Gary Striewski is best known as an ESPN SportsCenter anchor, but away from the camera, he’s steadily building a real estate portfolio that reflects discipline, creativity, and grit. On a recent episode of Zen and the Art of Real Estate Investing, Gary sat down with Jonathan to share how he balances two demanding worlds and what lessons he’s learned along the way.
Starting Small and Building Steadily
Gary’s entry into real estate began in 2018 with the purchase of his first home after landing a contract at ESPN. Like many new homeowners, he didn’t initially see himself as an investor. That changed during the pandemic, when he had some savings and decided to try his hand at owning rental properties. His approach wasn’t about chasing overnight success but creating steady progress through house hacking and leveraging primary residences into long-term investments.
House Hacking and Hands-On Learning
Gary took a very hands-on path, literally living through renovations, including stretches without plumbing, while rehabbing a duplex. This experience gave him practical knowledge of property maintenance, renovation costs, and what tenants, or as he calls them, “guests,” need to feel at home. His decision to treat residents like partners rather than just rent checks has helped him maintain long-term relationships and minimize turnover.
A Diversified Rental Strategy
With properties in Connecticut and New Hampshire, Gary has experimented with traditional long-term rentals, short-term vacation stays, and mid-term housing for professionals, like doctors and contract workers. This mix not only diversifies his income but also enables him to adapt to market shifts while serving a range of different types of renters.
The Long Game of Real Estate
Gary is quick to emphasize that real estate isn’t about instant results. Instead, it’s about patience, adaptability, and building equity over time. For him, ten properties mark a milestone—a point of financial stability that could support him even if his media career changes. His philosophy aligns with Jonathan’s message throughout the podcast: real estate is about people, persistence, and playing the long game.
For anyone balancing a career with real estate ambitions, Gary’s story proves that steady, intentional steps can lead to both financial freedom and fulfillment.
If you want to learn more about Zen and the Art of Real Estate Investing Podcast, check out https://zenandtheartofrealestateinvesting.com/podcast/273/.