Jason Shen
The Outlier Coach
About
First‑gen immigrant and Stanford gymnast turned YC founder.
My journey: New England grit → Silicon Valley insight → New York hustle. Three startups, one Facebook exit, and two books (The Path to Pivot, weirdly brilliant) later, I help ambitious misfits build careers that excite them long after the applause fades.
My coaching blends startup battle scars with championship-athlete discipline so founders and outliers from Y Combinator, Meta, and Google can make bold moves without losing their souls.
Weird brilliance beats conventional mediocrity—let’s wield yours.
My journey: New England grit → Silicon Valley insight → New York hustle. Three startups, one Facebook exit, and two books (The Path to Pivot, weirdly brilliant) later, I help ambitious misfits build careers that excite them long after the applause fades.
My coaching blends startup battle scars with championship-athlete discipline so founders and outliers from Y Combinator, Meta, and Google can make bold moves without losing their souls.
Weird brilliance beats conventional mediocrity—let’s wield yours.
Packages
Win Your Year (2025 Annual Review & Vision Workshop)
A live workshop that walks you through a thoughtful review of 2025 and gives you the clarity, insight, and momentum to step confidently into 2026.
Date: Saturday, January 3 at 1:00 PM Eastern
Date: Saturday, January 3 at 1:00 PM Eastern
Land Your First Client (with $24k/mo fractional content lead)
A live workshop showing you how to package your expertise, build a simple landing page, and land your first client using a clear 90-day plan.
Mining for Genius [Replay + Worksheet + AI Wizard]
Reveal the repeatable patterns in your proudest wins and walk away with a personalized “Genius Dossier” in one afternoon
The High-Leverage Sprint [Workshop Replay + Tools]
Clarify your highest-leverage move and build a 3-part execution plan that drives real momentum between now and December 21.
Play Your Game [video replay + worksheet + AI wizard]
Define the game you’re playing to win and lock onto the prize that truly matters—so you can stop chasing the overrated objectives everyone else is sprinting after.
Own the Narrative [Workshop Replay + Tools]
Transform your scattered experiences into a magnetic story that opens doors, builds trust, and makes people want to champion your success
The 90-Day Note [Workshop Replay + Tools]
A 2 min quarterly update that reconnects you with your network, sparks new opportunities, and keeps your name top-of-mind—without spending an entire weekend writing it.
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The Conviction Reset
A private 1:1 coaching sprint to reverse conviction decay and recover your inner certainty
Back in Business [Partnership Intensive]
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Cofounder Conflict - Full Repair (ongoing)
View detailsBook a free introductory call
Let's meet online and see if we are a good fit