The Penguin Latte Podcast #2: Cullin McGrath on Building a Community of Writers and the Nuance of Improvement

Today, I’m joined by Cullin McGrath (@Cullin). Cullin McGrath is a writer that any ambitious creative person needs to know. If you’re a fan of Ryan Holiday or James Clear, then you’ll appreciate Cullin’s insights on what it means to live a life of meaning. I recommend starting off with his newest essay, The Danger in Full-Throttle. It’s an intelligent, revealing story about Cullin’s experience with the often overlooked darkness of self-improvement.

Cullin is also building a paid community of writers at Writer’s Bloc, which I’ve had the privilege of beta-testing. It’s transformed my writing in ways I could not have imagined. I’ll post a piece that I’m working on, and within a few hours, I’ll get generous feedback and support from other aspiring writers. If you want your writing to level up (fiction or non-fiction), I highly recommend checking it out.

“You have to operate in life around something that excites you and fills you with purpose.”

Talking Points

  • What was it like at a Tony Robbin’s Seminar? (2:45)
  • How can introverts promote their work online? (7:20)
  • The pitfalls of self-improvement, the balancing act of building and decompressing (9:30)
  • How building things online has always been a part of Cullin’s life (12:30)
  • When does Cullin feel the most at ease when he’s working towards his goals? (13:40)
  • What meaningful work feels like (14:20)
  • Don’t point fingers at people who aren’t entrepreneurial (15:00)
  • What’s the future of newsletters? (17:20)
  • MattressMatt.substack.com (19:00)
  • Doing the books instead of reading all the books (22:00)
  • Can reading fiction improve your non-fiction writing? (24:40)
  • On Ryan Holiday (27:00)
  • How message boards (remember those?) inspired Cullin’s writing (31:00)
  • How has writing for an audience changed Cullin’s thinking? (32:00)
  • Building confidence as a Creator (35:30)
  • Cullin’s transformation through writing (38:00)
  • Balancing entertainment with ambition (40:00)
  • Books that broke us (46:00)
  • Why we don’t follow GaryVee on social (51:00)
  • The benefits of being disagreeable (55:00)
  • The big questions (1:00:00)
  • Will we really be working for ourselves? (1:04:00)
  • The Future of Writer’s Bloc and the problem of scale in paid online communities (1:08:00)
  • Cullin’s message to people who are stuck (1:13:00)
  • Reading Marcus Aurelius in middle school (1:16:00)

Show Notes and Resources

Tony Robbins Seminars

(And here’s a trailer of the documentary about his seminars.)

The incredibly detailed process of writing a book when your name is Ryan Holiday.

The Four-Hour Workweek – The book that broke me.

The Third Door Book – The book that broke Cullin.

GaryVee

Ryan Holiday on the impact of Meditations by Marcus Aurelius

The Tao Te Ching

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