The transition from the adrenaline-fueled, competitive days of professional sports to quieter civilian life can be challenging—something Dennis Havrilla has experienced firsthand. As a former professional athlete who has since entered the real estate world, Havrilla recognizes that many athletes struggle to redefine their identities and find new purpose once their sports careers end, just like he did. That’s why he decided to commit to helping fellow sports professionals navigate this period of uncertainty.
After his professional football career with the Indoor Football League and the Arena Football League, Havrilla faced a daunting question: “What now?” After eventually making his way into real estate, he now sees his journey as not just a path to personal success but also a roadmap for other athletes who face the same struggle when trying to find a new vocation. This led him to build a business with the purpose of mentoring and helping them transition into real estate.
“The end of an athlete’s career can feel like a hard stop,” Havrilla says. “You go from routine and structure, constant physical exertion and team dynamics, to needing a new kind of playbook. Real estate investment can offer a solid long-term plan and financial security for many athletes seeking stability.”
Havrilla wants to educate athletes about investing in Triple Net (NNN) properties—a model commonly seen in commercial real estate where tenants handle most property expenses—through his company Harvilla Commercial Investment Group. He also authored The Triple Net Playbook, which is meant to be a guide for these kinds of investments. Based on the former athlete’s experience, this strategy allows for a more hands-off investment approach and can offer consistent returns, but new investors need to advance toward these opportunities with careful consideration and proper guidance.
Beyond introducing athletes to triple net leasing, Havrilla says he also helps them learn about the importance of resilience and financial planning through individual coaching sessions and group workshops. He adds that his outreach extends to professional athletes as well as collegiate players, equipping them with tools to manage their wealth effectively from an early stage. By promoting financial literacy, Havrilla hopes to see athletes avoid the financial struggles that many face after their sports careers.
As someone who was raised in a family battling substance abuse and financial instability, the real estate professional is no stranger to financial hardship. Havrilla recalls his father struggling with addiction while his mother worked multiple jobs to support their family—a reality he says is not far from the challenges some athletes face when their playing careers come to an abrupt end.
Having experienced the pressure of seeking financial stability, both when he was young and when he stopped playing professional football, Havrilla feels passionate about empowering athletes with the knowledge to make informed financial decisions that can sustain them well into their post-playing lives. “It’s not just about securing your next paycheck,” he says. “It’s about making sure each paycheck works for you in the long term.”
Looking ahead, Havrilla hopes to expand his influence not only in real estate but also as a mentor to athletes worldwide. His goal is to shift the narrative surrounding life after professional sports—from the oft-seen image of struggling retired athletes to that of successful investors and business leaders, leveraging the discipline and perseverance they learned while playing. As more sports players find themselves at a career crossroads, Havrilla believes providing a playbook for financial health and personal fulfillment is becoming increasingly important.
