Author: Terence Critchlow

Most investors who transition from residential to commercial real estate do so because they are looking for scale. A single multifamily syndication can deploy more capital, generate more cash flow, and require less per-dollar management effort than a portfolio of single family rentals assembled over years. Commercial real estate makes that scale accessible, but it…

Most people think of real estate as a single investment category. When the topic arises, the conversation usually defaults to one image: buying a rental house and collecting monthly rent. This picture represents only a narrow slice of an asset class far more varied than most investors appreciate. Broadly speaking, you can break real estate…

Outside of depreciation, the 1031 exchange is one of the most favorable tax treatments available to real estate investors. Named for Section 1031 of the Internal Revenue Code, a 1031 exchange allows an investor to sell a property and, if certain rules are followed, to roll any gains from that property into a newly purchased…

If you spend enough time around real estate investors and ask enough questions, eventually the topic of depreciation recapture emerges. This is a subject you need to understand if you want to avoid an unpleasant surprise when your deal closes and the tax bill arrives. As you likely know, one of the significant advantages of…

The Science of Scaling by Benjamin Hardy and Blake Erickson offers a compelling framework for entrepreneurs who want to scale their businesses but struggle to identify the path forward. While written primarily for business owners, the core principles apply to building an investment portfolio capable of generating the passive income needed to break paycheck dependency.…

People often use the terms saving and investing interchangeably. This creates real problems. When you treat fundamentally different concepts as the same thing, you make decisions based on faulty assumptions about risk, return, and control. Understanding the distinctions between saving, investing, and speculating is not academic. It is the foundation for building a portfolio that…

Through consulting calls and networking conversations with newer investors, one pattern emerges consistently. Many investors lack clarity about what they are looking for in a deal. Some pursue impossible deals: 30% IRR, 10% cash-on-cash returns, complete liquidity, and zero risk. These opportunities do not exist. If they did, institutional investors would jump on them before…

As 2025 draws to a close, I reflect on a year defined by meaningful connections and growth. While it may be cliché to acknowledge, the most valuable moments this year emerged from relationships, including my ongoing conversations with many of you. Highlights Several highlights stand out as I look back on 2025. I began publishing…

As the year draws to a close, this is the natural moment to pause. To reflect on what you have accomplished over the past twelve months. To consider what you want to create in the year ahead. Before you rush into setting New Year’s, I suggest you first consider the question: What would you do…