The Power of Holding – Why Selling Too Soon Costs You Millions with Jim Stewart, President & Founder of Stewart Properties, Inc.

Jim Stewart, founder and CEO of Stewart Properties, brings over 40 years of experience in commercial real estate, particularly in multifamily investments. He is also a founding shareholder of Enterprise Bank, the largest bank headquartered in St. Louis. Jim’s career journey is one of resilience and strategic decision-making, from starting out as a young entrepreneur selling candy bars and performing magic shows to becoming a prominent real estate investor and business leader. His ability to identify opportunities, build valuable relationships, and stay ahead of industry trends has contributed to his long-standing success. In this episode, Jim shares invaluable insights into wealth-building through real estate ownership, the importance of holding onto assets for long-term appreciation, and why he decided to bring property management in-house. He discusses his early brokerage career, lessons learned from mentors, and the turning points that led him to focus on multifamily properties. He also highlights his experience co-founding Enterprise Bank and how it shaped his understanding of financial statements and deal structuring. The conversation is filled with real-world experiences, making it a must-listen for investors and entrepreneurs looking to build sustainable wealth. Connect with the Host Twitter: twitter.com/ItsRajTut LinkedIn: https://www.linkedin.com/in/rajtut/ Instagram: instagram.com/ItsRajTut TikTok: https://www.tiktok.com/@itsrajtut Connect with Jim Stewart: https://www.linkedin.com/in/jim-stewart-5815a519/ Timestamps for Key Segments 00:00:01 - Introduction and Jim Stewart’s Background 00:00:19 - Lessons from Managing Properties Firsthand 00:00:36 - The Difference Between Brokering and Owning Real Estate 00:01:23 - Early Entrepreneurship: Selling Candy Bars and Magic Shows 00:04:25 - The Story Behind Marcus the Magician 00:07:46 - Networking and the Power of Relationships 00:12:03 - Journalism School and Unexpected Path to CBS 00:19:17 - The Ronald Reagan Story and Lessons in Confidence 00:25:01 - Transition into Commercial Real Estate 00:27:42 - The Defining Moment That Shifted Jim’s Investment Strategy 00:29:32 - First Apartment Deal and Challenges with HUD 00:35:00 - The Importance of Long-Term Ownership 00:40:06 - Why Jim Brought Property Management In-House 00:45:16 - Using Technology and Pricing Software in Property Management 00:50:10 - The Tornado That Transformed a Property .00:54:47 - Lessons from Being on the Board of Enterprise Bank 00:56:33 - Final Advice: Stay Positive and Develop an “Iron Gut” for Business If you're looking to sell us a 40+ unit multifamily property in the St. Louis region, or another part of MO/IL, please email [email protected] Connect with us at our Website:https://storyboardliving.com/ LinkedIn profile:https://www.linkedin.com/company/storyboard-living/