Why Medium is HIDING from AI | E2179
16 September 2025

Why Medium is HIDING from AI | E2179

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Podcast: This Week in Startups (LS 64 · TOP 0.05% what is this?)
Episode: Why Medium is HIDING from AI | E2179
Pub date: 2025-09-16

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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


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Check out the TWIST500: https://www.twist500.com

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X: https://x.com/lons


Follow Alex:

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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:

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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



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