
Advertise on podcast: The Startup Podcast - advice for early stage tech founders from Silicon Valley insiders
Rating
4.9from
This podcast has
314 episodes
Language
EnglishDate created
2022/03/04
Latest episode
2026/10/16
Average duration
52 min.
Release period
12 days
Description
Advice for founders and entrepreneurs who want to build disruptive startups like they do in Silicon Valley. Not another interview podcast: concrete tips and masterclasses on what founders need to know: raising Venture Capital, strategy, product, marketing, growth, and more. A guide to the unique mindset and approach that drives Silicon Valley style disruption. Hosts Chris Saad and Yaniv Bernstein share practical advice based on decades of experience at Google, Uber, and their own startups.
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Check latest episodes from The Startup Podcast - advice for early stage tech founders from Silicon Valley insiders podcast
Applied Wizardry: Cutting AI coding token costs, with Dave Slutzkin
2026/10/16
Follow Applied Wizardry on its new feed to keep getting every episode.
Dave Slutzkin, co-founder of Antiburn, joins Yaniv to break down what actually drives token costs in agentic development and how to bring them down. They cover how caching differs between Anthropic and OpenAI, when to reach for which model and thinking mode, and why the habit of compaction matters more than any other optimisation. If you're spending real money on AI-assisted development, you'll come away with concrete tactics for cutting token burn without cutting capability.
Key takeaways
Context window depth is the dominant driver of token cost; compacting actively at 200,000-300,000 tokens matters more than any other single action.Cache expiry behaviour differs materially between providers: Anthropic's cache expires at exactly 1 hour, OpenAI's Codex cache is best-effort and often drops in 5-20 minutes, but OpenAI subscriptions do not charge for cache writes while Anthropic subscriptions effectively do through quota.Using a frontier model with a simple prompt to delegate to cheaper subagents is a practical pattern that balances capability and cost without requiring complex harness engineering.High thinking modes often produce worse results than medium or low because models overthink, invent requirements, and fix unrelated bugs; the benchmark sweet spot is typically medium.Skills files, MCPs, auto-memories, and system prompts silently bloat context windows; regular clean-up every month or two reduces both cost and quality degradation.Fast mode costs 2.5x per token but can improve output quality through tighter interaction loops; it is best used deliberately rather than left on by default.Chapters
00:00 Introduction00:38 The Token Burn Problem03:12 Three Stages of Adoption07:03 Model Choices Multiplying11:14 The Cardinal Mistake: Depth18:13 Worst-Case Usage Patterns22:13 Picking Models by Feel30:23 Thinking Modes and Overthinking35:23 Fast Mode Trade-offs48:46 Caching: Anthropic vs OpenAI52:29 Context Window Ceiling56:32 Cleaning Up Context Bloat56:46 Where to Find DaveLinks and tools mentioned
Antiburn: https://antiburn.comAnthropic Claude: https://www.anthropic.comOpenAI Codex: https://openai.com/codexHarvey: https://www.harvey.aiLegora: https://legora.comAbout Dave Slutzkin
Co-founder of Antiburn, a company that helps developers understand and optimise their token spend for AI-assisted coding.
This episode is presented by SparkLaunch and Dam Secure.
SparkLaunch (https://sparklaunch.io/wizardry): Applied Wizardry listeners get an extra 20% off.Dam Secure (https://damsecure.ai/wizardry): Applied Wizardry listeners get their first month free.Credits
Justin McArthur, Executive Producer and Video Editor: https://www.linkedin.com/in/justin-mcarthur/Steph Hefferan, Editor: https://www.linkedin.com/in/steph-heff/
ScaleStudio: The new tool putting our principles into practice
2026/08/03
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
ScaleStudio (Chris’s AI-powered product strategy tool): https://scalestudio.io/
Vera (Yaniv's Startup): https://vera.guide
The Pact
Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
Follow, rate, and review us in your listening app
Secure your official TSP merchandise at https://shop.tsp.show/
Follow us on YouTube for full video episodes: https://www.youtube.com/@startup-podcast
Give us a public shout-out on LinkedIn or anywhere you have a social media following
Key links
This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar.
