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/

Struggling to get good results from ChatGPT or other AI tools? You’re probably prompting it wrong, and you’re not alone.

Many founders assume AI just knows what you mean. Without the right prompt structure, though, even the most powerful LLMs will fail to deliver.

In this episode, Yaniv Bernstein is joined by Jonathan Mast—seasoned entrepreneur, AI educator, and creator of the Perfect Prompt Framework—to break down how anyone, from startup founders to side hustlers, can start using AI more effectively today.

They explore the psychology behind prompting, how to build confidence using AI tools, and why embedding structured prompting into your startup can multiply productivity.

In this episode, you will:

• Learn the 4-step Perfect Prompt Framework to get better responses from AI
• Understand why AI often fails, and how it's usually your prompt (not the model)
• Discover how to overcome "AI FOMO" and start using it without feeling overwhelmed
• Hear why giving AI permission to ask you questions dramatically improves accuracy
• Explore different LLMs like ChatGPT, Claude, and Gemini, and when to use each
• Apply AI best practices to real startup workflows, from automation to documentation
• Avoid common mistakes when building AI-based systems that lack guardrails or versioning

Whether you’re just starting with AI or want to unlock its full power for your business, this is the valuable conversation every modern founder needs.

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/

Is training AI on copyrighted content stealing, or just learning? A major U.S. court just weighed in, and the verdict could rewrite the rules for startups using generative AI.

Too many founders assume "training data" is fair game but that blind spot could cost them billions. In this episode, Yaniv Bernstein and Chris Saad, experienced startup operators and product strategists, dive into a landmark copyright ruling and what it means for anyone building with AI.

They also explore why AI voice transcription tools are finally taking off after decades of mediocrity, and react to a deeply unsettling video from tech billionaire Peter Thiel, revealing Silicon Valley’s growing influence on politics and democracy.

In this episode, you will:

• Understand why a U.S. court ruled Anthropic’s AI training methods as partially legal—and partially not
• Learn the difference between fair use and piracy when it comes to LLM training
• Discover why AI voice dictation is suddenly scaling and attracting huge VC funding
• Explore the product strategy lesson behind voice tech’s decades-long false start
• Unpack how timing, quality, and market readiness affect product-market fit
• Hear the dark side of Silicon Valley power through a rare Peter Thiel clip

ChatGPT’s takeover plan: https://www.facebook.com/share/r/16S97eepGe/?mibextid=wwXIfr

Peter Thiel's philosophy: https://youtu.be/45o8tQMGtvU?si=QrJ48xsAdQS-MxAC&t=264

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/

Is AI about to transform the world… gently? Sam Altman says yes, but are we being lulled into complacency while the real risks go unchallenged?

Startups everywhere are rushing to embed AI into their workflows, but few understand just how flawed that human-AI interaction can be. From broken prompting to billion-dollar power plays, the future of AI in business is murkier than it looks.

In this episode, Chris Saad and Yaniv Bernstein break down the most urgent developments in AI and what they mean for founders and operators. They unpack Sam Altman’s “Gentle Singularity” vision, dive into Meta’s stealthy acquisition of Scale AI, and discuss a shocking study revealing that human-AI collaboration may be doing more harm than good, especially in healthcare and the workplace.

In this episode, you will:

• Understand why Sam Altman thinks AI’s future will be “gentle”—and what he might be downplaying
• Learn how Meta quietly bought 49% of Scale AI to outflank OpenAI and Google
• Explore the real-world risks of bad prompting and how it derails AI’s accuracy
• Uncover why AI literacy is now a critical skill for startups and employees alike
• Examine why Slack is locking down chat data—and what that means for workplace AI tools
• Hear how OpenAI talent is resisting $100M offers from Meta, and what that says about culture vs. cash
• Discover the hidden trade-offs in AI alignment and whether “good enough” is actually enough

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/

What if your next startup competitor doesn’t have a single employee?

AI agents aren’t just another software trend — they’re redefining the interface between humans, data, and execution, yet many founders still confuse basic chatbots with the true potential of these agents.

