"I'm Not Sure You Called The Right Show"

Summary

Podcast Summary: The Ramsey Show Highlights - "I'm Not Sure You Called The Right Show"

Date: December 17, 2025
Host: Ramsey Network (with Real Estate Expert & Financial Advisor)
Guest Caller: James
Episode Length: ~8 minutes (excluding ad spots)

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Episode Overview

This episode features a rapid-fire coaching session with "James," an ambitious caller seeking advice about expanding his Airbnb operation. The hosts—drawing from vast personal finance and real estate experience—offer critical insights into the risks and realities of the short-term rental business, emphasizing caution, sustainability, and the need to consider potential downsides.

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Key Discussion Points & Insights

1. James’ Background & Question

[00:12-01:18]

• James is 40, engaged, has a two-year-old, and operates three successful Airbnbs with his fiancée.
• The Airbnbs grossed $102,000 last year, projected $127,000 this year (62% profit margin).
• Both have strong W-2 incomes: James in hospitality sales ($100-120K), fiancée is a psychologist ($110K).
• James is considering buying a fourth Airbnb in a historic commercial building but faces a 40% down payment requirement from lenders.
• His question: Is adding a fourth Airbnb a prudent investment, or does it increase risk excessively?

2. Opening Reaction: "Not Sure You Called The Right Show"

[01:18-01:32]

• Real Estate Expert begins with humor and candor:

  "Okay, well, I'm not sure you called the right show. I'm not sure that you know what we do, but..."
  (Real Estate Expert, 01:18)

• The host emphasizes personal experience in real estate, including going broke due to over-leverage in his 20s.

3. Risk Factors Highlighted

[01:18-04:00]

• Labor-Intensive Business:
  The returns from Airbnbs require a lot of hands-on work.

  "The money that you're earning on those Airbnbs, you're working your hiney off to get that money."
  (Real Estate Expert, 02:02)
  James confirms he handles maintenance, housekeeping, and check-in.

• Personal Bandwidth:

  "You have a two year old...you ain't got time to do nothing!"
  (Real Estate Expert, 02:30)

• Regulatory Vulnerability:
  Many cities and HOAs have cracked down on short-term rentals. Even in commercial zones, there’s risk (e.g., if a new large tenant dislikes upstairs activity).

  "Many entire municipalities are passing zoning to stop it because they’re disruptive to the neighborhood."
  (Real Estate Expert, 02:45)

• Ownership & Debt Concerns:

  "You're buying property with someone you're not married to. Very dangerous. Number two, you're going in debt to do it. Very dangerous. Number three, you have a high risk business model that's dependent upon someone else called Airbnb. Very dangerous."
  (Real Estate Expert, 04:48)

4. Scalability & Burnout

[05:00-06:25]

• Hosts warn against simply scaling up if the business can't run without the owner.

  "If it works for 4, but not 5 or not 10, then maybe we shouldn't do 4...because the idea is not scalable to where you get out of being the maintenance man."
  (Real Estate Expert, 05:55)

• Financial Advisor adds:

  "You just have to keep absorbing more work and more work..."
  (Financial Advisor, 06:25)

• Ultimately, the risk is both in personal burnout and business fragility.

5. Airbnb Platform Dependence: The Tech & Policy Risk

[06:34-07:19]

• Host shares a concrete example of how a tech platform change (Apple dropping app support) led to a $20M loss for their business.

  "...Apple decides they're not going to support the app anymore...that little move right there cost us about $20 million two years ago."
  (Real Estate Expert, 06:45)

• The message: If your business is on the razor's edge, small external changes can wipe you out.

6. Psychological Blind Spots & Recession Wisdom

[07:19-08:00]

• Financial Advisor notes many have only seen upside in recent years and may lack preparedness for downturns.

  "There seems to be a lot of folks who...entered into 2010 to 2025, and it’s been seemingly mostly upside...there’s the assumption that’s just going to keep going that way."
  (Financial Advisor, 07:19)

• Real Estate Expert cautions about bankruptcy if bookings dry up:

  "...if you’ve got your thing based on the Airbnb income of 4 and suddenly they don’t rent for 4 months, you’re in bankruptcy."
  (Real Estate Expert, 08:00)

• Being debt-free offers resilience; otherwise, the whole model is fragile.

