17 Year Old Who Raised $32.4M to Connect a Billion People: It’s Not About 7 Figure Deals, It Matters More When Refugee Camps Use It – Bailey Pumfleet

Welcome to the very first episode of The 021 Podcast! Today, we sit down with Bailey Pumfleet, the co-founder of Cal.com, a scheduling platform on a mission to connect a billion people by 2031. Bailey shares his journey from a teenage side project to building a venture backed profitable business, navigating the challenges of fundraising, and being an immigrant founder. This conversation is packed with insights, lessons, and inspiration for anyone taking their first steps from zero to one. Timestamps: 0:00 - Intro 1:18 - Who is Bailey? 2:01 - Cal.com and its roadmap to a billion users by 2031 8:00 - What made Bailey Pumfleet get into scheduling 12:20 - Bailey's childhood, growing up, and what made him the person he is 18:50 - From Calendso to Cal.com 22:35 - How much did you buy Cal.com for? 29:29 - Trustbuilding around Cal 32:20 - Intentions behind going open source 39:57 - What's the change that led to the biggest impact? 43:20 - Raising $32.4 million to build Cal 49:10 - Bootstrapping vs VC funding – decision metric for early stage founders 51:20 - Bailey's struggles as an immigrant founder 56:50 - Rapid Fire round 58:30 - What's keeping Bailey excited? 1:02:26 - The biggest early stage mistake Bailey made 1:05:15 - Struggles of running a remote team 1:08:50 - The 3H Founder Matrix: Hacker, Hustler, Hipster 1:12:25 - One thing that Bailey does regularly 1:14:00 - What Bailey learned over the last 4 years as a founder 1:18:09 - Gifts and Closure Follow Bailey LinkedIn: https://www.linkedin.com/in/baileypumfleet/ Website: https://baileypumfleet.com/ Instagram: https://www.instagram.com/baileypumfleet/ X: https://x.com/baileypumfleet?lang=en Cal.com Follow Siam LinkedIn: https://www.linkedin.com/in/siamhossain/ Newsletter: https://sojourningwithsiam.beehiiv.com/ Instagram: https://www.instagram.com/siam.m.h/?hl=en Facebook: https://www.facebook.com/Siam.M.H/ Algorizin.com XenosWealth Thank you, and stay tuned for the next episode of The 021 Podcast.