How AI Is Changing Writing — With Tony Stubblebine
Tony Stubblebine is the CEO of Medium. He joins Big Technology to discuss the future of writing in the age of AI and how platforms should handle AI-generated content. Tune in to hear fresh data on ChatGPT vs. Google referral quality, Gemini’s impact on click-throughs, and Medium’s anti-spam approach. We also cover Cloudflare AI blocking, creator payouts, and Medium’s writing app. Hit play for a candid operator’s view of what survives—and thrives—as AI floods the web.
---
Enjoying Big Technology Podcast? Please rate us five stars ⭐⭐⭐⭐⭐ in your podcast app of choice.
Want a discount for Big Technology on Substack + Discord? Here’s 25% off for the first year: https://www.bigtechnology.com/subscribe?coupon=0843016b
Questions? Feedback? Write to: bigtechnologypodcast@gmail.com
Learn more about your ad choices. Visit megaphone.fm/adchoices
Why Medium is HIDING from AI | E2179
Today’s show:
On a special edition of TWiST, Alex presents a trio of TWiST 500 interviews.
First up, Medium CEO Tony Stubblebine on the company’s new Really Simple Licensing (or RSL) initiative, and how it’s helping to compensate writers for their content.
THEN, Human Native CEO Dr. James Smith joins for an even deeper dive on AI licensing, why a writer’s content isn’t just DATA to them, and why the company is pivoting away from its old marketplace model.
FINALLY, Jason Marks of TELO Trucks stops by to show off his EV mini-truck, walk us through why people need a powerful but tiny truck, and explain why they’re building trucks right here in the US of A.
Timestamps:
(0:00) Intro: It’s a trio of TWiST 500 interviews today!
(02:57) Alex chats with Medium CEO Tony Stubblebine
(04:54) Why Medium’s more worried about HIDING from AI than anything else
(10:24) Nexos.ai. Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at nexos.ai/twist.
(11:27) Show Continues…
(15:02) What is RSL and why aren’t AI companies offering publishers a good value?
(19:58) Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.
(20:59) Show Continues…
(22:03) How Medium calculates its revenue split with writers
(26:57) Alex welcomes Human Native CEO/founder Dr. James Smith.
(27:34) Writers see their content as their life’s work, but tech co’s just see DATA
(30:01) DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to DevStats.com/twist
(31:06) Show Continues…
(33:01) Why H.N. is pivoting away from licensing and the marketplace model
(47:23) TELO Trucks CEO Jason Marks joins the show
(48:25) What is a “mini-truck” and why they’re TELO’s focus
(52:28) Why TELO is building their EV trucks right here in the US
(54:42) Why towing capacity still matters, even on a mini-truck
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
Follow Lon:
X: https://x.com/lons
Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm
Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
Thank you to our partners:
Nexos.ai. Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at nexos.ai/twist.
Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.
DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to DevStats.com/twist
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
#800: Ev Williams — The Art of Pivoting (e.g., Odeo to Twitter), Strategic Quitting, The Dangers of Premature Scaling, Must-Read Books, and More
Ev Williams is the co-founder of Mozi, a new social network that helps you connect in person with the people you care about. Over the past 25 years, Ev has co-founded several companies that have helped shape the modern internet—including Blogger, Medium, and Twitter. This episode was recorded live at Diggnation, where digg.com was relaunched. Go to digg.com and sign up to get early access when invites go out.
Sponsors:
David Protein Bars 28g of protein, 150 calories, and 0g of sugar: https://davidprotein.com/tim (Buy 4 cartons, get the 5th free.)
Sundays for Dogs ultra-high-quality dog food: https://sundaysfordogs.com/tim (save 50% on your first order)
Wealthfront high-yield cash account: https://Wealthfront.com/Tim
New clients get 3.30% base APY from program banks + additional 0.65% boost for 3 months on your uninvested cash (max $150k balance). Terms and conditions apply. The Cash Account offered by Wealthfront Brokerage LLC (“WFB”) member FINRA/SIPC, not a bank. The base APY as of 1/30/2026 is representative, can change, and requires no minimum. Tim Ferriss, a non-client, receives compensation from WFB for advertising and holds a non-controlling equity interest in the corporate parent of WFB, which creates a conflict of interest. Experiences will vary. Outcomes not guaranteed. Instant withdrawals may be limited by your receiving firm and other factors. Investment advisory services provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Securities investments: not bank deposits, not bank-guaranteed or FDIC-insured, and may lose value.
