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:

• DC Accelerator
• DC Black
• Dave Ramsey Solutions

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?

Dan flies solo this week in a 3-part episode where he circles back to a few hot topics that caught some listener’s attention over the last few months.

Back in May, Dan shared insights from a book he read called the 5 Types of People Who Will Ruin Your Life. Today he’s sharing a recent story where this came into play.

He also shares lessons from the best business book he’s read in the past 6 months (of which he reads about 3 each week). And last but not least, he reaches into the mailbag to share a story from a listener about their Mexican Fisherman Moment.

Dan & Ian’s Stuff:

The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show Notes:

(00:00:00) Intro
(00:01:44) Too old for basketball
(00:04:33) Personality disorders
(00:11:07) Leadership
(00:24:30) Mexican Fisherman

Links:

• DC Events
• DC Black
• Language Mentoring
• Clockwork by Mike Michalowicz
• The Checklist Manifesto
• Scorecards
• Traction

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

Additional episodes you might enjoy:

TMBA 688: Mailbag: What Can Scorecards Do For You? And Equity Split Dilemmas
TMBA 695: The Money Theory of Location And Why Employee Scorecards Are So Helpful
TMBA 707: Deceptively simple ways to have a better business
TMBA 702: Millions for Podcasts and Jay Clouse on Memberships
TMBA 689: Re-visiting Our Conversation with Seth Godin

In this episode, Ian and Dan discuss the concept of doing things that don't scale, inspired by Paul Graham's influential article 'Do Things That Don't Scale.' They explore the idea of taking risks and gambling in entrepreneurship, and how it relates to increasing one's locus of control. The conversation covers various strategies for founders, including recruiting users manually, building something fragile, delighting users, focusing on experience, and niche marketing. In this conversation, Ian and Dan discuss Paul Graham's article 'Do Things That Don't Scale' and explore the principal themes and takeaways. They cover topics such as the idea of scaling, fabricating products yourself, consulting and acting as an anchor client, going manual and doing unscalable laborious tasks, the illusion of big launches and partnerships, vectors vs. scalars (ideas and execution), and the temptation to gamble and the importance of locus of control.

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 Waking Up Early
● (00:01:58) The Concept of Taking Risks and Gambling
● (00:03:52) Introduction to Paul Graham and Y Combinator
● (00:05:37) The Importance of Doing Things That Don't Scale
● (00:10:00) Recruiting Users Manually
● (00:12:48) Building Something Fragile
● (00:20:48) Niche Marketing
● (00:23:02) The Facebook and the Idea of Scaling
● (00:24:53) Consulting and Acting as an Anchor Client
● (00:27:17) Going Manual and Doing Unscalable Laborious Tasks
● (00:30:08) The Illusion of Big Launches and Partnerships
● (00:34:54) Vectors vs. Scalars: Ideas and Execution
● (00:38:36) The Temptation to Gamble and the Importance of Locus of Control

Links:

• Paul Graham’s Article “Do Things That Don’t Scale”
• Lao Tzu - Philosophy

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:

Three Phases to 1 Million in Revenue

Quiet Crypto, The Demand Question, and Difficult Decisions ft. Jordan Gal

“3 Million in Revenue is a Death Zone" - Financial Strategy with Greg Crabtree

Dan and Ian challenge listeners to answer five questions about your business that will help you evaluate how healthy your operations are.

They cover everything from doubling down on what’s working best to effective resource allocation and working “on” your business instead of “in” your business.

You’ll also be challenged to ask yourself: “What would a skilled entrepreneur do with my business?”

Take out your pens and notepad (very important), and consider this episode a free coaching session and a little taste of DC Accelerator.

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
● (00:00:33) Working on Your Business vs. in Your Business
● (00:02:32) Evaluating Your Team's Value Creation
● (00:17:17) Doubling Down on What's Working Best
● (00:19:35) Maximizing Return on Investment
● (00:21:53) Effective Resource Allocation
● (00:27:22) Unprecedented Growth: What Would a Skilled Entrepreneur Do?
● (00:36:24) Evaluating and Refining Your Business with Diagnostic Questions

Links:

• 30 Business Diagnostic Questions
• Kaco Gel Pens
• Artist Sketchbook
• Simple Numbers by Greg Crabtree

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 Million Dollar Service Business Playbook

Run Any Business with Just Two Simple Things

Mastering Consistency with Adam Gilbert

This week, Dan continues delving into the world of coaching with a story about one company that provides highly paid professionals with a low-stress way to earn a living in the sunset phase of their careers.

Dan also interviews Sarah Weaver, a real estate investor and entrepreneur, who has achieved an impressive monthly cash flow of over $10,000 from her real estate portfolio in under five years.

Join us to glean insights from Sarah's journey, as she shares strategies for cash-flowing retirement through smart real estate investments. Sarah talks about how she bought 19 properties, the six metrics she evaluates before investing in a specific city, building a brand around her experience, and more.

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

Show notes:
(00:00:56) Intro
(00:01:14) The DC Black event is happening now
(00:01:44) A new Mexico event
(00:02:30) Loom use cases for async companies
(00:07:13) Ways to generate cash flow
(00:10:15) The steps to 10K+ cash flow per month from rental properties
(00:11:59) Cash flow investing vs appreciation investing
(00:14:17) What metrics to look at before you invest in property
(00:25:30) Don’t meet your heroes, get paid by them
(00:28:43) House hacking from abroad
(00:29:38) Building a brand around your personal experience
(00:37:49) How to skip right past imposter syndrome
(00:39:44) Mistakes people often make in real estate investing
(00:41:53) The no-brainer bucket list experience you should go on

Links:

- Dcbkk recap
- The Upwork Hustle w/ Sam Hill
- CEO Coaching International
- www.sarahdweaver.com
- 30 Day Stay. Use SARAH for 10% off.

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

Additional episodes you might enjoy:

What is the Michael Jordan of Business Models?

Dissecting the American Dream & Business Lessons from the Elon Musk Bio

Mailbag: Hang-ups, Power-ups, and Cheat Codes for Entrepreneurs