Essays by Ry Walker

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

Feb 6, 2026Outbound 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, 2026The Underrated Power of a Positive Attitude

A case for genuine positivity in leadership: it compounds encouragement, builds resilience, and avoids toxic positivity.

Feb 3, 2026Going 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, 2023How 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, 2022The 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, 2017The 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, 2016Our 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, 2015Professional 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, 2015Don'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, 2014Collect Stories of Astonishment

Build something astonishing for your early adopters. Measure their amazement across education, setup, and ongoing value—then track your improvement.