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: Dan@tropicalmba.com Ian@tropicalmba.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, 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: Dan@tropicalmba.com Ian@tropicalmba.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, 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: Dan@tropicalmba.com Ian@tropicalmba.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, 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: Dan@tropicalmba.com Ian@tropicalmba.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, 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: Dan@tropicalmba.com Ian@tropicalmba.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, 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]

With so many ways to make money online, many founders and creators have lost sight of the most powerful one: email marketing. John Ainsworth, founder of Data Driven Marketing, says you’re leaving tons of money on the table if you’re not doing it well. John is back on the pod to share his best tips and tactics on landing pages, upsells, lead magnets, and more. You might want to take some notes for this one! LINKS Rolodex Marketing Resource (https://docs.google.com/document/d/1jRV_ncgCWAMRB7tZZtnO7x0Tn5sE46-tYkwN6paVG3A/edit?tab=t.0) Free Email Marketing Resources (https://datadrivenmarketing.co/resources/) John’s Podcast: The Art of Selling Online Courses (https://www.youtube.com/@john_ainsworth/videos) Meet John and other location-independent founders inside Dynamite Circle (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders (https://dynamitecircle.com/dc-black) Get 2 months of Perspective AI FREE with promo code TMBA (https://getperspective.ai/tmba) Share your thoughts about the podcast (https://getperspective.ai/interview/tmba-feedback) [takes 2 minutes] 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:02:11) Email Marketing: A Must-Have Money Maker (00:11:50) 15 Steps to a High-Converting Landing Page (00:19:18) Do Webinars Still Work in 2026? (00:24:09) What Makes a Great Lead Magnet (00:29:09) The Power of Order Bumps and Upsells (00:36:58) How to Use AI to Improve Your Funnels (00:40:45) How to Make Extra Money with Trip Wires (00:44:37) Rapid-Fire Email Tips for 2026 (00:50:49) How John is Running His 7-Figure Agency CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: Marketing to High-Dollar Clients (https://tropicalmba.com/episodes/marketing-to-high-dollar-clients) 6-Figure Sales Expert Calls You Out (Don’t Keep Doing This in 2026) (https://tropicalmba.com/episodes/dont-keep-doing-this-2026) 8 Simple Steps for Improving Your Sales Funnel (https://tropicalmba.com/episodes/john-ainsworth-sales-funnel)

Sticking rigidly to your sales scripts, hiring and firing sales reps, and positioning yourself as a freelancer instead of the expert: these mistakes will cost you in 2026 if you don’t address them now. 6-figure fractional sales manager, Jeff Pecaro, joins us once again to reveal his best sales insights and call us out on the mistakes we need to leave behind in 2025. Plus, we get into how he and other 6-7 figure businesses inside Dynamite Circle are scaling with just one human and multiple bots. LINKS How to work with Jeff (https://meetwingman.com/) Jeff’s favorite microphone for sales calls (https://www.amazon.com/Shure-MV7X-Podcast-Microphone-Voice-Isolating/dp/B09BZZCGC8/) Get 2 months of Perspective AI FREE with promo code TMBA (https://getperspective.ai/tmba) Share your thoughts about the podcast (https://getperspective.ai/interview/tmba-feedback) [takes 2 minutes] Connect with 6-, 7- & 8-figure founders in Dynamite Circle (https://dynamitecircle.com/dcbkk) Hang out exclusively with 7+ figure founders (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:00:13) Today’s Guest: Jeff Pecaro (00:01:44) The Biggest Challenge Holding Back Your Sales (00:05:00) Start Positioning Yourself as the Expert (00:14:31) Conversion Rate Benchmarks to Aim For (00:18:59) How to Go From “Good Call” to $ in the Bank (00:26:33) Sales Best Practices in 2026 (00:32:24) 2026 Bootstrapper Trends and Predictions CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, 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] $400K in Points & 100% Vibe Coded Shopify Forecasting App with “SpyGuy” Allen Walton (https://tropicalmba.com/episodes/400k-in-points-vibe-coded-app) The Lifestyle Business Playbook (2025 Edition) (https://tropicalmba.com/episodes/lifestyle-business-playbook-2025)

