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

BiggerPockets Real Estate Podcast

BiggerPockets

Education, Business, Investing

4.8 • 16.5K Ratings

🗓️ 24 February 2025

⏱️ 41 minutes

🔗️ Recording | iTunes | RSS

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Summary

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! Links from the Show Join BiggerPockets for FREE Let Us Know What You Thought of the Show! Ask Your Question on the BiggerPockets Forums BiggerPockets YouTube Apply to Be a Podcast Guest Try REsimpli, The Only All-In-One Real Estate Investor CRM Software That Helps You Manage Data, Marketing, Sales, and Operations Grab Dave’s Book, “Start with Strategy” Sign Up for the BiggerPocket Real Estate Newsletter Find an Investor-Friendly Agent in Your Area 10 Hidden Ways to Buy Properties with Huge “Upside” Connect with Gary Connect with Dave (00:00) Intro (02:19) 1 Condo to 9 Rentals! (04:06) Base Hit First Deal (08:56) A Big Tenant Mistake (12:48) $60K Profit in 1 Year! (19:17) Living Without a Toilet for a Deal? (25:24) First Short-Term Rental (30:04) ANYONE Can Do This! (32:33) They Invest in Real Estate, Too!? Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/real-estate-1087 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email [email protected]. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	How much are you willing to sacrifice to build your real estate portfolio?
0:04.3	You might have seen today's guests at his day job hosting SportsCenter on ESPN,
0:09.0	but he still sold his car and lived for months without indoor plumbing just to make a deal work.
0:15.3	Keep watching to find out how the man who calls himself the kimchi poppy has built an incredible New England portfolio,
0:23.0	including a four-season mountain vacation home that's about to be paying for itself.
0:32.3	Hey, everyone, I'm Dave Meyer, and this is SportsCenter. Just kidding, I really always wanted to say that into a microphone.
0:39.1	This is actually the Bigger Pockets podcast where we teach you how to achieve financial freedom through real estate investing.
0:45.8	But today's guest is Gary Streisky, who hosts SportsCenter on ESPN when he's not busy building a real estate portfolio in Connecticut and New Hampshire.
0:55.5	Gary is here and going to tell us how he went from owning just a single condo to 10 units
1:01.7	in less than two years, while he suddenly got the urge to start doing home renovation projects
1:07.0	in his mid-30s and which star athletes are also secret real estate investors.
1:12.6	Let's bring on Gary. Gary, welcome to the Bigger Pockets podcast. Thanks for being here.
1:17.6	Dave, I got to tell you, man, I've done a lot of cool stuff in my career. And I'm not just saying
1:22.0	this because we are in present company. This is like the most excited I've been to hop on a
1:26.5	show or a podcast like in a very,
1:29.1	very long time. Awesome. I'm excited to have you here. And I think a lot of our audience probably
1:34.2	recognizes you. But for those who don't, can you just tell us a little bit about yourself and
1:39.4	what you've been up to in addition to being a real estate investor? Of course. I mean,
1:43.8	obviously you're referring to the
1:46.0	people who recognize me as being the Polish sportscaster on any given network, depending on where
1:55.5	regionally you're listening from, from Denver, spent that good handful of years in Boston, embedded with the Boston Red Sox.
2:04.6	And now I continue to live out my dream of hosting Sports Center on ESPN. So I am joining you from
	...

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