The Startup Podcast

Hosted by Yaniv Bernstein and Chris Saad

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Aug 2026

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About the show

Advice for founders and entrepreneurs who want to build disruptive startups like they do in Silicon Valley. Not another interview podcast: concrete tips and masterclasses on what founders need to know: raising Venture Capital, strategy, product, marketing, growth, and more. A guide to the unique mindset and approach that drives Silicon Valley style disruption. Hosts Chris Saad and Yaniv Bernstein share practical advice based on decades of experience at Google, Uber, and their own startups.

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August 3, 2026Episode 2646 min

ScaleStudio: The new tool putting our principles into practice

After nearly 300 episodes of The Startup Podcast, Chris Saad is bringing everything he's learned about building world-class products and product strategy into a single tool: ScaleStudio. In what may be our final episode (unless a white knight sponsor appears), Chris walks Yaniv through the product that could fundamentally change how founders approach strategy; from problem statement all the way to positioning, roadmap sequencing, and org design. Chris demonstrates how this one AI tool, housing his vast knowledge of Silicon Valley startup strategy, can give an overwhelming process a navigable structure, allowing founders to plot a deliberate course through the chaos. In this episode, you will: Discover how Scale Studio turns Chris's 30 years of product strategy expertise into an AI tool that guides you from problem statement through to roadmap and positioning See the complete strategy development workflow in action: from mapping all possible problem domains and solutions, to building the org structure required to execute Learn why mapping the entire solution space upfront prevents the "thrash" that derails most startups when customer requests pull the team in conflicting directions Understand the customer terrain framework that reveals which customer segments are easy wins and which are death traps, allowing you to carve the narrowest viable wedge into your market See how Scale Studio integrates with your development workflow through exports and MCP connections, turning high-level strategy into actionable execution roadmaps Explore how AI can now handle the heavy lifting of strategy generation and iteration in around an hour, while keeping guardrails in place to maintain quality and coherence across every section Timestamps 00:14 On Today's Show: The Last Startup Podcast? 01:39 Turning Our Advice Into A Product (ScaleStudio) 03:18 Homepage And Templates 04:40 Problem Statement 05:36 Copilot And Collaboration 08:10 Solutions And Editing 09:49 'How It Works' Stage 11:22 Building Strategy From Seed 13:32 Mapping The Solution Space 18:53 Customer Segments and Personas 20:46 Wedges And Customer Terrain 23:07 Customer Roadmap View 26:32 Org Design 28:03 How Does AI Change Hiring? 31:18 Roadmap To Unlocking Cohorts 33:51 Market Sizing 37:25 Planning the Future of ScaleStudio… in ScaleStudio? 39:08 The Future of Agentic Orgs 42:11 Closing Thoughts: 4 Years of TSP Resources mentioned in this episode ScaleStudio (Chris’s AI-powered product strategy tool): https://scalestudio.io/ Vera (Yaniv's Startup): https://vera.guide 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 Secure your official TSP merchandise at https://shop.tsp.show/ Follow us on YouTube for full video episodes: https://www.youtube.com/@startup-podcast Give us a public shout-out on LinkedIn or anywhere you have a social media following Key links This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar. 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/

