Running toward the cliff: the courage of entrepreneurs

Founders learn to live on the cliff of capability and see only the clouds, not the rocks below. How do they develop that gut?

Heading out of Brooklyn, I was having dinner last night with the CEO of a venture-backed startup. She captured what so many founders face when she shared that her day-to-day felt like: running toward a cliff. Not only that, encouraging a growing team to run toward it with her at full speed. Her situation is pretty typical:

  • The startup is burning investor money and will be running out on a very knowable date in the near future
  • The code being tested has a ton of bugs and is behind schedule; the code in the wild isn’t what you’re selling now on your latest pivot.
  • Your team is struggling with the growth and uncertainty. They have some fragility and need to see their leader confident.
  • Your daily mental exercise routine includes talking to mostly well heeled, comfortable people (investors) who haven’t hired or led a team in years, if ever, and explaining yourself to them in ways that make them feel inspired and safe. (Them’s that have the money makes the rules.)
  • Another part of your daily core strengthening routine is talking to customers. They’re not all thrilled with you.
  • Then there are the prospect meetings–you’re selling something a bit different than the pitch last month so you feel like there’s always a new cadence, and it’s up to you get it right first so you can lead the team to scale it.
  • You manage all of this, but what you’re really wanting is to realize your future vision that isn’t built yet. You want the future, but you have to go through the present to get there.
  • Sometimes, you’re just overwhelmed–physically, mentally and emotionally. You don’t share this, because your team, customers, prospects, new hires and investors all need to believe in the future, not that you are courting crumbling.

    Founders learn to live on the cliff and see clouds, not rocks.

The courage of knowing the cliff is there–and even the date you’re jumping–and still believing you might learn to fly by the time you have to jump is a monumental act of human courage. Still motivating yourself and the team to run with something very close to genuine enthusiasm for the race is a beautiful and terrible ability that separates the gut of the true founder from the rest of the population. That said, last night reminded me how much entrepreneurs and founders need a safe place to share, even for few minutes, the reality that is theirs alone. Whether it’s a spouse, best friend, EO forum, or some other group where the confidence is iron clad, it’s a critical outlet for staying sane and strong. And you might just consider hugging your founder today.