OLarry, a Marin, California-based AI-powered tax advisory firm, announced on August 5, 2025, that it has raised $10 million in a Series A funding round led by TTV Capital, with participation from Walkabout Ventures and Marin Sonoma Impact Ventures. This brings the company’s total funding to $14.5 million. The funds will enhance OLarry’s AI capabilities and support the acquisition of CPA practices, targeting high-net-worth individuals and businesses with complex financial needs.
OLarry raises $10M in Series A, led by TTV Capital, totaling $14.5M in funding.
Focuses on AI-driven tax planning for high-net-worth individuals and businesses.
Automates onboarding, document prep, and data extraction to free CPAs for strategic advice.
Acquired two CPA firms in San Jose and San Mateo to scale operations.
Addresses a 17% decline in new accountants and 75% CPA partner retirements.
Offers flat-fee, year-round tax advisory for personalized strategies.
OLarry targets the underserved gap between DIY tax tools like TurboTax and expensive, hourly ultra-high-net-worth advisory services. As Eric Rachmel, Co-founder and CEO, stated, “Proactive tax planning has historically been reserved for the ultra-high-net-worth... We built OLarry for the next generation of high-net-worth individuals and businesses, who need personalized tax advice but are underserved by their current tax advisor.” By leveraging AI to automate onboarding, document preparation, and data extraction, OLarry enables CPAs to focus on delivering tailored, year-round tax strategies.
Since its inception in 2024, OLarry has employed a roll-up strategy, acquiring Branton, de Jong & Associates in San Jose and Byrne, Seligman & Co., Inc. in San Mateo. These acquisitions, combined with proprietary AI models for data classification and extraction, streamline historically manual tax processes. The $10M funding will further develop predictive scenario planning tools and enhance client experiences through AI-driven communication, while also supporting the acquisition of CPA firms with up to $6M in revenue.
The tax industry faces a 17% decline in new accountants and a projected 75% retirement rate among CPA partners in the next 10-15 years, creating a ripe opportunity for disruption. Lizzie Hartley, Partner at TTV Capital, noted, “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.” The funding will bolster OLarry’s ability to scale its client base of over 2,000 individuals and 700+ businesses nationwide.
Inspired by the loss of his father, a CPA, during COVID, Eric Rachmel founded OLarry to modernize tax advisory services. The company’s flat-fee model provides year-round access to customized tax planning, empowering clients to make informed investment and life decisions. With a focus on high-net-worth clients, trusts, and estates, OLarry is poised to redefine tax preparation by integrating cutting-edge AI with expert CPA guidance.
OLarry’s Series A funding marks a pivotal step in transforming tax advisory services. By combining AI automation with strategic acquisitions, the company is well-positioned to meet the growing demand for personalized tax planning, delivering value to high-net-worth clients across the U.S.
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.
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