Tropical MBA: Entrepreneurship & Founder Lifestyle

Latest Episodes:

#736 How to Have Your Best Year $$$Wise Ever Jan 04, 2024

Show notes

This week, Dan reveals a strategic approach to decision-making intervals for achieving top-line revenue and personal income goals. Join him as he explores how this decision-making cadence serves as a compass in navigating the challenging 'messy middle' of entrepreneurship.

What’s the messy middle? You’ve found some type of product-market fit, customers are buying, and you've set revenue and profit goals. Yet, you lack an exit strategy, millions in your bank account, and an executive team running your company.

In this episode, Dan invites you into his end-of-year meeting with co-founder Ian Schoen, unveiling the inner workings of their quarterly reviews. Discover the three key questions they always address and learn how this framework can guide you out of the messy middle, ensuring this is your best year money-wise ever.

Dan & Ian’s Stuff:
The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show Notes

(00:01:16) 14 years of the Tropical MBA
(00:01:38) Setting and achieving business goals in the messy middle
(00:05:01) The framework for 90-day quarterly reviews
(00:07:30) Does your business make financial sense?
(00:11:36) Do you have the right people in the right chairs?
(00:21:55) Are you performing well in the business?
(00:24:08) How to focus on the one thing you’re best at

Links:

Public Quarterly Review Framework

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, Tommy Griffith, Justin Tan, Matt Gartland, Travis Jamison, Ayman Al-Abdullah, Tynan, Lucy Bella Simkins, Brian Balfour, Nick Huber, Dana Lindahl, Anthony Fasano, Adam Palmeter, Carrie & Dave McKeegan.

Additional episodes you might enjoy:

An 8-figure exit and revisiting the 1,000-day principle

Non-Obvious Ways to Grow Your Business + Favorite Moments of 2023

End-of-Year Brainstorming, Goal-Setting, and a Mexico Meltdown

#735 An 8-figure exit and revisiting the 1,000-day principle Dec 28, 2023

Show notes

Can you make a life-changing decision based on assumptions you pulled off the internet?

This question and many others are answered in today’s fascinating interview with two of Dan’s mentors and longtime friends.

They recently exited one of their businesses (they’re still running the other!) for 8-figures, and they share the details of their process from deciding to sell, preparing for the sale, vetting acquirers, and what happens after. Hear how they spun up another business on the side and are maintaining the cash flow from that as they sit on the cash pile from the sale.

But perhaps their biggest accomplishment is raising three thoughtful, curious kids while running their two incredible businesses and living all over the world in places like Bali, Costa Rica, Spain, and more.

Dan & Ian’s Stuff:

The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show Notes

(00:00:42) Intro
(00:03:03) Revisiting the 1,000 day principle and questioning the 3,000 day principle
(00:03:52) Career milestones in entrepreneurship
(00:09:18) Maintaining pricing power in a productized service
(00:10:24) Setting financial goals and getting real with personal expenses
(00:16:36) Retirement planning with financial planners
(00:19:05) Selling a business: approach to sales process
(00:21:48) Selling a business: acquisition process and unexpected offer
(00:28:59) Selling a business: legal and financial aspects
(00:34:46) Selling a business: emotions and negotiation process
(00:37:10) Scaling a new business and selling a golden egg
(00:44:05) Parenting, wealth, and financial priorities
(00:46:06) Raising entrepreneurial children

Links:

Additional episodes you might enjoy:

#733 End-of-Year Brainstorming, Goal-Setting, and a Mexico Meltdown

#618 Exploring Alternative Education Options for Nomadic Families

#565 The Origins of the 1,000 Day Principle

#734 Non-Obvious Ways to Grow Your Business + Favorite Moments of 2023 Dec 21, 2023

Show notes

As 2023 comes to a close, Dan & Ian reflect on how their business did in 2023 and share some of their favorite moments from the year.

They’ll also talk about what makes a compelling offer, the “non-obvious ways” to grow your business in 2024, and why you should dream bigger than the numbers when goal setting.

But first, Dan shares the top business books and podcast episodes that inspired him this year just in time for your holiday travels.

Dan & Ian’s Stuff:

The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show Notes:

(00:00:50) Intro
(00:01:57) Dan’s favorite business books in 2023
(00:08:37) The podcast episodes that inspired business decisions this year
(00:13:15) Gift list for entrepreneurs
(00:19:36) An undervalued business-improving idea that anyone can do
(00:31:09) Why did our tweet go viral? Our search for speakers and facilitators is turning into quite the contest
(00:40:22) Our new product and how you can copy it
(00:44:31) 2023 business updates
(00:47:41) Favorite moments from the year

Links:

- DC Mexico tickets
- DC Black Facilitator position
- DC conversation cards

Additional episodes you might enjoy:

End-of-Year Brainstorming, Goal-Setting, and a Mexico Meltdown

What is the Michael Jordan of Business Models?

