Searching for Moats

Approaching 40. It was a few years ago that I started to realize: 1. the only thing that actually matters is raising my kids And 2. the only interests and hobbies I have now is drinking coffee, listening to podcasts, watching the stock market and shitposting on this app

Sometimes my son gets scared at night. I lay down on his floor using a stuffed animals as a pillow, and he puts his hand out so I can hold it in mine. Every time now I know it might be the last time I get to do this so I hold on just a little bit tighter, not wanting to let go

I am horrified and angered by the swastikas painted on homes and synagogues in Queens, including on a plaque honoring survivors of Kristallnacht. This is not just vandalism — it is a deliberate act of antisemitic hatred meant to instill fear.

There is no place for antisemitism in Queens or anywhere in our city. I stand in solidarity with our Jewish neighbors. Their safety, dignity, and belonging are non-negotiable.

The NYPD Hate Crimes Task Force is investigating and I am confident those responsible will be held accountable.

Buying cheap tech stocks in 2026 is the closest thing in modern public markets to being handed a list of 1999 internet companies after the bubble burst, in 2002, when the entire category had been left for dead, the analysts had stopped covering them, the funds had been forced to liquidate, and the price action had been so bad for so long that the very word "tech" had become, briefly, a kind of insult at dinner parties. The investors who bought that list, in 2002, in equal weights, and held for ten years, made some of the largest legal fortunes in modern American finance. They did not pick winners. They bought a basket. They held Amazon at $7 and they held companies that went to zero, and the math, on the basket, worked, because a few of the names compounded so violently that they paid for everything else many times over, and the entire portfolio, in aggregate, returned multiples of the original capital while everyone else in the country was buying real estate at the top of the housing bubble. The 2026 version of this trade is sitting in plain sight. There are, right now, roughly 90 publicly traded technology companies in the United States that are profitable, growing, generating free cash flow, sitting on net cash, with strong gross margins, durable customer bases, and stock prices that are 70% to 85% below their 2021 highs. The market has decided, as a class, that these businesses are obsolete, that AI is going to kill them, that the category is over. The cash flow statements say something different. The renewal rates say something different. The customer concentration data says something different. The math, when you actually do it, says these companies are compounding right now, today, while the stocks are flat or falling, and the gap between price and value is wider than it has been at any point since 2002. You do not need to be smart. You do not need to pick the next Amazon. You need to build a basket of 20 to 30 of these names, in equal weights, hold for at least five years, and let the math do what the math has always done. Some will go to zero. Some will compound. The aggregate, by any historical standard, will work. It worked in 2002. It worked in 2009. It worked in 2016. It worked in 2022. It will work this time, because the structure of the opportunity, which is forced selling by people who used to love these stocks and now hate them, is the most reliably profitable setup in equity markets, and it is, in 2026, sitting on the shelf, marked down, available to anyone with a brokerage account and the willingness to be ridiculed at dinner parties for the next 18 months in exchange for being right for the next ten years.

Might be a function of getting older/when I graduated but you could get really feel analysts rapidly getting worse around the ‘21-‘22 classes. First because of covid, and then AI is a whole different animal in itself.

In 2015, you could generate a 3x MoM return by doing nothing. You just showed up for board dinners and sold 5 years later on a higher exit multiple. Every deal worked regardless of the business quality.

Political violence is absolutely unacceptable. I am glad the President and guests at the White House Correspondents’ Dinner are safe.

Yeah. It’s not investing.

Naval being a grifter was not on my 2026 bingo card

It's BEYOND moral failure. It's perversion + inversion of reality. It's 100% like protesting a rape survivor speaking her truth on campus because it would be insensitive to the suffering of her rapist in prison. Encourage your loved ones to be part of "reality-based community"

"The CIO of a pension fund explained that in his 14 years on the job, his fund had never been above the 27th percentile or below the 47th percentile. It was solidly in the 2nd quartile of pension funds. As a result, for 14 years, he was in the 4th percentile." -Howard Marks, Oaktree Capital

Private equity firms: We love to invest in periods of market dislocation, sectors with uncertainty, and buy complexity and sell simplicity Also private equity firms: We are pencils down on software and more broadly tech in general.

From what I've heard, software is pretty much pencils down at a lot of shops, but curious what others are hearing.

For a while I've insisted that ChatGPT is my main AI companion because I've been using it consistently for 2 years and it knows me better than the others. I thought memory was a real switching cost. That was until I realized today that I could simply just ask it to generate a report on everything it has learned about me (w/a prompt created using Claude) so I could share it with the other LLMs for their context. Will report back in a week on how useful this exercise has been on lowering the switching costs.

The weird thing right now is the public markets don't have access to the growth side of software. Right now the trade is to sell SaaS and buy semis (the raw material of AI). What you don’t have yet in the public markets are the AI native software companies and therefore, you’re comparing the practical values of owning say a Salesforce vs the mythical value of owning a company that’s growing 10x (without having seen the actual financials). And everyone is always going to want the myth. These SaaS stocks aren’t going to trade in a sane fashion until the next generation of AI companies go public and investors can decide how to price a 10% revenue growth company with 30% cash flow vs 300% revenue growth company with negative 100% cash flow and SBC that will blow your mind. Until then, you’re walking hand in hand with your significant other looking over your shoulder. You know the meme.

Apollo’s Marc Rowan on Redemptions and Software: “If you can’t as a 1L credit manager meet 5% redemptions per quarter, I’ll say it frankly, you’re an idiot.” “If you discovered 8 weeks ago that enterprise software was vulnerable to AI, you kind of weren’t doing your job.”