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Cheeky Pint

Stripe
Artificial Intelligence
Stripe
Healthcare
Stablecoins
Matx
Saas
AGI
Meta
Zipline
Rivian
Google Tpus
Chip Manufacturing
AI Coding Tools
Solar Energy
Restaurant Industry
Openai
Education System
CFO Role
Home Robotics
Reality Labs

Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.

PublishesWeeklyEpisodes34Founded10 months ago
Number of ListenersCategories
TechnologyEntrepreneurshipBusiness

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Artwork for Cheeky Pint

Latest Episodes

Tony Xu, cofounder and CEO of DoorDash, joins John for a pint to discuss how they won a crowded market by obsessing over retention and the reality of fighting fraud in the physical world. They cover the harsh economics of the restaurant industry, why... more

Mati Staniszewski is the co-founder of ElevenLabs, the research company making audio accessible across languages and voices. He sits down with John to discuss the "voice Turing Test" and why AI has conquered text but still struggles with conversation... more

Sundar Pichai is the CEO of Google and Alphabet. He sits down with John and Elad Gil to discuss Google’s resurgence in the AI race, managing a massive $180 billion CapEx budget, and why 2026 is the year of the supply crunch. They cover the constraint... more

Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vitamin vs painkiller” dynamic, the drama behind their famous 101-billboard campaign, and why she believes... more

Key Facts

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Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Tony Xu
Co-founder and CEO of DoorDash
DoorDash
Episode: The economics and trends of the restaurant industry, with Tony Xu of DoorDash
Mati Staniszewski
Co-founder of ElevenLabs
ElevenLabs
Episode: The world of voice AI, with Mati Staniszewski of ElevenLabs
Sundar Pichai
CEO of Google, leading AI strategy and productization
Google/Alphabet
Episode: The history and future of AI at Google, with Sundar Pichai
Christina Cacioppo
Founder of Vanta, CEO
Vanta
Episode: Compliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
Dmitri Dolgov
Co-CEO of Waymo, former lead of Google self-driving car project
Waymo
Episode: The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
Tarek Mansour
Co-founder of Kalshi
Kalshi
Episode: Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Luana Lara
Co-founder of Kalshi
Kalshi
Episode: Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Bret Taylor
Chairman of the OpenAI board; founder and CEO of Sierra
Sierra; OpenAI
Episode: Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Garrett Langley
Founder and CEO of Flock Safety
Flock Safety
Episode: Garrett Langley of Flock Safety on building technology to solve crime

Host

John Collison
Co-founder of Stripe; host of Cheeky Pint

Reviews

4.8 out of 5 stars from 90 ratings
  • In-depth discussion but lacks a clear Identity.

    Loved the pod but questions, discussion points and views are pretty repetitive.

    Apple Podcasts
    4
    TradingAssasin
    India4 months ago
  • Host is very smart

    He should start a payments company or something; seems very knowledgeable

    Apple Podcasts
    5
    edwinarbus
    United States5 months ago
  • Please change this

    I love this show, but the transition sound to commercial sounds just like the Doppler effect of a car horn speeding towards you. It gives me a heart attack every time. Users first.

    Apple Podcasts
    1
    Anonymous college kid
    United States7 months ago
  • Longer is better

    Great show

    Apple Podcasts
    5
    Avid pod listener7
    United States7 months ago
  • A question

    Why do you have to add Stripe cofounder for your identity here?

    Apple Podcasts
    3
    Many Nakamura
    India9 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Some listeners note transitions can be abrupt or have sound effects that take getting used to.
Thoughtful, probing conversations with strong guests and clear questions.
Guests bring practical, real-world insights and useful takeaways.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#41
United States/Technology
Apple Podcasts
#23
United Kingdom/Technology
Apple Podcasts
#37
Canada/Technology
Apple Podcasts
#53
Australia/Technology
Apple Podcasts
#62
Germany/Technology
Apple Podcasts
#122
Italy/Technology

Talking Points

Recent interactions between the hosts and their guests.

The world of voice AI, with Mati Staniszewski of ElevenLabs
Q: What is the difference between cascaded voice systems and speech-to-speech models, and when might each be used?
Cascaded systems use separate transcription (speech-to-text), language processing (LLM), and synthesis (text-to-speech) to allow modularity and better integration with other systems, offering reliability and controllability; speech-to-speech models bypass intermediate text for lower latency, but sacrifice some reliability and require smaller models, making them suitable for low-latency, lighter-weight tasks or where end-to-end latency is critical.
The world of voice AI, with Mati Staniszewski of ElevenLabs
Q: What are the two big innovations that enabled modern voice models?
The two big innovations are (1) encoding/decoding the voice features to create reliable, high-quality vocal representations, and (2) incorporating context so the model can adjust pronunciation, emotion, and prosody based on surrounding text and prior speech, enabling natural, expressive output.
The world of voice AI, with Mati Staniszewski of ElevenLabs
Q: Describe at a high level how an audio model works in relation to how LLMs work with text.
The speaker explains that audio models rely on encoding and decoding voice features, such as phonemes and spectrogram representations, and incorporate context across speaking style, dialect, emotion, and prosody. They contrast this with text-based LLMs by highlighting the need to map text to audio via speakers' embeddings and to leverage both phoneme and text information for real-time generation and quality.
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
Q: What are the most important factors when expanding from a single city to global deployment, and how does the tech adapt to different operating domains?
Expansion hinges on validating core capabilities across diverse operating domains (weather, density, road types) and then adapting with data collection, domain-specific validation, and some hardware/software tweaks. The core technology generalizes well, but deployment requires careful domain adaptation and safety validation in each new city.
The 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
Q: Why did Waymo shift to a larger AI backbone for the fifth generation rather than continuing with many small subsystems?
The shift to a stronger AI backbone—using larger, high-capacity off-board models like the Waymo driver, simulator, and critic—allowed for better generalization, easier scaling, and more cohesive training and evaluation. This enabled a faster, more reliable path to full autonomy than relying on a patchwork of smaller subsystems.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About Cheeky Pint

What is Cheeky Pint about and what kind of topics does it cover?

A candid, tech-forward interview series where founders, builders, and leaders share practical insights from starting up to scaling, often touching on regulatory, governance, and market-shaping implications. Conversations span prediction markets, AI governance, safety tech, energy innovation, and financial infrastructure, with a common thread of translating complex technologies into real-world impact. Listeners can expect thoughtful questions, problem-solving mindset, and relatable founder journeys, all anchored by a casual, conversational vibe over a pint. A standout hallmark is exploring high-stakes tradeoffs between regulation, growth, and responsible innovation across diverse industries, making it useful for executives, product/tech lead... more

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How many episodes of Cheeky Pint are there?

Cheeky Pint launched 10 months ago and published 34 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Cheeky Pint?

Recent guests on Cheeky Pint include:

1. Tony Xu
2. Mati Staniszewski
3. Sundar Pichai
4. Christina Cacioppo
5. Dmitri Dolgov
6. Tarek Mansour
7. Luana Lara
8. Bret Taylor

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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