The Entrepreneurial Journey Is More Darkness Than Light

One of my seed founders reached out to me recently, requesting an immediate weekend sit-down. He needed advice because his “company was imploding.”

The company had in the bank most of the money it had raised from its seed round. It had recruited a staff of exceptionally talented engineers who were deeply passionate about their mission — and working for reasonable wages. But it was collapsing upon itself because of irreconcilable differences between the founders.

As we talked through the trauma, it became clear there was unlikely to be a path out of the morass. I suggested the parties find a way to agree to disagree and find a way for one group to go forward with the business. Or, if that was impossible, work out as clean a way to unwind as possible to protect future opportunities for all involved.

His response was somewhat chilling; the other founders had no interest in protecting the future or finding a way forward. They had moved here for the entrepreneurial journey, and if it failed them, they’d merely move home.

What they were going through at that very moment was the entrepreneurial journey.

Looking at startups from the outside, it’s easy to assume the startup game is just that, a game. A game with big winners and glorious and rapid rises to the top. Of billion-dollar valuations and worldwide conquests. Of apps serving hundreds of millions of people and liquidity to ensure glory for one’s heirs for generations to come.

But entrepreneurship is not a game, and the vast majority of the time spent on the journey (one I have and do live, embrace and love to my core) is a slog, spent dealing with pain and strife and conflict. Essentially, it’s:

  • Customers that don’t convert.
  • Senior people who leave.
  • Champions at partner companies who leave their jobs before the contract is signed and leave you to start over again.
  • Founders who disagree.
  • Tech that fails to scale.
  • Key positions that seem impossible to hire.
  • Big companies that keep you from hiring their people by giving them bonuses 5X what you were offering to pay them when they agreed to join you.
  • Bills that outgrow resources.
  • Payroll that haunts you just beyond your ability to pay it without another round of capital.
  • Financings that don’t close, or take far longer than expected.
  • Competitors that get the press you deserved for work less compelling than your own.

To name just a few that come to mind. The entrepreneurial journey is hard. It’s just plain hard.

I have had many occasions to counsel founders in difficult times; many have gone on to success, some have gone on to failure. My message is consistent. It’s going to get worse before it gets worse. And then, maybe, if you keep pushing through that, as well, it may get better. Just keep pushing through. And remember, good or bad, amazing or horrific, it’s all part of the same entrepreneurial journey.