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TitreDateDurée
ScaleStudio: The new tool putting our principles into practice03 Aug 202600:46:03

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



The Pact

Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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/


Rob Snyder demonstrates his PULL framework in real-time – using Yaniv's startup27 Jul 202600:52:03

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

    • 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:



    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/


    Why you should run your startup like a poker player (Replay)20 Jul 202600:43:38

    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

    Avoiding ‘team debt’ by building small and smart (w/ Matt Cook)13 Jul 202600:56:20

    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


    The Pact

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:


    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/


    How good timing makes great products w/ Paul Orlando06 Jul 202600:55:56

    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


    The Pact

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:


    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/


    Make your product irresistible: Rob Snyder on the PULL framework29 Jun 202600:53:55

    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/

    Success is 90% luck. So how do you build a successful startup? (w/ Mike Grossman)22 Jun 202600:54:35

    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

    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/

    Insiders React: Anthropic’s Fable, Mythos explained + SpaceX’s record-breaking IPO16 Jun 202600:52:15

    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/

    How to fix a 'broken industry' (w/ Brandon Weber – Nava Benefits, VTS, Hightower)08 Jun 202600:42:33

    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/


    Why Gary Lo's product strategy has evolved in the era of DIY software01 Jun 202600:52:40

    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

    The Pact

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

    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/


    Author Eric Ries (The Lean Startup) on how to build an incorruptible company25 May 202600:57:05

    Most founders set out to build something that matters: a company that’s aligned with their mission, now and forever. But what if the very systems we use to build ‘real’ companies are the thing that corrupts them?


    In this episode, Yaniv Bernstein is joined by Silicon Valley legend Eric Ries author of the era-defining 'The Lean Startup', founder of the Long-Term Stock Exchange, and now the author of a provocative new book, 'Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great'.


    Eric makes the case that corruption is a structural problem, rather than a failing of the people themselves. He walks Yaniv through the ‘financial gravity’ that pulls good companies away from their founders' purpose, and the governance ‘fortresses’ that a small handful of outlier companies (from Costco to Novo Nordisk to Anthropic) have used to stay great.


    In this episode, you will:

    • Understand ‘financial gravity’ - the force that degrades values, corrupts economic decisions, and reduces long-term outcomes

    • Learn the legend of Sol Price (the father of modern retail behind Costco), and why treating margins as a liability rather than a virtue can be a source of enduring strength

    • Explore the ‘industrial foundation’ model behind century-old giants like Novo Nordisk and Zeiss, and why companies with this structure are roughly 6x more likely to survive to year 50

    • Hear how Anthropic's Long-Term Benefit Trust shaped its trajectory, and why in the age of AI, trustworthiness is the single most valuable corporate asset


    Timestamps

    00:00 Coming Up...

    01:06 On Today's Show: Eric Ries, author of The Lean Startup and Incorruptible

    02:41 From 'The Lean Startup' to 'Incorruptible': Why Governance Matters

    04:13 The Two Mysteries

    05:45 Case Study: Sol Price and FedMart

    08:58 The Shareholder Primacy Trap

    14:04 Costco's Governance Fortress

    16:50 Founder Control vs VCs

    19:33 Why Markets Punish Your Mission

    21:30 Novo Nordisk's Foundation Model

    26:35 Anthropic and AI Trust

    29:37 Governance in Action Today

    31:54 Doing the Right Thing

    33:27 Goodhart's Law and Customer Service Metrics

    38:36 Why 'Harder Is Easier'

    39:02 Costco's Hotdog Promise

    41:55 Mission Lock Structures

    43:32 Pitching Investors, Leverage and the Fundraising Decision Tree

    49:33 HBO's Silicon Valley and 'Minimum Viable Product'

    53:57 Closing Thoughts & Book Plug


    Resources mentioned in this episode

    • 'Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great' by Eric Ries: https://www.incorruptible.co/

    • 'The Lean Startup' by Eric Ries: https://theleanstartup.com/book

    • Long-Term Stock Exchange (LTSE): https://ltse.com/

    • 'Skin in the Game' by Nassim Nicholas Taleb: https://www.amazon.com/Skin-Game-Hidden-Asymmetries-Daily/dp/0425284646

    • Mark Cuban's Cost Plus Drugs: https://costplusdrugs.com/


    The Pact

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

    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/


    FEED DROP: Could AI Make Capitalism Better? Henrik Werdelin Is Optimistic (from FAFO with Dan Blumberg)21 May 202600:39:02

    This is a bonus feed drop from Dan Blumberg's podcast 'Future Around and Find Out' (FAFO), winner of the 2026 Webby Award for Best Technology Podcast.


    If you like what you hear, check out FAFO at https://www.futurearound.com/


    Original description:

    Henrik Werdelin is one of my favorite entrepreneurs. He’s founded and incubated several unicorns, most notably BARK, the dog happiness company.


    Henrik himself is a pretty happy guy — an optimistic guy who likes to ask what could go right? — and on the day we recorded (a few months ago as I was squirreling away interviews for the podcast relaunch), he helped me see through some future of tech gloom I was feeling. I honestly can’t even remember what Trump+tech hellscape we were living through that week, but I do remember that Henrik put me in a better mood. I think he’ll do the same for you, no matter how you’re feeling. 🤗


    Henrik believes AI could be a massive force for good. That it could bring forth a whole new — a better! — form of capitalism. He writes about this is in his latest book, Me, My Customer, and AI. He points to those (like Henry Ford) who took advantage of electricity by making drastic, not incremental, changes to how the build things. Our conversation pairs nicely with my recent episode with Azeem Azhar, who said the AI winners will “come from odd places”, as they have in previous tech transformations.


    Here’s more of what Henrik and I cover:

    • His concept of "relationship capital"—the moat AI can't clone—and why the companies that win next will be defined by who they serve, not what they make
    • The three components of relationship capital: intensity, community, and durability
    • The "it sucks that" method for finding problems worth solving (he took it to a fifth grade class; the teacher was not thrilled)
    • His vision for the "headless", agentic web, where your startup's MVP is a group of agents, not an app
    • The wildly practical AI tools he's built just for himself: a custom CRM that searches by vibes not names, a newsletter bot tuned to his quarterly goals, and an agent that handled his visa paperwork while he was in a meeting
    • Why entrepreneurial skills—agency, narrative, resourcefulness—are the ultimate career insurance, whether you start a company or not
    • The absolutely ridiculous story of how a prank on a cruise ship led to him meeting his BARK co-founder in a heart-shaped bed

    Chapters

    • (01:43) - Two Futures: AI Bad vs. AI Really, Really Good
    • (05:44) - Why Positivity Is Actually the Riskier Bet
    • (09:05) - Electricity, AI, and the Rise of Relationship Capital
    • (11:12) - The Three Components of Relationship Capital
    • (14:20) - "It Sucks That" — The Best Way to Find a Real Problem
    • (19:22) - The Headless Future and Minimum Viable Agents
    • (22:40) - N-of-One Software: Building Tools Just for Yourself
    • (26:48) - Henrik's Custom Newsletter Bot and AI-Powered CRM
    • (30:59) - Warp, Obsidian, and Letting Agents Loose on Your Computer
    • (34:45) - Entrepreneurial Skills as Career Insurance
    • (36:53) - The Heart-Shaped Bed: How Henrik Met His BARK Co-Founder


    Credits for The Startup Podcast:

    • 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/
    The Science of Scaling: Using data to scale your startup perfectly w/ Mark Roberge18 May 202601:05:03

    Most founders treat 'scale' like a switch you flip after raising a round: hire 14 reps, 10x the ad spend, and pray. About half scale too early and burn the runway, while the other half scale too late and get caught by a more aggressive competitor. Almost nobody can tell you, in measurable terms, when they're actually ready.

    In this episode, Yaniv Bernstein is joined by Mark Roberge - founding CRO at HubSpot (where he scaled the company from $0 to $100M ARR), senior lecturer at Harvard Business School, cofounder of Stage 2 Capital, and author of the new book 'The Science of Scaling'.

    Mark walks Yaniv through his impressive data-driven framework for scaling that he's spent a decade refining, covering how to objectively define product-market fit, why customer retention is the only honest measure of PMF, and how to instrument a Leading Indicator of Retention you can act on in week one.