July 27, 2026Episode 2552 min

Rob Snyder demonstrates his PULL framework in real-time – using Yaniv's startup

A few weeks ago, Rob Snyder came on the pod to introduce his PULL framework for identifying real product-market fit. Now, Yaniv turns the tables and subjects his own startup, Vera, to the same scrutiny. Yaniv and Rob strip away the noise around Vera's mission to help adult children care for aging parents and get brutally honest about where the product actually has pull, where it doesn't, and what needs to change immediately. They identify a specific, unavoidable moment in the customer journey and pinpoint that is where the real business begins, and discuss more macro issues, such as AI vs. human expertise, founder blind spots, and more. In this episode, you will: Understand the difference between an aspiration and a project, and why this distinction is vital for PULL Learn how the PULL framework cuts through startup theory to identify the exact moment when customers will actually pull your product from your hands, before they have to wait for a crisis Discover why Vera's original problem was too abstract, and how narrowing to a specific market segment with intense, unavoidable need becomes your path to revenue and growth Hear the truth behind what really pushes your customers to adopt earlier: reality does the convincing, not your marketing Understand the challenge of reputation in AI: how do human-shaped applications build trust the way human experts do? Timestamps 00:00 Coming Up 01:38 On Today's Show: Yaniv Applies PULL to Vera 04:42 Defining PULL and Projects 05:54 Vera's Customer Goals 08:00 Unavoidable Moments and Crisis 11:25 Real Users and Traction 16:58 Mission vs Push Marketing 24:07 Why Isn't Google Enough? 28:21 Nailing the Specific Project 34:02 Testing Market With Ads 37:06 Bill Gates And AI Shift 38:47 Human Shaped Software Design 43:45 Trust And Reputation In Bots 48:48 About The Book Resources mentioned in this episode The Power of Pull by Rob Snyder: https://www.amazon.com/Power-Pull-Customer-Successful-Founders/dp/1541705955 Rob Snyder's website: https://www.robsnyder.org Vera (Yaniv's startup helping families care for aging parents): https://vera.guide Club Sandwich, Vera's podcast and community for the sandwich generation: https://clubsandwich.community What the sandwich generation is (and why it's Vera's market): https://clubsandwich.community/sandwich-generation 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 Secure your official TSP merchandise at https://shop.tsp.show/ Follow us on YouTube for full video episodes: https://www.youtube.com/@startup-podcast Give us a public shout-out on LinkedIn or anywhere you have a social media following Key links This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean and memorable name, go to https://⁠get.tech/tsp This episode of 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 ⁠⁠⁠⁠ https://⁠www.vanta.com/tsp⁠⁠⁠⁠⁠ 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/

July 20, 2026Episode 2443 min

Why you should run your startup like a poker player (Replay)

This is a remastered Replay of one of our most popular episodes, "What Startups Can Learn From Poker", which was originally published on 21 December 2022. Enjoy! Original description: All season, Chris and Yaniv have talked about the mindset that is needed to succeed at venture-backed startups. For the final episode of Season 1, we tie it all together with an analogy: tournament poker. It is amazing how many things poker and startups have in common, so in this episode we use the lens of poker to discuss the big picture of how to approach building a successful startup. We dive into each of the following commonalities between poker and startup life: 01:56 Playing an iterative game 10:00 Burning cash 13:31 Making decisions based on uncertain information 18:46 Progressive learning 28:44 Avoiding 'resulting' 35:02 The relatively low probability of a successful outcome (and why that’s OK!) This episode was inspired by the book 'Thinking in Bets' by former pro poker player Annie Duke. 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 Secure your official TSP merchandise at https://shop.tsp.show/ Follow us on YouTube for full video episodes: @startup-podcast Give us a public shout-out on LinkedIn or anywhere you have a social media following Key links This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean and memorable name, go to https://⁠get.tech/tsp 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/ #TheStartupPodcast #startups #poker #texasholdem #investment #venturecapital #resulting #probability #ChrisSaad #YanivBernstein

July 13, 2026Episode 2456 min

Avoiding ‘team debt’ by building small and smart (w/ Matt Cook)

