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
This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal”
Connect with 6-, 7- & 8-figure founders in Mexico City
Hang out exclusively with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs
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
How 1 New Feature Can 10x Your Pricing + 4 More Insights From DCBKK
Lucy Bella Simkins Built a YouTube Channel with 10,000,000 Subscribers
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)
This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal”
This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies”
Connect with 6-, 7- & 8-figure founders in Bangkok and Mexico
Hang out exclusively with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs
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”
The 3 hats of bootstrapping + Insights from DCBKK 2024
From Ex-Special Ops to 6-Figure Performance Coach ft. Itamar Marani
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
Share your thoughts about the podcast (takes 2 mins)
This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal”
This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies”
Connect with 6-, 7- & 8-figure founders in person and online
Hang out exclusively with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs
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
“Scaling on Steroids” with AI Automation ft. Juan Montero
Numbers Gone Wild: The Hidden Cost of Being Data-Driven
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
Contact Juan
Share your thoughts about the podcast (takes 2 mins)
This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal”
This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies”
Connect with 6-, 7- & 8-figure founders in person and online
Hang out exclusively with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs
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
Why Founders Shouldn’t Delegate AI (Barcelona Recap)
How to Get Rich on X With a 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)
This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal”
This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies”
Connect with 6-, 7- & 8-figure founders in person and online
Hang out exclusively with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs
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
How to Instantly Improve Your Lead Pipeline by 20-50%
Growth vs. Optimization — 90% of Growth Comes from 10% of Activities?
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)
This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal”
This week’s sponsor: Smash Digital “Scale your organic traffic with future-proof strategies”
FREE RESOURCE: Personal Financial Dashboard for Bootstrappers
Olly Meaking’s musings on entrepreneurship and crossing 7 figures ARR:
Hang out with us at DCBKK this month
Connect with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs
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
How to Instantly Improve Your Lead Pipeline by 20-50%
Why $120K From Your Biz Beats $150K at a Job
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
Connect with 7+ figure founders and join us in NYC this December
This week’s sponsor: https://spp.co “Your billing, onboarding & projects in one client portal”
Remote First Recruiting: Hire Your Next Remote Team Member in 21 Days or Less
X’s Head of Product’s projections for the algorithm
LindyMan: an example of using a character or persona online
Moving From A Solopreneur Mindset To An Operator Mindset with Leila Hormozi
22 FREE business resources for location-independent entrepreneurs
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
How to Instantly Improve Your Lead Pipeline by 20-50%
Location Is Leverage: How Advanced Digital Nomads Build Faster
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
Connect with 7+ figure founders and join us in NYC this December
This week’s sponsor: https://spp.co “Your billing, onboarding & projects in one client portal”
“Amp It Up” by Frank Slootman
Harvard Business Review: “The Short Life of Online Sales Leads”
MIT Lead Response Management Study
“The 4-Hour Work Week” by Tim Ferriss
Remote First Recruiting: Hire Your Next Remote Team Member in 21 Days or Less
My First Million Podcast
22 FREE business resources for location-independent entrepreneurs
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
Financial Traps, Profit Truths, and What’s Next at TMBA
“Build It Like You’re Gonna Sell It” (Dan’s “Amp It Up” Review)
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
Connect with 7+ figure founders and join us in NYC this December
X’s Head of Product shares how to get rich on X in 6 months
Google’s “Photoshop killer” Nano Banana
Nick Huber’s thoughts on outsourcing to the Philippines in 2025
Dan’s next read
This week’s sponsor: https://spp.co “Your billing, onboarding & projects in one client portal”
22 FREE business resources for location-independent entrepreneurs
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
The Content Flywheel Behind a 7-Figure Education Business ft. Timothy Moser
Health Advice That Goes Against Everything You Know ft. Jay Feldman
The Freedom Line, 7+ Figure Founders, and Extended DCBKK Recap
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
Connect with 7+ figure founders and join us in NYC this December
The episode that could have made us $1.6 million
@levels.io’s investment portfolio (outperforming the S&P 500)
BowTied Bull’s article “Think Twice After You Make It”
This week’s sponsor: spp.co “Your billing, onboarding & projects in one client portal”
22 FREE business resources for location-independent entrepreneurs
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
What is the Michael Jordan of Business Models?
