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Navigating Financial Decisions with Clarity and Confidence

At Sidecar Asset Management, we aim to guide clients in making financial decisions with clarity and confidence. We provide client-first advice, resources, and personalized strategies tailored to individual needs. With a focus on long-term relationships and strategic planning, we are committed to delivering the highest level of service and care. Our goal is to provide the guidance clients need to make informed decisions and move forward with confidence.

Our Services

We provide financial guidance tailored to individuals' evolving needs. Our approach highlights support that aligns with personal goals and priorities while considering various financial factors and adjustments over time.

Retirement Planning

We create customized strategies that assist clients in retirement planning, taking into account long-term goals, income, and lifestyle choices.

Business Planning

We provide guidance to help business owners manage ownership changes, organize finances, and explore growth opportunities to support business health.

Estate Planning

We assist clients in managing and distributing assets according to their wishes.

Investments

We create personalized investment strategies tailored to each individual, focusing on growth optimization and risk management.

Portfolio Management

We help manage investment portfolios, focusing on balancing risk and reward and supporting both short-term and long-term financial goals.

Risk Management

We develop strategies to identify, assess, and address financial risks, with the goal of protecting assets and supporting financial stability.

Our Team

At Sidecar Asset Management, we are committed to helping clients navigate financial planning with structure and thoughtful guidance, adapting as circumstances evolve. The name Sidecar reflects this philosophy—acting as a trusted guide while allowing clients to maintain control. Just as a sidecar provides support and balance while the driver steers the path forward, we offer insight, perspective, and strategic planning to assist clients in confidently moving forward.

Founder, Wealth Advisor

Aaron Massey

Aaron is a financial advisor with over 25 years of experience and a background in banking, investments, and wealth management. He believes financial planning is more than managing assets—it’s about helping people bring structure and clarity to their most important decisions. Whether planning for retirement, structuring an inheritance, or navigating a business transition, Aaron helps clients think strategically and move forward with confidence.

As the founder of Sidecar Asset Management, Aaron takes a client-first approach that prioritizes transparency, long-term planning, and personalized service. He’s committed to understanding each client’s unique situation and providing thoughtful, flexible guidance rooted in trust and experience.

Aaron’s path began with a childhood spent in a military family, moving between Texas, Italy, Georgia, and Washington before eventually settling in Oklahoma. Those early experiences taught him adaptability, resilience, and the value of a strong foundation—both in life and in finances. He earned his BBA in Finance from the University of Oklahoma.

Aaron has held leadership roles with several Tulsa-based organizations, including: Trustee, Indian Nations Council, Boy Scouts of America, Pack Master/Cub Scout Den Leader, Holland Hall, Trustee, Tulsa Community College Foundation, Chairman, Salvation Army Boys & Girls Club of Metro Tulsa, Member, Seedstep Angels, Vice President of Finance & Board Member of Iron Gate, Board Member of Tulsa Global Alliance, and Trustee, at Monte Cassino School.

Outside of work, Aaron enjoys spending time with his wife, Erika, and their three boys, Henry, Leon, and Bode. He also enjoys golf, tennis, traveling, weekends at the lake, and skiing (he likes to joke that he might be the best skier in Oklahoma!). He’s coached youth sports and stays involved in scouting and mentorship throughout the Tulsa community.

Chief Operating Officer

Erika Massey

Erika oversees administrative functions, vendor relationships, and office technology, ensuring that the banking environment remains secure, efficient, and customer-focused.

Prior to joining Sidecar Asset Management, Erika worked at the Bank of Oklahoma as a Trust Officer in the Private Bank, where she developed expertise in family wealth management, financial documentation, and regulatory compliance.

Beyond her professional responsibilities, Erika is deeply committed to philanthropy and community service. She has volunteered her time through several organizations in the Tulsa area, including Oklahoma Project Woman (Board Member), Foundation for Excellence (Trustee), March of Dimes (Event Chair), Tulsa Symphony Orchestra (Board Member), Town & Country School (Event Chair and Board Member), YWCA Tulsa (Board Member), and Holland Hall School (Alumni Board Member).

Business Support

Will Brand, CRCP®

Chief Compliance Officer

Ryan Geschke

Managing Director, Investments & Trading

Erin Corbett

Chief Operating Officer

Jenny Kurz

Director of Marketing

Lauren Lehman, CFA®, CFP®

Head of Portfolio Management

Arianna Rodriguez, CIMA®

Senior Portfolio Manager

Resource Partners

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