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Cheeky Pint

Stripe
Artificial Intelligence
Healthcare
AGI
Meta
Zipline
AI Coding Tools
Education System
Openai
CFO Role
Reality Labs
Resource Allocation
Home Robotics
Digital Nomad
Venture Capital
Coding
Coinbase
Bitcoin
Scott Wu
Drone Delivery
American Agriculture

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

PublishesWeeklyEpisodes28Founded9 months ago
Number of ListenersCategories
TechnologyBusinessEntrepreneurship

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Artwork for Cheeky Pint

Latest Episodes

Bret Taylor, co-founder of Sierra and Chair of the OpenAI board, joins John for a pint to discuss the rapid shift toward an agentic future. In this episode, Bret explains why outcome-based pricing is the future of software business models, and why he... more

Garrett Langley is the founder and CEO of Flock Safety, a public safety operating system that helps communities and law enforcement eliminate crime. He sits down with John to discuss why most crime is opportunistic, how Flock helps clear over one mil... more

Reiner Pope is the co-founder and CEO of MatX, designing specialized chips for Large Language Models. A former Google TPU architect, he joins John to discuss why the current generation of AI hardware is hitting a wall. They cover the "uncomfortable t... more

The internet economy accelerated in 2025. The fastest-growing companies got even faster, agentic commerce and stablecoin payments started to kick into gear, and total payment volume on Stripe grew by a third as our customers continued to prosper.

Ou... more

Key Facts

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

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Recent Guests

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
Zach Abrams
Founder of Bridge, a stablecoin orchestration platform.
Bridge
Episode: Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Henri Stern
Founder of Privy, a digital wallet infrastructure provider.
Privy
Episode: Stablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Casey Handmer
Founder of Terraform Industries, developing technology to produce synthetic natural gas from sunlight and air.
Terraform Industries
Episode: Casey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
Mackenzie Burnett
CEO and co-founder of Ambrook, providing financial tools for farms.
Ambrook
Episode: Ambrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
Keller Cliffton
Co-founder and CEO of Zipline
Zipline
Episode: Zipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
Vlad Tenev
CEO and co-founder of Robinhood
Robinhood
Episode: Robinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman
Susan Li
CFO of Meta, joined the company in 2008 and became CFO in 2022.
Meta
Episode: Meta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM

Host

John Collison
Co-founder of Stripe and host. Experienced in the tech and finance sectors, providing valuable insights into entrepreneurship and innovation.

Reviews

4.9 out of 5 stars from 88 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
    India3 months ago
  • Host is very smart

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

    Apple Podcasts
    5
    edwinarbus
    United States3 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 States6 months ago
  • Longer is better

    Great show

    Apple Podcasts
    5
    Avid pod listener7
    United States6 months ago
  • A question

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

    Apple Podcasts
    3
    Many Nakamura
    India8 months ago

Listeners Say

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

The podcasts' format encourages engaging conversations that feel both informative and casual.
Listeners appreciate the quality and relevance of discussions with leading figures in business and technology.
Some listeners pointed out the abruptness of transitions, which can be jarring.

Chart Rankings

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

Apple Podcasts
#40
United States/Technology
Apple Podcasts
#34
Canada/Technology
Apple Podcasts
#35
United Kingdom/Technology
Apple Podcasts
#31
Australia/Technology
Apple Podcasts
#73
France/Technology
Apple Podcasts
#192
Germany/Technology

Talking Points

Recent interactions between the hosts and their guests.

Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Q: What is Sierra, and how is it changing customer experience with AI agents?
Sierra builds AI agents that can take over customer interactions across channels (phone, chat, WhatsApp) and perform actions on behalf of customers, not just answer questions. They focus on end-to-end journeys and aim to unify disparate systems into a single agent-driven experience, which can improve metrics like NPS and shorten service paths.
Garrett Langley of Flock Safety on building technology to solve crime
Q: How does Flock balance privacy concerns with safety benefits, and what data retention policies exist?
The guest argues for accountability and audits, noting data retention windows (e.g., 7 days for live video, 30 days for license-plate data) and supports legislated limits, audits, and warrants to manage civil liberties while enabling public safety.
Reiner Pope of MatX on accelerating AI with transformer-optimized chips
Q: What are your AI predictions for 2026?
I'm excited about expanding into more domains, particularly in areas where models can be optimized for performance based on the changing hardware landscape.
Reiner Pope of MatX on accelerating AI with transformer-optimized chips
Q: You guys just raised a big new round of financing. Can you tell me about that?
We've raised a $500 million Series B round led by Jane Street and Situational Awareness to ramp up manufacturing and supply chain for our chip.
Reiner Pope of MatX on accelerating AI with transformer-optimized chips
Q: What is MatX? How did you guys start it, and which part of this space are you attacking?
MatX is making the best chips physically possible for LLMs, focusing on supporting much larger matrices and lower precision arithmetic.

Audience Metrics

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

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
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Frequently Asked Questions About Cheeky Pint

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

Conversations from a range of successful founders and industry leaders take center stage, often exploring themes of technology, entrepreneurship, and product innovation. Episodes feature candid dialogues that encapsulate personal journeys, lessons learned in building companies, and insights on current industry trends. Notable topics include renewable energy, financial technology, and advancements in artificial intelligence, each discussed in the context of how they reshape markets and impact society. The unique format of pairing discussions with a casual drink fosters a relaxed environment, likely making it appealing to both professionals and enthusiasts looking for in-depth knowledge shared in an accessible manner.

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How many listeners does Cheeky Pint get?

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To see how many followers or subscribers Cheeky Pint has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

Which podcasts are similar to Cheeky Pint?

These podcasts share a similar audience with Cheeky Pint:

1. Dwarkesh Podcast
2. The a16z Show
3. Capital Allocators – Inside the Institutional Investment Industry
4. All-In with Chamath, Jason, Sacks & Friedberg
5. Business Breakdowns

How many episodes of Cheeky Pint are there?

Cheeky Pint launched 9 months ago and published 28 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Cheeky Pint?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

Where can I see ratings and reviews for Cheeky Pint?

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What guests have appeared on Cheeky Pint?

Recent guests on Cheeky Pint include:

1. Bret Taylor
2. Garrett Langley
3. Zach Abrams
4. Henri Stern
5. Casey Handmer
6. Mackenzie Burnett
7. Keller Cliffton
8. Vlad Tenev

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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