Tropical MBA: Entrepreneurship & Founder Lifestyle

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 (https://bentonow.com/tmba) “The Prison of Financial Mediocrity” Full Article (https://x.com/systematicls/status/2004900241745883205) The End of Jobs by Taylor Pearson (Dynamite Circle member!) (https://www.amazon.com/End-Jobs-Meaning-9-5-ebook/dp/B010L8SYRG) The Psychology of Money by Morgan Housel (https://www.amazon.com/dp/0857197681/) Same As Ever by Morgan Housel (https://www.amazon.com/Same-Ever-Guide-Never-Changes/dp/0593332709) The Courage to Be Disliked by Ichiro Kishimi et al (https://www.amazon.com/The-Courage-to-Be-Disliked-audiobook/dp/B07BRPW98K/) Meet lifestyle founders inside Dynamite Circle (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders in DC BLACK (https://dynamitecircle.com/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 (https://tropicalmba.com/episodes/how-to-build-systems) “The World Is Ending.” These 5 Businesses Are Still Making Millions (https://tropicalmba.com/episodes/the-world-is-ending-9jp7t) Why $120K From Your Biz Beats $150K at a Job (https://tropicalmba.com/episodes/balancing-wealth-freedom-mindset)

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 (https://www.youtube.com/@LaylaPomper) EOS Business System (https://www.eosworldwide.com/) Meet other location-independent founders like Layla inside Dynamite Circle (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders in DC BLACK (https://dynamitecircle.com/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 (https://tropicalmba.com/episodes/numbers-gone-wild-hidden-cost) Financial Traps, Profit Truths, and What’s Next at TMBA (https://tropicalmba.com/episodes/financial-traps-profit-truths)

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 (https://www.amazon.com/Age-Disclosure-Dan-Farah/dp/B0FMF29BBJ) Daniel Salzner: Goldman-Sachs to $40K MRR AI Agency (https://www.linkedin.com/posts/danielsalzner_i-quit-my-job-10-weeks-ago-today-i-bootstrapped-activity-7402723101932670976-rcGS/) Never Enough: From Barista to Billionaire by Andrew Wilkinson (https://www.amazon.com/Never-Enough-Billionaire-Andrew-Wilkinson/dp/1637744765) Meet location-independent founders inside Dynamite Circle (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders in DC BLACK (https://dynamitecircle.com/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 (https://tropicalmba.com/episodes/2026-business-plan) [FREE Resource] TMBA 539: Weathering the Storm (https://tropicalmba.com/episodes/entrepreneurs-survive-economic-downturn) TMBA 546: Adjusting to the 'New Normal' (https://tropicalmba.com/episodes/jim-huffman-new-normal)

What if 90 days from now, your business was sharper, more focused, and positioned for real growth? This simple but powerful 10-question framework is designed to help you identify your biggest challenge, clarify your team’s focus, and uncover new opportunities to stand out in your market. LINKS 90 Day Business Clarity Worksheet (https://docs.google.com/document/d/1a_rGQy83JhYfmcbWhGWZredl43Ds-EAd-1gh1ulAYlg/edit?tab=t.0) Meet location-independent founders inside Dynamite Circle (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders in DC BLACK (https://dynamitecircle.com/dc-black) CHAPTERS (00:03:29) Biggest challenge and next steps (00:06:33) Focus (00:08:24) Understand your customer (00:12:45) Positioning (00:15:55) Innovation and unique advantages (00:21:15) Network (00:22:57) Business model (00:25:06) Team (00:26:38) Cadence & leadership (00:28:34) Bonus 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 (https://tropicalmba.com/episodes/2026-business-plan) [FREE Resource] Don’t Write Another Landing Page Without This Framework (https://tropicalmba.com/episodes/2026-email-funnels-playbook) [2026 Email Funnels Playbook] These 7+ Figure Founders Refused the “Normal” Path to Wealth (https://tropicalmba.com/episodes/7-figure-founders-refused-normal-path)

We’re back from a week of hanging out with rockstars in NYC. Not just figurative rockstars in the form of 25 DC BLACK members and Scott Heiferman of Meetup.com, but also literal rockstar Keith Murray of We Are Scientists. From “friendly” acquisitions to hiring frameworks and thoughts on leadership, this is what’s top of mind for 7 and 8-figure location independent founders going into 2026. LINKS Meet location-independent founders inside Dynamite Circle (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders in DC BLACK (https://dynamitecircle.com/dc-black) Leader’s Intent Framework (https://verticalperformance.us/develop-a-leaders-intent-to-transform-your-team/) Buy Back Your Time by Dan Martell (https://www.buybackyourtime.com/) TMBA 528: The Brenwall Code (https://tropicalmba.com/episodes/markbrenwall2) CHAPTERS (00:05:22) 7-Figures and Location Flexibility (00:09:25) The Rise of “Friendly” Business Acquisitions (00:14:12) What the Hell is Leadership? (00:18:45) Buying Back Your Time with AI & Hiring (00:22:40) Insights from Meetup.com’s Scott Heiferman (00:28:10) Annual Planning: Working Backwards From the Goal (00:31:25) The Crossover Between Artist and Entrepreneur (00:39:46) Overcoming Challenges Through Innovation (00:42:47) Rebranding “Asking for Help” 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: Don’t Write Another Landing Page Without This Framework (https://tropicalmba.com/episodes/2026-email-funnels-playbook) [2026 Email Funnels Playbook] 6-Figure Sales Expert Calls You Out (https://tropicalmba.com/episodes/dont-keep-doing-this-2026) [Don’t Keep Doing This in 2026] Your 2026 Business Plan in 36 Minutes (https://tropicalmba.com/episodes/2026-business-plan) [FREE Resource]