#432: More Rental Cash Flow is Just One Tough Conversation Away
Real Estate Investing with Coach Carson
Chad Carson
4.9 • 613 Ratings
🗓️ 1 August 2025
⏱️ 14 minutes
🧾️ Download transcript
Summary
⭐ Join Rental Property Mastery, my community of rental investors on their way to financial freedom: https://coachcarson.com/rpm
🎙️ Episode #432 - Real estate success isn't just about spreadsheets, it's often about the uncomfortable conversations we avoid. Coach shares how these conversations with sellers, tenants, and partners have led to some of his best deals.
▶️ Next Video: 5 Rental Property Mistakes That Cost Me Thousands! https://www.youtube.com/watch?v=5pZGBzaeMw0
📄 Show Notes: https://www.coachcarson.com/toughconversations/
🎬 Timestamps:
- (0:00) - The convos that get results
- (1:08) - Making uncomfortable offers
- (4:20) - Getting out of bad situations
- (6:42) - Preventing late payments from tenants
- (7:12) - Tough convo tips
- (9:03) - Write out what you want to discuss
- (9:40) - Practice your convo
- (12:00) - Take massive imperfect action in a community
- (13:00) - Top 5 REI Mistakes
____________________________________________________________________
💵 Need Investor-Friendly Financing? This is who I trust → https://www.coachcarson.com/bryan
🏠 TurboTenant – Streamline Your Property Management for Free: https://www.coachcarson.com/turbotenant
📱 DealMachine – Software to help you buy more real estate deals: https://www.coachcarson.com/dealmachine-pod
Transcript
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| 0:00.0 | Most people think that cash flow comes from spreadsheets and smart analysis, and those definitely help. |
| 0:04.8 | But what if I told you that your biggest cash flow boost might come from a single, uncomfortable |
| 0:09.6 | conversation? The kind of conversations that make your palm sweat, that make your stomach |
| 0:13.5 | twist, but also the kinds of conversations that get results. In this Coach's Corner episode, |
| 0:18.4 | let's talk about those sweaty palm conversations that change everything. |
| 0:21.6 | Hey, everyone. My name is Chad Carson. You can also call me Coach Carson. And in this channel, I teach you how to use real estate investing to become financially free so you can spend your time doing more of what matters. |
| 0:30.6 | So I have a single motivation for this episode and why I wanted to share it with you. As I think back about my 22 years in real estate investing, |
| 0:42.0 | almost every single good thing, when I made cash flow, when I made money, when I built profit in real estate investing in my business, it came on the other side of a sweaty palm |
| 0:47.7 | conversation. So these difficult conversations. And I want to tell you a few stories about how |
| 0:52.4 | that's played out in my business, just to give you some examples. |
| 0:54.6 | And I'm going to give you a couple of ideas on how you can approach your own sweaty palm conversations. |
| 0:59.8 | And so recently, I was reminded of a pattern this happened over and over and again in my 22 years of real estate investing. |
| 1:06.7 | And it's this, is that I look at a property and often I'm talking directly to a seller, like I send out letters or I just like reach out to a seller when I see a property this vacant or that I like in a location. Sometimes though, it's through a real estate agent. In this case, I had two different situations. One through a real estate agent and another property that I had reached out directly to the seller from a referral from somebody else. In both cases though, the common theme was I looked at these properties, they were asking one |
| 1:31.7 | price and let's just call it like $290,000 in one case. The other case was $390,000. So like almost |
| 1:39.1 | 400,000 and almost 300,000. My price that I was willing to pay was about $110,000 less in one case, |
| 1:46.2 | about $120,000 less. So a huge, huge golf between what I'm willing to pay and what the seller's |
| 1:53.5 | asking. And you know, my initial reaction to that is like, ah, that's uncomfortable. Let's just |
| 1:58.7 | walk away because the little voice in my head says, |
| 2:01.3 | if you make this offer, they're just going to reject it. In fact, they might even get mad, and let's just avoid situations where you're going to make people mad or uncomfortable, and let's just move on to something else. There's got to be an easier way. That's what this little voice in my head is saying. But what I have found over and over again, my business is that I need to make that offer. |
| 2:18.1 | That is a sweaty palm conversation. |
| 2:21.2 | So with the seller, I ended up meeting with him and we had a conversation. |
| 2:25.5 | I had to think about how do I present this in a way that number one doesn't make him mad, |
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