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Flex (YC S23) — Stripe for HSA/FSA payments

Flex is a payment platform for businesses to accept HSA/FSA, unlocking the $150B per year sitting in HSA/FSA accounts.

Flex is a Y Combinator company in the Summer 2023 batch. Its directory entry describes it as: Stripe for HSA/FSA payments. The founders listed are Sam O'Keefe (Founder), Miguel Toledo (Founder) (Y Combinator directory entry, July 28, 2023).

6 more companies from YC Summer 2023 ↓

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Flex

New accelerator entry · 2023-07-28 · the record

Summer 2023
batch
8
people
Growth
stage
Remote
region
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What the record says

BatchSummer 2023
Announced2023-07-28
StageGrowth
StatusActive
Team size8
IndustryFintech
Sub-industryFintech -> Payments
SectorsFintech, Marketplace, Health & Wellness
RegionsRemote, Fully Remote
BasedRemote
HiringYes
Sitehttps://www.withflex.com/shop
Founded2023
YC group partnerPete Koomen
Launches posted on YC2
Open roles listed1

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More on Flex and the records around it.

Also in YC Summer 2023

Same batch, Fintech first.

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In their words

Flex is a payment platform for businesses to accept HSA/FSA, unlocking the $150B per year sitting in HSA/FSA accounts.

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Example from a real report (our sample on Target): “The Q2 2026 earnings report, published August 19, 2026, showed adjusted EPS of $2.46 against an expected $2.33” Source: CNBC

A Full Report on Flex: verified, sourced, every claim cited, ready in a few minutes. See pricing.

What the Full Report on Flex covers

  1. The Short Answer

  2. Which Company This Is

  3. What They Do, And How The Money Works

  4. Who Runs It, And How To Reach Them

  5. The Money: Funding, Valuation, Runway

  6. Who Pays Them, And Who They Are Up Against

  7. Warning Bells

  8. Sources

    8 cited sources found

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If you're behind Flex: acceptance into a YC batch is one of the few weeks a young company gets looked up by people who matter — investors, other founders, press. FoxPlug turns the commits, deploys, and releases you're already making into that story automatically, so anyone who looks finds something current. GetFoxChat puts a guide on your own site so the people YC's own page just sent you don't read one line and leave.

Sourced from the company's Y Combinator directory entry, and from the company's own site, read directly on 2026-09-27 (withflex.com).

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Flex: Accepted into Y Combinator Summer 2023
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Permanent URL: https://mentionfox.com/funding/yc-flex
Last updated 2026-10-23
Primary record: Y Combinator directory entry
Flex (YC S23) — Stripe for HSA/FSA payments. MentionFox, 2026-10-23. https://mentionfox.com/funding/yc-flex