EP24 | Build Wealth Around Your Life: Real Estate, Teams & Freedom | Ben Nelson

What if the best business model isn’t the biggest one, but the one that gives you more time, stronger relationships, and a life you actually want to live? In this episode of THE Capital CEO, Jen Conkey sits down with Ben Nelson, Partner at Wild Oak Capital, to talk about real estate syndication, capital raising, team structure, risk, market selection, and building a business around the life you want instead of letting the business consume it. Ben shares how he moved from producing large-scale action sports events around the world into real estate and multifamily investing. After years of solving complex problems, managing teams, and building relationships in high-pressure environments, he and his partners began investing in workforce housing and eventually launched Wild Oak Capital. Jen and Ben discuss how syndication works, why relationships matter so much in real estate, how Wild Oak chooses markets outside its own backyard, and why a smaller, highly aligned team can often move faster than a large organization. They also explore the importance of setting expectations early, preparing for problems instead of assuming everything will go right, building the right people into the right roles, and staying patient when a deal does not make sense. KEY TOPICS • Transitioning from action sports and events into real estate investing • Building Wild Oak Capital around family, freedom, and long-term wealth • How real estate syndication and limited partnerships work • Raising capital and partnering with investors • Choosing markets based on opportunity, teams, and operating conditions • Why strong local property-management relationships matter • Staying patient when a deal does not pencil • Setting expectations clearly with partners and property managers • Learning from early operational mistakes • Building a lean team with complementary strengths • Preparing for problems before they happen • Solving constraints calmly instead of reacting from panic • Creating meaningful events and communities around shared values • Why experiences, relationships, and alignment can matter more than scale for its own sake ABOUT BEN NELSON Ben Nelson is a Partner at Wild Oak Capital, where he works across capital raising, investor relationships, acquisitions, and real estate operations. Before moving into real estate, Ben spent years producing action sports events and working with major brands, experiences that shaped his approach to problem-solving, project management, and relationship building. Today, he and his partners focus primarily on workforce housing and multifamily investments while building a business designed around long-term relationships, flexibility, and family. CONNECT WITH BEN NELSON Wild Oak Capital: https://www.wildoakcapital.com/ Instagram:   / wildoakcapital   Facebook:   / wildoakcapital   LinkedIn:   / wild-oak-capital   Note: This episode discusses real estate syndication, investing, returns, and other financial topics for educational purposes. Nothing in this episode should be considered individualized financial, legal, tax, or investment advice. All investments involve risk, and actual outcomes vary based on market conditions, execution, financing, and other factors. #TheCapitalCEO #RealEstateInvesting #CapitalRaising #Multifamily #Entrepreneurship