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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 |