    In this episode, you will:

    • Learn why retention is the only honest measure of product-market fit, and why most founders are flying blind without it

    • Discover Mark's framework for building a Leading Indicator of Retention (LIR) you can measure in week one, using Slack, HubSpot, and Facebook as worked examples

    • Hear Mark coach Yaniv through Vera's LIR in real time, and pick up a repeatable method for designing one for your own business

    • Learn the 'Stay/Go/Slow' model for pacing hires and spend post-raise, and why startups should reassess monthly or quarterly rather than locking in an annual plan

    • Get Mark's take on why 'paranoid optimism' is the trait that correlates most strongly with founder success, and the link between that trait and founder mental health


    Timestamps

    00:00 Coming Up

    00:26 On Today's Show: The Science of Scaling

    01:47 Guest Intro: Mark Roberge

    02:31 Why Scaling Needs Data

    04:20 Eric Ries and Product Market Fit

    06:56 Retention as a North Star

    10:15 What Makes a Good Leading Indicator?

    15:00 Case Study: Vera (Yaniv's Startup)

    17:41 Choosing Frequency and Event

    23:55 Instrumenting and Unique Value

    31:12 Blitzscaling and Defining PET

    34:41 ICP Denominator Rules

    37:28 Segmenting By Product

    40:40 Go To Market Fit

    45:25 Dealing with Revenue-Focused Investor Pressure

    50:33 The Pace of Scaling

    56:07 About the Book, The Science of Scaling

    57:45 Founder Mental Health

    01:02:28 Closing Thoughts


    Resources in this episode:

    • Mark Roberge on LinkedIn: https://www.linkedin.com/in/markroberge/

    • ‘The Science of Scaling: Using Data to Decide When — and How Fast — to Scale Revenue’ by Mark Roberge: https://www.amazon.com/Science-Scaling-Revenue-Mark-Roberge/dp/1394319428

    • Stage 2 Capital (Mark's B2B SaaS-focused venture firm): https://www.stage2.capital/

    • 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


    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/

    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/

    Refounding: Why this $80m founder quit as CEO, and what it says about the future of startups11 May 202600:45:17

    In 2026, startups age like milk. Josh Foreman's solution is a radical one - step down as CEO, go back to basics, and refound the whole company. 


    Yaniv Bernstein discusses this decision with Josh, founder and (for now) CEO of InDebted - the AI-native debt resolution business he scaled to an $80M revenue run rate, a Series C raise, and operations across 8 markets. Just days before recording, Josh publicly announced he's hiring a new CEO so he can step back into the business as a hands-on operator and refound the company for the agentic AI era.


    In this conversation, Josh and Yaniv discuss 'refounding' in practice, what it takes to rebuild the company's processes from the ground up, and why technical founders who don't go back on the tools right now are setting themselves up to be outbuilt by a smaller, faster, leaner version of themselves.


    In this episode, you will:

    • Learn why Josh believes the highest-leverage role for a technical founder in 2026 is no longer CEO, and how to structure a founder-CEO partnership that actually works

    • Understand why 'feature patching' an established business is a losing strategy, and what it really means to rebuild your company function-by-function from a clean slate

    • Discover how revenue-per-employee has become the metric that matters most when raising capital and competing with AI-native upstarts

    • Hear why services-as-software and performance-fee models are suddenly the bull case for investors who hated them 12 months ago - and why the SaaS seat fee is on the way out

    • Find out what it looks like to unbundle your product into agent-ready primitives, and why owning the eval for a narrow domain may be a bigger moat than your full-stack UI


    Timestamps

    00:00 Coming Up: Refounding

    00:41 Josh Foreman, CEO (for now)

    01:41 What Refounding Means

    04:53 Rebuilding the Factory

    07:38 Bringing the Team Along

    10:51 No Choice but Change

    14:56 Aligning the Board and Investors

    16:52 Putting Founders Back on the Tools

    26:24 'Corporate Ozempic' Shrinking Teams

    32:57 Unbundling and Products for Agents

    38:39 Hiring a CEO When Refounding

    44:11 Closing Thoughts



    Mentioned in this episode


    The Pact

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:


    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/


    Adapting your startup to an AI-native world (w/ Marlon Nichols)04 May 202600:38:15

    Many AI startups funded in the last 18 months won't last three years - so what makes a business durable today?


    Yaniv Bernstein is joined by Marlon Nichols, co-founder and managing general partner of MaC Venture Capital - one of the most active seed-stage AI investors in the market, having scaled MaC to over $600M AUM across three funds in just four years. Marlon's portfolio includes Pipe, Stoke Space, Thrive Market, Chef Robotics, and exits like Wonder Dynamics to Autodesk and Gimlet Media to Spotify.


    In this conversation, Marlon uses his industry experience to explain the biggest threats to new AI startups, and what the key components of successful startups in the industry will be.


    In this episode, you will:

    • Hear why Marlon thinks niche or mid-size foundational models are now prime acquisition targets for OpenAI

    • Discover why misreading traction is the #1 mistake VCs are making right now

    • Learn why Marlon is more excited about manufacturing-line prediction and grid-scale batteries than humanoid robots

    • Explore why founder unit economics need a complete rewrite when token costs replace SaaS-style marginal cost

    • Understand why software is no longer a moat — and why data access, deep customer integration, and speed are the only three durable advantages left at the application layer

    • Learn the difference between AI-native companies and AI-bolted-on companies, and what a 5-year-old startup should do if it's on the wrong side of that line


    Timestamps

    00:00 Coming Up

    01:07 On Today's Show: Durable Tech

    02:33 Meet Marlon Nichols

    03:25 Defining 'Durable' AI Startups

    05:23 Moats for Foundation Models

    07:15 Chef Robotics and AI Native vs AI Enabled

    09:24 Upgrading Legacy Startups

    10:55 Pipe’s AI Pivot Case Study

    13:19 Winning at the App Layer

    15:56 Speed and Workflow Stickiness

    17:51 Investment Checklist and Team

    20:30 Automotive Digital Twins and Regulatory Testing

    24:27 Why Physical AI?

    26:09 Robotics In Manufacturing

    26:55 Energy Storage And Batteries

    28:30 Why Cheaper Builds Still Need Talent

    30:19 Where Traction Can Be Misleading

    33:41 Token Costs And Unit Economics

    36:46 Closing Thoughts


    Mentioned in this episode


    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: 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/

    How the best founders balance fear and hope27 Apr 202600:29:27

    Being a founder has always meant dreaming big while keeping a close eye on potential trip-ups, and in the age of AI, finding and maintaining that balance is more important than ever.


    Today, Yaniv Bernstein talks about the importance of getting that balance right. Using deep insight and decades of industry experience, he discusses why now is the time for founders to be more ambitious than ever before - while identifying threats to success and keeping a keen, near-paranoid eye on them.


    In this episode, you will:

    • Understand why ‘paranoid optimism’ has always been the founder superpower, and why AI has made it more essential than ever
    • Learn why tokens are ‘the new oil’ and how the ‘token OPEC’ is already exerting price and product leverage over every AI-native startup
    • Explore Garry Tan's ‘boil the lake’ concept and why early-stage founders can now afford to be more ambitious in scope than ever before
    • Find out why startups have a bigger speed advantage over incumbents than at any time in history, and how to actually use it
    • Discover how foundation model providers like Anthropic, OpenAI, and Google can wipe out entire startup categories without ever deliberately competing with you



    Timestamps

    00:00 Coming Up

    00:59 On Today's Show: Paranoid Optimism

    01:27 Surviving as a Baby Turtle

    03:00 Risks of Pure Optimism

    05:24 A Herd of Thundering Elephants

    07:44 Magic Elephants

    09:50 3 Shifts: Compression, Leverage and Startup Advantage

    12:54 YC's Garry Tan & 'Boiling The Lake'

    15:38 Why Be Paranoid?

    15:52 AI Risks Category Collapse

    18:13 Anthropic, Google and OpenAI: The OPEC of Tokens

    19:51 Identity Collapse

    21:54 How to Operate As Paranoid Optimist

    21:59 1. Holding Strong Priors and Updating Fast

    23:31 2. Architecting For Escape

    25:57 3. Stay Closer To The Problem Than The Solution

    28:13 Closing Thoughts



    Resources mentioned in this episode

    • 'Same As Ever' by Morgan Housel: https://www.amazon.com/Same-Ever-Guide-Never-Changes/dp/0593332709
    • Last week’s episode - Same As Ever: 7 rules that HAVEN'T changed about building great startups (w/ Amir Shevat): https://www.tsp.show/same-as-ever-7-rules-that-havent-changed-about-building-great-startups-w-amir-shevat/
    • Previous episode - 'Unlearning' with Yaniv: Why founders need to rewrite outdated, radioactive mindsets: https://www.tsp.show/unlearning-with-yaniv-why-founders-need-to-rewrite-outdated-radioactive-mindsets/
    • Garry Tan’s 'Boil the Ocean' blog post: https://garryslist.org/posts/boil-the-ocean
    • Vera, Yaniv's current 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 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.

