Dennis Havrilla: From Professional Football to the Triple Net Playbook

What happens when a professional quarterback takes the lessons he learned on the football field and applies them to commercial real estate?

In this episode of SF Commercial Property Conversations with Bruce Bean, Bruce sits down with Dennis Havrilla, founder of Havrilla Commercial Investment Group and creator of the Triple Net Playbook.

Dennis shares his unusual path from professional football into the world of triple net (NNN) commercial real estate. It all started when a fellow professional football player encouraged him to get his real estate license—and even sent him the money to sign up for the classes.

That decision eventually introduced Dennis to a boutique commercial real estate firm focused on triple net properties such as drugstores and dialysis centers. Dennis had to learn quickly, but his experience as a quarterback had already taught him how to absorb a playbook under pressure.

Today, Dennis and his wife work together helping investors understand triple net properties and opportunities to move from actively managed real estate into more passive investments through strategies such as 1031 exchanges.

Dennis also shares how investing in his first triple net property changed his own relationship with professional football. Knowing he had cash flow outside of the game gave him greater financial peace of mind and allowed him to play with more freedom.

Bruce and Dennis also discuss what investors should look for before purchasing a triple net property. Dennis explains why a property marketed as a “triple net” may not always be a true absolute triple net lease. Investors need to understand who is responsible for expenses such as the roof, structure, and parking lot.

They also discuss tenant quality, location, traffic counts, exit strategies, cap rates, essential businesses, and why the underlying real estate matters when evaluating a deal.

Dennis believes successful triple net investing comes down to understanding the lease, the tenant, the location, and the long-term strategy—not simply chasing a cap rate.

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