Create a Real Strategy to Build Predictable Wealth with Jeremy Roll | 038

What does it take to succeed as a passive investor in real estate for over two decades? In this episode, I sit down with Jeremy Roll—an incredibly seasoned accredited investor who’s been living off passive income since 2007. Jeremy shares how he transitioned from the corporate world to full-time investing, why he prioritizes predictability over upside, and the thoughtful strategies he uses to diversify across asset classes, geographies, and operators.

We dig deep into how Jeremy evaluates deals, the recession signals he’s watching for, why he’s currently on the sidelines, and what makes a great operator. Whether you’re an experienced investor or just beginning your journey, this episode is packed with insights that will help sharpen your approach to passive investing.

Episode Highlights:

[0:00] - Jeremy’s path from Wharton MBA to full-time investor

[2:11] - Trading control for diversification and what that means in practice

[5:34] - Differences in U.S. vs Canadian real estate markets and legal systems

[10:16] - Why the dot-com crash pushed Jeremy toward cash-flow-focused real estate

[14:16] - Top asset classes Jeremy favors: mobile home parks, apartments, and self-storage

[17:24] - How he navigated past economic cycles and what he’s watching now

[22:03] - Positive leverage explained and why it’s key to his return

[23:19] - Vetting operators: the red and green flags Jeremy looks for

[26:46] - Jeremy’s candid views on the rise of sponsor education programs

[29:02] - Social media and sales tactics: how they influence Jeremy’s trust in sponsors

[34:41] - Advice for new passive investors on choosing their first asset class

[36:07] - Deal structures, sponsor splits, and what Jeremy views as fair compensation

[40:25] - What can go wrong: two real-life investing lessons from failed deals

[48:04] - Final reflections: why waiting to invest can sometimes be the smartest move

5 Key Takeaways:

1. Predictability Is Power – Jeremy’s entire strategy centers on stable, predictable cash flow—something he values far more than high-risk, high-reward upside.

2. Diversification Over Control – He diversifies across asset classes, geographies, and sponsors to mitigate risks, acknowledging you can’t eliminate them entirely.

3. Watch for Recession Signals – Inverted yield curves and consumer sentiment are among the key indicators Jeremy watches before jumping back into the market.

4. Alignment with Sponsors Is Critical – Jeremy avoids flashy operators and seeks those who are conservative, experienced, and invested alongside their LPs.

5. Patience Pays Off – Jeremy stresses that sometimes the best decision is to sit tight and wait for the right market conditions to return—don’t invest out of urgency.

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