Lessons From an 18-Month Trip Around the World on $100 a Day

05/02/24 • 44 min

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Tropical MBA: Entrepreneurship & Founder Lifestyle

This week we had the pleasure of sitting down with Barry O'Brien, a global traveler, as he shares his 18-month journey to 15 countries on just $100 a day or less.

Barry tells us stories about his experience in Vietnam, the most surprisingly underwhelming destination he visited, the most expensive and inexpensive destinations, how he saved, prepared, and what he learned in the end.

He discusses his journey from following Dave Ramsey's steps to discovering the FIRE movement and combining the principles of both to pay off $51,000 of debt, and give him the financial freedom to pursue his dream trip.

He talks about the importance of passive income, his philosophy of focusing on one thing that you can do well, the process of obtaining US citizenship, and the challenges and opportunities it presents.

Dan & Ian’s Stuff:

Our book: Before the Exit
The Newsletter
“The DC”
DC Accelerator
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Chapters:

(00:03:21) Your Ticket to One Million - DC Accelerator
(00:14:59) Exploring Western Europe on a Budget
(00:26:13) Indulging in Peru's Food and Culture
(00:30:15) Managing Travel Costs to Extend the Trip
(00:34:41) Finding Peace and Financial Independence
(00:39:10) The Competitive Landscape of US Citizenship

Links:

Past guests on TMBA include Cal Newport, David Heinemeier Hannson, Seth Godin, Ricardo Semler, Noah Kagan, Rob Walling, Jay Clouse, Einar Vollset, Sam Dogan, Gino Wickam, James Clear, Jodie Cook, Mark Webster, Steph Smith, Taylor Pearson, Tommy Griffith, Justin Tan, Matt Gartland, Travis Jamison, Ayman Al-Abdullah, Tynan, Lucy Bella Simkins, Brian Balfour, Nick Huber, Mike Michalowicz, Greg Crabtree, Jordan Gal

Additional episodes you might enjoy:

The 1 Million Dollar Question

“The Death of the follower” + Make 250k in 3 Days a Week

What is the Most Simple OS for <$5M?

This week we had the pleasure of sitting down with Barry O'Brien, a global traveler, as he shares his 18-month journey to 15 countries on just $100 a day or less.

Dan & Ian’s Stuff:

Our book: Before the Exit
The Newsletter
“The DC”
DC Accelerator
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Chapters:

(00:03:21) Your Ticket to One Million - DC Accelerator
(00:14:59) Exploring Western Europe on a Budget
(00:26:13) Indulging in Peru's Food and Culture
(00:30:15) Managing Travel Costs to Extend the Trip
(00:34:41) Finding Peace and Financial Independence
(00:39:10) The Competitive Landscape of US Citizenship

Links:

Additional episodes you might enjoy:

The 1 Million Dollar Question

“The Death of the follower” + Make 250k in 3 Days a Week

What is the Most Simple OS for <$5M?

Previous Episode

#752 The 1 Million Dollar Question

Crafting your value proposition into an irresistible offer is not an easy task. Andrew Jacoby, entrepreneur and visionary behind Growth Era, a thriving outbound sales company, knows this all too well.
Andrew shares his journey, highlighting the pivotal role of Sales Development Representatives (SDRs) in driving business success.
Discover the power of focusing on what you know best and building a business around recurring services as Andrew unveils the concept of risk reversal and its impact on skyrocketing conversion rates.
From navigating the challenges of educating a market to the transition from CEO to operator, Andrew offers practical strategies for building a robust team and fostering deep community connections amidst a nomadic lifestyle.
Tune in as Andrew delves into the core values of moral fiber and virtue in business, underscoring the true essence of freedom and happiness.
Whether you're an aspiring entrepreneur or seasoned business leader, this episode promises a wealth of wisdom to elevate your sales game.

Dan & Ian’s Stuff:
Our book: Before the Exit
The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Chapters
● (00:00:47) Introduction and Background
● (00:04:19) Growth Era: Company Overview
● (00:04:47) Andrew's Sales Background
● (00:07:29) Challenges and Successes in Outbound Sales
● (00:10:29) Understanding SDRs and Their Role
● (00:12:14) Types of Businesses that Benefit from SDRs
● (00:16:59) Developing an Attractive Offer
● (00:18:15) Growth Era's Business Model
● (00:19:37) Finding Success in Familiar Territory
● (00:23:55) The Importance of Serving People
● (00:25:04) Pricing and Confidence
● (00:25:44) Choosing Between Being an Operator and a CEO
● (00:26:43) Knowing When a Company is Ready for Adults
● (00:29:45) Deep Work and Problem Solving
● (00:32:49) The Nomad Lifestyle
● (00:35:34) The Importance of Community
● (00:38:18) The Pursuit of Virtue and Love
● (00:39:42) The True Meaning of Freedom and Happiness

Links:

Additional episodes you might enjoy:

“The Death of the follower” + Make 250k in 3 Days a Week

What is the Most Simple OS for <$5M?

Do Things That Don’t Scale

Next Episode

#754 - Mastering Consistency with Adam Gilbert

Health and wellness is the ultimate productivity hack, impacting every aspect of life.

Adam Gilbert, founder of My Body Tutor, discovered that consistency is key, and accountability, mindset, and personalized plans help clients stay on track. It’s also what sets his business apart.

My Body Tutor has been generating demand for their service for 17 years, having a flawless reputation, and obsessively focusing on getting clients results.

In this episode Adam shares his strategies for pricing demand, how to handle client churn, and balancing family life with his passion.

Dan & Ian’s Stuff:
Our book: Before the Exit
The Newsletter
“The DC”
DC Accelerator
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Chapters
● (00:06:29) The Impact of Health and Wellness
● (00:12:10) The Importance of Consistency
● (00:16:57) Evolving Pricing Based on Value
● (00:28:39) Recruiting, Training, and Retaining Coaches
● (00:33:10) The Importance of Regular Meetings
● (00:44:17) Caring and Mission-Driven Approach
● (00:45:30) Starting Small in Entrepreneurship

Links: