Cheeky Pint

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 "market sizing is bullshit." They cover the tension between vibe coding and rigorous security, how Vanta is using agents to generate UI, and why the best founders are relentless truth-seekers.

Timestamps
(00:00:17) Vanta
(00:12:30) How compliance works
(00:15:06) Breaches
(00:23:52) Stripe Tax
(00:24:43) AI and compliance
(00:44:50) Go-to-market
(00:47:22) Lessons from USV

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 Lidar), how they use "Simulation" and "Critic" models to train the AI, and why he believes cars that require human supervision will never naturally evolve into robotaxis. They also cover the new custom-built vehicle that feels like a living room, the economics of ride-hailing in rural Alaska, and the "Russian math nerd" diaspora that seems to run the UK tech scene.
Timestamps
(00:00:22) Russia
(00:02:51) Waymo architecture
(00:09:59) Why now?
(00:19:46) Driving nuance
(00:29:37) Stripe Agentic Commerce Suite
(00:30:17) Hardware
(00:40:20) Emergent behavior
(00:46:36) Scaling
(00:57:56) Google

Article:
EMMA: End-to-End Multimodal Model for Autonomous Driving – Waymo Research: https://waymo.com/research/emma/

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