Insiders React: Cloudflare Catches Perplexity Red-Handed + Wikipedia Adopts Anti-AI Slop Policy, AWS Losing Ground

Is AI threatening traditional subscription software models and accelerating competitive turnover? Sam Altman thinks so.In this episode, Chris and Ray discuss OpenAI’s GPT-5 release, and Altman's prediction that AI will enable a “fast fashion” era of SaaS, where applications can be created, deployed, and discarded in rapid cycles.You'll also hear them delve into Apple's commitment of $2.5 billion toward US-based manufacturing as part of a broader $600 billion plan, and their examination of the public spat between Elon Musk and Sam Altman on X, exploring what it reveals about ego, platform power, and the competitive dynamics shaping the AI industry.In this episode, you will:Understand why GPT-5’s biggest innovation might be routing, not raw intelligenceLearn how AI cost structures are shifting as subsidies fadeExplore the risks and opportunities in the “fast-fashion” SaaS economySee why control of the browser is the next big AI platform playAnalyse Apple’s US manufacturing move in the context of global geopoliticsRecognise the double-edged impact of AI on the labour marketHear lessons founders can apply from today’s tech power playsThe 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 appSubscribe 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 followingKey linksGet 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 YanivWork 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-mcarthurIntro Voice: Jeremiah Owyang https://web-strategist.com/

14 Elo 41min

Raising money for your startup isn’t just about pitching but navigating egos, timing, and a flood of contradictory feedback. Why do some founders win over early believers who open every door, while others get stuck in endless “soft nos”? And how do you avoid twisting yourself into a pretzel trying to please every investor you meet?In this episode, Yaniv Bernstein and Chris Saad dive into the gritty, unfiltered reality of early-stage fundraising. Yaniv shares six fresh, hard-earned lessons from raising a pre-seed round for his own startup, Violet. These are insights you rarely hear outside closed-door founder circles.In this episode, you will:Learn why your pitch deck should be treated like a product—and why rapid iteration matters more than perfection.Discover how to find and leverage early believers who can champion your raise.Understand why you can’t (and shouldn’t) try to please every investor.Recognize that rejections will never stop stinging—and how to keep going anyway.Decode why some investors say they can’t invest and what that really means.Get strategies for overcoming the embarrassment of asking for money, especially from people you know.Hear how macro trends like the IPO drought ripple down to impact early-stage funding.Whether you’re a first-time founder or a seasoned operator gearing up for another raise, this episode will give you a candid, practical roadmap for navigating the messy art of securing early capital.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 appSubscribe 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 followingKey linksGet 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 YanivWork 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-mcarthurIntro Voice: Jeremiah Owyang https://web-strategist.com/

11 Elo 50min

In the startup world, speed is everything.  But too many founders confuse busyness with velocity, mistaking frantic activity for real momentum.In this episode, Chris and Yaniv are joined by Keith Lucas, former product and engineering leader at Roblox, to unpack what speed actually means—and how to build it into your startup from day one.They explore why alignment, culture, and cadence matter more than hustle, and how Keith's “Inspire, Align, Amplify” framework can unlock lasting execution velocity.In this episode, you will:Understand why "busyness" is a dangerous red herring that kills real progressLearn how to define speed as strategic value delivered to users, not activityExplore how culture acts as the "fat tires" that enable rapid startup momentumApply Keith’s "Inspire, Align, Amplify" framework to build cohesive, fast-moving teamsIdentify common founder traps, from toxic niceness to decision paralysisDesign company values that actually shape behaviorDiscover why realized culture drives execution speedThe 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 appSubscribe 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 followingKey linksGet 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 YanivWork 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-mcarthurIntro Voice: Jeremiah Owyang https://web-strategist.com/

4 Elo 56min

Is GitHub Spark the future of AI software building? Startups looking to use “vibe coding” often face janky tools and broken promises. Microsoft's latest IDE, however, has serious potential to be the industry breakthrough that addresses the agonizing issues developers face.In this episode, Chris Saad and Yaniv Bernstein unpack Microsoft’s latest attempt to win back developer mindshare with the launch of GitHub Spark, a cloud-based, AI-enhanced IDE. They debate whether Spark is an MVP for building micro-apps or a Trojan horse for a more ambitious plan to dominate developer workflows.Plus, the hosts dive into Trump’s executive order on “woke AI,” Coinbase’s bold relaunch of Base as a social platform, and YouTube’s machine-learning age verification for teens.In this episode, you will:Explore what GitHub Spark is and why it matters for the future of AI-powered software developmentUnderstand Microsoft’s positioning strategy and why it might be hiding bigger ambitionsCompare Spark to tools like Cursor, Claude Code, and WindsurfLearn how Trump’s executive order frames “neutral AI” and why it’s likely political theaterAssess whether Coinbase’s “Base App” is crypto’s answer to YouTube and TwitterDiscover the implications of YouTube’s new AI-based teen detection systemDebate the real risks and rewards of AI regulation and social media safetyThe 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 appSubscribe 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 followingKey linksGet 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 YanivWork 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-mcarthurIntro Voice: Jeremiah Owyang https://web-strategist.com/