Whether you're a solopreneur or you've got a large team and millions of dollars in revenue, this simple process can help you plan for 2026 in just a few hours. Get ready for your best year in business yet, with clarity and intention. LINKS FREE Resource: Plan Your 2026 With Clarity and Intention (https://docs.google.com/document/d/1gfFSgVgexN8bq1gekgc9oHdRnJsWGA6RMp0876NotcQ/edit?tab=t.0) Ryan Deiss on Scoreboards (https://x.com/ryandeiss/status/1991923587347825150?s=20) Get 2 months of Perspective AI FREE with promo code TMBA (https://getperspective.ai/tmba) Share your thoughts about the podcast (https://getperspective.ai/interview/tmba-feedback) [takes 2 minutes] Connect with 6-, 7- & 8-figure founders (https://dynamitecircle.com/dcbkk) Hang out exclusively with 7+ figure founders (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:00:14) A Reliable Framework for Annual Planning (00:02:13) How to Set the Right Kind of Goal and Plan for the Year (00:08:15) System #1 to Reach Your Goal: Budget (00:13:03) System #2 to Reach Your Goal: Scoreboard (00:18:19) System #3 to Reach Your Goal: Scorecards (00:21:13) System #4 to Reach Your Goal: Cadence (00:24:18) What to Stop Doing & What to Do More Of In 2026 (00:27:59) The Importance of Personal Reflections Before a New Year CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: Growth vs. Optimization — 90% of Growth Comes from 10% of Activities? (https://tropicalmba.com/episodes/growth-vs-optimization) “3 Million in Revenue is a Death Zone" - Financial Strategy with Greg Crabtree (https://tropicalmba.com/episodes/3-million-death-zone) Health Advice That Goes Against Everything You Know ft. Jay Feldman (https://tropicalmba.com/episodes/health-advice-against-everything-you-know)

One of the stickiest things you can do for marketing and retention in your business… host events. We’ve been doing this for our community over the last 12-ish years, and we feel like we’ve finally (sorta) cracked the code. Our Senior Community Manager at Dynamite Circle, Alex Harling, walks us through the guiding principles for hosting a 10/10 event. Apply these to your next sales call, group onboarding session, webinar, or in-person event. LINKS Share your thoughts about the podcast (takes 2 mins) (https://getperspective.ai/interview/tmba-feedback) Get 2 months of Perspective AI FREE with promo code TMBA (https://getperspective.ai/tmba) FREE Checklist: How to Host a Killer Event in 20 Steps (https://docs.google.com/document/d/14e0cea4WGDEPKZEB2Skg7b41KTPZxA9Jy-nwzgRN3q0/edit?usp=sharing) Connect with 6-, 7- & 8-figure founders in Mexico City (https://dynamitecircle.com/) The Art of Gathering by Priya Parker (https://www.priyaparker.com/book-art-of-gathering) Hang out exclusively with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:01:48) The Man Behind Our Last 10/10 Event: Alex Harling (00:03:00) Why Event Principles Are Important For All Businesses (00:05:14) The Art of Gathering (00:10:40) 10 Ways to Make Money With Events (00:13:00) A New Spin on Sponsorship (00:16:50) Case Study: Breakfast Club Austin (00:18:48) The Costco Method (00:21:23) Bonus Ways to Monetize Events (00:25:08) The Biggest Challenge With Hosting Events (00:29:24) External Event Planner vs Your Ops Manager? (00:32:45) Five Principles for Killer Events CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: “How Can I Get Customers For My New Online Sailboat Mechanic Business?” (Case Study in Location Independence) (https://tropicalmba.com/episodes/get-customers-for-online-business) How 1 New Feature Can 10x Your Pricing + 4 More Insights From DCBKK (https://tropicalmba.com/episodes/1-new-feature-10x-pricing) How to Instantly Improve Your Lead Pipeline by 20-50% (https://tropicalmba.com/episodes/improve-your-lead-pipeline)

