The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026
Episode of the bossbabe podcast · September 29, 2026 · 1 h 9 min
Natalie Ellis and author Ryan Levesque discuss the hollowing-out of mid-tier offers, rejecting AI-written marketing, email-centered audience building, and sustainable business sizing.
Summary
Natalie Ellis interviewed digital entrepreneur Ryan Levesque, creator of the quiz funnel approach and author of Ask and Return to Real. Levesque argued that AI and wealth inequality have produced a "great bifurcation" in which value migrates to free and ultra-premium offerings while mid-tier $2,000–$3,000 offers hollow out. He recounted his path from a Scrabble tile jewelry business to partnerships that were sold to NBC/Golf Channel and PayPal, and the training and software company he sold in 2024.
Levesque contended that audiences now crave what is "real," citing Instagram head Adam Mosseri, and framed marketing through neuroscience, arguing that oxytocin, elicited by physical presence and storytelling, matters more than dopamine loops. He described his "Embarrassing Confession" email admitting his content had been ghostwritten and AI-generated, after which he wrote his weekly newsletter himself for 115 consecutive weeks. He advised using AI for back-office work rather than customer-facing content, and said in-person events should be central to expert businesses. Ellis argued that people increasingly pay for experience rather than expertise.
Both discussed right-sizing a business and avoiding lifestyle creep; Levesque used his Vermont farm as a metaphor for regenerative versus extractive growth, and Ellis described rebuilding her company after postpartum. Levesque recommended a "1-1-1" model (one way to attract, convert and serve), a weekly email at the center of the business, and one social channel with one avatar and one content format. He argued evergreen content and courses are dying because AI can replicate them, cited his viral piece "The Shape of Enshittification" as a payoff of persistence, and closed by describing his family's move to a 100-acre farm.
Chapters
- 1:33
Are mid-tier offers dead?
Levesque describes a great bifurcation pushing value to free and ultra-premium offers while the middle hollows out.
- 4:17
Levesque's background and quiz funnels
Levesque recounts his niche businesses, quiz funnel partnerships, exits, and his book Ask.
- 7:45
The market craves what is real
Levesque argues trust in automated, personalized-at-scale marketing has collapsed in the AI era.
- 10:34
Oxytocin, storytelling and in-person events
Levesque frames trust through oxytocin and argues storytelling and live events are key post-AI skills.
- 17:07
The Embarrassing Confession and AI copywriting
Levesque explains why he stopped using ghostwriters and AI and where AI belongs in a business.
- 25:46
The right size for a business
Using his farm as a metaphor, Levesque argues for sustainable rather than scalable businesses.
- 33:31
Cutting expenses and the 1-1-1 model
Levesque advises cutting overhead, isolating from status pressure, and focusing on one channel and one offer.
- 39:37
Email at the center of the business
Levesque lays out his weekly email plus single-channel playbook for audience building.
- 45:10
Evergreen content is dead
Levesque argues timely, personal content beats evergreen material that AI can replicate.
- 48:38
Return to Real and monetization
Levesque describes his book's thesis about counter-revolutions and his current advisory and mastermind work.
- 52:24
Resisting maximization and persistence
Levesque warns against extractive customer-value maximization and cites his viral essay after 104 weeks.
- 58:03
Life on the farm
Levesque describes moving to a Vermont farm and the idea of being analog by design.
Key points
What was said, by whom, with the exact words. Timestamps jump to the moment.
- Ryan Levesque
Levesque says that across hundreds of businesses he sees the $2,000–$3,000 mid-tier offer losing ground.
“And I see hundreds of businesses, and I can tell you right now that the middle is hollowing out”
- Ryan Levesque
Levesque argues that AI has pushed most offerings toward free while value migrates to ultra-premium extremes, hollowing out the middle market.
“we have AI that's accelerated the trend toward the infinitely scalable, which has pushed the vast majority of what it is that we do to being free”
- Natalie Ellis
Ellis reports that her low-ticket products are struggling while her high-ticket mastermind performs well.
“We're seeing low ticket just absolutely crushed right now. And then we're seeing our high ticket mastermind do really, really well”
- Ryan Levesque
Levesque argues audiences have become distrustful of automated sales processes and fake personalization, especially with AI.
“we no longer trust those automated sales processes online, the fake personalization at scale that I've used myself”
- Ryan Levesque
Levesque argues that storytelling is arguably the most valuable skill after AI because it builds emotional bonds.
“the most valuable post AI skill to really get good at is telling stories”
- Ryan Levesque
Levesque contends that in-person events should be central to expert-based businesses.
“I believe in-person events should be at the center of any transformational, educational, expert-based business”
- Natalie Ellis
Ellis argues that AI is reducing willingness to pay for expertise but people will still pay for lived experience.
“people are less willing to pay for your expertise now, but they're paying for your experience”
- Ryan Levesque
Levesque recounts confessing to his audience that for seven years his content had been written by writers and later AI.