    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/

    Same As Ever: 7 rules that HAVEN'T changed about building great startups (w/ Amir Shevat)20 Apr 202600:49:52

    Between AI shaking up the industry, geopolitical upheaval, and unpredictable capital, being a founder has never been more confusing.


    So what advice, if any, is still relevant?


    In this episode, Yaniv Bernstein is joined by Amir Shevat (Silicon Valley developer platform veteran and now General Partner at Darkmode Ventures) to answer exactly that. Focusing on what isn't changing rather than what is, Amir walks through seven truths of startup building that have become more important in the age of AI.



    In this episode, you will:

    • Discover why AI-generated sales outreach is backfiring, and why authenticity, proof of effort, and in-person events are becoming the gold standard
    • Explore the "founder tar pit" of bad markets, and the simple questions that reveal whether yours is one to run from
    • Learn why design in 2026 is about putting positive interactions and emotions first, and how to prioritize these effectively


    Timestamps

    00:00 Coming Up…

    01:07 Guest Intro: Amir Shevat

    02:36 On Today's Show: 7 Timeless Truths

    04:34 Jeff Bezos and the 'Same As Ever' Mindset

    08:19 Rule 1. Hire The Right Team

    10:15 How AI Raises The Bar

    14:26 Rule 2. A Delightful User Experience

    16:27 Conversational Interfaces

    18:07 Why You Should Design For Emotions

    24:20 Rule 3. Hustle Still Wins

    26:05 The Return of Authentic Selling

    28:09 Landing Your First Customers

    28:50 Rule 4. Build Real Moats

    30:48 Mongol Hordes: Is 'Execution Speed' A Moat?

    33:00 'Thick' Product Advantage

    33:39 Rule 5. Vision Beats TAM

    38:07 Rule 6. Choose Great Markets

    42:34 Rule 7. Build An Unfair Advantage

    47:10 Recap and Closing Thoughts



    Resources in this episode:

    • Darkmode Ventures (Amir's early-stage fund): https://www.darkmode.vc/
    • Amir Shevat on LinkedIn: https://www.linkedin.com/in/amirshevat/
    • Designing Bots: https://www.oreilly.com/library/view/designing-bots/9781491974810/
    • Working Backwards by Colin Bryar and Bill Carr: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595
    • Same as Ever by Morgan Housel: https://www.amazon.com/Same-Ever-Guide-Never-Changes/dp/0593332709
    • 2012 re:Invent Day 2: https://www.youtube.com/watch?v=O4MtQGRIIuA


    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 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



    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

    Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    Surviving the AI SaaSpocalypse: Will AI kill your startup? w/ Scotty Allen13 Apr 202600:47:52

    Will AI kill your startup? For a lot of startups, probably yes.

    But which ones? And more importantly, how do you make sure yours isn't one of them?


    Yaniv Bernstein is joined by returning guest Scotty Allen (bootstrapper, founder of The Product Bus, and startup strategist extraordinaire) to reason through one of the most pressing questions of 2026: how do you build a startup to survive the SaaSpocalypse?


    They discuss why this AI wave is more of a threat to tech startups than Google and Facebook ever were, and why the B2B/B2C distinction has never mattered more.

    Along the way, Yaniv discusses why making your software 'headless' will be a key survival strategy, and the pair explore what it means to build products that cater to agents.


    In this episode, you will:

    • Learn why the best B2B SaaS strategy is to strip the UI and invest everything in defensible, thick capability that agents want to use
    • Hear why the B2B/B2C split has sharpened dramatically, and why deep user empathy and design remain incredibly important
    • Find out what "agentic engine optimisation" means, and why creating an agent-centric tool could be your most powerful growth channel
    • Understand why your tolerance for ambiguity may be the single most important skill you can develop as a founder right now


    Timestamps

    00:00 Coming Up…

    00:54 On Today's Show: Will AI Kill Startups?

    01:32 Is This Different to Google/Facebook?

    05:15 The Threat to 'MD-able' SaaS

    10:49 Headless SaaS Advantage

    15:19 Thin and Thick Wrappers

    18:19 Bottom Up Disruption

    20:34 Platform Fragility Risks

    22:22 When DIY Systems Backfire

    24:46 B2B vs B2C Distinction

    28:53 Tools Agents Prefer

    30:56 Claude 'Skills' As Distribution

    32:05 Platforms Are Dead

    34:09 Tool Use As An Inflection Point

    35:42 Managing Agents Like Staff

    38:55 B2B Headless vs. B2C Design

    41:48 Who Pays In B2C?

    44:10 Why Vera Is A 'Guide', Not An Agent

    45:39 Embrace Ambiguity And Build

    46:30 Closing Thoughts


    Resources mentioned in this episode:

    • The Product Bus (Scotty Allen's startup validation and product strategy firm): https://theproductbus.com/
    • Scotty Allen on LinkedIn: https://www.linkedin.com/in/thescottyallen/
    • The Bootstraps Podcast (Scotty's own podcast, 'Straight Up From Scratch'): https://thebootstrap.tech/
    • 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

    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 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.


    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

    Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    #SaaS #SaaSpocalypse #Startups #TechStartups #Founder #TechBusiness #TheStartupPodcast

    ‘Unlearning’ with Yaniv: Why founders need to rewrite outdated, radioactive mindsets06 Apr 202600:29:28

    You may have spent years (or even decades) building your expertise. But is any of it still relevant? And how much of it is an active detriment to your startup?


    In this special solo episode, Yaniv Bernstein delivers a no-guest monologue on the most critical skill any founder can develop right now: ‘unlearning’. Drawing on Morgan Housel's ‘Same as Ever’; real-world examples from his own startup, Vera; and frameworks for rebuilding beliefs from the ground up, Yaniv makes the case that obsolete knowledge is as bad as radioactive waste actively distorting your decisions.


    In this episode, you will:

    • Understand why AI is making the half-life of expertise shorter than ever before
    • Learn how the sunk cost fallacy stops founders from discarding knowledge that’s causing more harm than good
    • Discover why the identities you've built around your craft ("I am a programmer", "I am a copywriter") may be the single biggest barrier to adapting in 2026
    • Find out what skills are actually worth holding onto, and how to combine them with the meta-skill of rapid adaptation
    • Learn three practical mental models for unlearning: belief audits, first principles thinking, and systems thinking



    Timestamps:

    00:00 Coming Up

    00:42 On Today's Show: Unlearning

    02:03 Morgan Hausel's Same as Ever

    04:13 When Knowledge Turns Toxic

    07:00 What Unlearning Means

    07:42 Why Unlearning Is Hard

    08:32 Sunk Cost Fallacy

    12:32 Identity Threat

    17:17 Redefining Expertise

    18:15 Meta Skills For Experts

    21:55 Auditing Your Beliefs

    24:14 First Principles Thinking

    25:21 Systems Thinking

    27:24 You Should: Make Time To Adapt

    28:14 You Should: Embrace Discomfort

    29:01 Closing Thoughts



    Resources mentioned in this episode:

    • 'Same as Ever: A Guide to What Never Changes' by Morgan Housel — the book Yaniv references throughout this episode on timeless principles of human behavior: https://www.amazon.com/Same-Ever-Guide-Never-Changes/dp/0593332709
    • Naval Ravikant on identity — Yaniv attributes the idea of being cautious about taking on identities to Naval. Naval's writing and podcast appearances are a good starting point: https://nav.al



    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 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.


    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/


    #unlearning #psychology #Startups #TechStartups #Founder #TechBusiness #TheStartupPodcast

    Your co-founder relationship could break your startup! Here's how to fix it30 Mar 202600:22:46

    (This is Part 2 of a conversation with Dr. Matthew Jones about co-founder relationships. You can find Part 1 here: https://www.tsp.show/how-to-identify-red-flags-early-in-your-cofounder-relationship-w-dr-matthew-jones/)


    Co-founder conflict is tough to deal with, but it also has ripple effects through your entire organization. When a tough relationship is left to fester, it can erode your team culture, spike turnover, and eventually turn into a full-blown crisis.


    Continuing last week's conversation with Yaniv, Dr. Matthew Jones - author of The Cofounder Effect and founder of Cofounder Clarity - walks you through actionable ways to repair a flailing co-founder relationship.


    From identifying and avoiding common mistakes, to finding good coaching, Dr. Jones brings valuable insights that will ensure you and your founding team thrive together.


    In this episode, you will:

    • Understand how co-founder dysfunction ripples through your organization, driving up employee churn and instability.

