Tropical MBA: Entrepreneurship & Founder Lifestyle

Dan and Ian share 9 pieces of hiring advice that are typically considered “bad,” but can actually work pretty well for smaller bootstrapped teams - and especially lifestyle businesses.

LINKS

Bento will beat your current email bill — up to 70% off or $300 in credits

“Who” by Geoff Smart and Randy Street

Remote First Recruiting: Land your next hire in 21 days or less

Meet lifestyle founders inside Dynamite Circle

Hang out exclusively with 7+ figure founders in DC BLACK

CHAPTERS

(00:03:42) Tip 1: Just Hire a Recruiter

(00:07:11) Tip 2: Work With Friends and Family

(00:10:34) Tip 3: Use AI For Onboarding

(00:12:02) Tip 4: Go Easy on the W2s

(00:14:52) Tip 5: You Don’t Need a Mission-Based Culture

(00:20:16) Tip 6: If You Hire the Wrong Person, Let Them Go

(00:22:54) Tip 7: It Doesn’t Have to Be More Than the Math

(00:25:45) Tip 8: Not Hiring Can Work Out Great

(00:30:30) Tip 9: Polarize Your Managing Style

CONNECT:

[email protected]

[email protected]

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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella.

PLAYLIST:

What We Learned From Running a 7-Figure Remote Business in 2025

The 9-5 is Dead, This is the Socially Acceptable Lottery Ticket

“The World Is Ending.” These 5 Businesses Are Still Making Millions

Dan and Ian take a candid look back at 2025, share highlights and lowlights from the year, and give a sneak peek into what’s next for Dynamite Circle.

LINKS

Bento will beat your current email bill — up to 70% off or $300 in credits

Ramit Sethi’s Money for Couples

Remote First Recruiting: Land your next hire in 21 days or less

Meet lifestyle founders inside Dynamite Circle

Hang out exclusively with 7+ figure founders in DC BLACK

CHAPTERS

(00:01:56) Personal Finance: The First Step to Entrepreneurship

(00:09:02) Why You Need an Annual Theme

(00:13:03) Business Updates

(00:19:45) Professional Empowerment for Your Team Leaders

(00:25:53) Consistency in Delivering a Great Product

(00:30:31) What We’ve Learned from Hosting Executive Coaching

(00:34:36) Under the Hood at Dynamite Circle

(00:41:02) Highlights and Lowlights of 2025

(00:49:03) Our Themes for 2026

CONNECT:

[email protected]

[email protected]

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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella.

PLAYLIST:

How to Actually Build Systems in Your Small Business ft. Layla Pomper

The 9-5 is Dead, This is the Socially Acceptable Lottery Ticket

Your 2026 Business Plan in 36 Minutes [FREE Resource]

Are we actively watching the rise of the degenerate economy? What does it mean for our entrepreneurial behaviors? What does it mean for our portfolios? Does gambling your way to wealth make sense? And what types of trends will emerge and strengthen in 2026?

Smart things look stupid for a while until they look smart. Dan and Jeff share their thoughts on the recent viral X article “The Prison of Financial Mediocrity” and their views on the “socially acceptable” risk of entrepreneurship as an escape from the 9-5.

LINKS

Bento will beat your current email bill — up to 70% off or $300 in credits

“The Prison of Financial Mediocrity” Full Article

The End of Jobs by Taylor Pearson (Dynamite Circle member!)

The Psychology of Money by Morgan Housel

Same As Ever by Morgan Housel

The Courage to Be Disliked by Ichiro Kishimi et al

Meet lifestyle founders inside Dynamite Circle

Hang out exclusively with 7+ figure founders in DC BLACK

CHAPTERS

(00:00:52) The Traditional Path is Closed

(00:06:00) The Era of Long Degeneracy & Success Via Risk

(00:10:49) Opportunity When the Game is Rigged Against You

(00:20:27) The Socially Acceptable Lottery Ticket

(00:25:47) Financial Nihilism and Betting on Change

CONNECT:

[email protected]

[email protected]

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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella.

PLAYLIST:

How to Actually Build Systems in Your Small Business ft. Layla Pomper

“The World Is Ending.” These 5 Businesses Are Still Making Millions

Why $120K From Your Biz Beats $150K at a Job

What if your systems feel broken because you’re running big-company playbooks in a small, bootstrapped business? Layla Pomper, founder of ProcessDriven, joins us to share how small teams actually build systems that work.

We cover what to prioritize before even thinking about SOPs, how to systemize without hiring an integrator, plus the AI & automation tools her audience is quietly using to move faster.

LINKS

Dive into more of Layla’s systems content

EOS Business System

Meet other location-independent founders like Layla inside Dynamite Circle

Hang out exclusively with 7+ figure founders in DC BLACK

CHAPTERS

(00:01:44) Today’s Guest: Layla Pomper

(00:06:18) Manage Your Mistakes

(00:13:47) Radical Simplicity in Your Systems

(00:17:53) People vs Roles

(00:22:26) Defaulting to Delegation

(00:26:59) Asking For Help & Meeting Cadences

(00:31:40) Why EOS Breaks Down For Small Teams

(00:39:31) Stop “Hiring” Software, Build the System First

(00:42:58) New Tools Worth Paying Attention To

(00:47:24) To YouTube, Or Not to YouTube?

CONNECT:

[email protected]

[email protected]

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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella.

PLAYLIST:

[link to Doomsday Business Ideas episode]

Numbers Gone Wild: The Hidden Cost of Being Data-Driven

Financial Traps, Profit Truths, and What’s Next at TMBA

Apple launched the iPod in the wake of the dot-com bubble. Airbnb launched during the 2008 recession and housing crisis. In fact, half of all the Fortune 500 companies were created during a recession or economic crisis.

With the rise of AI, sociopolitical unrest, and the post-COVID landscape, what new ideas and businesses will emerge in 2026?

This week's sponsor is Bento!

Bento will beat your current email bill — up to 70% off or $300 in credits

https://bentonow.com/tmba

LINKS

The Age of Disclosure

Daniel Salzner: Goldman-Sachs to $40K MRR AI Agency

Never Enough: From Barista to Billionaire by Andrew Wilkinson

Meet location-independent founders inside Dynamite Circle

Hang out exclusively with 7+ figure founders in DC BLACK

CHAPTERS

(00:00:13) Change = Opportunity

(00:05:36) Idea #1: Solutions to AI Worry

(00:07:59) Idea #2: Address Digital Degeneracy

(00:12:42) Idea #3: Homesteading and Doomsday Prep

(00:20:34) Idea #4: Religious Revival

(00:23:58) Idea #5: Lifespan Optimization

CONNECT:

[email protected]

[email protected]

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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella.

PLAYLIST:

Your 2026 Business Plan in 36 Minutes [FREE Resource]

TMBA 539: Weathering the Storm

TMBA 546: Adjusting to the 'New Normal'