May 18
263: The Tyranny of Thirty —
My piece in Medium on the artificial deadline that’s ruining a generation
May 11
262: Diminishing Returns on Merit Badges —
On the pursuit of external markers of success
May 02
261: Making Gut Calls —
What no one ever explains about building your gut intuition
Apr 26
260: Fraught Conversations —
3 proven techniques for getting through messy disagreements
Apr 05
259: Off Track at 30 —
A high achieving reader struggles in the messy middle of startup life
Mar 29
258: On Fostering Managerial Initiative [Ask Jason] —
A frustrated CEO asks how they can get their "Head of" to take more responsibility
Mar 22
257: Threshold Checkpoint Goalsetting —
An action-oriented framework for executing under uncertainty
Mar 14
256: I'm Your Daddy —
Reflecting on the first week of parenthood (video)
Feb 09
255: The Dizziness of Freedom —
Why ambitious founders escape angst through personal commitment, not endless options
Feb 02
235: A Brief Interlude —
Becoming a Dad and unconventional advice for creative job seekers
Feb 02
Pre-Fatherhood 🎬 —
Initial expectations around becoming a Dad
Jan 18
234: How to Reset —
When you're stuck in a rut, forget the distant future. Focus on now.
Jan 11
233: Analogies are OP —
How to rapidly build rapport and communicate complex ideas
Jan 04
232: Why Founder Mode Works —
My new piece in MIT Sloan Management Review
Dec 15
231: The Early-Stage Crucible —
The triad of challenges that most early stage founders face
Dec 08
230: Choosing Better Customers —
All revenue is not created the same. Early on, startups should prioritize product learnings from engaged early adopters.
Dec 01
229: Lessons & Anti-Lessons from Gymnastics —
Being an elite gymnast instilled several great lessons on high performance, and a few bad ones too
Nov 23
228: Building 10x Better —
Why founders have to narrow down and compound to create truly exceptional products in the post Chat-GPT era
Nov 16
227: The History in Our Habits —
What founders can learn from the hidden psychology driving our daily behaviors
Nov 09
226: Write It Out —
Using letters to work through severe cofounder conflict