#United States #TTV Capital #OLarry #AI Tax Planning #Marin, California

OLarry Secures $10 Million Series A Funding

On August 5, 2025, OLarry, a groundbreaking tax advisory firm, announced the successful raising of $10 million in Series A funding. This round was led by TTV Capital, alongside Walkabout Ventures and Marin Sonoma Impact Ventures. With these new investments, OLarry aims to enhance its AI capabilities, acquire CPA practices, and redefine tax planning for high-net-worth individuals and businesses.

A New Era of Tax Advisory

Founded in 2024, OLarry stands out by bridging the gap between traditional DIY tax preparation and high-cost tax advisory services. The firm empowers clients with personalized tax strategies for a flat annual fee, making such services accessible to a broader audience. Unlike conventional tax firms that cater primarily to ultra-high-net-worth clients, OLarry leverages AI to provide unique solutions tailored to each client’s financial needs.

According to Eric Rachmel, Co-founder and CEO of OLarry, the company was built to empower those who require sophisticated tax advice yet find themselves underserved by conventional platforms like TurboTax. He states, "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. OLarry was created for the next generation who needs personalized advice."

The Role of AI in Tax Planning

Central to OLarry’s strategy is the use of artificial intelligence to automate various aspects of tax preparation. This technology streamlines client onboarding, document preparation, and data extraction, thereby allowing Certified Public Accounts (CPAs) to focus on delivering proactive tax advice year-round. Rather than solely relying on manual processes, OLarry’s innovative approach empowers clients to make informed investment decisions based on their tax outcomes.

The demand for personalized tax advice is significant, especially in light of a declining supply of accountants. The firm has witnessed a notable reduction, with a 17% drop in accountants entering the job market, further complicating the landscape for tax preparation services. As OLarry continues to employ a roll-up strategy by acquiring existing CPA practices in California, it has implemented proprietary AI models that automate various manual steps, enhancing efficiency in the tax advisory process.

A Strategic Investment for the Future

TTV Capital is excited to be part of OLarry's innovative approach. Partner Lizzie Hartley highlighted the significant market opportunities available by noting that approximately 75% of partner-level CPAs are poised to retire within the next 10-15 years. As technology evolves, OLarry's disruption of traditional tax services comes at a critical juncture for the industry.

The funding will be allocated toward further developing OLarry’s tax data classification and extraction models, enhancing its ability to manage complex financial information efficiently. Additionally, the investment will assist in building predictive scenario planning tools that help clients optimize their tax situations in real-time.

Looking Ahead

As OLarry pursues strategic acquisitions of CPA firms and recruits top-tier CPAs nationwide, its vision for a modern tax advisory landscape becomes clearer. This approach not only targets growth but also aims to deliver the highest quality of service through its advanced technology and dedicated professionals.

To discover more about OLarry and career opportunities, the firm encourages interested candidates to visit OLarry Careers.

Conclusion

OLarry represents a new frontier in tax advisory services by harnessing the power of AI to provide personalized and accessible solutions for wealth management. With strong backing and innovative strategies, it is poised to reshape the tax advisory landscape for high-net-worth individuals and businesses alike, making professional financial advice more attainable than ever before.