The “Binary” Outcome of Entrepreneurship
I carry a nearly constant, irrational fear that if my company fails my professional life will be over. I’ve been surprised to find my friends all carry the same fear.
On January 27, 2013, one of my mentors, Jody Sherman, committed suicide. Those who knew him well cited anxiety around the looming failure of his startup. At 47, we’re told Jody felt he was too old to start over.
Every founder, CEO, or startup leader I know carries this exact fear around every day. The fear that if this fucking company doesn’t work my life is, in some way, over.
I was discussing this topic with one of our investors on Tuesday. She confided in me that most VC’s carry around this fear as well. If their funds don’t return, they fear they’ll be unable to raise follow on funds and be imminently unemployable.
Amazing. The secret burdens we all carry in silence. While we’re all ‘killing it.’
Imagine the unspoken anguish that exists in many board rooms. The operators fearing for their livelihood, the well being of their families, and their career prospects. The investors ratcheting up the stress out of their own fear and insecurity. And nobody talking about any of it. All while the company goes through the inevitable ups and downs of building something from nothing.
We’re all dealing with this.
Every last one of us.
I’ve become close friends with the founding and operating team of one of the most successful startups in the country. In spite of the success, the tens of millions of revenue, the $100M+ in funding, each person on that team is struggling. The investors are stressed out. The company faces new threats weekly. The board is at risk of imploding. And that’s what success looks like!
I turned 37 years old on Friday. I’ll share my fear openly.
I’ve been running my company for five years.
Five years!
We’ve raised over $15M in funding including equity and debt.
Our revenue has grown 2x+ every 6 months for the last two years.
This is what success looks like.
And depending on the day, I’m either 95% sure we’re going to succeed and I’m going to ‘make it’ or 95% sure we’re totally fucked.
This week, following my birthday on Friday, I’m finding the fear particularly present. Although we are on a six-month streak of consistent growth, I’m scared it might end. I’m afraid, even now, of a world where Twenty20 fails.
Crazy scenarios run through my head.
I’ll have to sell my house. How will I pay my son’s tuition? Who will hire me? A ‘never had a real job, burned $15M at his last gig, 40-year-old, washed up, CEO wanna be?
I’m admittedly irrational. I know.
You probably are too.
But it still haunts me.
And I watch it haunt my close friends.
The reality is I have no idea what is going to happen. I’ve seen companies grow to $100M+ in revenue only to be sold off to return cash to investors. I’ve seen companies grind for 10+ years, through dozens of ‘should have been dead’ moments, to phenomenal outcomes. (BTW, a little company called Nike falls in that bucket. Read Phil Knight’s book.)
We are all irrational.
The reality is all of this fear is a fool’s errand and entirely irrational.
Embracing the fear is a fool’s errand because this week's, this month's, even sometime this year’s numbers tell us very little about the eventual outcome.
It’s irrational because the ‘worse case scenarios’ by which we’re all haunted aren’t all that bad. If you want to build companies, you’ll build another company. If you want to invest in companies, you’ll find another firm. The problem is the focus that makes us capable of these jobs also makes us dreadfully myopic.
The most heartbreaking part of Jody’s story was how loved he was by the people around him. How impactful he was on their lives. To this day, I carry with me the advice Jody gave me. And I only spent a few precious hours with him.
Each one of us is drastically underestimating the impact we are having on the world around us.
If the outcome is unknowable, we must do our best to find value along the way. The impact we have in building things is far larger than we can know. On our employees, our customers, and the people around us whom we inspire merely by taking the brave steps of the unconventional path. Fuck the outcome. You’re killing it if you’re making the world bigger and braver for a few people around you.
Wishing you peace today.
