They Sold Their First Fintech Company. Now They’re Using AI to Bring Treasury Tools to More Businesses.

When Ryan Belanger-Saleh and Jeff Myers sold Gatsby in 2022, they thought they were done solving one of finance’s hardest problems. Gatsby had helped modernize options investing for a new generation of retail investors, but after joining a much larger financial institution, the pair noticed something unexpected: while consumer investing had become dramatically more sophisticated, business treasury had barely changed.

Many companies continue to hold substantial cash balances in checking or savings accounts, in part because liquidity management can still involve manual, fragmented, and institution-dependent processes.

That realization led Belanger-Saleh and Myers to start Waldo.ai. Rather than building another bank, they set out to create an AI-native treasury platform that gives growing businesses access to cash-management capabilities traditionally reserved for Fortune 500 finance departments. Their belief is simple: every company should have an intelligent treasury function, regardless of whether it has two employees or 2,000.

Make expertise part of the product

Waldo’s thesis is that the biggest opportunity isn’t simply helping companies buy treasury bills or money market funds. It’s reducing the cognitive overhead required to make treasury decisions in the first place.

A business can have access to financial products and still face a difficult question about how to use them. Founders and finance teams have to consider liquidity, cash-flow needs, and the tradeoffs involved in putting operating cash to work. Larger companies can dedicate treasury professionals to those decisions. Smaller businesses often cannot.

Instead of expecting users to become fixed-income experts, Waldo uses AI to explain portfolio tradeoffs, answer questions conversationally, recommend appropriate liquidity strategies, and guide customers toward decisions that match their cash-flow needs. Treasury becomes less about navigating financial products and more about describing business objectives.

That focus gives Waldo a more specific problem to solve than simply offering another place to move idle cash. The product is built around making specialized treasury knowledge easier to use.

Use AI where the decision is difficult

Artificial intelligence has increasingly moved into liquidity management, payments, compliance, and decision support inside banks and treasury organizations. Waldo applies it to the point where business owners and finance teams have to interpret their options.

Rather than treating AI as a standalone feature, the platform uses it to help users understand what different treasury decisions mean for the business. A recommendation is most helpful when the customer can see how it connects to the company’s liquidity needs and the role cash plays in everyday operations.

That approach also reflects a larger change in commercial banking. Banks have traditionally competed on products such as accounts, payments, and lending. Treasury increasingly involves connecting deposits, investments, forecasting, payments, and liquidity into a system that helps determine what should happen next.

For Waldo, the value of AI rests in making that complexity easier to manage. The goal is not another fintech dashboard, but a treasury experience that asks less specialized financial knowledge from the customer.

Build into the systems that customers already use

Belanger-Saleh and Myers are also taking an approach that does not require Waldo to replace the financial institutions businesses already use.

The company partners with banks to embed treasury capabilities directly into their digital banking experiences, allowing business customers to optimize idle cash without leaving the bank’s ecosystem. The model has already led to partnerships with digital-first banks such as Grasshopper Bank.

That arrangement can allow businesses to access more sophisticated treasury capabilities through an existing banking relationship. Banks, meanwhile, can deepen customer relationships and retain deposits that might otherwise migrate to standalone treasury or investment platforms.

The decision fits the larger idea behind Waldo. Belanger-Saleh and Myers are trying to make capabilities that have historically required larger finance departments available to a much broader group of businesses without asking those businesses to recreate the infrastructure or expertise that Fortune 500 companies already have.

Their second fintech grew from noticing how much of that gap still remained. Consumer investing had become easier to access and navigate, while business treasury continued to demand specialized knowledge and manual decision-making. Waldo is built on the belief that AI can help close that gap—making more sophisticated cash management increasingly practical for companies that may not have a dedicated treasury team.

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