Insights from DCBKK 2023: The UI vs API of a Location, How Bootstrappers Are Getting Wealthy, 2024 Business Strategy, and More

#733 End-of-Year Brainstorming, Goal-Setting, and a Mexico Meltdown Dec 14, 2023

Show notes

Dan & Ian offer up some end-of-year thought experiments for founders, including how to re-visualize your business, capitalize on strategy, and ensure that you are in the right role in your business.

Most founders assume they are the “executive” in the business, but more often than not, their daily behaviors are that of a director or manager. Understanding where you sit in your organization can make a huge difference in your ability to scale.

Plus, explore the business diagnostic: what would a PE firm do with your business? A helpful exercise to get you thinking objectively about the decisions that need to be made in your business.

Lastly, the guys relive the Mexico Meltdown, otherwise known as the DC Mexico launch. Tune in to hear what went down.

Dan & Ian’s Stuff:

The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show Notes

(00:00:52) Intro
(00:01:22) We’re hiring mastermind facilitators
(00:02:20) DC Mexico meltdown
(00:08:10) What would a PE firm do with your business?
(00:15:32) Using org charts to change your business
(00:26:47) New trends and a business idea
(00:30:13) 3-year goal setting for year-end

Links:

Additional episodes you might enjoy:

Can Org Charts Be Sexy? + NYC Drinking Stories

What is the Michael Jordan of Business Models?

Dissecting the American Dream & Business Lessons from the Elon Musk Bio

#732 Can Org Charts Be Sexy? + NYC Drinking Stories Dec 07, 2023

Show notes

Dan & Ian unravel the complexities of job titles and organizational frustrations post-DC Black event, offering solutions through org chart brainstorming, a new business idea, and how much you should be investing into networking strategies based on your income.

Plus, see what UI and API score they give NYC after spending the weekend there.

Dan & Ian’s Stuff:

The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show Notes:

(00:00:59) Intro
(00:08:05) UI & API score for NYC
(00:11:01) The danger of inaccurate titles for employees
(00:18:55) How to use org charts as a brainstorming tool
(00:25:47) New business idea: Be the money person
(00:28:46) How much $$ to invest in your network
(00:37:21) Meet us in Mexico in May

Links:

Additional episodes you might enjoy:

Insights from DCBKK 2023: The UI vs API of a Location, How Bootstrappers Are Getting Wealthy, 2024 Business Strategy, and More

The Freedom Line, 7+ Figure Founders, and Extended DCBKK Recap

What is the Michael Jordan of Business Models?

#731 Special Edition Pod: Meet us in Mexico Dec 05, 2023

Show notes

In this special Tuesday edition of the pod, Dan & Ian make the hard sell for listeners to meet them in Mexico.

If you’re into five-star resorts, good food, frosty drinks, and nerding out about your business, consider this your official invite.

Dan & Ian’s Stuff:

The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show notes:

(00:00:00) Intro
(00:00:57) Meet us in Mexico

Links:

Get your tickets to DC MEXICO 2024

Additional episodes you might enjoy:

Insights from DCBKK 2023: The UI vs API of a Location, How Bootstrappers Are Getting Wealthy, 2024 Business Strategy, and More

The Freedom Line, 7+ Figure Founders, and Extended DCBKK Recap

What is the Michael Jordan of Business Models?

#730 Cash Flowing Your Early Retirement (10K/mo+) Nov 30, 2023

Show notes

This week, Dan continues delving into the world of coaching with a story about one company that provides highly paid professionals with a low-stress way to earn a living in the sunset phase of their careers.

Dan also interviews Sarah Weaver, a real estate investor and entrepreneur, who has achieved an impressive monthly cash flow of over $10,000 from her real estate portfolio in under five years.

Join us to glean insights from Sarah's journey, as she shares strategies for cash-flowing retirement through smart real estate investments. Sarah talks about how she bought 19 properties, the six metrics she evaluates before investing in a specific city, building a brand around her experience, and more.

