Get Paul Shannon's Book, Both Sides of the Table: https://www.amazon.com/dp/B0H4W5D288?spcref=PUBLISHED_PREORDER_LIVE
This Episode
Paul returns to PassivePockets to discuss his new book, Both Sides of the Table, and the lessons he has learned as an LP, fund manager, and GP. He and Chris unpack the difference between being a “syndication consumer” and a true capital allocator, including why newer investors often get pulled in by polished decks, urgency-driven marketing, and projected IRRs without fully understanding the downside.
Paul explains how he evaluates market cycles, why timing still matters even if you can’t perfectly call the bottom, and how he thinks about toggling between aggressive and defensive portfolio positioning. The conversation also gets into sponsor character, fraud risk, debt structure, and the hard lessons that come from deals where communication breaks down or capital is misused.
Chris and Paul also dig into practical due diligence: what can disqualify a deal in the first five minutes, why metrics like yield on cost and IRR partitioning matter more than flashy projected returns, and why the debt stack can make or break an otherwise strong-looking deal. For LPs who want to get more serious about passive investing, this episode is a reminder that the default answer should be “no” until the deal, sponsor, structure, and market all earn your confidence.
Key takeaways:
How Paul’s experience as an LP, GP, and fund manager shaped Both Sides of the Table
Why passive investors need to shift from consumer behavior to allocator behavior
How market cycles influence when to lean in, pull back, or hold more cash
What fraud, poor communication, and weak sponsor character can teach LPs
Why debt structure, yield on cost, and downside protection matter more than projected IRR
How Paul filters deals quickly and decides which ones deserve deeper diligence
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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. 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 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.
