Q: What are some great examples of “at first if you don’t succeed”?

A few:

  1. Twitter started off as Odeo for podcasting–which failed–and most of the investors took their money back, but not all.
  2. Slack started off as Tiny Speck, a gaming company which they had to shut down, but they raised more to productize their chat app, Slack.
  3. Box started off as a photo app for Facebook, but that didn’t work and Facebook productized the space so they became online storage and that became commoditized so they became enterprise content management and are now worth billions.
  4. Algolia started off as a mobile SDK for search but no one would pay for it and they spent all their money and almost didn’t make it but they realized that same code running on servers instead of phones would make for wicked fast search and it is now almost a $100m ARR business.

There’s a lot of this in most start-ups.  Slack said they would also never have salespeople, and now > 50% of their revenue is enterprise.  Even in the e-signature space, Adobe Sign / EchoSign started off as a fax-first service and DocuSign started off as a Windows printer driver.  And both also took a while to go enterprise, now, the vast majority of the revenue is there.

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