ZD 25.44: Smart Money Reading List

Finding good investment advice is hard. Here are some good ideas.

Enjoy a round-up of the best free investment reading materials on the net. In the Distilled Spirit learn about tweenfluencers, figure out how to play in the lotteryification of everything, find out how to use AI browsers and get guidance on NotebookLM.

Better Inputs, Better Investments

I’ve read hundreds of finance newsletters over the years. Most are noise — promises, posturing, recycled headlines. But every so often, one actually teaches you something worth trading on.

Financial newsletters have been around forever, and most aren’t worth the headspace. The field is crowded with hustlers and hype artists—but every now and then you find a signal cutting through the noise. Like anything around making money, the signal-to-noise ratio is horrible. Many publications push some form of a Ponzi scheme. Caveat emptor is good advice. As a veteran investor, it takes a lot for me to believe a source enough to share it.

There are useful perspectives in the space. You need to read widely to be effective at understanding any subject. Divergent viewpoints are very important to ground your thinking. That fact counts double in investing and portfolio management. Here are my investing guiding lights, the newsletters that really help me shape my portfolio.

Financial newsletters can be pricey — after all, they have a pretty good argument about making you money. Almost everything here has a paid version. But this list has been specifically curated so that each item has a lot on the free tier. Most publish a web-facing archive you can explore. One thing I believe in is writers who believe their Writers who let ideas see daylight — not hide behind paywalls — are a good sign.

Frontrunning The Market

The single most important thing in investing is understanding where the inflection points are in markets. If you get the directionality right, it is hard to lose money. Reading what the rainmakers read helps. They curate the week, surface the major threads, and help you sharpen your market thesis.

• Byrne Hobart writes about big, market moving trends and helps you spot inflection points in The Diff and Capital Gains.

• Eric Soda writes about the market and how it is developing in Spilled Coffee. It is highly visual but often quite focused in a good way.

• Sam Ro, CFA pulls together macro and the market weekly in the TKer.

Betting Against the House

Sometimes you make money by swimming against the current. Contrarian bets and smart hedges can turn market fear into working capital when others pull back. Here are a few of my favorite sources for the times you need a bit more alpha or when you want to bet against the house.

• Finding great stocks is the name of the game. Kevin helps you spot them on his 100 Bagger Hunting.

• Kris Abdelmessih Moontower is a must read to understand options trading. Stick around for interesting exploration of risks and market making war stories.

• Dividends stack cash. Dividendology shows you how to maximize them.

• What if you could use tax-aware investing to increase your returns? Brent Sullivan tells you how in Tax Alpha Insider.

Diving Deep and Discovering Gems

Go deep where others skim. These sources map entire sectors, dissect balance sheets, and trace business models to their breaking points. These are great sources for longer explorations of a specific company or sector. They combine really well with bigger picture direction intelligence to help narrow down what to trade and at what valuation.

• MBI Deep Dives breaks down pivotal companies and sectors.

• The Dutch Investors are long-term investors who publish very good sector research. Good for long-term trends.

• Buying great companies when they are beat up can be a successful strategy. Rebound Capital watches that market and publishes regular deep dives and investment theses on the subject.

• Jimmy's Journal is packed with how-to guides more than deep dives. Great resource for leveraging AI to help your portfolio and for doing your own diving.

Charts That Actually Teach You Something

Visuals aren’t decoration—they’re insight in compressed form. Good charts reveal patterns you’d miss in text, showing where markets pivot and how money actually moves. Here’s where I consistently find well‑sourced, thought‑provoking examples.

• Adam Tooze’s Chartbook drops a well-picked handful of the most important big-picture graphs in your inbox every few weeks.

• Robinhood bought Sherwood News, but they have kept publishing the very interesting Chartr, a daily dose of data for your perusal. Related is their evening publication, Snacks, which does a good job ferreting out the important market story of the day often with good visuals.

• Bruce Mehlman publishes Age of Disruption. The key feature is his Six-Chart Sunday. It is not a market-focused publication per se, but the data is often economic and it is almost always at least market-adjacent and market-moving information.

• Macro is a dark art, but Russell Clark does a great job drawing the picture in Capital Flows.

What About Crypto?

Crypto is interesting, and you can certainly invest in it. But there are a lot of things to invest in, and I have been in stocks a long time so I choose to focus my energy there. I don’t know enough to give recommendations on the subject.

Your Mileage May Vary

Good reading compounds like capital — if you pick the right sources. These publications have helped me manage mine. I hope they help you in your investment journey.

This article does not constitute financial advice. Past performance does not indicate future gains. Market conditions vary. Your money is your money and you should consult your own appetite for risk, personal situation and advisors.

The Distilled Spirit

The Big Picture

👦 TweenFluence: Meet Gen Alpha (Casey Lewis)
A cultural study into a generation that has not known life without the algorithm. This is an amazing window into the world your tween lives in and to what will shape the future.

🏠 What Case-Schiller is Really Saying (Erdmann Housing Tracker)
The Case-Schiller home price index shows home prices shooting upwards. Constrained supply of homes and mortgages is creating a price squeeze and conditions where new home buyers are filtering up in income.

🤖 16 Charts That Explain the AI Boom (Understanding AI)
AI is clearly booming, here are sixteen important data points in visual format.

Deviance and Risk

😜 Take Weird Ideas Seriously (Packy McCormick)
Weird ideas create alpha for you and for society. Take them seriously.

🤷‍♂️ Where Have the Wierdos Gone? (Experimental History)
People are less weird today. There is just not as much variance. Explore the data and the reasons people are less deviant today.

💸 The Lotteryification of Everything (Dopamine Markets)
There has been an explosion of products designed to take your money in highly engineered lotteries.

How To AI

📺 Peter Yang AI Tips (Peter Yang)
Really amazing insight into how one of the best uses AI tools today. Projects are very powerful now.

☄️ Comet→Substack Workflow (Cash & Cache)
How one author successfully used Comet to help him write his posts.

📖 Learning with Perplexity & NotebookLM (AI Made Simple)
How to combine Perplexity and NotebookLM to collect and visualize research.

💬 25 AI Pro-Tips (The PyCoach)
25 tips about using ChatGPT and other common AI tools from one of the best.

📓 Hands on Guide to NotebookLM (Joel Salinas)
NotebookLM has become amazing of late. Here is one expert’s guide to how to get the most out of the platform.

Leading and Advising

🚆 Dual Track Agility (The Maverick Mapmaker (on Multidisciplinary Teams & AI))
Scrum is a relic and will be done in by AI. We need separate lanes for machines.

🏎️ Driving at 200mph (Joe Magerramov)
Coding is different now. You can do it very fast, but you need downforce to keep it on the track. Coordination is a big challenge.

👁️ 54 Observations About The World (The Generalist)
A great list of thought hacks about the world.

🧑‍💼 6 Leadership Tactics That Work (The Good Boss)
Six solid tactics for getting better results from your team.

Fun Stuff

🍺 Drinking Licenses for College Students? (No Dumb Ideas)
Not as crazy as it sounds.

🎃 Halloween Keeps Getting Bigger (Reading the Zeitgeist)
ICYMI, Halloween is a bigger thing. Maybe it is more than commercialization?

⚾ The Dodgers are NBA-Style Champions (Neil Paine)
The dodgers are built on megastars and used NBA-style load management on their way to a title.

🎂 Dot Com at 40 (Dot Com Press)
The concept of .com domain names turns 40 this year. Here is a cool timeline of how that came to be.

💾 Digital Dark Age (BBC)
Treasured documents are locked up on hard-to-read floppy disks.

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