PassivePockets: The Passive Real Estate Investing Show

The hosts delve into their latest investments and strategies, discussing a shift towards debt funds and the importance of transparency in deals. Jim shares insights on new allocations in healthcare and coffee, while Paul outlines a promising Indiana multifamily turnaround. They emphasize the need for thorough checks on fee structures and the significance of using investing clubs to vet new managers. Red flags in hotel conversions are dissected, highlighting potential pitfalls like phantom equity and misaligned waterfalls. It's a vital guide for savvy investors.

Host Paul Shannon sits down with Gino (of Jake & Gino) to trace the path from family pizza shop to operating ~1,900 units with no outside equity. Gino breaks down why they paused syndications after 2019, how “PPU—profit per unit” drives their buy/hold decisions, and the exact LP diligence framework he wishes he’d had before losing money as a passive. They dig into today’s tighter credit, catching-a-falling-knife rent/occupancy dynamics, and why longer debt runways and operator fit matter more than ever. Key Takeaways: The LP Framework: Jockey (sponsor) → Saddle (alignment of interests) → Horse (deal: buy right, manage right, finance right) Why they exited syndications: control, long-hold strategy, and avoiding the “feed the beast” pressure—investor expectations make investors your de facto bosses Diligence like a pro: visit the asset, run the PPM through AI, then spend an hour with a securities attorney before wiring a dime Operate for durability: target $200–$400 PPU, prefer vertical integration, and secure ≥5-year debt to bridge cycles Match strategy to you: know your relationship with money, stagger commitments (the “conveyor belt”), and choose sponsors aligned with long-term holds if that’s your goal Disclaimer The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgment and consult with qualified advisors before investing. You should only risk capital you can afford to lose. Remember that past performance is not indicative of future results. This podcast may contain paid advertisements or other promotional materials for real estate investment advisers, investment funds, and investment opportunities, which should not be interpreted as a recommendation, endorsement, or testimonial by PassivePockets, LLC or any of its affiliates. Viewers must conduct their own due diligence and consider their own financial situations before engaging with any of the advertised offerings, products, or services. PassivePockets, LLC disclaims all liability for direct, indirect, consequential, or other damages arising out of reliance on information and advertisements presented in this podcast.

Paul Shannon sits down with lender-turned-operator Ryan Duff to unpack how lenders really size risk and how LPs can use the same lens. Ryan financed ~$4B+ across cycles before launching Seaport, and he explains why trailing 3–6 month economic occupancy (physical vacancy + concessions + loss-to-lease) tells you more than any glossy OM. Join us to dive into debt yield, DSCR reality vs. pitch decks, the broker-driven “falsified inputs” fiasco and subsequent lender cleanup, and why he prioritizes local, vertically integrated operators with disciplined leverage and cash buffers. Key Takeaways: Underwrite like a lender: focus on economic occupancy (vacancy, concessions, loss-to-lease), not just IRR/EM multiples Expenses are mostly knowable; deals are won/lost on the top-line and honest reporting of rent integrity Debt terms follow the inputs: DSCR, debt yield, and recent trailing performance drive survivability Protect yourself: vet the GP first (local, cycled deals, vertical ops, conservative leverage, transparency) Industry shift: tighter lender verification post-froth (less room for “massaged” rent rolls), more equity skin-in-the-game Bridge debt isn’t evil, operator fit + execution speed must match the capital structure Disclaimer The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgment and consult with qualified advisors before investing. You should only risk capital you can afford to lose. Remember that past performance is not indicative of future results. This podcast may contain paid advertisements or other promotional materials for real estate investment advisers, investment funds, and investment opportunities, which should not be interpreted as a recommendation, endorsement, or testimonial by PassivePockets, LLC or any of its affiliates. Viewers must conduct their own due diligence and consider their own financial situations before engaging with any of the advertised offerings, products, or services. PassivePockets, LLC disclaims all liability for direct, indirect, consequential, or other damages arising out of reliance on information and advertisements presented in this podcast.

