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Most LPs judge a deal by the projected returns.

But glossy pitch decks rarely tell you what really matters.

The pros know that the real risk lives in the operator and the assumptions—the places most investors never dig deep enough. Miss those, and you end up in a deal where the numbers don’t materialize, the communication dries up, and you’re stuck hoping someone else can land the plane.

On this episode of The Passive Income Playbook (on the Best Ever CRE network), Pascal sits down with Matt Picheny—Tony Award–winning Broadway producer, bestselling author of Backstage Guide to Real Estate, multifamily GP (16+ deals) and LP (28+ deals). Matt’s rare vantage point—coaching first-time sponsors while continuing to operate and invest himself—makes this a masterclass in thinking like a GP so you can invest like a smarter LP.

In this episode he breaks down:
→ How to vet sponsors beyond the pitch deck and spot red flags early
→ The underwriting assumptions that separate conservative from careless
→ Why today’s cycle may offer attractive entries if you can stomach the fear
→ Cap rates explained simply—and how they impact valuations
→ Lessons from his first LP deal that went sideways due to operator error
→ Fixed vs. floating debt, capital calls, and real-world investor communication
→ His Sun Belt value-add strategy and why he underwrites to worse exit cap rates than purchase

Whether this is your first syndication or your 15th, this conversation gives you a sharper checklist for sponsors, markets, and deals—so you can protect capital and compound wisely.

Chapters:
00:03 – Think Like an Operator: The LP Edge
01:20 – From Broadway to Buildings: Why Matt’s Lens Helps LPs
04:16 – The “Backstage Guide” Playbook: How Deals Really Work
08:36 – First LP Deal Went Sideways: What Operator Risk Looks Like
12:59 – Sponsor Diligence 101: Track Record, Assumptions, Communication
16:49 – Cycles & Sentiment: Why Unpopular Times Create Opportunity
21:12 – Debt Structure in Practice: Fixed vs. Floating (and Assumptions)
26:02 – Capital Calls & LP Alignment: Terms That Protect (or Hurt) You
33:04 – Conservative Underwriting: Exit Cap Discipline & Stress Tests
44:36 – Market & Strategy: Sun Belt Value-Add with Real Resident Wins