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#39: Alex Lieberman, Cofounder and Executive Chairman of Morning Brew — Mental health for founders, having a framework for decision-making, and deciding when it's time to leave your job to start a company


Alex Lieberman is the Cofounder and Executive Chairman of Morning Brew, a media brand that empowers modern business leaders with need-to-know content that is engaging and timely. Since its founding in 2015, Morning Brew has provided millions of users with the most important news from Wall Street to Silicon Valley.

Alex was someone ahead of the curve, thinking about the future of content delivery when he started Morning Brew from his dorm room. In our conversation, we discuss the importance of mental health for founders, what it was like to sell his company, his decision-making framework, and why he left his corporate job to start a new company.

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Key highlights in the episode

  • Know our guest Alex Lieberman (00:25)
  • How Alex Lieberman started Morning Brew  (01:49)
  • How he met his Cofounder Austin Rief (05:30)
  • The transitioning process from his corporate job at Morgan Stanley to working full-time at Morning Brew (10:03) 
  • The pivotal moment that changed his decision-making framework (17:20)
  • What it was like when Alex sold Morning Brew (23:22)
  • How Alex and Austin navigated the ups and downs in their business (32:23)
  • The transition process from CEO to Executive Chairman of Morning Brew (34:54)
  • The Entrepreneurial Operating System(EOS) (37:04) 
  • Alex Lieberman struggles with mental health (38:45) 
  • His strategies for healing and how he maintains perspective right now (47:43)
  • Exiting tool that he is building to help other founders (51:58)
  • Recommended reading (54:28)
  • Why do Founders experience depression and loss of identity when they transition to Executive Chairman or sell the company?  (1:01:18)
  • His podcasts and video series (01:05:54)
  • What Alex wishes he had known earlier on his journey (01:14:06)
  • His advice for other founders as they embark on their journey to grow into leaders (01:14:40)


Notable Quotes

  • “All I can control are the things that are in my control, and what I can control are the things that I spend time on and that I feel energy around.” (19:52)
  • “Having my actions near the story that I want to be stronger in my life, which is kind of like my inner desires, the things that give me the most joy is a constant tagging pole.” (23:06)
  • “Feeling deeply is such a beautiful thing to experience life fully.” (30:54)
  • “First job of a company is to find product-market fit, second job of a company is to build a company.” (36:25)
  • “Don’t throw all your eggs in a single identity basket.”  (01:02:26)
  • “The only way to start pushing the things that you don’t know that you don’t know into the things that you know that you don’t know and the things that you know you don’t know into the things that you know that you know is by making a lot of mistakes that reveal your blindspots.” (01:11:25)


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