3 Things We’re Doing in 2026 to (Actually) Retire with Rentals

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Jan 6, 2026

As 2026 begins, the hosts share fresh real estate resolutions to achieve early retirement. Kathy plans to leverage AI for optimizing her portfolio, aiming for a 10% cash flow boost. Conversely, Henry opts for stability over scaling, focusing on debt reduction and protecting assets for future generations. Dave outlines his 'End Game' strategy, envisioning a low-debt rental portfolio that brings joy. The discussion dives into the importance of finding balance and enjoying the journey beyond just financial goals.

29:04

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ADVICE

Optimize Portfolio With AI

Use AI to analyze your full portfolio including bank statements, insurance binders, and contractor costs to find underperforming assets.
Act on findings by renovating, 1031 exchanges, or repurposing idle assets to boost cash flow by ~10%.

insights

INSIGHT

AI As A Virtual Business Consultant

AI can act like a business consultant by ingesting operational details and suggesting optimizations across teams.
Early adoption of AI in estate and portfolio management can reveal blind spots most owners overlook.

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ADVICE

Double-Check AI Outputs

Test multiple AI platforms (Claude, Gemini, GPT) and double-check outputs for accuracy.
Use AI for research and optimization but verify results before making financial decisions.

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Opening: New year investing mindset

00:45 • 2min

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Kathy: Dive into AI for portfolio optimization

02:33 • 2min

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AI tools, limits, and validation

Henry: Shift to stabilization and protection

10:38 • 5min

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Backing into goals and required projects

15:37 • 2min

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Why paid-off assets matter for legacy

Dave: Building the 'End Game' portfolio

24:45 • 2min

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Balancing work you love and eventual retirement

27:11 • 3min

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Closing: Share your resolutions

• Mentioned in 13 episodes

Scaling Smart

Tyler

2026 is finally here! And if you can still read this sentence without seeing double, you’ve made it!

But this year, things are going to be a little… different. We usually talk about the best places or strategies for buying rentals, but we’re going on a bit of a detour to start the year by discussing our real estate resolutions, all of which will actively help us retire early. Want to retire with rentals, too? This is the episode for you, and we’re sharing the strategies we’re using in 2026 to get there.

Kathy shares a new way she’s optimizing her real estate portfolio, with the goal to increase cash flow by 10% on her current portfolio (not buying more rentals!). Henry takes an opposite approach to most investors, opting not to scale his portfolio and instead doing something much safer. Dave details his “End Game”—the ultimate real estate portfolio for early retirement.

You can copy these experts’ strategies in 2026 to retire with rentals, too!

In This Episode We Cover

How to use AI to optimize your portfolio and find the cash flow blind spots where you’re losing potential profits

Stop scaling? Why Henry is making moves to pay off some rentals instead (and whether you should, too)

Building your “End Game” portfolio to retire with rentals you actually enjoy owning

The three “buckets” of investing and a sign you’ve already outgrown yours (it could cost you)

Henry and Dave’s real goal that has nothing to do with real estate (can you help them out?)

And So Much More!

Links from the Show

Join the Future of Real Estate Investing with Fundrise

Join BiggerPockets for FREE

Find an Investor-Friendly Agent in Your Area

Should You Pay Off Your Mortgage Early or Invest?

Dave's BiggerPockets Profile

Henry's BiggerPockets Profile

Kathy's BiggerPockets Profile

Grab Kathy’s Book, "Scaling Smart"

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