October 6th, 2025
Just Pool, It’s Cleaner
In the life of a startup, you have complete control over two moments: when you start and when you give up. Those might be the only two.
Exactly two years ago, I wrote a long post about shutting down Braid, a consumer payments company I’d worked on from 2019-2023. I wrote it because I was looking for closure, but didn’t get any. I wrote that post for myself, and 175,000 people read it. I got a wave of emails, DMs, and texts from strangers, fintech friends, and many others. The response shocked me.
It led to two years of windy rebuilding, and I’m delighted to share that we’re running it back. The new company is called Pool. It’s a new product, and the soul is the same: a multi-user financial account* for consumers, designed to make sharing, managing and spending money together easy. You can check out the website, read the company post here, and read Alex Konrad’s coverage in Upstarts here.
After Braid, I was unemployed for a while, so I had a lot of time to think. And the biggest observation I had during that period was shuttering a company and giving up were not the same thing. Sure, I wallowed, but my self-pity quickly started to bore me. Laying on a concrete floor listening to Sabotage lost its appeal. And I couldn’t shake the feeling that Braid was still fundamentally a good idea. It took me years to piece this one insight together: failure is mostly in our heads, but giving up is entirely within our control.
And I wasn’t ready to give up yet.
*Pool is a financial technology platform and not a bank. Bank products and services are provided by First Internet Bank, Member FDIC.
REVENGE IS CLEAN FUEL
All that time spent reflecting wasn’t always a great way to spend the day. It was easy to fall into an endless doom loop: searching for a clean, pithy answer to “why did this happen?”, and never finding one.
It all felt like cope or contrition.
And I was mad. If surrender was a state of mind, then I’d capitulated to it. And worse, I wasn’t fighting some war, or defending democracy, or saving innocent lives. This was the cushy world of tech startups. I was just…soft.
I realized during this period that my understanding of revenge was all wrong. I’d thought the best revenge was about getting back at the other party. An old boss, an ex, a former best friend, a business deal that went sideways. The plot of Kill Bill, essentially.
But the best revenge isn’t about the other party at all. It’s about giving yourself the chance to behave differently in an identical setting. To put a different version of you back in the same situation with a fresh chance to get it right.
The best revenge is a clean do-over.
And I didn’t need the blessing of some unpredictable external force to give myself that. I could simply wake up and get back to work. Once I thought about it this way, I felt free. My friend Toby said, “revenge is clean fuel” and at first, I didn’t understand what he meant. But now I do.
ENTER THE ASYLUM
It’s near impossible to build a consumer payments startup alone. The requirements are massive. For this product, we’d need a new partner bank, updated software, sharp market demand, a new name and millions of dollars in the bank. And that was just to launch.
After working in startups for a while, I take the “100 no’s” approach to most things. I’ll only admit something might be a bad idea only after 100 people say no. But until then, I will keep at it. So I reached out first to Nick Chirls at Notation Capital / Asylum Ventures. We met in 2012, and he’d invested in both Braid and Grand St. prior (sold to Etsy in 2014). He is one of the best investors I know, and many others think the same. I knew he’d tell me the truth about how this idea would sound to someone who wasn’t me. When he offered to lead the round, I was shocked. I’d prepared myself for ~99 more conversations, and instead, we were moving after the very first one.
Two years is an eternity in startup years, and so much happened between October 2023 and October 2025. At Pool, we’re partnering with an amazing partner bank that works with legendary fintech companies like Ramp and Increase. Consumer fintech stocks came roaring back to life, and Robinhood is at an all-time-high. Chime and Klarna IPO’ed. The political landscape in the United States has changed dramatically.
But the challenges to building a multi-user product are still around. No one had come along and built it yet. The technical, regulatory, consumer and fraud challenges are fierce and unpleasant. Luckily, we’ve brought an arsenal with us this time around: years of customer insights, a Box account full of compliance documents, a customer list and a laundry list of mistakes we won’t make again. This time, we’ll make different mistakes. Startups don’t often get a second chance, so I feel extremely lucky. Getting to try again is a privilege.
THE POOL PARTY
Consumers are still starved for new financial tools, and they still deserve better. I’m angry about the shutdown, sure, but the problem still pulls at me. I still feel the burn of it, the same way I did two years ago or six and a half years ago when we started. It feels like no time has passed.
So, why do it again? Other than I can’t think about anything else, it feels much simpler this time. It’s a useful product that solves a real problem for millions of potential customers. It’s a slog to build it, but we believe it should exist in the world. So we’re willing to take the risk.
To me, the crux of the problem is this: “social payments” products don’t support genuine co-ownership and ongoing money management. They support one-time payments, fundraising campaigns and receipt tracking. But the owner of the funds is always just one person. To achieve a true multiplayer experience, you’re stuck with either a joint account (many pain points for consumers) or a business account (where you need…a business).
We designed Pool as a brand-new multiplayer product from scratch. It’s a web app now, instead of a mobile app, and designed to handle a more robust set of permissions and controls. We grew up a bit, and so did the product. But we still live by the same philosophy: together we’re rich.
At Braid we’d called what we’d developed a money pool, because it felt clear and obvious. So when we were thinking about what to name this new product, there was only one name that felt right. It had to be Pool. Just Pool.
We’re still on the same unpredictable path and no company ever reaches the point where it gets to control what happens next. But we’re doing this not because success is guaranteed. We’re doing it because improving consumer options and improving our financial system are worthwhile undertakings.
We know it’s hard work with low odds. But isn’t that what makes it all worth it?
And today, we get to declare that we’ve started. We’re already running transactions in production. We’re moving real money for real people. And for me, that means we’ve already won.
We wanted to bring it back and we did. Today, we get our revenge.
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Thank you to everyone who read a draft of this post. Pool is free to use and you can sign up for our waitlist here: https://poolmoney.com. We’d love to hear from you about how you’d like to use Pool. Please email us: hello@poolmoney.com. And if you are a former Braid user, email us and we’ll bump you to the front of our waitlist.