Rich Roll on his "crash course" in entrepreneurship

What happened in this episode?

Rich Roll tells Masters of Scale host Jeff Berman that he started his podcast in late 2012 while living with his wife on an organic farm on Kauai, initially treating it as a low-stakes creative project. He describes how podcasting has become more algorithm-driven, arguing that creators are incentivised to chase contrarianism and drama to generate viral clips, and says he tries to avoid reverse-engineering interviews around shareable outrage.

Roll explains why he is building a small podcast network: he says many established hosts struggle to monetise without either negotiating alone or joining larger networks where they receive “lousy CPMs” and lose control over advertisers. He outlines Voicing Change Media as a joint venture with RXR Sports, and says their sponsorship strategy favours annual or multi-year partnerships and broader “360” arrangements beyond standard ad reads.

The conversation also revisits Roll’s personal history. He recounts years of alcoholism, including two DUIs in quick succession, and says he spent 100 days in a treatment centre at 31. He offers an anecdote he says he has not previously shared on a podcast: receiving a job offer from Akin Gump before entering treatment, then later losing the role after refusing to begin work while still in rehab. Roll links his later endurance training and career shift to sobriety and a long effort to live “in alignment” across work, health and relationships.

What are the key points?

• Roll says he began podcasting in 2012 while living on an organic farm on Kauai, initially unsure he would publish a second episode.
• He argues podcast incentives now favour contrarianism and drama, and says he avoids designing interviews to create viral clips.
• Roll says his network idea came from seeing podcasters struggle to monetise fairly without giving up agency to large networks.
• He names Voicing Change Media as a joint venture with RXR Sports and says partners with sports-management experience shaped the commercial strategy.
• Roll says many brand relationships are multi-year and structured as broader “360” partnerships rather than purely CPM-based ad reads.
• He recounts alcoholism, two DUIs, and a 100-day residential treatment stay at 31; he says sobriety became his primary focus.
• Roll describes losing an Akin Gump job opportunity after refusing to take on casework while still in treatment, in an anecdote he says he has not previously told on a podcast.

Who is speaking?

Named speakers identified in Egleze's source-linked moments from this episode.

• Rich Roll

Which topics are covered?

How is this page sourced?

Programme

Masters of Scale

Published

15 October 2026

Duration

35m

Original episode

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