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Cheeky Pint

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

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

PublishesWeeklyEpisodes31Founded10 months ago
Number of ListenersCategories
BusinessEntrepreneurshipTechnology

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Latest Episodes

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

Waymo is now doing nearly 500,000 rides a week across 10 cities. Co-CEO Dmitri Dolgov came to the pub to discuss how they moved from scientific research to massive global scaling. He gives a masterclass on the sensor stack (and why you still need Lid... more

Tarek Mansour and Luana Lopes Lara are the co-founders of Kalshi, the first federally regulated prediction market in the US. They sit down with John and Matt Huang to discuss growing their revenue 11x in six months, why they sued their own regulator ... more

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

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Recent Guests

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
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

Host

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

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 States4 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 States7 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.

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
#65
United States/Technology
Apple Podcasts
#27
United Kingdom/Technology
Apple Podcasts
#59
Canada/Technology
Apple Podcasts
#58
Australia/Technology
Apple Podcasts
#158
Germany/Technology
Apple Podcasts
#232
Italy/Technology

Talking Points

Recent interactions between the hosts and their guests.

Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Q: What is your stance on the future policy direction for prediction markets?
We advocate for a balanced approach: promote innovation and US leadership while strengthening regulation to ensure fairness, transparency, and consumer protection, including stricter insider trading rules and public trade data for auditability.
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Q: How do you think about market structure and liquidity for the long tail of markets vs. high-demand markets?
We incentivize liquidity differently: for long-tail markets we offer liquidity incentives and uptime requirements to attract market makers, while for high-demand markets we favor broker connections and cost-effective execution to ensure stable liquidity and competitive pricing.
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Q: What was the turning point that led to winning the election market lawsuit and scaling the business?
The turning point came when the court recognized that elections do not fall within the government-imposed prohibitors under the law, validating Kalshi's legal framework and enabling us to trade election contracts in the US, which dramatically accelerated growth.
Creating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Q: Can you just tell a little bit the story of how you started Kalshi and the approval process?
We started Kalshi in 2019 and spent three years obtaining regulatory approval before launching in 2022, focusing on a legal, credible path rather than offshore alternatives; we believed this was essential for mainstream adoption and risk management.
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.

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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Which podcasts are similar to Cheeky Pint?

These podcasts share a similar audience with Cheeky Pint:

1. Uncapped with Jack Altman
2. Dwarkesh Podcast
3. Invest Like the Best with Patrick O'Shaughnessy
4. The a16z Show
5. No Priors: Artificial Intelligence | Technology | Startups

How many episodes of Cheeky Pint are there?

Cheeky Pint launched 10 months ago and published 31 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. Tarek Mansour
2. Luana Lara
3. Bret Taylor
4. Garrett Langley
5. Zach Abrams
6. Henri Stern
7. Casey Handmer
8. Mackenzie Burnett

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