Tropical MBA: Entrepreneurship & Founder Lifestyle

#850 We Got Claude-Pilled

19 Mar 2026

Contributed by Lukas

After a week of going all-in with Claude and agentic AI, Dan and Ian share what happened when they plugged AI directly into their company workflows. W...

#849 Advanced Personal Finance for Entrepreneurs

12 Mar 2026

Contributed by Lukas

We're often great at making money, terrible at managing it. Multi-exit entrepreneur David McKeegan joins us to discuss personal finance built spe...

#848 The $10K Projects You Never Do (AI Just Changed That)

06 Mar 2026

Contributed by Lukas

Dan talks with Taylor Pearson about a new wave of “agentic AI” tools like Claude Code — and how founders are using them to tackle projects that ...

#847 From Semi-Retired to 1.3 Million Views on YouTube ft. Richard “RJ” Jalichandra

26 Feb 2026

Contributed by Lukas

A semi-retired 6-time CEO accidentally went viral on YouTube, and turned it into a real business case study. Dynamite Circle member and DC BLACK facil...

#846 Can Your Business Beat the S&P 500?

19 Feb 2026

Contributed by Lukas

Dan and Ian hop on the mic to talk about spending money to make more money in your business, getting financial assistance with AI, how to decide where...

#845 How to Build a 6-Figure Digital Business with Claude Code

12 Feb 2026

Contributed by Lukas

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...

4 Ways to Start a Business From Scratch in 2026

05 Feb 2026

Contributed by Lukas

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 import...

#843 Bad Hiring Advice That Can Actually Work: 9 Tactics for Lifestyle Founders

29 Jan 2026

Contributed by Lukas

Dan and Ian share 9 pieces of hiring advice that are typically considered “bad,” but can actually work pretty well for smaller bootstrapped teams ...

#842 What We Learned From Running a 7-Figure Remote Business in 2025

22 Jan 2026

Contributed by Lukas

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 Circl...

#841 The 9-5 is Dead, This is the Socially Acceptable Lottery Ticket

15 Jan 2026

Contributed by Lukas

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...

#840 How to Actually Build Systems in Your Small Business ft. Layla Pomper

08 Jan 2026

Contributed by Lukas

What if your systems feel broken because you’re running big-company playbooks in a small, bootstrapped business? Layla Pomper, founder of ProcessDri...

#839 “The World Is Ending.” These 5 Businesses Are Still Making Millions

01 Jan 2026

Contributed by Lukas

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 Fort...

#838 Give Me 30 Minutes and I’ll Help You Plan Your Next 90 Days in Business

25 Dec 2025

Contributed by Lukas

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 d...

#837 These 7+ Figure Founders Refused the “Normal” Path to Wealth

18 Dec 2025

Contributed by Lukas

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...

Don’t Write Another Landing Page Without This Framework [2026 Email Funnels Playbook] #836

11 Dec 2025

Contributed by Lukas

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 ...

#835 6-Figure Sales Expert Calls You Out [Don’t Keep Doing This in 2026]

04 Dec 2025

Contributed by Lukas

Sticking rigidly to your sales scripts, hiring and firing sales reps, and positioning yourself as a freelancer instead of the expert: these mistakes w...

#834 Your 2026 Business Plan in 36 Minutes [FREE Resource]

27 Nov 2025

Contributed by Lukas

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 f...

#833 55 People Gave Our Last Event a 10/10. Here’s How We Did It [Free Checklist]

20 Nov 2025

Contributed by Lukas

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...

#832 “How Can I Get Customers For My New Online Sailboat Mechanic Business?” [Case Study in Location Independence]

13 Nov 2025

Contributed by Lukas

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 ...

#831 How 1 New Feature Can 10x Your Pricing + 4 More Insights From DCBKK

06 Nov 2025

Contributed by Lukas

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...

#830 From Ex-Special Ops to 6-Figure Performance Coach ft. Itamar Marani

23 Oct 2025

Contributed by Lukas

Could your biggest strength also be sabotaging your success? This week Itamar Marani, ex-Special Ops turned mindset coach, reveals how he turned resil...

#829 “Scaling on Steroids” with AI Automation ft. Juan Montero

16 Oct 2025

Contributed by Lukas

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...

#828 Numbers Gone Wild: The Hidden Cost of Being Data-Driven

09 Oct 2025

Contributed by Lukas

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 meas...

