PassivePockets: The Passive Real Estate Investing Show

Host Jim Pfeifer chats with real estate advisor Aleksey Chernobelskiy, who spent years on an institutional investment team overseeing billions of dollars in properties before shifting his focus to helping limited partners. Aleksey discusses the key lessons he’s learned under “big REIT” systems and how they apply to everyday passive investors navigating the often “Wild West” of syndications. You’ll hear why standardized metrics (like address, fees, and exit cap assumptions!) are so critical yet frequently missing from pitch decks, and how to interpret the elusive “sensitivity analysis” that many operators forget to include.Aleksey also lays out common mistakes he sees investors make, such as chasing big claims without verifying the operator’s experience or ignoring major red flags in the fine print. He and Jim dive into the sometimes tricky world of capital calls: when they might be a necessary lifeline, how to evaluate them like a brand-new investment, and why “we never do capital calls” might not be the reassurance some investors think it is. If you’re looking to sharpen your due diligence game, question operator assumptions, and understand the hidden pitfalls behind “good stories” in a pitch deck, this conversation delivers straight talk on raising your LP IQ.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 Logan Freeman (a.k.a. “Mr. Kansas City”) for a deep dive into the 18-year real estate cycle and how it shapes today’s market. Drawing on the works of economists like Fred Harrison and Phil Anderson, Logan explains why land scarcity and speculative credit often drive real estate booms and busts. He also highlights how investors can prepare for what he calls a “winter’s curse,” using historical cycles to spot new opportunities and avoid pitfalls. If you’re looking to navigate the next few years in real estate with an eye on both history and strategy, this conversation offers an essential roadmap.Today’s Episode Takeaways- The 18.6-Year Framework: Why land values, access to credit, and investor psychology create repeating upswings and contractions.- Ricardo’s Law of Economic Rent: How scarce land resources drive speculation and shape “winner’s curse” booms.- Historical Context: From 1993–2010’s cycle to the 2025–2028 outlook, including the impact of debt maturities.- Preparing for Opportunities: Why managing liquidity, fixing long-term debt, and maintaining strong cash flows are Logan’s focus.- Local vs. Macro: How city-level policy and development (like Kansas City’s rebounds) can differ from national trends – and what it all means for your strategy.DisclaimerThe 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.

Chris Carsley, a private real estate debt expert from Kirkland Capital Group, dives into the evolving landscape of non-bank lending. He discusses how traditional banks' retreat has allowed private lending to thrive, particularly through short-term bridge loans yielding attractive returns. Carsley emphasizes the importance of operational due diligence and understanding key risk factors like valuation and loan-to-value ratios. He shares insights into liquidity concerns and how private real estate debt can diversify an investment portfolio in today's volatile market.

Jim Pfeifer and Paul Shannon sit down with John Bowens of Equity Trust to break down the power of self-directed retirement plans for real estate investors. From the basics of what “self-directed” really means to the nuances of IRAs, HSAs, and Solo 401(k)s, John explains how you can unlock more flexibility and control in building your portfolio. Whether you’re investing in syndications, private lending, or direct ownership, learn the steps for opening a self-directed account, how to navigate leverage with UBIT/UDFI, and why a Solo 401(k) might offer key advantages (when you qualify). Plus, John dispels the myths around the tax complexity of self-directed deals and shares a simple framework to evaluate any potential investment.Today’s Episode Takeaways What “Self-Directed” Really Means: Why most standard IRAs don’t allow real estate—and how self-direction changes that. IRAs vs. Solo 401(k)s: Who qualifies, which offers higher contribution limits, and the unique tax perks. UBIT & UDFI, Explained: How leverage can trigger special taxes—and why it’s not always a deal-breaker. Choosing a Custodian: Key factors like years in business, transaction speed, fee models, and customer service. Strategic Framework: John’s 3-part approach (business sense, tax optimization, and lifestyle considerations) for any self-directed deal. Learn More from Equity Trust Website & Resources: TrustETC.com YouTube: Equity Trust Company for in-depth how-tos Or visit the PassivePockets website for additional content and materials DisclaimerThe 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.Contact Usjimpfeifer@biggerpockets.com

In this engaging discussion, Jeremy Roll, an experienced investor from Roll Investments, and Mauricio Rauld, a securities attorney at Platinum Legal, tackle the intricacies of Private Placement Memorandums (PPMs) from both limited and general partner perspectives. Jeremy highlights red flags and the importance of understanding cash call provisions, while Mauricio explains how PPMs protect operators and outline deal structures. Listeners will gain insights into negotiating terms and recognizing mismatched documentation, essential for informed investment decisions.

Clint Harris, a seasoned real estate operator, dives into the art of transforming underutilized properties into profitable ventures. He discusses the booming demand for self-storage among millennials, driven by changing consumer habits. Clint shares insights on 'cap rate arbitrage' strategies for cost-effective conversions and explores the potential of repurposing various distressed assets, from offices to hotel spaces. The conversation also highlights the challenges operators face and the essential metrics to ensure successful transformations.

Join John “Dr. Doom” Drachman, co-founder of Waterford Property Company, as he shares his keen insights on the multifamily market's evolution since 2022. He dives into why the anticipated distress never materialized, emphasizing the importance of stable, long-term investments over reckless flips. John highlights the impact of local knowledge on property returns, and why he advocates for 'boring' strategies like workforce housing. Discover the unique challenges of investing in states like California versus Texas, and gain valuable lessons for navigating today's market.

Jay Parsons, a rental housing economist, dives into multifamily market trends and what's ahead for 2025. He explains why demand remains robust despite record new deliveries and discusses the complexities of interest rates and local policies. Jay predicts a split between struggling C-class properties and stable A/B-class options. He reveals that Midwest markets are thriving, while the Sunbelt may soon bounce back. For passive investors, understanding these dynamics is crucial for navigating the changing landscape.

Investment expert Spencer Hilligoss from Madison Investing shares his expertise on sponsor vetting, emphasizing the importance of a robust network and personal referrals over ads. He introduces a five-part framework to evaluate a sponsor's track record, communication style, and values. Spencer explains why a sponsor’s personal balance sheet and past failures can be telling of their reliability. He also discusses the critical differences between investing for cash flow versus wealth building, offering practical questions to ask before committing funds.

We sit down with special guest Litan Yahav: the CEO and founder of Vyzer, an innovative virtual wealth management tool designed for passive investors. In this episode, Litan takes us behind the scenes of building a platform that helps you stay organized across multiple deals, GPs, and asset classes—while also giving us a sneak peek at how Vyzer uses aggregated (yet anonymous) data to identify top-performing operators. Get ready for game-changing insights on optimizing your time and improving your returns through smarter, simpler portfolio management.Today’s Episode Takeaways:- Litan’s journey from tech entrepreneur to passionate passive investor- A big announcement about free Vyzer access for PassivePockets members- Why “return on time” is just as important as ROI- Managing multiple syndications more efficiently with automation- Litan’s 2025 outlook on multifamily, private debt, mobile home parks, and moreWhether you’re already investing or just getting started, this episode is loaded with tips on finding the right balance between risk, reward, and your most valuable resource- your time.Don’t forget to subscribe and leave a review so you never miss out on future episodes covering the latest passive investing strategies, market insights, and more!PassivePockets Members get Vyzer for FREE (valued at $2,160): https://passivepockets.com/invest/vendors/Visit Vyzer: https://vyzer.co/Take our Survey: PassivePockets.com/SurveyDisclaimer: 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 judgement 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.Contact Us At:jimpfeifer@biggerpockets.com