$Hims & Hers Health Inc.(HIMS)$ ( ▼ 8.82% ) may be the most controversial stock in the Asymmetric Portfolio. Some investors think it’s a disruptive company with 10x+ potential. Others think it’s a parasite on society. Hims & Hers’ Catalysts There’s a story in any stock. A rise. A fall. And with Hims & Hers, the story is ongoing and volatile. I’ll be back with more on the story after earnings early next week, but I thought we should cover some of the latest with the company. The Value I’m going to start with the value, or what we pay as investors. Hims & Hers is in its high growth phase, so we shouldn’t be valuing the company based on earnings or free cash flow. The price-to-sales multiple is the most appropriate, and shares trade n

$Alphabet(GOOG)$ fell 12.3% last week and are down 26.8% over the past six months. Yes, I sold about a third of my Alphabet shares in July based on valuation concerns and the company entering a phase of negative free cash flow. But I didn’t see this reaction coming. I’ve been critical of a lot of the AI stocks out there because I think businesses like neoclouds are unsustainable and commodity suppliers like Micron will… commoditize. But Alphabet is king of the tech mountain and should be fine long-term. Still, the market punished shares because there are signs of disruption. Search isn’t growing the way it was expected to, and that puts the cash flow to fund AI into question. Here are my thoughts on the nuance and realities (both good and bad) at

$Anthropic(ANT)$ ’s S-1 Is Here! It’s all hands on deck. I had something else prepared for this morning, but when the biggest IPO filing we’ve ever seen hit, it’s time to call an audible. We got official numbers from Anthropic, the fastest-growing company at scale that I’ve ever seen, and a potential $2 trillion IPO within the next month. It’s impressive. It’s scary. And it’s holding up the market. I’ll get to the Anthropic S-1 and what I took from it in a moment. Anthropic’s S-1 If you’ve never seen an S-1, the financial filing a company makes before going public, this is an interesting one. Find the S-1 here. Anthropic is not only a well-known company, but it’s also arguably the most important in the AI buildout. The company has ~$500 billion in

$Anthropic(ANT)$ ’s S-1 appears to confirm roughly 45% Q/Q revenue growth in Q3. The filing also says that from Sep. 2025 to Sep. 2026, TTM revenue grew ~1,200%, while headcount rose ~170%. Revenue per employee jumped from $1.4M to over $6.6M. But the bigger concern may be the obligations section. $ANT has at least $390B in non-cancellable spending commitments over the next decade tied to $MSFT, $GOOG, and $AMZN. The $SPCX deal is also massive, though it reportedly includes exit options. That puts enormous pressure on revenue to keep scaling rapidly. Growth is impressive, but the commitments make execution critical. The market will be watching whether $ANT can grow into those obligations. $Microsoft(MSFT)$

The stock market threw something of a fit on Thursday, and a lot of investors were confused. No big company failed. Demand for AI still looks like it’s off the charts. Why would the AI trade be down so badly if the numbers keep going up? I’ve been laying out my thesis for months (here, here, here, and here, for example) and explained why I’m not getting in front of what may be a steamroller. And that’s worked well of late. The Asymmetric Portfolio is up 1.7% this week thru Thursday, while the $Invesco QQQ(QQQ)$ ( ▼ 0.01% ) is down 0.75% and the $SPDR S&P 500 ETF Trust(SPY)$ ( ▼ 0.52% ) is only up 0.1%. Yes, my positioning with a non-AI portfolio has paid off this week. But let’s be honest, it hasn’t pai

When I was growing up in the 1980s, we had a set of Britannica encyclopedias on the bookshelf in the living room. If I had a question about an animal, country, disease, or anything else, that’s where I could go to try to find an answer. Despite being thousands of pages, the explanations weren’t in-depth, weren’t updated, and often what I was looking for wasn’t there. The next step was going to the public library a few blocks away. And I never quite got the hang of searching their catalog system. If you weren’t alive then, it’s hard to explain just how hard it was to find information. Sometime in the late 1980s, we got a computer with MS-DOS. In the early 1990s, that computer could access the internet through a service called Prodigy. Suddenly, you could get the weather 24/7, not just at 5:

Only about $0.05 of every dollar spent on $Uber(UBER)$ ends up as profit or free cash flow for the company. Now imagine an ad-supported version of Uber. What if advertising revenue could subsidize fares, making rides significantly cheaper — or even free in some cases? 👀 Uber already has a massive consumer network and valuable insights into shopping and travel behavior. Advertising could create a higher-margin revenue stream without requiring a proportional increase in rides. The big question is how much of that potential can translate into sustainable free cash flow. A trillion-dollar valuation by 2035 is an ambitious target, but new monetization opportunities could change the math. 🚗 Meanwhile, $General Motor

The last few days have felt different on the stock market. Questions are being asked about former rocket ships (including Rocket Lab), Anthropic’s revenue growth is slowing, neocloud yields are rising, companies are cutting back on AI spending, inflation is stubbornly high, and it’s possible the semiconductor and AI stocks that have held up the entire market in 2026 could come crashing down. At least, that’s the narrative. A few days doesn’t make a trend, but if you’ve felt uneasy the last few days, it’s time to remind ourselves how to survive — and thrive — in a bear market. $SPDR S&P 500 ETF Trust(SPY)$ $Invesco QQQ(QQQ)$ Do Your Research Ahead of Time! It’s almost impossible to think clearly in a fal

Questions are finally starting to be asked about the AI trade, and the answers may not please some. Longtime readers know the AI trade is something I’ve generally stayed away from. We’re seeing trillions of dollars invested in AI technology that hasn’t proven (yet) to have a sustainable business model. My argument isn’t that it’s not valuable, but rather that we’re likely to over-invest, get a correction (the bubble pops), and then the opportunity for long-term gains comes in the wreckage. In other words, the “Trough of Disillusionment” is my sweet spot, which I explained in this 2024 article. I’m not predicting the bubble bursting yet. But I’m not going to get in front of that train, holding the bag when it does. And the past week has seen most of the AI infrastructure (bottleneck) stocks

A picture is worth 1,000 words. So, today, I’m replacing a lot of words with pictures. Over time, owning growth stocks that can compound year after year gives us a great chance to beat the market. So, what are the fastest-growing stocks in the Asymmetric Portfolio? #1: $SoFi Technologies Inc.(SOFI)$ ( ▲ 1.22% ) #2: $Robinhood(HOOD)$ ( ▲ 1.88% ) #3 $Zeta Global Holdings Corp.(ZETA)$ ( ▲ 0.18% ) #4 $Duolingo, Inc.(DUOL)$ ( ▼ 0.86% ) #5 $Hims & Hers Health Inc.(HIMS)$ ( ▲ 10.19% ) Over time, growth will drive stock performance, but over the past year, that hasn’t been the case

Last week, I wrote Disaggregating the Aggregator, explaining how I was viewing the possible AI agent-led disaggregation of companies that currently aggregate demand in the smartphone era. These are companies like $Uber(UBER)$ ( ▲ 0.34% ), $Alphabet(GOOG)$ ( ▲ 1.62% ), $Netflix(NFLX)$ ( ▼ 1.16% ), $DoorDash, Inc.(DASH)$ ( ▲ 3.83% ), etc. My shorthand is that it’s the apps that we choose to interact with every day. But in that article, I came away relatively bullish on companies that had some kind of tie to the physical world. Uber with drivers, $Zillow(Z)$ with homes, etc. As I’ve t