Brandon Whichard

Episode 585: I'm not a total AI hater, I'm a finance hater

August 14th, 2026  |  1 hr 4 mins

This week, we discuss Zuckerberg's open source AI manifesto, GPUs as securitizable assets, and who actually gets AI ROI. Plus, Buc-ee's goes to war over beavers.

Episode 584: It’s All God Throwing Dice

August 7th, 2026  |  48 mins 41 secs

This week, we discuss the Situational Awareness meltdown, Airtable getting sold, and review the Java documentary. Plus, what you should actually buy at IKEA.

Episode 583: HuggingFace make me gazpacho

July 31st, 2026  |  1 hr 3 mins

This week, we discuss how normal people use AI, Alphabet's Anthropic-fueled earnings, and skills vs. agents. Plus, catching AI-cheating students with a hidden prompt.

Episode 582: Talking About Modernization

July 24th, 2026  |  1 hr 6 mins

This week, we discuss Bun's move to Rust, OpenAI hunting for revenue, and Stripe's bid for PayPal. Plus, Coté's Dad wisdom.

Episode 581: Arjun Iyer on Shipping Faster with Ephemeral Environments and AI Agents

July 17th, 2026  |  51 mins 19 secs

interview

Brandon interviews Arjun Iyer, CEO & Co-founder of Signadot. They discuss how Ephemeral Environments eliminate developer toil by shifting validation earlier in the dev cycle, how Signadot's MCP server lets AI coding agents run end-to-end tests autonomously, and real-world results including Brex saving $2M in cloud spend. Plus, how Cisco bought AppDynamics for ~$4 billion the day before their IPO.

Episode 580: Varlock: Bringing Order to the Chaos of Environment Variables

July 10th, 2026  |  54 mins 34 secs

interview

Every project has environment variables. Almost nobody manages them well. This week Brandon talks with Phil Miller and Theo Ephraim, who built varlock to fix that — bringing structure and security to the humble .env file.

Episode 579: The Headless Lifestyle

July 3rd, 2026  |  1 hr 11 mins

This week, we discuss Anthropic's 18-day Fable timeout, whether AI is actually killing jobs, and OpenAI's trillion-dollar IPO problem. Plus, SoftBank's golden goose slides.

Episode 578: War for Talent

June 26th, 2026  |  1 hr 4 mins

This week, we discuss Fable follow-up, Gartner's AI Governance MQ, and the war for AI talent. Plus, Matt and Brandon review "Disclosure Day."

Episode 577: Let’s go to Buc-ee’s

June 19th, 2026  |  1 hr 29 secs

This week, we discuss the Fable ban, SpaceX's $60B Cursor buy, and why Lovable wins when AI picks your stack. Plus, Europeans are at the World Cup and already drank Boston dry.

Episode 576: Observability's Next Phase

June 12th, 2026  |  48 mins 39 secs

interview

Brandon talks with OpenObserve's Prabhat Sharma and Shani Shoham: why observability is still broken, how they fixed it, and where AI takes it next.

Episode 575: UI blizzard

June 5th, 2026  |  1 hr 1 min

This week, we discuss NVIDIA going consumer, Microsoft Build, and the Anthropic/OpenAI IPO race. Plus, does credit card insurance work?

Episode 574: Nobody Wants to Be a Measurer

May 29th, 2026  |  1 hr 1 min

This week, we discuss the Cloudflare CEO's op-ed, upcoming tech IPOs and GitHub getting breached. Plus, ranking our favorite manifestos.

Episode 573: How many quadrillions in a Googol?

May 22nd, 2026  |  1 hr 2 mins

This week, we discuss Google I/O, the OpenAI soap opera, and ChatGPT going full financial advisor. Plus, thoughts on improving the conference hallway track.

Episode 572: The world isn’t curl

May 15th, 2026  |  1 hr 53 secs

This week, we discuss how security gets sold to execs, where agentic coding and security collide, and Cloudflare vs. Datadog's diverging paths. Plus, Coté weighs in on sugar cookies.

Episode 571: The Enterprise Dunbar number

May 8th, 2026  |  58 mins 9 secs

This week, we discuss AI labs driving cloud revenue, hyperscalers laying off instead of building, and kids defeating age verification. Plus, Brandon has too many thoughts on Workday.

Episode 570: The Enterprisification of Agents

May 1st, 2026  |  1 hr 10 mins

This week, we discuss Google's enterprise agent stack, what makes an agent an agent, and AI's biggest critic. Plus, Coté wants better vision.