My biggest mistake, the second time, was setting insane Year 1 projections.
I had such a great set of co-founders, I projected we’d hit $2m ARR in our first year. That was back in 2006 in SaaS! And for real. I was 100% sure we’d hit it.
We probably hit $0.2m instead. It was so hard on the team, one of us quit. We almost ran out of money. Things we rough.
But, I screwed up. Going from no product to $200k in ARR in SaaS in 2006 was pretty awesome, actually. Not A+ performance, but not a bad first year. And we closed Dell, Comcast, BT, GE, and other leading customers. In year 1. Not for huge contracts, but for real.
So I think I learned a crazy plan is good. But an insane one, you have to be thoughtful about how you use it.
And that even the world’s best-built model — and mine was pretty good, really — can harm you if the inputs and assumptions are highly improbable. At least, do more validation. More research.
We had a great team. But I needed at least 1 great mentor, too. To tell me $2m ARR in Year 1 wasn’t just ambitious, but borderline insane for a new product in a new market in a new category in 2006 in SaaS. And to at least have a “base plan” that was less insane.