Whenever I hate my business I do this:

Every time I feel bad about my business - which is often - I get dinner with a VC backed Founder in the $20-30m ARR range who has raised over $50m. I share my complaints, then they share theirs👇

- They are unprofitable
- They’re either stuck or not growing fast enough for their investors
- Their investors send them all the Clay and AI financing news weekly
- They have 5x the team size I do (and execs)
- They are on planes at least 1x/week (I hardly travel)
- They are being forced to add product complexity
- They face intense new-entrant competition despite superior product
- They are under an incredible amount of stress and don’t see a way out

After they are done… it always kicks off the same dialogue:

CEO: “But you’re making money, right?”

Me: “Yea, we will probably do $12-14m profit this year."

CEO: “That sounds like the absolute dream.”

To which I always get reminded that... Yes, it actually is!

But when you’re in the middle of it all, it’s so easy to lose sight of.

Startups are hard.

Some things get easier, but in my 12 years of experience, it almost always feels like shit.

But if you can last long enough as a bootstrapper:

1. You will end up being enormously profitable (mini exits every year)
2. You will have total freedom to design the life you want for yourself

Raising money is exciting and validating, but most of the time you end up stuck with no way out.

The reality?

$10m ARR is the FU Money of SaaS.

In 2025, it takes fewer FTE’s than ever before.

At RB2B we’re about to cross $6m ARR growing 5%/mo with a team of 3.

99% of VC backed founders would kill for that business.

If you can bootstrap, bootstrap.