Is hiring a person still your default answer to a problem? For a growing number of startups, it shouldn't be. In this episode, Yaniv Bernstein is joined by returning guest Matt Cook, co-founder of Scouut, one of Australia's most respected engineering recruiters for early-stage startups, to unpack what's changed in engineering hiring since Matt's last visit. They cover ‘team debt’ (the AI-era sequel to tech debt), why AI is acting as an appetite suppressant for headcount, why the best engineers are now worth $400K+, and why the ‘software factory builder’ is becoming the most sought-after hire in tech. In this episode, you will: Understand "team debt", and why teams built to solve today's problems are already becoming obsolete Learn why "removing the crutch" (like scrapping a QA gating function) forces the kind of AI-native change that timid, incremental adjustments never will Discover why most startups were already overstaffed before AI, and why AI now acts as an ‘appetite suppressant’ for hiring rather than just an efficiency tool Hear why hiring should now be treated as a last resort, and what that actually means in practice for founders Understand why compensation banding and headcount-based budgeting are breaking down, and what smart companies are replacing them with Learn about the rise of the ‘software factory builder’: the rare, highly-paid engineer who uses their judgment to build airtight, AI-based infrastructure the rest of the team can lean on Timestamps 00:00 Coming Up... 00:58 On Today's Show: Matt Cook on 'Team Debt' 02:36 What is Team Debt? 05:12 Refocusing on AI Native Solutions 10:40 Unlearning Old Hiring Ladders 12:04 Why Companies Are Oversized 14:59 AI, the 'Corporate Ozempic' 19:25 Layoffs and Team Composition 24:02 Disrupting Yourself at Series B 28:12 The Salary Race for AI Engineers 34:01 Limitations of Headcount Budgeting 38:16 How Downsizing Can Help You Grow 41:13 ClickUp's 'Hail Mary' Pivot 44:26 Software Factory Builders and 'Forward Deployed' Automation 49:14 Maintaining Safe Internal Software 54:25 Closing Thoughts Resources mentioned Scouut (Matt Cook's engineering recruitment firm for early-stage startups): https://scouut.com.au/ Matt Cook on LinkedIn: https://www.linkedin.com/in/matthewmarkcook/ 'Corporate Ozempic' by Scott Galloway — the essay behind the AI/hiring analogy Yaniv references: https://www.profgalloway.com/corporate-ozempic/ 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 Secure your official TSP merchandise at https://shop.tsp.show/ Follow us on YouTube for full video episodes: https://www.youtube.com/@startup-podcast Give us a public shout-out on LinkedIn or anywhere you have a social media following Key links This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean and memorable name, go to https://⁠get.tech/tsp This episode of 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 ⁠⁠⁠⁠ https://⁠www.vanta.com/tsp⁠⁠⁠⁠⁠ 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/

July 6, 2026Episode 2255 min

How good timing makes great products w/ Paul Orlando

Every startup pitch deck has a "why now" slide. Most of them are nonsense, barely considered, and only there to tick a box. But timing is more than a slide, it can make or break a company. It’s the difference between pets.com and the trillion-dollar company selling the exact same idea a decade later. In this episode, Yaniv Bernstein sits down with Paul Orlando, who has built four startup accelerators supporting over 300 companies, including Hong Kong's first accelerator and a program in Rome run in partnership with the Vatican, and has taught entrepreneurship at USC for over a decade, where he also runs one of LA's largest startup incubators. Paul has spent years obsessing over a single question: why do some ideas succeed while near-identical ones fail years earlier? The answer became his book, ‘Why Now? How Good Timing Makes Great Products.’ In this episode, you will: Learn Paul's framework of timing drivers, and the five that show up again and again: technology, social/behavioral change, regulation, installed base, and crisis Walk through the YouTube case study in detail to see how broadband penetration, digital camera adoption, and falling storage costs converged to make 2005 the right year, after the identical idea failed less than a decade earlier Discover why first-mover advantage is much narrower than founders assume, and the two specific conditions (locking in customers, locking out competitors) required for it to actually work Get a framework for balancing founder agency against timing, because you can't will your way into good timing, but you also can't wait passively for the perfect moment to arrive Timestamps 00:00 Coming Up... 01:04 On Today's Show: Why Timing Matters 01:44 Guest Intro: Paul Orlando 02:42 Is 'Why Now' Predictable? 05:40 Paul's Timing Drivers Framework 08:44 Case Study: YouTube's Market Timing 11:47 Business Model Shifts 15:16 Case Study: Pets.com Unit Economics 22:16 Case Study: AI Vibe Coding 24:11 What Are 'Sleeping Beauty' Startups? 27:46 Incorporating AI into Timing Drivers 28:52 Collapse of Build Costs 33:34 Case Study: Vera and Unit Economics of Voice 35:15 False 'Why Now' Risks 37:46 First Mover Reality 40:33 Reid Hoffman on Blitzscaling 41:49 Case Study: AT&T's Picturephone and Mobile Telephony 46:31 Lessons on Failure and Agency 54:09 Closing Thoughts Resources mentioned 'Why Now?: How Good Timing Makes Great Products' by Paul Orlando: https://www.amazon.com/Why-Now-Timing-Makes-Products/dp/B0CYXSNMT3 Paul's website, Startups Unplugged: https://startupsunplugged.com Paul on LinkedIn: https://www.linkedin.com/in/porlando Paul on X/Twitter: https://twitter.com/porlando 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 Secure your official TSP merchandise at https://shop.tsp.show/ Follow us 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 of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar. 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/

