Algorizin Series

17 Year Old Raised $32.4M to Connect a Billion People – Bailey Pumfleet

Episode 1Featured Guest: Bailey Pumfleet

Success Stories

Stream Insight on

Exclusive Story

Transcript

Duration1h 19m 21s

ReleasedMar 2, 2026

CategorySuccess Stories

Bailey PumfleetCal.comSiam Hossain

Keep Listening

More Episodes

View archive→

The CEO Improving Healthcare Access for 70 Million+ Americans - Sufian Chowdhury

New

Mar 2, 2026

Guest SpeakerSufian Chowdhury

The CEO Improving Healthcare Access for 70 Million+ Americans - Sufian Chowdhury

Sufian Chowdhury, Founder and CEO of Kinetic, who is improving healthcare access for over 70 million Americans through non-emergency medical transportation. Sufian shares his journey from a tough childhood in Queens and 18 months in consulting to building Kinetic over a decade, raising $32M+, and surviving near-death moments—from COVID and SVB to policy clampdowns—while staying focused on giving first, building real relationships, and staying humble as a founder.

Watch Episode

Everything you need to thrive.

Join a community of ambitious immigrants building successful careers in the US. Get exclusive access to expert roadmaps, deep-dive interviews, and legal insights.

Join host Siam Hossain on this inspiring episode of The 021 Podcast as he unpacks the remarkable journey of Bailey Pumfleet, Co-founder and CEO of Cal.com. Starting the open-source scheduling platform at the age of 17, Bailey has steered the company to raise $32.4 million from heavyweight investors such as Alexis Ohanian and Tobi Lütke, all while staying laser-focused on a moonshot goal: connecting one billion people through efficient scheduling by 2031.

In this conversation, we dive into Bailey's grounded upbringing near London, his contrarian approach to avoiding hyped-up tech trends (like Web3 and AI) in favor of solving "boring" but fundamental problems, and the massive impact of their strategic rebranding from Calendso to Cal.com. We also explore the stressful realities of being an immigrant founder navigating the US visa system, his thoughts on bootstrapping versus venture capitalism, and why he prioritizes a fully remote, asynchronous work culture. Whether you're an aspiring entrepreneur, a software engineer, or looking for practical business wisdom, Bailey's raw story offers a masterclass in building a scalable, impactful infrastructure.

17 Year Old Raised $32.4M to Connect a Billion People – Bailey Pumfleet

More Episodes

The CEO Improving Healthcare Access for 70 Million+ Americans - Sufian Chowdhury

Everything you need to thrive.

Always know your next step

Bailey Pumfleet

Timestamp Highlights