The Outlier Advantage

The Outlier Advantage

A weekly dispatch on the frameworks and mental models for founders and builders who want to win the long game.


You're a high-performer, an outlier, a creative misfit. The standard playbook for success feels like it was written for someone else—it glorifies burnout, rewards conformity, and whispers "keep your options open" whenever you dare to commit.

This newsletter offers a different approach.

Each week, I bridge the gap between seemingly separate worlds: from elite athletic training, to the psychology of high-stakes decision-making, and the hard-won truths of building in Silicon Valley. You get one actionable framework, mental model, or method you can use immediately.

This isn't just about getting more done. It’s about building a fulfilling business and life that doesn't just look good, but feels good too. We explore:

Think of this as your weekly session with a coach who’s been in the arena: elite athlete, YC founder, and Big Tech PM. Someone who knows the theory but trusts the scars more. If you're ready to stop grinding and start building a more powerful, sustainable way to win, this is for you.

If you're tired of generic advice and ready for an operating system built for your unconventional mind, join thousands of other ambitious outliers.

Previous issues:

261: Making Gut Calls
What no one ever explains about building your gut intuition
260: Fraught Conversations
3 proven techniques for getting through messy disagreements
258: On Fostering Managerial Initiative [Ask Jason]
A frustrated CEO asks how they can get their “Head of” to take more responsibility
234: How to Reset
When you’re stuck in a rut, forget the distant future. Focus on now.
231: The Early-Stage Crucible
The triad of challenges that most early stage founders face
232: Why Founder Mode Works
My new piece in MIT Sloan Management Review
190: How to Do Great Work
💡Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen. A couple of months ago, I wrote about timeless pieces of wisdom that I come back to again and again. 153: Timeless WisdomUnpacking wisdom on solving problems, managing

About Jason

Jason Shen is an xecutive coach who works with founders and ambitious outliers to reverse conviction decay, claim their genius, and win at their won game. As the author of The Path to Pivot and weirdly brilliant, he is a leading expert on resilience, transition, and unconventional success and his ideas have appeared in MIT Sloan Review, TechCrunch, FastCompany, and Every.

Jason previously founded 3 venture-backed startups (1 exit) and led product teams at Etsy and Facebook. He is a two-time Stanford graduate, a Y Combinator alumni, and NCAA mens gymnastics national champion. He lives in Brooklyn with his wife Amanda, a contemporary artist, and is a board member of Lunar Accel, an AAPI leadership development nonprofit.