How to make a Founder feel small

18 months ago, I attended a birthday party for a founder who just raised $185M (at a $2B valuation) on the rooftop of the Four Seasons and was absolutely HUMILIATED by his incredibly attractive 28-year old blonde girlfriend:

Me: Hey, what’s going on?

Her: Thanks for coming. What do you do?

Me: I have this startup. What about you?

Her: I’m in marketing at UpWork

Me: I LOVE Upwork. We use them all the time.

Her: Cool. How big is your team?

Me: 6 people

Her: Oh... so you’re just getting started

*my internal monologue*

“Wtf… actually we are at $12m ARR, grew 200% this year, and me and my co-founders are making money hand-over-fist… we’ll have more revenue than your boyfriend in 6mo and we’ve PAID ourselves $5m getting here.”

…But I didn’t say that.

My face turned bright red, but I just swallowed my pride, made my best attempt at smiling, said “yep, just getting started,” and walked away.

Why did this bother me so much?

Why did this feel so humiliating?

Because everywhere you go as a SaaS founder, the first (and ONLY) thing anyone asks you is how big your team is.

They size you up.

When you say “six people”, you can see it in their eyes.

It’s an “oh, that’s cute” kind of look.

Or they feel sorry for you.

They definitely don’t take you seriously.

Most of time they start wanting to give you advice.

They don’t realize that your team of 6 gets more done - and has more ARR - than their team of 60.

Nobody cares that you have $2m ARR per employee.

Nobody cares that you can do literally whatever you want.

Nobody cares that your stress level is close to zero.

They care about are the headlines about people raising $50m pre-launch.

They want to read press releases about acquisitions, IPOs, and big teams.

This is the pressure that’s on the bootstrapped founder, every single day, from every angle, the entire journey.

It makes us feel little.

But it shouldn’t.

We have beautiful businesses that most VC-backed execs would kill for.

It’s hard to remember that when your head is about to explode because someone says “you’re just starting out”.

But you must remember, so you remain unbroken.

Stay small.

PS - there is a great video with more context and active comments section on this post.

Click here to check it out.