Considering a pivot to an online business but not sure where to start? A listener wrote in with the same dilemma, and we’re giving our best tips in this week’s episode of the pod. We also discuss a listener who exited for multi-7 figures, a new offer we’re working on for business owners, key learnings from Vercel’s journey to a $9B valuation, and some community news from Dynamite Circle. LINKS We’ve learned a lot from our listeners, and you can learn a lot from your customers. Try Perspective AI. (https://getperspective.ai/tmba) This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) Tweet about $9B Vercel (https://x.com/asmartbear/status/1986158736730419394?s=20) Amp It Up by Frank Slootman (https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115) Connect with 6-, 7- & 8-figure founders in Mexico City (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:01:03) A Listener Who Exited for Multi 7 Figures (00:02:52) How Dan Had a Business Breakthrough in a Tuk-Tuk (00:07:24) DC Accelerator 2.0 Beta (00:11:45) Moving an In-Person Business Online: Listener Case Study (00:23:32) Sponsor Shout-Out: SPP.co (00:24:31) Simple Keys to a $9B Valuation in 5 Years CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: Our Lifestyle Business Non-Negotiables (https://tropicalmba.com/episodes/lifestyle-business-non-negotiables) How 1 New Feature Can 10x Your Pricing + 4 More Insights From DCBKK (https://tropicalmba.com/episodes/1-new-feature-10x-pricing) Lucy Bella Simkins Built a YouTube Channel with 10,000,000 Subscribers (https://tropicalmba.com/episodes/lucy-youtube-channel)

There’s something magical about being at a 5-star hotel in Bangkok to talk business nerdery with 300+ location- and time-flexible founders. Actually, scratch magical and replace that with “not normal.” We’re back from DCBKK, our annual founder pilgrimage to Thailand. Here are 5 insights that made us go “hmmm” all week long. LINKS Share your thoughts about the podcast (takes 2 mins) (https://getperspective.ai/interview/tmba-feedback) This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies” (https://smashdigital.com/) DCBKK 2025 official photos (https://jakesvisuals.pixieset.com/dcbkk2025/) Connect with 6-, 7- & 8-figure founders in Bangkok and Mexico (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:00:44) Back from Bangkok with 5 Insights (00:03:27) Why It’s So Hard to Describe the DC (00:07:18) DCBKK: High-Level Overview (00:09:02) Insight #1: Choose Your Hard (00:12:57) Insight #2: Fractional Hiring (00:17:23) Sponsor Break: Smash Digital & SPP.Co (00:18:57) Insight #3: 10x Pricing with 1 Feature (00:22:31) Insight #4: Simple Event ROI System (00:25:25) Insight #5: Our Messaging Kinda Sucks (00:27:00) Rapid Fire Bonus Insights and Upcoming DC Events CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: Dan’s keynote from DCBKK 2024 “The Four Bricks” (https://www.youtube.com/watch?v=5ZooQo760Ik) The 3 hats of bootstrapping + Insights from DCBKK 2024 (https://tropicalmba.com/episodes/3-hats-bootstrapping-dcbkk) From Ex-Special Ops to 6-Figure Performance Coach ft. Itamar Marani (https://tropicalmba.com/episodes/from-ex-ops-to-performance-coach)

Could your biggest strength also be sabotaging your success? This week Itamar Marani, ex-Special Ops turned mindset coach, reveals how he turned resilience into revenue, scaled from $2K clients to 6-figure programs, and used battlefield lessons to transform founder performance. LINKS Itamar’s Book: Elite Performance: The Israeli Special Ops Mindset System to Win the War Within and Achieve Audacious Goals (https://itamarmarani.com/book/) Share your thoughts about the podcast (takes 2 mins) (https://getperspective.ai/interview/tmba-feedback) This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies” (https://smashdigital.com/) Connect with 6-, 7- & 8-figure founders in person and online (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:00:43) This Week’s Guest: Itamar Marani (00:01:09) Turning Your Niche Expertise into a Business Engine (00:04:43) How a Failed Agency Sparked a Coaching Business (00:09:30) Learning the Coaching Game from the Ground Up (00:11:41) The Truth About Feeling Out of Your Depth (00:13:54) The Evolution from $2K Clients to Six-Figure Engagements (00:19:03) From One-on-One to Scalable Group Coaching (00:27:19) Positioning Yourself When You Feel Unqualified (00:33:27) Building Long-Term Value Beyond the First Program (00:43:03) The ‘Drunk Founder’ Question That Reveals Hidden Truths (00:49:12) How to Sell Coaching Without the Sleaze (00:53:44) The Three Success Killers Holding You Back (00:57:55) Understanding the Performance Traps That Limit Growth CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: TMBA 524: Who Do You Think You Are? ft. Itamar Marani (https://tropicalmba.com/episodes/pseudonyms) “Scaling on Steroids” with AI Automation ft. Juan Montero (https://tropicalmba.com/episodes/scaling-on-steroids-ai-automation) Numbers Gone Wild: The Hidden Cost of Being Data-Driven (https://tropicalmba.com/episodes/numbers-gone-wild-hidden-cost)

