Cheeky Pint

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 to list election markets, and how they are building the "New York Stock Exchange of events." They cover why prediction markets are an antidote to social media polarization, the mechanics of market making for culture, and their vision for trading everything from GPU shipments to the Oscars and the weather.

Timestamps
(00:01:39) Suing the government
(00:14:42) Why now?
(00:17:12) Kalshi by numbers
(00:20:58) Solving market making
(00:31:33) Agentic trading
(00:33:43) Sharps
(00:38:45) Stripe Connect
(00:39:33) Evolving Kalshi
(00:44:50) Who loses from Kalshi?
(00:47:35) Insider trading
(00:53:28) The ethics of sports contracts
(00:58:08) New derivatives
(01:04:27) Politics
Article(s):
On the Observational Implications of Knightian Uncertainty – Kevin Hassett & Weifeng Zhong (AEI)
The 2028 Global Intelligence Crisis – Citrini Research

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 believes the atomic unit of AI productivity is a process, not a person. They cover why big companies struggle to adopt AI because they are “shipping their org charts.” Bret also discusses a new type of hyper-generalist, reflects on his experience with the OpenAI and Twitter boards, and explains why he believes we might see the end of the smartphone era.

Timestamps
(00:00:26) Coding
(00:16:23) Sierra
(00:27:14) Agentic UX
(00:38:47) Building support agents
(00:45:43) Co-developing with the models
(00:50:08) SaaSpocalypse
(01:00:50) Stripe Sessions
(01:01:33) Outcome-based pricing
(01:09:14) Is Sierra short AGI?
(01:13:50) AI productivity
(01:23:47) How to structure a tech business
(01:30:25) Board drama
(01:38:24) AI predictions

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 million crimes a year, and the engineering challenges of building solar-powered cameras and autonomous drones. They cover the shifting landscape of criminal technology, why hardware requires making "one-way door" decisions, and his vision for a future where technology prevents crime before it happens.
Timestamps
(00:00:19) Flock
(00:19:51) Safety vs privacy
(00:23:54) Crime and technology
(00:32:36) Crime rates
(00:43:56) Corporate security
(00:52:16) Stripe Radar
(00:52:54) Competitive landscape
(01:02:41) Drones
(01:09:01) The Flock business
(01:11:39) Building hardware
(01:20:01) Cameras
(01:25:17) PD procurement
(01:32:56) Building your own drones
(01:40:52) What’s next for Flock?
Books:
The Digital Silk Road: https://www.amazon.com/Digital-Silk-Road-Chinas-Future/dp/0063046288
Boyd: https://www.amazon.co.uk/Boyd-Fighter-Pilot-Who-Changed/dp/0316796883

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 trade-off" between latency and throughput for current chips, why MatX is betting on combining HBM and SRAM to solve it, and the massive logistical challenge of manufacturing chips at scale with TSMC. Reiner also shares his predictions for AI in 2027, why he prefers Rust for hardware design, and why the best iteration loops happen in your head before writing a line of code.
Timestamps
(00:00:15) Google’s AI revival
(00:07:54) MatX
(00:17:11) AI supply chain
(00:21:48) Designing chips
(00:37:11) TSMC
(00:44:17) Token pricing
(00:44:55) RL-ing chip design
(00:49:26) Design to production
(00:56:05) MatX culture
(01:02:57) Rust
(01:05:21) Cuckoo hashing
(01:09:35) Unexplored model architectures

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.
Our annual letter covers the trends that we think are worth paying close attention to as the pace of change accelerates.
Timestamps
(01:48) The sorting machine
(05:45) Global by default
(09:01) Stable progress
(12:14) Working capital’s working. Capital!
(15:09) Escaping from low revenue mode
(18:33) The five levels of agentic commerce
(23:52) A Republic of Permissions