Inventive

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Independent

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Personable

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Inventive · Independent · Personable ·

Jim Cheadle

President and Chief Investment Officer

Prior to founding Ponderosa Investment Group, LLC in 2006, Mr. Cheadle built an extensive career in investment management and institutional consulting.

Mr. Cheadle previously served as Vice President and Senior Portfolio Manager at HighMark Capital Management in Portland, Oregon, the investment division of Union Bank of California. In that role, he provided investment management and portfolio guidance to individuals and businesses throughout the Pacific Northwest.

Prior to HighMark Capital Management, Mr. Cheadle served as Chief Investment Officer of Copper Mountain Trust in Portland, Oregon, where he was responsible for overseeing the firm's investment activities and leading its investment management team. Prior to this, he held the position of Senior Investment Consultant. As a CIO he was responsible for more than $500 million in managed assets.

Earlier in his career, Mr. Cheadle worked as a Consultant and Research Associate with CTC Consulting, Inc., where he focused on investment research and alternative investments.

Mr. Cheadle brings more than two decades of experience in investment management, financial planning, portfolio construction, and investment research. His professional experience spans a wide range of market environments and client circumstances, providing a strong foundation for helping individuals and families develop the knowledge and confidence necessary to make informed financial decisions.

Outside of his professional career, Jim is a lifelong native of the Pacific Northwest. Born and raised in John Day, Oregon, he now calls Portland home but continues to have a deep connection to his hometown and enjoys spending time in John Day and throughout eastern Oregon whenever possible. A proud husband and father of three boys, Jim enjoys spending time with his family and has previously coached youth football, where he valued the opportunity to mentor and encourage young people. He is also an avid outdoorsman who particularly enjoys hunting elk and remains actively involved in his church and local community.

Mr. Cheadle holds a Bachelor of Science in Business Administration with a concentration in Finance and Investments from Oregon State University.

Maria Cheadle

Bookkeeper & Office Manager

With over 20 years of experience in financial management and operations, Maria plays a key role in keeping Ponderosa Investment Group, LLC running smoothly. She combines precision, efficiency, and a talent for improving systems to ensure the firm’s day-to-day functions are seamless and effective.

Maria is known for her integrity, reliability, and calm problem-solving approach—qualities that make her a trusted partner and steady presence within the team. Her strong Christian faith is at the heart of how she leads and serves, guiding her with purpose, humility, and a commitment to doing what’s right.

Outside of work, Maria is a devoted wife and mom who finds renewal in the outdoors—often off the grid, exploring trails with a backpack and a sense of adventure.

Maria’s blend of experience, character, and faith-driven work ethic make her an essential part of the Ponderosa Investment Group team.