Tropical MBA: Entrepreneurship & Founder Lifestyle
by Dan Andrews; Ian Schoen
Is this your podcast?Dan Andrews and Ian Schoen are independent podcast creators known for their expertise in entrepreneurship and their ability to connect with a community of founders. Through the Tropical MBA Podcast, they provide insights drawn from their ow…
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Estimated from 8 chart positions in 8 markets.
By chart position
- 🇬🇧GB · Entrepreneurship#1535K to 30K
- 🇧🇷BR · Entrepreneurship#1341K to 10K
- 🇳🇱NL · Entrepreneurship#1671K to 10K
- 🇷🇴RO · Entrepreneurship#730K to 100K
- 🇵🇹PT · Entrepreneurship#106500 to 3K
- Per-Episode Audience
Est. listeners per new episode within ~30 days
12K to 49K🎙 Daily cadence·857 episodes·Last published today - Monthly Reach
Unique listeners across all episodes (30 days)
39K to 162K🇷🇴62%🇬🇧19%🇧🇷6%+5 more - Active Followers
Loyal subscribers who consistently listen
16K to 65K
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* Data sourced directly from platform APIs and aggregated hourly across all major podcast directories.
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From 10 epsHosts
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Recent episodes
#860 How Direct Mail Built a Multi-Million Dollar Business
Jun 11, 2026
Unknown duration
#859 Building a $6.5M Remote Agency in 5 Years — LevelUp Leads
Jun 4, 2026
Unknown duration
#858 Paying for Growth in 2026
May 28, 2026
Unknown duration
#857 AI and the High-Margin Agency: What's Working in 2026
May 21, 2026
Unknown duration
#856 "Trust is the New Currency" — Hot Takes from 200 Founders in Mexico City
May 15, 2026
Unknown duration
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/11/26 | #860 How Direct Mail Built a Multi-Million Dollar Business | Robert Dow buys and sells raw land across Texas and Oklahoma — mostly sight unseen, almost entirely through direct mail. It's a lean operation built on a simple idea: take infrastructure you already have and point it at a new market. In this conversation, we get into his direct mail philosophy (why novelty beats clever copywriting, why your letter should be about the reader and not you), how he thinks about capital structure and tax efficiency, and his take on AI — that it's a powerful tool but not a durable moat. The edge still comes from domain expertise and knowing immediately which option is worth keeping. We also get into personal finance: a self-directed Roth IRA structure that's quietly been one of his best investments, and why most founders shouldn't be doing private deals. Guest: Robert Dow, founder of Remarkable Land Sponsor: [wayfront.com/tmba](wayfront.com/tmba) Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba. Links: Dan Kennedy — The Ultimate Sales Letter Seth Godin — Purple Cow Seth Godin — Linchpin Al Ries & Jack Trout — The 22 Immutable Laws of Marketing Al Ries — Focus John Ruhlin — Giftology Donald Miller — Building a StoryBrand Aaron Ross — Predictable Revenue Chris Voss — Never Split the Difference Robert Cialdini — Influence Alex Hormozi — $100M Offers Jack Carr — The Terminal List Andy Weir — Project Hail Mary Andy Weir — The Martian Cormac McCarthy — The Road Business Resources Upcoming DC Events 🎙️ Tropical MBA is a podcast for entrepreneurs building location-independent businesses. 🔔 Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle. Hang out exclusively with 7+ figure founders in DC BLACK https://dynamitecircle.com/dc-black Chapters: (00:00:42) — Introducing Robert Dow (00:03:32) — Direct mail mechanics and why response rates have dropped (00:04:25) — Dan Kennedy, novelty vs. copywriting, and the green notecard (00:06:13) — Capital structure: how Robert funds deals and turns inventory (00:10:10) — Taxes and cost of capital as the #1 and #2 business costs (00:11:50) — Staffing for lumpy income (00:13:26) — Origin story: from oil and gas to mineral rights to land (00:17:48) — Why established markets still need someone to do the work (00:19:27) — AI as a thinking tool, not a moat (00:22:29) — Personal finance: the self-directed Roth IRA and Checkbook LLC (00:24:32) — Why most founders shouldn't do private deals (00:30:08) — Books, gurus, and using seminal texts as an operating system (00:35:29) — Fiction recommendations and closing thoughts CONNECT: Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses. Email Dan@tropicalmba.com PLAYLIST: AI and the High-Margin Agency: What's Working in 2026 Hard Questions, Easy Business Advanced Personal Finance for Entrepreneurs | — | ||||||
