honest answer was this:

I am trapped in a pain cave and I can’t get out.

It was a lie. But I didn’t know that yet.

Struggling with depression, freaking out about how to make payroll, dealing with our cofounder’s departure, terrified that we couldn’t raise more money, not knowing how to hire people, not knowing to fire people, creating a dysfunctional culture and not knowing why, creating a wonderful culture and not knowing why, spending too much money on marketing, burning too much cash, not innovating enough, innovating too much and getting distracted, corrupting friendships with business, getting conflicting and yet seemingly sage advice from different investors, wondering if our product was good, trying to figure out if our business model would work, looking for our first dollar of profit, anxious that we had picked the wrong industry, and ultimately wondering one thing.

Am I good enough?

Do they know I’m a fraud? Will I be able to return this money with a multiple to our investors? Will our customers forgive us if we fail? Will I let our team down? These wonderful people who put their heart and soul into our company, don’t they deserve better?

Entrepreneurs are not that special. If you are one, stop drinking the Kool Aid, and if you aren’t, definitely don’t drink it.

The life of an entrepreneur is the life of a human. Some days are amazing. Some days are a struggle. A lot are in between. It’s the same for all of us. The American lionization of the entrepreneur is to ignore its foibles — the narcissism, the workaholism, the neglect of family, the imbalance, the obsession. These are not universally good things, though they are frequently universal to building great companies. In America, we love entrepreneurs. In America, entrepreneurs don’t always love themselves. My belief is we are no different than non-entrepreneurs, except the highs and lows are amplified by the stress of inheriting responsibility we haven’t earned. We all have an entrepreneur in us, it’s just whether we choose the trade offs to become one. You can start something or create something tomorrow. The question is not just do you want to, it is should you? Can you afford to? Most importantly, do you know what to start?

Most CEO’s have experience with leadership. Most entrepreneurs do not. Most CEO’s have experienced a lot of life. Most entrepreneurs have not.

The founding CEO is living the dream some days. Other days she is trapped in a pain cave. The particular struggle of the founding CEO is that not only is it the company you lead, it is your “baby”, the company you created, and everything wrong is your fault.

Now, when people ask me if I am living the dream, I say something I borrowed from a man named Liam, and I say it with a laugh and almost as a joke, but it’s an honest joke. I think it’s from Oprah:

You know, just living my best life!

My real takeaway is from Biggie Smalls.

From him I learned that the whole thing is a dream, pain caves included. The pain cave days are the ones you learn even more from, they help you cultivate the resilience required for life on those days, and enduring them makes all the other that much more magical.

It was all a dream. I used to read Word Up! magazine.

— Notorious B.I.G.

I don’t know what Word Up! magazine is, but I do know this:

It is all a dream.