Milton Maxwell, September 2025 Update

Robinhood hit record highs after joining the S&P 500, expanded into the UK, and advanced its crypto and tokenization plans. It launched new social and AI features, but faces rising valuation concerns and regulatory scrutiny.

Hims & Hers received FDA warning letters over compounded semaglutide claims, creating regulatory risk around its GLP-1 business. Shortly after, it launched a new testosterone therapy line via a partnership with Marius Pharmaceuticals. The stock dipped on the FDA news but rebounded as investors viewed TRT as a new growth driver ahead of Q3 results.

We'll leave IREN and EOSE as an exercise for the reader, we have ChatGPT these days.

A quick note on what we'll share going forward: investing is one part finding good companies, one part finding fair prices, and one part portfolio construction. We share a few good companies publicly but keep valuation and allocation research in-house.

And just a reminder: this is not financial advice to buy or sell any of these companies.

§02On long/short thesis

Every major technological shift follows an adoption cycle, from early discovery to mass adoption, and with each wave both new and old industries are reshaped. The impact isn't just tech companies beating other tech companies, it's technology reordering entire economies.

In the personal computing era, Microsoft and Apple didn't just outcompete other hardware makers, they changed how businesses operated, making spreadsheets, word processing, and digital workflows essential to every company. Firms that failed to modernize, from typewriter makers to office suppliers, quietly disappeared.

The internet did the same on a larger scale. Amazon and eBay transformed retail and logistics, while Google and Facebook redefined advertising, displacing entire industries that had dominated for decades. Newspapers, department stores, and travel agents weren't beaten by competitors within their fields, but by platforms that rewrote the rules of distribution and discovery. In the mobile era, Apple and Google not only won against other device makers, they absorbed value that once went to carriers, camera companies, and even the music industry. Each step in the cycle shifted power from the physical world to digital intermediaries that could scale infinitely and personalize instantly.

Now, artificial intelligence is creating another wave of cross-sector disruption. Nvidia and OpenAI are at the core of a transformation that is not limited to software; AI is starting to change healthcare, finance, education, and manufacturing, fields once thought resilient to technological substitution. The winners in this new cycle won't simply be "tech companies," but any organization that uses technology as leverage: automating, predicting, or personalizing better than peers.

This dynamic is why long–short investing works. Every adoption cycle creates asymmetric opportunities: the new winners benefit from compounding innovation, while old incumbents face structural decline. By going long the disruptors and short the disrupted, investors can express both sides of the technological transition. The long side captures the compounding effect of innovation, companies that harness change to expand margins and markets, while the short side benefits from creative destruction, as outdated business models erode over time.

The beauty of a long–short approach is that it isolates alpha from broad market direction. You're not betting on the market rising; you're betting on the future replacing the past. This is our primary thesis. These cycles unfold over years, providing sustained opportunities to identify who adapts and who gets left behind.

When you look at the returns of the Mag 7 or the Nasdaq 100 compared to the broader index, you can see that amongst the Mag 7 picking winners is pretty easy, but picking losers from the Other 493 looks pretty easy too.

Just be incredibly careful when shorting. It is easy to get squeezed. Look at OPEN and GME for some nightmare fuel.

§03Notes from Singapore

We spent time in September and October in Singapore meeting with fellow entrepreneurs, investors, and business leaders, deepening our view on the global economy. Singapore remains a fascinating case study of an open, trade-driven economy balancing East and West while serving as a hub for Asia's manufacturing and capital flows. Over the past decade, the government has deliberately catalyzed entrepreneurship via programs such as Startup SG and SGInnovate. Funds such as Iterative (where Charlie is an LP) were early in recognizing this wave of innovation in Singapore.

Money from Asia streams into Singapore. Crypto interest is rising, both as exposure and as currency of payment, the latter of which feels natural for a city built for cross-border movement. At the same time, the industrial logic is undeniable: Chinese EVs like BYD have recently amassed 20% of new vehicle registrations, and XPENG is building its charging footprint there, tangible signs that tech, capital, and supply chains are reconverging in real time. We're looking at these firms because we believe tomorrow's robotics wave will depend heavily on vertically integrated, cost-efficient EV manufacturers where Asia has a significant edge.

§04Thanks

A shout-out to Sam Scott, Dan Kang, and Sophia Deng for feedback on our first newsletter. We've made edits with your thoughts in mind.

Thank you for being a part of this journey. If you have any feedback, please reach out at hello@miltonmaxwell.com.

Alex & Charlie