How Medium Went from Financial Crisis to Focused Innovation

How Medium Went from Financial Crisis to Focused Innovation

From Right Decisions, Right Now by Anaplan

November 20, 2025 · 14 min · Episode 3

About this episode

Tony Stubblebine discusses how he transformed Medium from financial crisis to a successful content platform.

What does it take to turn a company around? Tony Stubblebine, CEO of Medium, shares how he brought Medium from the brink of financial collapse into the innovative, successful content platform it is today. He reveals how he balanced cost-cutting with the need for innovation, the importance of a strong moral compass in leadership, and how to rally a team when confidence is low. This episode is packed with actionable insights for any leader facing a high-stakes financial or morale challenge. (00:00) - Intro (00:51) - Welcome Tony (01:26) - Can you tell us about the company Medium? (02:12) - How did you navigate the first few months as CEO? (04:20) - How did your decision to do a single reduction in force impact the culture? (06:12) - How has your strong moral compass affected your leadership style and what principles guide you through difficult decisions? (08:40) - What financial decisions did you make to course correct Medium’s debt? (10:33) - What is Medium’s “Boost” feature and how was its launch critical to the turnaround? (12:13) - What lesson would you share with other leaders? (13:32) - Thanks & Outro

People in this episode

Guest: Tony Stubblebine

Topics covered

  • company turnaround
  • leadership
  • innovation
  • financial crisis
  • team morale

Keywords

  • Medium
  • Tony Stubblebine
  • leadership
  • innovation
  • financial decisions
  • company culture
  • Boost feature

Mentioned in this episode

Organizations: Medium

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