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

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

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]