From No Job, No Money, and a Crappy Property to 124 Rental Units

BiggerPockets
BiggerPockets
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Published 2024-04-03
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!

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Connect with Dylan:
BiggerPockets: www.biggerpockets.com/users/dylano31?utm_source=yo…
Facebook: www.facebook.com/dylan.osmon
Instagram: @dylan_osmon or www.instagram.com/dylan_osmon/
Website: propertymanage.biz/osmonproperties
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BiggerPockets: www.biggerpockets.com/users/davem27?utm_source=you…
Instagram: @thedatadeli or www.instagram.com/thedatadeli/
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Connect with Henry:
BiggerPockets: www.biggerpockets.com/users/henryw22?utm_source=yo…
Henry: @thehenrywashington or www.instagram.com/thehenrywashington/

Show notes at: link.chtbl.com/BPRE


00:00 Intro

01:28 Worst Rental Ever?

07:51 What You Need to Know to Invest

10:59 Investing in Small Towns

13:36 Scaling in a Small Market

16:58 124 Units in 4 Years!

22:32 How Dylan Finds Off-Market Deals

26:00 You NEED Cash Reserves

32:31 $70K Profit on One Flip
All Comments (21)
  • @brady_morgan
    Smart kid, good strategy. I have a very similar story myself. Started out listening to BP, lost my corporate job, bought my first deal and learned that I needed to know construction forward and backward to make the most money on real estate since thats where the majority of the margin is. Four years later I own a construction business with basically the same business plan as laid out in this video, except I build new construction rentals rather than looking for deals to buy, much easier to get a deal on land in this small mountain resort town I live in, housing is sparse and high demand, and contractors are booked out two years. Since I am the one building them I dont pay myself a GC fee on the builds so I save 20% on a brand new home. Good video, great to see younger generations being successful! Thanks BP!
  • @aaronmurphy8796
    Thank you all for doing an episode on long term rentals with a cash flow focus . A lot of us really miss this type of content and want more of it
  • @DanielDoesRentals
    Great video! I never hear on BP about investing in small cash flow markets. They only ever talk about big appreciation markets, where you have to buy houses that cost multiple 100 thousands of dollars. I only invest in small towns. The town I invest in is 30k population. These types of cheap cash flowing properties are 100% real and I find them all the time.
  • @RyanIrwinIAC
    Love the conversation about liquidity, so true!
  • @Daveishification
    This was verry insightful. Thank you, Dillan, for the knowledge!
  • @brandonmancinefitness3671
    When looking to do a 1031 exchange; Can you live in one of the units? If so, what are the guidelines around this? If purchasing a duplex, does the rental side need to be a certain percentage of the value/square footage? Any insight is appreciated &as always, thanks for putting out great info!
  • @HowellJesse24
    What training/eduction did you do for direct to seller leads?
  • @dhowto3005
    I'm a native of this area; so, I recognize these towns.
  • @romi929
    So i am asking this 30 min in …. So he had 40 units and 4K in the bank … so none or this units cash flow at all? Don’t quite get it 🤷‍♀️
  • @ryanwalthuis1928
    would you keep your money in a high yield savings account. aslo, when you start investing should you create an LLC?
  • @TheNelsonsGo
    Yoo….why does dude have a 8ft picture of himself behind him? Like, judgment on the redundancy….but I also just have to wonder what the literal thought is on printing off a picture of one’s face for one’s living room??