Create a Real Strategy to Build Predictable Wealth with Jeremy Roll

Create a Real Strategy to Build Predictable Wealth with Jeremy Roll

On my podcast Accredited Investors Only, I sat down with Jeremy Roll, an accredited investor who’s been living off passive real estate income since 2007. Jeremy’s approach is pragmatic and conservative: he prioritizes predictable cash flow over headline-grabbing upside, diversifies across asset classes and operators, and makes decisions with cycle timing in mind. Below, I summarize the conversation, highlight the lessons that matter for passive investors, and share the specific criteria Jeremy uses when he commits capital.

Jeremy’s background and why predictability matters

Jeremy grew up in Montreal, earned an MBA from Wharton, worked in corporate roles at Toyota and Disney, and began investing passively in syndicated opportunities in 2002. By mid-2007, he had rotated his portfolio into cash-flowing assets and left corporate life. Today, he lives near Newport Beach and relies on investment cash flow to cover living expenses.

“I trade control for diversification as a passive investor.”

“I live off the cash flow. I want to go to sleep tonight, wake up tomorrow, and not much has changed.”

That mindset explains why he seeks stability—80–100% occupied stabilized properties are his preferred starting point, and he’s intentionally hyper-diversified: over 60 active LLCs today and 150–200+ across 23 years.

How Jeremy selects asset classes

Not all commercial real estate behaves the same. Jeremy narrowed his A-tier asset classes for predictability:

  • Mobile home parks
  • Multifamily apartments (stabilized, high-occupancy)
  • Self-storage

He avoids asset classes that feel harder to forecast over a 10-year horizon: hotels, many office plays (since about 2015), and single-tenant industrial deals unless the tenant is essentially immovable (e.g., an airport FedEx-type facility). He looks for different occupancy targets by asset class—90%+ for multifamily and an optimal 88–92% occupancy for self-storage (a sign operator is optimizing revenue through dynamic pricing).

Cycle playbook: when to sit and when to act

Jeremy’s investing track record maps to macro cycles:

  • 2002–2008: learning and experimenting across asset classes
  • 2009–2016: broad opportunity set after the financial crisis
  • 2013 onward: selectively dropped apartments when cap rates compressed
  • 2017–2020: defensive — sold over 30 assets as he anticipated tightening

As of early 2025, Jeremy is the most on the sidelines he’s been since 2007. Two items drive his re-entry decision:

  1. Clear signals on the macro front: he watches the yield curve (inversion vs. uninversion) and looks for roughly 18–24 months of un-inversion/flattening to change his recession view.
  2. Positive leverage on reasonably strong assets: he wants to see market-rate deals in A−/B+ properties generate positive leverage by at least ~100 basis points versus treasuries—no negative-leverage floating-rate bridge loans for his core buys.

He favors fixed-rate, longer-term financing for predictability.

Vetting sponsors: alignment, conservatism, and track record

For a passive investor, the operator matters as much as the asset. Jeremy looks for sponsors who:

  • Are conservative and underpromise/overdeliver
  • Focus on one (at most two) asset classes and have a meaningful track record in that niche
  • Prefer in-house property management (not a strict rule, but a preference)
  • Have meaningful co-investment—ideally 5–10% (but he’s flexible based on size and sponsor resources)
  • Are financially capable and mentally willing to step up in a crisis

He’s wary of flashy marketing, constant deal advertisements, and sponsors who chased volume aggressively during frothy years—he prefers sponsors who showed discipline or sat on the sidelines when deals got too expensive.

“I want someone who’s conservative like me. I prefer people who underpromise and overdeliver.”

Deal structure preferences

Jeremy’s practical guardrails for structure include:

  • Preferred return target: roughly 7–8% as a baseline for his investments (subject to cycle and deal specifics)
  • Equity splits: typically in the 75/25 to 60/40 LP/GP range; 50/50 only for exceptional, high-work deals with top sponsors
  • Co-investment: prefers sponsors to have skin in the game (5–10% typical) but understands large sponsors can’t always place 10% on every deal
  • Return of capital vs. profit split: flexible—Jeremy values alignment and is comfortable with profit splits as long as the economics are fair and the sponsor is incentivized to perform

He avoids deals where the sponsor’s economics feel tilted beyond the point of alignment (e.g., sponsor getting most upside while investors shoulder most downside).

Two real-life lessons: what can go wrong and how to mitigate

Jeremy shared two instructive failures and the lessons they taught him.

1) Foreclosure triggered by a single external event

A 303-unit student property—historically 97–100% occupied—dropped to ~65% when the city closed the campus bridge for repairs ahead of the school year. The loan was due that fall, and the bank chose to demand the property rather than extend—result: foreclosure.

Lessons:

  • Even stabilized assets have “domino” risks: multiple unlikely events can cascade.
  • Diversification is essential because you can’t eliminate rare 1% risks.
  • Operator character matters: the sponsor personally absorbed losses and later transferred investors into another property—demonstrating why a sponsor’s ability and willingness to help matters.

2) Partner disputes and managerial gaps

A Memphis single-family portfolio (rehab/tenant/sell strategy) suffered when the two active partners left and left operations to a back-office partner who lacked experience and integrity. Jeremy and others negotiated a management change and ultimately recovered to roughly breakeven.

Lessons:

  • Vet every managing member—even those who seem secondary. Roles can change.
  • Again: diversification reduces the impact of operator-specific failures.
  • Sponsors with personal skin and financial capacity to support the deal can materially change outcomes.

Advice for new passive investors

Jeremy’s practical guidance for someone just getting started:

  • Start with one asset class you understand—your lived experience is a huge advantage. If you grew up in a mobile home park, learn that niche. Many start with apartments because they’re familiar and plentiful.
  • Learn underwriting fundamentals (revenue drivers, expense ratios, break-even occupancy) and compare many deals—volume of review equals speed of learning.
  • Don’t rush because of fear of missing out. Sometimes waiting for the right macro entry point is the best move.
  • Be honest about your goals: if you depend on cash flow, prioritize predictability over upside. If you want growth, accept different risk parameters.

Where Jeremy holds dry powder

Right now, Jeremy parks cash in short-term U.S. Treasuries (3–9 month maturities rolled over) rather than money market or bank accounts. It offers slightly better yield and safety in his view, and it’s a straightforward way to sit on capital while waiting for favorable market signals.

Five key takeaways

  • Predictability is power: If you live off returns, stability beats speculative upside.
  • Diversify, because you can’t control everything: External 1% risks exist; spread them across asset classes, geographies, and operators.
  • Alignment with sponsors matters: Conservative operators who have skin in the game and a track record are worth a premium.
  • Cycle timing isn’t optional: Watch yield curve behavior and look for positive leverage on market-rate deals before committing bulk capital.
  • Patience is an active decision: Sometimes the smartest move is to wait and preserve buying power.

How to connect with Jeremy

Jeremy welcomes conversations with experienced investors and peers. You can learn more or reach out via his site at jrollinvestments.com.

Final thoughts

Jeremy’s approach is a reminder that investing isn’t only about finding the “next hot” market or sponsor—it’s a discipline of alignment, conservative underwriting, and cycle-aware patience. Whether you’re building passive cash flow to live on or layering cash-flowing assets into a broader portfolio, his rules—focus on predictability, vet operators, diversify, and wait for positive leverage—are practical guardrails that help preserve capital and deliver reliable income over decades.