The Lifestyle Business Playbook (2025 Edition)

Podcast 48:03 | Download | Spotify| Stitcher | iTunes

Is the “lifestyle business” still alive in 2025?

Dan chats with longtime friend Jeff Pecaro about the evolution of internet business, what today’s solopreneurs get right (and wrong), and how constraints can lead to clarity.

They dive into pricing mistakes, the pressure to grow beyond your goals, and how to use tools like AI to think—not just automate. It’s a thoughtful, behind-the-scenes look at the business models most of us are actually running.

Plus: how to join upcoming DC BLACK masterminds for 7+ figure founders.

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CHAPTERS:

Video:

(00:00:00) What Lifestyle Business Means in 2025
(00:02:44) Early Days of Internet Money
(00:07:51) Growth Isn’t Always the Goal
(00:13:11) Why Some Founders Recreate Jobs by Accident
(00:20:47) Pricing Problems = Perception Problems
(00:28:37) Optimizing for Audience vs. Revenue
(00:33:11) Using AI as a Thought Partner
(00:38:55) Quiet Wins and Redefining Success

Audio:

(00:00:24) What Lifestyle Business Means in 2025
(00:01:37) Early Days of Internet Money
(00:03:03) Growth Isn’t Always the Goal
(00:12:49) Why Some Founders Recreate Jobs by Accident
(00:15:34) Pricing Problems = Perception Problems
(00:22:13) Using AI as a Thought Partner
(00:28:01) Optimizing for Audience vs. Revenue
(00:37:21) Quiet Wins and Redefining Success

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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.