We're often great at making money, terrible at managing it.

Multi-exit entrepreneur David McKeegan joins us to discuss personal finance built specifically for founders:

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CHAPTERS

(00:00:00) — How Much Money Is “Enough”?

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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:

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

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

4 Ways to Start a Business From Scratch in 2026

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 used to take days or weeks. From analyzing financials to running workflows and speeding up big internal projects, these tools can act more like a business collaborator than a chatbot. They also walk through how to take the first step if you want to start experimenting.

Find Taylor

CHAPTERS

(00:00:00) AI “Superpowers” for Founders

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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:

Can Your Business Beat the S&P 500?

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 facilitator, Richard “RJ” Jalichandra, joins us this week to talk about how a small channel can still transform your company. Plus, the hidden struggles of 7+ figure founders, defining your “enough number,” and why a little retirement planning today can actually improve your decisions right now.

LINKS

RJ’s YouTube Channel

CHAPTERS

(00:04:18) How RJ Got Into YouTube

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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:

Can Your Business Beat the S&P 500?

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 you should live and work in 2026, and agentic AI use cases.

Meet lifestyle founders in Mexico this May

CHAPTERS

(00:00:00) What Founders Are Talking About in Mexico This May

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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 Build a 6-Figure Digital Business with Claude Code

How long would it take to revamp your entire business? For Elliott Zelinskas: three weeks.

LINKS

Follow Elliott on X

CHAPTERS

(00:00:00) Intro

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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

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

CONNECT:

[email protected]

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

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

CONNECT:

[email protected]

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

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

CONNECT:

[email protected]

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

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? Does gambling your way to wealth make sense? And what types of trends will emerge and strengthen in 2026?

Smart things look stupid for a while until they look smart. Dan and Jeff share their thoughts on the recent viral X article “The Prison of Financial Mediocrity” and their views on the “socially acceptable” risk of entrepreneurship as an escape from the 9-5.

LINKS

Bento will beat your current email bill — up to 70% off or $300 in credits

CHAPTERS

(00:00:52) The Traditional Path is Closed

CONNECT:

[email protected]

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

What if your systems feel broken because you’re running big-company playbooks in a small, bootstrapped business? Layla Pomper, founder of ProcessDriven, joins us to share how small teams actually build systems that work.

We cover what to prioritize before even thinking about SOPs, how to systemize without hiring an integrator, plus the AI & automation tools her audience is quietly using to move faster.

LINKS

Dive into more of Layla’s systems content

CHAPTERS

(00:01:44) Today’s Guest: Layla Pomper

CONNECT:

[email protected]

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:

[link to Doomsday Business Ideas episode]