222: Treading Water
Surrounded by high achievers, it's easy to feel like you're going nowhere. Jason Shen offers a four-part reality check for founders who feel stuck while everyone else seems to be winning.
Jason Shen
The Outlier Coach—helping founders build companies they can be proud of with partners who truly have their back · 3x venture-backed startup founder (acq by FB) · Author of 'The Path to Pivot' & 'Weirdly Brilliant' · ADHD · Former NCAA gymnast
221: Best Practice
Industry best practices don't always apply to you. Jason Shen draws on sprinter Michael Johnson's unconventional stride and Paul Graham's Founder Mode to argue for finding your own personal best practice.
220: Productivity Judo
There's no single productivity system that works forever. Jason Shen shares a meta-strategy of rotating tactics — from body doubling to environment changes to unconventional task management.
219: Long Term Conviction & Short Term Confidence
Conviction is the most persuasive quality a founder can possess — and it's built through progressive risk-taking. Jason Shen connects gymnastics training to the psychology of entrepreneurial belief.
218: How to Conference Better
Most of a conference's value comes from what happens outside the planned programming. Jason Shen shares tactical advice for founders on networking, speaking, and making the most of industry events.
217: Read This Before You Hire an Executive / Founder Coach
Thinking about hiring a coach? Jason Shen breaks down what coaching actually delivers — clarity, conviction, and momentum — and how to find the right fit for your needs.
216: Learning to Speak Naturally
Giving a rehearsed speech and speaking naturally to camera are two entirely different skills. Jason Shen shares lessons from Ultraspeaking's Creator Cohort on overcoming speaking anxiety.
215: "You Have to Be a Little Delusional"
A talk on startup pivoting from Medium Day 2024: why founders need productive delusion, and how the Double Loop Pivot framework helps struggling startups find their next direction.
214: A Weirdly Brilliant FAQ
Jason Shen answers the most common questions about his book Weirdly Brilliant — a guide for ambitious outliers who want to swing big, own their genius, and play a different game.
213: Two tech interviews that are four decades apart
Steve Jobs in Playboy (1985) & Threads/IG chief Adam Mosseri in Platformer (2024)
212: Writing a book in 30 days
Never let a good deadline go to waste
211: "Good writing is the Grammarly fixes you ignore"
On good writing and good characters