Host Chris Lopez and Paul Shannon talks with securities attorney Mauricio Rauld about the compliance landmines that trip up syndicators and how LPs can protect themselves. Mauricio shares why he exited his law firm to focus on education and “in-between” guidance (before the PPM), what an SEC lawyer actually does, and the real differences between 506(b) and 506(c). They cover LP recourse (rescission), how to diligence sponsors and structures (co-GPs, capital raisers, funds-of-funds), why “investment clubs” aren’t a loophole, and where regulations may head next (accreditation changes, a possible finder’s rule). Key Takeaways: Compliance isn’t “just a PPM”: most mistakes happen pre-attorney (emails, websites, social posts) 506(b) vs 506(c): advertising and accreditation verification are the two big pivots LP protection: if securities laws are violated, rescission can force capital + interest returned Capital raising rules: no transaction-based comp, substantial duties, and primary role ≠ fundraising Trends to watch: FoF adviser/Investment Company Act issues, “investment club” myths, broader accredited paths and a potential finder rule Disclaimer The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgment and consult with qualified advisors before investing. You should only risk capital you can afford to lose. Remember that past performance is not indicative of future results. This podcast may contain paid advertisements or other promotional materials for real estate investment advisers, investment funds, and investment opportunities, which should not be interpreted as a recommendation, endorsement, or testimonial by PassivePockets, LLC or any of its affiliates. Viewers must conduct their own due diligence and consider their own financial situations before engaging with any of the advertised offerings, products, or services. PassivePockets, LLC disclaims all liability for direct, indirect, consequential, or other damages arising out of reliance on information and advertisements presented in this podcast.

Host Chris Lopez sits down with Peter, an anesthesiologist who became an LP and then a GP, to unpack the career jolt that pushed him into real estate and the systems he built to bring more transparency and advocacy to LPs through Ascent Equity Group. Peter shares his first $5k crowdfunding check (and that unforgettable $47 distribution), lessons from launching in the tough 2021 vintage, and how his team handled rate/insurance shocks, lender work-outs, and communication when things got bumpy. We also dive into why he’s been using preferred equity in today’s market—including a 12.5–13.5% monthly-pay deal that returned capital in ~12 months and where he’s hunting now (hospitality, selective retail, and medical office) with a likely recession window following the Fed’s pivot. Key Takeaways: From OR to LP to GP: how a broken partnership promise sparked a plan for autonomy and passive income Preferred equity in practice: monthly pay, collateralized position, and why it’s a “right now” tool—not forever 2021 lessons: short-term debt + fast-rising rates/insurance = humility, capital infusions, and relentless communication Macro setup: Fed pivot → typical recession lag (~10–11 months) → prepare capital/relationships for distressed opportunities What’s next: multifamily fundamentals (supply pause, sticky demand), selective hospitality/retail, and a special eye on medical office Disclaimer The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgment and consult with qualified advisors before investing. You should only risk capital you can afford to lose. Remember that past performance is not indicative of future results. This podcast may contain paid advertisements or other promotional materials for real estate investment advisers, investment funds, and investment opportunities, which should not be interpreted as a recommendation, endorsement, or testimonial by PassivePockets, LLC or any of its affiliates. Viewers must conduct their own due diligence and consider their own financial situations before engaging with any of the advertised offerings, products, or services. PassivePockets, LLC disclaims all liability for direct, indirect, consequential, or other damages arising out of reliance on information and advertisements presented in this podcast.

The hosts dive into the Fed's recent 25 basis point cut and its limited impact on fixed versus floating debt in commercial real estate. They highlight a distressed 22-unit value-add property targeting impressive yields and discuss the shift towards private credit for enhanced risk-adjusted returns. A candid discussion on LP accountability explores fraud, operator errors, and market risks, while emphasizing the importance of community for smarter investing. Plus, insights on leveraging tools for tracking syndication investments.

