Round led by TTV Capital will expand company’s AI capabilities and fund acquisition of CPA practices

MARIN, Calif., Aug. 5, 2025 /PRNewswire/ — OLarry, an AI-powered tax firm for the next generation of high-net-worth individuals and businesses, today announced that it has raised a $10 million Series A round led by TTV Capital and joined by Walkabout Ventures and Marin Sonoma Impact Ventures, bringing the company’s total funding to $14.5 million. OLarry bridges the gap between DIY tax preparation and ultra-high-net-worth, hourly tax advisory, empowering thousands of clients to gain access to personalized tax strategies for an all-inclusive annual fee. With AI at its core, OLarry automates client onboarding, document preparation, and data extraction, enabling CPAs to focus on what they do best: provide proactive advice to clients with complex financial situations.

“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. We built OLarry for the next generation of high-net-worth individuals and businesses, who need personalized tax advice but are underserved by TurboTax or their current tax advisor,” said Eric Rachmel, Co-founder and CEO of OLarry. “OLarry uses AI to streamline workflows, freeing up CPAs to focus on what they do best: provide holistic tax advice year-round, not just during tax season. In doing so, we enable our clients to make smarter investment and life decisions because they can understand how it will impact their taxes.”

The combination of increased demand for personalized tax advice, coupled with a 17% decrease in accountants entering the job market and increasingly sophisticated AI, means that tax preparation services are ripe for disruption. Since OLarry’s inception in 2024, the company has deployed a roll-up strategy to rapidly scale its business – acquiring Branton, de Jong & Associates in San Jose and Byrne, Seligman & Co., Inc. in San Mateo – while training its proprietary AI models to automate document requests, classify and extract data, and enable rapid research, bringing automation to the historically manual tax process.

“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, and dramatic improvements in AI can streamline tax preparation and filing in a way that wasn’t possible a few years ago,” said Lizzie Hartley, Partner at TTV Capital. “OLarry is building an AI-powered tax advisory business at exactly the right time, in the right way – by improving inefficiencies, eliminating manual work, and taking a proactive approach to tax advisory services. We are proud to support Eric, Becky, Corey, and the entire OLarry team as they continue to onboard new clients and scale the business.”

OLarry will use its new infusion of capital to continue building out the company’s proprietary tax data classification and extraction model, enabling more efficient ingestion and structuring of complex financial data. Funds will also advance the development of predictive scenario planning tools to help clients optimize tax outcomes in real-time, as well as create an agentic, AI-powered client experience to support seamless communication, education, and advisor interactions. OLarry is pursuing strategic CPA firm acquisitions and recruiting nationally recognized, top-tier CPAs to further strengthen its advisory practice. To learn more about careers at OLarry, visit https://olarry.com/careers.

About OLarry
OLarry is a modern, AI-powered tax advisory firm for high-net-worth individuals, businesses, trusts, and estates with complex financial situations. Serving more than 2,000 clients and 700+ businesses across the United States, OLarry uses AI to automate client onboarding and document preparation, enabling CPAs to focus on tax strategy and advice. With a flat-fee membership, OLarry clients have year-round access to customized tax planning supported by modern technology. To learn more, visit https://olarry.com/.

SOURCE OLarry