You Just Gotta Push Through the Tough Times. It Always Pays Off.

And you’ll almost fail indeed during some low times. But you’ll look back and see you got through those with tenacity and commitment. And actually missed other things that were most important to really worry about.

Near-death / low-time examples:

  • Running out of money. This is indeed scary as heck. But somehow, someway, the best founders find a way.  A bit more here.
  • Losing your #1 customer. This is terrible. But it also teaches you how not to lose the next one.  A bit more here.
  • Having to go without salary. This isn’t fun. I’ve had to do it twice, once for a year. But later, it will recede to the past, and won’t really matter — if you can push past it.  A bit more here.
  • Your key VP / co-founder quitting. This is also terrible. It can really set you back. But somehow, the rest of the team rallies and you are often in a better place in 90 days.  A bit more here.

What you’ll really look back later and regret, and realize mattered more than the classic “low times” body blows:

  • Not pushing through tough times. You’ll look back and see you could have pushed through almost anything.  A bit more here.
  • Selling your company too early. Many founders that sell post-traction are haunted when they look back and see they in fact had a 10+ year run ahead of them.  A bit more here.
  • Taking too much money from the wrong lead VC. The distraction here can be enourmous. Battles, disagreements, lack of support in the next round, and much more.  A bit more here.
  • Hiring a terrible core VP, COO, etc. This ends up being much worse than losing someone. A truly terrible VP you keep on for too late just leaves a wake of damage, poor hires, missed goals, and unhappy customers behind.  A bit more here.
  • Toxic cofounder conflict. Sometimes this can’t be avoided. But while it rarely kills startups, it ends up wounding them far more than a lost customer or term sheet.  A bit more here.

Published on May 28, 2021

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