| 6/4/26 | #859 Building a $6.5M Remote Agency in 5 Years — LevelUp Leads | Dan interviews John Karsant, founder of Level Up Leads, a 73-person outsourced SDR agency doing about $6.5M/year revenue, built while living abroad (Argentina, now Barcelona). John shares how he found remote work early via Craigslist, then spun out a list-building service that nearly failed due to one-off sales before pivoting into full appointment setting—eventually cold calling, which raised value, doubled average sale while keeping churn steady, and enabled $15K–$20K/month packages. He explains why radical honesty wins deals, how a strong ops leader and an in-house client dashboard improved transparency, and which metrics matter most (dial-to-connect, meetings booked, show rate, and pipeline movement). In this episode: John discusses hiring ahead of the curve How he compensates reps based on client retention The decline of email outreach John’s inbound engine that drives 80–90% of leads Practical AI uses for role play training, transcript analysis, playbooks, and script generation The value of an experienced CEO coach John’s approach to investing and family life Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba. Links: Level Up Leads More Business Resources Upcoming DC Events 🎙️ Tropical MBA is a podcast for entrepreneurs building location-independent businesses. 🔔 Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle. Hang out exclusively with 7+ figure founders in DC BLACK https://dynamitecircle.com/dc-black Chapters: (00:00:33) Guest Intro Story (00:02:11) Argentina Remote Leap (00:04:24) Barcelona Founder Life (00:05:24) Time Management Abroad (00:07:37) Business Idea Origins (00:08:47) Pivot To Cold Calling (00:12:17) Honest Sales Edge (00:12:48) Ops Systems Dashboard (00:14:27) Metrics And Financials (00:18:12) Retention Based Pay (00:21:44) Outbound Shifts And Inbound (00:24:26) AI Workflows For SDRs (00:28:43) CEO Coaching And Hard Stuff (00:31:32) Personal Finance Investing (00:31:16) Life Outside Work Dadhood (00:38:58) Ideal Clients And Wrap Up CONNECT: Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses. Email Dan@tropicalmba.com PLAYLIST: The $10K Projects You Never Do (AI Just Changed That) How to Build a 6-Figure Digital Business with Claude Code We Got Claude-Pilled | — | ||||||
| 5/28/26 | #858 Paying for Growth in 2026 | Is 2026 the year you finally run paid ads? Something shifted at DC Mexico this year — more founders than ever are seriously considering paid ads as their next acquisition channel. Between AI making creative cheaper to produce and competitive research easier to do, the barriers are lower than they've been. Max Sinclair has run a paid ads agency for eight years. In this episode he breaks down what actually works for founders spending under $30K a year — how to start, what to expect, and whether it's even worth it for your business. Plus: how Max used AI to turn his agency's internal tools into a product, and what that transition looks like in practice. Guest: Max Sinclair — Snowball Creations & SaaS Ads Studio Sponsor: wayfront.com/tmba Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba. Links: Business Resources Upcoming DC Events 🎙️ Tropical MBA is a podcast for entrepreneurs building location-independent businesses. 