CEO of Cal.com Bailey Pumfleet: building an open source rocketship ("Stripe for Time") | ODF alum
Here's how Cal.com CEO Bailey Pumfleet turned a side project into one of the most ambitious and fastest-growing infrastructure startups ever.
Cal.com CEO Bailey Pumfleet turned a side project into one of the most ambitious infrastructure companies ever.
His mission: powering a billion connections by 2031
Rather than just another Calendly alternative, they're building the "Stripe for Time" - scheduling infrastructure that powers everything from doctor's appointments to refugee services.
We get into:
[3:56] How startups get open source wrong
[10:46] Launching the v0 of Cal (called Calendso)
[24:32] Why open source is crucial for infrastructure companies
[36:30] The journey from MVP to enterprise-grade platform
[39:29] Building trust through radical transparency
[46:46] How their "longevity guarantee" wins enterprise deals
[47:15] Running a fully remote global team
[53:00] Handling compliance and security at scale
This is a must-watch for anyone building infrastructure, open source, or startups in general..
Enjoy!
Links mentioned:
ODF: explore starting a startup in SF and figure out co-founders, customers, and more at https://joinodf.com
StampList: browse breakout companies with a track record of sponsoring visas for exceptional talent at https://landing.club/stamplist
https://cal.com
https://x.com/BaileyPumfleet
https://x.com/peer_rich (Bailey's co-founder)
https://x.com/julianweisser
The Deep End is available on YouTube and other podcasting platforms:
https://www.youtube.com/watch?v=V2Pripb427E
Apple: https://podcasts.apple.com/us/podcast/the-deep-end-by-odf/id1568752165
Spotify: https://open.spotify.com/show/4TWOlf80GM1Pml8fGUO8KK