OLarry, an AI-powered tax advisory firm catering to high-net-worth individuals and businesses, has announced the close of a $10m Series A funding round.
The round was led by TTV Capital, with participation from Walkabout Ventures and Marin Sonoma Impact Ventures. This latest investment brings OLarry’s total funding to $14.5m.
Founded to bridge the gap between basic DIY tax software and the expensive, hourly services of elite tax firms, OLarry offers clients all-inclusive annual tax services underpinned by AI. The company aims to democratise proactive tax planning by automating routine workflows, allowing CPAs to focus on delivering personalised, year-round advice to clients with complex financial needs.
The fresh capital will be used to enhance OLarry’s proprietary AI model for tax data classification and extraction, improving how the platform ingests and organises complex financial data. It also plans to expand its predictive scenario planning tools, enabling clients to model tax implications of investment or lifestyle decisions in real time. Additionally, OLarry will introduce an AI-powered client experience layer to streamline communication, education, and interactions between clients and advisors.
To support its rapid growth strategy, OLarry is actively acquiring CPA firms and recruiting top-tier tax professionals. In the past year, it acquired Branton, de Jong & Associates in San Jose and Byrne, Seligman & Co., Inc. in San Mateo. These acquisitions support the firm’s roll-up strategy, allowing it to scale operations while simultaneously training its AI models to automate previously manual tax processes.
OLarry CEO Eric Rachmel said, “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.”
He added, “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.”
TTV Capital partner Lizzie Hartley said, “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. 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.”
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