June 29, 2026Episode 2153 min

Make your product irresistible: Rob Snyder on the PULL framework

You’ve done all the research, implemented every startup strategy you could find, but your product just isn’t selling. Where do you start looking for the problem? And how do you identify and implement the solution? In this episode, Yaniv Bernstein sits down with Rob Snyder – serial founder, fellow at Harvard Innovation Labs, operating partner on the venture side, and now author of 'The Power of PULL' – to discuss why most founders have fundamentally misunderstood demand, and how to accurately pinpoint it. In this episode, you will: Understand why pain points and problems alone are not demand, and why customers can have them indefinitely without ever buying anything Learn the PULL framework (Project, Unavoidable, List of options, Limitations): the four conditions that must all be present before a customer will rip a product out of your hands Hear how startup Ruby went from 10 nodding sales calls with no closes to rapid growth, simply by identifying the specific moment when their ICP's project became truly unavoidable Get Rob's two-step pull-based sales script: how to get a prospect to monologue their own pull framework back at you, and how to pitch in a way that fits their world rather than your vision Timestamps 00:00 Coming Up... 00:51 On Today's Show: Rob Snyder on When Sales Works 03:24 Why 'Demand' Is More Than Pain 05:51 What Are Other Frameworks Missing? 12:36 'Vitamins vs. Painkillers' 16:12 What is the PULL Framework?21:07 Case Study: Data Migration (Ruby) 26:04 Case Study: Fundraising (Campground) 29:11 Where Interviews Go Wrong 35:19 Practice Exercise: Rob Sells Yaniv The Book 40:14 Debrief: Why Listening Wins 42:48 How to Spot Real Buying Signals 43:58 Reverse Engineering Fast Deals 47:58 Founder Mindset and Sanity 50:54 Closing Thoughts: "Get Out Of The Building" Resources in this episode The Power of Pull by Rob Snyder: https://www.amazon.com/Power-Pull-Customer-Successful-Founders/dp/1541705955 Rob's website: https://www.robsnyder.org Rob on LinkedIn: https://www.linkedin.com/in/rsnyder1 Rob's Substack, 'The Physics of Startups': https://thephysicsofstartups.substack.com Eric Ries's TSP episode: https://youtu.be/HQ7cP1lGyiM April Dunford's TSP episode: https://youtu.be/QC4cKxlW81s Mark Roberge's TSP episode (also discusses product-market fit): https://youtu.be/j_UeeEn7p9o 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 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 of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean and memorable name, go to https://⁠get.tech/tsp This episode of 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 ⁠⁠⁠⁠https://⁠www.vanta.com/tsp⁠⁠⁠⁠⁠ 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/

June 22, 2026Episode 2054 min

Success is 90% luck. So how do you build a successful startup? (w/ Mike Grossman)

