Filippo

Ryan was once a friend. He’s been out sailing on my boat. I helped him sketch the initial pivot to writing about the Stoics. Sadly, this isn’t his most shocking video. That distinction belongs to the ones featuring his kids at Trump rallies. He’s a smart guy and a deep thinker, but Trump has him tied up in knots. What made him popular is the unique, insightful advice he gives. That earned him a roster of “celebrity” friends, mostly authors, who reciprocated with network connections and advice of their own. His closest friend is @RobertGreene, who is genuinely a great person. Ryan worked as his assistant, and Robert introduced us. Both are voracious readers. Problem one: Robert is a dork (the best kind), while Ryan is the kind of guy everyone in high school liked. Put another way: Ryan is socially motivated. Robert is introspective and observant. Problem two: Robert had brutal experiences in the workforce and wrote The 48 Laws of Power, in essence, to understand why he kept getting screwed by alpha males. He wants to help people understand the world around them. He isn’t tilting at windmills. He’s offering insight grounded in historical context. Ryan wants to actually improve the world itself. I genuinely believe his motives are good, but unlike the actual Stoics, he lived a normal life that turned into a very charmed one. Ryan’s social radar is phenomenal. He reads trends and knows how to ride them in a modern context. But I don’t think this is an act. He genuinely seems to believe Trump is a monster. How did he arrive at that false conclusion? I don’t know for sure, but we share many mutual friends, and I can trace where our thinking began to diverge. What made me reject the popular “Trump is bad” narrative in our old friend group is the Bronx. My childhood there always lingers in the background. I was (briefly) an EMT in the Bronx. My mother was a visiting nurse in the projects. My father was a firefighter when the Bronx was burning. I’ve thought hard about the liberal policies, and a few conservative ones, that produced the war zone surrounding me. I’ve spent decades working alongside people with hard jobs: soldiers, first responders, offshore oil drillers, merchant mariners. I understand why Trump’s base loves him. I understand why they agree with his policies. Even that wasn’t enough. After January 6th, I had to reevaluate my feelings toward Trump. I hated the Democrats’ slide toward Marxism. But could I keep supporting Trump after so many first-term failures? So I read roughly a dozen biographies, not just about Trump, but by his friends and associates. People who loved him. People who hated him. A truer sense of the man began to emerge. Not all “good,” but realistic, intelligent, and possessed of a deep love for Americans of every type. What makes Ryan so smart is the sheer historical context he carries from a lifetime of reading. He can plug real, useful historical lessons into almost any problem. But you absolutely must understand the full context of a problem in order to fix it. And like the actual Stoics, you have to index the good you want to do against the first-hand disasters you have actually seen. Ryan genuinely wants to fix America, but he is unbalanced. His historical context runs deep. His modern context is superficial. Here he’s trying to solve a problem he has incorrectly indexed as “Trump is bad,” without firsthand exposure to the sufferings of real Americans who have lived through real danger and tragedy. He’s plugging that deep historical context into a superficial understanding of the problems Trump is actually trying to solve. The result? Frustration, anger and rhetorical bombardment that’s almost the polar opposite of stoicism.

All but one horse in the 2026 Kentucky Derby are related to Secretariat, the greatest racing horse of all-time 🤯 (h/t @sportingnews)