Newsletters2026-01-21T12:40:56-05:00

Microsoft: Misunderstood AI Opportunity?

May 10, 2026 | In the end, our job is not to have the most differentiated portfolio, but one that we feel incorporates the highest-quality companies at attractive prices. In that spirit, we will look at Microsoft today. It’s trading well below its 10-year averages right now, and I want to find out whether that’s an opportunity or whether Microsoft is truly in deeper trouble than most investors think.

OTC Markets : A Picks and Shovels Play in Modern Capital Markets

May 3, 2026 | That company is OTC Markets Group, a business you’ve almost certainly come in contact with if you’ve traded over-the-counter securities (OTC) in the U.S. What impresses me most about the business is its coverage of over 12,000 securities, more than both major stock exchanges combined, yet the entire operation runs on fewer than 130 people!

CoStar: A Wide Moat Digitalizing Real Estate

April 26, 2026 | It's so boring that most investors have never heard of CoStar Group, and yet, it's a company that just reported its 59th consecutive quarter of double-digit revenue through financial crises, through COVID, and through the 2022 rate hike cycle that crushed commercial real estate transaction volumes.

Portfolio Review and Update: Changes for 2026

April 19, 2026 | Two companies will be leaving our portfolio today. Another one will be promoted to a core holding. We'll also revisit a good bunch of our other portfolio companies and a few watchlist names that a lot of you have been asking about — Trade Desk and FICO, in particular. We’ll also cover a couple of companies that Kyle, our new co-host(!), is getting up to speed on.

Programming Announcement

April 12, 2026 | Starting this month, The Intrinsic Value Podcast is officially merging into The Investors Podcast’s channel feed. If you’ve been with us from the beginning, you may remember that We Study Billionaires is one of the largest and longest-running investing podcasts in the world, with over 200 million podcast downloads, and we’re thrilled to be joining its main feed. So let me tell you what this means for you.

Mini Constellation Software: Analyzing Spinoffs and Acquisitions

April 5, 2026 | Constellation Software has been one of the most successful compounders of the last decade. But every business eventually struggles with the law of large numbers, and Constellation is no exception. Mark Leonard himself has acknowledged that, from all-time high prices, future returns would likely settle around 8%. Even after the recent drawdown improves that math, the reality is that a $40 billion company simply can’t deploy capital the way a billion-dollar company can.

Spotify: Investing in Music During The Age Of AI

March 29, 2026 | For the entirety of Spotify’s existence, the company has faced capped margins, yielding rather modest profit margins for a “tech giant”. Lately, though, the story has started to change. Operating margins have finally inflected upward in a real way. So, as always, let’s build a mental model of what Spotify is, why it exists, where value accrues, and what needs to be true for the stock to be attractive from here.

Kelly Partners Group: The Constellation Software of Accounting?

March 22, 2026 | Over the past few weeks, I’ve been hunting for businesses that could become the next 10, 20, or even 50-bagger. Companies at the very beginning of a compounding journey, with a proven playbook and enough runway ahead to multiply many times over.

Figma: Recovering From An 80% Post-IPO Decline

March 15, 2026 | Hype, or excessive exuberance, is one of the most reliable forces in markets, even if it wears a different costume every few years. Overhyped IPOs aren’t new, obviously, but what’s interesting is what happens after the party ends and the stock has to earn its keep.

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