Business Strategy Episodes
318
Sept. 15, 2026
#318: The $9/month membership earning more than $500k/year AND buying Smart Passive Income — Pt. 2 featuring Liz Wilcox
Liz Wilcox is the creator of Email Marketing Membership and the new owner of Smart Passive Income
Guest: Liz Wilcox
317
Sept. 8, 2026
#317: Selling Smart Passive Income (And What We Can Learn From It) — Pt. 1 featuring Pat Flynn and Matt Gartland
Pat Flynn and Matt Gartland are the former Co-CEOs of SPI Media
Guests: Matthew Gartland , Pat Flynn
308
June 9, 2026
#308: Live Podcast Audit: Jeremy Enns Diagnoses What’s Holding Creator Science Back
Jeremy Enns on killer podcast concepts, show premises, and what separates shows that grow from shows that stall
Guest: Jeremy Enns
304
May 5, 2026
#304: Sam Vander Wielen’s Beautifully Elegant Business: $8M+ From One Product. No Pivots. No New Offers. No Down Years.
Sam Vander Wielen is an attorney-turned-entrepeneur and creator of The Ultimate Bundle.
Guest: Sam Vander Wielen
298
March 26, 2026
#298: 9 Things I'm Doing Differently in My Business
Looking ahead at the rest of 2026
250
April 8, 2025
#250: One of my favorite questions for finding clarity
Featuring a classic story from Debbie Millman
237
Jan. 14, 2025
#237: Rachel Botsman – Trust expert on how you can earn trust with your audience
Rachel Botsman is a leading expert on trust in the modern world. She is the author of three critically acclaimed books, What’s Mine is Yours, Who Can You Trust? and How To Trust and Be Trusted.
Guest: Rachel Botsman
236
Jan. 7, 2025
#236: Mike Michalowicz – How the author of Profit First stays lean by licensing his ideas
An author with a unique business model I’m obsessed with shares what he’d do differently
Guest: Mike Michalowicz
Oct. 15, 2024
#168: Alexandra Watkins – How to invent a GREAT brand name. [Greatest Hits]
Alexandra Watkins is the founder of the branding agency Eat My Words.
Guest: Alexandra Watkins
206
Aug. 27, 2024
#206: How I’d approach hosting in-person events
A discussion with my friend, Justin Moore
Guest: Justin Moore
205
Aug. 20, 2024
#205: How I’d Start Today (If Creator Science Didn’t Exist)
What I’d do (and what I’d avoid) to set myself up for success
203
July 23, 2024
#203: Mid-Year Review: Goal progress, revenue, audience growth, and changes to my approach
At the halfway mark of 2024, go behind the scenes of my progress.
Guest: Jay Clouse
200
July 2, 2024
#200: Nathan Barry – The risks of ConvertKit’s rebrand (and how I can become a billion dollar creator)
Nathan Barry is the founder and CEO of ConvertKit (soon to be Kit).
Guest: Nathan Barry
197
June 13, 2024
#197: How to build raving fans and real connection (feat. Chenell Basilio and Becky Davidson)
Recorded at ConvertKit’s Craft + Commerce 2024
Guests: Chenell Basilio , Becky Davidson
194
May 21, 2024
#194: An honest conversation with my friend, Justin Moore (live from CEX)
Justin Moore is the founder of Creator Wizard and the most knowledgable guy on sponsorships.
Guest: Justin Moore
168
Oct. 17, 2023
#168: Alexandra Watkins – How to invent a GREAT brand name.
Alexandra Watkins is the founder of the branding agency Eat My Words.
Guest: Alexandra Watkins
148
May 9, 2023
#148: Kevin Espiritu – How Epic Gardening went from a blog to a video empire.
Epic Gardening has 2.5 million subscribers and nearly 300 million views on YouTube alone.
Guest: Kevin Espiritu
96
March 29, 2022
#96: Nathan Barry – from $150K/yr in ebooks to $30M in ARR with ConvertKit
Investigating trends of the creator economy with the CEO of ConvertKit
Guest: Nathan Barry
61
June 15, 2021
#61: Ryan Hawk – How a top podcaster approaches outreach, interviewing, and prioritizing new projects
Ryan Hawk is a keynote speaker and the host of the Learning Leader Show.
Guest: Ryan Hawk
37
Dec. 15, 2020
#37: Ali Abdaal – Making a living as a part-time YouTuber
Ali Abdaal is a Cambridge University medicine graduate, now working as a junior doctor in the UK's National Health Service (NHS). He started making YouTube videos in his final year of medical school at Cambridge University in the summer of 2017.
Guest: Ali Abdaal
36
Dec. 8, 2020
#36: Matt Ragland – Becoming a full time YouTube creator after 10 years of side hustling
Matt Ragland is an independent creator. His YouTube channel showcases videos on the Bullet Journal process, productivity, and time management.
Guest: Matt Ragland
23
Sept. 1, 2020
#23: Kwame Christian – How an expert negotiator thinks strategically about expanding his reach
Kwame Christian is one of the foremost experts in the field of negotiation and conflict resolution.
Guest: Kwame Christian
22
Aug. 25, 2020
#22: Pat Flynn and Matt Gartland – Why Pat acquired a Matt's agency in order to grow Smart Passive Income
Smart Passive Income is a media company elevating entrepreneurs to within reach of their dreams.
Guests: Pat Flynn , Matthew Gartland
19
Aug. 4, 2020
#19: Miles Beckler – Affiliate marketing, building an audience, earning trust, and making money online
Miles Beckler is an internet marketer. In 2009, he and his wife Melanie started a website about mindfulness and meditation, and that site now receives over 8M visitors per year.
Guest: Miles Beckler