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

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

Tämä jakso on lisätty Podme-palveluun avoimen RSS-syötteen kautta eikä se ole Podmen omaa tuotantoa. Siksi jakso saattaa sisältää mainontaa.

Jaksot(487)

Sword Health to Buy Headspace, Unrivaled Hits $650M, Life Time Gets Social

August 27, 2026: Your daily rundown of health and wellness news, in under 5 minutes. Today's top stories: Sword Health plans to acquire Headspace in an all-cash deal, expanding its AI-led platform in...

27 Elo 3min

Fitbit Founders Return, Amazon Bets on HYROX, GLP-1 Care Consolidates

Here's the podcast description for August 26, 2026: August 26, 2026: Your daily rundown of health and wellness news, in under 5 minutes. Today's top stories: Fitbit founders launch Luffu and its Link...

26 Elo 3min

Oura's Data Dilemma, Lady Gaga's Biotech Bet, Men's Wellness Nears $3T

August 25, 2026: Your daily rundown of health and wellness news, in under 5 minutes. Today's top stories: Oura faces a proposed class action over sleep-tracking accuracy claims just months after fili...

25 Elo 3min

353. Clara Sieg, Co-Founder & CEO of Loonen

Today, I'm joined by Clara Sieg, co-founder & CEO of Loonen. Born from Clara's personal mission to avoid toxins in drinking water, Loonen's ultra-filtered, glass-bottled spring water emphasizes puri...

24 Elo 31min

Crosscourt Raises $2M, Crunch Goes Premium, EoS Bets on HYROX

August 21, 2026: Your daily rundown of health and wellness news, in under 5 minutes. Today's top stories: Crunch Fitness relaunches Crunch Select with boutique studios and premium amenities, using it...

21 Elo 3min

Target Taps Wellness, AI Personalizes Food, Sports Become AI-Proof

August 20, 2026: Your daily rundown of health and wellness news, in under 5 minutes. Today's top stories: Target adds 4,600 new food items in a grocery overhaul leaning into discovery and emerging br...

20 Elo 3min

Neko Expands, Happy Health Raises, Sequel Taps WNBA Star

August 19, 2026: Your daily rundown of health and wellness news, in under 5 minutes. Today's top stories: Neko Health opens its first US clinic in SoHo on September 24 after building a 25,000-person...

19 Elo 2min

Purely Elizabeth Get Acquired, Women's Sports Surge, Gen Z Stays In

August 18, 2026: Your daily rundown of health and wellness news, in under 5 minutes. Today's top stories: Ferrero Group acquires Purely Elizabeth, the wellness food brand that more than doubled sales...

18 Elo 2min