Founders are told that if they work hard, build the right product and hire well, the outcome will follow. It's motivating. It's clean. And according to today's guest, it's mostly wrong. Mike Grossman has been CEO of six venture-backed Silicon Valley companies. Across them, he tried 18 different business models. Twelve failed. Five required layoffs. Three lived in persistent existential crisis. And yet all six were eventually acquired. Mike's story is one that far more founders actually live, but almost nobody tells. In this episode, Yaniv Bernstein sits down with Mike to dig into his new book, Failure Is An Option: a candid 44-essay collection drawn from three decades in the trenches. They explore the uncomfortable truth that luck dominates outcomes more than skill, why your business model is not your business, and how radical honesty is the most underrated leadership tool in a founder's kit. In this episode, you will: Learn about 'resulting': why confusing luck for skill costs founders in both directions Hear how Mike pivoted Tempo from building a Visa/Mastercard competitor to partnering with Mastercard, only to have the entire model wiped out overnight by a Senate amendment Discover the 'dreamers vs soldiers' framework for building teams that hold together when adversity strikes Hear Mike's hard-won playbook for layoffs: why founders almost always cut too little, too late; what day two feels like; and why a smaller, denser team is often more productive Get a clear framework for staying accountable for the process when the outcomes aren't in your control Timestamps: 00:00 Coming Up... 00:34 On Today's Show: Mike Grossman on Managing Failure 02:02 The Role of Luck and Timing 03:41 Poker Strategy and 'Resulting' 08:55 "The Business Model Is Not The Business" 11:27 Tempo's Pivot 13:28 Why Values Matter In A Crisis 19:21 Talent Density and Layoffs: Cut Once, Cut Deep 28:15 How AI Changes Hiring Pace 32:15 Leading with 'Radical Honesty' 36:33 Dreamers vs. Soldiers 38:02 Managing Investors 41:43 Luck, Agency, Process 48:39 About 'Failure Is An Option' 51:29 Closing Thoughts Resources mentioned 'Failure Is An Option' by Mike Grossman: https://www.failureisanoption.com Mike Grossman's Substack: https://failureisanoption.substack.com Thinking in Bets by Annie Duke (the 'resulting' concept discussed): https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216355 'Incorruptible' by Eric Ries: https://www.incorruptible.co/ Eric Ries's TSP episode: https://youtu.be/HQ7cP1lGyiM 'Powerful' by Patty McCord: https://www.amazon.com/Powerful-Building-Culture-Freedom-Responsibility/dp/1939714095 Patty McCord's TSP episode: https://www.youtube.com/watch?v=BefnNLBEmXA The Durbin Amendment (the legislation that killed Tempo): https://en.wikipedia.org/wiki/Durbin_amendment 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 Secure your official TSP merchandise at https://shop.tsp.show/ Follow us here on YouTube for full-video episodes: https://www.youtube.com/@startup-podcast Give us a public shout-out on LinkedIn or anywhere you have a social media following Key links This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar. 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/

June 16, 2026Episode 1952 min

Insiders React: Anthropic’s Fable, Mythos explained + SpaceX’s record-breaking IPO

