There’s “tax season”… and then there’s living in a year-round chess match with the IRS. Most people play checkers. OLarry plays the board, the clock, and the opponent. This week, the AI-powered tax advisory firm out of Marin, California just banked $10 million in Series A funding led by TTV Capital, with Walkabout Ventures and Marin Sonoma Impact Ventures stacking in. This pushes total funding to $14.5 million, serious capital for a business built to make high-net-worth tax headaches someone else’s problem.
The name? A tribute to founder Eric Rachmel’s late father, Larry, who ran a CPA shop the old-school way. The pandemic took Larry, but it also made one thing brutally clear to Eric: the profession was stuck in a pre-cloud, pre-AI time warp. Along with Becky Hobbs, who now runs operations like a finely tuned Formula 1 pit crew, and Corey Heldreth, CPA, whose tax brain could make the IRS sweat, they built OLarry to close the gap between TurboTax simplicity and white glove family office advisory.
It’s not a seasonal hustle. Clients, from entrepreneurs to complex multi-entity owners, pay an all-inclusive annual fee for unlimited, proactive advice. OLarry’s AI isn’t window dressing. It automates onboarding, reads messy financial docs like a savant, flags opportunities in real time, and feeds predictive models that play “what if” with tax scenarios faster than a junior associate can Google the IRS code. And because every byte lives on U.S.-based servers, compliance isn’t a marketing pitch, it’s the default setting.
Growth isn’t just coming from tech. OLarry’s been buying up regional CPA firms, Branton, de Jong & Associates in San Jose and Byrne, Seligman & Co. in San Mateo, folding their expertise into a national, U.S.-based advisory team. Client savings? Try $10K-plus from entity optimization, millions unlocked through C-corp conversions for QSBS, and long-tail wins like cost segregation studies that shave thousands every year for over a decade.
The $10 million now in the bank is headed straight into sharpening the edge: building more proprietary AI models, expanding predictive tax planning, upgrading client experience with agentic AI, scooping up more CPA firms, and hiring the kind of tax talent your accountant wishes they had. With 75% of senior CPAs set to retire within 15 years and a $72 trillion wealth transfer underway, OLarry isn’t chasing the market, it’s building the infrastructure to own it.