“When is my LTV good enough?” + Founder Mode for Bootstrappers
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”
Alex Hormozi’s $100M book series
Dan’s book “Before the Exit”
“The Wealth Ladder: Proven Strategies for Every Step of Your Financial Life” by Nick Maggiulli
Nick Maggiulli’s interview on the Afford Anything Podcast
22 FREE business resources for location-independent entrepreneurs
Meet the world’s most generous global entrepreneurs inside Dynamite Circle
Connect with 7+ figure founders like Allen inside 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
What is the Michael Jordan of Business Models?
“When is my LTV good enough?” + Founder Mode for Bootstrappers
In this week’s episode, Allen Walton (SpyGuy) shares how he’s using AI to build custom tools with almost zero coding experience, and how founders can turn everyday business spending into first-class flights.
From AI-powered inventory forecasting to unlocking elite travel perks, this episode is packed with practical tips for bootstrapped entrepreneurs ready to work smarter and travel better.
LINKS
This week’s sponsor: spp.co “Your billing, onboarding & projects in one client portal”
Connect with Allen on X
Allen’s ecomm company
“The 4-Hour Work Week” by Tim Ferriss
“StoryBrand” by Donald Miller
22 FREE business resources for location-independent entrepreneurs
Meet the world’s most generous global entrepreneurs inside Dynamite Circle
Connect with 7+ figure founders like Allen inside DC BLACK
CHAPTERS:
00:00:00 Today’s Guest: Allen Walton
00:07:35 How Allen is Using AI for Business & Personal Life
00:09:45 LLM Deep Research for Competitor Analysis & ICP Creation
00:12:58 Vibe Coding Apps with Zero Technical Experience
00:22:32 This Week’s Sponsor: SPP.co
00:23:50 How Airlines Actually Make Their Money
00:26:34 The Competition of Points and Rewards in 2025
00:30:40 The Worst Way to Redeem Points
00:33:13 How to Maximize Points Accumulation
00:35:48 Why Business Owners Should Pay More Attention to Points
00:38:44 ‘Mozi Madness: Alex Hormozi’s Record-Breaking Launch
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:
Top 5 SEO Tactics That Still Work in 2025 with Sean Markey
TMBA 256: Making Sense of Awards Points and Business Class Upgrades w/ Erik Paquet
TMBA 540: Are You Generating Income or Wealth? w/ Nat Eliason
Organic traffic is getting weird… and kinda looks like an alligator’s mouth (you’ll have to listen to the episode to see what we mean).
SEO expert Sean Markey joins Dan to break down 5 strategies still working in 2025: from parasite SEO to aged domains and Reddit "hacks." If you’re trying to cut through the LLM noise, this episode is the ultimate SEO rabbit hole.
LINKS
Sean’s SEO newsletter for CEOs and founders that hate SEO newsletters
Sean’s SEO community
22 FREE business resources for location-independent entrepreneurs
Meet the world’s most generous global entrepreneurs inside Dynamite Circle
Connect with 7+ figure founders inside DC BLACK
Remote First Recruiting: Find your next best remote hire in 21 days
CHAPTERS
(00:00:00) Today’s Guest: Sean Markey
(00:02:53) The State of SEO in 2025
(00:03:49) What SEO Leaders Are Doing (Instead of Panicking)
(00:04:44) How to Own Page 1 Without Ranking
(00:07:25) Buy Your Way Into the SERPs
(00:09:23) The Reddit Mod Hack No One Talks About
(00:12:58) How Small Channels Are Printing 60K MRR
(00:14:46) Ranking in LLMs Without a Prompt Engineer
(00:17:26) The Aged Domain Shortcut That Still Works
(00:20:54) What Is Parasite SEO (And Why It Works)
(00:22:50) The AI Prompt Stack SEO Founders Are Gatekeeping
(00:25:25) Why Local SEO Still Wins in 2025
(00:26:45) Is SEO Even SEO Anymore?
