What happens when the internet starts charging AI to crawl its content?
And can legacy tools like Figma or Grammarly survive the AI age, or will they be replaced by smarter, faster upstarts?
In this episode, Yaniv Bernstein and Chris Saad break down some of the most important shifts in tech and business right now. From Cloudflare’s launch of AI pay-per-crawl to Grammarly’s bold acquisitions and Figma’s high-stakes IPO, this is an unfiltered look at how the AI boom is reshaping product strategy, startup success, and even the global order. Plus, they react to legendary VC Vinod Khosla’s explosive predictions about automation, abundance, and the role of China in AI soft power.
In this episode, you will:
- Discover why Cloudflare’s 402 status code could transform AI data scraping and web monetization
- Understand Grammarly’s plan to stay relevant with the acquisitions of Superhuman and Coda
- Explore how Figma’s IPO could signal the return of the public tech market—and why it’s risky
- Evaluate the threat of vibe coding tools to traditional design workflows
- Hear Vinod Khosla’s take on why 80% of jobs could be automated within 5 years
- Unpack how China might use free AI tools to gain soft power and global influence
- Learn why a high-risk, high-reward mindset defines the best founders and VCs in Silicon Valley
Whether you’re building your first startup or thinking about your AI strategy, this episode offers critical insights from people who’ve seen these cycles before and know where the puck is heading.
The Pact
Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
- Follow, rate, and review us in your listening app
- Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe
- Secure your official TSP merchandise at https://shop.tsp.show/
- Follow us here on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg
- Give us a public shout-out on LinkedIn or anywhere you have a social media following
Key links
Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A
The Startup Podcast website: https://www.tsp.show/episodes/
Learn more about Chris and Yaniv
Work 1:1 with Chris: http://chrissaad.com/advisory/
Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/
Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/
Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur
Intro Voice: Jeremiah Owyang https://web-strategist.com/
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.