Tropical MBA: Entrepreneurship & Founder Lifestyle

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)