*
Timestamps:
[00:00:00] Start
[00:05:35] Kevin Rose starts the party like it's 2004.
[00:07:27] Ev's first internet product.
[00:08:54] How technology became social for Ev.
[00:10:52] The simple idea behind Mozi.
[00:12:05] Strategic quitting vs. sunk-cost perseverance.
[00:18:36] How Odeo begat Twitter.
[00:22:01] Twitter's $11,000 SXSW 2007 inflection point.
[00:23:45] Ev's hopes for Mozi's evolution.
[00:25:02] Favorite books and information inputs.
[00:30:45] Raising a generation to co-exist with AI.
[00:33:12] Ev's billboard.
[00:35:56] How Ev learned to manage his feelings.
[00:37:16] Facing strangers as an introvert with the Hoffman Process.
[00:39:57] Recently adopted habits that have galvanized positive change.
[00:42:44] The silver lining of being fired from Twitter.
[00:45:18] Contemplating how the universe works with The One by Heinrich Päs.
[00:47:04] How Ev stocks his reading list arsenal.
[00:50:26] Big thoughts on a Medium regret.
[00:52:47] Resisting the urge to bloat Mozi with superfluous features.
[00:55:40] How Mozi balances privacy with utility.
[00:57:40] Parting thoughts.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Medium: Reaching Profitability while The Internet is Broken + CorePod | E2003
This Week in Startups is brought to you by…
Notion. Notion Projects combines project management with your docs, knowledge base, and AI. Try notion projects for free at notion.com/twist
Brex. The financial stack founders can bank on. Brex knows cash is king for startups, so they built a banking experience that takes every dollar further. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24
OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at https://www.openphone.com/twist
*
Timestamps:
(0:00) Tony Stubblebine of Medium joins Alex.
(3:10) The broken internet and ad-based models
(5:57) Impact of AI on content creation and platform quality
(10:01) Medium's curation and financial model
(11:18) Notion - Try notion projects for free at https://www.notion.so/twist
(18:23) Medium's growth, geographic expansion, and AI translation
(20:02) Brex - Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24
(22:05) AI-driven media platforms and the impact of AI spam
(29:32) OpenPhone - TWiST listeners can get an extra 20% off any plan for your first 6 months at https://www.openphone.com/twist
(30:59) Medium's subscriber growth and financial milestones
(34:35) AI data exclusivity and challenges in forming training data cohorts
(41:26) Medium's venture scale potential, profitability, and mission
(45:17) CEO's mindset and financial scaling towards 10 million subscribers
(50:41) Tony's personal use of AI in his workflow
(53:24) Future of AI in practical applications and business model disruption
(57:09) Organizing content and the challenge of integrating different formats
(1:02:19) Growth potential of niche markets and Medium's independence
(1:06:23) Jam with JCal! Introduction to Ulan Abdurazakov and CorePod
(1:07:27) Corepod product discussion and go-to-market strategy
(1:17:23) Jason Calacanis's advice on testing and market validation
*
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
*
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Check out Medium: https://medium.com/
Check out CorePod: https://www.corepod.tech/
Enter the Jam with JCal contest: https://www.jamwithjcal.tech
*
Follow Tony:
X: https://x.com/tonystubblebine
LinkedIn: https://www.linkedin.com/in/tonystubblebine/
*
Follow Ulan
X: https://x.com/defoemark
LinkedIn: https://www.linkedin.com/in/ulanbek-abdurazakov/
*
Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm
*
Thank you to our partners:
(11:18) Notion - Try notion projects for free at notion.com/twist
(20:02) Brex - Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24
(29:32) OpenPhone - TWiST listeners can get an extra 20% off any plan for your first 6 months at https://www.openphone.com/twist
*
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
*
Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
Twitter, Medium and Blogger: Ev Williams
As co-founder of Twitter and founder of Blogger and Medium, Evan Williams literally helped change the conversation: he understood that real-time connectivity—being able to write a post and have people read it seconds later—was the future of engagement online. A Nebraska farm boy who dropped out of college, Ev ran into several business failures before starting Blogger, and—after it sold to Google—launching Twitter with Jack Dorsey and others. Ev also came to learn that he understood product better than people, a trait that would contribute to his eventual ouster as Twitter CEO. After that crushing blow, he returned to his first love by starting Medium, a blogging site for posts that are neither too short or too long.
