ESPN Host's Real Estate Success: From Single Condo to 10-Unit Portfolio

- Authors
- Published on
- Published on
On this thrilling episode of the BiggerPockets podcast, we meet the remarkable Gary Stry, a man of many talents juggling a high-flying career at ESPN with a burgeoning real estate empire in New England. Stry's journey from a single condo to a portfolio of 10 units in under 2 years is a tale of grit and determination, underscored by the sacrifices he's willing to make for the perfect deal. The team delves into Stry's foray into home renovations in his mid-30s, shedding light on the surprising world of star athletes dabbling in real estate behind the scenes.
Stry's initial venture into real estate with a condo in Hartford sets the stage for his rapid ascent in the property market, showcasing his keen eye for opportunities and strategic decision-making. However, his second property in Bristol proves to be a tougher challenge, as a tenant's financial woes lead to a difficult eviction process. Undeterred by setbacks, Stry's transition to a multifamily property purchase in Bristol exemplifies his unwavering commitment to real estate, even at the cost of personal comforts.
Through Stry's experiences, we witness the highs and lows of real estate investing, where each deal presents its unique set of challenges and lessons. His willingness to take risks and learn from failures underscores the essence of the real estate journey, where success is often forged through perseverance and adaptability. Join us as we delve deeper into Gary Stry's captivating story of resilience, ambition, and the relentless pursuit of financial freedom through the world of real estate.

Image copyright Youtube

Image copyright Youtube

Image copyright Youtube

Image copyright Youtube
Watch Snowballing to 10 Rentals After Selling His Car, Starting with $20K w/Gary Striewski on Youtube
Viewer Reactions for Snowballing to 10 Rentals After Selling His Car, Starting with $20K w/Gary Striewski
Congrats on the success and thanks for sharing
Questions about down payments for rentals
Using a 5 gallon bucket instead of renting
Appreciation for BP
Concerns about buying properties that may not be rentable
Mention of big Wall Street companies mass selling
Warning about a potential upcoming bubble in 2026/2027.
Related Articles

From Rocket Science to Real Estate Success: The Co-Living Strategy
Former nuclear rocket scientist Miller Mwain achieved financial independence through real estate investing with a co-living strategy, turning 6 properties into 41 units for high cash flow. His story highlights the power of creativity and strategic thinking in building a successful investment portfolio.

Mastering Rental Property Acquisition: BiggerPockets Strategies
Learn how to acquire five rental properties in five years with BiggerPockets' expert strategies: house hacking and the Burr method. Achieve financial freedom through savvy real estate investments.

The Hidden Benefits of Real Estate Investing: Beyond Financial Gains
Join BiggerPockets as Dave Meyer and Chad Carson explore the hidden benefits of real estate investing beyond money. Discover the power of intentional, small-scale investing for a fulfilling life alongside financial success.

Maximizing Real Estate Returns: Short vs. Long-Term Strategies
Explore profitable real estate investments with BiggerPockets, analyzing short-term and long-term rental strategies in Texas and Oregon. Learn how to maximize revenue and navigate market challenges for financial success.