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:

Where to find David:

LinkedIn
Twitter/X

Where to find Brett:

Where to find First Round Capital:

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

Rock of Love Season 1, Ep. 6 - Becoming Bret