Financial Literacy
Markets
+2
Nov 8, 2025
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11 min read
“Up and to the Right” + Advanced Tax Strategies
People love to say "stocks go up and to the right over the long run" like it's a law of physics. It's not. The U.S. stock market's 150-year run required exceptional circumstances—no foreign occupation, no revolution, stable institutions, and relentless value creation. Eleven other markets literally disappeared in the 20th century. For prices to rise, "steady" isn't enough. Businesses must generate more value, more revenue, greater efficiency, more cash—every decade. A lot has to go right. We shouldn't take any of it for granted. Plus: my conversation with Brent Sullivan on tax alpha strategies and why tax comes after risk, return, and diversification—not before.
Markets
+2
Sep 27, 2025
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6 min read
What Makes an Alternative Investment: My Conversation with Jane Buchan
An alternative investment diversifies beyond mainstream assets—simple enough. But some alts are mature (private equity), some are young adults (private credit), and some are adolescents (crypto). What people forget: volatility isn't the only risk. Jurisdiction and custody matter just as much. You could've bought Bitcoin at $1,000 and watched it hit $100,000—except if you stored it at Mt. Gox, which got hacked in 2014. That's a 100% loss, not a 9,900% gain. My conversation with Jane Buchan on what really matters when stepping into alt land.
Markets
+2
Sep 13, 2025
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7 min read
Fun Time is Over
For over a year, you could earn 5% on Treasury bills, pay your taxes, and still beat 3% inflation. You could move resources through time and grow wealth with little risk. T-Bill and Chill worked. Now? One-year Treasuries are at 3.7%. After taxes, you're at 2.3%. Inflation is 2.7%. Your wealth is a slow-melting iceberg. Fun time is over. But knee-jerk reactions can bite you just as hard as ignoring reality. Make sure your next move is strategic, not emotional. Plus: my conversation with Michael Imerman on the economics of FinTech.
Markets
+2
Feb 1, 2025
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4 min read
The Best of "Wealth, Empowered" Before It Had a Name
I moved my newsletter to Beehiiv and gave it a formal identity: WEALTH, EMPOWERED. My mission is to empower you when it comes to your wealth and understanding of markets. Before the platform change, I wrote every article on my website. Here are 2024's highlights: a framework for making decisions when the future is unknown (Seeing Around Corners), the three fundamentals of money management built over 20 years (An iOS), escaping the wealth management industrial complex (Is This What You Thought It Would Be), bare-minimum investment homework for beginners, being a liquidity provider when markets dry up (Be Like Water), and why governance might be the eighth wonder of the world.
Markets
+2
Jan 25, 2025
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9 min read
What Are We Going to Tell the Kids?
In 2008, I taught wealthy teenagers about risk management in a tent. They sobbed about their parents' struggles—the real estate crash, the fear, the angst. Joline Godfrey has spent decades helping families raise financially fit kids, and here's her insight: kids are ready to talk about money ten years before parents are. That's ten years of missed opportunities to talk about values, meaning, and how money is just part of the equation. Wealth makes some things easier and other things far more complex. Manage your affairs so you never have to say "What are we going to tell the kids?" Instead, aim for "the kids get it, we're good."