Most founders are saving time with AI, but few are actually making money with it. In this episode, Juan Montero of Flowgrama reveals how bootstrappers can build practical AI agents and automations that actually drive revenue. LINKS Juan’s AI Automation Business: Flowgrama (http://flowgrama.com/) Contact Juan (mailto:juanra@flowgrama.com) Share your thoughts about the podcast (takes 2 mins) (https://getperspective.ai/interview/tmba-feedback) This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies” (https://smashdigital.com/) Connect with 6-, 7- & 8-figure founders in person and online (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:00:51) This Week’s Guest: Juan Montero of Flowgrama (00:03:07) Discovering the Power of Automation (00:06:32) How LLMs Changed the Game (00:09:35) The Truth About AI and Job Security (00:14:31) Understanding AI Agents vs. LLMs (00:17:42) APIs: The Backbone of Automation (00:19:29) The Founder’s AI Toolkit (00:24:33) Making Money with Social Automation (00:27:00) How to Avoid Getting Banned on LinkedIn (00:35:38) Using AI Agents for Business Intelligence (00:38:28) Building an HR Agent for Your Team (00:45:44) The Future of CRM Is Custom-Built (00:49:42) Founders Who Are Actually Making Money with AI CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: $400K in Points & 100% Vibe Coded Shopify Forecasting App with “SpyGuy” Allen Walton (https://tropicalmba.com/episodes/400k-in-points-vibe-coded-app) Why Founders Shouldn’t Delegate AI (Barcelona Recap) (https://tropicalmba.com/episodes/why-founders-should-not-delegate-ai) How to Get Rich on X With a Fake Persona (https://tropicalmba.com/episodes/get-rich-fake-persona)

Chasing numbers can actually destroy what made your business great. In this episode, Dan and Ian unpack Goodhart’s Law — the idea that once a measure becomes a target, it stops being useful — and how founders accidentally turn smart goals into bad incentives. Plus, you’ll hear six ways to build healthier systems, lead better, and stop metrics from running your company off the rails. LINKS Share your thoughts about the podcast (takes 2 mins) (https://getperspective.ai/interview/tmba-feedback) This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies” (https://smashdigital.com/) Connect with 6-, 7- & 8-figure founders in person and online (https://dynamitecircle.com/) Hang out exclusively with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:01:16) The Hair-Dye Economy & Durable Businesses (00:03:38) The Problem with Metrics (00:07:44) Fix #1: Revisit Your Brand Promise (00:09:12) Fix #2: Determine a Countervailing Metric (00:12:17) Fix #3: Combine Input and Output Metrics (00:13:12) Fix #4: Refresh Metrics Every 90 Days (00:14:39) Fix #5: Pulse Discipline (00:16:05) Fix #6: The Leadership Lens (00:20:00) The Alt Business School (00:25:42) When a Job Post Becomes a Marketing Hack CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: Wealth Without a 7-Figure Exit: 5 Steps (https://tropicalmba.com/episodes/wealth-without-7-figure-exit) How to Instantly Improve Your Lead Pipeline by 20-50% (https://tropicalmba.com/episodes/improve-your-lead-pipeline) Growth vs. Optimization — 90% of Growth Comes from 10% of Activities? (https://tropicalmba.com/episodes/growth-vs-optimization)

