255: The Dizziness of Freedom
More freedom means more anxiety. Jason Shen connects Kierkegaard's philosophy to the founder experience — and explains why commitment, not optionality, is the antidote to existential overwhelm.
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
235: A Brief Interlude
Jason Shen announces the birth of his daughter Ashton and reflects on the surprising parallels between parenting and coaching — both are about cultivating human strengths and helping people thrive.
Pre-Fatherhood 🎬
Initial expectations around becoming a Dad
234: How to Reset
When ambitious people crash — a failed product, a departed cofounder — they either scramble or freeze. Jason Shen borrows from gymnastics to explain how to rebuild momentum from the ground up.
233: Analogies are OP
Analogies are one of the most powerful tools in coaching, communication, and creative problem-solving. Jason Shen explains why metaphors make complex ideas stick and how to wield them effectively.
232: Why Founder Mode Works
Jason Shen's MIT Sloan Management Review article explains why founder-led companies outperform: domain expertise, earned legitimacy, and stakeholder forgiveness create unique strategic advantages.
231: The Early-Stage Crucible
Early-stage founders face a trifecta of challenges: no product-market fit, team conflict, and personal doubt. Jason Shen maps the patterns he sees in his coaching practice.
230: Choosing Better Customers
Your early customers shape your company's future. Jason Shen explains why chasing enterprise money while building for startups often backfires — and how to choose customers who push your product forward.
229: Lessons & Anti-Lessons from Gymnastics
After 16 years in competitive gymnastics including a national championship at Stanford, Jason Shen shares the positive lessons and maladaptive mindsets the sport instilled in him.
228: Building 10x Better
Building something 10x better sounds impossible for a tiny startup. Jason Shen explains how narrowing down — like Bezos selling only books for four years — makes the seemingly impossible achievable.
227: The History in Our Habits
We don't always know why we do what we do. Jason Shen shares his father's story of never finishing a glass — a habit rooted in China's Cultural Revolution — and why self-empathy matters.
226: Write It Out
When cofounder conflicts get emotionally charged, face-to-face conversations often fail. Jason Shen makes the case for letter writing as a powerful tool for resolving deep business partnership disputes.