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...
The Fund Leverage Question in I Wish I Knew Before I Started Investing
Tuesday, September 15
I've been on both sides of this. I've helped raise capital, and I invest my own money alongside other people's in the same funds I help build. And there's one question I almost never hear investors ask, even the sharp ones, even the ones who've been burned before. Does this fund borrow against it...
The Lost S&P 500 Decade (And What It Taught Me About Compounding)
Tuesday, September 08
A few months ago, I sat down and ran a number I'd never actually calculated before. If you'd put $500,000 into the S&P 500 in January 2000, dividends reinvested, where would you be by the end of 2009? I guessed it would be flat. I was wrong. It was worse than flat. $454,416. Ten years, and yo...
How to Actually Evaluate a Passive Real Estate Deal
Wednesday, September 02
Over the past several years, a lot of investors learned a hard lesson. Deals that looked straightforward suddenly weren't. Interest rates moved fast. Financing costs rose. Insurance climbed. Rent growth slowed in plenty of markets. Deals that looked solid on paper started to struggle. For passive...
Why Smart People Stall Before Their First (or Next) Investment
Tuesday, August 25
If you're a high-income professional or business owner, this may feel familiar. You've done the work. You earn well. You save consistently. You understand that investing matters. And yet, capital sits. Sometimes this happens before a first investment. Other times it shows up between deals, even a...