You Can Never Win, You Can Never Be Right

And I'm making peace with that.

For a long time, I confused being right with making money. I thought the two were naturally connected. If your analysis was sound, if your thesis was correct, if you saw something before everyone else did, then eventually the market would reward you for it. Sometimes that happened for me. Many times it didn’t.

Over the years, I have been wrong innumerable times. But I’ve also been right about a lot of stocks, macro trends, bubbles, narratives, and distortions in the market. I have identified companies that were wildly over- and under-valued. I have spotted trends early. I have watched ideas play out almost exactly as I expected them to and have watched others defy all sense of what I perceive to be reality.

And yet despite everything I’ve gotten right over the years, looking back I see that active trading did more damage to my portfolio (and mental health) than almost anything else I have done in investing. That is not an easy thing to admit after years of writing about markets, but it is the truth. I’ve made peace with the fact that I have far more value as a commentator than I do as a trader.

One of the hardest lessons markets have taught me is that objective truth and market outcomes are two completely different things. You can be fundamentally correct and still lose money. You can have the right thesis and the wrong timing. You can understand valuation perfectly and still get steamrolled by liquidity, momentum, central bank intervention, sentiment, or some exogenous event nobody could have predicted. The market does not give a fuck about your idea of fairness, justice, facts or timing. It does not care about logic. And it certainly does not care about your ego.

So many times I have had the right idea and the wrong execution. At some point that simply becomes exhausting. All I can do now is try and offer up ideas to people who are hopefully better at executing them than I am.

I love the old investing saying, “be right and sit tight.”

When I look back honestly at the periods where I performed the best, they were usually where I did the least. I bought quality assets (or shorted dogshit where cost to borrow was low), stayed patient, ignored noise, and let time do the heavy lifting. The periods where I performed the worst were usually the periods where I tried to outsmart everything around me. The more I traded, the worse I did. Not because I suddenly became less informed or less intelligent, but because constant action creates constant opportunities to make mistakes.

Active trading — like live betting a baseball game on DraftKings — gives you the illusion of control. It tricks you into believing every moment requires a decision and every move deserves a reaction. Most of the time it does not. Most of the time the smartest thing you can do is nothing at all. For me, that rule applies all of the time.

As I look at society, the part that scares me nowadays is how normalized gambling and speculation have become in everyday life. It is no longer just Wall Street or casinos. Prediction markets, sports betting, options trading, crypto leverage, gambling apps — life has been turned into a tradable hamster-wheel-like dopamine loop. And you can access action 24 hours a day, 7 days a week.

Every event is now a market. Every opinion is now a wager. Every moment of boredom can be monetized by putting money at risk on your phone. I dabbled on Kalshi for a little while and had to delete the app. It’s outright frightening how seductive and accessible it is. I also had offers from several prediction market companies for sponsorships and almost took one up on the idea. But ultimately, I decided that I couldn’t, in good conscience, do it. Some days I feel like the only person in the financial blog-o-sphere not sponsored by either Kalshi or Polymarket.

I genuinely have no idea what this is going to do to younger generations that have grown up inside this environment. 24 hour prediction, crypto and sports markets are only now just developing and I’ve sidestepped them somewhat thanks to my age, other interests, being in therapy long enough to understand the negative effects and the fact that I’m outright sick and tired of the chase. But the gravity and the ease of use for many of these apps and markets for neophytes and younger traders scares me.

I do not think we fully appreciate how psychologically corrosive it is to live in a world where you can gamble on literally anything, all day, every day, from the same device you use to socialize, work, and exist. The line between investing, entertainment, speculation, and addiction has become almost impossible to distinguish. It is an incredibly insidious trap because it disguises itself as empowerment. People think they are participating, hustling, staying informed, building an edge. But for many, it slowly turns into a permanent state of emotional and financial agitation where your brain is never actually allowed to rest.

In some ways it feels like we have turned ourselves into zombies. Everyone is refreshing prices, odds, feeds, notifications, reactions, constantly searching for the next hit of stimulation or the next opportunity to win back money, status, or attention. I’ve been immersed in it myself…it’s all-consuming. I see guys I spar with trading crypto in between rounds. Friends I go to mid-week dinners with are watching the futures on their phone while eating and trying to hold a conversation at the same time. I see kids in their 20s betting on every pitch of a baseball game from their phone at the bars. And I’ve been all three of those guys…at once.

The modern economy increasingly feels engineered around addiction, distraction, and impulsivity. Stillness now feels unnatural to people. Silence feels uncomfortable. Patience feels obsolete. That is part of why I have become so focused on stepping away from trading and being on my phone altogether. At a certain point you realize protecting your peace and relationships are more valuable than chasing dopamine every other second.

For me, I’m thankful that it’s been obvious to step away. I quit fantasy sports a couple of years ago and never regretted it. For years I couldn’t even enjoy games because I was so tied up in so many leagues. A little while after that I cut myself off from sports betting apps for the same reason. I put measures in place this last week so I literally don’t have to trade at all anymore. I have a few regular contributions to a couple accounts managed by advisors who I know are experts and see the world like I do — mostly in sector ETFs, bonds, and conservative long term investments. I know that I don’t need to constantly swing at every pitch or treat investing like a daily competition against the world. It’s not. And even if it was, I wouldn’t care about winning — I’m happy with the work I do, writing about ideas, and the relationships in my life are more important than “being right” about anything.

The same lesson applies to writing and commentary. After years of being a columnist, blogger, and market commentator, I have learned another uncomfortable truth. You are never going to be right with your opinion to everyone. It does not matter how nuanced your argument is. It does not matter how carefully you explain yourself. It does not matter how much evidence you provide or how many caveats you include. People hear what they want to hear and increasingly they interpret analysis through the lens of tribalism, emotion, politics, and identity instead of substance.