Dan and Ian share 5 money tips for bootstrappers—from prioritizing personal finance and investing to getting in the company of other entrepreneurs. Follow this playbook and you could build wealth without a 7-figure exit (spoiler: only about 5% of businesses achieve this.) Free resource below! LINKS Share your thoughts on the podcast (takes 2 mins) (https://getperspective.ai/interview/tmba-feedback) This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies” (https://smashdigital.com/) FREE RESOURCE: Personal Financial Dashboard for Bootstrappers (https://docs.google.com/spreadsheets/d/1Li7LuETq2k8tfXSC9WrB-xTwtm_YOkxZOFBOT-bk8CM/edit?gid=1717697031#gid=1717697031) Olly Meaking’s musings on entrepreneurship and crossing 7 figures ARR: (https://x.com/helloitsolly/status/1971549899188580447) Hang out with us at DCBKK this month (https://dynamitecircle.com/dcbkk) Connect with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS Audio: (00:00:50) How Dan Got Fired For Having Too Many Ideas (00:02:07) 5 Money Tips for Bootstrappers (00:03:00) Tip #1: Focus on Your Knowledge, Skillset, and Business Model (00:04:14) Case Study: Olly Meakings, Founder of Senja.io (00:07:13) Tip #2: Be Realistic About Your Liquidity Potential (00:11:42) Tip #3: Keep Your Second Bottom Line Sacred (00:16:47) Sponsor Shout-out: Smash Digital (00:17:43) Sponsor Shout-out: SPP.co (00:18:44) Tip #4: Be a Bull About 1 Non-Business Thing (00:23:47) Tip #5: Surround Yourself With Other Entrepreneurs CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: How to Get Rich on X With a Fake Persona (https://tropicalmba.com/episodes/get-rich-fake-persona) How to Instantly Improve Your Lead Pipeline by 20-50% (https://tropicalmba.com/episodes/improve-your-lead-pipeline) Why $120K From Your Biz Beats $150K at a Job (https://tropicalmba.com/episodes/balancing-wealth-freedom-mindset)

This week, Dan and Ian continue the “Get Rich on X” saga with fresh updates, and a reality check. From hiring $4K ghostwriters to creating a new online persona, is X really worth the hype for growing fast—and getting rich—in 2025? LINKS Hang out with us at DCBKK this October (https://dynamitecircle.com/dcbkk) Connect with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) This week’s sponsor: https://spp.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) Remote First Recruiting: Hire Your Next Remote Team Member in 21 Days or Less (https://remotefirstrecruiting.com/) X’s Head of Product’s projections for the algorithm (https://x.com/nikitabier/status/1969057240578748723) LindyMan: an example of using a character or persona online (https://x.com/PaulSkallas) Moving From A Solopreneur Mindset To An Operator Mindset with Leila Hormozi (https://podcasts.apple.com/il/podcast/moving-from-a-solopreneur-mindset-to-an/id1663834553?i=1000681647344) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS Audio: (00:00:34) Business Lessons from the Lemonade Stand (00:02:41) How to Get Rich on X: New Thoughts
 (00:10:16) Be Yourself… Or Create an Online Character? (00:13:49) The Realistic Cost of Hiring a Ghostwriter for X (00:16:46) Sponsor Shout-out: SPP.co
 (00:17:47) Leila Hormozi’s Simple System for Delegation (00:26:12) Location as Leverage: What if the USA Were More Affordable? CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: X’s Head of Product: How to Get Rich in 6 Months (https://tropicalmba.com/episodes/outsourcing-shake-up) How to Instantly Improve Your Lead Pipeline by 20-50% (https://tropicalmba.com/episodes/improve-your-lead-pipeline) Location Is Leverage: How Advanced Digital Nomads Build Faster (https://tropicalmba.com/episodes/location-is-leverage)

