There are so many mistakes I made in the early days.

But the #1 thing I wish I’d told myself is this: getting from $10m to $100m in revenues is very doable.

I knew a few things as a founder:

  • I knew how to sell to big companies.
  • I knew how to get the first few million in revenue.
  • I’d been through an IPO, and a big acquisition, as an executive — but not as a founder.

What I didn’t know, not really, is what $10m to $100m in ARR was like in SaaS. Not back then. There weren’t many comparables, except Salesforce. I didn’t have the role models to know I could do it.

In fact, I sold just as we past that point. It felt like it would be forever until an IPO, and that that path was very risky.

That was a mistake. Getting from $10m to $100m in ARR does indeed take a lot of time, if you aren’t Slack.

But, the thing is — you know how to do it by then. Even if you don’t realize it.

If you have a strong team, and decent market position, and are growing fast enough at $10m ARR … you can get to $100m+ in ARR.

It’s just a matter of time.

Put differently, this is when you start to get the benefits of power laws.

It’s not that things get easier. But you get so much better.

I knew everything at $10m in ARR I needed to know to get to $100m+ in ARR.

I just didn’t know that I knew that 🙁

I needed better mentors. Get the best ones you can.

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