As many of you know, I started working with a triathlon coach earlier this year.

After tearing my ACL years ago, I thought 5K runs would always be my limit. But this year, I ran almost 9K for the first time ever and keep hitting new personal records. I’ve done things that used to intimidate me: joining masters swim groups even though I never swam competitively, biking more than 30 miles, saying yes to challenges that once felt out of reach.

Each time I think I can’t, somehow I do. And I keep asking myself what the secret is.

The secret, I’ve come to realize, is simply showing up.

(OK, and some encouragement - big shout out to Steve, a swimmer with SWIM Long Beach who got bitten by a shark, for telling me that I’m getting faster and faster after each swim workout. It’s seriously kept me going).

It is the same discipline that keeps me writing this newsletter every week. Each time I sit down to write, you show up to read, and somehow the magic happens.

In that spirit, I’ll be hosting a small coffee meetup this Halloween morning in Chicago for founders, investors, and builders who also believe in showing up — even when it’s hard, even when it’s cold. (Boo.)

If you’re in town, sign up and come by. I’d love to see you.

Now, on to this week’s updates 👇

Last week, I covered EarnIn's expansion into full payroll services for Forbes. The announcement might seem like just another product launch, but it's actually a masterclass in how tech companies can move from feature to platform.

After talking to hundreds of founders through my Forbes platform, I've noticed a pattern: the next generation of tech firms won't win by adding features. They'll win by owning infrastructure.

Here are five key takeaways from EarnIn's playbook that every founder and investor should understand.

1️⃣ Eliminate dependency on someone else’s infrastructure.
The earned wage access market has always been friction-heavy. Workers download an app, connect their bank account, verify employment, and navigate a third-party system just to access money they've already earned.

The vulnerability? Payroll providers like ADP and Gusto could build flexible pay features themselves, cutting earned wage access companies out entirely. By owning the payroll layer, EarnIn controls its own destiny.

If you're building on top of banks, payroll systems, or other platforms, ask yourself: what happens if your infrastructure partner decides to compete with you? If you don't have a good answer, you're one partnership termination away from losing your business.

2️⃣ Turn your users into your sales force.
EarnIn has 27 million users who already trust them with their financial lives. That's not just a user base. It's a potential sales force.

If even 10% of those users work at companies considering new payroll systems, EarnIn suddenly has bottom-up demand that traditional payroll providers simply can't match. Workers telling their employers "we want EarnIn Payroll" is a sales motion that ADP and Paychex don't have access to.

The lesson: Bottom-up enterprise sales (workers demanding tools from employers) is one of the most powerful go-to-market strategies in B2B software. Build consumer love first, then convert advocates into enterprise customers.m to want disruption, but the funding data tells a different story. When a company doesn't fit the existing boxes, most investors walk away. The winners are the ones who create new categories instead of forcing themselves into old ones.

Aunt Flow raised from proptech because they defined their own category.

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3️⃣ Time your move carefully.

EarnIn didn't launch payroll on day one. They built a massive user base, proved the earned wage access model, and established operational credibility first.

As Ram Palaniappan, CEO and Founder of EarnIn, explained: "Paychecks today are digital, and they should work like other digital products: flexible and streaming."

Moving upstream too early kills startups (you burn cash before proving product-market fit). Moving too late lets competitors build moats. The key is waiting until you have the user base, operational credibility, and market validation to make the leap.

4️⃣ Leverage what you’ve already built.
EarnIn's compliance infrastructure for earned wage access (understanding labor laws, wage calculations, and state regulations) translates directly to payroll operations. They're not starting from zero.

The takeaway: Look at what infrastructure you've already built to deliver your core feature. Can those same capabilities be extended to own more of the stack? The best platform plays leverage existing operational muscle rather than building entirely new capabilities.

5️⃣ Recognize when the market is ready.
The payroll market is ripe for disruption right now. Remote work exposed the limitations of legacy systems. Younger workers expect financial flexibility as a baseline, not a perk. According to recent research, 76% of employees across all age groups say earned wage access is important.

The question every founder should ask: Is your market ready for infrastructure disruption, or are you too early? Market timing isn't just about your product. It's about whether customers are frustrated enough with existing solutions to make a switch.

EarnIn isn't just launching a product. They're testing whether fintechs can successfully move from feature to platform. For investors and founders in the space, that's what matters.

If EarnIn succeeds, expect other players (DailyPay, Payactiv, Branch) to follow. If they stumble, it proves that some infrastructure is better left to specialists.

The earned wage access market is projected to grow from $6.2 billion in 2024 to over $61 billion by 2034. The companies that own the infrastructure, not just the features built on top of it, will capture the lion's share of that growth.

One question to ask yourself: Are you building a feature or owning infrastructure?

If your platform partner could cut you off tomorrow, you know the answer.

💡 Found this valuable? Forward this newsletter to a founder who needs to read it.

Some of my favorite conversations start with a cold email from a founder pitching an idea, looking for an intro, or searching for the right partners.

Over the past few months, I’ve been quietly working on something for those founders.

🚀 I’m building an exclusive directory of exceptional builders. Founders who are creating category-defining companies and shaping the future of fintech, health, and work.

A few of the companies I’ve partnered with:
✨ Esusu | unicorn
💫 Cora | unicorn backed by Greenoaks
🔒 Stealth company | recently announced first institutional round led by Anthemis

If you’re building something remarkable and want to be part of this network, I’d love to hear from you.

📩 Reply to this email (or send me a DM) for access.

🔄 Know an exceptional founder building something remarkable? Share this newsletter with them.

🖊️ I wrote about EarnIn’s infrastructure advantage and how its compliance and payroll foundation could shape the next wave of financial infrastructure.
👉 Read on Forbes

💭Last week I asked founders, “Are you vetting your investors as hard as they're vetting you?” and shared a simple framework of 5 questions to help them make better decisions before taking capital.
👉 Upgrade to paid subscriptions for exclusive Q&A, events, and deal sharing

🎧 I released my first Spanish-language episode with Ximena Alemán, founder of Prometeo, to kick off the new Multilingual Money Memories series.
👉 Listen on NPR, Apple, Spotify, or wherever you listen to podcasts

📌Can Anyone Rescue the Trafficked Girls of L.A.’s Figueroa Street?

📌China Pushes to Silence Victims of African Mining Disaster

Just like showing up for swim practice at 6am, this newsletter takes discipline. About 2 hours every week to research, write, and share what matters most in fintech and early-stage investing.

If you're getting value from it, here are 4 ways to support Bear and the Bull:

Till next week,
Ilona

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