Today I’m sharing another conversation with Issac Roth about the state of the world as I was seeing it in August 2020 which was admittedly a little grim aided by old memories from OpenShift & Red Hat.

This was a couple months before we knew things would get worse with wildfires in California and Oregon (I couldn’t outside for a solid week or more). In the last published episode (recorded in October 2020), Issac shared his experience of almost losing his house in the California wildfires.

Issac helps clarify what I was seeing and experiencing in the world (not positive at all) and naturally weaves in his past experiences in startups and our time at at Red Hat creating OpenShift. Issac’s optimism is a natural and effective antidote. I love Issac’s calming presence, wisdom, optimism and unique way of seeing the world.

Conversation Highlights

  • Troubling current events and the themes of uncertainty, anxiety and instability
  • Remembering that I have a choice and wanting to use it
  • My own internal conflict about what I’m personally experiencing what I help people with
  • The entrepreneurial journey of holding uncertainty while being super positive and how to manage those doubts
  • Issac’s biggest fears when we were creating OpenShift and how he managed them
  • Building a product based on anticipated usage when real customers are few
  • The constant refinement of priorities, resources and time
  • Reserving time for serendipity
  • Experimenting full fidelity and it’s impact on the data you collect
  • Pushing a boulder up a hill–fulfilling fate or creating fate
  • The ups and downs of startup life
  • How does one find hope in times of uncertainty?
  • The urge to just want things to be okay or know that they will be okay–certainty
  • The distinction between fidelity and integrity
  • Acting in the public or private good
  • Making decisions in a time of very little data without a known framework
  • The apparent absence of truth creates anxiety
  • Taking a “So. What.” perspective to your situation
  • Learn more about Issac Roth


  • Hallon by Christian Bjoerklund
  • Cold Funk by Kevin MacLeod
  • Original photo source

All songs licensed under Creative Commons