#827 Wealth Without a 7-Figure Exit: 5 Steps

02 Oct 2025

Contributed by Lukas

Dan and Ian share 5 money tips for bootstrappers—from prioritizing personal finance and investing to getting in the company of other entrepreneurs. ...

#826 How to Get Rich on X With a Fake Persona

25 Sep 2025

Contributed by Lukas

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 o...

#825 How to Instantly Improve Your Lead Pipeline by 20-50%.mp3

18 Sep 2025

Contributed by Lukas

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 ...

#824 The Outsourcing Shake-Up: LATAM vs. Philippines

11 Sep 2025

Contributed by Lukas

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 gett...

#823 Why $120K From Your Biz Beats $150K at a Job

04 Sep 2025

Contributed by Lukas

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, an...

#822 5 Bootstrapper Takeaways from Hormozi’s $100M Launch

28 Aug 2025

Contributed by Lukas

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 f...

#821 $400K in Points & 100% Vibe Coded Shopify Forecasting App with “SpyGuy” Allen Walton

21 Aug 2025

Contributed by Lukas

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 ...

#820 Top 5 SEO Tactics That Still Work in 2025 with Sean Markey

14 Aug 2025

Contributed by Lukas

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 exp...

#819 Why Founders Shouldn’t Delegate AI (Barcelona Recap)

07 Aug 2025

Contributed by Lukas

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 cuttin...

#818 The Content Flywheel Behind a 7-Figure Education Business ft. Timothy Moser

31 Jul 2025

Contributed by Lukas

Timothy Moser, founder of LearnCraft Spanish, shares how he scaled a 7-figure education business in today’s fast-changing online landscape. From why...

#817 Health Advice That Goes Against Everything You Know ft. Jay Feldman

24 Jul 2025

Contributed by Lukas

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 r...

#816 Reddit Hot Takes on Entrepreneurship: Founders React

17 Jul 2025

Contributed by Lukas

Dan and Ian respond to a series of spicy "unpopular opinions" about entrepreneurship, employment, digital nomadism, and lifestyle design, sourced stra...

#815 Zero-Profit Events, CFO Swaps, and LATAM Talent: 2025 Halftime Report

10 Jul 2025

Contributed by Lukas

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...

#814 Growth vs. Optimization — 90% of Growth Comes from 10% of Activities?

03 Jul 2025

Contributed by Lukas

What happens when you’ve optimized everything… and growth still stalls? In this episode, Dan and Ian break down a powerful distinction most founde...

#813 7-Figure Marketing with Zero Ad Spend ft. Karla Singson

26 Jun 2025

Contributed by Lukas

What marketing strategies are actually working in 2025? Karla Singson shares standout tactics from a DC Mexico meetup she hosted, where 6- and 7-figur...

#812 From Struggling Plumber to $57K MRR w/ Tom Richards

19 Jun 2025

Contributed by Lukas

From hating life on a Sydney construction site to building a $57K/month agency from Bali, Tom Richards—founder of PlumbElec Marketing—has lived th...

#811 The Brutal Truth About Business Exits with Rob Walling

12 Jun 2025

Contributed by Lukas

Thinking of selling your business one day? Or never planning to? Either way, this conversation could change how you build. Rob Walling has seen it all...

#810 The Lifestyle Business Playbook (2025 Edition)

05 Jun 2025

Contributed by Lukas

Is the “lifestyle business” still alive in 2025? Dan chats with longtime friend Jeff Pecaro about the evolution of internet business, what today’...

#809 Financial Traps, Profit Truths, and What’s Next at TMBA

29 May 2025

Contributed by Lukas

Many founders hit $3M in revenue and stall out. In this episode, Dan and Greg Crabtree break down why—and how to fix it. They discuss “profit trut...

#808 Going Deep With Your Customers

22 May 2025

Contributed by Lukas

What 160 founders taught us at DC Mexico—why deep customer engagement beats ads, how group workshops are replacing sales calls, what lifestyle entre...

#807 Location is Leverage

15 May 2025

Contributed by Lukas

Dan shares how advanced digital nomads use geography as a lever for business growth—and why most people get it wrong. If you’re going to travel, d...

#806 50/50 Partnerships: Saying the Quiet Part Out Loud

08 May 2025

Contributed by Lukas

Dan shares why most bootstrapped business partnerships go sideways—and what to do if yours already has. Resources Mentioned: ● When Partners Fall ...

