Hey, fintech fam 💜

Guess what… I am logging out (mostly) for 2 weeks starting TOMORROW.

I can barely believe it.

The Fintech Is Femme wedding season is in full swing! 👰🏽‍♀️ Reply now with your last bit of advice before the big day, or forever hold your peace 😆

Don’t worry, our Tuesday and Thursday chats are still happening even while I’m away, and we’ve got some pretty cool ideas up our sleeves.

My team will be running much of the show while Anton and I are out celebrating, and all I can say is I am feeling grateful that this team is made up of world-class talent.

Today, I’m talking about a recent conversation I had (watch the full thing here!) with the Founder and CEO of Sail, Danny Friday.

Danny Friday started Sail for one particular reason, and when you learn what that reason is, you’ll be shocked.

Let's get into it. ✨

Danny Friday, founder and CEO of Sail, tried to get reimbursed for a dental procedure he had done in Mexico. 

He submitted his receipt, and it was denied because it was in Spanish. If you’re thinking “WTF… how is this still an issue?”, so was Danny Friday. 

That moment became the founding logic of fintech startup Sail. 

The U.S. healthcare reimbursement system had just rejected a valid claim because of the language printed on a piece of paper. 

You might be thinking, “This is a healthcare problem,” and you’d be correct. But if you’ve been working in the finance space as long as I have, you know it’s actually an institutional problem.

And one that fintech can fix.

Hard truth: the system (be it healthcare, tradfi…) wasn't designed for you. Or your customer. Or your friends and family. 

This truth shows up everywhere: in overdraft fee structures, in cross-border payment rails, in credit underwriting models that still penalize people for not having a traditional employment history. 

The current systems were designed to hold a lot of variables at once, and somewhere along the way, your ability to understand how to navigate them became someone else's problem. 

Healthcare and finance are a lot alike in this way. 

The terminology alone (co-pays, deductibles, HSA versus FSA, eligible expenses) functions as a filter. 

People who grew up around this language navigate it. People who didn't lose money, time, and access until they figured it out. 

A 2025 survey from Change Healthcare, conducted across nearly 2,000 consumers, found that 62 percent of Americans say the healthcare system feels like it's designed to be confusing. 

More than 60 percent said their medical bills feel more complex than a mortgage payment. More than half said they avoid care entirely because they don't know what it will cost. 

That's an infrastructure problem. The solution? Accessible fintech. 

Sail's core product is simple: link any credit or debit card to an HSA or FSA account and use it to pay for eligible healthcare expenses. 

You don't need a separate healthcare card. You don't need to remember which wallet it's in or explain to the pharmacist why your card isn't working. You just use the card you already have.

Sail built the software layer that sits between the card network, the merchant, and the user’s benefits account. 

It handles eligibility verification, reimbursement logic, and the incredibly specific rules that govern what counts as a qualified medical expense without making the customer learn about it. 

That’s true access. 

Harvard economist John Campbell, co-author of Fixed: Why Personal Finance Is Broken and How to Make It Work for Everyone, said this to CBS News:

"You have a race between financial literacy and the complexity of the products people are offered, and complexity has been winning the race.”

His argument, and it's one I've seen play out across years of reporting on fintech, is that the burden has been placed on individuals to navigate systems they were never given the tools to understand.

The fintech companies that are actually disrupting our industry and changing the system from the inside out are absorbing the complexity so the user doesn't have to carry it.

It’s one thing to create a solution and push it to market. It’s another to distribute that solution in a way that actually removes friction from your customer’s daily life. That's the standard Sail is building to.

The HSA and FSA system runs on its own card infrastructure. 

Most providers issue a separate card tied directly to the account, and that card is the only way to spend HSA or FSA funds without going through a manual reimbursement process. If you don't have your card on you, you pay out of pocket and file a claim later, which is exactly what happened to Danny Friday in Mexico.

Sail removes that separate card. It links to a credit or debit card you already carry and connects it directly to your HSA or FSA account on the back end. 

When you make an eligible expense, Sail automatically verifies eligibility and processes the transaction against the correct account, without the user doing anything different from what they would for any other purchase.

That healthcare product requires fintech infrastructure: card-linking technology, real-time eligibility verification against IRS-defined qualified expenses, and a settlement process that connects the transaction back to the HSA or FSA provider. 

That's the intersection in practice. Healthcare created the benefit and the rules around it. Fintech built the layer that makes the benefit usable without the consumer having to understand the rules.

It’s why you’ll always hear me say that fintech is the most powerful industry in the world. It’s everywhere, all the time. Intersecting with and operating alongside the industries our world operates on, like healthcare.

The U.S. healthcare reimbursement system and the U.S. consumer financial system were both built for institutional actors, and the consumer experience was an afterthought. 

Fintech has spent the last decade proving that you can redesign financial products around the person actually using them.

Sail is making the same argument about healthcare payments.

This opens a roadmap for every other consumer touchpoint in healthcare where the same dynamic exists: pharmacy benefits, medical billing, insurance navigation. 

The infrastructure problem is bigger than one card, but Danny Friday is starting there. 

The world’s top fintech and Big Tech leaders are coming together September 29th-October 1st in San Francisco.

We’ve been told AI makes work easier.

How do we make sure that sentiment remains true? How do we avoid adding more problems to our business by introducing AI?

We’re uncovering all of it at FTW: SF. Get your early bird tickets now!

Hilary Duff is on tour right now, so this felt right.

And if you didn’t know she was touring (or you have no idea who she is), maybe Fintech Is Femme can be your new source for all things pop culture, too 🤪

📰 Share this newsletter with a friend and start growing your network.

🔗 Connect with me on LinkedIn for daily insights on leadership.

🤝 Grow your business through content & community by partnering with me.

📣 Promote yourself to 50,000 subscribers by sponsoring this newsletter or the Humans of Fintech podcast.

🎤 Host an epic event by booking me as a speaker, moderator, or emcee.

📚 Increase your expertise by ordering your copy of my book, Fintech Feminists: Increasing Inclusion, Redefining Innovation, and Changing the Future for Women Around the World.

Thanks for spending time with me today.

Love,

Nicole 💜