🔔 Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle. Hang out exclusively with 7+ figure founders in DC BLACK https://dynamitecircle.com/dc-black CHAPTERS: (00:00:00) Welcome and Sponsor (00:00:52) Episode Setup Paid Ads 2026 (00:02:54) Meet Max Sinclair (00:03:13) Why Ads Feel Mental (00:04:21) Beginner Tip Product Fit (00:07:12) Picking Channels S Tier (00:11:52) Intermediate Trust Algorithms (00:15:07) Creative Workflows Win (00:17:34) Advanced Scaling Strategy (00:19:37) Small Budget Remarketing (00:21:15) DIY Learning Roadmap (00:24:22) Wayfront Sponsor Break (00:25:47) Agency Sales Mastery (00:30:19) Agency Pricing Models (00:32:41) Pivot to AI and SaaS (00:38:49) AI Native Team Systems (00:41:26) Biggest Financial Lesson (00:43:57) Wrap Up and Resources CONNECT: Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses. Email Dan@tropicalmba.com PLAYLIST: The $10K Projects You Never Do (AI Just Changed That) How to Build a 6-Figure Digital Business with Claude Code We Got Claude-Pilled | — | ||||||
| 5/21/26 | #857 AI and the High-Margin Agency: What's Working in 2026 | Dan and Ian are joined by Jeff Picaro of meetwingman.com to recap lessons from the DC Mexico event and share five trends for 2026 in bootstrapped, location-independent businesses. In this episode: • Why organic traffic is rebounding and how legacy publishers can compound results via Google, LLMs, and AI repurposing • Why companies with strong SOPs and systems are translating fastest to AI-enabled workflows and higher margins (especially agencies) • How org charts may shift from pyramids to circular, data-centered “hive mind” models with new technical and client-facing roles • Why many founders who started with AI-driven layoffs are rehiring as capacity and demand expand • Why bootstrappers should consider going upmarket, raising contract value, and pursuing bigger customers and deals. Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba. Resources mentioned: Jeff Picaro E-Myth Revisited by Michael Gerber Work the System by Sam Carpenter The 4-Hour Workweek by Tim Ferriss Jack Dorsey's blog post on the circular org chart (published during Block layoffs) Supabase GitHub More Business Resources Upcoming DC Events Tropical MBA is a podcast for entrepreneurs building location-independent businesses. Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle. Hang out exclusively with 7+ figure founders in DC BLACK https://dynamitecircle.com/dc-black CHAPTERS: (00:00:00) Welcome and Guest Intro (00:00:59) Why Events Spark Growth (00:02:45) Trend 1 Organic Returns (00:07:25) Trend 2 Systems Win (00:13:02) Trend 3 Org Charts Shift (00:17:22) Sponsor Wayfront Break (00:18:48) Trend 4 Layoffs to Hiring (00:25:54) Trend 5 Go Upmarket (00:32:23) Wrap Up and Takeaways (00:34:46) Outro and Resources CONNECT: Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses. Email Dan@tropicalmba.com PLAYLIST: The $10K Projects You Never Do (AI Just Changed That) How to Build a 6-Figure Digital Business with Claude Code We Got Claude-Pilled | — | ||||||
| 5/15/26 | #856 "Trust is the New Currency" — Hot Takes from 200 Founders in Mexico City | Dan and Ian just got back from DC Mexico — 4 days in Mexico City with 200 founders, a third of whom run $1M+ businesses. Three ideas worth sitting with: Reading about something is useful. Watching someone implement it is better. Doing it yourself, beside someone else doing it too, is where things get real. Networking gets a bad reputation — and maybe it deserves it. But sharing a real experience with someone who's solving the same problems you are? That's where trust gets built. And trust, right now, might be the most valuable thing a founder can have. In this episode: • Why reading and podcasts only get you so far • What made the DC Mexico AI Build Lab different from any workshop they've attended • The difference between networking and shared experience (and why it matters) • How the attention economy is shifting — and what's replacing it • How to get the most out of any room you're in Thanks to this week's sponsor Wayfront — the AI-ready operating system for productized agencies. One client portal. One team dashboard. All your data, AI-accessible. TMBA listeners get an extra free month on top of the trial at wayfront.com/tmba. Links: More Business Resources Upcoming DC Events Tropical MBA is a podcast for entrepreneurs building location-independent businesses. Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle. Hang out exclusively with 7+ figure founders in DC BLACK https://dynamitecircle.com/dc-black CHAPTERS: (00:00:13) We are back (00:02:40) Mexico City Impressions (00:05:33) DC Mexico Event Breakdown (00:07:14) Community Stats And Culture (00:11:33) Reflection One Get Results (00:17:07) Reflection Two Trust Economy (00:23:05) Our sponsor “Wayfront” (00:24:24) Reflection Three Shared Experience (00:29:09) Quick Hits AI And Acquisitions (00:30:43) Optimism And Next Events (00:32:33) Wrap Up And Sign Off CONNECT: Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses. Email Dan@tropicalmba.com PLAYLIST The $10K Projects You Never Do (AI Just Changed That) How to Build a 6-Figure Digital Business with Claude Code We Got Claude-Pilled | — | ||||||
| 4/23/26 | #855 Hard Questions, Easy Business✨ | business auditfounder challenges+3 | — | Tropical MBADC BLACK+1 | — | business auditfounder lifestyle+3 | — | 26m 30s | |
| 4/16/26 | #854 5 Simple Ways Agencies Are Using AI✨ | AI in agenciesentrepreneurship+3 | Jeff Pecaro | meetwingman.comTropical MBA | — | AIagency founders+3 | Bento | 27m 05s | |
| 4/9/26 | #853 AI Is Useful. Now What?✨ | AI implementationentrepreneurship+3 | — | — | — | AIentrepreneurship+5 | Bento | 28m 54s | |
| 4/2/26 | #852 I Wasted $40K on an AI Agency. Here's What I Built Instead✨ | AI in businesslink building+3 | Aaron Anderson | Claude CodeTropical MBA+1 | — | AI agencylink building+3 | Bento | 26m 07s | |
| 3/26/26 | #851 $1,000,000+ Recurring Revenue — No Employees!✨ | SaaSemail marketing+4 | Jesse Hanley | Tropical MBA | — | recurring revenueno employees+5 | Bento | 50m 40s | |
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| 3/19/26 | #850 We Got Claude-Pilled✨ | AIproductivity+4 | — | Tropical MBA | — | ClaudeAI+4 | Bento | 36m 00s | |
| 3/12/26 | #849 Advanced Personal Finance for Entrepreneurs✨ | personal financeentrepreneurship+3 | David McKeegan | Tropical MBADynamite Circle+1 | — | personal financeentrepreneurs+4 | Bento | 43m 44s | |
| 3/6/26 | #848 The $10K Projects You Never Do (AI Just Changed That)✨ | AI toolsentrepreneurship+3 | Taylor Pearson | Claude Code | — | AIfounders+5 | Bento | 33m 59s | |
| 2/26/26 | #847 From Semi-Retired to 1.3 Million Views on YouTube ft. Richard “RJ” Jalichandra✨ | YouTubeentrepreneurship+3 | Richard “RJ” Jalichandra | Dynamite CircleDC BLACK | — | YouTubeviral+5 | BentoCODE | 44m 05s | |
| 2/19/26 | #846 Can Your Business Beat the S&P 500?✨ | business financeAI in business+3 | — | Tropical MBAS&P 500 | — | businessAI+5 | DC BLACK BentoCODE | 43m 10s | |
| 2/12/26 | #845 How to Build a 6-Figure Digital Business with Claude Code | How long would it take to revamp your entire business? For Elliott Zelinskas: three weeks. Using Claude Code, he rebuilt his 4-year website, generated 100+ SEO pages, automated YouTube creation and publishing, and replaced parts of his tech stack. All without a dev team. Is agentic AI the next evolution of entrepreneurship? LINKS Follow Elliott on X Follow Elliott on Instagram Meet Elliott and other lifestyle founders inside Dynamite Circle Hang out exclusively with 7+ figure founders in DC BLACK Bento will beat your current email bill — up to 70% off or $300 in credits Million Dollar Weekend by Noah Kagan Live Well on Less Than You Think by Fred Brock CHAPTERS (00:00:00) Intro (00:02:39) Meet Elliott & His Business (00:07:05) How Elliott Started Using Claude Code (00:11:16) Upsides and Downsides of Agentic AI (00:15:13) Simple But Powerful Use Cases for Agentic AI (00:22:07) Six Tips for Non-Tech Founders (00:33:18) Security, Risk, and How to Decide What to Build (00:46:42) Digital Nomading and Personal Finance 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: Bad Hiring Advice That Can Actually Work: 9 Tactics for Lifestyle Founders 4 Ways to Start a Business From Scratch in 2026 “Scaling on Steroids” with AI Automation ft. Juan Montero | — | ||||||
