I've spent over a decade in the startup world — as a Y Combinator founder (Ridejoy, W12), a product builder (Headlight, Midgame), and a startup coach working with 100+ founders navigating everything from first fundraise to acquisition. These posts capture the hard-won lessons from that journey.
Whether you're raising your first round, pivoting for the third time, or wondering if you still have the fire, this page collects my best thinking on the craft of building companies and the mindset required to survive the journey.
The Founder Mindset
- "You Have to Be a Little Delusional" — Why irrational optimism is a feature, not a bug, of great founders
- Winner's Mindset — How mental toughness in athletes translates directly to entrepreneurial resilience
- Two Feelings You Need Before Starting a Startup — The emotional signals that tell you it's time to make the leap
- Long-Term Conviction, Short-Term Confidence — Build durable conviction through a deliberate practice of progressive risk-taking
Building & Strategy
- Building 10x Better — Narrow your scope ruthlessly to build something meaningfully better than the alternative
- Choosing Better Customers — Why the customers you pick early on shape every future decision
- Solve for the Harder Problem — Resist the easy fix and tackle the problem that actually moves the needle
- Why Founder Mode Works — The structural advantages that founder-led companies have over professional management
Pitching & Persuasion
- Eleven Compelling Startup Pitch Archetypes — Proven narrative structures to make your pitch stick with investors
- Make the Case — Frame your business case from the buyer's perspective to close faster
- Snake Oil — Reframe self-promotion as a necessary skill, not a character flaw
Navigating the Hard Parts
- The Early-Stage Crucible — The trifecta of challenges every early-stage founder must survive
- The Double-Loop Pivot — A structured framework to decide when and how to change direction
- Treading Water — A reality check when your startup feels stuck and momentum has stalled
- Write It Out — Resolve cofounder conflict through structured letter writing before it destroys the company
Founder Lessons & Reflections
- Ridejoy: Lessons Learned — The unvarnished postmortem from my own startup's rise and fall
- Burned-Out Tech CEO to Warehouse Associate — What happens when a founder hits absolute bottom — and what comes after
- From Zero to Unicorn — The arc from founding to billion-dollar outcome and what it actually takes
- How Near Misses Lead to Success — Why coming close to failure can be a better predictor of future success than early wins
- Lessons and Anti-Lessons from Gymnastics — The athletic habits that help founders — and the ones that hurt them
If you're a founder navigating a transition, I work with startup leaders as an executive coach. Learn more about coaching at jasonshen.com/coaching or read my book, The Path to Pivot, at jasonshen.com/books.