Archive - Optima & Outliers

Entrepreneurship As Recursive Price Discovery

Thinking about Startups from First Principles

Jul 16 •

June 2025

Money Gets Better with Age

When I told my wife I was writing this, she said "Do you really think people need to be reminded that it's good to make money?" I do.

Jun 16 •

O&O NYC Meetup: Show Off How You Talk To Claude

Jun 9 •

May 2025

Bad Advice, The Altruistic Case For IPOs, Process vs People and more with Charles Rubenfeld

I chat with Substacker and business nerd Charles Rubenfeld on quite a few topics of mutual interest.

May 16 •

and

Charles Rubenfeld

1:00:54

Dissecting Social Capital: Self-Interest, Reciprocity and Repeated Games

A friend recently told me about an awkward encounter.

May 13 •

April 2025

O&O NYC Meetup #2

Apr 15 •

March 2025

Recruiters as Accidental Underwriters: Why You Pay for Others' Poor Hiring Decisions

When I talk to founders, I don't have to work very hard to get them to complain about job boards and recruiters.

Mar 27 •

VCs as Unidirectional Market Makers

I feel the proudest when I can defend maligned and vulnerable groups so today the subject of my compassion is the VC industry (and no my fundraising…

Mar 12 •

Passing the Test vs. Getting It

I remember this moment in JP Morgan's training class, when I realized I was lying to myself that I understood the concept of diversification.

Mar 10 •

February 2025

Legibility vs. Liquidity

I had a great time meeting some of you at the NYC Meetup yesterday at Fractal Tech (shoutout to Andrew for hosting).

Feb 20 •

Weekly Mixed Bag #1

Starting this week, I'm introducing a new section featuring opportunities and links worth your attention - this could be events, fellowships, job…

Feb 16 •

What Do You Want Your Employees to Want?

Imagine you're wealthy and looking to hire someone to manage a pool of money.

Feb 10 •

Scalable Trust: A Remedy for the Selector’s Curse

I live in New York City and almost never help strangers who approach me.

Feb 6 •

Feb 3 •

January 2025

Dissecting Career Optionality

I'd make a terrible consultant.

Jan 21 •

December 2024

November 2024

What Business School Actually Buys You: Notes on Optionality, Signals, and Networks

In 2018, my boss gave me 17 reasons why business school was a bad idea and convinced me to stay.

Nov 17, 2024 •

Startup Hiring: Solving the Problem of Incentives and Trust

The Early-Stage Hiring Trap

Nov 14, 2024 •

Volatility Laundering: How to Tell if Your Non-Traditional Career is Actually Working

In my last post about career liquidity, I talked about how careers differ in how easily their value can be assessed and traded in the market - much like…

Nov 9, 2024 •

October 2024

India & Meritocracy: How India's Past Shapes What It Celebrates

Every year, India's newspapers devote prime front-page real estate to celebrating IIT-JEE toppers—students who excel in the brutally competitive…

Oct 31, 2024 •

ADHD and Managing Your Reputation

Paul Graham's essay titled "Good and Bad Procrastination" argues that procrastination can be virtuous when it means putting off small tasks to work on…

Oct 24, 2024 •

August 2024

Liquid vs. Illiquid Careers

Note: This is the first post in a series of posts about career liquidity.

Aug 3, 2024 •

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