    • Learn why most companies are in dire need of a 'co-founder date'.

    • Discover why avoiding relationship repair makes the problem more difficult to deal with over time.

    • Explore the Three Languages Framework, and how to use it to diagnose where your co-founder communication is breaking down.

    • Learn why working on the 1–2% of bandwidth that goes to your co-founder relationship is actually the highest-ROI investment you can make as a founding team.


    Chapters00:00 Coming Up...00:41 On Today's Show: Co-founder Relationships, Part 201:17 Ripple Effects on Company Culture04:15 Stats on Employee Stress And Churn05:28 Co-founder Syncs and Co-founder Dates09:33 Using 'The Cofounder Effect' to Navigate Conflict10:30 Enduring Discomfort12:28 Co-founder Coaching: 'Couples Therapy For Founders'?16:18 Why Self-Work Is 'High Leverage'17:44 Today's Action: Use The Three Languages Framework19:48 'Nonviolent Communication' and Naming The Elephant In The Room22:20 Closing Thoughts and Resources


    Resources mentioned in this episode:


    The Pact 

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:


    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.


    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/


    How to identify red flags early in your cofounder relationship w/ Dr. Matthew Jones23 Mar 202600:39:58

    Your co-founder relationship is the single most important variable in your startup's success, and one of the most likely things to destroy it.


    Today, Yaniv Bernstein sits down with Dr. Matthew Jones, author of ‘The Cofounder Effect’ and founder of Cofounder Clarity, to dig into the psychology of co-founder relationships: why they break down and what the warning signs look like.


    Matt brings a rare combination of clinical depth and startup-world pragmatism to the topic - an essential skillset to help you properly understand common co-founder pitfalls, and how to avoid them.

     

    In this episode, you will:

    • Learn what 'negative sentiment override' is, why it's the tipping point in a deteriorating co-founder relationship, and how to catch it before it takes hold.

    • Discover how the co-founder relationship is structurally different from a marriage, and why that means you have to deliberately repair and reconnect with your co-founder.

    • Hear why power dynamics in founding teams are almost always present and are often more destructive when left unnamed.

    • Find out why being able to navigate conflict is more important than finding the 'right' co-founder pairing.

    • Understand the risks of identity fusion with your startup, and why professional distance is a feature rather than a weakness.

    • Learn why co-founder agreements need to evolve over time, and what a healthy renegotiation looks like.

    • Explore the unique dynamics of three- and four-person founding teams, including the coalition patterns that tend to emerge and why they're so destructive.

    Resources mentioned in this episode:

    • Dr. Matthew Jones’ website, Cofounder Clarity (his coaching practice): https://www.cofounderclarity.com

    • ‘The Founder's Dilemmas’ by Noam Wasserman: https://www.amazon.com/Founders-Dilemmas-Anticipating-Princeton-Entrepreneurship/dp/0691158304

    • 'Knowing This Data Will Make You A Better Fundraiser', the TSP episode with Carta's Head of Insights, Peter Walker: https://open.spotify.com/episode/7aI9NeIVZ7JqkSH2OsizBF

    • The Gottman Institute - the research behind 'negative sentiment override' discussed in this episode: https://www.gottman.com

    • Dr. Matthew Jones on LinkedIn: https://www.linkedin.com/in/dr-matthew-jones-7a832a37/ 

    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 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


    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/

    Why Claude never stops listening to our meetings (w/ Minikai's Keoki Alexander-Chang)16 Mar 202600:41:57

    In a deeply regulated industry such as healthcare, building an AI-native app poses a host of unique challenges, particularly when it comes to navigating customer privacy and industry red tape. How do you create an industry-leading resource and stay on the cutting edge of tech, while managing these constraints?


    Keoki Alexander-Chang can help you there. He's the founder and CEO of Minikai, a Melbourne-based startup using AI agents to slash the administrative burden on disability and aged care providers. Before launching Minikai, he led Deloitte's Forensic AI lab, so he's been thinking about applied AI in complex, regulated environments for far longer than most founders.


    In this episode, Yaniv sits down with Keoki to explore what it really means to build a person-centred AI product in a high-stakes regulated sector — and how Minikai applies that same AI-native mindset to their internal operations, through fine-grained access control, human-in-the-loop design, and AI agents keeping the entire sales pipeline up to date in the background.



    In this episode, you will:

    • Learn how to design agentic AI products for high-stakes regulated environments
    • Understand the importance of intentionally including fine-grained access control, provenance and adding friction to the process in order to keep humans in the loop
    • Make sense of the fundamental shift within the build vs. buy equation, and why Minikai is questioning every SaaS tool in their stack
    • Find out why Keoki treats his product like a garden, and why pruning is just as important as growing
    • Understand what "person-centred AI" actually means in the disability and aged care context
    • Hear how Minikai's team now uses continuously running AI agents to keep their entire HubSpot pipeline up to date
    • Learn about the story of the lapel mics: how Minikai is condensing the entire workflow from meeting to working code, skipping Jira entirely



    Resources mentioned in this episode

    • Minikai (Keoki's startup: AI agents for disability and aged care providers): https://www.minikai.com/
    • Keoki Alexander-Chang on LinkedIn: https://www.linkedin.com/in/keokichang/
    • DJI Mic (the lapel mic Keoki's team uses to capture all meeting audio for Claude): https://www.dji.com/mic
    • Insiders React: How OpenClaw and Claude Cowork changed Gary Lo's approach to startups (the companion TSP episode referenced by Yaniv): https://www.tsp.show/insiders-react-how-openclaw-and-claude-cowork-changed-gary-los-approach-to-startups-w-gary-lo-op/



    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 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.


    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/


    Recruiting the best AI engineers w/ Matt Cook of Scouut09 Mar 202600:57:19

    Has your hiring process kept up with the industry’s AI leaps, or are you still interviewing like it's 2022?


    Today’s AI-driven landscape means the skill gap between a good engineer and a great one widens every day, and the great ones can be difficult to find. But how do you choose – and hire – the best in the business?

    How do you find those elusive engineers who can skilfully handle multi-agent workflows, ship in hours what used to take weeks, and add an AI-focused competitive edge to your startup?


    In this episode, Chris Saad and Yaniv Bernstein are joined by Matt Cook, an expert in hiring the best engineers in the business, and co-founder of Scouut – one of Australia's most respected engineering recruiters for early-stage startups.

    Matt works with pre-seed through to Series C companies and has a front-row seat to how AI is reshaping what ‘great’ looks like in engineering, and how founders and hiring teams alike can keep pace.


    They cover what's fundamentally changed in engineering hiring, what hasn't, and how to build a small, elite team that punches well above its weight.


    In this episode, you will:

    • Understand why AI is widening the gap between great and average engineers
    • Discover the three questions to ask any Big Tech candidate to determine if they'll thrive in a startup
    • Find out why much more is expected of ‘senior’ engineers, and what that means for founders
    • Hear how the best startups are now testing for AI competency in interviews, not just coding ability
    • Learn why smaller teams, higher salaries, and generous token budgets are the new arbitrage for attracting elite engineers
    • Understand why you should be designing the role for the people you want, and making your AI-forward culture clearly visible


    Resources mentioned in this episode

    • 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/
    • Loki (Australian startup referenced for their public AI-first hiring stance): https://www.itsloki.com/
    • Solid (lightweight vibe-coding tool mentioned by Chris): https://trysolid.com/


    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 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


    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/

    Insiders React: OpenClaw and Claude Cowork have changed everything for startups w/ Gary Lo, Open BA02 Mar 202600:37:26

    The agentic AI revolution is finally escaping the coding bubble. What does that mean for startup founders?


    Just 13 days after recording his first conversation with Yaniv, Gary Lo called to re-record. The reason? OpenClaw and Claude Cowork dropped some huge AI agent updates, and it shifted Gary's perspective enough to change the whole conversation.


    In this episode, Yaniv Bernstein sits down with Gary Lo – founder of OpenBA, one of Australia's most compelling pre-seed AI startups – to unpack why OpenClaw and Claude Cowork news marks a 'Cursor moment' for the rest of the world: the inflection point where AI stops being a productivity tool for tech teams and starts fundamentally reshaping how every industry works.


    They break down why tool use will make LLMs genuinely transformative, why non-technical business owners are already buying Mac Minis to run AI agents, and what the shift from 'human-first' to 'LLM-first' product design means for how you build and position your startup today.

    This episode is essential listening for any founder trying to figure out where to place their bets in an agentic world.


