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?

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:

• Andrew Jacoby - Linkedin
• Nick Huber Twitter
• firstfishermenmedia.com/

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 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

Is it possible to bootstrap a high-level business if you’re broke? Listen to Dan & Ian’s take on what kinds of businesses are best to start when you’re starting with basically nothing.

Also, what the hell does a visionary do? Dan suggests that the best visionaries have integrator tendencies.

They’ll consider how Kevin Kelly’s “100 True Fans” can lead to sustainable revenue through a concept called “The Death of the Follower”.

Lastly, Dan pitches a business idea that requires zero startup cost, 3 days a week of effort, and could easily net you $250K.

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
● (00:00:39) Introduction and companies over title’ing
● (00:04:00) Starting a Bootstrap Business When You're Broke
● (00:08:29) The Role of Visionaries in Company Success
● (00:14:55) The Death of the Follower & Engaging with Social Media Algorithms
● (00:19:54) The Future of Search: AI and Personalization

Links:

• Nick Huber Twitter
• Kevin Kelley - Article - A Thousand True Fans
• The Death of the Follower

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:

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

Do Things That Don’t Scale

Three Phases to 1 Million in Revenue

The hard part shouldn’t be how to implement an OS in your organization. The hard part is answering the question: Are the right people in the right roles at your company?

In this episode, Dan and Ian share their own OS that’s extremely simple. It’s called GPS. They’ll explain how GPS helps you put a plan in place to meet your goals, and deliver on that plan. That’s it.

Also, hiring for specific tasks, the impact of remote work on hiring, and more.

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
● (00:00:41) Introduction and 'Meaty Shorts' Format
● (00:06:48) Hiring for Specific Tasks in a Business
● (00:15:55) Minimum Viable EOS (GPS) Implementation
● (00:16:27) Implementing the EOS System: The GPS Framework
● (00:18:54) Using Scorecards for Clarity and Accountability
● (00:25:06) The Importance of Regular Check-ins and Standing Meetings

Links:

• Dan Martell - Who to Hire Next
• The EOS Business Model
• Scorecard template (G doc)

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:

Do Things That Don’t Scale

Three Phases to 1 Million in Revenue

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

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 discuss the different phases of bootstrapping a business and the common challenges that arise at each stage. They walk through three phases: Zero to $250k “Mindset”; $250k to 1 million "We're seeking a reliable/repeatable source of new customers"; and $1 million + "We need to hire, fire, improve/change team members more effectively”. They explore everything from adjusting the offer to the marketplace and developing a strong customer base to making a rule that the founder should be responsible for growth up to $5M.

They also explore the crucial role that team composition plays in the professionalization of the company. Finally, they discuss the decision between maximizing profitability and scaling the business.

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

● (00:00:43) Introduction and Era Change
● (00:04:28) Mindset for Early Stage Bootstrapping
● (00:08:35) Running a Shit Ton of Experiments
● (00:19:34) Customer Development and Adjusting the Offer
● (00:23:37) Founder's Responsibility for Growth
● (00:24:28) Founder's Role in Growth Until $5 Million
● (00:25:29) Following Strategies That Work for the Majority
● (00:26:41) Celebrating the Achievement of $1 Million in Revenue
● (00:29:18) Transitioning from $1 Million to $5 Million
● (00:34:07) The Importance of Team Composition
● (00:34:22) Shifting Focus to Managing a Team
● (00:39:19) Maximizing Profitability vs. Scaling

Links:

• Simple Numbers by Greg Crabtree
• Exploitative Play in Live Poker

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:

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

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

A Podcast About Shiny Object Syndrome

Dan talks to Jordan Gal, founder of Rally and co-host of the Bootsrapped Web podcast about challenges in the ecommerce space, product-market fit and demand, partnerships and veto power, the quietness of crypto, risking other people’s money, and more…

There’s one thing that founders tend to really struggle with when it comes to growing their business and that’s getting the right team in place. Listen as Jordan shows Dan how and why he fires unfit team members.

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

Chapters

• (00:04:22) News Update
• (00:05:58) From Player to Coach
• (00:06:50) Jack Welch
• (00:12:10) Bootstrapping vs Raising Money
• (00:15:52) Product-Market Fit and Adjustments
• (00:18:57) Partnerships and Veto Power
• (00:20:42) Deciding When to Pivot
• (00:36:27) Firing and Personnel Decisions
• (00:43:30) The Quietness of Crypto
• (00:48:05) Challenges in E-commerce
• (00:57:30) Impact of Having a Family

Links:

• Bootsrapped Web podcast
• Jordan on Twitter
• Rally
• Winning

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:

A Shopify Software Business Success Story (Jordan Gal)

How Transparent Should You Be? Thoughts on Queen Bee Roles & a Ticket Giveaway

A Podcast About Shiny Object Syndrome

Dan & Ian talk to John Doherty, the founder of Editor Ninja, former owner of Credo, and cohost of the Working Sessions podcast about three major trends he’s seeing in the agency space that could impact your strategy and profitability for the year and beyond.

John talks about the challenges of running a full-service agency, a shift towards specialization in productized services, the need for outsourced strategic layers, focusing on profitability, and more.

Stick around for the guys to reveal six productized-service business ideas.