The Startup Podcast website: https://www.tsp.show/episodes/
Learn more about Chris and Yaniv
Work 1:1 with Chris: http://chrissaad.com/advisory/
Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/
Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/
Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur
Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/
Intro Voice: Jeremiah Owyang https://web-strategist.com/
Rob Snyder demonstrates his PULL framework in real-time – using Yaniv's startup
2026/07/27
A few weeks ago, Rob Snyder came on the pod to introduce his PULL framework for identifying real product-market fit. Now, Yaniv turns the tables and subjects his own startup, Vera, to the same scrutiny.
Yaniv and Rob strip away the noise around Vera's mission to help adult children care for aging parents and get brutally honest about where the product actually has pull, where it doesn't, and what needs to change immediately. They identify a specific, unavoidable moment in the customer journey and pinpoint that is where the real business begins, and discuss more macro issues, such as AI vs. human expertise, founder blind spots, and more.
In this episode, you will:
Understand the difference between an aspiration and a project, and why this distinction is vital for PULL
Learn how the PULL framework cuts through startup theory to identify the exact moment when customers will actually pull your product from your hands, before they have to wait for a crisis
Discover why Vera's original problem was too abstract, and how narrowing to a specific market segment with intense, unavoidable need becomes your path to revenue and growth
Hear the truth behind what really pushes your customers to adopt earlier: reality does the convincing, not your marketing
Understand the challenge of reputation in AI: how do human-shaped applications build trust the way human experts do?
Timestamps
00:00 Coming Up
01:38 On Today's Show: Yaniv Applies PULL to Vera
04:42 Defining PULL and Projects
05:54 Vera's Customer Goals
08:00 Unavoidable Moments and Crisis
11:25 Real Users and Traction
16:58 Mission vs Push Marketing
24:07 Why Isn't Google Enough?
28:21 Nailing the Specific Project
34:02 Testing Market With Ads
37:06 Bill Gates And AI Shift
38:47 Human Shaped Software Design
43:45 Trust And Reputation In Bots
48:48 About The Book
Resources mentioned in this episode
The Power of Pull by Rob Snyder: https://www.amazon.com/Power-Pull-Customer-Successful-Founders/dp/1541705955
Rob Snyder's website: https://www.robsnyder.org
Vera (Yaniv's startup helping families care for aging parents): https://vera.guideClub Sandwich, Vera's podcast and community for the sandwich generation: https://clubsandwich.communityWhat the sandwich generation is (and why it's Vera's market): https://clubsandwich.community/sandwich-generation
The Pact
Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
Follow, rate, and review us in your listening app
Secure your official TSP merchandise at https://shop.tsp.show/
Follow us on YouTube for full video episodes: https://www.youtube.com/@startup-podcast
Give us a public shout-out on LinkedIn or anywhere you have a social media following
Key links
This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean and memorable name, go to https://get.tech/tsp
This episode of the Startup Podcast is sponsored by Vanta. Vanta helps businesses get and stay compliant by automating up to 90% of the work for the most in demand compliance frameworks. With over 200 integrations, you can easily monitor and secure the tools your business relies on. For a limited time offer of US$1,000 off, go to https://www.vanta.com/tsp
The Startup Podcast website: https://www.tsp.show/episodes/
Learn more about Chris and Yaniv
Work 1:1 with Chris: http://chrissaad.com/advisory/
Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/
Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/
Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur
Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/
Intro Voice: Jeremiah Owyang https://web-strategist.com/
Why you should run your startup like a poker player (Replay)
2026/07/20
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)
2026/07/13
Is hiring a person still your default answer to a problem? For a growing number of startups, it shouldn't be.
In this episode, Yaniv Bernstein is joined by returning guest Matt Cook, co-founder of Scouut, one of Australia's most respected engineering recruiters for early-stage startups, to unpack what's changed in engineering hiring since Matt's last visit. They cover ‘team debt’ (the AI-era sequel to tech debt), why AI is acting as an appetite suppressant for headcount, why the best engineers are now worth $400K+, and why the ‘software factory builder’ is becoming the most sought-after hire in tech.
