Jun 14
267: Snake Oil —
The most capable people often struggle most with self-promotion. Jason Shen reframes the fear of being a 'snake oil salesman' by exploring the surprising history of actual snake oil.
Jun 08
266: Making a Real Difference —
Most nonprofits focus on feeling good or looking good rather than doing good. Jason Shen explains why a theory of change matters for anyone trying to create lasting impact.
May 31
265: What's the Point? —
When ambitious people lose their sense of purpose — whether from struggle or success — things go sideways fast. Jason Shen shares two coaching stories about rediscovering what matters.
May 25
264: Signaling Quality —
Before you can prove your substance, you have to signal your quality. Jason Shen explains why presentation determines whether you get the chance to demonstrate what you can really do.
May 18
263: The Tyranny of Thirty —
The pressure to 'make it by 30' has become a cultural epidemic. Jason Shen examines how the Forbes 30 Under 30 list and early-success myths created an artificial deadline that's ruining a generation.
May 11
262: Diminishing Returns on Merit Badges —
After your first few prestigious credentials, the returns on more 'merit badges' diminish fast. Jason Shen explains when chasing validation stops serving you and what to pursue instead.
May 02
261: Making Gut Calls —
Your gut intuition is only built when you actually follow it. Jason Shen shares a founder coaching story about trusting instincts over sunk costs and social pressure.
Apr 26
260: Fraught Conversations —
When disagreements get tangled with emotions, they become 'fraught conversations.' Jason Shen shares three practical tools for resolving conflicts with cofounders and close collaborators.
Apr 05
259: Off Track at 30 —
A reader writes in panicking about turning 30 with a failed startup and dwindling savings. Jason Shen responds with hard-won wisdom about 'established adulthood' and the surprises your thirties hold.
Mar 29
258: Manager Initiative [Ask Jason] —
When managers won't take initiative, the problem is usually the founder's transition from doer to delegator — not the manager's competence. Here's how to fix it.
Mar 22
257: Threshold Checkpoint Goalsetting —
Smart founders get stuck overthinking strategy. Jason Shen introduces Threshold Checkpoint Goalsetting — a framework for making decisions under uncertainty without constant second-guessing.
Mar 14
256: I'm Your Daddy —
A raw, week-one snapshot of new fatherhood. Jason Shen shares what surprised him about having a newborn — from the naturalness of caregiving to the surreal moment of hearing 'daddy's here.'
Feb 09
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.
Feb 02
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.
Feb 02
Pre-Fatherhood 🎬 —
Initial expectations around becoming a Dad
Jan 18
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.
Jan 11
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.
Jan 04
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.
Dec 15
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.
Dec 08
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.