(00:29:36) Why Community > Courses in 2025
(00:33:03) The 1-1-1 Model: Simple, Scalable, Profitable
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 588: Embracing Growth Through Setbacks w/ Sean Markey
How are legit 7- and 8-figure founders leveraging AI in their businesses? Spoiler alert: they’re not just handing it off to their teams.
From cutting high level consultants to redefining metrics and leadership, Dan shares 7 takeaways from our recent DC BLACK event in Barcelona for million-dollar founders.
LINKS:
The 4-Hour Work Week by Tim Ferriss
Growth Levers and How to Find Them by Matt Lerner
22 FREE business resources for location-independent entrepreneurs
Meet the world’s most generous global entrepreneurs inside Dynamite Circle
Connect with 7+ figure founders inside DC BLACK
Remote First Recruiting: Find your next best remote hire in 21 days
CHAPTERS:
Audio:
(00:00:46) AI Is a Founder-Level Problem
(00:01:16) Real AI Use Cases From 7-Figure Founders
(00:05:15) Financial Freedom Starts Earlier Than You Think
(00:07:45) Million-Dollar Nomads Are Rare (And That’s Powerful)
(00:10:38) How to Hire For Less in Latin America (Quick Plug)
(00:11:38) The Rise of the Lifestyle Business CEO
(00:14:39) Why Fringe Curiosity Is a Superpower
(00:16:21) What’s Your North Star Metric?
(00:22:22) The Meta Takeaway: Define Your Constraint
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 Brutal Truth About Business Exits with Rob Walling
The Content Flywheel Behind a 7-Figure Education Business ft. Timothy Moser
Health Advice That Goes Against Everything You Know ft. Jay Feldman
Timothy Moser, founder of LearnCraft Spanish, shares how he scaled a 7-figure education business in today’s fast-changing online landscape. From why SEO is collapsing to the surprising rise of YouTube as a high-converting channel, Timothy breaks down the strategies behind his content flywheel, email list growth, and powerful giveaway launches that turn listeners into paying customers.
Dan and Timothy also discuss what founders really get from in-person Dynamite Circle events, how a 30-person remote team stays aligned, and the realities of carrying entrepreneurial responsibility—even when you “unplug.”
LINKS:
LearnCraft Spanish
Contact Timothy to talk business
“Traction: Get a Grip on Your Business” by Gino Wickman
Meet the world’s most generous global entrepreneurs inside Dynamite Circle
Connect with 7+ figure founders inside DC BLACK
Remote First Recruiting: Find your next best remote hire in 21 days
22 FREE business resources for location-independent entrepreneurs
CHAPTERS:
(0:00:13) Welcome & Today’s Big Question
(00:01:48) Meet Timothy Moser & LearnCraft Spanish
(00:07:38) How DC Events Unlock Growth
(00:12:16) The SEO Collapse in 2025
(00:14:01) YouTube vs Podcasting in 2025: What Actually Works?
(00:17:04) The Flywheel Effect of Great Long-Form Content
(00:21:24) Timothy’s Counter-Culture Giveaway Strategy
(00:29:50) Scaling and Delegating: Challenges for Bootstrapped Founders
(00:36:24) Can Founders Ever Unplug?
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:
Health Expert EXPOSES the "Eat Less, Exercise More" Movement
When Dan started training for an intense cycling season, he needed more energy... without wrecking his health. That led him to Jay Feldman, a health researcher who believes most mainstream advice is dead wrong.
