Tropical MBA: Entrepreneurship & Founder Lifestyle

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 (https://docs.google.com/document/d/1jRV_ncgCWAMRB7tZZtnO7x0Tn5sE46-tYkwN6paVG3A/edit?tab=t.0)
Free Email Marketing Resources (https://datadrivenmarketing.co/resources/)
John’s Podcast: The Art of Selling Online Courses (https://www.youtube.com/@john_ainsworth/videos)
Meet John and other location-independent founders inside Dynamite Circle (https://dynamitecircle.com/)
Hang out exclusively with 7+ figure founders (https://dynamitecircle.com/dc-black)
Get 2 months of Perspective AI FREE with promo code TMBA (https://getperspective.ai/tmba)
Share your thoughts about the podcast (https://getperspective.ai/interview/tmba-feedback) [takes 2 minutes]
22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources)
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:
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:
Marketing to High-Dollar Clients (https://tropicalmba.com/episodes/marketing-to-high-dollar-clients)
6-Figure Sales Expert Calls You Out (Don’t Keep Doing This in 2026) (https://tropicalmba.com/episodes/dont-keep-doing-this-2026)
8 Simple Steps for Improving Your Sales Funnel (https://tropicalmba.com/episodes/john-ainsworth-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 (https://meetwingman.com/)
Jeff’s favorite microphone for sales calls (https://www.amazon.com/Shure-MV7X-Podcast-Microphone-Voice-Isolating/dp/B09BZZCGC8/)
Get 2 months of Perspective AI FREE with promo code TMBA (https://getperspective.ai/tmba)
Share your thoughts about the podcast (https://getperspective.ai/interview/tmba-feedback) [takes 2 minutes]
Connect with 6-, 7- & 8-figure founders in Dynamite Circle (https://dynamitecircle.com/dcbkk)
Hang out exclusively with 7+ figure founders (https://dynamitecircle.com/dc-black)
22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources)
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:
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:
Your 2026 Business Plan in 36 Minutes (https://tropicalmba.com/episodes/2026-business-plan) [FREE Resource]
$400K in Points & 100% Vibe Coded Shopify Forecasting App with “SpyGuy” Allen Walton (https://tropicalmba.com/episodes/400k-in-points-vibe-coded-app)
The Lifestyle Business Playbook (2025 Edition) (https://tropicalmba.com/episodes/lifestyle-business-playbook-2025)

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 (https://docs.google.com/document/d/1gfFSgVgexN8bq1gekgc9oHdRnJsWGA6RMp0876NotcQ/edit?tab=t.0)
Ryan Deiss on Scoreboards (https://x.com/ryandeiss/status/1991923587347825150?s=20)
Get 2 months of Perspective AI FREE with promo code TMBA (https://getperspective.ai/tmba)
Share your thoughts about the podcast (https://getperspective.ai/interview/tmba-feedback) [takes 2 minutes]
Connect with 6-, 7- & 8-figure founders (https://dynamitecircle.com/dcbkk)
Hang out exclusively with 7+ figure founders (https://dynamitecircle.com/dc-black)
22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources)
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:
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:
Growth vs. Optimization — 90% of Growth Comes from 10% of Activities? (https://tropicalmba.com/episodes/growth-vs-optimization)
“3 Million in Revenue is a Death Zone" - Financial Strategy with Greg Crabtree (https://tropicalmba.com/episodes/3-million-death-zone)
Health Advice That Goes Against Everything You Know ft. Jay Feldman (https://tropicalmba.com/episodes/health-advice-against-everything-you-know)

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) (https://getperspective.ai/interview/tmba-feedback)
Get 2 months of Perspective AI FREE with promo code TMBA (https://getperspective.ai/tmba)
FREE Checklist: How to Host a Killer Event in 20 Steps (https://docs.google.com/document/d/14e0cea4WGDEPKZEB2Skg7b41KTPZxA9Jy-nwzgRN3q0/edit?usp=sharing)
Connect with 6-, 7- & 8-figure founders in Mexico City (https://dynamitecircle.com/)
The Art of Gathering by Priya Parker (https://www.priyaparker.com/book-art-of-gathering)
Hang out exclusively with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black)
22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources)
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:
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 Can I Get Customers For My New Online Sailboat Mechanic Business?” (Case Study in Location Independence) (https://tropicalmba.com/episodes/get-customers-for-online-business)
How 1 New Feature Can 10x Your Pricing + 4 More Insights From DCBKK (https://tropicalmba.com/episodes/1-new-feature-10x-pricing)
How to Instantly Improve Your Lead Pipeline by 20-50% (https://tropicalmba.com/episodes/improve-your-lead-pipeline)

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. (https://getperspective.ai/tmba)
This week’s sponsor: SPP.co “Your billing, onboarding & projects in one client portal” (https://spp.co/)
Tweet about $9B Vercel (https://x.com/asmartbear/status/1986158736730419394?s=20)
Amp It Up by Frank Slootman (https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115)
Connect with 6-, 7- & 8-figure founders in Mexico City (https://dynamitecircle.com/)
Hang out exclusively with 7+ figure founders and join us in NYC this December (https://dynamitecircle.com/dc-black)
22 FREE business resources for location-independent entrepreneurs (https://tropicalmba.com/resources)
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:
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:
Our Lifestyle Business Non-Negotiables (https://tropicalmba.com/episodes/lifestyle-business-non-negotiables)
How 1 New Feature Can 10x Your Pricing + 4 More Insights From DCBKK (https://tropicalmba.com/episodes/1-new-feature-10x-pricing)
Lucy Bella Simkins Built a YouTube Channel with 10,000,000 Subscribers (https://tropicalmba.com/episodes/lucy-youtube-channel)