CEO of Cal.com Bailey Pumfleet: building an open source rocketship (”Stripe for Time”) | ODF alum

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