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Jacob Squires

Financial Planning Associate

As a Financial Planning Associate and Portfolio Trader, Jacob serves in a hybrid role supporting both Aspen’s financial planning and investment management teams. Working closely with the firm’s Chief Investment Officer, he assists with developing financial plans, conducting investment research, executing portfolio trades, managing cash allocations, and helping oversee portfolio implementation across client accounts. By combining technical investment analysis with personalized planning, Jacob helps deliver a thoughtful, seamless experience for clients while supporting Aspen’s evidence-based investment philosophy.

Jacob brings more than a decade of professional experience, including nine years in a small business environment where he developed a passion for building lasting relationships, solving complex problems and delivering exceptional client service. He earned a Bachelor of Science in Business Administration with an emphasis in Marketing from the University of Central Missouri and has successfully completed all three levels of the CFA® Program. He plans to earn his CFA® charter upon satisfying the required experience and intends to further expand his planning knowledge by pursuing the CFP® designation.

Jacob believes great financial planning extends beyond numbers. His approach is rooted in trust, integrity, and clear communication, helping clients make informed financial decisions with confidence. Growing up in a hardworking Missouri farm family shaped his appreciation for preparation, stewardship, and long-term thinking, values that continue to guide both his personal life and his work with clients.

Outside the office, Jacob enjoys spending time with his wife and their two young daughters, whether exploring new places, spending time outdoors, or creating memories together on family trips. An avid outdoorsman, he also enjoys boating and fishing, hobbies that have been part of his life since childhood. He remains passionate about giving back to his rural Missouri community through his support of the Livingston County Cancer Assistance Program, which provides financial support to local families facing cancer.

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