The Startup Podcast

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

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

In this episode, you will:

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

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

The Pact 

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

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

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

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

Learn more about Chris and Yaniv

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

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

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

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

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

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

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

In this episode, you will:

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

The Pact 

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

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

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

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

In this episode, you will:

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

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

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

The Pact 

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

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

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

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

In this episode, you will:

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

The Pact 

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

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

In this episode, you will:

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

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

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

The Pact 

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/

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

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

In this episode, you will:

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

The Pact 

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

• 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/

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

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

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

In this episode, you will:

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

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

The Pact 

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

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

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

In this episode, you will:

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

The Pact 

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

• Follow, rate, and review us in your listening app
• Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe 
• Secure your official TSP merchandise at https://shop.tsp.show/  
• 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/

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

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

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

In this episode, you will:

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

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

The Pact 

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

• 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/