In this episode, Jay explains why “eat less, exercise more” backfires, and what to do instead. You’ll learn how metabolism really works, which foods help or hurt, and how to eat in a way that actually fuels your life.
LINKS:
FREE Energy Balance Food Guide
The Energy Balance Podcast
22 FREE business resources for location-independent entrepreneurs
Meet the world’s most generous global entrepreneurs inside Dynamite Circle
Connect with 7+ figure founders inside DC BLACK
Remote First Recruiting: Find your next best remote hire in 21 days
CHAPTERS:
(00:00:28) Why This Episode Matters
(00:04:17) What Is the Bioenergetic View of Health?
(00:08:02) Why ‘Eat Less, Exercise More’ Doesn’t Work
(00:13:39) The Food Industry’s Role in the Diet Lie
(00:20:15) What Should You Actually Eat?
(00:22:30) Why Gut Health Affects Energy
(00:27:24) Are Seed Oils Destroying Your Cells?
(00:31:01) Why PUFAs May Accelerate Aging
(00:35:52) What a Metabolism-Friendly Day of Eating Looks Like
(00:38:49) How to Eat Like a Baby (and Why That’s Good)
(00:42:59) Where the Research Is Heading
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 is the World's Best Diet?
The True Cost of Burnout, Anxiety, and Entrepreneurial Depression
Talking Smart Drugs
Dan and Ian respond to a series of spicy "unpopular opinions" about entrepreneurship, employment, digital nomadism, and lifestyle design, sourced straight from Reddit.
They weigh in on whether boring businesses really win, if you can get rich working a 9-to-5, and whether meeting locals is overrated when traveling as a nomad.
LINKS:
22 FREE business resources for location-independent entrepreneurs
Meet the world’s most generous global entrepreneurs inside Dynamite Circle
Connect with 7+ figure founders inside DC BLACK
Remote First Recruiting: Find your next best remote hire in 21 days
CHAPTERS:
(00:00:00) Intro
(00:01:08) Unpopular Opinion #1: Boring Businesses Actually Win
(00:05:26) Unpopular Opinion #2: A Job Can Make You Rich
(00:11:22) Unpopular Opinion #3: Strategic Planning Is a Waste
(00:13:49) Unpopular Opinion #4: Meeting Locals is Overrated
(00:17:49) Unpopular Opinion #5: Entrepreneurship Isn’t All Sacrifice
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:
“Lifestyle Business” vs “Real Business”
We’re halfway through 2025! This episode is a raw look at what’s working, what’s not, and the experiments we’re doubling down on.
From running premium events at zero profit to building lean teams with talent from Latin America, we share the trade-offs and results behind every decision. Dan and Ian open the books on DC BLACK and DC Accelerator, plus they uncover how Remote First Recruiting quietly had one of its best quarters yet.
LINKS:
Dan’s Four Bricks presentation
Meet the world’s most generous global entrepreneurs inside Dynamite Circle
Connect with 7+ figure founders inside DC BLACK
Remote First Recruiting: Find your next best remote hire in 21 days
CHAPTERS:
(00:00:42) Can You Break a Plateau Without Spending $200K?
(00:01:45) Why Your Next Growth Phase Starts With You
(00:06:45) What Happened When Our CFO Left
(00:11:27) Why We Finally Launched a Premium Tier
(00:16:01) The Real Results of Our $5K Coaching Program
(00:22:03) Is Our Recruiting Arm About To Have Its Best Quarter Yet?
(00:28:01) We’re Going to Bangkok This October
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:
“It’s easier to 10X than to 2X” + 8 Lessons from CEO Bootcamp
Building ‘Brick by Brick’: Goals, Plans, Scorecards, Cadence
What happens when you’ve optimized everything… and growth still stalls? In this episode, Dan and Ian break down a powerful distinction most founders miss: the difference between optimization (making your business run smoother) and growth (finding and testing new paths to scale). They unpack insights from Growth Levers by Matt Lerner, a framework that helped PayPal and other startups unlock massive growth and why it still applies to bootstrappers today.