7. Final Guidance: Nightmare Killer, Not Dream Killer

[08:13-08:37]

• The experts praise James's ambition but urge him to avoid unnecessary risk:

  "I believe in being a nightmare killer, not a dream killer."
  (Real Estate Expert, 08:37)

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Notable Quotes & Memorable Moments

• On Unseen Downsides:

  "All you have seen in this is the upside. You've not considered any of the downsides. And that's the way I was in my 20s and it's what caused me to go broke."
  (Real Estate Expert, 04:35)

• On Platform Dependence:

  "Apple decides they're not going to support the app anymore...that little move right there cost us about $20 million two years ago."
  (Real Estate Expert, 06:45)

• On Caution vs. Optimism:

  "It's tough to tell somebody, hey, you have to be prepared for when this thing goes south a little bit or when the roller coaster takes a...goes down."
  (Financial Advisor, 07:44)

• On Ownership with a Fiancée:

  "You're buying property with someone you're not married to. Very dangerous...you get yourself into all kinds of messes here."
  (Real Estate Expert, 04:48)

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Important Timestamps

• 00:12 – James introduces his Airbnb business and growth question
• 01:18 – Host shares background and sets the tone for advice
• 02:22-03:16 – Discussion of labor intensity and time constraints
• 03:35-04:48 – Deep dive into regulatory, partnership, and risk issues
• 05:25-06:25 – Scalability, burnout, and the perils of adding "just one more"
• 06:34-07:19 – Tech platform & policy risks
• 07:19-08:00 – Reality check: preparing for downturns
• 08:37 – Final wrap-up: "Nightmare killer, not a dream killer"

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Takeaway for Listeners

• Real estate and Airbnb can be lucrative, but only with clear eyes on risk, scalability, and effort.
• Don’t let recent success blind you to potential pitfalls—plan for downturns, keep debt minimal, and avoid partnership complications outside of marriage.
• Above all, protect yourself from becoming your own bottleneck and from being too dependent on any single platform or regulatory environment.

Listeners walk away with a sobering, practical mindset toward short-term rental investing—more focus on safety nets and sustainability, less on chasing the next big deal without considering worst-case scenarios.

Transcript

[Christian Healthcare Ministries Announcer]

Brought to you by CHM, a budget friendly faith based alternative to health insurance. Chministries.org budget so I'm a 40 year old guy.

[James (Caller)]

I got a fiance and a baby who turned two in July. And my fiance and I, we have three Airbnbs that are doing really well. Four years into it, last year we grossed about 102,000. This year we're forecasting to do about 127,000 gross on the three Airbnb DMVs with a 62% profit margin. Day job is hospitality sales. I make about 100, 120 thousand a year. She is a psychologist, she makes about 110. So our issue is there are these micro lofts and another one is available, but it's in a super historic old building. And I'm thinking about getting a fourth Airbnb, but the banks are telling me that I got to put 40% down. They're going for about two and a quarter. So I want to hear your take. If I should get another profitable Airbnb and have it under the same roof as all my other ones or is that considered maybe too high risk?

[Real Estate Expert]

Okay, well, I not sure you called the right show. I'm not sure that you know what we do, but. So I own several hundred million dollars in real estate. Okay. I love real estate as an investment. I went broke in the real estate business in my 20s, if you haven't heard the story. And the way I did that was I borrowed too much money and the banks called our notes because we were in a high risk scenario. The Airbnb business is basically the hotel business. It's a very high labor, intense, you know, a lot of hassle. So the money that you're earning on those Airbnb, you're working your hiney off to get that money. And you're probably working, you're working some other people's hiney off because it's a lot of hassle.

[James (Caller)]

I'm the maintenance man, I'm the housekeeper, I'm the guy checking them in. Yep.

[Real Estate Expert]

And you have a two year old way, so.

[James (Caller)]

Yep.

[Real Estate Expert]

Yeah. Why don't you pick up golf too? Oh my God, you know, I mean, you ain't got time to do nothing. So I don't know that you have the bandwidth to add another one on your personal number one. Number two, the risk with Airbnbs is, as you probably know, and I don't know where it stands in Providence, Rhode island, but many HOAs, many neighborhoods, many entire municipalities are passing zoning to stop it because they're disruptive to the neighborhood. And so I know a lot of people that have lost the ability to run an Airbnb on a property they bought for an Airbnb and in a historic setting, that's very possible.

[James (Caller)]

Right. It's any unique building. It's the oldest mall in America where there's retail on the first floor. On the second and third floor was repurposed to Airbnb. So it is in a commercial zone.

[Real Estate Expert]

Okay, so that means the risk of them rezoning it and keeping you from.

[James (Caller)]

Doing it is less to my understanding. Yes.

