The Crazy Ones

Recent Episodes

April 23, 2024

My New Business

Episode 130: On today’s episode, I talk about refinding purpose post-exit and launching my new business storyarb. I share the full details on storyarb with no details spared including, ideation, customer acquisition, early ch...

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April 16, 2024

Why I Stepped Down As CEO

Episode 129: On today’s episode I discuss my decision to step down as CEO of Morning Brew. I chat about going from a Chapter 1 to a Chapter 2 CEO, the emotional journey after stepping down, and climbing out of …

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April 9, 2024

Why We Sold Morning Brew

Episode 128: On today’s episode of Founder’s Journal, I talk through the sale of Morning Brew. I chat about how the opportunity came about, why we said no to previous potential deals, why I thought selling the business was th...

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April 2, 2024

Growing Morning Brew from 0 to 10,000 Subscribers

Episode 127: On this episode of Founder’s Journal, I break down the exact strategies we used to acquire our first 10,000 newsletter subscribers and abstractable growth lessons you can apply to your business. Send us an email ...

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March 29, 2024

Lessons from CMOs, Great Storytelling, Freelance vs. Full-time, Follo…

Episode 126: Today I discuss my biggest takeaways from a Fortune 500 CMO dinner I hosted, choosing between freelancers vs. full-time employees, lessons in storytelling from Shaan Puri, the importance of following your energy,...

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March 27, 2024

Feeling Unskilled, Curing Cancer, and Going All-In on Morning Brew

Episode 125: In today’s episode I chat about being in a content creation slump, making an impact as an entrepreneur, and why you never know if it is the right time to go all in on your business. Send us …

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March 26, 2024

A Little Throwback

Episode 124: Today we’re throwing it back with a true journal style episode. I talk about the joys of finding product market fit, being a default-trusting founder, and understanding extrinsic vs. intrinsic drivers. Send us an...

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March 22, 2024

Always Be Shipping

Episode 123: On this episode, I share a recent blog post by my friend and former colleague, Tyler Denk. Tyler is the co-founder & CEO of beehiiv, a high-growth email newsletter platform. This post outlines Tyler’s philosophy ...

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March 20, 2024

Go Direct

Episode 122: Lulu Meservey is the former Chief Communications Officer of Activision Blizzard and Substack. This episode, I read her recent manifesto, which details the importance of founders crafting their narrative, learning...

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March 18, 2024

The Opportunity Cost of Everything

Episode 121: Writer, Columbia Business School grad, and college athlete Jack Raines' essay, "The Opportunity Cost of Everything," forces readers to ask themselves the only question that really matters: If I was nearing the en...

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