The Outlier Advantage

The Outlier Advantage

A weekly newsletter for atypical achievers to defy convention & find breakout success


The Outlier Advantage is a weekly letter by Jason Shen that explores how founders, senior leaders, and outlier achievers can defy convention and find breakout success on their own terms.

Every weekend I send you 600-800 words about topics that come up in my coaching practice:

The Outlier Advantage is read by more than 2,800 founders, leaders, and outliers at Google, Facebook, Brex, top Y Combinator-backed startups, and leading Silicon Valley venture capital firms.

Previous issues:

220: Productivity Judo
16 tactics I use to wrestle with my ADHD brain
179: Being an Outlier
Getting a Kindergarten PIP and what to do when you feel remarkably different from your peers.
190: How to Do Great Work
đź’ˇCultivating 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
153: Timeless Wisdom
Unpacking wisdom on solving problems, managing projects, telling stories, and driving movements that have stood the test of time.
181: Strong Suit
Three ways to make your outlier obsessions an advantage you as an outlier
219: Long Term Conviction & Short Term Confidence
There’s no shortcuts to full throated, high quality belief in what you’re doing

About Jason:

Jason Shen is a writer and executive coach who works with outlier founders and senior leaders to build conviction in new ventures. As the author of The Path to Pivot and weirdly brilliant, he is a recognized expert on resilience, transition, and unconventional success.

Jason previously founded 3 venture-backed startups & 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.