The firm’s expansion reflects a specific shift in market demand from families managing multifaceted financial structures, including trusts, diverse business entities, and international property holdings. By leveraging AI to handle document preparation and routine onboarding, OLarry aims to liberate its senior staff to focus on complex tax strategy and proactive planning.
OLarry Scales Tax Advisory Services for High-Net-Worth Households
San Mateo-based OLarry has secured over 2,000 new high-net-worth clients in the past year, prompting an aggressive recruitment drive for elite tax advisors. The firm, which targets individuals with an average net worth exceeding $10 million, is pivoting away from seasonal preparation toward year-round strategic financial oversight.

COO and co-founder Becky Hobbs noted that the recent growth validates the need for a non-transactional approach to wealth management. To support this trajectory, the company is actively poaching talent from major national and regional accounting firms. According to CAO and co-founder Corey Heldreth, the objective is to provide clients with a partner capable of navigating intricate financial landscapes before major decisions are finalized, rather than merely filing paperwork after the fact.




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