The Startup Podcast

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

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

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

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

In this episode, you will:

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

The Pact

• Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
• Follow, rate, and review us in your listening app
• Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe
• Secure your official TSP merchandise at https://shop.tsp.show/
• 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/

#Resilience #Startups #Founder #TheStartupPodcast #Mindset

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

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

In this episode, you will:

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

The Pact 

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

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

Key links

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

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

Learn more about Chris and Yaniv

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

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

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

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

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

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

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

In this episode, you will:

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

The Pact

• Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
• Follow, rate, and review us in your listening app
• Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe
• Secure your official TSP merchandise at https://shop.tsp.show/
• Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg
• Give us a public shout-out on LinkedIn or anywhere you have a social media following

Key links

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

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

Learn more about Chris and Yaniv

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

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

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

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

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

Google’s long-running antitrust case has reached its remedy stage, and the outcome was far lighter than many expected. No breakup, no ban on default search deals, just a few constraints on bundling apps and some required data sharing, but it may not be quite as simple as it seems on the surface.

Meanwhile, OpenAI dropped $1.1 billion to acquire Statsig, a product analytics company. What are the details of the deal, and what does it reveal about the future of OpenAI?

To top the week off, Y Combinator released its Fall 2025 Request for Startups, and the lineup is surprisingly AI-heavy. Is this really a good indicator of successful startups, or are YC missing the mark with this one? Chris and Yaniv discuss this at length, cutting deeply into why these criteria were chosen, what you should (and shouldn’t) listen to, and where founders can looking for investors instead.

In this episode, you will:

• Understand why Google’s “light touch” antitrust remedies sent its stock up 8% overnight
• Learn what OpenAI’s Statsig acquisition signals about its long-term strategy
• Explore why YC’s latest startup requests are so heavily AI-focused, and why that’s a mistake
• Compare today’s antitrust rulings with the Microsoft case of the 1990s
• Discover how AI may disrupt not just tech, but also government consulting and enterprise software
• Get Yaniv’s insider view on why intent-driven marketplaces may be the next frontier

The Pact 

• Honor the Startup Podcast Pact! If you have listened to TSP and gotten value from it, please:
• Follow, rate, and review us in your listening app
• Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe 
• Secure your official TSP merchandise at https://shop.tsp.show/  
• Follow us here on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg 
• Give us a public shout-out on LinkedIn or anywhere you have a social media following

Key links

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

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

Learn more about Chris and Yaniv

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

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

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

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

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

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

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

In this episode, you will:

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

The Pact

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

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

Key links

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

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

Learn more about Chris and Yaniv

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

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

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

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

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

Is Apple’s dominance in smartphones starting to crack? Google’s Pixel 10 launch brought AI-first features, polished hardware, and bold marketing, signaling a new era in the iPhone vs. Android rivalry.

For years, the iPhone has been synonymous with polish, hardware quality, and ecosystem lock-in. But with Google’s patient, decade-long investment in the Pixel line, coupled with deep AI integration, the balance may be shifting.

Today, Chris and Yaniv analyze Pixel 10’s hardware updates, AI-powered OS features, and how Google’s persistence has brought it head-to-head with Apple.

For founders and entrepreneurs, they also offer their unique insight into startups and unpack what you can learn about patience, platform strategy, and design in the middle of a platform shift.

In this episode, you will:

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

The Pact 

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

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

Key links

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

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

Learn more about Chris and Yaniv

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

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

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

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

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

What makes a great tech infrastructure startup? And how do the best ones successfully navigate, and stand out from, the overcrowded market?

In this episode, Yaniv is joined by Joseph Ruscio, General Partner at Heavybit and former CTO of Vibrato, to unpack the dos and don'ts of tech infrastructure startups, how open source fuels growth, and why AI is changing the way software is built.

With over 20 years in system software and a portfolio including LaunchDarkly, Netlify, and PagerDuty, Joe brings a front-row perspective to the future of startup building. The conversation dives into bottom-up growth, developer adoption, and the open source strategies that give founders leverage—and how AI agents are reshaping the role of the software engineer.

In this episode, you will:

• Understand why bottom-up adoption often beats enterprise sales for startup growth
• Learn how AWS scaled from startups to Fortune 500s—and what founders can copy
• Discover the power of open source as a go-to-market strategy (and its pitfalls)
• See why giving away your product can actually accelerate growth and community adoption
• Explore how AI is changing developer workflows and the future role of engineers
• Identify the risks of being “too close to your own pain” as a technical founder
• Apply practical guidelines for choosing your startup’s tech stack without overthinking

DevGuild Open Source: http://heavybit.com/devguild/open-source 

The Pact 

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

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

Key links

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

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

Learn more about Chris and Yaniv

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

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

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

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

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

Is the AI hype cycle about to burst?

For months, investors and founders have chased sky-high valuations, billion-dollar hires, and promises of superintelligence, but Meta's drastic plans to cut back its AI division seem to indicate a bleak future for LLMs and AI at large.

In this episode, Chris and Yaniv unpack the latest shakeup at Meta, using their knowledge and experience in Silicon Valley to analyze the situation and pick apart whether this is a canary in a coal mine. They explore why Meta is restructuring, what it says about the state of large language models (LLMs), and how to navigate high-stakes moments when the hype cycle turns.

In this episode, you will:

• Understand what Meta’s latest AI restructure really signals about industry priorities
• Learn why hype cycles always lead to a trough of disillusionment, and how to prepare
• Explore how trillion-dollar bets on AGI could reshape competitive dynamics
• See why founders should question assumptions about LLM productivity gains
• Recognize the risks of chasing hype versus building sustainable business models

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/

This new era of AI-driven startups has many founders still believing success is about having the perfect product roadmap. The truth, however, is far more counterintuitive.

In this episode, Yaniv and Chris dive into timeless lessons from Paul Graham’s legendary essay “Startups in 13 Sentences”. Drawing from Graham’s wisdom and their own experiences, they break down why co-founders matter more than ideas, why “launch fast” is the golden rule, and why understanding users is harder (and more important) than chasing growth.

In this episode, you will:

• Learn why choosing the right co-founder is the most important decision you’ll ever make
• Understand why launching fast is less about speed and more about learning from real users
• Discover why evolving your idea matters more than defending a perfect plan
• See how understanding users drives sustainable growth (and why chasing vanity metrics kills startups)
• Explore why great customer service that 'doesn’t scale' is actually a secret weapon
• Unpack the dangers of measuring the wrong things and how to track what truly matters
• Find out why distractions (even profitable ones) are the silent killers of young startups

For founders serious about building in the AI era, these lessons, though written 16 years ago, are more relevant than ever. Startups succeed not by following conventional wisdom, but by mastering the counterintuitive truths that define Silicon Valley’s greatest companies.

Read Paul Graham's "Startups in 13 Sentences" here: https://paulgraham.com/13sentences.html

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/