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

Jul 3, 2025

Chris Loeffler, CEO of Caliber with $2.9 billion in assets under management, discusses the present real estate market's rare opportunities. He emphasizes why commercial real estate is undervalued compared to the peaks of 2008, exploring conversions from distressed office spaces to multifamily units. Chris also highlights the changing landscape for investors, including the growing relevance of alternative assets and self-directed IRAs. This conversation is crucial for anyone interested in navigating today's real estate investments.

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ANECDOTE

Starting Real Estate in 2008 Crisis

Chris Loeffler shares he bought his first single family home in 2008 for $50,000 and sold it shortly after for $100,000.
This experience launched his career in distressed real estate investing during the financial crisis.

INSIGHT

2024 Market Mirrors 2008 Crisis

Commercial real estate values are currently at a bottom similar in size and speed to the 2008 financial crisis.
September 2024 marks a rare buying window as values hit lows and start their recovery phase.

ADVICE

Sell Residential, Buy Commercial

Sell your appreciating single-family rental properties while prices remain strong.
Reinvest those funds into discounted commercial real estate to capture better upside potential.

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In this insightful episode, Mat 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.

See the market chart Chris refers to at 03:22 — Download the Guide Here

00:00:00 – Welcome to Main Street Business Podcast
Intro to the episode with host Mat 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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