BiggerPockets Real Estate Podcast Summary
Episode: Snowballing $20K into 10 Rentals by Doing What You (Probably) Won’t w/Gary Striesky
Release Date: February 24, 2025
Host: Dave Meyer
Guest: Gary Striesky, Host of SportsCenter on ESPN and Real Estate Investor
Introduction
In this engaging episode of the BiggerPockets Real Estate Podcast, host Dave Meyer welcomes Gary Striesky, renowned for hosting SportsCenter on ESPN, to discuss his impressive journey from a single condo owner to managing a diverse portfolio of ten rental properties. Gary shares his personal experiences, challenges, and the strategies that propelled his real estate success in the competitive New England market.
Gary Striesky’s Background and Entry into Real Estate
Gary Striesky provides an overview of his career, balancing his role as a sports commentator with his passion for real estate investment. Living in West Hartford, Connecticut, Gary leverages his position at ESPN to network and build his real estate portfolio.
Gary Striesky [01:17]: "I've done a lot of cool stuff in my career... this is the most excited I've been to hop on a show or a podcast in a very, very long time."
The COVID-19 pandemic served as a pivotal moment for Gary, giving him the extra time and motivation to explore real estate as an alternative income stream.
Gary Striesky [02:30]: "Summer of 2020... I found myself having a lot more extra time than I previously had. I just knew I had to do something with it because the 13 cents of monthly interest just wasn't going to cut it."
First Real Estate Deal: Learning the Ropes
Gary recounts his first real estate transaction—a two-bedroom, one-bath condo in Hartford. The seamless process of purchasing a turnkey property provided him with valuable insights and confidence to pursue further investments.
Gary Striesky [04:11]: "This was very, very much low risk, low maintenance, so just an easy first deal for me."
Despite the positive experience, Gary emphasizes the unpredictability of managing rental properties, highlighting the immediate challenges that arise beyond the financial aspects.
Gary Striesky [08:14]: "I learned more in the life lessons of that first deal and continue to learn more than any monthly check, honestly."
Scaling the Portfolio: From Condos to Multifamilies
Encouraged by his initial success, Gary aggressively expanded his portfolio. Selling personal assets like his Jeep Wrangler to reinvest in real estate demonstrates his commitment to growth.
Gary Striesky [12:15]: "I sold my car... I am all in, dude. I'm a grinder."
His second property, a two-family home in Bristol, presented more challenges, including managing unreliable tenants and unexpected property conditions. These experiences taught him the importance of thorough tenant screening and property inspections.
Gary Striesky [13:52]: "It's going to pay to have somebody come out there and clean it... With the extra money, I actually had enough to replace all of the appliances in both units."
Diversification and Strategic Selling
Gary discusses his strategic approach to selling properties when market conditions are favorable, rather than adhering strictly to the buy-and-hold doctrine.
Gary Striesky [20:09]: "My mindset as an investor is definitely a buy and hold... but those are the only two instances I actually sold properties because... it would have been silly to hold on to that and take X amount of years to actually see those gains."
This flexibility allowed him to maximize profits and reinvest in new opportunities, accelerating the growth of his portfolio.
House Hunters and Expanding Influence
Gary shares his experience being featured on the television show House Hunters, where he showcased one of his renovation projects. This exposure not only highlighted his real estate ventures but also connected him with like-minded individuals and potential investors.
Gary Striesky [26:13]: "I bought my first house in New Hampshire, and I feel like it's in frickin Siberia."
His appearance on the show underscored the challenges of renovating and managing properties, especially when balancing personal life and investment responsibilities.
Gary Striesky [28:19]: "For about two months, I was living out of my gym bag."
Current Projects: Short-Term Rentals and Passive Income
Gary introduces his latest venture—a short-term rental property in New Hampshire, aptly named the "Tipsy Moose." Located near Gunstock Mountain, the property caters to both winter sports enthusiasts and summer vacationers, embodying a four-season rental model.
Gary Striesky [33:26]: "It's about 60 seconds from the entrance of the ski mountain... quite literally is a Four Seasons rental."
By leveraging short-term rentals, Gary aims to diversify his income streams while enjoying personal use of the property, effectively turning it into a "forced savings account."
Gary Striesky [34:54]: "I see my entire portfolio... it's just forced savings."
Balancing Personal Life and Investment
Gary emphasizes the importance of maintaining a balance between his professional career, personal interests, and real estate investments. His investments have not only provided financial benefits but also enriched his personal life by enabling experiences like hosting family reunions.
Gary Striesky [35:36]: "It's like, you can't put a price tag on that."
Connecting with the Community and Building Relationships
Through his real estate endeavors, Gary has built meaningful relationships both personally and professionally. His investments serve as conversation starters and bridge connections with athletes and industry professionals who share an interest in real estate.
Gary Striesky [38:56]: "The friendships and relationships that I've started and had all through real estate has been awesome."
Insights and Advice for Aspiring Investors
Gary offers valuable lessons for those looking to enter the real estate market:
- Start Small and Learn: Begin with low-risk investments like condos to gain experience without overextending financially.
- Be Flexible: Adapt strategies based on market conditions and individual property performance.
- Thorough Screening: Implement rigorous tenant screening processes to minimize risks associated with rental properties.
- Leverage Exposure: Utilize platforms like television shows to gain visibility and connect with potential investors.
- Diversify Income Streams: Explore various property types, including short-term rentals, to diversify income and reduce reliance on a single source.
Gary Striesky [21:02]: "I do look at myself as a long-term hold... continuously reevaluating. Is this the best use of my money?"
Conclusion
Gary Striesky's journey from a single condo owner to a diversified real estate investor is a testament to strategic planning, adaptability, and relentless determination. His experiences offer insightful lessons for both novice and seasoned investors aiming to achieve financial freedom through real estate. By balancing personal interests with professional growth, Gary exemplifies how real estate investment can enhance one's quality of life and provide lasting financial security.
Gary Striesky [40:35]: "The whole point of real estate investing is to better your quality of life."
Notable Quotes:
- Gary Striesky [02:30]: "I just knew I had to do something with it because the 13 cents of monthly interest just wasn't going to cut it."
- Gary Striesky [08:14]: "I learned more in the life lessons of that first deal and continue to learn more than any monthly check, honestly."
- Gary Striesky [21:02]: "I do look at myself as a long-term hold... continuously reevaluating. Is this the best use of my money?"
- Gary Striesky [34:54]: "I see my entire portfolio... it's just forced savings."
- Gary Striesky [40:35]: "The whole point of real estate investing is to better your quality of life."
This episode underscores the significant impact that disciplined real estate investment can have on personal and financial growth. Gary Striesky's approach serves as an inspiring blueprint for aspiring investors seeking to replicate his success.