OLarry, an AI-driven tax firm, has secured USD 10 million in a Series A funding round. This investment was led by TTV Capital and joined by Walkabout Ventures and Marin Sonoma Impact Ventures, raising the company’s valuation to USD 14.5 million.

With these funds, OLarry plans to enhance its service offerings, bridging the gap between do-it-yourself (DIY) tax preparation and hourly tax advisory services. The aim is to provide clients with personalized tax strategies under an all-inclusive annual fee model.

AI-Driven Tax Advisory

OLarry utilizes AI technology to automate various aspects of client onboarding, document preparation, and data extraction. This allows Certified Public Accountants (CPAs) to focus more on offering proactive advice, especially for clients with complex financial situations, rather than spending time on repetitive tasks.

Traditionally, proactive tax planning has been available primarily to ultra-high-net-worth individuals who could afford the most elite tax advisory services. OLarry’s goal is to serve a broader client base that requires personalized advice but may be underserved by traditional tax advisors. By offering year-round tax advice, OLarry helps its clients make smarter financial decisions and investments.

This strategic move follows OLarry’s recent acquisitions of Branton, de Jong & Associates in San Jose and Byrne, Seligman & Co., Inc. in San Mateo. The firm is also training its proprietary AI models to streamline data classification, facilitate fast research, and automate manual tax processes.

TTV Capital’s investment in OLarry was driven by recognizing a market opportunity. With 75% of CPAs at the partner level expected to retire within the next 15 years, and considering significant advancements in AI that can improve tax preparation and filing, the company believes OLarry will enhance efficiency, reduce manual work, and adopt a proactive approach to tax advisory services.

The recently acquired funds will be used by OLarry to develop its proprietary tax data classification and extraction model further. Additionally, these resources will support the advancement of predictive scenario planning tools that can provide real-time optimization of tax outcomes for clients. The company also plans to improve client interactions through a more agency-like AI-powered experience.