Andy Holloway is the founder of Holloway, a company that creates comprehensive, practical Guides researched, written, and refined by experts. He founded the company with the mission of “giving people tools to turn their brains on instead of off.”

We dive into the company, but also dive into Andy’s branding fiasco with his first “startup” as a child, how he started a brewery while still underage, a class and professor that changed his life in college, how he got started writing and how a lake can be a great metaphor for life.

We talk about a number of topics including

  • Andy’s writing practice
  • Teaching & modern education system
  • A college professor that inspired him to think differently
  • Unlocking wisdom from books on the internet
  • Grappling with success & status in the modern world
  • How he stays in touch with the people that matter to him

Here is the full quote we mentioned from Kurt Vonnegut:

When a couple has an argument nowadays they may think it s about money or power or sex or how to raise the kids or whatever. What they’re really saying to each other, though without realizing it, is this: “You are not enough people!

Full Quote Here

You can learn more about Andy and Holloway through his thoughtful Good Work Newsletter or go deeper by buying his guides on Venture Capital and other topics.

Some books we mentioned

Just published! The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

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