The Futur

In this episode, Chris Do sits down with entrepreneur and Digital Marketer founder Ryan Deiss to explore how his early ventures shaped a multimillion-dollar business empire and what led to his public “retirement” from online courses. Ryan unpacks his journey from selling eBooks in college to scaling a $200M portfolio and why he believes adaptability is the key to long-term success. They discuss what happens when business identity and personal identity collide, the decline of digital courses, and how AI is reshaping the marketing landscape. Timestamps (00:00) - Intro (01:04) - $200M portfolio snapshot (03:38) - First client, no skills (05:23) - Risk time, not money (07:11) - Who you serve lesson (09:26) - SEO baby-food eBook (12:42) - From maker to publisher (15:19) - Licensing flat-fee deals (20:18) - Six-month job, quit (28:41) - Course revenue collapse (34:25) - Hard pivot calculus (39:46) - Identity, failure, recovery (41:28) - Message to entrepreneurs (48:37) - Pivot to AI services (52