In Depth

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


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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
    • Beats by Dre
    • Cursor
    • Dan Levine
    • Datadog
    • Disqus
    • Dropbox
    • Heroku
    • Max Levchin
    • Okta
    • Omar Johnson
    • Oracle
    • Sentry
    • Satya Nadella
    • Stripe
    • Uber
    • VS Code
    • WindSurf
    • Y Combinator
    • Yandex

    • Where to find David:

      • LinkedIn
      • Twitter/X

      • Where to find Brett:

        • LinkedIn
        • Twitter/X
        • Where to find First Round Capital:

          • Website
          • First Round Review
          • Twitter/X
          • YouTube

          • 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

            ...more
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