Host Chris Lopez sits down with John Bowens, CISP of Equity Trust to demystify Solo 401(k)s for real estate investors. John explains who actually qualifies, how to stack contributions up to $70k/$77.5k/$81,250 (2025 limits) and use the “mega backdoor” to Roth, and why Solo 401(k)s can avoid UBIT on debt-financed syndications when IRAs often can’t. They get tactical on plan design- one bank account with clean source tracking, blending traditional + Roth into a single subscription (and later in-plan conversions), and exactly how to roll over or restate a plan without triggering a termination. John also breaks down spouse/child participation, controlled-group and W-2 pitfalls, and a real UBIT case study that shows how the right plan choice can save five figures in tax. Key Takeaways: Solo 401(k) eligibility: true self-employment income and no rank-and-file W-2s; spouse/partners OK, under-21 and part-time hour rules matter Higher limits + mega backdoor Roth: employee non-deductible → in-plan Roth conversion for bigger tax-free growth UBIT advantage: Solo 401(k)s are generally exempt from UDFI/UBIT on debt-financed real estate (IRAs are not) Simpler operations: one bank account, source tracking in software, and the ability to blend trad + Roth in one deal and convert later Do rollovers right: restate/transfer the plan (don’t “terminate”), mind Form 5500, and watch controlled-group attribution Disclaimer The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgment and consult with qualified advisors before investing. You should only risk capital you can afford to lose. Remember that past performance is not indicative of future results. This podcast may contain paid advertisements or other promotional materials for real estate investment advisers, investment funds, and investment opportunities, which should not be interpreted as a recommendation, endorsement, or testimonial by PassivePockets, LLC or any of its affiliates. Viewers must conduct their own due diligence and consider their own financial situations before engaging with any of the advertised offerings, products, or services. PassivePockets, LLC disclaims all liability for direct, indirect, consequential, or other damages arising out of reliance on information and advertisements presented in this podcast.

Matt Faircloth, co-founder of DeRosa Group and author of 'Raising Private Capital,' shares insights on diversifying real estate portfolios by adding branded hotels. He explains how hotels can provide immediate cash flow with higher caps, discusses the risks involved, and reveals strategies for 1031 exchanges. Moreover, he elaborates on his Houston hotel's financial structure and highlights overlooked markets in the Midwest for better yields. Get ready for practical advice on moving from active to passive investing without losing tax advantages!

Dan Handford, the founder of PassiveInvesting.com and a general partner in vast multifamily units, shares his journey from chiropractor to real estate mogul overseeing a billion-dollar portfolio. He reveals lessons learned from investing in over 80 LP deals and stresses the importance of transparency and steady communication. Dan discusses risk management strategies, including the shift towards private debt funds and the impact of rising interest rates on market dynamics. His insights on navigating current challenges and focusing on diversification are invaluable for aspiring investors.

Industrial syndicator Joel Friedland joins Paul Shannon to share 40 years of Chicago lessons and why he now buys with little to no debt. They break down a debt-light playbook, how that changes capital raises and returns, and the investor profile that prefers sleep-at-night income. Joel also details his off-market system, what makes a “perfect” small-bay building, and how he creates liquidity and plans succession. Key Takeaways: Debt-light strategy: target 0 to 30 percent LTV, current portfolio around 18 percent Buy box: Chicago small-bay under 40k sf, 7 to 8 percent entry yield, triple-net, strong geometry, docks, power Return drivers: cash coupon that grows with rent, long holds, depreciation and recapture awareness Sourcing and liquidity: door-to-door outreach, mini fund closes fast then syndicate, investor exits via assignments, 754 step-up, Rule 144 after 12 months Sponsor vetting: ask for a written succession plan and review loan docs, covenants, and recourse Disclaimer The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgment and consult with qualified advisors before investing. You should only risk capital you can afford to lose. Remember that past performance is not indicative of future results. This podcast may contain paid advertisements or other promotional materials for real estate investment advisers, investment funds, and investment opportunities, which should not be interpreted as a recommendation, endorsement, or testimonial by PassivePockets, LLC or any of its affiliates. Viewers must conduct their own due diligence and consider their own financial situations before engaging with any of the advertised offerings, products, or services. PassivePockets, LLC disclaims all liability for direct, indirect, consequential, or other damages arising out of reliance on information and advertisements presented in this podcast.