The Startup Podcast

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

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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.

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

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/

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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 .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

(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:

• Part 1 of this conversation, 'How to identify red flags early in your co-founder relationship': https://www.tsp.show/how-to-identify-red-flags-early-in-your-cofounder-relationship-w-dr-matthew-jones/

• Dr. Matthew Jones' website, Cofounder Clarity (further information on his coaching practice and his book, The Cofounder Effect): https://www.cofounderclarity.com

• Startup Snapshot: https://www.startupsnaphot.com

• Nonviolent Communication (NVC): https://www.cnvc.org

• 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.

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/

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/

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/  

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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 .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/

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/

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/

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/

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

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 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

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:

• 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 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/

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

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 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/