In this episode, you will:
Understand "team debt", and why teams built to solve today's problems are already becoming obsolete
Learn why "removing the crutch" (like scrapping a QA gating function) forces the kind of AI-native change that timid, incremental adjustments never will
Discover why most startups were already overstaffed before AI, and why AI now acts as an ‘appetite suppressant’ for hiring rather than just an efficiency tool
Hear why hiring should now be treated as a last resort, and what that actually means in practice for founders
Understand why compensation banding and headcount-based budgeting are breaking down, and what smart companies are replacing them with
Learn about the rise of the ‘software factory builder’: the rare, highly-paid engineer who uses their judgment to build airtight, AI-based infrastructure the rest of the team can lean on
Timestamps
00:00 Coming Up...
00:58 On Today's Show: Matt Cook on 'Team Debt'
02:36 What is Team Debt?
05:12 Refocusing on AI Native Solutions
10:40 Unlearning Old Hiring Ladders
12:04 Why Companies Are Oversized
14:59 AI, the 'Corporate Ozempic'
19:25 Layoffs and Team Composition
24:02 Disrupting Yourself at Series B
28:12 The Salary Race for AI Engineers
34:01 Limitations of Headcount Budgeting
38:16 How Downsizing Can Help You Grow
41:13 ClickUp's 'Hail Mary' Pivot
44:26 Software Factory Builders and 'Forward Deployed' Automation
49:14 Maintaining Safe Internal Software
54:25 Closing Thoughts
Resources mentioned
Scouut (Matt Cook's engineering recruitment firm for early-stage startups): https://scouut.com.au/
Matt Cook on LinkedIn: https://www.linkedin.com/in/matthewmarkcook/
'Corporate Ozempic' by Scott Galloway — the essay behind the AI/hiring analogy Yaniv references: https://www.profgalloway.com/corporate-ozempic/
The Pact
Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
Follow, rate, and review us in your listening app
Secure your official TSP merchandise at https://shop.tsp.show/
Follow us on YouTube for full video episodes: https://www.youtube.com/@startup-podcast
Give us a public shout-out on LinkedIn or anywhere you have a social media following
Key links
This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean and memorable name, go to https://get.tech/tsp
This episode of the Startup Podcast is sponsored by Vanta. Vanta helps businesses get and stay compliant by automating up to 90% of the work for the most in demand compliance frameworks. With over 200 integrations, you can easily monitor and secure the tools your business relies on. For a limited time offer of US$1,000 off, go to https://www.vanta.com/tsp
The Startup Podcast website: https://www.tsp.show/episodes/
Learn more about Chris and Yaniv
Work 1:1 with Chris: http://chrissaad.com/advisory/
Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/
Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/
Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur
Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/
Intro Voice: Jeremiah Owyang https://web-strategist.com/
How good timing makes great products w/ Paul Orlando
2026/07/06
Every startup pitch deck has a "why now" slide. Most of them are nonsense, barely considered, and only there to tick a box.
But timing is more than a slide, it can make or break a company. It’s the difference between pets.com and the trillion-dollar company selling the exact same idea a decade later.
In this episode, Yaniv Bernstein sits down with Paul Orlando, who has built four startup accelerators supporting over 300 companies, including Hong Kong's first accelerator and a program in Rome run in partnership with the Vatican, and has taught entrepreneurship at USC for over a decade, where he also runs one of LA's largest startup incubators. Paul has spent years obsessing over a single question: why do some ideas succeed while near-identical ones fail years earlier? The answer became his book, ‘Why Now? How Good Timing Makes Great Products.’
In this episode, you will:
Learn Paul's framework of timing drivers, and the five that show up again and again: technology, social/behavioral change, regulation, installed base, and crisis
Walk through the YouTube case study in detail to see how broadband penetration, digital camera adoption, and falling storage costs converged to make 2005 the right year, after the identical idea failed less than a decade earlier
Discover why first-mover advantage is much narrower than founders assume, and the two specific conditions (locking in customers, locking out competitors) required for it to actually work
Get a framework for balancing founder agency against timing, because you can't will your way into good timing, but you also can't wait passively for the perfect moment to arrive
Timestamps
00:00 Coming Up...
01:04 On Today's Show: Why Timing Matters
01:44 Guest Intro: Paul Orlando
02:42 Is 'Why Now' Predictable?
