TMBA625: Living Outside Your Comfort Zone

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There is nothing we love more than an entrepreneur who operates outside of convention, and this week’s guest is no exception.

Tynan is a bestselling author and the creator of CruiseSheet, a website that helps travelers find great deals on cruises. He is also a former Pickup Artist or “PUA”, and at one point was a professional gambler.

We’ve been following his terrific blog at for many years, and we’re fascinated by his ability to remain ahead of the curve when it comes to social trends on the internet.

Tynan joins us this week to discuss his history in the controversial Pickup Artist subculture, his unique philosophies on wealth and personal finance, and what it truly means to live outside of your comfort zone.

See the full transcript below

Listen to this week’s show and learn:

  • What it means to be a “Pickup Artist” and what attracted Tynan to that culture. (4:00)
  • Why Tynan chose to sell all of his belongings and travel the world. (19:36)
  • Some common misconceptions about investing. (35:05)
  • The challenges that bloggers face in 2021. (44:44)
  • Advice for people who are trying to get outside of their comfort zone. (53:16)

Mentioned in the episode:

Before the Exit – Our New Book
Partner With Us
The Dynamite Circle
Dynamite Jobs
Dynamite Deals
Tropical MBA on YouTube
Post a Remote Job
Dynamite Jobs – Remote Recruiting Sales Page
Let’s Talk High-Level Podcast Strategy for 1 Hour
Moving Away From Weekly Posting –
The Game by Neil Strauss
Tim Ferriss
The 4-Hour Workweek by Tim Ferriss
Mark Manson
Kevin Kelly
Museum Hack
Derek Sivers

Enjoyed this podcast? Check out these:

TMBA350: A Discussion About The Subtle Art of Not Giving a Fuck
TMBA528: The Brenwall Code
TMBA571: There is Only One Kevin Kelly

This week’s sponsor:

Today’s podcast is sponsored by AppSumo.

AppSumo is the #1 digital marketplace for entrepreneurs.

That’s right, they’re a marketplace and a great way to get your name in front of 1 million-plus entrepreneurs, founders, affiliate marketers, and small businesses. You can sell your software, ebook PDF template library, online course, WP Plugin extension, or even event tickets.

On average digital products on AppSumo earn between $700 – $5000 a month depending on the type of product, and many listeners of this show are already getting results from using their marketplace.

If you want to try them out, head on over to to find out more, and a big thanks to AppSumo for sponsoring the show.

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Have comments about the show?

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST.


Dan & Ian


Full Transcript

(Transcript Forthcoming)

(Transcript Forthcoming)