31 Heinä 54min

AI is changing how we build startups, but how can founders leverage it without their product becoming slop?Too many early-stage entrepreneurs believe that faster prototyping automatically leads to better products. In reality, rushing to “ship something” can destroy product-market fit before it’s even tested.In this Q&A episode, Yaniv Bernstein (ex-Google, ex-Airtasker) and Chris Saad (former Head of Product at Uber) answer your burning questions about startup strategy, from hiring and product design to breaking industry rules. They reveal how to separate real innovation from AI-washing and why “contrarian and right” is the only strategy that works.In this episode:Discover which AI-adjacent startup opportunities are attracting real investor interest (and which ones to avoid)Learn how to rethink your MVP strategy in an AI-powered world without falling into the “build fast, fail fast” trapUnderstand when and how to break conventional startup rules to gain a genuine competitive edgeAvoid the most common hiring mistakes founders make, including the “warm body” trap and hiring the wrong senior execsIdentify the difference between a great product manager and a glorified project manager (and when to hire one)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 appSubscribe 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 followingKey linksGet 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 YanivWork 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-mcarthurIntro Voice: Jeremiah Owyang https://web-strategist.com/

28 Heinä 39min

Is Uber’s gamble on RoboTaxis a brilliant move, or the end of its asset-light magic? And what’s really going on inside OpenAI as it races to dominate AI?Many founders assume hypergrowth companies are perfectly coordinated machines, but the reality is far messier. From billion-dollar GPU costs to chaotic product launches, there’s a lot for entrepreneurs to learn from how these giants operate.Chris Saad and Yaniv Bernstein break down Uber’s 20,000-car RoboTaxi deal with Lucid and Nuro, and delve into what it means for the future of ride-hailing. They also discuss OpenAI’s new ChatGPT Agent, the company’s internal culture, and why GPU costs might be the most important factor shaping the AI race.In this episode:Understand why Uber is moving away from its asset-light model to own RoboTaxisDiscover how Uber plans to compete with Waymo, Tesla, and other autonomous vehicle playersLearn the economics of hybrid fleets—and why surge pricing is still criticalUnpack OpenAI’s confusing product lineup and what it reveals about their cultureEvaluate why GPU costs dominate OpenAI’s strategic decisionsExplore the risks of AI agents acting autonomously—and why reliability is still a huge issueTake away lessons founders can apply when scaling teams and managing chaotic hypergrowthThe 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 appSubscribe 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 followingKey linksGet 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 YanivWork 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-mcarthurIntro Voice: Jeremiah Owyang https://web-strategist.com/

24 Heinä 48min

Getting noticed is harder than ever, but Rajiv Ayyangar (CEO, Product Hunt) says most startups fail for a surprisingly simple reason: lack of clarity and velocity.In this episode of The Startup Podcast, Rajiv explains what separates breakout startups from the thousands that never gain traction. Drawing on insights from hundreds of Product Hunt launches, Rajiv shares how to craft a tagline that resonates, why launching early (and often) is critical, and how velocity builds a powerful feedback flywheel that accelerates growth.He also shares what Product Hunt’s biggest winners did differently, why clarity forces better product thinking, and how AI tools are changing the speed of iteration, giving today’s founders a unique advantage if they use them correctly.In this episode:Learn why clarity beats hype every timeHow to craft a tagline that drives viral tractionWhy velocity builds trust and better user feedbackThe power of launching early (and re-launching often)Lessons from Notion, Superbase & other Product Hunt standoutsWhether you’re planning your first launch or trying to reignite growth, this conversation is packed with actionable lessons for founders who want to stand out.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 appSubscribe 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 followingKey linksGet 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 YanivWork 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-mcarthurIntro Voice: Jeremiah Owyang https://web-strategist.com/

21 Heinä 57min