Strengthening Business Relationships through Sport

On Tuesday morning, my anticipation grew as I made my way to Calabasis, California, ready for an invigorating cycling session with Jeffrey Bilbrey, the remarkable SaaS operator behind Leasepath. Over the past couple of years, I've had the pleasure of getting to know Jeffrey, and beyond the prospect of investing in him, I was eager to cultivate a closer bond. Jeffrey's exceptional skills as an operator and his genuine character have always inspired me.

In this blog post, I aim to showcase how engaging in sports activities with business associates can foster profound relationships. When we immerse ourselves in sports, titles and egos dissolve, leaving us focused on conquering that hill or striking that ball. Sports serve as a powerful equalizer, fostering camaraderie and instilling humility.

As both an investor and a founder, I've never considered myself particularly adept at any sport. Nonetheless, I've always embraced the opportunity to cycle, run, or play golf with anyone. Stepping outside our comfort zones is essential because that's where growth happens. Participating in sports alongside colleagues not only helps build trust but also forges strong connections in an enjoyable and interactive manner.

Sports have long played a pivotal role in cultivating relationships. This truth became evident to me when I began cycling with Jeffrey, and our bond grew ever stronger. Cycling is a sport that demands endurance, strength, and a resilient mindset. It pushes you to your limits, challenging you to be your best. Yet, when you engage in this activity with someone else, you both inspire and spur each other on.

While cycling with Jeffrey, I witnessed a side of him that I had never encountered within the confines of a boardroom or a meeting. He exuded a contagious energy, radiating fun and charisma that made anything seem achievable. Our conversations extended beyond business matters, delving into the realm of life itself, allowing me to gain a deeper understanding of who he truly is. We shared tales of triumph, moments of failure, and valuable experiences, enriching our connection in profound ways.

Sports offer a splendid avenue for cultivating relationships with colleagues and investors alike. Whether it's golfing, running, surfing, or any other activity, what matters is breaking away from the daily routine and embracing something beyond the realm of work. Engaging in sports with others allows for better comprehension, common interests, and shared adventures. Most importantly, it facilitates the establishment of trust.

In conclusion, engaging in sports activities with business colleagues presents an extraordinary opportunity to foster meaningful relationships. Through cycling, I developed a deeper understanding of Jeffrey, forging a bond that would have been unlikely to form otherwise. Embracing situations that lie beyond our comfort zones is the catalyst for personal growth and the cultivation of strong connections. So, go ahead and invite your colleagues or investors to join you for a run or a round of golf. You never know where these shared experiences might lead you!