RMDs When Your IRA Is Mostly Illiquid: How to Plan Ahead So You’re Never Forced to Sell
One of the best things about a self-directed IRA is that your retirement dollars can work in assets you know and believe in, like rental property, private notes, or a stake in a business. But once you reach RMD age, those same assets raise a practical question: where...
Taking Your RMD In-Kind: How to Distribute Real Estate, a Note, or an LLC Interest Instead of Cash
If your self-directed IRA owns a rental property, a private note, or a stake in an LLC, your required minimum distribution (RMD) can feel like a puzzle. The IRS expects a distribution every year, but your retirement dollars aren't sitting in a money market fund...
Contribution Season: How to Make the Most of Every Dollar Before Year-End
There's a quiet irony in how most people treat retirement contributions. They'll spend hours analyzing a single investment, comparing properties, scrutinizing a note, running returns to the third decimal. Then they'll fund their retirement account almost as an...
90 Days Out: Your Q4 Game Plan for a Stress-Free Year-End
Right now, the end of the year feels comfortably far away. The holidays are an abstraction, December 31 is a rumor, and the deadlines that will feel urgent in ten weeks feel like nothing at all today. That gap, between how far away year-end feels and how fast it...
Building With People You Trust: Investing Alongside Family and Partners
Some of the best investing stories aren't about a single person and a spreadsheet. They're about people. A husband and wife who built a portfolio at the kitchen table. A parent and an adult child walking a property together, one bringing decades of experience, the...
Restricted Stock Deserves Attention Before Year End
Executives and key employees often receive stock-based compensation in addition to salaries and bonuses. If restricted stock is part of your compensation, considering the potential tax consequences well before December 31 is a good idea. You may have decisions to make...
The Deal You Almost Did: Why Your IRA Might Be Your Best Untapped Capital
Every experienced investor has one. The deal that got away. The property that was priced right, in the right area, at the right moment, and you had to pass. Not because you didn't see the opportunity, you saw it clearly, that was the painful part, but because the...
UBIT Explained: The Tax Most Self-Directed Investors Have Never Heard Of
Most people open a self-directed IRA for a simple, appealing reason: tax advantages. The account grows tax-deferred, or in a Roth, potentially tax-free. So it comes as a genuine surprise to many investors that a tax-advantaged account can, in certain specific...
Why Fair Market Valuations Matter More Than You Think
If you hold stocks in a retirement account, you never think about what they're worth. The market decides, second by second, and your statement just tells you the number. It's automatic, invisible, and effortless. Self-directed investors don't get that luxury, and...
The 3 a.m. Test: What Kind of Investor Do You Actually Want to Be?
Here's a test that cuts through more financial noise than any spreadsheet ever will. Imagine it's 3 a.m. Something has gone sideways with one of your investments, a tenant issue, a market wobble, a deal that stalled. You're awake, staring at the ceiling. Now ask...