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Ask-Me-Anything with Founder & Chairman Tony Stubblebine

We’re celebrating’s 10-Year Anniversary with a series of AMA conversations.

In this conversation with Kendra Kinnison & Tony Stubblebine, we explore:

  • how the app was born 10 years ago,
  • why the team went all-in on coaching,
  • how Tony used category design to become the CEO of Medium,
  • why he believes in using unreasonable efforts strategically,
  • how companies can use Medium,
  • why coaches could use Medium instead of a blog,
  • why he thinks coaches have extreme credibility,
  • what’s next for Medium,
  • and what’s next for


  • 00:34 The origin story
  • 4:51 How we discovered habit tracking wasn’t enough
  • 6:21 Why habit coaching works
  • 11:48 How Tony recently became the CEO of Medium
  • 17:16 Tony’s recommendations for how coaches can use Medium
  • 20:53 Specializing versus generalizing
  • 27:09 How to use category design
  • 29:42 How to use Medium to increase writing distribution
  • 33:00 Specific writing advice for coaches
  • 35:41 How to differentiate by going beyond reasonable sometimes
  • 39:21 Publishing as a company versus an individual
  • 42:05 Recent updates to the Medium platform
  • 44:35 Tony’s writing framework
  • 49:36 What Tony is most proud of
  • 54:11 What Tony and Kendra are most excited about next