    In this episode, you'll learn:

    • Why OpenClaw and Claude Cowork signal a 'Cursor moment' beyond software engineering
    • How tool use transforms LLM weaknesses into strengths
    • Why the long-promised vision of "everything as an API" is finally becoming real
    • How to think about building for agents vs. humans, and why most current tools aren't optimized for either
    • The "done list" mental model: how agentic coding is collapsing the coordination layers in software workflows
    • Why being "a tool worth calling" – like Supabase – is a smarter bet than competing directly with AI models
    • How Gary is applying LLM-first thinking to OpenBA's roadmap right now


    Resources mentioned in this episode:

    • OpenClaw: https://openclaw.ai/
    • Claude Cowork (Anthropic's agentic desktop tool): https://www.anthropic.com/news/claude-cowork
    • Cursor (AI-native code editor, referenced as the original 'Cursor moment' for coding): https://www.cursor.com
    • Supabase (referenced as an example of a tool that rides the agentic AI wave): https://supabase.com
    • OpenBA (Gary Lo's startup - AI platform for buyer's agents): https://openba.com.au
    • Gary Lo on LinkedIn: https://www.linkedin.com/in/gary-lo-engineer/


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    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.


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    Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    Making the most of the founder/investor dynamic (w/ Liz Zalman, author of 'Founder vs Investor')23 Feb 202600:57:41

    Founders and investors like to tell themselves they're on the same team, and they can be – but it takes work.


    In this episode, Yaniv Bernstein sits down with Liz Zalman, a veteran founder with over 20 years of startup experience, for an in-depth chat about the real dynamics of the founder-investor relationship. Liz is also co-author (alongside VC Jerry Neumann) of 'Founder Vs Investor: The Honest Truth About Venture Capital from Startup to IPO’, one of Yaniv's favorite books on startups.


    From re-vesting demands to acquisition offers that investors won't approve, Liz brings hard-won, unfiltered perspective to some of the most uncomfortable moments a founder will face.


    In this episode, you will:

    • Understand what re-vesting actually is, and the smartest way to respond when investors ask for it.
    • Learn why taking a single dollar of venture capital puts you on a specific, irreversible path.
    • Discover how to negotiate a term sheet from a position of strength, even when you're exhausted and desperate to close.
    • Find out when and how founders can take money off the table – and why most quality investors support founders to have stability in their personal finances.
    • Learn how Liz stress-tests potential investors while negotiating terms.
    • Understand the real difference between valuation and control.
    • Hear why listening is the single most underrated skill in a founder's toolkit.


    Resources mentioned in this episode

    • Founder vs. Investor (book) by Elizabeth Zalman & Jerry Neumann, the book discussed throughout this episode: https://www.foundervsinvestor.com
    • Venture Deals by Brad Feld & Jason Mendelson, referenced by Yaniv as "the bible of venture capital": https://www.venturedeals.com
    • Sandgarden, Liz's current startup: https://www.sandgarden.com
    • Liz Zalman on LinkedIn: https://www.linkedin.com/in/elizabethzalman


    The Pact

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    Key links

    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


    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 favourite registrar.


    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/#Investors #Startups #TechStartups #Founder #TechBusiness #TheStartupPodcast

    How founders can survive 2026 w/ Jess Mah16 Feb 202600:55:56

    Is AI making founders more anxious than ever, even in the heart of Silicon Valley? Behind the optimistic LinkedIn posts and fundraising announcements, some of the most successful people in tech are struggling with burnout and an overwhelming pace of change. So what does it actually take to build a resilient, successful startup in 2026?


    In this episode, Yaniv is joined by Jess Mah, serial founder, Y Combinator alum, and venture creation powerhouse behind Mahway. Jess has founded more than 10 companies — collectively valued at over $1 billion — and was the youngest woman ever accepted into Y Combinator.

    Fresh from dinners with Fortune 500 CEOs and unicorn founders in San Francisco, she shares what's really happening behind closed doors in the startup world, and why the founders who refuse to get hands-on with AI tools are now at a serious disadvantage.


    In this episode, you will:

    • Discover why experienced, repeat founders are at the highest risk of falling behind in the AI era
    • Learn Jess's go-to interview question that instantly reveals whether a hire will stay relevant
    • Understand "role collapse", and what should replace traditional siloed positions when the boundaries between product managers, designers, and engineers break down
    • Hear why the best founders in 2026 are building clickable prototypes themselves instead of delegating to product teams
    • Find out why AI has made distribution and competitive moats harder, not easier, and what to do about it
    • Explore why domain expertise has become the most valuable startup superpower when building is cheap
    • Get an honest look at the anxiety, burnout, and 996 culture affecting even the top AI founders in the Bay Area
    • Learn the AI educators and resources Jess and Yaniv personally rely on to stay ahead


    Connect with Jess: https://www.linkedin.com/in/jessmah/Resources mentioned in this episode:

    • Stratechery by Ben Thompson: https://stratechery.com/
    • Matthew Berman (YouTube): https://www.youtube.com/@matthew_berman
    • How I AI with Claire Vo: https://www.lennysnewsletter.com/s/how-i-ai
    • Steve Yegge / Gastown: https://www.linkedin.com/in/steveyegge/
    • Maven (cohort-based learning): https://maven.com/
    • Hacker News: https://news.ycombinator.com/



    The Pact

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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    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


    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/


    Recursive Self-Determination: Why your startup needs autonomy at every layer09 Feb 202600:44:19

    Self-determination throughout your team: it sounds simple, but implementing it effectively could give your startup a razor-sharp competitive edge.

    In this episode, Chris and Yaniv unpack the 'Recursive Principle of Self-Determination', a framework for designing autonomous startups that maximize agency at every layer of the business. They explore how high-agency decisions shape product strategy, engineering, go-to-market, fundraising, teams, and culture, and why AI is accelerating the shift toward founder empowerment.


    In this episode, you will:

    * Understand the concept of recursive self-determination and why it applies across the entire startup stack

    * Identify low-agency decisions that slow innovation (agencies, misaligned partners, restrictive funding)

    * Design products that increase customer empowerment by reducing friction, cost, and dependency

    * Evaluate tech stack and vendor choices based on incentive alignment and long-term control

    * Apply high-agency go-to-market strategies by selling directly to customers

    * Structure teams as cross-functional, autonomous squads that move fast and learn faster

    * Leverage AI as a force multiplier for founder and team agency



    The Pact

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    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 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.

    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.

    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/

    Reviewing Our 2025 Tech Predictions13 Nov 202500:40:22

    Were we wildly wrong, or surprisingly on the money?


    As 2025 wraps, Chris and Yaniv revisit the bold predictions they made at the start of the year. They reflect on their calls about AI, robotics, VC markets, crypto, and geopolitics. While some were accurate, some were also hilariously off. Together, they unpack what 2025 really looked like for startups, venture capital, and the global tech landscape.


    In this episode, you will:

    • Learn why both hosts believe their AGI predictions were misses and what “AGI” even means anymore.
    • Understand how Google re-emerged as a serious AI contender, from Gemini to Cloud to Chrome.
    • Discover how VC funding split into a two-speed market, with AI startups booming while everyone else grinds.
    • See why Bitcoin’s stability above $100K signals its cemented role as a store of value.
    • Reflect on how tech dominance, global competition, and Trump-era chaos shaped the broader economy.



    The Pact 

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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    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 OpenAI Evil? Reacting to Sam Altman's Latest Announcements w/ Jacob Ward06 Nov 202501:09:32

    OpenAI may appear to be building the future, but are they leading the tech industry towards collapse?


    In this episode, Chris and Yaniv are joined by Jacob Ward (journalist, author of The Loop and NBC Technology Correspondent) to break down OpenAI’s latest livestream and what it signals about the next era of AI. Sam Altman may talk the good talk, but his actions, and the priorities of OpenAI at large, may not align with those claims. Chris, Yaniv, and Jacob unpack these differences between words and actions, the emerging social consequences, and what it all means for the tech industry.


    In this episode, you will:

    • Understand OpenAI’s roadmap for AI-powered research and why "AI research interns" might be closer than you think
    • Learn why the promise of autonomous five-year research cycles raised eyebrows
    • Explore the shift from ChatGPT as a product to ChatGPT as a platform, and what that means for app ecosystems
    • Consider the emotional and psychological dimensions of AI companionship and reliance
    • Evaluate the trillion-dollar infrastructure buildup underway across data centers, GPUs, and nuclear-scale power demands
    • Examine how OpenAI’s nonprofit arm plans to invest in disease research and AI resilience


    The Pact 

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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    Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    Replay: Engaging Young Employees - How to Attract the Best & Brightest Minds w/ Dan Brockwell from Earlywork03 Nov 202500:44:34

    What do you need to do to keep employees engaged and committed? What should your position be on remote work? Side hustles? Ping pong tables? Should you offer all employees equity?


