Ryan Levesque
Digital entrepreneur, bestselling author of Ask and Return to Real, and writer of The Digital Contrarian newsletter
Ryan Levesque (Digital entrepreneur, bestselling author of Ask and Return to Real, and writer of The Digital Contrarian newsletter) has appeared as a guest on 1 episode in TMT. Topics they speak about most include Artificial intelligence, Email marketing, Entrepreneurship.
In their words
Positions and remarks grouped by topic, each with the exact quote and where it was said.
Artificial intelligence
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 23:46
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 23:49
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 19:00
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 7:54
Email marketing
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 41:58
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 40:56
Entrepreneurship
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 36:56
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 30:14
Mid-tier offer pricing
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 2:08
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 2:17
The Shape of Enshittification
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 56:01
Return to Real
Levesque 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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 49:28
Evergreen content
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 45:39
The Digital Contrarian
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 23:46
In-person events
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 15:37
Storytelling in marketing
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”
the bossbabe podcast: The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026 (Sep 29, 2026) · Listen from 11:38
Appearances
The New Rules of Marketing, Building an Audience, and Digital Entrepreneurship in 2026the bossbabe podcast · Sep 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.
Often appears with
- Natalie Ellis · 1 shared episode