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

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(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]

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 Fortune 500 companies were created during a recession or economic crisis.

With the rise of AI, sociopolitical unrest, and the post-COVID landscape, what new ideas and businesses will emerge in 2026?

This week's sponsor is Bento!

LINKS

The Age of Disclosure

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(00:00:13) Change = Opportunity

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 if 90 days from now, your business was sharper, more focused, and positioned for real growth? This simple but powerful 10-question framework is designed to help you identify your biggest challenge, clarify your team’s focus, and uncover new opportunities to stand out in your market.

LINKS

90 Day Business Clarity Worksheet

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(00:03:29) Biggest challenge and next steps

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:

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 Meetup.com, but also literal rockstar Keith Murray of We Are Scientists.

From “friendly” acquisitions to hiring frameworks and thoughts on leadership, this is what’s top of mind for 7 and 8-figure location independent founders going into 2026.

LINKS

Meet location-independent founders inside Dynamite Circle

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(00:05:22) 7-Figures and Location Flexibility

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:

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 of Data Driven Marketing, says you’re leaving tons of money on the table if you’re not doing it well.

John is back on the pod to share his best tips and tactics on landing pages, upsells, lead magnets, and more. You might want to take some notes for this one!

LINKS

Rolodex Marketing Resource

Free Email Marketing Resources

John’s Podcast: The Art of Selling Online Courses

Meet John and other location-independent founders inside Dynamite Circle

Hang out exclusively with 7+ figure founders

Get 2 months of Perspective AI FREE with promo code TMBA

Share your thoughts about the podcast [takes 2 minutes]

22 FREE business resources for location-independent entrepreneurs

CHAPTERS

(00:02:11) Email Marketing: A Must-Have Money Maker

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:

Marketing to High-Dollar Clients

6-Figure Sales Expert Calls You Out (Don’t Keep Doing This in 2026)

8 Simple Steps for Improving Your Sales Funnel

Sticking rigidly to your sales scripts, hiring and firing sales reps, and positioning yourself as a freelancer instead of the expert: these mistakes will cost you in 2026 if you don’t address them now.

6-figure fractional sales manager, Jeff Pecaro, joins us once again to reveal his best sales insights and call us out on the mistakes we need to leave behind in 2025.

Plus, we get into how he and other 6-7 figure businesses inside Dynamite Circle are scaling with just one human and multiple bots.

LINKS

How to work with Jeff

Jeff’s favorite microphone for sales calls

Get 2 months of Perspective AI FREE with promo code TMBA

Share your thoughts about the podcast [takes 2 minutes]

Connect with 6-, 7- & 8-figure founders in Dynamite Circle

Hang out exclusively with 7+ figure founders

22 FREE business resources for location-independent entrepreneurs

CHAPTERS

(00:00:13) Today’s Guest: Jeff Pecaro

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:

Your 2026 Business Plan in 36 Minutes [FREE Resource]

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

The Lifestyle Business Playbook (2025 Edition)

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 few hours. Get ready for your best year in business yet, with clarity and intention.

LINKS

FREE Resource: Plan Your 2026 With Clarity and Intention

Ryan Deiss on Scoreboards

Get 2 months of Perspective AI FREE with promo code TMBA

Share your thoughts about the podcast [takes 2 minutes]

Connect with 6-, 7- & 8-figure founders

Hang out exclusively with 7+ figure founders

22 FREE business resources for location-independent entrepreneurs

CHAPTERS

(00:00:14) A Reliable Framework for Annual Planning

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:

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

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 last 12-ish years, and we feel like we’ve finally (sorta) cracked the code.

Our Senior Community Manager at Dynamite Circle, Alex Harling, walks us through the guiding principles for hosting a 10/10 event. Apply these to your next sales call, group onboarding session, webinar, or in-person event.

LINKS

Share your thoughts about the podcast (takes 2 mins)

Get 2 months of Perspective AI FREE with promo code TMBA

FREE Checklist: How to Host a Killer Event in 20 Steps

Connect with 6-, 7- & 8-figure founders in Mexico City

The Art of Gathering by Priya Parker

Hang out exclusively with 7+ figure founders and join us in NYC this December

22 FREE business resources for location-independent entrepreneurs

CHAPTERS

(00:01:48) The Man Behind Our Last 10/10 Event: Alex Harling

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 Can I Get Customers For My New Online Sailboat Mechanic Business?” (Case Study in Location Independence)

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

We’ve learned a lot from our listeners, and you can learn a lot from your customers. Try Perspective AI.

This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal”

Tweet about $9B Vercel

Amp It Up by Frank Slootman

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

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:

Our Lifestyle Business Non-Negotiables

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”

DCBKK 2025 official photos

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

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:

Dan’s keynote from DCBKK 2024 “The Four Bricks”