meta_pixel
Tapesearch Logo
Log in
BiggerPockets Real Estate Podcast

928: 124 Units in 4 Years by Only Investing in Small Towns and Tiny Markets w/Dylan Osmon

BiggerPockets Real Estate Podcast

BiggerPockets

Investing, Education, Business

4.816.6K Ratings

🗓️ 3 April 2024

⏱️ 45 minutes

🧾️ Download transcript

Summary

In just four years, Dylan Osmon went from having no job, barely any money, and no real estate investing experience to owning over one hundred rental units. How’d he do it so quickly? Before we answer that, we’re going to make this a little more impressive. Dylan isn’t buying in the big cities with tons of inventory going on the market every week—he’s been buying in tiny towns that you and almost everyone else listening to this have never heard of. And he may have struck gold by doing so. Dylan acquired his first investment property right before the lockdowns. Then, after closing, he quickly realized that this was the worst rental property he could have bought. It had everything—low rents, tenants who never paid, and, to top it off, a cesspool of human waste in the crawlspace—everything you need for a deal gone wrong. He quickly got control of this nightmare rental, flipping it and walking away unscathed. But now, he had to start back from square one, this time with new knowledge. Over the next few years, Dylan made it his mission to build multiple income streams, so every dollar he made went into new deals. He eventually met partners that would help him scale even quicker and learned the secret to finding the best off-market properties—don’t worry, he shares it in this episode! Now, he’s got over one hundred rentals across three small markets, and if you copy his strategy, you could too! In This Episode We Cover: Why you CANNOT overlook small markets when investing in real estate The #1 best way to find off-market real estate deals in any area How much emergency reserves you should have on hand at ALL times Investing in real estate with no money by finding the deal FIRST Scaling your real estate business faster so you don’t have to do so much of the work The risk of having only a W2 salary and just one income stream And So Much More! Links from the Show Find an Agent Find a Lender BiggerPockets Youtube Channel BiggerPockets Forums BiggerPockets Pro Membership BiggerPockets Bookstore BiggerPockets Bootcamps BiggerPockets Podcast BiggerPockets Merch Join BiggerPockets for FREE Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts Get More Deals Done with The BiggerPockets Investing Tools Find a BiggerPockets Real Estate Meetup in Your Area Expand Your Investing Knowledge With the BiggerPockets Books Be a Guest on the BiggerPockets Podcast Dave's BiggerPockets Profile Dave's Instagram Henry's BiggerPockets Profile Henry's Instagram BiggerPockets' Instagram Use The BiggerPockets Investment Calculators On Your Next Deal Hear Dave and Henry On the “On the Market” Podcast 8 “Under the Radar” Housing Markets With Low Prices and High Cash Flow Connect with Dylan Dylan's BiggerPockets Profile Dylan's Facebook Dylan's Instagram Dylan's Website   Check out more resources from this show on https://www.biggerpockets.com/blog/real-estate-928 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0

Hey everyone and welcome to the BiggerPockets real estate podcast.

0:03.4

I'm Dave Meyer joined today by Mr Henry Washington.

0:07.4

Thanks for being here, man.

0:08.4

Hey, thanks for having me man.

0:09.7

This is always a pleasure.

0:11.3

Yeah, and today we're talking about something. I know you and I both have a pleasure. Yeah, and today we're talking about something I know you and I both have a passion for which is picking the right market.

0:17.6

This is obviously something that's on top of most people's mind and I personally spend a lot of my life looking into different real estate

0:25.0

markets both professionally for my job at Bigger Pockets but also for my own personal portfolio.

0:30.8

But the truth is, you know, after doing so much research into this stuff, what I've found is that you can find deals in almost any market. You just have to know what strategies work in each market. And today's investor story we're going to hear

0:45.4

from someone who's making deals work in a place that I personally have never

0:50.2

really considered investing it. That's right. Today we're going to talk with

0:53.5

Dylan Osman and Dylan shares exactly how he's finding and making deals happen in

1:00.1

small Thames. You'll also hear about things he's changing in his strategy today

1:04.5

that can apply to any investor. Yeah I'm super excited about this because I think you

1:08.7

know a lot of times I'm personally biased I overlook small towns I kind of just look at big metro

1:13.7

areas and look at these big macroeconomic trends but there are obviously deals

1:18.8

to be had and strategies that work and advantages in investing in small towns and we're going to hear all about that

1:26.2

from Dylan so let's jump into it. Dylan Osman welcome to the show. Dylan you did your very first deal back in 2020 which is a pretty bold decision I might say I don't think a lot of people were doing their first deal in real estate back in 2020

1:40.6

But kudos to you for doing it.

1:42.6

But it sounds like it didn't actually go the way

1:46.2

you were expecting.

1:47.3

So can you just tell us a little bit about that deal

...

Please login to see the full transcript.

Disclaimer: The podcast and artwork embedded on this page are from BiggerPockets, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of BiggerPockets and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.

Copyright © Tapesearch 2026.