You’ll also get a behind-the-scenes look at how Dan and Ian run operations in under 5 hours per week using the “Four Bricks”: financials, a measured plan, individual scorecards, and pulse meetings (aka the Daily Huddle). Plus: why growth experiments often fail, how to avoid optimization creep, and how interviewing your customers using the “Jobs to Be Done” framework can reveal the 10% that leads to 90% of your growth.
LINKS:
“Growth Levers and How to Find Them” by Matt Lerner
“Scaling Up” By Verne Harnish
Daily Huddle Template
Company Scoreboard Template
Individual Scorecard Template
“Jobs to Be Done” Interview Framework
Dan’s Four Bricks presentation
Connect with generous global entrepreneurs
CHAPTERS:
(00:00:13) Intro: Founders, Channels, and What’s Working in 2025
(00:01:40) Growth vs Optimization: The Lens That Changes Everything
(00:09:34) The Four Bricks: How to Run Ops in Under 5 Hours/Week
(00:18:38) Why Most Teams Avoid Growth
(00:20:32) Growth Levers: The 10% That Drives 90% of Growth
(00:28:00) Jobs to Be Done: Why Customers Really Buy
(00:33:26) Growth Sprints: How to Experiment Without Burning Out
(00:36:22) Common Mistakes That Kill Growth Early
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:
“It’s easier to 10X than to 2X” + 8 Lessons from CEO Bootcamp
Building ‘Brick by Brick’: Goals, Plans, Scorecards, Cadence
What marketing strategies are actually working in 2025? Karla Singson shares standout tactics from a DC Mexico meetup she hosted, where 6- and 7-figure founders revealed how they’re landing clients organically through Facebook groups, trade show podcast hacks, and thoughtful LinkedIn comments (no ad spend required).
We also dive into Karla’s own playbook: how she’s built multiple businesses around authenticity, reputation, and smart delegation. She shares tips for handling sales calls, choosing offers that sell themselves, and why relationships (not reach) are her #1 growth lever.
LINKS:
Karla’s Facebook
Karla’s Instagram
Karla’s Business
Dennis Yu’s “Dollar a Day” Strategy
Connect with generous global entrepreneurs
Founders getting together in Bangkok this October for DCBKK 2025
Read Dan’s book “Before the Exit”
Share your story/sponsor the pod
CHAPTERS:
(00:00:13) Intro: Affordable Marketing for Scrappy Founders
(00:01:29) Karla’s Business Portfolio: From Flowers to Facebook Funnels
(00:05:00) Why Founders Struggle to Delegate
(00:10:17) 3 Low-Cost, High-Impact Client Acquisition Channels
(00:12:59) Organic Facebook Marketing Still Works (Here’s Why)
(00:15:34) The 400% Revenue Trade Show Hack
(00:18:29) How to Capture Leads by Commenting on LinkedIn
(00:21:17) Why Most Founders Are Hesitant to Run Ads
(00:22:50) The Rise of Hyper-Authenticity
(00:26:30) Why In-Person Still Matters (But Not for the Reason You Think)
(00:27:25) The '10 Industry Friends' Strategy for Rapid Growth
(00:34:41) Why Karla Keeps a Business Portfolio (Not Just One Focus)
(00:36:30) The “Duh” Test for Business Ideas
(00:38:46) Sales Calls: What Actually Works in 2025
(00:38:54) Building Rapport That Converts (No Cringe Small Talk)
(00:41:23) Refunds, Guarantees, and the Power of Reputation
(00:42:11) Lessons from a Business Partnership Gone Wrong
(00:45:31) Why Golf Is the Best Business School
(00:48:05) Playa del Carmen as a Business Base: Pros and Cons
(00:52:37) Karla’s Love Letter to 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:
Marketing to High-Dollar Clients
$1.5 Million from LinkedIn: Strategies for Building Influence and Consistent Revenue