James Olson

Chairman of the Board

James Olson has over 25 years of experience in the retirement plan industry. During that time, he has become an acknowledged leader in his field as the designer of forward-thinking product and service models that have had a significant impact on the retirement plan marketplace.

He has served as Chairman of the Board of Grow Capital since 2019, providing strategic guidance and industry expertise as the company expands its technology-driven solutions across retirement plan administration, recordkeeping, and integrated financial and health platforms.

James began his career in the retirement industry in 1990 as a Client Services Manager for Bank of America Retirement Services while also earning his Series 7 and 65 licenses. His career includes roles with Charles Schwab & Company as Senior Product Manager and Decimal Inc. (now Ubiquity) as Senior Vice President of Strategic Initiatives.

In 2002, Olson became one of the founding partners of ASPire Financial Services. During his tenure, he helped grow the company from a start-up with one employee to 165 employees and $30 million in revenue, earning recognition as one of the Tampa Bay Business Journal’s Fast 50 and a Florida Finalist for Ernst & Young’s Entrepreneur of the Year. As co-founder and Chief Marketing Officer, Olson developed and executed product strategies that established ASPire as a recognized institutional brand, supporting over $6 billion in assets, approximately 175,000 participants, and 5,700 retirement plans.

With a continued focus on innovation in the retirement space, Olson joined Bluff Point Associates in 2013 to help develop the Investment Provider Xchange (IPX) platform—an open-architecture trading solution providing access to mutual funds, annuities, ETFs, and managed portfolios.

In 2024, Olson joined Leafhouse as Executive Vice President of Product, where he is responsible for driving product design and technological advancements.