A CEO friend of mine just shut down his startup after 12 years. He raised over $30m in VC, and the co-founders’ families put in $2m. In 2017, he tried to hire me saying they’d “soon be worth $1B.” I was shocked at what he said when I turned him down:
CEO (to me): You’re not ambitious enough.
Me: What???? Why do you say that?
CEO: It's been 5 years, man. You’re wasting your life on your tiny startup. It’s not going anywhere.
Me: Yeah, but it’s MY tiny startup.
CEO: We’ll be worth a billion soon. A small part of my startup will be worth so much more than your large stake of yours… And you’ll have a bigger impact working for us.
Me: I have two main objections. First, paradise to me is a mid-20’s ARR SaaS with under 40 people. I don’t know how I’m going to get there, but that’s what I’m going for. Second, even if my startup is worth less and it’s less impactful, it’s MY startup, which your startup is not. You work for the VCs. I’d rather spend my time working on my own thing, even if I stay stuck here.
CEO: You’re too talented to be thinking so small.
———
You already know how the story ends.
I now have my mid-20 ARR startup with 40 employees.
Here’s the craziest thing:
We generated $1m in profit the same month he closed his doors.
Believe me - my friend no longer thinks I’m “not ambitious enough”.
Here’s a few lessons for my fellow bootstrappers:
1. The world is really hard on you when you’re small. Stay strong.
2. If you’re small but profitable, you can stay in the game.
3. The skills and effort you’re compounding are VERY valuable.
4. If you build skills and stay in the game long enough, the odds that you will get lucky and hit it big skyrocket.
Don’t let people tell you you’re wasting your life.
Massive success is inside all of you.
It just takes LOTS of time, and usually a little luck.
Happy Holidays.
Thank you for taking the time to consume my thoughts.
I hope you can take some time to enjoy your loved ones, your team, and this incredible game that we have the privilege of playing every single day.
Keep building.