    Bringing Gen Z employees to your workplace is well worth it, but it means a mental pivot from the hiring team, keeping in mind an entirely new set of criteria.


    Chris and Yaniv discuss all this and more with Dan Brockwell, Founder and Chief Meme Officer of Earlywork, a vibrant community for early-career professionals.


    In this episode, you will:

    • Understand the four key factors Gen Z professionals weigh when choosing startups: learning, culture, compensation, and impact.
    • Learn why “job risk” and “career risk” are not the same and why startups often offer safer long-term bets.
    • Discover how equity (ESOPs) can be both a powerful motivator and a cultural signal of respect for young talent.
    • Explore the pros and cons of remote vs hybrid work for early-career employees and how to design hybrid intentionally.
    • Recognize the rise of side hustles, and how founders can embrace them to retain ambitious, creative employees.
    • Get insights into how Gen Z finds jobs through online communities, Slack channels, and personal branding instead of traditional job boards.


    [This is a replay episode. The original was published on May 26, 2022]


    The Pact 

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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    Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    Insiders React: Google's 'Quantum Advantage' + MIT's 'Telepathic' Interface, China Leads the Sci-Fi Future30 Oct 202500:43:22

    Is this the moment quantum computing becomes real?

    After years of being “five years away,” Google just announced a verifiable quantum advantage, claiming its Willow chip ran a molecule simulation 13,000× faster than the world’s fastest supercomputer. Is this truly the dawn of the quantum era?


    In this episode, Chris Saad and Yaniv Bernstein dive deep into Google’s latest quantum computing breakthrough, exploring what it means for AI, science, and the future of technology. They'll also expand to cover the rise of brain–computer interfaces, China’s ten-year tech roadmap, and the political turbulence shaping our next decade of innovation.


    In this episode, you will:

    • Understand Google’s new Willow chip and its role in achieving “verifiable quantum advantage”
    • Learn how quantum computing could accelerate drug discovery, materials science, and AI development
    • Explore why Google’s “Quantum AI” lab is merging the worlds of artificial intelligence and quantum physics
    • Hear how emerging brain–computer interfaces (like MIT’s Alter Ego) could usher in near-telepathic communication
    • Discover China’s bold 10-year plan targeting quantum tech, robotics, and embodied AI — and what it means for global competition
    • Debate whether technocratic governance models (like China, Singapore, and Dubai) are overtaking Western democracies in innovation speed



    The Pact 

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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    Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A 

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    Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    Trends in Startup Funding w/ Carta's Head of Insights, Peter Walker27 Oct 202501:06:09

    Looking to fund your startup? If you're new to the process, fundraising can be difficult to navigate. Not only are there a myriad of ways to go about it, but it can be hard to tell whether the tips, tricks, and advice floating around are based on any evidence at all.


    So, what is the truth? 

    And what are the actual, data-backed insights that can help you choose the best method of fundraising for your own business?


    Enter: Peter Walker. 

    As Head of Insights at Carta, he has access to, and industry knowledge about, the vast sets of funding data that will help you cut through the noise. Today, he joins Chris and Yaniv in discussing the real data behind startup funding trends in 2025 and the key takeaways you can apply to your own startups.



    In this episode, you will:

    • Discover why Silicon Valley valuations often hurt founders more than they help
    • Understand how AI startups now account for nearly half of all venture funding, and what that means for non-AI founders
    • Learn how lean AI-driven teams are reshaping early-stage hiring, with Series A companies shrinking from 25 employees to just 15
    • See why most founders misunderstand SAFE notes
    • Explore why 70% of startup employees never exercise their equity
    • Uncover the reasons behind why nearly 40% of startups lose a co-founder within seven years
    • Get clarity on founder vesting, equity splits, and why a six-year vesting schedule may protect your company better than four
    • Reframe your goals as a founder: why chasing “life-changing money” isn’t the right reason to start a company



    The Pact 

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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    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/


    Insiders React: Is ChatGPT Atlas The Future Of Browsing? + YouTube's AI Likeness Detection, Apple's New Vision Pro M523 Oct 202500:53:18

    OpenAI just dropped its unbelievable new browser. All signs point to it overshadowing Chrome, but is this really the dawn of a new era? Or just another hype cycle, courtesy of Sam Altman?


    In this episode, Chris Saad and Yaniv Bernstein react to OpenAI’s surprise launch of ChatGPT Atlas and debate its strategic implications. They also discuss Apple’s underwhelming Vision Pro refresh (and what it means for the company at large), YouTube’s new likeness detection tech, and Reid Hoffman’s viral post on “good vs. bad actors” in AI.


    In this episode, you will:

    • Explore what makes ChatGPT Atlas different from Chrome, Safari, and Arc, and why it matters.
    • Understand why OpenAI is desperate to own distribution, not just models.
    • Compare today’s “browser wars” with the 2000s Chrome vs. Internet Explorer showdown.
    • Learn how Apple’s Vision Pro M5 update signals the slow rebirth of spatial computing.
    • Discover why YouTube’s new Content ID for faces could be a turning point for AI deepfakes.
    • Hear how AI arms races mirror past battles like spam detection, piracy, and antivirus wars.
    • Unpack Reid Hoffman’s call for “good actors” in AI and whether self-regulation can actually work.



    Get started with Cyber Matters: https://www.cybermatters.io


    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
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    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/


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    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/


    The 4 Biggest Execution Mistakes Founders Make20 Oct 202500:43:01

    Think you’re executing well? Think again. Chances are you’re making one of these four common mistakes.


    Drawing from Chris’s latest essay and real-world advisory experience, Chris and Yaniv spend this episode breaking down the four biggest execution mistakes you're probably making right now. They explore how to recognize these patterns early, how to apply taste and judgment when scaling, and how to develop the discipline needed to execute with precision.



    In this episode, you will:

    • Identify when you’re oversimplifying, and mistaking nuanced, unique use cases for the same problem
    • Understand how overcomplicating your product or process can destroy focus and momentum
    • Learn to categorize problems correctly using the principle of mutually exclusive, collectively exhaustive thinking
    • Apply the concept of “necessary and sufficient” work — doing everything that’s needed and nothing that’s not
    • Recognize that mistiming priorities ends in attempting to do everything at once, but finishing nothing
    • Develop the taste, judgment, and rigor to strike the perfect balance between simplicity and depth
    • Avoid falling into domain dogma; naming, structuring, and communicating ideas clearly for your team and customers



    Read Chris’s original LinkedIn post: https://www.linkedin.com/posts/chrissaad_the-big-4-execution-mistakes-youre-probably-activity-7379681603847049216-ApcV



    The Pact 

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    Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    Insiders React: 'Treat Adult Users As Adults' Says OpenAI's Sam Altman + Oura's $900M Raise, NVIDIA's Funding Bubble16 Oct 202500:53:31

    OpenAI is set to roll out its new “treat adults like adults” policy, heralding the beginning of AI chatbots speaking more amorously with users. As the company pushes boundaries, from personality-rich bots to experimental devices, others are warning that the industry might be inflating a dangerous AI bubble.


    In this episode, Chris Saad and Yaniv Bernstein break down Sam Altman’s controversial announcement, unpack Johnny Ive’s vision for the next generation of OpenAI hardware, and debate whether Google’s slow-moving Gemini rollout signals resilience or decline. They also dive into the billion-dollar race for health data, exploring how Oura’s massive new raise fits into the wider AI gold rush.



    In this episode, you will:

    • Explore how OpenAI’s “Treat Adults Like Adults” philosophy changes the future of AI interaction
    • Understand the ethical and mental health challenges behind human-like AI personalities
    • Learn why Johnny Ive’s “family of AI devices” could redefine how we interact with technology
    • Examine Google’s glacial AI rollout and whether slow and steady approach might actually win the race
    • Unpack Bloomberg’s “AI Money Loop” and what it reveals about risky financial entanglements
    • Compare the AI investment surge to past industrial bubbles like railroads and dot-coms



    The Pact 

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    Work 1:1 with Chris: http://chrissaad.com/advisory/  

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    Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    Flow State: The Competitive Advantage You Need, And How To Harness It w/ Film Producer & Founder, Steven Puri13 Oct 202500:50:38

    What if your best work came from finding your flow, rather than simply grinding harder? In the age of constant distraction, many founders mistake busyness for progress, chasing notifications, meetings, and multitasking without realizing that true innovation happens when the mind is deeply focused.


