Posts

If you’ve been watching MSTY in your brokerage app lately, you might have felt the same whiplash I did. Bitcoin sells off hard. MicroStrategy (MSTR) follows. MSTY suddenly drops 8–12% in a single day. You open the holdings page for comfort and see… a pile of short-term U.S. Treasuries. Wait. How can something that looks like a T-bill fund on the surface trade like a leveraged Bitcoin sidecar underneath? Shouldn’t those Treasuries give it some kind of floor? And if the market price is down double digits, why is the discount to NAV only 0.03% or whatever your broker shows? ...

If you hang out in FIRE spaces long enough, you see the same script: “Max your tax-deferred accounts, buy broad index funds, follow the 4% rule, coast into retirement.” It’s a good script. But there’s a silent assumption baked into it: That growth in tax-deferred accounts is obviously superior, and That anything involving taxable income and dividends is a sucker’s game. I don’t think that’s always true. This isn’t a “4% rule is dead” post. This is: “If you want $4,000/month forever, is there a way to get there faster than a taxed 4% rule?” ...

The Skylight Bug Early in my career we built digital signs for retail stores—solid hardware, clean code, perfect test results. Then one location started failing every afternoon at three o’clock. Same code. Same network. Same everything. We tore through logs for days. Nothing. Finally, someone flew out and saw it in person. A skylight was focusing a beam of sunlight directly onto the unit each afternoon. The system wasn’t crashing—it was cooking. ...

Oppenfolio isn’t a brokerage. It’s a mirror. The site pulls the same raw account data that E*TRADE does, symbols, share counts, dividend histories, but displays it through a lens I actually trust. A custom set of scripts, charts, and rolling-yield math that turn noise into something readable. Where the broker’s dashboard chases excitement, Oppenfolio measures reality. That contrast became obvious this week. Just this week, my E*TRADE account told me I’d earn $23,000 in dividends this year. Today it says $19,000. I didn’t sell anything. I didn’t buy anything. Nothing changed. ...

Do you think you can time the market? The honest answer separates two kinds of investors. Bob buys steadily, week after week, no matter what the market’s doing. He doesn’t overthink entry points. He just follows the plan, trusting that time and compounding will smooth the rough edges. Alice, on the other hand, waits for the perfect moment. She studies the charts, watches for red days, and only buys when the market dips. Her logic is sound: why pay full price when you can wait for a sale? ...

How a $25 experiment became a self-funding creative machine Three years ago, I wanted to fund a side project, something creative, experimental, and probably unprofitable at first. Maybe a YouTube channel. Maybe a self-published book. The kind of thing that needs a few hundred dollars a month to breathe but doesn’t justify touching family savings to do it. So I started smaller. Much smaller. The Seed Loop The seed money wasn’t a windfall. It wasn’t inheritance or savings. It was Apple Cash. Grocery cashback. Twenty or thirty dollars a month, the kind of digital lint everyone ignores. ...

Six months in, and the Oppenfolio chart tells a story most stock pickers can’t. Green everywhere. Even the one ugly red mark has paid back its losses in dividends. That’s the difference between buying a stock and building a machine. Stocks rely on luck. Oppenfolio relies on math. But running the machine taught us something new. The results showed us that raw yield isn’t enough. To make this durable, we needed new rules. That’s where the $30,000 Cap and the 2x Rule came from. They aren’t how we started. They’re what we learned. ...

When Oppenfolio launched, the buying plan was simple. A fixed mix of symbols, each with a set target weight. Every so often I would make a manual adjustment, but the structure was static. New contributions followed the plan without any memory of what had worked best or what had lagged behind. That approach was easy to manage but left efficiency on the table. So we’ve pivoted. Now every purchase shifts the mix slightly, based on how each symbol has contributed to new money over its lifetime. If a symbol has delivered more than expected, it earns a little more weight the next time. If it has underperformed, it gives some back. Over time the system adapts, growing leaner and more efficient without requiring constant manual intervention. ...

There’s a famous quote from Dwight D. Eisenhower: “Every gun that is made, every warship launched, every rocket fired signifies, in the final sense, a theft from those who hunger and are not fed.” True. But here’s the part no one says out loud: Every meal given to a hungry child is a bullet that wasn’t manufactured. The two truths are bound together. Every act of care diverts resources away from harm. Every act of harm diverts resources away from care. There is no clean separation. ...

Six months ago I launched OppenFolio with a simple goal: Take $50K of capital, scale it up in $10K tranches, and build a machine that spits out $1K a month in after-tax income. Today? That’s exactly what it’s doing. Which feels… strange. The Numbers Portfolio scaled to $50,000, right on plan Current cash flow: ~$1,000/month after tax Paper NAV: –2% unrealized Dividends earned: +4% Net effect: +2% new money overall That’s the machine, working as designed. No drama. No fireworks. Just steady output. ...