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Real Estate Investing with Coach Carson

#425: From Accidental Landlord to 7 Rentals - Here's How

Real Estate Investing with Coach Carson

Chad Carson

Investing, Business

4.9613 Ratings

🗓️ 7 July 2025

⏱️ 56 minutes

🧾️ Download transcript

Summary

⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm

 

🎙️ Episode #425 - O'Shea's first property didn't go as planned—but it changed everything. Hear how he turned renovation mistakes and budget overruns into a growing rental portfolio and a path toward time freedom.

 

▶️ Next Episode: DSCR Loans Explained - How to Qualify Without a W2 or Tax Returns 

https://podcasts.apple.com/us/podcast/413-dscr-loans-explained-how-to-qualify-without-a/id1448707654?i=1000709881289

 

📄 Show Notes: 

https://www.coachcarson.com/?p=20803&preview=true

 

🎬 Timestamps:

  • (0:00) - From accidentally investing to FI
  • (8:38) - O'Shea's daily life & career
  • (11:30) - From Jamaica to NY
  • (12:57) - O'Shea's journey to buy more properties
  • (25:09) - O'Shea's intro to short-term rentals
  • (26:59) - Short-term investing lessons
  • (30:35) - Long-term vs short-term rentals
  • (44:18) - Buying properties w/out enough capital
  • (49:00) - O'Shea's current + future goals
  • (51:19) - Balancing home life & real estate
  • (52:58) - O'Shea's advice for investors
  • (54:16) - DSCR Loans Explained

🔗 Connect with O'Shea: 

____________________________________________________________________

⚒️ Get my FREE Real Estate Investor Toolkit:
https://www.coachcarson.com/toolkit-pod

🖥️ Learn with Coach (Courses, Books & more):
https://www.CoachCarson.com

👋 Connect with Me:

💵 Need Investor-Friendly Financing?
This is who I trust → https://www.coachcarson.com/bryan

💰 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-YT

Transcript

Click on a timestamp to play from that location

0:00.0

I didn't plan this. This was a primary that I turned into a rental. This was a Zillow listing, where the owner was, make me a deal or make me an offer.

0:08.7

O'Shea started with rental properties by accident, but from there, he and his wife built a seven property portfolio while working full-time jobs.

0:15.7

I was terrified of finding a tenant and doing screening because I heard all the horror stories. I did all of this as trial by fire. As you'll learn in this story, you don't need to start real estate investing with perfect knowledge or lots of money. It takes time. You can do one a year and it will work itself out over time. So if you're busy, unsure where to start, or worried about making mistakes, this conversation with

0:37.5

O'Shea will inspire you to take the next step. Let's get started.

0:45.1

So, Shea, I want to jump into your journey and talk about, you know, what it's been like

0:52.8

the last five years or so for you investing in real estate. But I would love for people to get to know you a little bit better, first of all. So can you can you start just tell us first of all about a little bit about your real estate investing? Like, how many properties do you have? What kind of properties do you own right now? I have seven properties. I invest in St. Pete mostly. I got started in 2017. I didn't plan this. This was a primary that I turned into a rental. And I didn't buy below market or I didn't get a deal or anything. In fact, this was a Zillow listing where the owner was make me a deal or make me an offer.

1:33.8

Do you remember those listings?

1:35.0

I remember those, yes.

1:35.8

And usually they list it way above market and, you know, whichever sucker is willing to make them.

1:42.1

That was me.

1:46.6

So there was an area that was up and coming and I really wanted to live there my wife then at the time girlfriend did not like that

1:52.7

area but um I did all the research and I really liked everything that was coming out through the

1:59.0

city planning and everything.

2:09.6

So I made an offer and the neighbor when I was touring thought that I might have been crazy because this house has been sitting for several years.

2:12.9

No one wants to pay that amount of money.

2:15.3

It's not in great condition.

2:17.0

You know, it's just an okay house.

2:19.5

So we close. Uh, wife's not happy. She's okay. But, um, we have to do lots of work. And that

2:28.5

wasn't supposed to be the plan. We're supposed to find something closer to turn key. We don't

2:32.5

want to live in anything and do work on it,

2:34.8

but I thought it was a right move. So now I go hunt a contractor. And, you know, this is always a

2:40.8

fun part. I'm not in the industry. I don't know anything. I don't know anyone. So the contractor

...

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