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]

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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.

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

February 20, 2026: Your daily rundown of health and wellness news, in under 5 minutes.

Today's top stories:

• Ergatta joins Interactive Strength portfolio alongside Wattbike, CLMBR, and FORME, continuing independent operations under CEO Tom Aulet

• D1 Training hires Harris Williams to explore sale, operating 170+ locations serving 100K+ scholastic athletes in $154B youth sports market

• Hims & Hers acquires Australian telehealth platform Eucalyptus for $1.15B, expanding globally with brands serving 775K patients across Australia, UK, and Japan

I'm heading to LA this week for the Connected Health & Fitness Summit to host a fireside chat with Fritz Lanman, CEO of Playlist (parent company of Mindbody and ClassPass), on AI in fitness and the anticipated $7.5B EGYM merger. If you're attending or based in LA and want to meet up, email [email protected].

More from Fitt:

Fitt Insider breaks down the convergence of fitness, wellness, and healthcare — and what it means for business, culture, and capital.

Subscribe to our newsletter → insider.fitt.co/subscribe

Work with our recruiting firm → https://talent.fitt.co/

Follow us on Instagram → https://www.instagram.com/fittinsider/

Follow us on LinkedIn → linkedin.com/company/fittinsider

Reach out → [email protected]

February 19, 2026: Your daily rundown of health and wellness news, in under 5 minutes.

Today's top stories:

• Andrew Huberman calls retatrutide a potential trillion-dollar drug, showing 30% weight loss in Phase III trials with muscle preservation

• Lululemon launches Studio Yet. in LA, a three-week pop-up blending workouts with retail as stores become training extensions

• Garmin reports record Q4 revenue of $2.12B up 17%, with fitness segment climbing 42% driven by wearables demand

Joe Vennare is heading to LA this week for the Connected Health & Fitness Summit to host a fireside chat with Fritz Lanman, CEO of Playlist (parent company of Mindbody and ClassPass), on AI in fitness and the anticipated $7.5B EGYM merger. If you're attending or based in LA and want to meet up, email [email protected].

More from Fitt:

Fitt Insider breaks down the convergence of fitness, wellness, and healthcare — and what it means for business, culture, and capital.

Subscribe to our newsletter → insider.fitt.co/subscribe

Work with our recruiting firm → https://talent.fitt.co/

Follow us on Instagram → https://www.instagram.com/fittinsider/

Follow us on LinkedIn → linkedin.com/company/fittinsider

Reach out → [email protected]

February 18, 2026: Your daily rundown of health and wellness news, in under 5 minutes.

Today's top stories:

• Americans now spend 6.3 hours daily on phones, up from 5.5 hours in early 2023, with older users driving surge

• Raw sugar futures fall to five-year low as GLP-1 drugs accelerate decline in sweet consumption while whey prices hit record highs

• Federal law caps THC in hemp products near zero in November, potentially eliminating much of $8-13B CBD market

I'm heading to LA this week for the Connected Health & Fitness Summit to host a fireside chat with Fritz Lanman, CEO of Playlist (parent company of Mindbody and ClassPass), on AI in fitness and the anticipated $7.5B EGYM merger. If you're attending or based in LA and want to meet up, email [email protected].

More from Fitt:

Fitt Insider breaks down the convergence of fitness, wellness, and healthcare — and what it means for business, culture, and capital.

Subscribe to our newsletter → insider.fitt.co/subscribe

Work with our recruiting firm → https://talent.fitt.co/

Follow us on Instagram → https://www.instagram.com/fittinsider/

Follow us on LinkedIn → linkedin.com/company/fittinsider

Reach out → [email protected]

February 17, 2026: Your daily rundown of health and wellness news, in under 5 minutes.

Today's top stories:

• YC-backed Fort opens pre-orders for strength-specific wearable that auto-detects exercises, reps, sets, and fatigue without manual logging

• Stanford-born Clair develops wrist-worn device using 10 biosensors and AI to estimate real-time hormone levels including estrogen and progesterone, shipping in November

• Matrix Bio claims to have built five-minute, $5 multi-marker hormone test requiring no lab or blood draw, pending clinical regulatory validation

I'm heading to LA this week for the Connected Health & Fitness Summit to host a fireside chat with Fritz Lanman, CEO of Playlist (parent company of Mindbody and ClassPass), on AI in fitness and the anticipated $7.5B EGYM merger. If you're attending or based in LA and want to meet up, email [email protected].

More from Fitt:

Fitt Insider breaks down the convergence of fitness, wellness, and healthcare — and what it means for business, culture, and capital.

Subscribe to our newsletter → insider.fitt.co/subscribe

Work with our recruiting firm → https://talent.fitt.co/

Follow us on Instagram → https://www.instagram.com/fittinsider/

Follow us on LinkedIn → linkedin.com/company/fittinsider

Reach out → [email protected]

Today, I'm joined by Sam Browne, CEO and co-founder of Let's Do This.

A platform for mass-participation sports events, Let's Do This partners with marathons, triathlons, and cycling events to help people discover life-changing athletic experiences.

