OLarry, an AI-powered tax firm for high-net-worth individuals and businesses, has raised $10 million in a Series A funding round. The round was led by TTV Capital, with participation from Walkabout Ventures and Marin Sonoma Impact Ventures. This brings OLarry’s total funding to $14.5 million.
OLarry provides personalized tax strategies for an all-inclusive annual fee. It uses AI to automate client onboarding, document preparation, and data extraction. This allows CPAs to focus on giving proactive advice to clients with complex finances.
“Proactive tax planning has been only for the ultra-wealthy who can afford top tax firms,” said Eric Rachmel, Co-founder and CEO of OLarry. “We built OLarry for the next generation of high-net-worth clients who need personalized advice but are underserved by TurboTax or their current advisor.”
Demand for personalized tax advice is growing, while the number of accountants is decreasing by 17%. At the same time, AI is getting more sophisticated.
Investing in personalized tax automation
This means the tax preparation industry is ready for disruption. Since starting in 2024, OLarry has been growing fast by buying firms like Branton, de Jong & Associates and Byrne, Seligman & Co., Inc.
The company has been training its AI models to automate document requests, classify and extract data, and enable quick research. This brings automation to the usually manual tax process. “We invested in OLarry because of the huge market opportunity,” said Lizzie Hartley, Partner at TTV Capital.
“75% of partner-level CPAs will retire in the next 10-15 years, and AI can now streamline tax prep in ways not possible a few years ago.”
OLarry will use the new funding to further develop its tax data classification and extraction model. This will make it more efficient to take in and structure complex financial data. The company also plans to expand its predictive scenario planning tools.
These will let clients model the tax impacts of investment or lifestyle choices in real-time. OLarry will also add an AI-powered client experience layer to improve communication and interactions between clients and advisors.