Dear SaaStr: What Are The Worst Realities of Being An Entrepreneur?

The worst reality, which is also part of what makes entrepreneurship so visceral — is the true feeling of Failing With 100% Responsibility.

It often doesn’t leave you until $20m, $30m ARR, or sometimes much later, even in SaaS.  I remember interviewing Todd McKinnon, founder CEO of Okta (now at $2B+ ARR), saying it wasn’t until $30m ARR or so he felt they weren’t going to fail:

You will never, ever feel Failing With 100% Responsibility as a “mere” employee. It’s hard there, too — but it’s not the same. If you aren’t the founders, and the business fails. You pick yourself up, and find another job. You move on. If as a non-founder, you fail at your individual job, that is rough. But the company can survive that. You move on.

But as a founder, every day you aren’t succeeding, you are failing. And you will feel it in your gut every moment of the day:

  • From the moment you launch a product for real, but without customers, you will be failing. You will feel it every day.
  • From the moment you have customers, but until you have enough to have a self-sustaining business, you will be failing. This is one of the most stressful phases of all.
  • When you have a self-sustaining business, but you aren’t growing “fast enough” — you will be failing. And you have to shield the employees from a lot of this, yet also, push them to go harder and stronger.
  • When you will never be No. 1 or No. 2 in a space, you are failing, at least in a sense. You have to redefine who you are, somehow. Some way. No one wants to work at No. 6.
  • When you can’t hire the VPs you need to scale. You are failing. No one can see this on a daily basis. But it weighs on you constantly.

The Highs are Higher, The Lowers are Lower. This is true. But it oversimplifies that a big part of the Lows is — Failing. The stress of failing. Even in seemingly big success stories.

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