In this empowering episode of the Breakfast Leadership Show, Michael D. Levitt sits down with Robert Howard, a resilient entrepreneur whose story is a testament to grit, growth, and intentional transformation. From growing up in housing projects to becoming a successful real estate investor, Robert’s journey is one of turning setbacks into stepping stones.
🎙️ From Rock Bottom to Real Estate
Robert opens up about his humble beginnings and academic challenges, including flunking out of college, which led him to a career in car sales. Despite the high-pressure, commission-driven world of auto dealerships, he never stopped searching for a path with more freedom. While working full-time as a general sales manager, he began building his real estate wholesaling business, driven by the belief that time is the new currency.
🚘 Navigating Car Sales Through a Crisis
Michael and Robert reflect on the chaos of selling cars during the pandemic—a time when dealership lots were empty and uncertainty was the only constant. With Michael’s own family history tied to GM, this part of the conversation reveals the toll such careers can take on mental health, family life, and one’s sense of purpose. They both underscore the need to realign your work with your values as life priorities evolve.
💼 From Burnout to Balance
Robert shares how he went from burnout in the auto industry to creating time freedom and financial stability through real estate. His turning point? Investing nearly $50,000 into mentorship and real estate education before finally landing a profitable deal. That one success changed everything, giving him the confidence to walk away from his day job and spend more meaningful time with his family.
🧠 The Entrepreneurial Mindset
This episode dives deep into the mindset shifts required for entrepreneurship. Robert and Michael discuss the emotional rollercoaster of leaving a steady paycheck to follow your dreams. They speak candidly about the internal battles—like negative self-talk and fear of failure—that can derail your progress unless you intentionally choose to believe in what's possible instead of what could go wrong.
🚀 Taking the Leap: Risk vs. Reward
Michael reflects on his own career leap from accounting to leadership consulting, emphasizing that all innovation comes from those willing to take a risk. Real estate, as they both agree, isn’t just a business—it's foundational to life. Robert begins to share the blueprint of how he exited a 20-year career in auto sales to become a full-time investor, offering valuable insights to those contemplating a similar transition.
🎁 Exclusive Wholesaling Resource
Robert is generously offering a free educational resource for those ready to explore real estate wholesaling. Simply DM message the word “Jump” to his Facebook inbox to receive his proven property contract script, video tutorials, and a behind-the-scenes look at how wholesaling really works.
Key Takeaway: Whether you're stuck in a career that no longer aligns with your values or you're looking to reclaim control of your time, this conversation is your reminder that it's never too late to rewrite your story—with resilience, clarity, and a little bit of risk.
🎧 Tune in now and learn how to bet on yourself—and win.
Facebook: https://www.facebook.com/robert.howard.3150