#805 What Every Profitable Business Gets Right

01 May 2025

Contributed by Lukas

This week, Dan goes back to the basics—because that’s where the breakthroughs often live. This might be the single most important episode you list...

#804 Marketing to High-Dollar Clients

24 Apr 2025

Contributed by Lukas

Dan shares a relationship-first strategy for landing bigger deals—no funnels, no ads, just a focused system that’s often more affordable and effec...

#803 I Can’t Stick With It. Should I?

17 Apr 2025

Contributed by Lukas

What if your struggle to follow through isn’t a discipline problem — but a signal? This week, Dan unpacks why many entrepreneurs bounce between id...

#802 The 10 Behaviors Killing Your Business — Masked as Productivity

10 Apr 2025

Contributed by Lukas

Some of the “smart moves” founders make might be signs of hidden resistance. This week, Dan and Ian break down 10 behaviors that can quietly kill ...

#801 Why Founders Stall at $300K + The Blank Sheet

03 Apr 2025

Contributed by Lukas

Dan shares strategies for creating value as an entrepreneur - from maximizing personal productivity to defending your creative space so you can build ...

#800 Our Lifestyle Business Non-Negotiables

27 Mar 2025

Contributed by Lukas

Dan and Ian break down what makes a great lifestyle business in 2025—one that delivers both strong cash flow and location freedom. They dive into th...

#799 90-Day Growth Plan in 10 Questions

20 Mar 2025

Contributed by Lukas

What if 90 days from now, your business was sharper, more focused, and positioned for real growth? In this episode, Dan walks you through a simple but...

#798 Observations From our Trip to Thailand

13 Mar 2025

Contributed by Lukas

Dan and Ian share key insights from their Thailand mastermind event, exploring how successful entrepreneurs balance curiosity, diverse business models...

#797 DOGE, Team Resets & The 1,000-Day Playbook

06 Mar 2025

Contributed by Lukas

Dan unpacks what business owners can adapt from DOGE’s new strategy, delivers a practical cure for practitioner syndrome (that paralyzing fear of pu...

#796 Bigger Business = More Freedom?

27 Feb 2025

Contributed by Lukas

Dan sits down with Neel Parekh (CEO of MaidThis Franchise) to talk about the shifts that drive real business growth—why decision-making matters mor...

Bonus Pod: Inside the DC in 2025

25 Feb 2025

Contributed by Lukas

The team takes you inside the DC. Who we are, what to expect, and how you can grow your business with the support of other founders on the same journe...

#795 "The Tailwind Index" & Dodging Business Blindspots

20 Feb 2025

Contributed by Lukas

The stories we tell ourselves shape our businesses—but how much of it is true? External validation, from market response to honest feedback, is key....

#794 Success Without Sacrifice?

13 Feb 2025

Contributed by Lukas

Dan breaks down five key mindset shifts for business owners in the thick of the growth grind. Inspired by Alex Hormozi’s tweet on sacrifice, he expl...

#793 The Unexpected Downsides of Selling Your Business

06 Feb 2025

Contributed by Lukas

Why do so many founders feel sad, lost, and even depressed when they come into life-changing money from exiting their business? Dan contemplates why t...

#792 Is SEO Dead?

30 Jan 2025

Contributed by Lukas

Dan discusses the shift in SEO and the decline of content sites, emphasizing the need for B2B niche content. He introduces the concept of the 'influen...

#791 Is Your Biggest Expense Helping or Hurting?

23 Jan 2025

Contributed by Lukas

One of the first questions Dan asks in his coaching sessions with 6 & 7-figure entrepreneurs is: would you re-hire your team today? Your team is likel...

#790 The 2024 Recap: Business Updates, Financial Insights & Family Matters

17 Jan 2025

Contributed by Lukas

Dan and Ian reflect on their personal and business highlights from 2024, discussing parenting, travel, finance, making hard decisions in business and ...

#789 You Already Have a Personal Brand—Here’s How to Make It Work for You

09 Jan 2025

Contributed by Lukas

A personal brand is all about perception—everyone has one, whether you like it or not. So why not take control and shape it to your advantage? In th...

#788 Niche B2B Content = Big Revenue on YouTube

02 Jan 2025

Contributed by Lukas

Shane Hummus reveals his proven strategy for turning YouTube into a reliable source of new clients and millions in revenue, showing how entrepreneurs ...