In this episode, Chris and Yaniv are joined by Jeremiah Owyang, General Partner at Blitzscaling Ventures and host of Silicon Valley’s top AI startup event, Llama Lounge. Together, they unpack Jeremiah’s insider thesis on the AI Agent era — and what it means for the future of software, user experience, and startups.

They explore why AI agents are replacing SaaS apps, what defines a “true agent,” and how startups should position themselves in the face of big tech platform risk.

In this episode, you will:

• Understand the difference between LLM tools and autonomous AI agents
• Discover how Crew AI scaled to 60% of the Fortune 500 using 150 agents and minimal staff
• Learn why traditional apps and websites may become obsolete in the agentic future
• Explore new go-to-market strategies and startup models for agent-driven businesses
• Evaluate how agents will access private and public data — and what that means for APIs
• Hear how to pitch agent startups to VCs looking for viral and network-effect plays

Whether you’re building in the agent ecosystem or preparing for it, this conversation will reshape how you think about the future of digital interfaces and startup opportunities.

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

This episode is brought to you by Warp Development.  Are you ready to build something that matters? Visit https://warpdevelopment.com and mention The Startup Podcast for a free consultation.

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/

Apple’s WWDC 2025 keynote revealed a lot – just not what you’d expect.

Siri’s long-awaited AI upgrade was quietly delayed, and instead Apple rolled out a grab bag of long-overdue features, flashy design updates, and deep ChatGPT integrations. Is this a bold product reset, or proof that Apple is falling behind?

Meanwhile, Elon Musk and Donald Trump butt heads, Ukraine rewrites warfare with AI-powered drones, and a16z explains how consumer AI startups can finally scale, if they get a few key things right.

In this episode, Chris Saad and Yaniv Bernstein sift through this huge week of tech news, breaking down the topics that really matter for founders and early-stage operators.

In this episode, you will:

• Understand the real implications of Elon Musk and Donald Trump’s public fallout
• Explore how the Musk/Trump feud could fracture the MAGA-tech alliance and reshape Silicon Valley politics
• Learn why Apple is releasing papers criticizing AI reasoning—and what that means for AGI hype
• Assess whether Apple’s WWDC 2025 was a quiet revolution or just a catch-up act
• Discover how Ukraine’s AI-powered drone strike changes the future of war and global defense tech
• Unpack why AI consumer startups now have better monetization paths than ever before

🔗 Full a16z post: https://www.linkedin.com/posts/justine-moore_a16z-ai-consumer-apps

From Silicon Valley’s shifting loyalties to the limits of Apple’s AI ambitions, this episode is a masterclass in how tech power is evolving and how to position yourself for it.

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/

Can consumer tech like Facebook and Oculus really help win wars?

As governments get serious about AI and startups, Silicon Valley is being dragged—sometimes unwillingly—into the global military and geopolitical game.

In this episode, Chris Saad and Yaniv Bernstein unpack how Meta is teaming up with Anduril—the military tech startup founded by Oculus’ Palmer Luckey—to bring XR (Extended Reality) to the battlefield. They also break down how Google might preemptively split itself, how UK civil servants gained 5% productivity with AI tools, and why Europe’s startup scene may finally be waking up.

In this episode, you will:

• Learn how Meta’s AR & VR technology is being integrated into U.S. military operations

• Understand the strategic irony behind Palmer Luckey and Meta partnering again

• Explore the concept of “reverse technology transfer” from consumer tech to defense

• Discover why Google may break itself up before regulators force it

• See how the UK’s use of Microsoft Copilot gave government workers a 5% productivity boost

• Unpack the EU’s new law that lets startups register and begin trading in under 48 hours

• Assess how New York is quietly becoming Silicon Valley’s biggest challenger

Whether you're a founder, operator, or just a curious mind in the startup world, this episode gives you sharp insights into how tech, defense, and regulation are reshaping the startup landscape.

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/

Are you building a startup strategy—or just making it look like you have one?

Too many founders mistake polished slide decks for actual strategic thinking, leading to misalignment, wasted resources, and failed products.