[Financial Advisor]

Or it's going to take one new tenant downstairs that's a big tenant that says, I don't want people living upstairs.

[James (Caller)]

Well, we're all on the board now.

[Real Estate Expert]

They're already got residential in there. It's just a matter of whether it's nightly rental.

[Financial Advisor]

Okay, right.

[Real Estate Expert]

Residential because it's a hotel in a sense. So I don't know. You're doing some things I don't want to do and I don't recommend people do things I don't want to do. So number one thing you're doing is you're buying property with someone you're not married to. Very dangerous. Number two, you're going in debt to do it. Very dangerous. Number three, you have a high risk business model that's dependent upon someone else called Airbnb. Very dangerous. Number four, you have to do all the freaking work and you're getting ready to add 25% to the workload, going from three to four and you have a two year old. Very dangerous. So that's what I meant by I don't know if you've been around as much. And I'm not trying to be mean to you. I just think, I think that all you have seen in this is the upside. You've not considered any of the downsides. And that's the way I was in my 20s and it's what caused me to go broke. And so now I'm always looking. I'm not negative thinker. I buy. I mean, like I said, I own hundreds of millions of dollars of real estate. I love real estate, but I have low hassle real estate. I don't, I don't own a single Airbnb. And we've got enough residential. I easily could do that. But we don't want to screw with it. It's just too dad gum much work for the money. Too much drama for the money. And so we'd rather make the money, you know, a little slower and with a lot Less hassle factor. And we don't borrow money. 100% of our real estate's paid for. I don't borrow money to buy real estate. So I'm a fan of the category of real estate. But after that, I've kind of given you some things to think about. So until you've thought through all of those things and make sure that you've decided how you're going to own what ownership vehicle you're going to own this in with someone that you're not married to. Oh, real dangerous. You know that, that you get yourself into all kinds of messes here, and I think that's what the bank is smelling, and that's why they're wanting a huge downstroke. But, you know, a good way to look at any business opportunity, too, James, is to scale it in your mind. And if it doesn't scale, then don't grow it. Meaning if it works for 40 Airbnbs, we might do 4. If it works for 4, but not 5 or not 10, then maybe we shouldn't do 4. Why is that? Well, because it's going to. The, the, the idea is not scalable to where you get out of being the maintenance man.

[Financial Advisor]

You, you just have to keep absorbing.

[Real Estate Expert]

Yeah.

[Financial Advisor]

More work and more work and more.

[Real Estate Expert]

Work, and pretty soon you're going to go, I want to quit my job and be Mr. Airbnb. Right. And that's not.

[Financial Advisor]

Then your one Airbnb app change or one Airbnb municipality change, or your one.

[Real Estate Expert]

Yeah. Apple decides they're not going to support the app anymore.

[Financial Advisor]

That's right.

[Real Estate Expert]

With 13 point whatever. Oh, my crap. You know, I mean, all kinds of people. I mean, it caught that. Caught that little move right there cost us about $20 million two years ago. So you know that just because Apple decided to cough and so, you know, all that stuff. So these are things you can't anticipate and you leave yourself vulnerable to it when you're just living right on the wire, when you're around the edge, and then you just keep adding to it, keep adding to the plate till the food falls off, you know, and that's, that's what I heard here is a really super busy guy. Well, ambitious guy.

[Financial Advisor]

You said this. And, man, this has become increasingly. I felt it heavier and heavier. I have a very real lived experience being in the workforce during 2008, 2009, and there seems to be a lot of folks who have entered into 2010 to 2025, and it's been seemingly mostly upside. It's just been win after win after win after win.

[Real Estate Expert]

Plus or minus Covid and.

[Financial Advisor]

Yeah. Plus or minus covet. And there's the assumption that's just going to keep going that way. And there's no, man, it's tough to tell somebody, hey, you have to be prepared for when this thing goes south a little bit or when the roller coaster takes a, you know, goes down and, man, people don't, don't have the psychology for it right now.

[Real Estate Expert]

Yeah. I mean, if you've got your thing based on the Airbnb income of 4 and suddenly they don't rent for 4 months, you're in bankruptcy.

[Financial Advisor]

Whereas if you own them all in cash, you're annoyed.

[Real Estate Expert]

Exactly. You're. Well. Or you put renters in. Yeah. And you get out of the Airbnb business and you move on, you know, and that's. It's not a big deal. Right. You know, but, yeah, this is, It's a problem. Yeah. So, no, I'm, I, I like James because he's ambitious and he's going after it. He's going for it. I want to support that, but I, I believe in being a nightmare killer, not a dream killer.

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