Why We Invested in Carefull
Over the next two decades, roughly $84 trillion will pass from one generation to the next — the largest wealth transfer in history. Baby Boomers alone will hand down an estimated $53 trillion of it. And the clock has started: on January 1, 2026, the oldest Boomers turned 80, and the number of people moving through the most financially vulnerable years of their lives is climbing fast.
We’ve spent a lot of time at Springbank thinking about what this moment actually requires. Most of the conversation about the wealth transfer focuses on the investing side — who manages the assets once they move. We’ve been more interested in a quieter, harder problem: the work of getting an aging parent’s financial life in order before a crisis. It’s the textbook “important but never urgent” task. More than 40% of Boomers don’t have a will. Far more have never shared a password, consolidated an account, or given an adult child any visibility into the bills, the subscriptions, the slow drift of a financial life that’s getting harder to manage alone. Nobody wants to have the conversation. So it doesn’t happen — until something goes wrong.
That gap is expensive. Older adults hold roughly two-thirds of all U.S. deposits, and elder fraud and money mistakes now drain an estimated $64 billion a year. Behind that number are millions of families who find out too late.
This is the problem Carefull was built to solve — and it’s why we invested so early.
So, why Carefull?
In 2021, what we were really betting on was a thesis and a team.
The thesis was about distribution. We believed — and still believe — that a product like this can’t win as a direct-to-consumer app. People feel the pain, but they won’t go buy a subscription to manage their dad’s checking account. The only way it works is through the institutions families already trust: their bank, their credit union, their financial advisor. Get the distribution right, support it relentlessly, and you become infrastructure. That was the bet.
The team was the other half. Todd Rovak spent his career helping the largest banks and brokers design and launch new products — he understood, better than almost anyone, how to get something adopted inside a big financial institution. Max Goldman is the product builder who’d already taken a company from zero to one and sold it to Google. Together they’d been circling this idea since 2015. It was, frankly, an unsexy category that most founders ignored. We thought that was exactly the point.
Five years later, Carefull is now the financial safety platform embedded across banks, credit unions, and major advisor networks — including Osaic and, as the team announces this week, Edward Jones. Each member gets continuous account monitoring, fraud and scam detection, secure family collaboration, and $1 million in identity theft insurance. In June 2026, Javelin Strategy & Research named Carefull a category leader for user experience in identity protection — the kind of recognition that matters enormously when your users are often navigating this technology on behalf of someone they love.
And the company is no longer just catching problems — it’s predicting them. Last fall Carefull launched GreyMatter, a proprietary AI engine trained on millions of transactions to spot the early signals that traditional fraud systems miss: not just scams, but the behavioral patterns that can signal cognitive decline or exploitation before real damage is done. The team is using it to define a whole new category they call “longevity finance” — a recognition that as the country ages, protecting people’s money is going to require an entirely new layer of the financial stack.
I was reminded of how big this is on a recent panel with Max during New York FinTech Week, where we talked about how fraud and social engineering are growing more sophisticated at the exact moment trillions of dollars start moving between generations. Families don’t just need advice. They need a multi-player platform that offers protection, transparency, and tools to make the hardest financial conversations a little easier to have.
That’s the work Carefull is doing. We were lucky to back Todd, Max, and the team early, and we couldn’t be more excited about what comes next.
— Courtney Leimkuhler, Springbank Collective
