TMBA614: The Lifestyle Ladder

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This week’s podcast is inspired by a blog post that we published back in 2014.

That post was titled “What is the Real Cost of the Permanent Travel Lifestyle?” and many of the points we touched on in that article are still being discussed by people in our community today.

One of those people is Jesse Schoberg.

Jesse is the co-founder and CEO of, and he is all too familiar with the challenges of bootstrapping his way up the “Lifestyle Ladder”.

Jesse joins us this week to share his thoughts on location arbitrage, financial freedom, and what he believes the “Lifestyle Ladder” of the permanent traveler looks like in 2021.

See the full transcript below

Listen to this week’s show and learn:

  • What the “Lifestyle Ladder” is and why it’s important. (4:20)
  • How being “broke” can be a good thing. (14:02)
  • What happens when you create a “financial platform”. (21:56)
  • The psychological challenges that come with achieving your dreams. (28:19)
  • What generational wealth really looks like. (41:36)

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
What Is The Real Cost of the Permanent Travel Lifestyle?
Jesse Schoberg
Jason Eckenroth
Empire Flippers
Taylor Pearson
Jesse Lawler
Dreamline – Tim Ferriss

Enjoyed this podcast? Check out these:

TMBA600: Why It’s So Hard to Replicate Success with Derrick Reimer
TMBA603: Returning to Nomadic Life
TMBA613: Is It Possible to Raise a Family as a Digital Nomad?

This week’s sponsor:

Today’s podcast is sponsored by Service Provider Pro.

So many of us want to sell services at scale and to do that successfully, you’re going to need a system for signing up clients all the way through project delivery.

Service Provider Pro gives you that system in a white-labeled client portal for your agency.

With Service Provider Pro, your clients can log in, see all of their orders, download their invoices, and manage their billing all in one place.

It’s also the central source of truth for your team. They can see everything that’s due, collaborate on orders, send reports, and more.

Click here to see how it works, and a big thanks to Service Provider Pro for sponsoring the show.

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Have comments about the show?

Do you have ideas for things you’d like Dan and Ian to discuss on future episodes?

Our producer Jane would love to hear from you at [email protected] or leave us a voice message using the record button below.



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


Dan & Ian


Full Transcript

(Transcript Forthcoming)

(Transcript Forthcoming)