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

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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

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

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