327. Sam O'Keefe, Co-Founder & CEO of Flex

Today, I'm joined by Sam O'Keefe, co-founder & CEO of Flex.   Enabling use of HSA and FSA funds at checkout, Flex unlocks tax-advantaged spending on preventative health products — from fitness and recovery to supplements and wearables.   In this episode, we discuss making "pay with HSA/FSA" as common as PayPal.    We also cover:   Confusion around HSAs & FSAs Value props for merchants and consumers Integrating with Equinox's membership flow    Subscribe to the podcast → insider.fitt.co/podcast  Subscribe to our newsletter → insider.fitt.co/subscribe  Follow us on LinkedIn → linkedin.com/company/fittinsider    Flex's Website: www.withflex.com  Shop with Flex: www.withflex.com/shop  Instagram: www.instagram.com/paywithflex/  LinkedIn: www.linkedin.com/company/withflex/  X (Twitter): https://x.com/paywithflex  Sam's Email: [email protected]    -   The Fitt Insider Podcast is brought to you by EGYM. Visit EGYM.com to learn more about its smart fitness ecosystem for fitness and health facilities.   Fitt Talent: https://talent.fitt.co/  Consulting: https://consulting.fitt.co/  Investments: https://capital.fitt.co/    Chapters: (00:00) Introduction (01:39) Sam's background (02:26) Why HSA/FSA funds are hard to use (04:00) Making HSA/FSA work (05:35) IRS regulations (07:05) The education problem (09:00) Merchant value proposition (10:30) Increased accessibility (11:10) API-first infrastructure (12:05) Custom integrations (14:40) Patterns across fitness, sleep, supplements, wearables (16:15) Women directing family healthcare spending (18:00) Subscription retention (19:15) Psychology of separate health spending pool (21:25) Equinox partnership (22:40) Seamless checkout integration vs reimbursement friction (24:15) Fitness language shift (25:05) Making HSA/FSA ubiquitous in every checkout (27:15) $150 billion underutilized in HSA/FSA accounts (28:40) Consumer marketplace (29:30) Growing B2C alongside B2B focus (30:30) 2026 priorities (32:33) Conclusion