One $500,000 Bet on His Work Ethic Built a $10M Real Estate Company | Ryan Greenberg E372

In this episode, we sit down with Ryan Greenberg, a Maryland-based real estate investor, developer, and property management business owner who has built a company doing over $10 million per year. But his story doesn’t start in real estate, it starts on the water as a towboat captain (in the summers while also working as a teacher), where his work ethic caught the attention of someone who believed in him enough to write a $500,000 private money loan that changed everything. Ryan shares how he turned that opportunity into a growing real estate portfolio, a full-scale property management operation, and a development business, all while maintaining elite discipline through competing in Ironman races. This episode breaks down the power of showing up, building trust, and how consistency in your personal life directly translates into massive success in business