The Futur with Chris Do | Ep 395: The Future of Marketing Isn’t Courses w/ Ryan Deiss

Release Date: November 6, 2025
Host: Chris Do
Guest: Ryan Deiss (Founder, Digital Marketer)

Episode Overview

In this candid and insightful conversation, Chris Do welcomes Ryan Deiss, a prominent figure in digital marketing and founder of Digital Marketer, to discuss the seismic changes happening in the online education and marketing landscape. The episode revolves around Ryan’s recent headline-grabbing decision to “retire” from making marketing courses after 25 years, the death spiral of the digital course market, and how AI is fundamentally reshaping what’s next. Ryan candidly shares entrepreneurial lessons, pivots, and his vision for the future of implementation-centric marketing.

Key Discussion Points and Insights

1. Early Beginnings: Hustling From The Dorm Room

• Starting from Scratch (01:32)
  • Ryan started Digital Marketer over 20 years ago, initially motivated to buy an engagement ring for his girlfriend (now wife).
  • He took on client work before knowing how to do it, leveraging honesty and his network to deliver results.
  • Quote: “I was only actually risking my time. I wasn’t asking my client to take a risk. I was still taking on all the risk.” (04:19, Ryan Deiss)
• First Lesson: Sell First, Build After (03:21–04:05)
  • Early on, Ryan realized the value in selling a service before perfecting it—solving real needs before investing heavily.
  • Importance of transparency: Don’t fake expertise; be honest and deliver value.
  • Leveraged a friend’s technical skills (“who, not what”) to bridge knowledge gaps.

2. From Web Design to Digital Publishing

• Turning Constraints into Strengths (12:11–13:00)
  • Ryan couldn’t get into business school due to grades, pivoted to corporate communications, and focused energy on real business applications.
  • Quote: “Constraints can be a gift. Your lack of knowledge and your lack of funds made you work in a very specific way.” (20:03, Chris Do)
• Accidental Publisher (12:58–15:00)
  • Shifted from building websites to licensing and publishing ebooks, bypassing the need to be the “expert.”
  • Saw opportunity in buying non-exclusive licenses cheaply, modeling traditional publishing houses.

3. Lessons in Growth and Failure

• Building Under Constraints (16:39–20:55)
  • Used a $250 credit card limit to finance licensing deals one at a time, reinvesting earnings.
  • Learned the importance of not seeking too much “expert” opinion early, as it can smother innovation.
  • Quote: “One of the mistakes that creative people make… is they talk about what they’re going to do before they do it and they open themselves up for outside criticism.” (20:55, Ryan Deiss)
• Advantages of Simplicity (23:38–24:40)
  • Lack of knowledge in design/software led him to make simple web pages, which retroactively proved to be the highest converting formats.

4. Making and Leaving a Market

• 25 Years of Courses (25:09–28:14)
  • Ryan created his first marketing course in 2000 and has made them consistently for 25 years.
  • Decision to retire from courses was personally significant—“felt like a death”—amid declining sales and market changes.
  • Digital Marketer is pivoting after seeing severe sales drops.

5. The Death of the Course Market

• Market Data: The Decline (28:46–33:15)
  • Course/certification revenue at Digital Marketer dropped to 20% of what it was two years ago (an 80%+ decrease), going from millions to struggling for 5-10k course launches.
  • Factors: post-Covid fatigue, market saturation, platforms like HubSpot/Facebook internalizing education, and the rise of AI.
  • Hit a crisis point: “Without the courses and certifications to bring new people in, that brand would simply die a slow and profitable death.” (33:15, Ryan Deiss)

6. Lessons on Letting Go and Moving Forward

• Emotional Detachment (34:12–39:34)
  • Now able to distance identity from his businesses. Failure is survivable and recoverable; it's important not to tie self-worth to business outcomes.
  • Empathetic Message for Entrepreneurs (40:08)
    • “If you’re surviving out there right now, especially if you’re serving small businesses, you are winning… Commit to yourself that you’re going to stay in the game.” (40:08, Ryan Deiss to camera)

7. The Last Big Sale & Market Pivot

• Farewell Bundle (42:25–45:06)
  • For the “retirement,” Digital Marketer sold all their courses/certifications—a $30k+ bundle—for $495, as both a war chest builder and to honor the work invested.
  • Dismissed accusations of “marketing gimmickry”: “We’re doing this because you weren’t freaking buying them.” (42:51, Ryan Deiss)
• Pivot to AI-Squared (47:18–53:44)
  • New model: shifting course IP from teaching humans to training AI agents to do the work for humans.
  • The 10/80/10 Model: 10% input from humans, 80% AI execution, final 10% polish from humans.
  • Moving to “AI Squared” (AI x Actual Intelligence) and “AI Accelerators”: instead of expecting clients to learn and do, have their bots/experts deliver results.

