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.

This episode is with Christopher Burns, the creator of c15t and founder of consent.io, an open-source, developer-first, ethical provider of privacy infrastructure. Chris explains why most cookie banners are not compliant, and if the EU is going to come after you for it. We talk about how he found product market fit and grew the company, and we also debate London vs SF for startups.Links: • Chris' Linkedin • c15t • ConsentThis 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 is the story of how Amazon Web Services - arguably the most successful developer tool of all time - got started. 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.

Adam Frankl has been the first Marketing VP at three dev-facing unicorns. He returns to the podcast, to reveal the things that DevTool startups must get right in the early days, in order to be successful. We also discuss Jack's experience implementing Technical Advisory Boards (TABs) with a new startup, and the hurdles startups face with outreach, sustaining member enthusiasm across calls, and the art of framing the problem correctly. Adam shares ongoing AI experiments to streamline TAB insights and stories that hook developers.​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: • Adam's Linkedin • The Developer Facing Startup

Kyle Cheung, co-founder of Greybeam, shares how his team built a tool that reduces Snowflake costs by 70-95%, without migration, drawing from multiple pivots over two years. The discussion covers their quirky marketing tactics and advice on fundraising as storytelling.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: • Kyle's Linkedin • Greybeam

In this episode, Matt Klein (Bitdrift, Envoy) reflects on building EC2 in the early days of AWS, the reality behind AWS’s origins, and what Amazon’s customer obsession looks like from the inside. He then dives into creating Envoy at Lyft, the challenges of open source at scale, and spinning Bitdrift out of Lyft to focus on mobile observability. He shares how to meet developers where they are and what it takes to find product market fit. 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: • Matt's Linkedin • Bitdrift

Will Stewart is the CEO and co-founder of Northflank, the developer platform. He shares how a teenage gaming side project turned into a self-service developer platform that runs complex workloads on Kubernetes across any cloud. He talks about meeting his co-founder online, fundraising and hiring remotely and why they took years to launch. He offers some interesting insights on dealing with bugs, product vision and changelogs.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: • Northflank • Will's Linkedin

In Shawn "swyx" Wang's third appearance on the podcast, we talk about his recent interview with Mark Zuckerberg and Priscilla Chan about AI in biomedical research, and the goal to understand and eventually eradicate all diseases. We also talk about how DevRel is unbelievable back, the challenges of uphill DevRel, the dynamics of the current AI investment bubble, and the new projects he is working on.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: • Uphill DevRel article • DevRel is unbelievably back article • Particle/wave duality article • The Economics of Superstars • AI Engineer conference videos • Swyx's Linkedin