Marin, CA - Aug 06, 2025 - OLarry, a Marin, California-based AI-powered tax advisory firm founded in 2021, announced, 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. The round brings total funding to $14.5 million, following a $4.5 million seed round in 2023. Serving over 2,000 high-net-worth individuals and 700+ businesses, OLarry’s platform automates client onboarding, document preparation, and data extraction, enabling CPAs to deliver year-round, personalized tax strategies via a flat-fee membership. The funds will enhance its AI tax data model, develop predictive tools, and support CPA firm acquisitions, positioning OLarry to capture a share of the $30 billion tax preparation and advisory market.
The $10 million Series A, led by TTV Capital, a fintech-focused VC with investments in Bill.com and MX, will drive OLarry’s growth. The funds will support:
- AI Development: Enhancing the proprietary tax data classification and extraction model for efficient data processing.
- Predictive Tools: Building real-time scenario planning capabilities to optimize tax outcomes.
- Acquisitions and Hiring: Acquiring regional CPA firms and recruiting top-tier CPAs to expand advisory capacity.
- Client Expansion: Scaling to serve 5,000 clients by 2027, targeting high-net-worth individuals with $1-10 million in assets.
| Funding Round | Amount | Year | Lead Investors | Supporting Investors |
|---|---|---|---|---|
| Seed | $4.5M | 2023 | Not disclosed | Not disclosed |
| Series A | $10M | 2025 | TTV Capital | Walkabout Ventures, Marin Sonoma Impact Ventures |
| Total Raised | $14.5M | – | – | – |
CEO Eric Rachmel stated, “OLarry makes proactive tax planning accessible to high-net-worth clients who are underserved by DIY tools or overcharged by elite firms. Our AI frees CPAs to deliver strategic advice, empowering clients to make smarter financial decisions year-round.”
OLarry’s Technology
OLarry’s platform automates tax advisory workflows, offering:
- AI-Driven Automation: Streamlines onboarding, document preparation, and data extraction, reducing CPA administrative time by 70%.
- Predictive Scenario Planning: In development, this tool will model investment and financial decisions to optimize tax outcomes.
- Agentic AI Experience: Enhances client communication via secure, cloud-based portals.
- Flat-Fee Membership: Provides unlimited access to customized tax strategies, unlike hourly billing models.
The platform integrates with financial systems, ensuring IRS-compliant data security. Clients report 30-50% faster tax preparation and up to 20% reductions in tax liabilities, addressing the needs of high-net-worth individuals, businesses, trusts, and estates in a market projected to grow as CPA retirements accelerate.
Leadership and Expertise
Founded by Eric Rachmel, inspired by his late father’s CPA practice, OLarry is led by a team with expertise in finance and technology. Rachmel, with a venture capital background, drives the vision, alongside co-founders Becky Wong and Corey Patel. Chief Technology Officer Sarah Lin, a 2024 hire from Intuit, enhances platform innovation. The 30-person Marin-based team focuses on disrupting traditional tax services with AI-driven solutions.
Industry Impact and Challenges
The $30 billion tax preparation market faces disruption due to a 17% decline in new accountants and 75% of CPA partners retiring by 2035. OLarry’s AI model addresses this by automating repetitive tasks, enabling CPAs to serve more clients. Its flat-fee model makes personalized tax planning accessible, unlike firms like PwC. Challenges include competition from H&R Block and TaxBit, and data privacy concerns. OLarry mitigates these with secure infrastructure, transparent pricing, and a focus on underserved high-net-worth clients.
Stakeholder Perspectives
Lizzie Hartley of TTV Capital said, “OLarry is building an AI-powered tax advisory business at the right time, streamlining inefficiencies and enabling proactive advice.” A client noted, “OLarry’s platform simplified our complex tax situation, saving us time and money with clear guidance.”
Future Outlook
OLarry plans to launch its predictive scenario planning tool in Q2 2026 and acquire two CPA firms by 2027. Targeting 5,000 clients by 2028, the company will partner with wealth management firms and fintechs to drive growth, capitalizing on the evolving tax advisory market.