This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Josh Newell and Gilly Moon.
You can follow HIBT on Twitter & Instagram, and email us at hibt@id.wondery.com.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Why Medium is opting out of AI
This week we had Medium CEO Tony Stubblebine, the CEO of Medium.com, a publishing platform that he has helmed for more than a year.
Medium has gone through a number of versions over the years. Pivots, if you will. But what has been a steady focus in Medium's life in recent years has been its subscription business. Medium offers a paid membership tier that costs $5 per month or $50 per year. And, Tony was willing to share, it's growing once again and is heading toward a pretty key milestone.
We also got into:
The business of the written word.
Medium's stance on AI and what its posture says about how the company views the value of writing. (More on the matter from TechCrunch here.)
Why Medium thinks that everyone has something worth saying.
There's a little bit of media insider chat during this podcast, which we hope you enjoy. As always, we're back with our weekly roundup on Friday. Talk then!
For episode transcripts and more, head to Equity’s Simplecast website.
Equity drops at 7 a.m. PT every Monday, Wednesday and Friday, so subscribe to us on Apple Podcasts, Overcast, Spotify and all the casts. TechCrunch also has a great show on crypto, a show that interviews founders and more!
Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products.
Learn more about your ad choices. Visit megaphone.fm/adchoices
Recode Decode: Facebook’s former security boss Alex Stamos and Twitter co-founder Ev Williams (Live)
Alex Stamos, the former Chief Security Officer at Facebook, and Ev Williams, the co-founder of Twitter and CEO of Medium, talk with Recode's Kara Swisher in these live interviews from the 2019 Collision conference in Toronto, Canada.
In the Stamos interview: Is Facebook misunderstood?; Stamos’ proposed solutions; legitimate candidates vs. the Russians; how to protect ourselves from all election attackers; the weaponization of Facebook’s products; America’s reluctance to regulate; breaking up Facebook and Google; why big companies need to stop rewarding employees with stock; Stamos’ recommendations for Mark Zuckerberg; and is Facebook actually committed to change?
And in the Williams interview: Why he left the board of Twitter; where social media is right now; why his venture firm Obvious Ventures doesn’t invest in social; its investment in Beyond Meat; Williams’ theories of venture investing; the lack of diversity in what companies get venture funding; how techlash has changed Silicon Valley; the many iterations of Medium; would Williams buy established media companies?; and is he worried about the media?
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Never underestimate your first idea, w/Twitter/Medium's Ev Williams
Never put a limit on your first idea. It could span your entire career. Ev Williams, co-founder of Twitter and Medium (and before that: Blogger), shares what he learned in every iteration of his grand vision to connect the world’s brains. A reminder that passion and perseverance can be paths to scale. Cameos: "grit" expert Angela Duckworth and Facebook COO Sheryl Sandberg.
Read Grit: The Power of Passion and Perseverance by Angela Duckworth
Read a transcript of this interview at: https://mastersofscale.com/ev-williams-never-underestimate-your-first-idea/
Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Recode Decode: Ev Williams, Medium CEO
Medium CEO Ev Williams talks with Peter Kafka about founding his third company that makes it easier to "write on the Interwebs," and what makes Medium different from Blogger and Twitter. He also discusses why publishing on anything other than a platform doesn't make sense any more, and offers some insight into why Twitter's board seemingly changed its mind about Jack Dorsey's eligibility to be CEO again..
Learn more about your ad choices. Visit podcastchoices.com/adchoices
