An AI-assisted, year-round tax firm that pairs real CPAs with software - built for founders and high-net-worth families who are too complicated for TurboTax and too sensible for a five-figure invoice.
Here is a mildly annoying fact about taxes: most of the decisions that change your tax bill happen during the year, and most people talk to their accountant after the year is over. You sell the stock, exercise the options, buy the building, take the NFT gain - and then, months later, someone tallies the damage. The advice arrives after the moment to act has passed. This is a bit like getting driving directions once you've already parked.
OLarry's whole proposition is to close that gap. It is a tax firm, staffed by certified public accountants, that sells a flat annual membership instead of billing by the hour. The idea is that if you are not watching a meter, you will actually call your accountant in July, which is when calling your accountant is useful.
The twist - and the reason venture capitalists are involved - is the software. OLarry has built a proprietary AI model that reads and classifies the messy pile of financial documents that every tax return is secretly made of. The AI does the collecting and the sorting. The humans do the strategy. Founder and CEO Eric Rachmel is fairly blunt that the paperwork was never the point of hiring a CPA in the first place.
What OLarry is really selling is a rearrangement of who does what. The tedious 80% goes to the machine; the judgment stays with the person. It is not a robot doing your taxes. It is a CPA with a robot doing the filing so the CPA can think.
Rachmel did not start in taxes. He spent about fifteen years building and investing in venture-backed companies, and before OLarry he founded Brace, a mortgage-servicing software company that raised roughly $30 million and counted two of the top five U.S. servicers as clients. Brace was acquired by Stavvy in 2024.
The pivot to taxes came from something less tidy than a market thesis. His father, a CPA in Southern California, got sick and passed away, and for a stretch Rachmel ran the family practice himself. That is an unusual apprenticeship for a founder - inheriting a working accounting firm - and it is where the shape of OLarry came from: the sense that the expertise was valuable, the workflow was brutal, and the two problems could be separated.
"Proactive tax planning has historically been reserved for the ultra-high-net-worth - those who can afford the most elite tax firms in the country."
If your financial life includes multi-state K-1s, a 1031 exchange, QSBS, equity comp with vesting to time, or income from digital assets, off-the-shelf software tends to give up and elite boutiques tend to send a large bill. OLarry is aimed squarely at that gap.
Ongoing, proactive planning from CPAs on a flat membership - so the advice arrives before the transaction, not after.
Preparation and filing of complex individual and business returns, including multi-state and multi-entity situations.
A proprietary model that ingests, classifies, and structures financial documents - automating the request-and-chase grind.
Equity comp, exercises, and QSBS planning for people whose returns got complicated the day they joined a startup.
GPs, LPs, fund managers, and property operators dealing with K-1s, cost segregation, and 1031 exchanges.
Predictive tools to model tax outcomes across choices like vesting, exercises, and asset sales before you commit.
There is a genuinely strange supply problem coming for tax advice. TTV Capital, which led the Series A, points to an estimate that roughly three-quarters of partner-level CPAs are expected to retire in the next 10 to 15 years. The demand for tax expertise is not going anywhere; the people who supply it are aging out faster than the profession is replacing them.
OLarry's response is two-pronged and slightly unusual. It builds AI to make each remaining CPA more productive - and it buys CPA firms outright, then layers its technology on top. Two acquisitions are already done: Branton, de Jong & Associates in San Jose and Byrne, Seligman & Co. in San Mateo. It is a rollup with a software thesis, which is a more interesting animal than either a pure software startup or a pure accounting rollup.
"We invested in OLarry because of the significant market opportunity: 75% of CPAs at the partner level are expected to retire within the next 10-15 years."
Series A co-investors: Walkabout Ventures · Marin Sonoma Impact Ventures. Use of funds: AI data model, predictive scenario planning, CPA-practice acquisitions.
Eric Rachmel launches a modern, year-round, AI-assisted tax firm in the San Francisco Bay Area.
Rachmel's prior company, mortgage-servicing startup Brace, is bought by Stavvy - clearing the runway for OLarry.
OLarry brings in Branton, de Jong & Associates (San Jose) and Byrne, Seligman & Co. (San Mateo) to add capacity.
TTV Capital leads a $10M round - total funding reaches $14.5M - to fund AI development and further acquisitions.
The brand mascot is a lion named Lara. "Tame Your Taxes" is the tagline, and the lion is doing a lot of the metaphorical work.
The company traces to Rachmel running his late father's CPA practice - a personal detour that turned into a business model.
Before this, Rachmel built Brace, a mortgage-servicing company that raised ~$30M and exited to Stavvy.
The model is built to handle modern situations - NFT and DeFi income, QSBS exemptions, 1031 exchanges, and more.
Reporting compiled from public sources including OLarry, PR Newswire, FinTech Global, Going Concern, Pulse 2.0, and Marin Sonoma Impact Ventures. Figures such as client counts and revenue are company-reported or estimated and approximate.