#787 10 Questions to Gain Clarity and Refocus

26 Dec 2024

Contributed by Lukas

Dan and lan break down 10 essential questions to help you reflect on the year, align your priorities, and set your business up for success-no new book...

#786 Jay Clouse - Mastering Top-of-Funnel Growth in 2025

19 Dec 2024

Contributed by Lukas

Dan welcomes back Jay Clouse, founder of Creator Science, for his third appearance on the podcast. Jay has grown Creator Science into a thriving media...

#785 Scaling to 8-Figures with Ruthless Focus and Unconventional Principles

12 Dec 2024

Contributed by Lukas

Dan talks to Matthew Newton, CEO of Leatherback Travel, about his radically unconventional approach to scaling an 8-figure business. They dive into wh...

#784 “$1.5 Million from LinkedIn: Strategies for Building Influence and Consistent Revenue”

05 Dec 2024

Contributed by Lukas

If you’re sleeping on LinkedIn, let this episode be your wake up call. Dan sits down with Dr. Alex Barker, a pharmacist-turned-entrepreneur who 10X’...

#783 “It’s easier to 10X than to 2X” + 8 Lessons from CEO Bootcamp

28 Nov 2024

Contributed by Lukas

Dan and Ian traveled to Barcelona with 12 other CEOs and founders to spend the week with Scaling Up author Verne Harnish. These are the 8 biggest take...

#782 Building ‘Brick by Brick’: Goals, Plans, Scorecards, Cadence

21 Nov 2024

Contributed by Lukas

Does your business feel stuck in 'idea mode,' constantly jumping from project to project? If you’re ready to get on track and build a more focused, ...

#781 “Build It Like You’re Gonna Sell It”

14 Nov 2024

Contributed by Lukas

Dan revives his Re-Readables series with a discussion inspired by Frank Slootman's business book Amp It Up. He delves into the book's core arguments, ...

#780 How do you grow from 7 to 8 figures?

07 Nov 2024

Contributed by Lukas

Dan & Ian talk to Lucas Peters, founder of Journey Beyond Travel (https://www.journeybeyondtravel.com/), about his plans to get to $10M in 5 years. Th...

#779 The 3 hats of bootstrapping + Insights from DCBKK 2024

31 Oct 2024

Contributed by Lukas

Dan and Ian discuss the importance of three key executive roles—CEO, COO, and CFO—within bootstrapped businesses, emphasizing the need for founder...

#778 - Agencies vs. Products + What Happened in the Amazon Aggregator Space?

24 Oct 2024

Contributed by Lukas

This week’s episode is for the business finance and idea nerds. We’re joined this week in a business breakdown session with Alexej Pikovsky of Al...

#777 Create and Communicate an Offer (That Doesn’t Suck) in 30 Minutes

17 Oct 2024

Contributed by Lukas

Selling your product or service requires using words to convey what you offer. But words alone don’t convert on-the-fence prospects into paying cust...

#776 The 4 Most Eye-Opening Lessons I’ve Learned From My Coaching Clients

10 Oct 2024

Contributed by Lukas

Dan and Ian talk to 100s of listeners a year via 1:1 coaching. In this episode they distill those calls into 4 breakthrough ideas that can change your...

#775 A Business Idea That Might Actually Work

03 Oct 2024

Contributed by Lukas

Dan considers why many of us are resistant to a certain type of business idea even when it’s been proved time and time again. He’ll also explore t...

#774 “You’re Gonna Mess It Up The Way Everybody Messes It Up”

26 Sep 2024

Contributed by Lukas

Dan paid big money for a business coach who only gave him one piece of advice. Listen to the episode to find out what it was and if it worked. Connec...

#773 6 Keys to a Successful Bootstrapped Business

19 Sep 2024

Contributed by Lukas

Dan & Ian get real about what it takes to create and maintain a successful business. They’ll walk you through their Goals/Plans/Systems (GPS) worksh...

#772 “When is my LTV good enough?” + Founder Mode for Bootstrappers

12 Sep 2024

Contributed by Lukas

“Manager mode is so tempting…” Dan & Ian discuss Paul Graham’s most recent essay titled “Founder Mode”, and how lifestyle bootsrappers can...

#770 You Don’t Have an Operations Problem. You Have a Sales & Marketing Problem.

05 Sep 2024

Contributed by Lukas

Many founders think they have an operations problem - delivery, trust, staffing, leadership. But Dan thinks you might actually have a sales & marketin...

