Little Might
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Illustration of Cathryn Lavery at a desk, surrounded by a laptop, a 3D printer, a small robot, and an open notebook of handwritten notes.
Cathryn Lavery

Cathryn Lavery · Builder & Operator · Est. 2013

I learn by doing. Then I write down how.

For operators getting technical, and builders learning to operate.

I go deep on one hard thing at a time, then write down exactly how to do it yourself. The topic keeps changing; the method doesn’t.

My best stuff is in my email.

My goal is for it to be the most useful email you read that day.

No spam. Unsubscribe in one click.

Gone deep on: Productivity Kickstarter DeFi Business AI

Writing since

2013

13 years of annual reviews, wins, and wrong turns.

Essays in the archive

160

From Kickstarter to crypto to AI agents.

These days

Building & learning

I own BestSelf, consult, and invest in building what’s next.

Featured on

Fox Business Entrepreneur The Wall Street Journal The New York Times CNBC Forbes Business Insider MTV

The latest

YC Summer 2026: the full batch, plus 7 of my favorites

7 that caught my attention, followed by every publicly listed startup in YC’s Summer 2026 batch.

ai tools entrepreneurship
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Start here

The signature essay

I Sold My Company, Then Bought It Back

How I walked away from my own company — and why I couldn't stay gone.

Read the essay

An employee stole $230k from my company

What you learn about people — and yourself — when the money disappears.

Why 50/50 partnerships are lazy

The math problem nobody solves before they sign.

How I built my wife a personal AI assistant

The tech took a day. Understanding how she'd actually use it took a week.

First 100 days: buying my business back from private equity

What I fixed, what they broke, and what 100 days of rebuilding taught me.

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writing 110 business 27 productivity 23 life lessons 23 finance 20 ai tools 18 video 18 guide 17 learning growth 17 ai 15

Recent Writing

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$ start ai-native

Free 7-day challenge

Make AI work
the way you work.

You're using AI. It's giving generic answers because it doesn't know who you are. Seven emails fix that — a context file, a skill, and four terminal commands. I went from never opening a terminal to 9,896 GitHub commits. This is the starting line.

No fluff. Each email has one thing to do.   See what's inside →

  1. 01 A year ago I'd never opened a terminal
  2. 02 What does ChatGPT actually think of you?
  3. 03 The one file that changes every AI conversation
  4. 04 I fired our Shopify agency and built my wife an AI assistant
  5. 05 Open the terminal. I'll tell you exactly what to type.
  6. 06 The things I didn't expect AI to change
  7. 07 Tell me what you built

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