Why "We Monitor Our Borrowers" Isn't the Answer You Think It Is
Tuesday, October 27
Every debt fund will tell you they underwrite carefully and monitor their borrowers closely. I have never once heard a fund manager say otherwise. Which is exactly the problem. It's a claim that costs nothing to make and tells you almost nothing about whether it's true. I learned to stop acceptin...
Stop Checking Boxes on a Debt Fund. Start Grading the Numbers.
Tuesday, October 20
I've sat across from a lot of investors who did their homework on a debt fund and still got surprised later. Not because they skipped diligence, but because the diligence they did was built on a checklist, not a grading scale. The problem is checklists only give you a “yes” or “no”. Does the fun...
42+ Doors & My Cash Flow Was Still Unpredictable (And Here's My Fix)
Tuesday, October 13
For a long time I thought more doors was the answer. By 2019, I had forty-two single-family rentals, a multifamily portfolio, and enough years behind me to know exactly how much it took to keep all of it running. And my cash flow was still unpredictable. Not catastrophically. But enough to remin...
Why I Stopped Chasing Equity Deals (And What I Do Instead)
Tuesday, October 06
I used to pick deals the way most of us do. Best projected upside wins. Wire the money, check the sponsor's track record one more time, and wait three to five years to see if the plan worked at exit. I did that for years. Then in 2019, I actually looked at what that cash flow was made of. My deal...
The 5 Questions Nobody Asks Before Investing in a Debt Fund
Tuesday, September 29
Most investors evaluate a private debt fund the way they'd evaluate a stock. Check the return, skim the pitch deck, maybe glance at the track record, move forward. Almost nobody asks what happens to their capital if the fund itself runs into trouble. I've developed a personal standard for answeri...
You Have Built the Wealth. Here Is Why It Is Not Paying You Yet.
Tuesday, September 22
At some point in your work and investing journey, the question changes. For most of your career, it was how do I earn more? More clients, more revenue, a bigger practice, a better exit. You optimized for income, and it worked. The career grew. The business scaled. The portfolio built up. Then som...