The day I left prison, I came out with an unrelenting determination to rebuild my life. On Monday, August 13, 2012, Carole drove me from the prison in Atwater to a halfway house in San Francisco. By the end of that first week, I signed an agreement to purchase a house.
During a time when our country was struggling with a recession, real estate ownership struck me as a clear path to financial stability and growth. My mentors had taught me that opportunities often appear during challenging economic circumstances—if we have the courage to seize them.
Over the next decade, I participated in millions of dollars’ worth of real estate transactions. Those investments generated millions in earnings for Carole and me. We had a simple plan: own appreciating assets and leverage those assets to acquire more. Yet, one mentor from my prison journey always reminded me of the importance of staying flexible. If a strategy no longer serves our goals, we have the right—and responsibility—to pivot.
Looking back, I recognize that real estate fulfilled an important purpose at one point in my life. Still, as I evolved personally and professionally, new perspectives emerged. Carole and I have owned and operated 11 different properties. Over the last few years, however, we’ve been selling these properties. Why? Because, as our world changed, so did the balance of risk and reward.
During the pandemic, for example, government policies made it more challenging to collect rent or evict non-paying tenants, while mortgage payments and maintenance costs remained our responsibility. Insurance requirements grew complex. Furthermore, single-family investments could be both illiquid and vulnerable to shifting regulations.
Although real estate carried undeniable advantages—like leverage and potential appreciation—it no longer aligned with our priorities. I wanted to focus on investments that would move more quickly and possibly provide better returns, such as companies advancing artificial intelligence or Bitcoin.
The investments that I make aren’t right for everyone. Each person should invest time to research and learn about different opportunities. The lessons I learned while serving 26 years in prison, and since getting out, inform the decisions that I make every day.
Carole and I have set a goal of liquidating any asset that has a toilet before the end of 2025. That isn’t to say that real estate isn’t a good investment for some people. But at this stage of our life, Carole and I are choosing to move into a different direction. Choosing one path for a season does not oblige us to follow that path forever, as I learned from Marshall Goldsmith. Instead, we should keep evolving, learning, and adapting our strategies as we gain more insights and experiences.
Self-Directed Learning Question:
- How can you evaluate the strategies you currently use—whether in finance, personal growth, or other areas of life—and decide when it’s time to pivot toward a higher potential?