The Startup Podcast

Ashley Smith, General Partner at Vermilion Cliffs and former marketing leader at Twilio and GitHub, shares invaluable insights for pre-seed founders. She emphasizes the importance of direct customer conversations over investor playbooks. The discussion highlights how successful companies built community engagement to drive growth. Smith advocates for hiring generalists and treating product and marketing as a unified front. Plus, she encourages founders to embrace rejection and craft authentic content in a saturated digital landscape.

Google’s long-running antitrust case has reached its remedy stage, and the outcome was far lighter than many expected. No breakup, no ban on default search deals, just a few constraints on bundling apps and some required data sharing, but it may not be quite as simple as it seems on the surface.Meanwhile, OpenAI dropped $1.1 billion to acquire Statsig, a product analytics company. What are the details of the deal, and what does it reveal about the future of OpenAI?To top the week off, Y Combinator released its Fall 2025 Request for Startups, and the lineup is surprisingly AI-heavy. Is this really a good indicator of successful startups, or are YC missing the mark with this one? Chris and Yaniv discuss this at length, cutting deeply into why these criteria were chosen, what you should (and shouldn’t) listen to, and where founders can looking for investors instead.In this episode, you will:Understand why Google’s “light touch” antitrust remedies sent its stock up 8% overnightLearn what OpenAI’s Statsig acquisition signals about its long-term strategyExplore why YC’s latest startup requests are so heavily AI-focused, and why that’s a mistakeCompare today’s antitrust rulings with the Microsoft case of the 1990sDiscover how AI may disrupt not just tech, but also government consulting and enterprise softwareGet Yaniv’s insider view on why intent-driven marketplaces may be the next frontierThe 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/

Dive into the world of startup accelerators and discover their critical role in helping early-stage companies thrive. Learn about the unique benefits they offer, from mentorship to funding, and the significance of events like Demo Day. Hear firsthand insights from an entrepreneur who navigated Y Combinator during the pandemic, highlighting both challenges and valuable lessons. Finally, explore essential factors to consider when choosing the right accelerator for your startup journey.

Is Apple’s dominance in smartphones starting to crack? Google’s Pixel 10 launch brought AI-first features, polished hardware, and bold marketing, signaling a new era in the iPhone vs. Android rivalry.For years, the iPhone has been synonymous with polish, hardware quality, and ecosystem lock-in. But with Google’s patient, decade-long investment in the Pixel line, coupled with deep AI integration, the balance may be shifting.Today, Chris and Yaniv analyze Pixel 10’s hardware updates, AI-powered OS features, and how Google’s persistence has brought it head-to-head with Apple. For founders and entrepreneurs, they also offer their unique insight into startups and unpack what you can learn about patience, platform strategy, and design in the middle of a platform shift.In this episode, you will:Understand how Google turned Pixel from a reference device into a competitive product lineExplore why AI-first design is becoming the true battlefield in smartphonesSee how proactive AI (Magic Q, contextual responses, Gemini integration) could reshape user experiencesDiscover why patience and iteration are critical lessons for startup foundersApply insights from platform ecosystems (reference apps, open source, and monetization strategies) to your own businessThe 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/

What makes a great tech infrastructure startup? And how do the best ones successfully navigate, and stand out from, the overcrowded market?In this episode, Yaniv is joined by Joseph Ruscio, General Partner at Heavybit and former CTO of Vibrato, to unpack the dos and don'ts of tech infrastructure startups, how open source fuels growth, and why AI is changing the way software is built.With over 20 years in system software and a portfolio including LaunchDarkly, Netlify, and PagerDuty, Joe brings a front-row perspective to the future of startup building. The conversation dives into bottom-up growth, developer adoption, and the open source strategies that give founders leverage—and how AI agents are reshaping the role of the software engineer.In this episode, you will:Understand why bottom-up adoption often beats enterprise sales for startup growthLearn how AWS scaled from startups to Fortune 500s—and what founders can copyDiscover the power of open source as a go-to-market strategy (and its pitfalls)See why giving away your product can actually accelerate growth and community adoptionExplore how AI is changing developer workflows and the future role of engineersIdentify the risks of being “too close to your own pain” as a technical founderApply practical guidelines for choosing your startup’s tech stack without overthinkingDevGuild Open Source: http://heavybit.com/devguild/open-source 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/

Is the AI hype cycle about to burst?For months, investors and founders have chased sky-high valuations, billion-dollar hires, and promises of superintelligence, but Meta's drastic plans to cut back its AI division seem to indicate a bleak future for LLMs and AI at large.In this episode, Chris and Yaniv unpack the latest shakeup at Meta, using their knowledge and experience in Silicon Valley to analyze the situation and pick apart whether this is a canary in a coal mine. They explore why Meta is restructuring, what it says about the state of large language models (LLMs), and how to navigate high-stakes moments when the hype cycle turns.In this episode, you will:Understand what Meta’s latest AI restructure really signals about industry prioritiesLearn why hype cycles always lead to a trough of disillusionment, and how to prepareExplore how trillion-dollar bets on AGI could reshape competitive dynamicsSee why founders should question assumptions about LLM productivity gainsRecognize the risks of chasing hype versus building sustainable business modelsThe 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/UCNjm1MTdjysRRV07fSf0yGgGive 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/

This new era of AI-driven startups has many founders still believing success is about having the perfect product roadmap. The truth, however, is far more counterintuitive.In this episode, Yaniv and Chris dive into timeless lessons from Paul Graham’s legendary essay “Startups in 13 Sentences”. Drawing from Graham’s wisdom and their own experiences, they break down why co-founders matter more than ideas, why “launch fast” is the golden rule, and why understanding users is harder (and more important) than chasing growth.In this episode, you will:Learn why choosing the right co-founder is the most important decision you’ll ever makeUnderstand why launching fast is less about speed and more about learning from real usersDiscover why evolving your idea matters more than defending a perfect planSee how understanding users drives sustainable growth (and why chasing vanity metrics kills startups)Explore why great customer service that 'doesn’t scale' is actually a secret weaponUnpack the dangers of measuring the wrong things and how to track what truly mattersFind out why distractions (even profitable ones) are the silent killers of young startupsFor founders serious about building in the AI era, these lessons, though written 16 years ago, are more relevant than ever. Startups succeed not by following conventional wisdom, but by mastering the counterintuitive truths that define Silicon Valley’s greatest companies.Read Paul Graham's "Startups in 13 Sentences" here: https://paulgraham.com/13sentences.html 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/

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/

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/

In violation of long-standing internet norms like robots.txt, Cloudflare caught Perplexity AI scraping content from websites that had explicitly opted out. The situation begs the question: what happens when AI startups prioritize growth over digital consent?Listen as Chris and Yaniv discuss the repercussions of Cloudflare's "honeypot" traps. They also dig into Wikipedia’s launch of a fast-track deletion policy to counter the overwhelming number of low-effort, AI-generated articles, and consider whether Amazon's AWS is falling behind cloud rivals like Google, Microsoft, and Oracle.In this episode, you will:Understand why Cloudflare accused Perplexity AI of ignoring internet normsLearn how robots.txt and internet trust are being undermined by AI crawlersExplore whether “move fast and break things” still applies in the AI eraDiscover how Wikipedia is fighting back against a flood of AI-generated slopDebate the moral vs. legal boundaries of disruptive startup behaviorHear why AWS may be falling behind Google, Microsoft, and even OracleExamine what makes a wartime vs. peacetime CEO in the AI cloud raceConsider whether AI is eating its own tail by destroying its data sourcesThe 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/