The Startup Podcast is back for its 300th episode – and it’s an absolute doozy. In today’s Reacts, hosts Chris Saad and Yaniv Bernstein break down how Anthropic became the new industry leader in AI, and why betting on coding as the 'meta domain' of AI turned out to be one of the most consequential product decisions of the decade. They also dig into Mythos and the newly released Claude Fable: what makes Fable different, whether it has something approaching genuine intelligence, and what the Anthropic 'strategy dividend' (per Ben Thompson of Stratechery) actually means for the industry. Then: SpaceX’s record-breaking IPO. With a reported valuation of around $1.88 trillion and a prospectus that talks more about AI than rockets, Chris and Yaniv ask the obvious question: is it worth it? In this episode: How product discipline and a bet on coding put Anthropic in front Strategy dividends: how Anthropic's genuine commitment to safety became both a real constraint and a powerful marketing asset at the same time Claude’s new models, Fable and Mythos: what's actually changed? Why Chris thinks the SpaceX IPO at ~90x revenue is a roll-up of Elon Musk's 'dead bodies' Liquidity risk: with SpaceX, Google and Anthropic all raising simultaneously, is there enough liquidity in the market? Timestamps 00:00 Coming Up... 00:39 On Today's Show: Chris returns, Anthropic’s Mythos/Fable, SpaceX IPO 02:30 Anthropic surges ahead of OpenAI 04:16 Why coding is a 'meta-advantage' for AI 07:24 OpenAI’s product turmoil 11:04 Are OpenAI competing with Anthropic, or Google? 13:25 Anthropic’s enterprise strategy 17:06 Mythos: ‘Safety marketing’ or ‘safety dividends’? 23:24 Are Anthropic the good guys? 26:32 Fable: “Mythos with a muzzle” 28:29 Does AI only need to beat the average human? 31:23 Yaniv’s experiences with Fable 32:46 Reasoning logs and self-correction 34:27 Is SpaceX over-valued? (Yes.) 39:32 SpaceX’s moats and growth potential 43:02 Why ‘second mover advantage’ sometimes wins 46:05 Will there be a crash? Chris predicts a liquiditycrunch 50:31 Closing Thoughts Resources mentioned in this episode Dario Amodei's essay, 'Machines of Loving Grace': https://darioamodei.com/machines-of-loving-grace Ben Thompson's Stratechery: https://stratechery.com Project Glasswing (Anthropic's restricted Mythos access program): https://www.anthropic.com/glasswing Eric Ries on The Startup Podcast: https://youtu.be/HQ7cP1lGyiM 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 Secure your official TSP merchandise at https://shop.tsp.show/ Follow us on YouTube for full video episodes: https://www.youtube.com/@startup-podcast Give us a public shout-out on LinkedIn or anywhere you have a social media following Key links This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar. This episode of 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 ⁠⁠⁠⁠ https://⁠www.vanta.com/tsp⁠⁠⁠⁠⁠ 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/

June 8, 2026Episode 1842 min

How to fix a 'broken industry' (w/ Brandon Weber – Nava Benefits, VTS, Hightower)

Every founder gets a version of the same advice: don't pick a fight with an entrenched industry. The incumbents have the relationships, the regulatory cover, the deep pockets - you'll bleed out trying. But some of the most interesting companies of the last decade were built ignoring that advice, winning over markets that were nearly impenetrable. In this episode, Yaniv Bernstein is joined by Brandon Weber - co-founder and CEO of Nava Benefits, a Series C-funded AI-powered health benefits brokerage. Before Nava, Brandon co-founded Hightower, a commercial real estate startup that merged with VTS and went on to run over half of all office buildings in the United States. Brandon has now done this twice in two completely different industries, and has developed a repeatable playbook for breaking into entrenched markets and using AI as a structural advantage. Yaniv and Brandon dig into what actually makes a market 'broken', why the entry point needs to be far narrower than most founders think, and how to build the conviction to keep going when a thousand people tell you it won't work. In this episode, you will: Understand the 'burning platform' signal - what makes a market 'broken', but worth spending a years breaking into Learn why your entry point needs to be far narrower than feels comfortable, and how Brandon went from targeting 'the health insurance market' to 'employers with 50-500 employees who can't afford a dedicated benefits team' Hear why 'disrupting from within' is often smarter than disrupting head-on - and how Nava built a broker-shaped entity that the industry's immune system couldn't reject Discover how to design a human-AI system (what Brandon calls a 'cybernetic' service model) where agents handle 80-85% of the work and licensed professionals operate at the top of their license Timestamps 00:00 Coming Up… 00:45 On Today's Show: Brandon Weber on Fixing Broken Industries 01:43 How To Spot Broken Markets 03:59 Why Most Healthcare Startups Fail (Distribution) 05:35 Lessons From Building Hightower and VTS 08:41 How Do We Think Smaller? Finding the 'Narrow Wedge' 10:57 What It Means To 'Disrupt From Within' 16:53 Choosing the ICP 18:35 The Innovator's Dilemma and Moving Upmarket 22:57 Scaling with AI: A Business in Two Phases 26:29 Service as a Software 34:02 Attract and Hire Industry Insiders 36:44 When to Acquire 39:06 Closing Advice Resources mentioned in this episode Nava Benefits (Brandon's company): https://www.navabenefits.com Gary Lo's previous TSP episode: https://youtu.be/jtMgd7Nv_HY The Innovator's Dilemma by Clayton Christensen (framework discussed at length): https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244 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 Secure your official TSP merchandise at https://shop.tsp.show/ Follow us on YouTube for full-video episodes: https://www.youtube.com/@startup-podcast Give us a public shout-out on LinkedIn or anywhere you have a social media following Key links This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar. 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/

