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:
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Confusion around HSAs & FSAs
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Value props for merchants and consumers
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Integrating with Equinox's membership flow
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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: sam@withflex.com
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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.
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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
