OLarry Uses AI and Acquisitions to Modernize One of Tech’s Most Resistant Industries

SAN MATEO, Calif., Dec. 19, 2025 /PRNewswire/ — While much of the accounting industry is still experimenting with AI demos and pilot programs, OLarry is already running core tax workflows on production systems and growing fast as a result.

OLarry, a modern strategic tax platform, closed 2025 with more than 3,000 customers, 40+ employees, and record growth across high-net-worth households, operating businesses, and institutional investors. The company’s expansion signals a broader shift underway in tax and accounting, one of the largest professional services markets yet to meaningfully modernize.

Over the past year, OLarry expanded aggressively beyond traditional individual and business tax preparation into real estate, private equity, venture capital, hedge funds, and family offices, segments where tax errors are costly and traditional firms struggle to scale. To support that growth, the company invested heavily in senior talent and launched proprietary AI systems that automate document ingestion, classification, and structured data extraction directly from tax forms.

“Private-capital clients want a tax partner who moves quickly, communicates clearly, and understands how decisions today affect outcomes several years down the line,” said Eric Rachmel, the firm’s co-founder and CEO. “That expectation is reshaping what a modern tax company looks like.”

Unlike generic automation tools, OLarry’s AI is designed specifically for the complexities of tax, enabling CPAs to spend less time on manual data handling and more time advising clients on structure, strategy, and risk. This allows the firm to operate on a flat-fee pricing model and emphasizes transparency around scope and deliverables, which aligns incentives more closely with clients.

OLarry also used acquisitions to accelerate its growth. During the year, it acquired Rossi & Co. Accountancy and Pelzner & Associates, folding both practices into its platform. Clients from the acquired firms now have access to expanded advisory teams and the company’s technology infrastructure, while maintaining continuity with existing relationships.

Looking ahead to 2026, OLarry plans to continue scaling its platform at the intersection of elite tax expertise and applied AI. “Tax is too important and too expensive to stay analog,” Rachmel added. “We think the next generation of tax advisory will look a lot more like software companies, even if the output is advice.”

About OLarry 
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 3,000+ 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. To learn more, visit https://olarry.com/.

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SOURCE OLarry