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

Chapters

• (00:02:04) News with Dan & Ian
• (00:05:20) Introducing John Doherty
• (00:06:46) Starting Credo and EditorNinja
• (00:09:30) Trends in the Agency Space
• (00:11:27) Building a Strategic Program
• (00:28:10) Focus on Profitability
• (00:30:40) Importance of Work Quality
• (00:31:55) Categories for Business Opportunities
• (00:32:42) Software Quality Assurance as a Service
• (00:35:57) TikTok Titan: Leveraging TikTok for Business
• (00:38:54) SAAAS: Systems Automation as a Service
• (00:40:28) Managed VA Service for Social Media
• (00:43:57) Fractional Business Strategist
• (00:45:23) Financial Dashboard as a Service
• (00:50:44) Workbooks for Business Metrics

Links:

• Find John on Twitter
• EditorNinja

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

Additional episodes you might enjoy:

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

How Transparent Should You Be? Thoughts on Queen Bee Roles & a Ticket Giveaway

A Podcast About Shiny Object Syndrome

Transitioning through the death zone requires careful execution and a focus on profitability. The $3 million dollar mark is a critical milestone for businesses, and many struggle to push through it.

In this episode, Dan talks to Greg Crabtree, author of Simple Numbers, Straight Talk, Big Profits! about how founders can push through the death zone (otherwise known as the messy middle) and grow their profit far beyond that $3M mark.

Some of the common mistakes made by founders include not understanding profit truth, not investing in finance and accounting, and not effectively managing labor efficiency.

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

Chapters

• (00:00:39) Introduction and the Death Zone
• (00:05:26) The Impact of Paying a Market-Based Wage
• (00:06:53) Behavioral Economics and Profit Truth
• (00:10:34) The Definition of a Fully Capitalized Business
• (00:12:39) Transitioning through the Death Zone
• (00:13:16) The Three Steps to Business Success
• (00:15:04) Remaining Profitable in the Death Zone
• (00:15:50) Different Capital Profiles and Cashflow
• (00:16:53) The Emotional Challenge of Spending in the Death Zone
• (00:19:52) The Executional Problem of Growth
• (00:20:27) Getting Through the Black Hole
• (00:21:51) The $3 Million Mark
• (00:23:15) The Worth of Going Through the Zone
• (00:26:22) Managing a Marketing Agency Past $5 Million
• (00:31:16) Common Mistakes Made by Founders
• (00:33:25) Understanding Profit Truth
• (00:40:23) Investing in Finance and Accounting

Links:

- Apply to win a free ticket to DC Mexico!

• Simple Numbers, Straight Talk. Big Profits!

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

Additional episodes you might enjoy:

How Transparent Should You Be? Thoughts on Queen Bee Roles & a Ticket Giveaway

A Podcast About Shiny Object Syndrome

Spotting Taboo Business Ideas Through the Overton Window

This week Dan & Ian share a few thought experiments you can do to improve your business and reach your next breakthrough.

They cover the value of a writing-first culture, the Queen Bee Role & how transparent should you be with your team?

Plus, a ticket giveaway to one qualified founder.

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

• (00:00:41) Intro
• (00:01:33) Business-changing events for founders
• (00:10:54) Writing is more important than you think
• (00:14:57) Writing culture vs meeting culture
• (00:20:49) The Queen Bee Role exercise
• (00:32:37) Thoughts about sharing revenue with team members

Links:

• Apply to win a free ticket to DC Mexico!
• Clockwork by Mike Michalowicz

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

Additional episodes you might enjoy:

The Anti-Agency Agency + High ROI Customer Acquisition

A Podcast About Shiny Object Syndrome

Spotting Taboo Business Ideas Through the Overton Window

Going deeper on shiny object syndrome, Dan & Ian open the mailbag to read responses to last week’s episode. A listener shares his success story with shiny object syndrome, revealing how he pursues his entrepreneurial impulses without growing crazy. The listener emphasizes the value of muscle memory when it comes to going from zero to one successfully.

Dan & Ian will also discuss how to use societal and scene shifts to gain traction on an idea and even build a successful business out of an idea that might seem a little stupid (to everyone else) at the time.

Plus, we’re looking for our next TMBA team member! If you love reading and writing about business topics and think working alongside Dan & Ian might seem like fun (or a little stupid!), let's talk.

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

• (00:00:54) Intro
• (00:01:13) If you love reading and writing about business, come work with us at the TMBA.
• (00:09:17) The two most popular roles that bootstrapped companies are hiring for right now and how much they're paying.
• (00:14:55) How founders get derailed by the Gell-Mann Amnesia Effect
• (00:19:50) Why even your heroes’ businesses are shit shows
• (00:20:33) How one listener channels his shiny object syndrome to grow his million-dollar business
• (00:26:27) What founders often regret about selling their business
• (00:30:30) Identifying societal disruptions can be a way for bootstrappers to be disruptive and successful
• (00:30:42) What Mark Manson, Patt Flynn, and Muhammad Ali have in common
• (00:39:54) Having a strong perspective could be what you’re missing

Links:

Sign up for a DC Black Q&A virtual meeting (open to all)
Join us in Playa del Carmen, Mexico this May
The Anti-Agency Agency + High ROI Customer Acquisition
Working Backwards: Insights, Stories, and Secrets from Inside Amazon
The score takes care of itself (Bill Walsh)
You can have two Big Things, but not three

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

Additional episodes you might enjoy:

Business Basics: Revenue Durability, “Small” Goals, & High-Leverage Meetings

Non-Obvious Ways to Grow Your Business + Favorite Moments of 2023

End-of-Year Brainstorming, Goal-Setting, and a Mexico Meltdown