#770 $30K a Month on Upwork in Less Than 2 Years

29 Aug 2024

Contributed by Lukas

This founder started an Upwork agency less than 2 years ago and is making $30K a month… JUST on Upwork alone. We talk about how to take it to $80K a...

#769 - $100K MRR in 12 Months… Can They Do It?

22 Aug 2024

Contributed by Lukas

These co-founders want to more than triple their revenue in the next 12 months. Despite stagnation the past few years, they believe they can get there...

#768 “Lifestyle Business” vs “Real Business”

15 Aug 2024

Contributed by Lukas

Go from being trapped in the job you’ve built for yourself to building a wealth-generating machine. Dan & Ian challenge service businesses to determ...

#767 “1,000 Customers from One Channel”

08 Aug 2024

Contributed by Lukas

Dan & Ian talk to a listener who’s running a SaaS business that within one year got to $8K MRR. The business is full of potential and opportunities,...

#766 “I’m Scared to Raise the Price”

01 Aug 2024

Contributed by Lukas

Dan & Ian talk to a listener who’s running a $1M D2C e-commerce business about the challenges and opportunities he faces as he plans for future grow...

#765 Only 3 Ways to Grow…What Would Plato Do

25 Jul 2024

Contributed by Lukas

Tackling one of the biggest problems entrepreneurs struggle with: separating their business from their own narrative and looking at it with fresh eyes...

#764 The 5 Approaches for Getting Rich + Budgeting for Wealth

18 Jul 2024

Contributed by Lukas

We speak to hundreds of entrepreneurs every year through one-on-one coaching and live events. Many of those entrepreneurs have gone on to become very...

#763 10 ideas for businesses seeking $1 Mil in Revenue

11 Jul 2024

Contributed by Lukas

In this week's conversation, Dan and Ian discuss 10 ideas that provide valuable insights and strategies for entrepreneurs looking to grow their revenu...

#762 Winning and Losing Millions with Nathaniel Eliason

04 Jul 2024

Contributed by Lukas

This week’s conversation revolves around the book 'Crypto Confidential' and explores author Nathaniel Eliason’s experience during the crypto mania...

#761 - Less Than 5% of Businesses Get to 1MIL+ - A Process to Reach the Goal

27 Jun 2024

Contributed by Lukas

Dan and Ian discuss the fundamental principles of change and how they apply to both weight loss and entrepreneurship. The conversation explores the th...

#760 - The 7 Most Common Money Mistakes for Bootstrappers

20 Jun 2024

Contributed by Lukas

Dan and Ian discuss the biggest money problems they’ve seen in their own business and hundreds of other bootstrapped businesses. Learn how to craft...

#759 - Unlock Wealth Through Financial Fluency

13 Jun 2024

Contributed by Lukas

In this episode, Dan and Ian discuss the credible and reliable ways to build wealth through your business, based on the work of author Keith Cunningha...

#758 - The Secret Weapon to Pricing Power

06 Jun 2024

Contributed by Lukas

Dan and Ian explore the concept of power in business and how businesses can transition from being a grind for the owner to having sustainable pricing ...

#757 - How Healthy is Your Business?

30 May 2024

Contributed by Lukas

Dan and Ian challenge listeners to answer five questions about your business that will help you evaluate how healthy your operations are. They cover e...

#756 - The Million Dollar Service Business Playbook

23 May 2024

Contributed by Lukas

In this week's episode Dan and Ian discuss the importance of the concept of Labor Efficiency Ratio (LER), to scale your business to a million dollars ...

#755 - Run Any Business With Just Two Simple Things

16 May 2024

Contributed by Lukas

Dan reflects on his trip to Mexico last week where he hung out with 200 founders and listeners of the pod. Vulnerability, lessons from exiting a busin...

#754 - Mastering Consistency with Adam Gilbert

09 May 2024

Contributed by Lukas

Health and wellness is the ultimate productivity hack, impacting every aspect of life. Adam Gilbert, founder of My Body Tutor, discovered that consis...

Lessons From an 18-Month Trip Around the World on $100 a Day

02 May 2024

Contributed by Lukas

This week we had the pleasure of sitting down with Barry O'Brien, a global traveler, as he shares his 18-month journey to 15 countries on just $100 a ...

#752 The 1 Million Dollar Question

25 Apr 2024

Contributed by Lukas

Crafting your value proposition into an irresistible offer is not an easy task. Andrew Jacoby, entrepreneur and visionary behind Growth Era, a thrivin...