Snowballing $20K into 10 Rentals by Doing What You (Probably) Won’t w/Gary Striewski

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Feb 24, 2025

Gary Striewski, a rental property investor and DIY home renovator, discusses his incredible journey from a single condo purchase to a thriving rental portfolio. He shares the sacrifices he made, including living without plumbing while renovating. From handling difficult tenants to navigating the complexities of real estate investment, Gary emphasizes adaptability and perseverance. His story encourages listeners to explore unconventional paths to success, showcasing the rewards of community and personal fulfillment through real estate.

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ANECDOTE

From SportsCenter to Real Estate

Gary Striewski, a SportsCenter host, started investing in real estate during the COVID-19 pandemic.
He used his savings and later sold his car to fund his initial investments.

ANECDOTE

First Deal Success

Gary's first deal was a two-bedroom condo in Hartford, purchased for $73,000 in June 2020.
The condo was turnkey and rented through a local program, providing a stable investment.

ANECDOTE

Midnight Mishap

On his first night as a landlord, Gary's tenant lost her key and contacted him at midnight.
This experience was a valuable lesson in the unpredictable nature of property management.

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Would you sell your car, live without plumbing and electricity, and shower at the gym daily to build a rental portfolio? Now, would you do it while having one of the most prestigious jobs on the planet? If you said yes to both, you might as well be Gary Striewski, rental property investor, DIY home renovator, and, yes, host of SportsCenter.

Wait… the host of SportsCenter used a bucket as a bathroom while renovating? Yep, but he’s got a good reason for going through the struggle.

Working at SportsCenter has always been Gary’s dream job, but when 2020 hit, he knew he needed an alternative income stream. Real estate seemed like the obvious answer, but without much savings and only a car to his name he didn’t have many options to invest. So what did he do? Sold his car, downgraded significantly, and picked up a condo for $20,000 down.

Fast forward a few years—Gary has turned that first condo into a full real estate portfolio, including a private ski house that’s soon to be a short-term rental. He’s had evictions, DIY renovations where he lived without plumbing for months, and closings that didn’t go as planned, but with persistence and grit, he’s become an expert investor. Follow Gary’s tenacity, and you can, too!

In This Episode We Cover:

How Gary turned a $20,000 down payment into ten rental units and a real estate portfolio

Gary’s “value-add” renovation that 99% of people would never do themselves

A huge tenant mistake Gary made that will cost you if you repeat it

Why you should constantly evaluate selling your rentals, even if they’re performing well

Whether or not condos are worth it as starter real estate investments

Sports stars who (unsurprisingly) love real estate investing

And So Much More!

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