| 2/5/26 | #844 4 Ways to Start a Business From Scratch in 2026 | Dan and Ian respond to a listener's email about strategies for going from a 9-5 to full-blown entrepreneurship, and why mindset is far more important long-term than ideas if you want to start a business. LINKS Bento will beat your current email bill — up to 70% off or $300 in credits Million Dollar Weekend by Noah Kagan Dynamite Jobs Meet lifestyle founders inside Dynamite Circle Hang out exclusively with 7+ figure founders in DC BLACK CHAPTERS (00:00:00) Intro and Listener Email (00:05:58) Path 1: “Hold Your Nose and Jump” (00:11:43) Path 2: The Coast Side Hustle (00:14:16) Path 3: Intrapreneurship/Apprenticeship (00:18:14) Path 4: Job Hopping (00:30:05) Product-Market Fit, Passion, and More (00:38:58) Overrated and Underrated Entrepreneurship Tips 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: Bad Hiring Advice That Can Actually Work: 9 Tactics for Lifestyle Founders What We Learned From Running a 7-Figure Remote Business in 2025 The 9-5 is Dead, This is the Socially Acceptable Lottery Ticket | — | ||||||
| 1/29/26 | #843 Bad Hiring Advice That Can Actually Work: 9 Tactics for Lifestyle Founders | 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: 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: 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 | — | ||||||
| 1/22/26 | #842 What We Learned From Running a 7-Figure Remote Business in 2025 | 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: 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 The 9-5 is Dead, This is the Socially Acceptable Lottery Ticket Your 2026 Business Plan in 36 Minutes [FREE Resource] | — | ||||||
| 1/15/26 | #841 The 9-5 is Dead, This is the Socially Acceptable Lottery Ticket | 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: 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 “The World Is Ending.” These 5 Businesses Are Still Making Millions Why $120K From Your Biz Beats $150K at a Job | — | ||||||
| 1/8/26 | #840 How to Actually Build Systems in Your Small Business ft. Layla Pomper | 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: 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 Financial Traps, Profit Truths, and What’s Next at TMBA | — | ||||||
| 1/1/26 | #839 “The World Is Ending.” These 5 Businesses Are Still Making Millions | 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: 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 [FREE Resource] TMBA 539: Weathering the Storm TMBA 546: Adjusting to the 'New Normal' | — | ||||||
| 12/25/25 | #838 Give Me 30 Minutes and I’ll Help You Plan Your Next 90 Days in Business | 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 Meet location-independent founders inside Dynamite Circle Hang out exclusively with 7+ figure founders in 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 [FREE Resource] Don’t Write Another Landing Page Without This Framework [2026 Email Funnels Playbook] These 7+ Figure Founders Refused the “Normal” Path to Wealth | — | ||||||
| 12/18/25 | #837 These 7+ Figure Founders Refused the “Normal” Path to Wealth | 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 Hang out exclusively with 7+ figure founders in DC BLACK Leader’s Intent Framework Buy Back Your Time by Dan Martell TMBA 528: The Brenwall Code 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 [2026 Email Funnels Playbook] 6-Figure Sales Expert Calls You Out [Don’t Keep Doing This in 2026] Your 2026 Business Plan in 36 Minutes [FREE Resource] | — | ||||||
| 12/11/25 | #836 Don’t Write Another Landing Page Without This Framework [2026 Email Funnels Playbook] #836 | 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 Free Email Marketing Resources John’s Podcast: The Art of Selling Online Courses Meet John and other location-independent founders inside Dynamite Circle Hang out exclusively with 7+ figure founders Get 2 months of Perspective AI FREE with promo code TMBA Share your thoughts about the podcast [takes 2 minutes] 22 FREE business resources for location-independent entrepreneurs 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 6-Figure Sales Expert Calls You Out (Don’t Keep Doing This in 2026) 8 Simple Steps for Improving Your Sales Funnel | — | ||||||
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