June 1, 2026Episode 1752 min

Why Gary Lo's product strategy has evolved in the era of DIY software

What if writing software became as easy as taking a selfie? This episode, Yaniv Bernstein sits down with Gary Lo - founder of OpenBA and one of the sharpest AI-and-startups thinkers Yaniv knows - to discuss the concept of 'selfie software': disposable, hyper-personal, AI-generated tools that anyone can create for themselves, with no hand-written code. AI-generated tools like these are changing the startup landscape. While founders now have more tools at their disposal, it's now necessary than ever to create a product that truly disrupts the market. Gary and Yaniv discuss all of this and more, likening Claude and ChatGPT to Windows and Mac, and exploring what this tech landscape means if you're building a software startup today. In this episode, you will: Understand the 'selfie software' concept: why AI is making software disposable, personal, and low-stakes, and what that means for the market you're building in Learn why AI platforms are forcing startups to rethink whether they should build on their own infrastructure or embed into Claude and ChatGPT instead Hear Gary's 'burn it down' exercise: how to identify which parts of your product are genuinely defensible, and which will simply catch fire in the next AI wave Understand why software engineering isn't dead, but the problems worth solving with it have fundamentally shifted Timestamps 00:00 Coming Up... 01:09 On Today's Show: Gary Lo on 'Selfie Software' 02:48 About Gary 03:16 How 'Hyper-Personalized' AI Is Like Photography 05:36 Gary's Real Estate Workflow (OpenBA) 07:29 Defining 'Selfie Software': Why Custom Tools Win 10:33 So... Is It Bad Software? 13:29 'Can’t You Just Add This One Thing...' 15:30 When Personalization Becomes Bloat 17:42 Working In-App with Anthropic and OpenAI APIs 20:29 Token Economics and Moats 25:28 Microsoft's Lessons in Platform Power 30:27 But What If Anthropic Comes For My Vertical? 32:48 How Open Source Keeps AI in Check 35:18 Unlearning and Rebuilding 39:05 Gary's 'Burn It Down' Test 44:01 Is Software Engineering Dead? (No.) 50:17 Closing Thoughts Resources in this episode Gary Lo's previous TSP episode (on OpenClaw and Claude Cowork): https://youtu.be/V3YFghiy8p0 Garry Tan's gstack: https://github.com/garrytan/gstack Andrej Karpathy on Software 2.0: https://karpathy.medium.com/software-2-0-a64152b37c35 Vera (Yaniv's startup, AI-supported guidance for people caring for ageing parents): https://vera.guide 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 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 of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar. This episode of 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 ⁠⁠⁠⁠ https://⁠www.vanta.com/tsp⁠⁠⁠⁠⁠ 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 Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/ Intro Voice: Jeremiah Owyang https://web-strategist.com/