2025 Investment Portfolio Review & 2026 Playbook

One way to look at investing it that it allows you to express your opinion. That opinion should, of course, be informed by underlining analysis and underwriting. In the most simple framing, the only to make money in a market is to know something the average market participant is ignorant to.

4-Hour Work Day

I’m sitting at a Chase Sapphire Lounge at an international airport. All around me are “business people”. How do I know? For starters, they are starring into their Lenovo Thinkbooks. They smile awkwardly every once and awhile to signal their engagement with whomever is on the other side. The outliers in this room? The lucky ones starring into a MacBook instead of a Thinkbook. Literally not a single person in my view is not grinding away. Like most people, these folks are completely tethered to the albatross that is their VPN.

The Emperor Wears No Clothes

I feel about as negative on our longterm prospects as I’ve been in years.

Beyond the foundation of the U.S. system as a democratic republic, one could argue the U.S. banking system, Wall Street, and the U.S. technology ecosystem, Silicon Valley, are the two most valuable assets we have.

Personal Burn Rate

Benjamin Franklin, who was a prolific writer among other things, was fond of making lists. On more than one of Ben’s lists the notion of “frugality” can be found. I share the love of writing, making lists, and have a deep respect for frugality myself.

Lifestyle Creep

When I landed my first job, I rewarded myself with a Louis Vuitton scarf.

Once you are done laughing or rolling your eyes; let’s explore why I bought this expensive scarf.