8. Timeless Business and Marketing Principles

• Transformation vs. Identity (58:22–63:16)
  • Core principle: All products/services are either selling a transformation or reinforcing identity.
  • If selling transformation, clarify “before” and “after” states across five layers: Have, Feel, Average Day, Status, Good vs Evil.
  • “The best story in the world… is the story of transformation from less desirable before state to more desirable after state.”
• Math of Scale (63:16–66:03)
  • Willing to spend up to 80% of a 30-day customer value to acquire customers—scale is about how quickly you can get your costs covered and reinvest, not just ROI percentages.

9. Philosophy on Money and Generosity

• Money as Scorekeeping (67:04)
  • Grew up lower middle class; making money was “fun” and a validation of value creation.
• On Generosity and Resentment (69:35)
  • Always picked up the tab until a friend expressed resentment at never being able to give back.
  • Quote: “If all we do is give… and we never give the people who we’re giving to the opportunity to return to us, that gratitude can turn into resentment pretty quickly…” (69:40, Ryan Deiss)

Notable Quotes & Memorable Moments

• On Selling Before You Build:
  “I didn’t sell it with any confidence… I said, look, I’m just getting started. You would literally be my first client… If I can’t pull it off, I’ll give your money back.” (04:19, Ryan Deiss)
• On Market Reality:
  “Courses… are down to about 20% of what it was just two years ago. It’s not down 20%. It’s down to 20%...” (28:46, Ryan Deiss)
• On Letting Go:
  “My companies are not my kids. I’ve got real kids at home that I love… The hard part… is I know just how much fricking work it’s going to be…” (34:12, Ryan Deiss)
• On Survival:
  “If you’re merely surviving, you’re winning… As long as you can keep rowing and as long as you can survive, this too shall pass.” (40:08, Ryan Deiss)
• On The Power of Sharing:
  “If you seek opinions too early, it may just very well kill your business.” (20:55, Ryan Deiss)
• On Marketing in an AI Era:
  “We can solve for this by saying you don’t have to go through it, you don’t have to learn this stuff because the AI already did.” (47:18, Ryan Deiss)
• On Business Principles:
  “You’re only ever selling transformation or identity reinforcement… The best brands in the world… change the stories that people tell about themselves.” (58:22, Ryan Deiss)
• On Generosity and Reciprocity:
  “If all we do is… give, give, give, and we never [give the]… opportunity to return to us, that gratitude can turn into resentment pretty quickly…” (69:40, Ryan Deiss)

Timestamps for Key Segments

• [01:32] – Ryan’s college-dorm entrepreneur origin story
• [04:19] – The psychological hurdles of selling sans experience
• [12:11] – On not studying business, but running businesses
• [16:39] – Figuring out licensing, using a $250 credit card limit
• [20:55] – Dangers of seeking early expert advice
• [23:38] – How accidental simplicity beat flashiness in web design
• [28:46] – The steep decline of the course/certification market
• [40:08] – Ryan’s empathetic message for entrepreneurs in tough times
• [42:51] – Clarification on the final course “fire sale”
• [47:18] – The AI-squared pivot: the new direction for Digital Marketer
• [53:58] – On the emotional process of sunsetting the course program
• [58:22] – Core, evergreen marketing principles
• [63:21] – The math behind customer acquisition, and willingness to spend
• [67:04] – Relationship with money, and the meaning of business success
• [69:40] – The risks of generosity without reciprocity

Takeaways and Actionable Lessons

1. Sell First, Build Second: Find a market need before making the product, and approach with honesty, not bravado.
2. Tap into Networks: Your knowledge is whom you know, not just what you know—ask for help.
3. Constraints Breed Innovation: Limited funds or expertise can force creative, scalable solutions.
4. Know When To Pivot: Watch the market data unsentimentally—don’t hold on emotionally to a dying line of business.
5. AI Is the New Implementation Layer: The information business is commodified; providing results, not training, is the next frontier.
6. Market What You Learn: Share openly, build authority, and monetize implementation/certainty, not just info.
7. You Are Not Your Business: Separate self-worth from business outcomes—failure does not define you.
8. Reciprocity Matters: Let people give back; balance is key in business and in life.
9. Timeless Principles: Transformation and identity are the two things people buy; focus relentlessly on outcomes and customer journeys.
10. Business is Math: Be willing to spend aggressively (up to break-even) to scale, but focus on the speed of payback, not just ROI.

This episode delivers an unvarnished look into the end of an era for digital courses and the dawn of AI-centric marketing—the actionable wisdom here will resonate with entrepreneurs, marketers, and creators facing rapid change and looking for what's next.