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

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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

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/

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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/

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/

Were we wildly wrong, or surprisingly on the money?

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

In this episode, you will:

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

The Pact

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

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

Key links

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

The Startup Podcast website: https://www.tsp.show/episodes/

Learn more about Chris and Yaniv

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

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

Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

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

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

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

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

In this episode, you will:

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

The Pact

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

• Follow, rate, and review us in your listening app

• Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe
• Secure your official TSP merchandise at https://shop.tsp.show/
• Follow us here on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg
• Give us a public shout-out on LinkedIn or anywhere you have a social media following

Key links

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

The Startup Podcast website: https://www.tsp.show/episodes/

Learn more about Chris and Yaniv

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

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

Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

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

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

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

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

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

In this episode, you will:

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

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

The Pact

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

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

Key links

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

The Startup Podcast website: https://www.tsp.show/episodes/

Learn more about Chris and Yaniv

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

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

Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

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

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