    Today, Chris and Yaniv are joined by Steven Puri, former DreamWorks executive and founder of The Sukha, to unpack the science of flow state and why mastering it may be the ultimate founder advantage. From Hollywood film production to startup leadership, Steven shares how high performers sustain creativity and energy by designing their environments, schedules, and team cultures around deep work.


    They explore how to use neuroscience, rhythm, and intentional structure to unlock focus, eliminate context switching, and help your team reach peak performance without burnout.


    In this episode, you will:

    • Understand flow state, and how it fuels both productivity and creativity
    • Identify common barriers preventing founders from achieving deep focus
    • Learn how to structure your day around your natural chronotype for maximum energy
    • Implement practical tools and mental environments that enable sustained concentration
    • Explore how to build company cultures that protect “maker time” and empower deep work across teams
    • Adopt sustainable rhythms that increase output while avoiding founder burnout


    Find Steven on LinkedIn: https://www.linkedin.com/in/steven-puri

    Learn more about Sukha: https://www.thesukha.co


    The Pact 

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    Work 1:1 with Chris: http://chrissaad.com/advisory/  

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    Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

    Intro Voice: Jeremiah Owyang https://web-strategist.com/


    Insiders React: New ChatGPT Dev Tools Threaten App Store + Sora 2 Launch, Apple Removes ICE Block09 Oct 202500:47:02

    What happens when AI stops being a product and starts being a platform?

    With OpenAI’s latest Dev Day changing the game, we might find out sooner rather than later. 


    In this episode, Chris and Yaniv explore OpenAI’s Dev Day and the huge announcements made (including the Sora 2 launch), as well as their apparent transformation from product to platform. 

    In other tech news, the guys dive into Anthropic’s open-source counterpunch with Claude’s Agent SDK, along with Apple’s controversial censorship call - all while analyzing what all of this means for startup founders building in the AI era.


    In this episode, you will:

    • Understand how SDK, OpenAI’s new ChatGPT App, turns AI into a full developer ecosystem
    • Learn about “platform risk”,and how founders can avoid being crushed by it
    • Compare OpenAI’s walled-garden strategy to Anthropic’s open, Unix-inspired approach
    • Examine the launch of Sora, OpenAI’s new AI video social network, and why it matters
    • Debate whether large tech companies can ever succeed in building new social platforms
    • Analyze Apple’s ICE Block takedown and what it says about censorship in curated ecosystems



    The Pact 

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    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/


    Nailing Your Market Niche w/ Dutch CEO, Joe Spector (Spotlight)06 Oct 202500:58:59

    What happens when a founder who took a taboo health topic mainstream decides to reinvent pet care? In this Spotlight episode of The Startup Podcast, former Hims co-founder Joe Spector faux-pitches his startup Dutch, a telemedicine platform making veterinary care accessible, affordable, and convenient.


    Most founders fear tough questions from investors, this episode shows what happens when they face them live. Discover how Joe applies lessons from scaling a billion-dollar company to a completely different market, and how understanding regulation, timing, and storytelling can make or break your pitch.



    In this episode, you will:

    • Discover what makes a founder “fundable”, beyond just a good idea
    • Understand how Joe Spector scaled Hims and is now using those insights to disrupt pet telehealth with Dutch
    • Explore how regulatory insight can become a startup’s biggest competitive moat
    • See why subscription-based business models drive valuation and recurring growth
    • Find out how Dutch makes pet care up to 10x cheaper while creating flexible jobs for veterinarians
    • Hear expert commentary from Chris and Yaniv on storytelling, founder credibility, and investor psychology


    Learn more about Dutch: https://www.dutch.com/

    Connect with Joe: https://www.linkedin.com/in/joespector 



    The Pact 

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    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/


    Insiders React: ChatGPT Pulse: An Overpriced Daily Digest? + Hollywood’s First AI Actress, Amazon’s $2.5B Settlement02 Oct 202500:38:07

    OpenAI just launched ChatGPT Pulse, a succinct, personalized daily feed. Will this shift the focus of AI from performance to personal context? Or is it just an overhyped, overpriced daily digest? 


    In this episode, Chris and Yaniv get right into this week's tech news: the reality of ChatGPT Pulse, plus the wider implications of Hollywood's first AI actress, Tilly Norwood; Amazon's record-breaking $2.5B fine for deceptive Prime signups and the lessons founders can learn from it; and plenty more.



    In this episode, you will:

    • Understand why context, not just performance, is becoming the new moat in AI.
    • Explore how ChatGPT Pulse signals OpenAI’s strategy against Google and Apple.
    • Debate whether AI-generated actors like Tilly Norwood have a real future in Hollywood.
    • Learn what Amazon’s $2.5B FTC settlement teaches about dark patterns and user trust.
    • Identify the regulatory risks startups must consider when designing growth funnels.
    • Discover why Anthropic is shifting focus to enterprise and coding workflows.
    • Reflect on how distribution and lock-in, not just innovation, shape the competitive landscape.



    The Pact 

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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    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/


    How Being Genuine is a Critical Advantage For Startup Founders w/ Christine Blosdale, Expert Authority Coach (Edu)29 Sep 202500:50:45

    Standing out has gotten even more difficult thanks to the flood of AI content, and many early-stage founders mistakenly believe they need to act like corporate brands to be taken seriously.


    In this episode, Yaniv chats with Christine Blosdale, an award-winning media coach, podcaster, and branding strategist. Together they discuss how authenticity, personal branding, and “expert authority” can give founders a massive edge in today’s AI-driven startup landscape.


    They also explore how to overcome imposter syndrome, use AI responsibly, and build a founder-led brand that attracts talent, customers, and investors.


    In this episode, you will:

    • Discover why authenticity is now the ultimate differentiator in the age of AI and algorithmic content
    • Learn how to build “expert authority” to boost your reputation and visibility as a founder
    • Overcome imposter syndrome with practical mindset shifts that make content creation easier
    • Apply Christine’s tactics for repurposing podcasts, blogs, and videos to scale your personal brand
    • See why founder-led branding attracts better hires, investors, and partners
    • Create a simple media kit to clarify your mission, credentials, and unique value proposition


    Learn more about Christine here: https://www.christineblosdale.com 



    The Pact 

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    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/


    Insiders React: Tech Talent Pool to Be Decimated by New Fee + OpenAI Jobs Platform, $1B for Dishwashing Robots25 Sep 202500:53:27

    What happens to Silicon Valley when the world’s best founders and engineers can no longer afford to work in the US? 


    Today, Chris and Yaniv break down why the massive new work visa fee is a tech talent crisis waiting to happen. 


    They discuss how Trump’s surprising $100K H-1B fee could reshape startup hiring and the tech sector at large, along with the nitty gritty of Meta’s new smart glasses launch, and Figure AI’s billion-dollar Series C robots. They also unpack OpenAI’s unexpected jobs platform, and what it reveals about the future of AI work.


    In this episode, you will:

    • Understand how the new $100K H-1B visa fee could drain Silicon Valley of global talent
    • Explore why immigrant founders and startups may shift to Canada, the UK, or Australia
    • Discover how Meta’s new Ray-Ban and Oakley smart glasses bring AR into the mainstream
    • Compare Meta’s “bottom-up” approach to Apple’s Vision Pro strategy and timing
    • Examine Figure AI’s $1B+ raise and the coming battle with Tesla and Chinese robotics firms
    • Evaluate why OpenAI is launching a jobs platform amid fears of AI job loss
    • Learn actionable insights for founders navigating talent shortages, AR hardware, and AI disruption



    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/  
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    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/

    Why Every Startup Founder Should Consider B2B SaaS w/ Rob Walling (Edu)22 Sep 202500:58:29

    Is the new age of AI agents about to kill niche B2B SaaS businesses? Many first-time founders worry that tools like ChatGPT or custom AI builders will make off-the-shelf SaaS products obsolete, but it could simply herald a new evolution of SaaS.


    In this episode, Yaniv is joined by Rob Walling, serial founder, investor, and author of The SaaS Playbook, to break down why B2B SaaS still outperforms other business models and how founders can build defensible products – even in an AI-driven world.


    They explore the fundamentals of recurring revenue, why vertical SaaS wins over horizontal competitors, and the real opportunities AI creates for startup builders.