05:40 Paul's Timing Drivers Framework
08:44 Case Study: YouTube's Market Timing
11:47 Business Model Shifts
15:16 Case Study: Pets.com Unit Economics
22:16 Case Study: AI Vibe Coding
24:11 What Are 'Sleeping Beauty' Startups?
27:46 Incorporating AI into Timing Drivers
28:52 Collapse of Build Costs
33:34 Case Study: Vera and Unit Economics of Voice
35:15 False 'Why Now' Risks
37:46 First Mover Reality
40:33 Reid Hoffman on Blitzscaling
41:49 Case Study: AT&T's Picturephone and Mobile Telephony
46:31 Lessons on Failure and Agency
54:09 Closing Thoughts
Resources mentioned
'Why Now?: How Good Timing Makes Great Products' by Paul Orlando: https://www.amazon.com/Why-Now-Timing-Makes-Products/dp/B0CYXSNMT3
Paul's website, Startups Unplugged: https://startupsunplugged.com
Paul on LinkedIn: https://www.linkedin.com/in/porlando
Paul on X/Twitter: https://twitter.com/porlando
The Pact
Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
Follow, rate, and review us in your listening app
Secure your official TSP merchandise at https://shop.tsp.show/
Follow us on YouTube for full video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg
Give us a public shout-out on LinkedIn or anywhere you have a social media following
Key links
This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar.
The Startup Podcast website: https://www.tsp.show/episodes/
Learn more about Chris and Yaniv
Work 1:1 with Chris: http://chrissaad.com/advisory/
Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/
Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/
Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur
Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/
Intro Voice: Jeremiah Owyang https://web-strategist.com/
Make your product irresistible: Rob Snyder on the PULL framework
2026/06/29
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 anythingLearn 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 handsHear 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 unavoidableGet 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/1541705955Rob's website: https://www.robsnyder.orgRob on LinkedIn: https://www.linkedin.com/in/rsnyder1Rob's Substack, 'The Physics of Startups': https://thephysicsofstartups.substack.comEric Ries's TSP episode: https://youtu.be/HQ7cP1lGyiM April Dunford's TSP episode: https://youtu.be/QC4cKxlW81sMark 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)
2026/06/22
Founders are told that if they work hard, build the right product and hire well, the outcome will follow. It's motivating. It's clean. And according to today's guest, it's mostly wrong.
Mike Grossman has been CEO of six venture-backed Silicon Valley companies. Across them, he tried 18 different business models. Twelve failed. Five required layoffs. Three lived in persistent existential crisis. And yet all six were eventually acquired. Mike's story is one that far more founders actually live, but almost nobody tells.
In this episode, Yaniv Bernstein sits down with Mike to dig into his new book, Failure Is An Option: a candid 44-essay collection drawn from three decades in the trenches. They explore the uncomfortable truth that luck dominates outcomes more than skill, why your business model is not your business, and how radical honesty is the most underrated leadership tool in a founder's kit.
In this episode, you will:
Learn about 'resulting': why confusing luck for skill costs founders in both directions
Hear how Mike pivoted Tempo from building a Visa/Mastercard competitor to partnering with Mastercard, only to have the entire model wiped out overnight by a Senate amendment
Discover the 'dreamers vs soldiers' framework for building teams that hold together when adversity strikes
Hear Mike's hard-won playbook for layoffs: why founders almost always cut too little, too late; what day two feels like; and why a smaller, denser team is often more productive
Get a clear framework for staying accountable for the process when the outcomes aren't in your control
Timestamps:
00:00 Coming Up...
