Scaling DevTools

Andy is the cofounder of DeepTrace, an AI reliability platform that helps engineering teams investigate incidents and fix problems in production. In this conversation, Andy shares how a team of technical founders learned sales, got their first 10 customers, and approached go-to-market with the same mindset they used for engineering. We discuss outbound volume, messaging, targeting, sales tooling, paid ads, sales calls, pricing, trials, and the thinking behind DeepTraceLinks:Andy's LinkedinDeeptrace

Stefano Verna and Matteo Giaccone from DatoCMS share how their side project in a web agency turned into a €6.5M ARR company with a 13-person remote team. We talk about building sustainable, bootstrapped businesses, instead of the all-or-nothing VC approach, and about their 6-week shipping cycles, prioritizing simplicity, and building trust with customers.Links: •. Dato CMS •. Matteo's Linkedin •. Stefano's X

Ahmad Sadeddin is the founder and CEO of Corgea. Corgea provides the security tools to find, triage, and fix insecure code. Ahmad shares:- Why you don't need to raise much to find PMF - stay lean: you should surprise people with how few people you are.- What is a small amount to raise? And what team size do you need? - Pivoting during YC and how Corgea found their first customers and the signs of Product Market Fit- The journey to Product Market Fit never stops- How Corgea worked towards Product Market FitThis episode is brought to you by WorkOS. If you're thinking about selling to enterprise customers, WorkOS can help you add enterprise features like Single Sign On and audit logs.Links:Ahmad Sadeddin https://www.linkedin.com/in/asadeddin/Corgea https://corgea.com/The Fatal Pinch by Paul Graham https://paulgraham.com/pinch.html

David Hsu is the founder of Retool, the low-code platform for building internal tools used by companies like Amazon, Airbnb, and the US Army. David recounts building Retool's first version in weeks with just three components, early outreach failures, shifting to "tomorrow's developers," and LLM use cases.This episode is brought to you by WorkOS. If you're thinking about selling to enterprise customers, WorkOS can help you add enterprise features like Single Sign On and audit logs. Links: • Retool • David's Linkedin

Louis Knight-Webb is the co-founder of Vibe Kanban, an open-source tool for orchestrating AI coding agents. After years of building for enterprise legacy code, Louis pivoted and saw his new project explode to over 20,000 GitHub stars in just a few months. We talk about the "startup university" of the last five years, why he walked away from 6-figure enterprise deals to find true founder-market fit, and why he thinks most people are wrong about AI-generated pull requests.This episode is brought to you by WorkOS. If you're thinking about selling to enterprise customers, WorkOS can help you add enterprise features like Single Sign On and audit logs.Links: • Vibe Kanban • Louis' Linkedin

This episode breaks down an article by Jason Cohen, founder of WP Engine and SmartBear, outlining his step-by-step roadmap from idea to product-market fit (PMF) for startups, especially DevTools. His 8 step roadmap provides insights on personal fit, market validation, customer interviews, building an SLC (simple, lovable, complete) MVP, sales focus, retention, prioritization, and founder psychology, drawing from Cohen's unicorn success and pitfalls to avoid.Links: • Jason Cohen • WP Engine • Smart Bear • Jason Cohen's articleThis episode is brought to you by WorkOS. If you're thinking about selling to enterprise customers, WorkOS can help you add enterprise features like Single Sign On and audit logs.

This episode breaks down Marc Andreessen's 2007 article on why market matters most in startups, plus some great wisdom from Michael Seibel on spotting real PMF through explosive growth and customer pull.Links: • Marc Andreessen's article • Michael Seibel's post • Product Market Fit collapseThis episode is brought to you by WorkOS. If you're thinking about selling to enterprise customers, WorkOS can help you add enterprise features like Single Sign On and audit logs.