#584 The Best Real Estate Opportunity Since 2010 — Featuring Chris Loeffler from Caliber

Main Street Business

In this insightful episode, Matt Sorensen sits down with Chris Loeffler, CEO of Caliber, to dissect the current state of the real estate market and why commercial real estate is presenting one of the best buying opportunities in over a decade. With over $2.9 billion in assets under management and development, Chris breaks down the macroeconomic and local market conditions creating value in distressed assets—especially in hotels, industrial, and multifamily sectors.

They explore how real estate investors can reposition capital, the shift from the traditional 60/40 portfolio, and how individual investors—accredited or not—can participate in today’s unique opportunities through direct deals or diversified funds. This is a must-listen for anyone managing a real estate portfolio, considering Opportunity Zones, or exploring how to use self-directed IRAs to tap into alternative investments.

00:00:00 – Welcome to Main Street Business Podcast
Intro to the episode with host Matt Sorensen and guest Chris Loeffler.

00:05:46 – Why Commercial Real Estate Is At 2008 Pricing
Market correction parallels to 2008 and why it's creating a rare buying window.

00:11:44 – Commercial vs Residential: Sell Homes, Buy Commercial
Strategic shift: Why residential might be peaking while commercial offers upside.

00:19:15 – Office Buildings to Multifamily: Deep Discount Conversions
Case study on converting distressed office properties into profitable multifamily.

00:27:42 – Hotel Industry: Supply Shortage, High Demand
Post-COVID hotel trends and why Caliber is building ground-up in key markets.

00:34:08 – Investment Options: Direct Deals vs Fund Structures
How investors can participate—accredited and non-accredited—with flexibility.

00:42:44 – Distressed Asset Opportunities and Strategy
Accessing off-market deals and why experienced operators have the edge.

00:49:03 – Opportunity Zones Becoming Permanent Tax Code
What’s in the new tax bill and how OZs can be a powerful capital gains strategy.

00:52:43 – Final Advice: Value and Cash Flow Focus
Chris’s core investment principle: buy below replacement cost and cash flow strong.

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Chapters

1. Welcome to Main Street Business Podcast (00:00:00)

2. Why Commercial Real Estate Is At 2008 Pricing (00:05:46)

3. Commercial vs Residential: Sell Homes, Buy Commercial (00:11:44)

4. Office Buildings to Multifamily: Deep Discount Conversions (00:19:15)

5. Hotel Industry: Supply Shortage, High Demand (00:27:42)

6. Investment Options: Direct Deals vs Fund Structures (00:34:08)

7. Distressed Asset Opportunities and Strategy (00:42:44)

8. Opportunity Zones Becoming Permanent Tax Code (00:49:03)

9. Final Advice: Value and Cash Flow Focus (00:52:43)