00:34 On Today's Show: Mike Grossman on Managing Failure
02:02 The Role of Luck and Timing
03:41 Poker Strategy and 'Resulting'
08:55 "The Business Model Is Not The Business"
11:27 Tempo's Pivot
13:28 Why Values Matter In A Crisis
19:21 Talent Density and Layoffs: Cut Once, Cut Deep
28:15 How AI Changes Hiring Pace
32:15 Leading with 'Radical Honesty'
36:33 Dreamers vs. Soldiers
38:02 Managing Investors
41:43 Luck, Agency, Process
48:39 About 'Failure Is An Option'
51:29 Closing Thoughts
Resources mentioned
'Failure Is An Option' by Mike Grossman: https://www.failureisanoption.comMike Grossman's Substack: https://failureisanoption.substack.comThinking in Bets by Annie Duke (the 'resulting' concept discussed): https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216355'Incorruptible' by Eric Ries: https://www.incorruptible.co/Eric Ries's TSP episode: https://youtu.be/HQ7cP1lGyiM 'Powerful' by Patty McCord: https://www.amazon.com/Powerful-Building-Culture-Freedom-Responsibility/dp/1939714095Patty McCord's TSP episode: https://www.youtube.com/watch?v=BefnNLBEmXAThe Durbin Amendment (the legislation that killed Tempo): https://en.wikipedia.org/wiki/Durbin_amendmentThe 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 IPO
2026/06/16
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 frontStrategy dividends: how Anthropic's genuine commitment to safety became both a real constraint and a powerful marketing asset at the same timeClaude’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-graceBen Thompson's Stratechery: https://stratechery.comProject Glasswing (Anthropic's restricted Mythos access program): https://www.anthropic.com/glasswingEric 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
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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 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)
2026/06/08
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 intoLearn 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 rejectDiscover 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.comGary Lo's previous TSP episode: https://youtu.be/jtMgd7Nv_HYThe 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 software
2026/06/01
What if writing software became as easy as taking a selfie?
This episode, Yaniv Bernstein sits down with Gary Lo - founder of OpenBA and one of the sharpest AI-and-startups thinkers Yaniv knows - to discuss the concept of 'selfie software': disposable, hyper-personal, AI-generated tools that anyone can create for themselves, with no hand-written code.
AI-generated tools like these are changing the startup landscape. While founders now have more tools at their disposal, it's now necessary than ever to create a product that truly disrupts the market.
Gary and Yaniv discuss all of this and more, likening Claude and ChatGPT to Windows and Mac, and exploring what this tech landscape means if you're building a software startup today.
In this episode, you will:
Understand the 'selfie software' concept: why AI is making software disposable, personal, and low-stakes, and what that means for the market you're building in
Learn why AI platforms are forcing startups to rethink whether they should build on their own infrastructure or embed into Claude and ChatGPT instead
Hear Gary's 'burn it down' exercise: how to identify which parts of your product are genuinely defensible, and which will simply catch fire in the next AI wave
Understand why software engineering isn't dead, but the problems worth solving with it have fundamentally shifted
Timestamps
00:00 Coming Up...
01:09 On Today's Show: Gary Lo on 'Selfie Software'
02:48 About Gary
03:16 How 'Hyper-Personalized' AI Is Like Photography
05:36 Gary's Real Estate Workflow (OpenBA)
07:29 Defining 'Selfie Software': Why Custom Tools Win
10:33 So... Is It Bad Software?
13:29 'Can’t You Just Add This One Thing...'
15:30 When Personalization Becomes Bloat
17:42 Working In-App with Anthropic and OpenAI APIs
20:29 Token Economics and Moats
25:28 Microsoft's Lessons in Platform Power
30:27 But What If Anthropic Comes For My Vertical?
32:48 How Open Source Keeps AI in Check
35:18 Unlearning and Rebuilding
39:05 Gary's 'Burn It Down' Test
44:01 Is Software Engineering Dead? (No.)
50:17 Closing Thoughts
Resources in this episode
Gary Lo's previous TSP episode (on OpenClaw and Claude Cowork): https://youtu.be/V3YFghiy8p0
Garry Tan's gstack: https://github.com/garrytan/gstack
Andrej Karpathy on Software 2.0: https://karpathy.medium.com/software-2-0-a64152b37c35
Vera (Yaniv's startup, AI-supported guidance for people caring for ageing parents): https://vera.guide
The Pact
Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
Follow, rate, and review us in your listening app
Secure your official TSP merchandise at https://shop.tsp.show/
Follow us here on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg
Give us a public shout-out on LinkedIn or anywhere you have a social media following
Key links
This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean name that highlights your tech credentials, get a .tech domain at your favorite registrar.
