Archive - Optima & Outliers

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

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