A recent example: I wrote about SpaceX’s implied valuation approaching two trillion dollars and the first response I saw was, “Not a fan of Elon, are you?” That comment perfectly captures modern discourse. Whether I like Elon Musk personally has absolutely nothing to do with whether a company trading at absurd multiples makes sense fundamentally. As I noted in the comments, the company could be run by Jesus Christ himself and I still would not understand paying something like an 100x EV/revenue at what increasingly feels like the tail end of a historic liquidity bubble.

But people increasingly interpret analysis as allegiance. If you criticize a valuation, people assume you hate the founder. If you say something positive about a company, people assume you are talking your book or cheerleading for management. Nuance has disappeared. Everything now gets flattened into loyalty tests and emotional reactions. And I’m guilty of this myself. It’s exactly how I used to think when I started trading in markets in my 20s, so I understand it.

As a columnist, after a while, you get tired of fighting that battle. The celebrations for getting things right are always short lived and frankly, don’t mean much to me. I pride myself on being right and all I need is my personal satisfaction from it. The backlash for getting things wrong lasts much longer, is far more public and cuts way deeper than getting anything right could. I have been doing this long enough that I have learned to mostly tune it out, but I would be lying if I said it has no impact. Words affect people even when they pretend they do not. Public criticism accumulates over time whether you acknowledge it or not.

There is also something uniquely frustrating about finance because markets themselves are often irrational for far longer than anyone expects them to be. You can identify a bubble early and still get destroyed waiting for reality to matter. You can point out fraud, leverage, terrible management, or insane valuations and watch stocks continue climbing anyway because liquidity and momentum overwhelm fundamentals.

Short selling taught me that lesson better than anything else ever could. I did intensive research on the short side of markets for about a decade. I’m not in the industry anymore and I never will be again. So many times I felt I had objective truth on my side. I saw accounting issues, broken business models, unsustainable debt, promotional behavior, and obvious red flags.

Yet loopholes, bailouts, lobbying, financial engineering, lax regulation, media narratives, speculative excess, and sometimes outright corruption allowed terrible companies to survive far longer than logic suggested they should. Some flourished. Outright fraudsters were celebrated as business tycoons.

The lesson? Markets are not moral systems. Bad actors are not always punished. Fraudulent people are not always exposed. Poorly run companies are not always judged fairly or promptly by the market. I spent years believing they eventually would be. Now I am not so sure.

That realization is honestly a little sad, but maybe there is also freedom in accepting it.

At 43 years old, I think what I am really trying to do now is make peace with being misunderstood. In markets, in politics, and in life, people will project onto you no matter what you say. They will hear what they want to hear. You can explain yourself perfectly and still be interpreted incorrectly. You can be completely sincere and still have your motives questioned. That is just part of being public now and maybe it always was.

I am not interested in trying to win every argument or catch every move in the market. I am no longer interested in forcing outcomes that are ultimately outside my control. I still love writing. I still love thinking. I still love identifying ideas and trends and asking questions. In many ways I think I am a much better writer and idea identifier than I am a trader, and honestly I enjoy writing far more anyway. Readers can do with my thoughts whatever they want. Some people will agree. Some people will not. Some people will misunderstand me entirely. That is fine.

The older I get, the less interested I become in noise and the more interested I become in peace.

Looking for peace at a spa in Iceland earlier this year

I want to focus on things that actually matter. My relationships. My health. Exercise. Eating well. Making music. Prayer. Presence. Discipline. Building a quieter and more meaningful life away from the constant emotional churn of markets and online discourse. As a daily columnist (on the incredible Substack), I realize the irony in that statement.

Iceland, Feb 2026

None of this is meant to sound sad. If anything, it is probably the healthiest and most realistic perspective I have had in years. I am not giving up. Just realizing there will always be another argument, another bubble, another headline, another critic, another person convinced you are either a genius or an idiot depending on what happened over the last forty eight hours. That cycle never ends.

By the way, have you seen the Northern Lights?

Iceland, Feb 2026

OK, I digress. Look, maybe some of my elder-statemen/women subscribers can weigh in with their thoughts, but I think all you can do is try and stay intellectually honest, remain humble enough to admit when you are wrong, protect your peace, and continue doing work you find meaningful.

I will keep writing. I will keep sharing ideas. I will keep trying to think independently and ask honest questions about markets and the world around me. What readers choose to do with those ideas is ultimately up to them.

But I no longer feel the same need to prove myself right all the time because eventually you realize something important: you can never win, and you can never be right to everyone anyway. I’m just immensely appreciative that my readers find enough value in my thoughts to stick around, keep me motivated to continue sharing my thoughts, and are generous enough to contribute to a vibrant, ongoing discussion on the site.

God bless, and enjoy the long weekend.

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This is not a recommendation to buy or sell any stocks or securities, just my opinions. I often lose money on positions I trade/invest in. I may add any name mentioned in this article and sell any name mentioned in this piece at any time, without further warning. None of this is a solicitation to buy or sell securities. I may or may not own names I write about and are watching. Sometimes I’m bullish without owning things, sometimes I’m bearish and do own things. Just assume my positions could be exactly the opposite of what you think they are just in case. If I’m long I could quickly be short and vice versa. I won’t update my positions. All positions can change immediately as soon as I publish this, with or without notice and at any point I can be long, short or neutral on any position. You are on your own. Do not make decisions based on my blog. I exist on the fringe. If you see numbers and calculations of any sort, assume they are wrong and double check them. I failed Algebra in 8th grade and topped off my high school math accolades by getting a D- in remedial Calculus my senior year, before becoming an English major in college so I could bullshit my way through things easier.

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