Why Medium is HIDING from AI | E2179
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 16 September 2025
⏱️ 70 minutes
🧾️ Download transcript
Summary
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
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LinkedIn: https://www.linkedin.com/in/alexwilhelm
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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
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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
Transcript
Click on a timestamp to play from that location
| 0:00.0 | We are not going to make any change unless an AI company comes to the table with money. |
| 0:06.1 | I didn't want to do this not in a way that wasn't transparent to our community, but now that it's out, we can literally start having these conversations. |
| 0:17.2 | And the conversations kind of don't make sense until you have a number, right? |
| 0:20.9 | Are we saying we're going to pay every story, one penny? |
| 0:24.0 | No one's going to care, right? |
| 0:25.5 | Is it $5? |
| 0:26.8 | Well, some people are going to start to care. |
| 0:28.4 | Is it the best stories that show up in AI results over and over again? |
| 0:32.3 | Are they going to make $100,000? |
| 0:34.2 | Oh, that's going to catch people's attention. |
| 0:36.4 | And so, you know, we have to start |
| 0:39.6 | the negotiation to see where it goes. |
| 0:44.2 | This weekend startups is brought to you by DevStats. Check out DevStats today and get 20% |
| 0:50.7 | off plus access to their dedicated Slack channel. Just go to devstats.com slash twist. |
| 0:57.0 | Gusto! |
| 0:59.0 | Check out the online payroll and benefits experts with software |
| 1:02.0 | built specifically for small businesses and startups. |
| 1:05.0 | Try Gusto today and get three months free at gusto.com |
| 1:09.0 | slash twist. And nexos.aI. Stop Shadow AI in its tracks with the |
| 1:15.6 | unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at nexos.a. |
| 1:22.6 | i slash twist. That's N-E-X-O-S dot AI slash twist-S-T-T-E-S-T-E-I-S-T-E-I-T-E-E-E-X-E-E-E-S-E-E-E-E-E-E-S-E-E-E-E-E-E-E-E-E-E-E-E-E-W-E-E-E-W-E-E-E-W-E-E-E-W-E-E Now, if you're a long-term listener on the show, you know we've had Tony on before. So why now? |
| 1:45.3 | Well, just last week, Medium, along with other companies like Yahoo and Reddit, all joined |
... |
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