Author: Terence Critchlow

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…