AI Summary
5 min readIn 2026, Dave Meyer and Henry Washington are selling rental properties. They are also buying them. The apparent contradiction is the point: selling is not surrender, it is a strategic lever. Both hosts are in what they call the "harvest phase" of their investing careers, and they argue that the buy-and-hold-forever dogma is unrealistic. The episode is a calm, data-driven case for treating selling as a normal part of portfolio management, not a sign of failure.
The Harvest Phase Framework
The central framework of the episode comes from investor Chad Carson, who describes three stages of a real estate career: start, growth, and harvest. Both hosts are entering the harvest phase. Dave Meyer, at 38, says he no longer wants to manage old, maintenance-heavy properties out of state. He wants a "lower headache portfolio" that aligns with his current lifestyle, not the one he had at 25. Henry Washington uses a similar three-bucket model: growth, stabilization, and protection. For him, protection means paying off assets so he can leave income-producing properties to his children. He has done the math on exactly how many paid-off properties he needs and is selling assets to free up cash to pay down debt on the ones he wants to keep. The core message is that your portfolio should serve your life goals, and those goals change over time.
Return on Equity and the "Vibes" Test
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What you'll learn
- 1 (00:00) **Selling Rentals in 2026** - Henry Washington announces he is listing properties in his personal portfolio, but clarifies he is also buying, framing selling as a strategic tool rather than a panic move.
- 2 (04:08) **The "Harvest Phase" of Investing** - Dave introduces Chad Carson’s three-stage framework (start, growth, harvest) and explains he is entering the harvest phase.
- 3 (06:33) **Henry’s Three-Bucket Framework** - Henry describes his own version: growth, stabilization, and protection (paying off assets).
- 4 (10:33) **Are You Selling Because of Market Conditions?** - Both hosts address the elephant in the room: is this a market-timing play?
- 5 (13:35) **Trigger Points: When to Sell a Rental** - Dave and Henry outline the key signals that a property should be sold.
- 6 (24:29) **Selling Headache Properties** - Both hosts share real examples of selling properties that cash-flowed but were a pain.
- 7 (26:19) **Should New Investors Fear Buying from Old Landlords?** - The hosts address whether buying from experienced sellers is risky.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
We’re selling off rental properties. Nope, that’s not clickbait; we’re actually getting rid of cash-flowing rental properties from our real estate portfolios.
But why? And why now?
Is there a market crash we fear is coming? Do we think this is the peak of real estate? Have we finally decided to listen to the social media doomers who keep telling us it’s another 2008? Not quite. Instead, our reasoning behind selling might make a lot more sense than you think. In fact, after you listen to this episode, you might decide to sell some rentals.
So, what are we doing with the money? Are we going to sit on cash, pay off properties, or retire early? Both Dave and Henry have different reasons for selling, but both agree there’s one thing you should do (at least twice a year) to see whether you should sell properties in your portfolio.
Thought you were supposed to “hold forever,” as many of the traditional real estate investors have told you? We have proof that selling can often make you much wealthier than holding—here’s how.
In This Episode We Cover
Why we’re selling parts of our rental property portfolios in 2026
Signs you should sell a rental instead of holding, renovating, or paying it off
What we’re going to do with the money from our property sales
Is the market too risky to hold real estate right now? (We may buy even more)
The one thing every investor should do (at least) twice a year to make the highest returns
Buying from landlords? Great deal funnel or overpriced properties?
And So Much More!
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