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

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:   / boxaaron  
• Beats by Dre: https://www.beatsbydre.com/
• Cursor: https://www.cursor.com/
• Dan Levine:   / danielmarklevine  
• Datadog: https://www.datadoghq.com/
• Disqus: https://disqus.com/
• Dropbox: https://www.dropbox.com/
• Heroku: https://www.heroku.com/
• Max Levchin:   / maxlevchin  
• Okta: https://www.okta.com/
• Omar Johnson:   / omarjohnson  
• Oracle: https://www.oracle.com/
• Sentry: https://sentry.io/welcome/
• Satya Nadella:   / 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