Practicing Wisdom — Issue #19
Debt is optimism with a maturity date. This week, I explored what the AI boom’s increasingly elaborate financing structures reveal about the psychology of the moment—and where the first signs of missing cash flows are likely to appear.
Practicing Wisdom — Issue #18
AI doesn’t eliminate friction—it relocates it. As agents make tedious work cheap, old software moats weaken and scarcity shifts to compute, energy, capital, security, and trust.
Practicing Wisdom — Issue #17
What happens when every founder reads the same book? Jerry Neumann's Red Queen thesis, William Hockey's boredom moat, Benn Stancil on AI and empathy, and a brutal market reality check from Palm Valley Capital. Issue 17 explores why systematizing what works is the surest way to kill the edge — and what to do instead. Plus: the contrarian case for going slow in a world obsessed with scale.