How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)

David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO. In this episode, we discuss • How David went from managing a Burger King to landing his first job as a software engineer • How an code snippet grew into a ubiquitous monitoring platform • Why open source is an underrated distribution hack • How a ruthless competitive streak and obsession with excellence fueled Sentry’s rise • And so much more… Referenced • Aaron Levie: https://www.linkedin.com/in/boxaaron/ • Beats by Dre: https://www.beatsbydre.com/ • Cursor: https://www.cursor.com/ • Dan Levine: https://www.linkedin.com/in/danielmarklevine/ • Datadog: https://www.datadoghq.com/ • Disqus: https://disqus.com/ • Dropbox: https://www.dropbox.com/ • Heroku: https://www.heroku.com/ • Max Levchin: https://www.linkedin.com/in/maxlevchin/ • Okta: https://www.okta.com/ • Omar Johnson: https://www.linkedin.com/in/omarjohnson/ • Oracle: https://www.oracle.com/ • Sentry: https://sentry.io/welcome/ • Satya Nadella: https://www.linkedin.com/in/satyanadella/ • Stripe: https://stripe.com/ • Uber: https://www.uber.com/ • VS Code: https://code.visualstudio.com/ • WindSurf: https://windsurf.com/editor • Y Combinator: https://www.ycombinator.com/ • Yandex: https://yandex.com/ Timestamps (4:01) Learning to code through gaming (6:31) Dropping out of high school (9:47) Building infrastructure at Disqus (10:20) “Software is not that hard” (12:45) Early interest in open source (15:45) The birth of Sentry (23:37) Two common founder mistakes (27:13) David’s unwavering focus (28:17) Sentry’s journey to venture backing (36:43) Finding conviction in decisions (41:11) How Sentry found PMF (46:34) More confidence, less ego (48:08) Is sales valuable? (51:31) David’s personal philosophy (1:01:17) Money is not the hardest problem (1:06:27) Marketing won’t fix a bad product (1:10:34) What makes Sentry’s market unique (1:16:24) “You’re gonna mess up” (1:22:08) Why brand will always matter (1:30:51) Eliminating all competition