Most founders are leaving money on the table without realizing it. Are you one of them? This week, Dan and Ian break down how a tiny shift in how you handle leads can completely change your pipeline. Plus, a counterintuitive approach to networking and why big brands are paying founders to create content. LINKS Hang out with us at DCBKK this October (https://dynamitecircle.com/dcbkk) Connect with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) This week’s sponsor: https://spp.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) “Amp It Up” by Frank Slootman (https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115) Harvard Business Review: “The Short Life of Online Sales Leads” (https://hbr.org/2011/03/the-short-life-of-online-sales-leads) MIT Lead Response Management Study (https://cdn2.hubspot.net/hub/25649/file-13535879-pdf/docs/mit_study.pdf) “The 4-Hour Work Week” by Tim Ferriss (https://fourhourworkweek.com/) Remote First Recruiting: Hire Your Next Remote Team Member in 21 Days or Less (https://remotefirstrecruiting.com/) My First Million Podcast (https://www.mfmpod.com/) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:00:00) Intro (00:01:01) Business Idea: “Lifestyle” Services for 7-Figure Businesses
 (00:08:30) How to Improve Your Lead Pipeline 20-50% Overnight (00:11:50) How Responding Faster to Leads Impacts Your Business (00:16:46) Sponsor Shout-out: SPP.co (00:17:47) Conference A or Conference B? (00:19:38) Business Idea: Partner Podcast with Big Bucks Brand CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: The Outsourcing Shake-Up: LATAM vs. Philippines (https://tropicalmba.com/episodes/outsourcing-shake-up) Financial Traps, Profit Truths, and What’s Next at TMBA (https://tropicalmba.com/episodes/financial-traps-profit-truths) “Build It Like You’re Gonna Sell It” (Dan’s “Amp It Up” Review) (https://tropicalmba.com/episodes/build-it-sell-it)

It’s another mixed bag of business topics on this week’s episode of the pod: X’s Head of Product shares the suspiciously simple playbook to getting rich on the platform, Google’s “Photoshop Killer” is officially on the loose, emerging thoughts on pivoting away from the Philippines for outsourcing remote talent, luxury lifestyle for a fraction of the cost in Thailand, and more. Quick reminder that we’ll be in Bangkok next month with Dynamite Circle for a week of sheer business nerdery. Details in the links below! LINKS Hang out with us at DCBKK in Bangkok this October (https://dynamitecircle.com/dcbkk) Connect with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) X’s Head of Product shares how to get rich on X in 6 months (https://x.com/nikitabier/status/1963498520805007470) Google’s “Photoshop killer” Nano Banana (https://gemini.google/overview/image-generation/) Nick Huber’s thoughts on outsourcing to the Philippines in 2025 (https://x.com/sweatystartup/status/1963588036102348943) Dan’s next read (https://www.amazon.com/100M-Money-Models-Make-Acquisition-com-ebook/dp/B0FMXTZ4MH) This week’s sponsor: https://spp.co “Your billing, onboarding & projects in one client portal” (https://spp.co/) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS Audio: (00:00:00) Intro (00:01:29) How to Get Rich on X in 6 Months (00:04:51) How to Stay Consistent with Content (00:10:14) Google’s “Photoshop Killer”: Nano Banana (00:13:58) PH No Longer a Hotspot for Remote Recruiting?
 (00:18:29) Sponsor Shout-out: SPP.co
 (00:19:47) Luxury Location-Independent Lifestyle in Thailand
 (00:27:22) Hits of the Week: Hormozi, Feldman, DCBKK CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: Why $120K From Your Biz Beats $150K at a Job (https://tropicalmba.com/episodes/balancing-wealth-freedom-mindset) The Content Flywheel Behind a 7-Figure Education Business ft. Timothy Moser (https://tropicalmba.com/episodes/content-flywheel-behind-7-figure-business) Health Advice That Goes Against Everything You Know ft. Jay Feldman (https://tropicalmba.com/episodes/health-advice-against-everything-you-know) The Freedom Line, 7+ Figure Founders, and Extended DCBKK Recap (https://tropicalmba.com/episodes/dcbkk-recap-2023)