In this episode, we discuss building tech to get people together offline.

We also cover:

• The company's mission to create shared experiences

• Current problems with the experience economy

• Expanding to 18 international markets

Subscribe to the podcast → insider.fitt.co/podcast

Subscribe to our newsletter → insider.fitt.co/subscribe

Follow us on LinkedIn → linkedin.com/company/fittinsider

Website: www.letsdothis.com

Let's Do This on Instagram: https://www.instagram.com/letsdothis.com_/?hl=en

Sam's LinkedIn: https://www.linkedin.com/in/sam-browne-a86268b0/

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

(01:03) Background and mission

(02:13) Offline connection

(02:41) Origin story

(04:30) Identifying market gap

(05:23) Discovery, technology, and payments problems

(06:45) Layering growth S-curves

(09:00) The ultimate growth channel

(11:30) The supply side

(13:45) Technology infrastructure

(16:00) COVID impact

(18:30) Post-pandemic surge

(21:00) Isolated, distracted, or connected

(23:15) Why experiences beat things

(25:30) Bringing people together

(27:00) The choice

(29:08) Expansion strategy

(30:15) Geographic rollout

(31:15) Future verticals

(32:00) Supply problems

(33:09) Lifetime partnerships

(34:18) Serving event organizers

(34:48) Where to discover your next challenge

(35:32) Conclusion

February 13, 2026: Your daily rundown of health and wellness news, in under 5 minutes.

Today's top stories:

• Erewhon partners with Ject to offer lip flips and brow lifts at exclusive LA event, marking second move into med spa space

• Harvard study of 100K+ Americans over 30 years finds exercise variety predicts lifespan better than single modality, with 19% lower all-cause mortality

• Nike Strength rolls out equipment across 25 Everlast Gyms in UK and Ireland, expanding commercial partnerships beyond consumer training gear

More from Fitt:

Fitt Insider breaks down the convergence of fitness, wellness, and healthcare — and what it means for business, culture, and capital.

Subscribe to our newsletter → insider.fitt.co/subscribe

Work with our recruiting firm → https://talent.fitt.co/

Follow us on Instagram → https://www.instagram.com/fittinsider/

Follow us on LinkedIn → linkedin.com/company/fittinsider

Reach out → [email protected]

February 12, 2026: Your daily rundown of health and wellness news, in under 5 minutes.

Today's top stories:

• Amazon One Medical launches Health Insights powered by Lifeforce, analyzing 50+ biomarkers with AI-driven lifestyle coaching for Prime members

• Cambiotics raises $5M seed round to commercialize probiotic removing PFAS "forever chemicals" from the body, targeting firefighters in U.S. clinical trials

• Hinge Health reports Q4 revenue up 46% to $171M with full-year revenue climbing 51% to $588M, serving 25M individuals across 2,800 clients

More from Fitt:

Fitt Insider breaks down the convergence of fitness, wellness, and healthcare — and what it means for business, culture, and capital.

Subscribe to our newsletter → insider.fitt.co/subscribe

Work with our recruiting firm → https://talent.fitt.co/

Follow us on Instagram → https://www.instagram.com/fittinsider/

Follow us on LinkedIn → linkedin.com/company/fittinsider

Reach out → [email protected]

February 11, 2026: Your daily rundown of health and wellness news, in under 5 minutes.

Today's top stories:

• Solace Health raises $130M Series C at $1B+ valuation, connecting patients with nurse advocates to navigate care and insurance

• Weight Watchers partners with Pvolve to bring streaming strength workouts into medically guided weight loss and menopause care

• Function Health sues Superpower over "100-plus biomarkers" claims, highlighting pressure on diagnostic platforms to define measured versus inferred data

More from Fitt:

Fitt Insider breaks down the convergence of fitness, wellness, and healthcare — and what it means for business, culture, and capital.

Subscribe to our newsletter → insider.fitt.co/subscribe

Work with our recruiting firm → https://talent.fitt.co/

Follow us on Instagram → https://www.instagram.com/fittinsider/

Follow us on LinkedIn → linkedin.com/company/fittinsider

Reach out → [email protected]

February 10, 2026: Your daily rundown of health and wellness news, in under 5 minutes.

Today's top stories:

• Apple scraps AI-powered health coach project after delays, concluding it wasn't keeping pace with competitors like Oura, Whoop, and Ultrahuman

• Oura files patent for AR smart glasses displaying real-time health data controlled through ring-based gestures, positioning itself at center of ambient health tracking

• Hims & Hers pulls compounded oral GLP-1 pill amid regulatory pressure from HHS and FDA, with Novo Nordisk suing for patent infringement

More from Fitt:

Fitt Insider breaks down the convergence of fitness, wellness, and healthcare — and what it means for business, culture, and capital.

Subscribe to our newsletter → insider.fitt.co/subscribe

Work with our recruiting firm → https://talent.fitt.co/

Follow us on Instagram → https://www.instagram.com/fittinsider/

Follow us on LinkedIn → linkedin.com/company/fittinsider

Reach out → [email protected]