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Myles Marino

Writings and essays by Myles Marino on business, investing, and strategy

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The Long Walk: Shipping Your Writing

§ July 2025 The honeymoon is over. The first draft was a thrill. Now, it's a tombstone in the ‘review’ folder. Here’s how you ship: 1. Slay the Enemy. Your enemy is fear. You feel it now. A tightness in your stomach, the knot in your throat. The whisper of the critic: “This sucks. Everybody will call you out on it.” This is the fear of shipping the imperfect. This is the final battle. 2. Find the…

Staring into the Void

Staring into the Void - by Myles Marino

Learning from the best traders

Key lessons from the best traders like Soros, Druckenmiller, and Michael Marcus on what you can do to become a better investor

Investor and Operator Resources

Curated collection of resources from great operators and investors including Warren Buffett, Peter Thiel, Jeff Bezos and more

Sum: Forty Tales From the Afterlives

My thoughts on David Eagleman's book exploring different concepts of the afterlife

Dirtbags can't sell

The only sales guide you will ever need: successful sales is the practice of radical empathy

Net-nets in Private Markets: RockRose Energy Case Study

How RockRose Energy acquired Marathon Oil's UK business and got paid to do it.

Book Notes and Big Ideas

Key insights and big ideas from books I've read on investing, business, philosophy, and more

Anatomy of an Outage

How we diagnosed and fixed a critical authentication token expiration issue in our mission-critical software

KSPI - Myles Marino

Content coming soon.

How I Lost 20 Pounds by Learning to Hate

From January to July, the number on my scale dropped from 225 to 205. The secret wasn’t a punishing gym routine or a keto calculator. It was a targeted strike against a single enemy: my daily ritual of cracking open a morning Dr. Pepper and an afternoon Coca-Cola. That habit was the soundtrack to my day. The hiss-crack of the can, the sugary rush, the inevitable crash. Breaking a ritual woven so…

Richmond Spots and Interview Q&As

Collection of Richmond's favorite spots and Q&As with investors Zack Oliva and Mohnish Pabrai

I build a guestbook so you can say hi to me using PHP

A technical breakdown of the new guestbook feature, detailing the PHP backend, JavaScript frontend, user flow, and a quick fix for a common file permissions issue.

First Ave Networks: One of Ted Weschler's Best Investments

First Ave Networks is one of Ted Weschler's best investments. In this case study, we explore how it achieved 1236% returns in eleven years.

ECC Capital Corporation Investment

ECC Capital Corporation is a coal mine value investing play with potential upside

Avoid Competition: A Sam Zell Case Study

How Sam Zell's first real estate deal highlights the advantage of low-competition markets

The History of Clipboards and Computers

The history of clipboards and computers from TECO to modern systems

Buying CareCloud Preferred As

The Preferred A's for CareCloud could be a good investment.

Everything Is a Context Problem

The bots weren't dumb. They just didn't know anything. They read our in-house notes and guessed at the answer.

Transformer Engineers: Charlie Munger's First Deal Almost Broke Him

How Charlie Munger's worst business taught him the one lesson that made Berkshire Hathaway possible.

The Mistake Is in the Magnitude

The crowd can decipher the direction of a mega-trend. Where nearly everyone goes wrong is in estimating its magnitude.

Joel Greenblatt, the Activist

In 1994, Joel Greenblatt launched his first and last hostile activist campaign at Alliant Techsystems — the same year he made an effortless 40% on American Express.

Costly Delusions and Self-Improving Engines

Believing you can one-shot your LLM problems leads to frustration, wasted engineer time, and runaway spend. Here's the framework we use instead.

Muscle Memory

When you rebuild an interface, you're not just changing the UI — you're breaking habits your users have spent years building.

What AI Actually Does to Legacy Software

How we used AI to migrate 282 hand-pasted payment buttons from a twenty-year-old system — what it got right, what it got wrong, and what only a human could decide.

The 50th Percentile Deadline

Why Musk aims for deadlines he'll miss half the time, and how to apply the same principle to daily work.

The JustinBot: Devouring Our Support Inbox With AI

How we built our own AI support bot to handle 80% of Tier 1 requests by giving it the full context of a user's account, not just our documentation.

Be Involved

Reading the front page of the Wall Street Journal was never supposed to be a party trick. It was supposed to get you involved.

Building on Platforms

Platform apps are high-margin, stable, and could get nuked overnight. Here is how we think about the trade-off.

Speed Traps in the LLM-Era

How AI-assisted development tempts us into building the wrong things faster, and why taste matters more than ever.

How to See Everyone When You Travel

Stop doing one-on-ones. Invite six people for bagels in Central Park and let the group take on a life of its own.

The Language of Shiny Objects

Why calling legitimate work a "shiny object" is demoralizing — and the framework I use instead to talk honestly about prioritization.

The Creation of an Algorithm

95% of artists on EntryThingy have only ever submitted to one gallery. Here is how we built a recommendation algorithm to change that.

2025 Vendor Audit: Every Tool We're Keeping, Killing, and Replacing with AI

We went through every vendor on our credit card statements to answer one question: who survives 2026? Here is the full breakdown.

The Engineering of a Meme: Why the "China is Engineers" Narrative Went Viral

Tracing the intellectual lineage of Dan Wang's "Breakneck" and how a century-old idea became Silicon Valley's favorite geopolitical framework.

Ignoring the Infinite Canvas

How to choose what to build when every option seems reasonable. A framework for focus in a world of infinite possibilities.

Things on my reading list

A bunch of books that I would like to read in no particular order.

The best ideas were never meant to be published

A curated database of history's best internal memos. Skip the fluff and learn from the private correspondence that changed industries. Open source.

How Buffett Would Earn 50%+ Returns

Buffett talks a lot about how he would invest and manage a portfolio to earn high returns on small sums of money. Here, I lay out what I think he would do and why.

Why Read Biographies?

Biographies work because they hand you a framework, not a fact. Organizational and historical accounts have too many variables to extract anything repeatable.

The Edge of Reason

Peter Theil's secrets aren't the primary driver of value. Great companies are built on visible truths that are undervalued.

The Founders

How early PayPal prospered through internal strife and external headwinds.

The Wright Brothers - Creating your own expertise

The Wright Brothers' success was born from favoring their own data and conventions rather than those of so-called experts,

Good design is apparent

Good design is all about reducing questions and being obvious to the user

The Wright Stuff

How the Wright brothers out-competed those with 100x more funding.

The Only Rule Is It Has to Work

How the Stompers tried to solve coordination issues for their statistically oriented baseball team.

We are not a fraction of the universe, but indeed mirrors of our effort

An exploration of cynicism vs. optimism. How our approach to effort and opportunity shapes our reality, proving that both the cynic and the optimist are right.

Your emails are being ignored, and here's how to stop sabotaging yourself

Learn how to stop sabotaging your emails. Tips on clarity, making replies effortless, formatting for scannability, and writing compelling subject lines.

Seven Days in the Art World

A reflection on the levels of the art world and one simple truth: artists are doers. Discover how these insights shape the mission of EntryThingy.

The Constellation Paradox: Building an Empire on Earned Constraints

Constellation's returns are forged by a system of self-imposed constraints. These are not arbitrary rules; they are disciplines built upon hard-won, earned secrets about value, people, and time