Newsletter Archive

I recently re-read Extreme Ownership by by Jocko Willink and Leif Babin as part of the Money Mental Book Club. I liked it even better the second time. The core thesis of the book is simple to state and difficult to practice. To succeed, a person must take complete ownership of their current situation, treat…

Your investment thesis tells you what you are looking for and how much you need to invest to generate the cash flow you need to reach your goals. Building your portfolio is where that plan becomes real, and where patience separates a strong outcome from a costly one. Continuing the example from the previous chapter,…

A single $100,000 investment will not make you financially free. This is an extremely important lesson every passive investor must accept. 99.999% of the time, a single investment of $100k will not provide you financial freedom (the exception being an early investment in a unicorn opportunity). Too many new investors believe that a couple of…

Breaking your paycheck dependency (BYPD) can seem like a daunting task. You have defined your investment thesis and know what you want to accomplish. The people you surround yourself with will determine how quickly you get there. That is why the next step is finding the right room: a group of people who have already…

As someone who focuses on passive income investing, I receive regular questions about real estate crowdfunding platforms such as Fundrise and CrowdStreet. The appeal is easy to understand. These platforms market deals with low minimums, often well below the $50,000 to $100,000 typically required to participate in a syndication. They claim to vet sponsors before…

Most investors understand that diversification matters and that having a single asset in their investment portfolio is extremely risky. Fewer understand what it actually means to be well diversified. Holding a collection of technology stocks is not diversification. Owning several apartment buildings in the same city is not diversification. True diversification operates across four distinct…

Most personal finance books operate from the unspoken assumption that financial wealth is the only kind worth building. They teach you to optimize your portfolio, minimize your tax burden, and compound your returns — useful tools, all of them. What they rarely ask is whether financial wealth can deliver the life you are trying to…

Identifying the type of property is only one way to break out asset classes. There are also a number of cross-cutting strategies that can be used independent of property type. These strategies cut across all asset classes and shape the deal structure, return profile, and cash flow characteristics of any specific investment. Two investors can…

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…

Last week I was talking to someone who is struggling to get started in syndications. Conceptually, they understand the attraction of getting cash flow from an investment while that investment continues to appreciate in value. But they are having a hard time making a decision on what to invest in. They asked the question: “If…

This week, Amazon announced layoffs affecting 14,000 employees. These are not underperformers or redundant workers. They are people who show up every day, contribute meaningfully to the company mission, and believed their positions were secure. Having spent over a decade at Amazon myself, I understand the shock and uncertainty these individuals now face. But this…

As most of you know by now, I am a strong advocate for investing in syndications. After 30 years of studying real estate investing and transitioning from active property ownership to passive investing, I credit my syndication investments with allowing me to retire just six years after I began investing in them. However, you may…

Assuming that the sponsor has passed your review [1] and the property meets your investment criteria [2,3],  you have reached the final steps in your due diligence journey. The opportunity looks promising. The sponsor may be encouraging you to commit quickly. You may feel excitement about the projected returns. This is precisely when you must…

You have identified sponsors you trust [1] and refined your investment thesis to filter opportunities that align with your goals [2]. Now comes a critical juncture: evaluating the specific property that will house your capital for the next five to seven years. While your sponsor vetting process has eliminated the majority of deals crossing your…