• How does Alex grow as an entrepreneur over the course of the episodes?
• How does Gimlet Media grow over the course of the episodes?
• What does Alex learn about heading a start up?
• What mistakes does Alex learn over the course of the episodes?
• What qualities of the business and its founders make it possible for Gimlet to secure financing?
• What qualities of the business and its founders make it possible for Gimlet to get off the ground?
• Do you view Gimlet as a successful startup? Why or why not?
• What advantages does Alex have that many media entrepreneurs do not? How does this impact his startup?
• What did you learn about startup culture from the podcast?
• What decisions would you have made differently than Alex?
• Do you agree with the financing decisions the company makes?
• What decisions that Alex made had the most impact on his company?
• What did you learn from the podcast that you could not learn from a traditional textbook on the entrepreneurial textbook?

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