Dan & Ian’s Stuff:
The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show notes:
(00:00:56) Intro
(00:01:14) The DC Black event is happening now
(00:01:44) A new Mexico event
(00:02:30) Loom use cases for async companies
(00:07:13) Ways to generate cash flow
(00:10:15) The steps to 10K+ cash flow per month from rental properties
(00:11:59) Cash flow investing vs appreciation investing
(00:14:17) What metrics to look at before you invest in property
(00:25:30) Don’t meet your heroes, get paid by them
(00:28:43) House hacking from abroad
(00:29:38) Building a brand around your personal experience
(00:37:49) How to skip right past imposter syndrome
(00:39:44) Mistakes people often make in real estate investing
(00:41:53) The no-brainer bucket list experience you should go on

Links:

- Dcbkk recap
- The Upwork Hustle w/ Sam Hill
- CEO Coaching International
- www.sarahdweaver.com
- 30 Day Stay. Use SARAH for 10% off.

Additional episodes you might enjoy:

What is the Michael Jordan of Business Models?

Dissecting the American Dream & Business Lessons from the Elon Musk Bio

Mailbag: Hang-ups, Power-ups, and Cheat Codes for Entrepreneurs

#729 What is the Michael Jordan of Business Models? Nov 23, 2023

Show notes

All we can say is that it’s extremely powerful and extremely profitable. Dan and Ian nerd out on what might be the GOAT business model of all time.

They analyze some of the best examples of said business model, and talk about ways that you can rip, pivot, and jam these ideas for your own business.

Plus, two books you should pick up that Dan simply couldn’t put down.

Dan & Ian’s Stuff:
The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show notes

(00:00:45) Intro
(00:03:11) What do you think of our vacation policy?
(00:05:01) The GOAT business model with extremely high margins
(00:09:08) The businesses doing this amazingly well
(00:32:11) Why now is the best time to implement this strategy
(00:42:00) Two books you should read over the holiday

Links:

Additional episodes you might enjoy:

Mailbag: Hang-ups, Power-ups, and Cheat Codes for Entrepreneurs

The Freedom Line, 7+ Figure Founders, and Extended DCBKK Recap

How to Build an AI Startup with Jodie Cook

#728 Mailbag: Hang-ups, Power-ups, and Cheat Codes for Entrepreneurs Nov 16, 2023

Show notes

Dan & Ian open up the metaphorical mailbag to answer some listener questions.

They reveal cheat codes for bootstrappers and how to activate them, the top reasons people can’t scale to 7+ figures, and the difference between F U money and Freedom Line money.

All that and more, including a big announcement regarding Ian’s car collection.

Dan & Ian’s Stuff:
The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Show notes:

(00:01:08) Intro
(00:02:42) The major ways people fail to scale their business beyond 6 figures
(00:18:44) The Cheat code for entrepreneurs
(00:30:22) What do you do with the F U money
(00:39:09) How to get the most out of a business community
(00:43:02) The community space has changed… sort of
(00:46:48) What’s next for our community
(00:48:27) Power ups for entrepreneurs
(00:52:31) Dan’s definition of an entrepreneur
(00:55:51) It always comes back to the entrepreneur-mobile

Links:

[Before the Exit](- Before the Exit)

Additional episodes you might enjoy:

[4 types of business coaches for 7+ figure founders and reflecting on our 15-year partnership](4 types of business coaches for 7+ figure founders and reflecting on our 15-year partnership)

[Dissecting the American Dream & Business Lessons from the Elon Musk Bio](Dissecting the American Dream & Business Lessons from the Elon Musk Bio)

[Brian Balfour’s $33M Growth Insights: Product-Market Fit, Durability, & Knowing Your Natural Limits](Brian Balfour’s $33M Growth Insights: Product-Market Fit, Durability, & Knowing Your Natural)

#727 The Freedom Line, 7+ Figure Founders, and Extended DCBKK Recap Nov 09, 2023

Show notes

This week Dan & Ian talk about a topic that came up countless times at this year’s DCBKK: Whether to exit or stay in your business.

They’ll revisit frameworks from their book Before The Exit and discuss how to figure out what's best for your business.

After that, Dan chats with DCBKK Master of Ceremonies Adam Palmeter about his experience at this year’s event compared to years past.

Dan & Ian’s Stuff:

The Newsletter
“The DC”
DC Black
Global events
Hire remote talent
Find a remote job
Listen on YouTube
Follow on Instagram
@TropicalMBA
@AnythingIan

Links:

Additional episodes you might enjoy:

Insights from DCBKK 2023: The UI vs API of a Location, How Bootstrappers Are Getting Wealthy, 2024 Business Strategy, and More

5 Things Founders Often Misunderstand about Exiting Their Business

Dissecting the American Dream & Business Lessons from the Elon Musk Bio