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
(00:11:50) 15 Steps to a High-Converting Landing Page
(00:19:18) Do Webinars Still Work in 2026?
(00:24:09) What Makes a Great Lead Magnet
(00:29:09) The Power of Order Bumps and Upsells
(00:36:58) How to Use AI to Improve Your Funnels
(00:40:45) How to Make Extra Money with Trip Wires
(00:44:37) Rapid-Fire Email Tips for 2026
(00:50:49) How John is Running His 7-Figure Agency

CONNECT:

[email protected]
[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
(00:01:44) The Biggest Challenge Holding Back Your Sales
(00:05:00) Start Positioning Yourself as the Expert
(00:14:31) Conversion Rate Benchmarks to Aim For
(00:18:59) How to Go From “Good Call” to $ in the Bank
(00:26:33) Sales Best Practices in 2026
(00:32:24) 2026 Bootstrapper Trends and Predictions

CONNECT:

[email protected]
[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
(00:02:13) How to Set the Right Kind of Goal and Plan for the Year
(00:08:15) System #1 to Reach Your Goal: Budget
(00:13:03) System #2 to Reach Your Goal: Scoreboard
(00:18:19) System #3 to Reach Your Goal: Scorecards
(00:21:13) System #4 to Reach Your Goal: Cadence
(00:24:18) What to Stop Doing & What to Do More Of In 2026
(00:27:59) The Importance of Personal Reflections Before a New Year

CONNECT:

[email protected]
[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?
“3 Million in Revenue is a Death Zone" - Financial Strategy with Greg Crabtree
Health Advice That Goes Against Everything You Know ft. Jay Feldman

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
(00:03:00) Why Event Principles Are Important For All Businesses
(00:05:14) The Art of Gathering
(00:10:40) 10 Ways to Make Money With Events
(00:13:00) A New Spin on Sponsorship
(00:16:50) Case Study: Breakfast Club Austin
(00:18:48) The Costco Method
(00:21:23) Bonus Ways to Monetize Events
(00:25:08) The Biggest Challenge With Hosting Events
(00:29:24) External Event Planner vs Your Ops Manager?
(00:32:45) Five Principles for Killer Events

CONNECT:

[email protected]
[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)
How 1 New Feature Can 10x Your Pricing + 4 More Insights From DCBKK
How to Instantly Improve Your Lead Pipeline by 20-50%

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
(00:02:52) How Dan Had a Business Breakthrough in a Tuk-Tuk
(00:07:24) DC Accelerator 2.0 [Beta]
(00:11:45) Moving an In-Person Business Online: Listener Case Study
(00:23:32) Sponsor Shout-Out: SPP.co
(00:24:31) Simple Keys to a $9B Valuation in 5 Years

CONNECT:

[email protected]
[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
How 1 New Feature Can 10x Your Pricing + 4 More Insights From DCBKK
Lucy Bella Simkins Built a YouTube Channel with 10,000,000 Subscribers

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
(00:03:27) Why It’s So Hard to Describe the DC
(00:07:18) DCBKK: High-Level Overview
(00:09:02) Insight #1: Choose Your Hard
(00:12:57) Insight #2: Fractional Hiring
(00:17:23) Sponsor Break: Smash Digital & SPP.Co
(00:18:57) Insight #3: 10x Pricing with 1 Feature
(00:22:31) Insight #4: Simple Event ROI System
(00:25:25) Insight #5: Our Messaging Kinda Sucks
(00:27:00) Rapid Fire Bonus Insights and Upcoming DC Events

CONNECT:

[email protected]
[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”
The 3 hats of bootstrapping + Insights from DCBKK 2024
From Ex-Special Ops to 6-Figure Performance Coach ft. Itamar Marani

Could your biggest strength also be sabotaging your success? This week Itamar Marani, ex-Special Ops turned mindset coach, reveals how he turned resilience into revenue, scaled from $2K clients to 6-figure programs, and used battlefield lessons to transform founder performance.

LINKS

Itamar’s Book: Elite Performance: The Israeli Special Ops Mindset System to Win the War Within and Achieve Audacious Goals
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”
Connect with 6-, 7- & 8-figure founders in person and online
Hang out exclusively with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs

CHAPTERS

(00:00:43) This Week’s Guest: Itamar Marani
(00:01:09) Turning Your Niche Expertise into a Business Engine
(00:04:43) How a Failed Agency Sparked a Coaching Business
(00:09:30) Learning the Coaching Game from the Ground Up
(00:11:41) The Truth About Feeling Out of Your Depth
(00:13:54) The Evolution from $2K Clients to Six-Figure Engagements
(00:19:03) From One-on-One to Scalable Group Coaching
(00:27:19) Positioning Yourself When You Feel Unqualified
(00:33:27) Building Long-Term Value Beyond the First Program
(00:43:03) The ‘Drunk Founder’ Question That Reveals Hidden Truths
(00:49:12) How to Sell Coaching Without the Sleaze
(00:53:44) The Three Success Killers Holding You Back
(00:57:55) Understanding the Performance Traps That Limit Growth

CONNECT:

[email protected]
[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:

TMBA 524: Who Do You Think You Are? ft. Itamar Marani
“Scaling on Steroids” with AI Automation ft. Juan Montero
Numbers Gone Wild: The Hidden Cost of Being Data-Driven

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 can build practical AI agents and automations that actually drive revenue.

