Essays by Ry Walker

Essays on AI, startups, and software engineering by Ry Walker, founder of Tembo and Astronomer.

astronomer automation bottleneck build-vs-buy business-model code-review coding-agents communication competition context context-engineering coordination culture customer-development customer-success data decision-making developer-experience developer-tools devex economics engineering enterprise evaluation experience founders fundraising future go-to-market governance growth gtm human-in-the-loop incentives infrastructure integration intuition judgment knowledge-management knowledge-work kubernetes leadership learning maintenance management market marketing measurement memory moats nuance observability open-source operationalization operations outbound personal personal-agents personalization phases pitching platform platforms playbook process procurement product prototyping quality rag reasoning recommendations retention review sales security seed shipping skills software-engineering startups storytelling strategy

tembo tooling trust unit-economics workflow

May 6, 2026	What I Learned Shutting Down OSSRank We built OSSRank to score open source project health beyond GitHub stars. The framework was right; the product wasn't. Here's what I took away.
May 4, 2026	Provocatypes Over Roadmaps A provocatype is a prototype built to provoke conversation, not to ship. When the product shape is genuinely unknown, provocatypes surface assumptions that requirements gathering misses.
May 3, 2026	Pluck a Feather From Each Goose Following every engaged customer ends with three products instead of one. The discipline is to pluck a feather from each passing goose and follow none absolutely.
May 1, 2026	Start With the Pain, Not the Platform The temptation with agent projects is to start with the technology. That is how you end up with a demo that impresses nobody who actually has to use it.
Apr 29, 2026	Users Should Iterate on Agents, Not Developers Agents are always slightly wrong when first built. The people who know what is wrong are not developers — they are the users who interact with the agent every day.
Apr 26, 2026	The Grayscale Between Engineering and Everywhere Else There is no clean split between coding tools and business tools. The reality is a grayscale, and the products that win serve the whole spectrum.
Apr 26, 2026	The IKEA Effect Is Real for Agent Tooling People pay 63% more for furniture they assembled themselves. The same dynamic governs agent platforms — developers who build their own agents care about them and keep improving them.
Feb 3, 2026	Going Stats-Free: Why Sometimes the Numbers Don't Matter Why rigid metrics can slow decisions when data is noisy, and how intuition plus small experiments can guide better calls.
Feb 1, 2026	Finding the Balance Between Data and Intuition A practical middle ground. Use data where stakes are high, intuition where speed matters, and intellectual honesty everywhere in between.
Jun 14, 2023	How to Test a Software Startup Idea A step-by-step framework for testing startup ideas: talk to users, fake the demo, iterate until you know what to build. Don't write code yet.
Feb 16, 2023	The Dual Flywheels of Modern Open Source Commercialization Open source your core, build a SaaS around it ASAP, and keep both flywheels spinning. How to balance community and commercial traction.
Aug 28, 2015	Professional Services for an Early Stage SaaS Company Should early-stage SaaS companies do professional services? Advice from Brad Feld, Hiten Shah, and other investors on the product vs. services dilemma.
May 25, 2015	Don't Sleep on User Retention Most startup advice focuses on product and marketing. Retention gets far less airtime—and that's a shame, because it's where most products die.
Dec 28, 2014	Collect Stories of Astonishment Build something astonishing for your early adopters. Measure their amazement across education, setup, and ongoing value—then track your improvement.