The Death of SaaS, OpenAI's Ad Problem, and Tim Cook Steps Down episode artwork

EPISODE · Apr 22, 2026 · 26 MIN

The Death of SaaS, OpenAI's Ad Problem, and Tim Cook Steps Down

from ADSN · host James Borow and Daniel Druger

Sequoia just dropped a thesis that's shaking up the industry: the next trillion-dollar company won't sell software — it'll sell work. Meanwhile, founders are cutting SaaS tools to pay for AI tokens, Block built a "Claude for money" inside Cash App, and OpenAI can't figure out how to spend advertisers' money.This week James and Daniel dig into:• Sequoia's bold thesis: sell work, not software — and what it means for the SaaS era• Why founders are cutting SaaS tools to pay for more AI tokens• Block's Moneybot and what a "Claude for money" looks like• The clipping economy explosion — MTS, the 24/7 show trying to replace TBPN• OpenAI's ad inventory problem: $200K committed, barely $2K spent• Notion's 2026 "no roadmap" strategy• Breaking: Tim Cook steps down as Apple CEO — hardware leaders are the futurePlus: Why AI without a clear plan is actually dangerous for your productivity, Olympic fencing now looks like a lightsaber fight, and Larry Ellison's legendary defense of Elon Musk.Sponsors:• AdQuick — Making OOH advertising as easy to plan, buy, and measure as digital. adquick.com• Thrad.ai — Building the advertising infrastructure for AI. thrad.aiSTAY CONNECTEDJames on Twitter & LinkedIn – /jamesborowDaniel on LinkedIn, Instagram, TikTok – /danieldrugerSubscribe & leave a 5-star review on Spotify & Apple Podcasts. It takes 10 seconds and helps others discover ADSN.

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The Death of SaaS, OpenAI's Ad Problem, and Tim Cook Steps Down

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