Matthew Anderson - Making Better Decisions in Real Estate, Law, and Entrepreneurship

Matthew Anderson is a Partner at Anderson & Harrison, PLLC, a Nashville-based boutique law firm focused on construction and real estate law. The practice represents real estate professionals, investors, developers, and operators in breach-of-contract and tort disputes related to real estate and construction. As a real estate investor and operator, Matthew has approximately $25M of assets under management, consisting primarily of multifamily and office space in Tennessee. In this episode… Entrepreneurship often requires choosing between what's working and what's worth building next. As opportunities expand, the harder decision is not always whether to grow, but what to let go of in order to grow well. How do you know when a difficult season is actually pointing you toward the next right move? Real estate and construction law expert Matthew Anderson built his career at the intersection of legal strategy, investing, and entrepreneurship. After starting out in law while quietly pursuing real estate deals on the side, he eventually stepped into business ownership, learning that growth required more than ambition — it required focus, discipline, and the courage to say no. A deeply personal setback, including grief and a delayed bar exam, became an unexpected turning point that gave Matthew space to study investing and take action. His advice: stop dabbling, make offers, learn through due diligence, and use action to build confidence. In this episode of The Decision, Robert Hartline sits down with Matthew Anderson, Partner at Anderson & Harrison, PLLC, to discuss making difficult decisions in entrepreneurship and real estate investing. Matthew shares how he joined EO, why investor experience shapes his legal advice, and how a major personal setback helped launch his investing journey.