Here are 5 questions that always make me feel like shit about myself as a founder:
How many employees do you have? (”oh - so you’re just getting started …”)
What’s your revenue?
You’re in tech? How much money have you raised? None? Oh.
Do you have an office? Oh okay.
What’s your company called? Wait - what did you say?
I will say that while this soul-crushing feeling of “smallness” happens less and less to me every year, it still definitely happens. In many worlds (the Aspen YPO chapter, for example), $30m in revenue is peanuts, a team of 30 is tiny, and sadly, in America, size matters, and bigger is better.
But MAN I remember the PAIN from back in the day, year 2, 3, 4 …
We only had a couple mm’s in revenue, we were stuck, I had ZERO confidence in myself as a founder, we grew our team to 38, shrunk it to 6, our business was called “Robly” (WHAT?), I had NO IDEA how we were going to get unstuck … and meanwhile I was living in New York in a golden age of VC-backed tech, living in a world of constant anxiety and FOMO, watching EVERYBODY around me absolutely CRUSH IT.
Or so it seemed.
If you fast forward to today - now 12 years after we launched our first product - if someone actually takes time to understand the details of the operation we have going on, ALMOST NO ONE says anything other than “that’s one of the best businesses I have ever heard of.”
What changed?
I just kept building, and along the way there was an external change, and an internal change.
EXTERNAL:
The first thing SORT OF worked. $3m ARR, stuck, $10m exit. The second thing worked a bit better. $20m ARR, 25 employees. The third thing REALLY worked. $10m ARR, 3 employees. Now I’m on to the 4th thing, which will probably look a LOT like the 3rd - but we’re still early.
None of that is mind blowing, but you add it all together, and - at least in my opinion - it actually IS one of the most beautiful businesses in the world.
INTERNAL:
I still get the “oh that’s cute” eyes every once in a while, but today I truly believe I have an incredibly beautiful business that gives me energy for other parts of my life, exactly the life I want, and one that I hope to have the privilege of working on for decades to come.
So the eyes don’t sting, because I know I want what I have, even if others who blow me off don’t value it.
I think it would take a person much more zen than me to rise above the crushing social pressure of being small and stuck at $3m in an environment like NYC in 2015-2020. If you can achieve that level of independent thinking, more power to you.
For everybody else, my advice is to just keep building. Keep throwing spaghetti at the wall. If you just keep going, some day you will wake up and realize all of your dreams have come true.
Adam