Lessons From a Lifetime of Bets

When people ask me where I learned to recognize opportunity, I usually do not start with boardrooms or property budgets. I go back to childhood. Back to sitting with my grandpa as he explained odds, patterns, and probability through wrestling matches and rounds of liar’s poker. Those weren’t just games. They were lessons in observation, decision-making, and risk. 

By the time I was in junior high, I was essentially running fantasy leagues before they officially existed. My friends and I would draft lineups, set rules, and track outcomes. The wagers weren’t about money. They were about edges—who could see patterns others missed, who could assess margins more clearly, and who could move fastest when opportunity appeared. 

At the time, I thought I was just having fun. But looking back now, with more than twenty years of leadership experience in multifamily housing, I realize those small experiments became the foundation of how I approach risk, strategy, and leadership today. 

Learning to Recognize Opportunity 

Opportunity rarely shows up with a flashing sign. More often, it hides in subtle shifts and emerging patterns. Betting as a kid taught me to look closely. In wrestling, I learned to notice story line swings before they were obvious. In fantasy leagues, I learned to spot undervalued players who were poised for a breakout. 

In property management, the same principle applies. Opportunities to improve operations often reveal themselves through early indicators: a slight dip in resident satisfaction, a trend in maintenance requests, a pattern in occupancy reports. Leaders who notice these signals before they become obvious to everyone else can act with speed and precision. 

That habit of noticing, built through childhood games, has served me in every portfolio I have managed. 

Assessing Risk Realistically 

Another lesson from those early wagers was that risk is never about avoiding loss. It is about understanding the margin between probability and payoff. My grandpa would explain the odds of a poker hand or a wrestling outcome, then ask, “What’s the real risk here?” 

In multifamily, risk shows up in many forms. Budgeting for insurance premiums that continue to rise. Balancing compliance requirements with operational efficiency. Deciding whether to invest in preventative maintenance or ride out the current year. Each decision carries risk, but the leaders who excel are those who evaluate risk with clarity instead of fear. 

That means knowing when to take the safe bet and when to push for the upside. It means recognizing when the downside is limited and the potential gain is significant. And it means being willing to move when others hesitate. 

Moving Decisively 

The third lesson from childhood bets was decisiveness. Opportunities have a shelf life. In sports betting, the odds change by the minute. In fantasy leagues, the breakout player is only undervalued until the rest of the league notices. 

The same is true in operations. A vacant unit is an opportunity for revenue recovery only if it is marketed quickly. A talented employee is an opportunity for growth only if they are developed before another company recruits them. A policy window is an opportunity for funding only if it is seized before it closes. 

Moving decisively does not mean rushing blindly. It means preparing yourself and your team to act with confidence when the opening appears. 

From Bets to Boardrooms 

When I reflect on my career, the throughline is clear. The habits I built in childhood translated into leadership practices that shaped outcomes in multifamily housing. 

• Recognizing opportunity taught me to scan dashboards and resident feedback not just for what is obvious, but for what is emerging. 

• Assessing risk realistically taught me to balance the competing priorities of owners, residents, and staff without freezing in indecision. 

• Moving decisively taught me to lead through uncertainty with enough clarity that teams felt safe to follow. 

These are not just operational skills. They are leadership mindsets. And they all started with the small wagers of my youth. 

Why Small Experiments Matter 

The point is not that everyone should bet on sports as a kid. The point is that small experiments—those seemingly insignificant practices we pick up early—often carry the seeds of leadership. Too often, we dismiss them because they do not look like “serious” training. But they shape how we see, decide, and lead. 

In our industry, I encourage teams to treat small experiments the same way. Try new communication practices. Test small process changes. Pilot a new technology on one property. The goal is not perfection. The goal is learning. Each experiment sharpens the ability to notice patterns, weigh risks, and act quickly when the stakes are higher. 

Closing Reflection 

From childhood bets to boardroom battles, the journey of recognizing opportunity begins in unexpected places. What I learned from odds, stats, and wagers has guided me through occupancy challenges, compliance audits, and leadership transitions. 

So do not dismiss the little experiments in your own journey. They teach you how to see and seize the big ones. 

Whether you are weathering storms or celebrating wins, remember this: your willingness to lead with warmth, wit, and wisdom sets the tone for your team. And sometimes the most powerful leadership lessons are hiding in plain sight, waiting for you to connect the dots. 

Wishing you wonder, wellness, and wins this week. Your leadership is a worthy force.