Why are so many chasing $10M exits when $3-4M plus a paid-off house might be the real freedom number? Should you be betting big on Bitcoin in 2025, and did we miss out on a massive opportunity 9 years ago? And if you’re “unemployable,” is that a badge of honor... or a red flag? This week, Dan and Ian crack open the reality behind location-independent entrepreneurship: from sipping wine in Europe (and still gaining weight) to navigating whether your side hustle cash flow can really replace that W-2 paycheck. LINKS Join Dynamite Circle and hang out with us in Bangkok in October (https://dynamitecircle.com/dc-black) Connect with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black) The episode that could have made us $1.6 million (https://tropicalmba.com/episodes/bitcoin) @levels.io’s investment portfolio (outperforming the S&P 500) (https://levels.vc) BowTied Bull’s article “Think Twice After You Make It” (https://bowtiedbull.io/p/think-twice-after-you-make-it) This week’s sponsor: spp.co “Your billing, onboarding & projects in one client portal” (http://spp.co) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) CHAPTERS (00:00:00) Intro (00:01:44) What percentage of W-2 Income is Small Biz income worth? (00:13:48) This Week’s Sponsor: SPP.co (00:15:12)  Are Entrepreneurs Truly Unemployable? (00:18:34)  “Financially Cozy” Level of Wealth (00:26:18) Europe for the summer: overrated, underrated, or properly rated? (00:27:26) Company news CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: The Changing Landscape of SEO and the Influence Equation (https://tropicalmba.com/episodes/changing-landscape-seo) What is the Michael Jordan of Business Models? (https://tropicalmba.com/episodes/michael-jordan-business-model) “When is my LTV good enough?” + Founder Mode for Bootstrappers (https://tropicalmba.com/episodes/ltv-good-enough)

If you’ve been living under a rock, you might have missed Alex Hormozi’s record-breaking launch of his latest book $100M Money Models (yep, reps from Guinness World Records were there to verify.) One of the most prominent internet business gurus of our time, Alex’s marketing and launch strategies paint a vivid picture of the power of “the influence equation.” Love him or hate him, his journey is inspiring for all entrepreneurs. Here are 5 takeaways from the launch, specifically for bootstrappers in the trenches. LINKS This week’s sponsor: spp.co “Your billing, onboarding & projects in one client portal” (http://spp.co/) Alex Hormozi’s $100M book series (https://www.acquisition.com/books) Dan’s book “Before the Exit” (https://www.amazon.com/Before-Exit-Thought-Experiments-Entrepreneurs-ebook/dp/B07BN2KD1J) “The Wealth Ladder: Proven Strategies for Every Step of Your Financial Life” by Nick Maggiulli (https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039) Nick Maggiulli’s interview on the Afford Anything Podcast (https://podcasts.apple.com/ph/podcast/nick-maggiulli-the-wealth-ladder-has-six-rungs-and/id1079598542?i=1000719716621) 22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources) Meet the world’s most generous global entrepreneurs inside Dynamite Circle (https://dynamitecircle.com/) Connect with 7+ figure founders like Allen inside DC BLACK (https://dynamitecircle.com/dc-black) CHAPTERS (00:00:00) Intro (00:01:07) $87M in 8 Hours: Hormozi’s Record-Breaking Launch (00:06:05) Takeaway #1: The Power of the Influence Equation (00:11:53) Takeaway #2: Three Types of Media Strategy (00:14:35) This Week’s Sponsor: SPP.co (00:15:53) Takeaway #3: Choose Your Extreme (00:18:40) Takeaway #4: Aggressively Do the Hardest Thing (00:20:06) Takeaway #5: Risk - The Secret to Stratospheric Wealth (00:25:08) Final Thoughts: The Corner Office Test CONNECT: Dan@tropicalmba.com Ian@tropicalmba.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, Justin Tan, Matt Gartland, Ayman Al-Abdullah, Lucy Bella. PLAYLIST: The Changing Landscape of SEO and the Influence Equation (https://tropicalmba.com/episodes/changing-landscape-seo) What is the Michael Jordan of Business Models? (https://tropicalmba.com/episodes/michael-jordan-business-model) “When is my LTV good enough?” + Founder Mode for Bootstrappers (https://tropicalmba.com/episodes/ltv-good-enough)