

The Surprising Cost of Kit.com with Nathan Barry
This week on Unf*ck My Startup:
We brought in the guy everyone pretends to be—Nathan Barry. No VC fairy dust. No growth hacks. Just a dude who built a $40M+ ARR company (ConvertKit → now Kit) by actually doing the work and giving a sh*t about creators.
We get into why most founders are LARPing as CEOs… and how Nathan scaled a real business without selling his soul.
Here's how it goes down:
00:00 – Who the fck is Nathan Barry (and why I care)
03:40 – From $0 to Kit: how ConvertKit became the creator platform
08:10 – Why he turned down VC cash (and never looked back)
14:25 – How to go from solo builder to actual CEO
21:00 – The underrated power of building with, not for, your audience
26:15 – Community vs competition: the mindset shift that matters
33:50 – Playing startup vs. building a business (you know who you are)
39:10 – Nathan’s no-bullsht advice for founders who want to scale and stay sane
Real talk. Real founder. Real revenue.
If you’re tired of startup fantasty—this one’s for you.
Find out more
https://www.linkedin.com/in/retentionadam/
https://www.youtube.com/@retentionadam
https://www.rb2b.com/