Essays by Ry Walker
Essays on AI, startups, and software engineering by Ry Walker, founder of Tembo and Astronomer.
| Feb 6, 2026 | Outbound Sales is Broken in 2025 (And AI Won't Save It) AI outbound scales noise, not trust. Why cold outreach is saturated in 2025 and how warm, relevant paths still win. |
| Feb 5, 2026 | The Underrated Power of a Positive Attitude A case for genuine positivity in leadership: it compounds encouragement, builds resilience, and avoids toxic positivity. |
| 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. |
| 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. |
| Jun 9, 2022 | The Startup Pitch That Actually Gets Funded A battle-tested framework for seed-stage pitches: the four pillars that matter (product, team, traction, market) and five steps to nail them. |
| Oct 31, 2017 | The Quest for a Lead Investor How fundraising really works: you'll get a pile of 'no' and a smaller pile of 'maybe.' Without a potential lead in that maybe pile, you're not ready. |
| Jan 27, 2016 | Our Review of AngelPad: "Game Changing" Our journey through AngelPad as the first Midwest team ever accepted. From application to Demo Day, here's what the top-ranked accelerator is really like. |
| 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. |