“For the last seven years, every single piece of content, every single email, everything that you've seen with my name attached to it was actually not written by me”
- Ryan Levesque
Levesque claims general Western consumers hold contempt for AI, so businesses should avoid touting AI use for pragmatic reasons.
“the general consumer in the West right now has a level of contempt and disdain toward all things AI”
- Ryan Levesque
Levesque reports his email open rates and opportunities have increased since he began writing himself.
“I have email open rates that have never been higher. I've had more opportunity come my way in the last six months than the last six years”
- Ryan Levesque
Levesque recommends using AI for back-office automation rather than customer-facing content.
“We should be using AI to automate the back office of our business, the parts of our business that are as far away from touching our customer”
- Ryan Levesque
Levesque argues a few-million-dollar lifestyle business may be more aspirational than a $20 million business demanding constant scaling.
“a business that does a few million dollars a year that provides a great lifestyle for you and your family is, in my experience, you know, perhaps more aspirational”
- Ryan Levesque
Levesque advises focusing on one acquisition channel, one conversion method and one offer until reaching a million dollars.
“Pick one channel, one way to attract, one way to convert, and one way to serve. And do that until you get to a million dollars”
- Ryan Levesque
Levesque argues email will not be replaced by messaging platforms and should be the center of every business.
“It's not going to get replaced by Telegram or WhatsApp or Slack or Signal or any of these other messaging platforms. Email is here to stay”
- Ryan Levesque
Levesque recounts a colleague who grew from 20,000 to over 350,000 Instagram followers by committing to a single content format.
“Punchline stuck at 20,000 followers for years. In less than two and a half months, she went to over 350,000 followers”
- Ryan Levesque
Levesque argues evergreen content is dead because it is the most easily replicated by AI.
“I think Evergreen is dead. And I'll tell you why. Evergreen is the most easily abdicated to AI form of content and form of funnel that exists”
Linked moment · 48:38Skip to 48:38 using a listen link in the info box.
Ryan LevesqueLevesque argues that technological revolutions historically trigger counter-revolutions, such as romanticism and the slow food movement.
“the Industrial Revolution gave rise to romanticism in Europe and then in the United States to transcendentalism, which was a response to that”
- Ryan Levesque
Levesque says he wrote his newsletter for 104 weeks before a piece went viral across platforms.
“I wrote my email newsletter for 104 weeks before my first email that I wrote that we would repurpose and post on Substack”
People
In the conversation
- Natalie EllisFounder of bossbabe, podcast host and author of The Freedom-Based Business Method
- Ryan LevesqueDigital entrepreneur, bestselling author of Ask and Return to Real, and writer of The Digital Contrarian newsletter
Discussed
- Adam MosseriHead of Instagram, quoted on the shift from perfect to real content
- Tony RobbinsAmerican life and business coach, entrepreneur and bestselling author
Topics
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From the publisher
Entrepreneurs are rushing to incorporate AI into their workflow and marketing. But modern research warns us against this. In this episode, digital entrepreneur and bestselling author Ryan Levesque joins Natalie to break down why audiences are rejecting automation. He also explains why mid-tier offers are losing their profitability, which channels to build your audience on in 2026, and why constantly pursuing business growth comes at a cost. In this episode, Natalie and Ryan discuss: (01:37) Are $3K Offers Dead? (07:49) The Key Driver of Digital Marketing Success in 2026 (11:38) Why Storytelling and In-Person Events Are So Impactful (17:33) Outsourcing Copywriting to AI is a HUGE Mistake! (23:46) Where AI Actually Belongs in Your Workflow (26:04) Understanding the Right Size for Your Business (33:55) The Lifestyle Changes Startup Founders Need to Make (39:25) The #1 Platform For Building an Audience That Converts (45:33) Why Evergreen Content is Losing Potential for Virality (48:55) The Last Competitive Advantage in the Age of AI (52:39) When to Resist the Temptation to Scale Ryan Levesque is a 7-time Inc. 5000 CEO & Founder and two-time #1 national bestselling author. He’s generated over $100M in revenue and has successfully sold two of his companies. His work has been featured in the Wall Street Journal, Harvard Business Review, Forbes, Entrepreneur, and NBC News. Today, he serves as a Strategic Advisor to multiple businesses and writes a weekly email newsletter, The Digital Contrarian, offering unconventional business wisdom to 100,000+ subscribers. Sponsored By: Fora Travel - Visit foratravel.com/bossbabe to learn how to turn your love of trip planning into a business. FreshBooks - Get FreshBooks for less than $3 a month for your first four months at FreshBooks.com/podcast. Faire - Sign up today and get 50% off your first wholesale order, up to $100 at faire.com/bossbabe. AG1 - Save 20% on your first subscription order of AG1 Next Gen or AG1 Pro a…
Summary, chapters and key points were generated from the episode transcript on October 6, 2026. Quotes are checked word for word against the transcript.