In this episode, Yaniv Bernstein and Chris Saad are joined by Marcelo Calbucci, former Amazon director and author of The PRFAQ Framework. They dive into how Amazon’s famously effective six-page PRFAQ process forces deep thinking, aligns teams, and drives billion-dollar bets—without a single slide.

They explore why most startups get strategy wrong, how to apply PRFAQs to your own company, and the real difference between outputs and outcomes.

In this episode, you will:

• Discover why PowerPoint-based strategies often lead to shallow thinking and misalignment
• Learn how Amazon's six-page PRFAQ framework drives innovation and clarity
• Understand the structure of a PRFAQ—and why it starts with a future-facing press release
• Explore the critical cultural shifts needed to make frameworks like PRFAQs work
• Compare PRFAQs with OKRs and PRDs—and learn when to use each
• Unpack the process Amazon uses to critique and improve strategy docs in real time
• Hear practical advice on adapting the PRFAQ process to your startup, even as a solo founder

Whether you're pre-launch or scaling fast, this episode gives you a blueprint for thinking deeper and aligning your team.

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/

What does it mean when OpenAI gives away $6 billion worth of equity just to bring one man on board?

In a world where design, brand, and user experience could determine AI dominance, are startups undervaluing human-centered thinking?

In this episode, Chris and Yaniv unpack OpenAI’s jaw-dropping acquisition of Jony Ive's mysterious startup “io,” and what it means for the future of AI hardware. They also break down Claude 4’s strategic shift toward coding, Klarna’s AI misfire in customer service, and Bitcoin’s stunning return to all-time highs.

In this episode, you will:

• Understand why OpenAI paid $6B for Jony Ive with no product in sight
• Explore how Claude 4 is positioning itself to dominate AI coding workflows
• Learn what Klarna’s AI rollback says about the real limits of LLMs in customer service
• Discover why prompting isn’t just for AIs—and how it applies to human leadership
• Compare deterministic vs probabilistic software—and what that means for your startup stack
• Examine how students using AI tools are reshaping education (and why it’s not all good news)
• Evaluate Bitcoin’s recent surge and whether it’s becoming a lasting store of value

Whether you're building in AI, riding the crypto waves, or figuring out where human judgment still beats automation—this episode is packed with insight from real founders navigating the edge.

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/

Is Google staging the biggest comeback in tech history? Or are we just getting swept up in the hype?

Founders often underestimate just how fast platform shifts change the rules of the game, and Google, Microsoft, and OpenAI are rewriting the rulebook in real time.

In this episode, Yaniv Bernstein and Chris Saad break down Google’s massive AI showcase at I/O 2025, spotlighting the rollout of Gemini Live, Gmail Smart Replies, and even AI-powered glasses. They also dive into Airbnb’s bold strategy to become the “Amazon for services”—and why it could either revolutionize local work or crash hard. Plus, Microsoft, Nvidia, and OpenAI are all shaping the future of how software will be built in the AI era.

In this episode, you will:

• Understand how Google is integrating AI into its entire product ecosystem—from Search to Android to Gmail
• Learn why Gemini Live and Google’s “AI Mode” could change how consumers interact with the internet
• Explore how Google is personalizing AI by tapping into your email, calendar, and Drive
• Evaluate Airbnb’s ambition to become a services marketplace—and the operational challenges ahead
• See how OpenAI’s Codex, Microsoft’s coding agents, and Windsurf’s SWE1 model are reshaping software engineering
• Discover Nvidia’s clever strategy to absorb chip competition with NVLink Fusion
• Debate whether vibe coding tools or engineer-facing AI agents will define the future of software development

Google’s making a comeback. Airbnb’s making a bold move. And AI tools are now building AI tools.It’s a lot. But we break it down so you know what matters—and what doesn’t.

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

The Startup Podcast is sponsored by Vanta. Vanta helps businesses get and stay compliant by automating up to 90% of the work for the most in-demand compliance frameworks. With over 200 integrations, you can easily monitor and secure the tools your business relies on. For a limited-time offer of US$1,000 off, go to www.vanta.com/tsp .

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/