    In this episode, you will:

    • Understand why recurring revenue outperforms one-off sales for stability and growth.
    • Learn how vertical and orthogonal SaaS niches beat large horizontal players.
    • Discover the importance of high margins and why bootstrapping B2B SaaS is often possible.
    • Evaluate how net revenue retention and negative churn can exponentially increase enterprise value.
    • Apply Rob’s 2-20-200 framework to validate and launch your own SaaS idea.
    • Explore how to use AI as a feature or an enabler rather than seeing it as a threat.
    • Gain insights on positioning, pricing, and finding your ideal customer profile in crowded markets.


    Learn more about Rob Walling and his work here: https://robwalling.com 



    The Pact 

    Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:

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    Work 1:1 with Chris: http://chrissaad.com/advisory/  

    Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  

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    Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur

    Intro Voice: Jeremiah Owyang https://web-strategist.com/

    Insiders React: YouTube's Steady Domination + Oracle's AI Comeback, Sam Altman v. Tucker Carlson18 Sep 202500:55:08

    Is YouTube quietly becoming the most powerful platform in the world? Announcements made during Made On YouTube 2025 revealed incredibly promising long-term plans, with the media giant seemingly set to dominate video, music, and podcasts with the help of Google’s AI.


    Too many entrepreneurs still see YouTube as ‘just’ a video host, missing the bigger picture: it’s a global discovery engine and monetization machine. In this episode, Chris and Yaniv break down YouTube’s creator ecosystem and what their announcements mean for the future of media services. They also delve into Oracle’s unexpected AI rise, Sam Altman’s high-pressure interview on AI ethics, and Figma’s new AI tools reshaping design.


    In this episode, you will:

    • Discover how YouTube’s latest AI tools could outpace TikTok and Spotify in shorts, podcasts, and music
    • Learn why Oracle’s $100B OpenAI cloud deal and TikTok nationalization play mark a massive comeback
    • Understand Sam Altman’s tough Tucker Carlson interview and what it reveals about OpenAI’s ethics stance
    • Explore Figma’s breakthrough AI features and what they mean for designers and startup teams
    • See why “Nothing” phone’s $200M AI-first push could disrupt Apple and Google’s hardware advantage
    • Identify key lessons in strategy, timing, and neutrality from Oracle’s approach to AI infrastructure
    • Apply insights from vibe coding and vibe design tools to accelerate your own startup workflow



    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
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    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/


    Startup Persistence: A Masterclass from YC Founder Paul Graham15 Sep 202500:41:13

    Are you truly being persistent with your startup, or just being stubborn? In the new age of AI-powered founders and hyper-fast iteration, many entrepreneurs mistake obstinacy for persistence and end up running out of time, money, and morale.


    Too often we glorify “hustle” and “grit” without understanding when to adapt, pivot, or quit. The misconception that sheer willpower equals success has caused countless startups to fail, not because the idea was bad, but because the founder couldn’t tell when to change course.


    In this episode, Chris and Yaniv dive deep into Paul Graham’s classic essay on the difference between persistence and obstinacy. Drawing from decades of startup experience, they unpack why adaptability, “predatory listening,” and goal-directed experimentation are the true drivers of breakthrough success.


    They explore the five traits that set persistent founders apart (energy, imagination, resilience, good judgment, and focus) and explain how to build these skills into your daily practice as a founder.


    In this episode, you will:

    • Discover the critical difference between persistence and obstinacy in startup culture
    • Learn Paul Graham’s “boat rudder vs. boat engine” metaphor and why it matters for founders
    • Identify the five traits every successful founder must develop to survive and thrive
    • Understand how “predatory listening” and adaptability accelerate learning and reduce risk
    • Explore real-world examples (Stripe, Uber) showing how top founders embody these traits
    • Apply practical strategies to know when to double down, pivot, or quit a failing idea
    • Gain a fresh perspective on why resilience and imagination matter more than raw hustle



    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/
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    • Give us a public shout-out on LinkedIn or anywhere you have a social media following


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    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/


    #Resilience #Startups #Founder #TheStartupPodcast #Mindset

    Insiders React: Apple's Huge AI Blunder + IPO Market Heats Up, White House Tech Dinner11 Sep 202500:57:09

    With Apple’s iPhone Air, iPhone 17 Pro, AirPods Pro 3, and Apple Watch 11 now unveiled, what does this mean for the future of phones and wearable tech? And does the incredible AI of Google Pixel still blow Siri out of the water?


    In this episode, Chris and Yaniv delve into Apple’s newest product lineup and what it reveals about the company’s long-term strategy, particularly in the current AI-driven climate. They also discuss both the IPO market heating back up and the recent White House tech dinner, the implications both of these have on the tech industry, and the key takeaways for you as a founder.



    In this episode, you will:

    • Unpack Apple’s biggest announcements, from the ultra-thin iPhone Air to the next iterative iPhone 17
    • Explore the hidden strategy behind AirPods Pro 3’s real-time translation and heart-rate monitoring features
    • Learn why Apple Watch 11’s new health functions could reshape the wearable market
    • Analyze why Apple’s generative AI gap matters and how it compares with Google’s approach
    • Understand how the authenticity economy is changing hiring, recruiting, and founder strategy
    • Gain insight into the rebounding IPO market and what it signals for startup liquidity



    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/


    Growing a Pre-Seed Startup? This Is The Core Knowledge You Need w/ Ashley Smith08 Sep 202500:57:54

    Pre-seed founders want explosive growth early on, but are you following the wrong playbook too soon? These days strategies, acronyms, and well-intended advice are everywhere, but today's guest argues that the path forward is a simple one: talk to customers, run experiments, and embrace rejection as part of the journey.


    In this episode, Yaniv Bernstein speaks to guest Ashley Smith (ex-Twilio, Parse, GitLab, GitHub, and now General Partner at Vermilion Cliffs) and unpacks what it really takes for your startup to go from zero to one. Ashley has been at the helm of some of the most successful developer tool companies in the last decade and now invests in the next generation of technical founders. She shares raw insights from the trenches on how to build community, experiment with growth, and keep your startup alive through grit and iteration.


    In this episode, you will:

    • Learn why investor playbooks can be dangerous for early-stage founders
    • Understand why customer conversations matter more than LinkedIn hot takes
    • Discover how product and marketing should be treated as one cohesive strategy
    • Explore how companies like Twilio, Parse, and GitLab grew by leaning into community, content, and relentless product shipping
    • See why hiring generalists and “specialists in experimentation” is the best early-stage move
    • Gain tactical tips on creating authentic founder content in the age of AI slop
    • Embrace rejection as a natural (and necessary) part of fundraising and early customer acquisition



    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 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/


    Insiders React: Google Antitrust: Is The Ruling Fair? + YC’s Latest Request For Startups, Statsig Acquisition04 Sep 202500:47:43

    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% overnight
    • Learn what OpenAI’s Statsig acquisition signals about its long-term strategy
    • Explore why YC’s latest startup requests are so heavily AI-focused, and why that’s a mistake
    • Compare today’s antitrust rulings with the Microsoft case of the 1990s
    • Discover how AI may disrupt not just tech, but also government consulting and enterprise software
    • Get Yaniv’s insider view on why intent-driven marketplaces may be the next frontier


    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/


    First Principles: Listen to This Before You Apply to YC01 Sep 202500:38:04

    It seems like startup accelerators are everywhere these days. But what are they? What’s the point of them? And most importantly, is it worth having your startup go through one?

    Based on their own experience with YC and startups, Chris and Yaniv talk you through it all.


    In this episode, you will:

    • Learn what startup accelerators are and how they work.
    • Discover the primary benefits of going through a startup accelerator.
    • Understand whether applying to a startup accelerator is right for you.
    • Explore the process of choosing an accelerator.
    • Listen to Yaniv’s first-hand experience going through the Y Combinator accelerator.


    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/

    Insiders React: Google Pixel 10 – Does It Finally Beat Apple at Its Own Game?28 Aug 202500:35:21

    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 line
    • Explore why AI-first design is becoming the true battlefield in smartphones
    • See how proactive AI (Magic Q, contextual responses, Gemini integration) could reshape user experiences
    • Discover why patience and iteration are critical lessons for startup founders
    • Apply insights from platform ecosystems (reference apps, open source, and monetization strategies) to your own business


    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/


    Startup Tech Stacks: Make Your Product Stand Out & Get Used w/ Joseph Ruscio25 Aug 202501:04:17

    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 growth
    • Learn how AWS scaled from startups to Fortune 500s—and what founders can copy
    • Discover 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 adoption
    • Explore how AI is changing developer workflows and the future role of engineers
    • Identify the risks of being “too close to your own pain” as a technical founder
    • Apply practical guidelines for choosing your startup’s tech stack without overthinking


    DevGuild 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 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/


    © My Podcast Data · Projet indépendant · Données issues d'Apple & Spotify