LINKS
Juan’s AI Automation Business: Flowgrama
Contact Juan
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”
Connect with 6-, 7- & 8-figure founders in person and online
Hang out exclusively with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs

CHAPTERS

(00:00:51) This Week’s Guest: Juan Montero of Flowgrama
(00:03:07) Discovering the Power of Automation
(00:06:32) How LLMs Changed the Game
(00:09:35) The Truth About AI and Job Security
(00:14:31) Understanding AI Agents vs. LLMs
(00:17:42) APIs: The Backbone of Automation

(00:19:29) The Founder’s AI Toolkit
(00:24:33) Making Money with Social Automation
(00:27:00) How to Avoid Getting Banned on LinkedIn
(00:35:38) Using AI Agents for Business Intelligence
(00:38:28) Building an HR Agent for Your Team
(00:45:44) The Future of CRM Is Custom-Built
(00:49:42) Founders Who Are Actually Making Money with AI

CONNECT:

[email protected]
[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:

$400K in Points & 100% Vibe Coded Shopify Forecasting App with “SpyGuy” Allen Walton
Why Founders Shouldn’t Delegate AI (Barcelona Recap)
How to Get Rich on X With a Fake Persona

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 measure becomes a target, it stops being useful — and how founders accidentally turn smart goals into bad incentives. Plus, you’ll hear six ways to build healthier systems, lead better, and stop metrics from running your company off the rails.

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”
Connect with 6-, 7- & 8-figure founders in person and online
Hang out exclusively with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs

CHAPTERS

(00:01:16) The Hair-Dye Economy & Durable Businesses
(00:03:38) The Problem with Metrics
(00:07:44) Fix #1: Revisit Your Brand Promise
(00:09:12) Fix #2: Determine a Countervailing Metric
(00:12:17) Fix #3: Combine Input and Output Metrics
(00:13:12) Fix #4: Refresh Metrics Every 90 Days
(00:14:39) Fix #5: Pulse Discipline
(00:16:05) Fix #6: The Leadership Lens
(00:20:00) The Alt Business School
(00:25:42) When a Job Post Becomes a Marketing Hack

CONNECT:

[email protected]
[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:

Wealth Without a 7-Figure Exit: 5 Steps
How to Instantly Improve Your Lead Pipeline by 20-50%
Growth vs. Optimization — 90% of Growth Comes from 10% of Activities?

Dan and Ian share 5 money tips for bootstrappers—from prioritizing personal finance and investing to getting in the company of other entrepreneurs. Follow this playbook and you could build wealth without a 7-figure exit (spoiler: only about 5% of businesses achieve this.) Free resource below!

LINKS
Share your thoughts on 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”
FREE RESOURCE: Personal Financial Dashboard for Bootstrappers
Olly Meaking’s musings on entrepreneurship and crossing 7 figures ARR:
Hang out with us at DCBKK this month
Connect with 7+ figure founders and join us in NYC this December
22 FREE business resources for location-independent entrepreneurs

CHAPTERS

Audio:

(00:00:50) How Dan Got Fired For Having Too Many Ideas
(00:02:07) 5 Money Tips for Bootstrappers
(00:03:00) Tip #1: Focus on Your Knowledge, Skillset, and Business Model
(00:04:14) Case Study: Olly Meakings, Founder of Senja.io
(00:07:13) Tip #2: Be Realistic About Your Liquidity Potential
(00:11:42) Tip #3: Keep Your Second Bottom Line Sacred
(00:16:47) Sponsor Shout-out: Smash Digital
(00:17:43) Sponsor Shout-out: SPP.co
(00:18:44) Tip #4: Be a Bull About 1 Non-Business Thing
(00:23:47) Tip #5: Surround Yourself With Other Entrepreneurs

CONNECT:

[email protected]
[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 Get Rich on X With a Fake Persona
How to Instantly Improve Your Lead Pipeline by 20-50%
Why $120K From Your Biz Beats $150K at a Job

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 online persona, is X really worth the hype for growing fast—and getting rich—in 2025?

LINKS

Hang out with us at DCBKK this October
Connect with 7+ figure founders and join us in NYC this December
This week’s sponsor: https://spp.co “Your billing, onboarding & projects in one client portal”
Remote First Recruiting: Hire Your Next Remote Team Member in 21 Days or Less
X’s Head of Product’s projections for the algorithm
LindyMan: an example of using a character or persona online
Moving From A Solopreneur Mindset To An Operator Mindset with Leila Hormozi
22 FREE business resources for location-independent entrepreneurs

CHAPTERS

Audio:

(00:00:34) Business Lessons from the Lemonade Stand
(00:02:41) How to Get Rich on X: New Thoughts

(00:10:16) Be Yourself… Or Create an Online Character?
(00:13:49) The Realistic Cost of Hiring a Ghostwriter for X
(00:16:46) Sponsor Shout-out: SPP.co

(00:17:47) Leila Hormozi’s Simple System for Delegation
(00:26:12) Location as Leverage: What if the USA Were More Affordable?

CONNECT:

[email protected]
[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:

X’s Head of Product: How to Get Rich in 6 Months

How to Instantly Improve Your Lead Pipeline by 20-50%

Location Is Leverage: How Advanced Digital Nomads Build Faster