Runbook: Waldo SAFE 2026
Disclosure: I’m an angel investor in Waldo, and the offer below for Interchange subscribers is a promotion I put together with the company, through a link that credits sign-ups to me. This is my own opinion, not investment advice. The promo terms are set by Waldo, and you should do your own diligence before moving money. The promo: If you sign up for Waldo and mention “Interchange,” Waldo will do a 1% match on deposits up to $5,000.
Welcome to Runbook, a new Interchange series. Runbooks are investment memos, founder Q&As, roundtables and other direct interactions with what founders and operators are doing and how they do it. This post is a Runbook memo, the investment memo I write for myself and our Chime alumni investment syndicate, 2 Days Early, before I put money into a deal. Most investment write-ups are retrospectives: polished after the outcome is known, once the story is safe to tell. Runbook memos are the opposite. It’s the real pre-investment thinking, open questions and honest risks left in, so you see the deal the way I saw it before I know how it will turn out.
First up is Waldo, an AI-powered treasury platform. How I got here: I’ve known Ryan, the founder, since he ran his previous startup, Gatsby, when my prior company Hudson River Trading, invested in one of his rounds. When he was starting up Waldo, it became clear that I needed to invest and later, Ryan g
ave me his blessing to write about the company publicly, so here’s our investment memo.
The promo: If you sign up for Waldo and mention “Interchange,” Waldo will do a 1% match on deposits up to $5,000.
The Problem
Businesses are sitting on more than $5T in cash, and the overwhelming majority of it is parked somewhere that earns almost nothing: zero-yield checking, low-yield savings, or a narrow, limited-use treasury product. The tools that are supposed to fix this are their own kind of pain. Because they’re all banks (e.g. Mercury, Ramp, Brex, etc.) They demand $250K minimum balances, offer only one or two investment options, run on legacy UX, and, the real killer, they force you to switch your primary bank just to get access. So the status quo is a lot of idle cash and a set of “solutions” that ask for too much and give back too little. No one to date has built a “robo-advisor” for sub-enterprise businesses to manage their cash like a Fortune 500.
The Solution
Waldo is an AI-powered treasury management platform that helps businesses maximize yield, manage risk, and tailor cash allocation to their actual liquidity needs, risk tolerance, and operating profile without switching banks. That last part is the whole point.
What sets it apart is a stack of things incumbents don’t put together: more than 100 portfolios to choose from (versus one or two at the legacy players), a dedicated human advisor paired with agentic AI guidance, up to $75M of SIPC coverage (versus the usual $250K of FDIC), and stablecoin-native cash management. It monetizes the way you’d want: a nominal fee on AUM depending on account size, so Waldo makes more when it’s actually managing more of your money.
I used the product myself before writing a check and the onboarding was genuinely personalized, a real human approved my account, and account linking ran cleanly through Plaid. It felt like a product built by people who care about the experience, not a compliance form with a logo. The founder line that stuck with me was that it’s wild how useful AI is when you’re running an RIA and you can feel that leverage in how much a tiny team is able to deliver. You get an AI and a human that have real-time understanding of your specific business, proactive, dynamic responses and always-on guidance that doesn’t stop after 5pm on the weekends, while still having a human on-hand for the tricky issues or ones where you need human presence.
Reminder: If you sign up for Waldo and mention “Interchange,” Waldo will do a 1% match on deposits up to $5,000.
The Opportunity
The target here is the $5T to $10T of U.S. corporate cash that’s slowly moving beyond checking and savings toward higher-yield, more flexible treasury solutions. Waldo’s wedge is simple to say and hard to build: better yield, broader product breadth, and more control, all without making the customer change their primary bank relationship. On distribution, they’re pairing direct customer acquisition with bank distribution through Grasshopper, which opens the door to roughly 6,000 corporate banking customers. Direct plus a bank channel is exactly the combination I want to see at this stage.
The Team
This is a repeat team that is impressive. Ryan Belanger-Saleh and Jeff Myers have built and sold a company together before Waldo. They co-founded Gatsby, a commission-free options trading app, grew the team to about 40 people, and sold it to eToro in 2022. Taking a regulated consumer fintech from zero to acquisition is exactly the operating experience I want backing a treasury product.
Today they’re lean again: a small team, mostly engineers, with plenty of cash on hand and about two years of runway. That capital efficiency matters here. A small, agentic team that ships and keeps costs disciplined has room to compound before it has to raise on someone else’s terms.
The Traction
Waldo launched in April 2026 with about $240K in AUM and reached $41M in net new AUM in roughly three months. That’s 170x growth, with deposits still accelerating and genuine demand for portfolios that carry investment-grade fixed income exposure. After a recent Grasshopper PR push, they added more than dozens of new sign-ups and millions of scheduled deposits, and last I checked they were about to cross $50M in AUM.
The execution around the growth is just as important as the growth itself: a live Grasshopper partnership, SOC 2 certification, RIA approval, registered reps, and a finalized FINRA broker-dealer application. In a regulated business, that scaffolding is the difference between a fast start and a durable one.
The Round
They’re raising $2M on a SAFE at a $25M cap, earmarked for customer acquisition and marketing to keep the growth curve going. It’s a massive markup to the last fundraise, which tracks given the traction since then.
Interspace Ventures x 2 Days Early Is In
Interspace Ventures and the 2 Days Early operator syndicate are both in on Waldo’s SAFE among a number of angel investors and operators. Cash management is finally a real product again. Rates make yield matter in a way it didn’t for most of the last decade, and the winning wedge is refreshingly simple: don’t make me switch banks. A tiny, capital-efficient team is compounding fast, the regulatory scaffolding is real rather than aspirational, and the AI-plus-human-advisor model fits the moment exactly; enough automation to serve a hundred portfolios, enough human judgment to earn trust with someone’s operating cash.
The risks: this is a regulatory-heavy business, it’s competitive, and it’s still early. The traction curve has to hold, and net new AUM has to keep converting into durable balances rather than a burst that flattens out. Concentrating conviction in something this young only works if the execution stays this sharp.
For Interchange subscribers: if you want to try Waldo, they’re running a promo for this audience. It’s a 1% match on every deposit, up to $5,000, and it applies to all your deposits, not just the first. It’s available for a limited time. Just mention Interchange to get the match. If you’ve got idle cash sitting in a zero-yield account, this is a low-friction way to test the product and put that 1% to work.