This episode of the Startup Podcast is sponsored by Vanta. Vanta helps businesses get and stay compliant by automating up to 90% of the work for the most in demand compliance frameworks. With over 200 integrations, you can easily monitor and secure the tools your business relies on. For a limited time offer of US$1,000 off, go to https://www.vanta.com/tsp
The Startup Podcast website: https://www.tsp.show/episodes/
Learn more about Chris and Yaniv
Work 1:1 with Chris: http://chrissaad.com/advisory/
Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/
Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/
Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur
Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/
Intro Voice: Jeremiah Owyang https://web-strategist.com/
Author Eric Ries (The Lean Startup) on how to build an incorruptible company
2026/05/25
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:
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/
FEED DROP: Could AI Make Capitalism Better? Henrik Werdelin Is Optimistic (from FAFO with Dan Blumberg)
2026/05/21
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 makeThe three components of relationship capital: intensity, community, and durabilityThe "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 appThe 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 meetingWhy entrepreneurial skills—agency, narrative, resourcefulness—are the ultimate career insurance, whether you start a company or notThe absolutely ridiculous story of how a prank on a cruise ship led to him meeting his BARK co-founder in a heart-shaped bedChapters
(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-mcarthurAssistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/
The Science of Scaling: Using data to scale your startup perfectly w/ Mark Roberge
2026/05/18
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
Follow us on YouTube for full-video episodes: https://www.youtube.com/@startup-podcast
Give us a public shout-out on LinkedIn or anywhere you have a social media following
Key links
This episode of the Startup Podcast is sponsored by .tech domains. Forget weird prefixes and creative misspellings; the availability for .tech domains is simply way better than .com. For a clean and memorable name, go to https://get.tech/tsp
This episode of the Startup Podcast is sponsored by Vanta. Vanta helps businesses get and stay compliant by automating up to 90% of the work for the most in demand compliance frameworks. With over 200 integrations, you can easily monitor and secure the tools your business relies on. For a limited time offer of US$1,000 off, go to https://www.vanta.com/tsp
The Startup Podcast website: https://www.tsp.show/episodes/
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 startups
2026/05/11
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
Josh Foreman on LinkedIn: https://www.linkedin.com/in/joshforeman/
InDebted: https://www.indebted.co/
Scott Galloway on 'Corporate Ozempic': https://www.profgalloway.com/corporate-ozempic/
Surviving the AI SaaSpocalypse with Scotty Allen: https://youtu.be/j84LF4aru8I
'Paranoid Optimism' with Yaniv: https://youtu.be/FGqbdzr0-PM
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/
Podcast reviews
Read The Startup Podcast - advice for early stage tech founders from Silicon Valley insiders podcast reviews
pointmatic 2025/10/09
Laughable Political Commentary
I like the show, but they just can’t help blathering about American politics and how fast and wide the sky is falling. It would be better to create a ...
lavhill 2025/07/16
Masterclass for Startup Founders and Innovators
We all have it within us to be the best. The Startup Podcast is a must-listen for anyone in the startup ecosystem — whether you're a first-time founde...
YourCTO 2025/05/19
Must-Listen for Startup Storytellers
Love the podcast overall and especially enjoyed the deep dive into the attention economy with Ben Parr—this one hit home. As someone who’s led product...
Sachin Wadhawan 2025/02/16
Super insightful and candid
I am hooked and I have only listened to a few episodes. The format is very easy to follow and the quality of guest speakers is amazing. Thank you for ...
Sugaku 2025/01/15
It’s the truth
In my role as a repeat startup founder I have read a lot of advice, along with working with mentors and an executive coach. This podcast very clearly...
gishcore 2024/11/06
Researching for help
After 12 years in development I am about to launch a product. I’ve written and obtained patents; I’ve done product testing; and I’m very confident tha...
GeneCro 2024/10/16
An Insightful and Refreshing Perspective within and around the Startup World
Introduced to this Podcast through another great one hosted by Matt Watson with the “Startup Hustle”. Yaniv had an interview back in April 2024 which ...
radeljr 2024/09/04
My Go-To Listen for Business Insights
I recently started working at a startup in the Silicon Valley. Things move so fast, but thankfully people really love sharing how they have succeeded ...
knock on wall 2024/07/31
Informative and Reliable
Great source of information for start-up knowledge and up-to-date insights on recent news
Sara Montreal 2024/06/05
Great podcast for founders
Very experienced people in these podcasts
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