Podcast Summary: AdExchanger Talks

Episode: "Why Medium Said No To Easy Ad Money"

Date: October 28, 2025
Host: Allison Schiff
Guest: Tony Stubblebine (CEO, Medium)

Overview: Main Theme and Purpose

This episode centers on Medium's principled rejection of traditional advertising (“easy ad money”) in favor of a subscription-driven platform with a focus on content quality, value-driven “white hat” marketing, and building genuine trust between writers and readers. CEO Tony Stubblebine discusses how Medium pulled itself back from financial crisis, the rationale behind its stance on advertising, and its unique approach to content curation in the era of AI-generated slop. The conversation also covers the state of honesty and integrity in digital marketing, the changing landscape of the internet, and practical advice on productivity.

Key Discussion Points and Insights

1. Tony Stubblebine’s Background and Philosophy

• Tony’s Path: From engineering at O’Reilly Media and Odeo (Twitter’s precursor), to founding startups in event software and habit coaching, and eventually leading Medium (02:28–04:57).

• Marketing Philosophy: Yearning for the era of "white hat content marketing," inspired by “helpful, integrity-driven” internet culture—“lead with value.” (04:57–08:26)

  "The Internet's an opportunity to be helpful to other people and once they see how helpful you are, they're going to hire you for your services. ... That felt like a very high integrity period of the Internet."
  — Tony Stubblebine (07:00)

2. The Shift from White Hat to ‘Deep Gray’ Marketing

• From Integrity to Exploitation: Growth hacking and attention-grabbing tactics have normalized questionable ethics online. (09:01–10:58)

• Cultural Impact: Many no longer recognize the moral dimension of everyday online interactions—dishonesty is pervasive and largely unchallenged.

  "The Internet is hackable ... they've lost the thread about what is honest or not and whether honesty even matters."
  — Tony Stubblebine (10:05)

3. The State of the Internet: Broken, But Still Hopeful

• Entropy and Evolution: The public web is being “corrupted”—decreasing incentives for quality content, increased AI slop—but vibrant private and semi-private spaces are emerging (subreddits, group chats). (12:10–15:05)
• Optimism: “Something beautiful will come in [to] replace what we’re used to.” (14:46)

4. Medium’s Turnaround: Why Reject Ad Money?

• Financial Crisis: Medium was losing $2.5M/month and hemorrhaging subscribers due to poor content quality. (15:25–16:34)

• No to Advertising: Rejecting the “attention economy”—rage-bait and superficial engagement that ad models necessarily promote—instead, focusing on subscriptions and “house ads” for Medium's own offerings. (16:34–19:46)

  “We thought we needed a different business model than ads… the opportunity is for us to offer an alternative.”
  — Tony Stubblebine (17:17)

• Practical Considerations: Third-party ad revenue not lucrative enough to justify the trade-offs; house ads are “much more relevant” and profitable in context. (18:45–19:46)

5. Lessons on Business Turnarounds

• Back to Basics: Shifted company focus so each role directly contributed to business health—clarity of mission and tough decisions (job cuts, cost control). (19:58–21:50)
• Soft Decision-Making Era: "Easy money" previously enabled lack of discipline in startups; a turnaround requires pointed leadership. (20:58–21:50)

6. The Subscription Model: Is It Universal?

• Not for Everyone: Subscription success depends on the value of content; professional/developmental topics monetize more easily than poetry/journalism. (23:35–27:01)
• Honesty About Commercial Viability: Some genres (e.g. poetry) are not going to support large businesses, “and that’s okay.” (25:40–26:45)

7. Marketing as a Moral Obligation

• Genuine Value vs. Manipulation: “If your coaching is so fricking powerful, then you need to beat the other coaches that are selling snake oil... It’s your moral obligation.” (33:12–36:10)

• Sales as Sorting, Not Convincing: Ethical sales/marketing is about matching, not manipulation—“does this meet your need or not?” (36:10–37:41)

  “Sales is a sorting function, not a convincing function."
  — Tony Stubblebine (35:42)

8. Content Quality in the Era of AI

• Multipronged Approach: Algorithms (machine learning) match readers to content; human and community curation injects genuine expertise and quality signals. (40:56–43:15)
• Expert Economy: “Everyone is an expert at something” and should be encouraged to contribute authentic insights, rather than high-volume “creator economy” content. (43:24–44:42)

9. Writing vs. Video: The Enduring Value of Text

• Long-Form Writing’s Strengths: Writing enables deeper thinking, more effective learning, and personal transformation for both reader and author. (48:17–51:59)

• AI and the Writing Renaissance: Effective use of AI now demands better writing skill—prompt engineering requires precision and clarity. (51:00–51:59)

• Skepticism on "Pivot to Video": Trend is cyclical and often misguided; writing remains unmatched for knowledge transfer. (52:00–53:11)

  “Writing is thinking and there's like a built in reward for the writer just by having written it for themselves.”
  — Tony Stubblebine (48:31)

10. Personal Development: Procrastination Advice

• Procrastination as Mood Management: We procrastinate to avoid mild negative feelings; overcoming it requires acknowledging and sitting with those feelings. (54:14–57:35)

• Fascinating Insight: Our brains treat “future self” the same as a stranger (“If we put you under an MRI…”). (54:11–55:04)

  “Most people try to tackle procrastination with complicated productivity systems, but the thing that actually works is just to be more comfortable having feelings.”
  — Tony Stubblebine (56:54)

Notable Quotes & Memorable Moments

• On Ads and Integrity:

  "The more you can drive attention, the more ads you can show ... But the things that drive attention are often the things that like, just personally, I don't want to see more of—angry emotional content that drives division."
  — Tony Stubblebine (17:17)

• On ‘Expert Economy’:

  “Everyone is... an expert at something. By definition, they're an expert in your own life. Something happened to you today that if you were to capture it in writing, would be helpful to someone else.” — Tony Stubblebine (43:34)

• On Writing vs. Video:

  “People really latch on to this trend… be the second or third wave where media has been asked to pivot to video. All the forums have different strengths. Medium is a place where we are champions of writing. … Writing is thinking.”
  — Tony Stubblebine (48:17–48:31)

• On the Value of $5 Content:

  “I will, after we finish recording, go to a coffee shop and spend probably 6.75 on a latte. So $5 for valuable content is not very much for sure.”
  — Allison Schiff (27:01)

Timestamps for Key Segments

• Intro and Tony’s Background — 00:00–04:57
• White Hat Marketing Philosophy — 04:57–08:26
• Gray Hat/Black Hat Culture — 09:01–12:10
• State of the Public/Private Internet — 12:10–15:25
• Medium’s Crisis & No to Ads — 15:25–19:46
• Business Turnaround Lessons — 19:58–21:50
• Subscription Models and Content Genres — 22:46–27:01
• Marketing as Moral Obligation — 32:24–38:54
• Managing Content Quality — 40:21–43:24
• Text vs. Video and AI’s Role — 48:17–53:11
• Procrastination and Productivity Tips — 53:29–57:35

Conclusion

This rich, candid episode offers a deep dive into Medium’s business and content philosophy, contemporary marketing ethics, and the evolving media landscape. Tony Stubblebine’s commitment to value-driven, “white hat” marketing is woven through tales of company turnaround, strategic product decisions, and the pursuit of a “better internet.” The episode ends on a practical personal note, with actionable advice for procrastinators and a call to embrace nuance and integrity in both business and life.