What happens when a SportsCenter anchor trades in highlight reels for house hacking?

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes ESPN's Gary Striewski to share his story of becoming a DIY real estate investor while holding down a demanding broadcasting career. Gary takes listeners inside his approach to building wealth, one property at a time, without falling into the "guru culture" that dominates so much of real estate social media.

Gary's journey began with his first home purchase in 2018, following his move to ESPN, which later paved the way for house hacking, renovations, and rental strategies. Today, he balances a full-time media career with managing a growing portfolio of long-term, short-term, and mid-term rentals across Connecticut and New Hampshire. His story is one of perseverance, adaptability, and treating tenants like partners rather than numbers.

From his early days of renovating while living without plumbing, to buying properties straight off the MLS, to learning the power of patience in real estate, Gary demonstrates how an intentional, human-centered approach can turn steady progress into a lasting portfolio. He and Jonathan also dive into the myths of instant wealth, why real estate should be viewed as a long game, and how personal discipline and flexibility create the foundation for success.

Tune in to hear how Gary Striewski proves that balancing a full-time career with intentional real estate investing is not only possible but deeply rewarding.

In this episode, you will hear:

• Gary's path from SportsCenter anchor to hands-on real estate investor

• The advantages of using a primary residence as a future rental property

• Why he calls tenants "guests" and how that mindset strengthens relationships

• Lessons learned from house hacking, renovations, and managing properties himself

• How short-term and mid-term rentals fit into his portfolio strategy

• The role patience, adaptability, and strong communication play in real estate success

Follow and Review:

We'd love for you to follow us if you haven't yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We'd love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select "Ratings and Reviews" and "Write a Review" then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

Supporting Resources:

Gary Striewski's Instagram - www.instagram.com/thekimchipapi

Gary's on TikTok - www.tiktok.com/@thekimchipapi

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

TikTok - www.tiktok.com/@trustgreene

Zillow - www.zillow.com/profile/StreamlinedReal

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/streamlinedproperties

Email - [email protected]

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.