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 (52:41) - 10-80-10 AI workflow (54:56) - Sell certainty, outcomes (01:02:13) - Transformation vs. identity Check out today's guest, Ryan Deiss: LinkedIn: https://www.linkedin.com/in/ryandeiss Website: https://www.ryandeiss.com/ Instagram: https://www.instagram.com/ryandeiss/ Check out The Futur: Website: https://www.thefutur.com/ Courses: https://www.thefutur.com/shop Linkedin: https://www.linkedin.com/company/the-futur/ Podcasts: https://thefutur.com/podcast Instagram: https://www.instagram.com/thefuturishere/ Facebook: https://www.facebook.com/theFuturisHere/ Twitter: https://x.com/thefuturishere TikTok: https://www.tiktok.com/@thefuturishere Youtube:https://www.youtube.com/thefuturishere Check out Chris Do: Website: https://zaap.bio/thechrisdo LinkedIn:https://www.linkedin.com/in/thechrisdo/ Facebook:https://www.facebook.com/BizOfDesign Instagram:https://www.instagram.com/thechrisdo/ Twitter:https://x.com/thechrisdo TikTok:https://www.tiktok.com/@thechrisdo Threads:https://www.threads.net/@thechrisdo Zaap: https://zaap.bio/thechrisdo Clubhouse:https://www.clubhouse.com/@thechrisdo Behance: https://www.behance.net/chrisdo Learn more about your ad choices. Visit megaphone.fm/adchoices
