#416: 3 Real Estate Regrets That Still Haunt Me
Real Estate Investing with Coach Carson
Chad Carson
4.9 • 613 Ratings
🗓️ 6 June 2025
⏱️ 16 minutes
🧾️ Download transcript
Summary
⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm
🎙️ Episode #416 - After 22 years in real estate, I still think about the deals I didn't do—or the ones I let go too soon. Everyone has regrets, but I'm sharing mine so you don't repeat them.
▶️ Next Episode: I spent $12,650 on an HVAC for my Rental (8 Lessons Learned)
📄 Show Notes:
https://www.coachcarson.com/regrets/
🎬 Timestamps:
- (00:00) - 22 Years, 3 Regrets
- (00:55) - The Missed Opportunity
- (02:58) - Lacked Financing Creativity
- (04:52) - Selling a Property Too Soon
- (06:42) - Holding Properties Long-Term
- (08:41) - Chasing Cash Flow Over Wealth Building
- (11:45) - Lessons on Wealth Building and Financial Freedom
- (12:46) - Regrets are Teaching Moments
- (14:39) - Learn from a Community of Regrets
- (15:36) - I spent $12,650 on an HVAC for my Rental
____________________________________________________________________
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Transcript
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| 0:00.0 | I've been investing in real estate for 22 years and I still think about a few of the deals I didn't do |
| 0:04.6 | or a couple of properties I sold too soon and one decision that cost me years of progress. |
| 0:10.1 | These are my biggest real estate regrets and I'm sharing them with you so you don't have to learn |
| 0:14.0 | the hard way like I did. So to share these regrets, I'm going to tell you three simple stories. |
| 0:19.1 | And the first story is about a deal that got away, |
| 0:21.9 | one that I did not buy. And it was all the way back when I was 25 years old, 2005. And to give you |
| 0:28.3 | some context, I'd just been in the business a couple of years. I started investing in real |
| 0:32.0 | estate in 2003. I graduated college in 2002. So I was in my early mid-20s. Did not have a lot of capital, but I was hustling. I was out there talking to people, sending out letters, wanting to buy properties. And some of these properties, I would wholesale. And I had a business partner, so a 50-50 business partner. So we would just flip them to other people, meaning we would get them under contract, maybe do a little bit of work or clean up, and then sell them to another investor almost as is. Other times, we'd fix them up and resell them. But I was very |
| 0:58.1 | interested in rental properties and owning these long-term rentals because I'd heard that's where |
| 1:01.8 | the wealth comes and the cash flow comes. And I sent out some letters to some multifamily unit |
| 1:07.5 | owners in my hometown in Clemson, South Carolina. And I got a call from a super nice gentleman, |
| 1:13.2 | somebody I really respect and learned, went out to lunch several times with and really admired |
| 1:17.7 | because he had been in business for 40 years. I was also a Clemson fan like I was, Clemson Tigers, |
| 1:23.0 | Clemson football. And he had accumulated some rental properties. And this is one particular rental property. |
| 1:28.4 | He said, hey, Chad, I'm thinking about selling this one. I've owned it for you. Actually, |
| 1:32.9 | he built it and he's a beautiful brick buildings in the best location in my town in Clemson near |
| 1:39.8 | downtown, up on a hill, five different buildings, 20 units total. And we discussed them. I looked at |
| 1:46.0 | them with him, went out to lunch a couple times. And he basically told me, you know, I think I'd part |
| 1:50.7 | with him for a million dollars. So a million dollars, 20 units, that is $50,000 per unit. And back |
| 1:58.3 | at the time, the rents were probably $450, $4.95. I can't remember the exact number, but they weren't like a screamer of a deal, but kind of, you know, a little bit below the 1% rule, but in an excellent location. So what did I do? I thought about it. I said, let me, let me work on this. I didn't have any concept of how to come up with a million dollars or to come up with two or three hundred thousand dollars in a down payment it felt very risky to me at that |
| 2:21.2 | point any concept of how to come up with a million dollars or to come up with two or three hundred thousand dollars in a down payment. It felt very risky to me at that point. And I went to a mentor of mine and this just wasn't his type of deal. He liked kind of lower price properties and, you know, he just said he didn't really give me like a green light that he would invest with me. And so I was kind of stuck. And I made him an offer. It was kind of a week offer where I would have said, would you be willing to sell or finance it to me if I paid you $50,000 down and then the other $950,000, I would make payments to you over time. He was nice about it, but he said, no, I don't think that's what I want to do. But looking back on this, so I did not |
| 2:51.5 | buy the deal, passed on it. Many years have passed. And I want to give you the kind of the fast forward of this building, this best location in town. I had the best zoning. It was another thing I didn't mention earlier in addition to being this great location. It had like multifamily dense zoning and very convenient to a lot of things. |
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