Brandon Whichard

Episode 535: Don’t put randomness in your workflow

August 29th, 2025  |  51 mins 24 secs

This week, we discuss AI disillusionment, the good and bad of AI use cases, and VMware news. Plus, we compare tech mergers to Taylor Swift’s engagement.

Episode 534: Capitalism is working

August 22nd, 2025  |  1 hr 22 mins

This week, we discuss the US backing Intel, SaaS staying power, and AI’s impact on deep work. Plus, Matt Ray’s moving tips and more kolache talk in the after show.

Episode 533: It’s a Type 2 Kolache

August 15th, 2025  |  1 hr 6 mins

This week, we discuss GPT 5.0, the emerging AI ecosystem, and why TAM is basically a bedtime story for investors. Plus, Coté serves up a masterclass on kolaches.

Episode 532: Less Goofy. More Enterprise.

August 8th, 2025  |  1 hr 6 mins

This week, we discuss cloud earnings, what’s driving valuations, and why AWS says it’s still early innings for cloud. Plus, Coté does a deep dive on Shipley Donuts.

Episode 531: YAYAML

August 1st, 2025  |  59 mins 5 secs

This week, we discuss the AI hype cycle, Astronomer’s viral moment, and yet another YAML flavor — KYAML. Plus, private equity is coming for your donuts.

Episode 530: His proper name is Sasquatch

July 25th, 2025  |  47 mins 37 secs

This week, we cover AI going rogue, Cloudflare declaring independence, and the secure container craze. Plus, Matt bravely judges 9 new emoji.

Episode 529: Windsurf, AI Agents, and Kiro

July 18th, 2025  |  47 mins 3 secs

This week, we discuss Windsurf being acquired (again), how much AI agents really help with coding, and AWS launching Kiro. Plus, Matt attempts to design a new closet.

Episode 528: You can’t spell Clippy without CLI

July 11th, 2025  |  1 hr 9 mins

This week, we discuss the return of command line tools, Kubernetes embracing VMs, and the steady march of Windows. Plus, thoughts on TSA, boots, and the “old country."

Episode 527: Victor Adossi on WebAssembly

July 4th, 2025  |  1 hr 6 mins

interview

Brandon interviews Victor Adossi, an engineer at Cosmonic. They discuss the state of WebAssembly, wasmCloud, and why Wasm is poised for growth. Plus, Victor shares what it’s like to live as an expat in Japan.

Episode 526: The Optimist, the Origin, and the Deck

June 27th, 2025  |  1 hr 12 mins

This week, we unpack "The Optimist", the new Sam Altman biography; revisit OpenAI’s early days; and break down Coatue’s AI strategy deck. Plus, tips for squeezing in side projects between thought leadership presentations.

Episode 525: AI Native vs. AI Add-on

June 25th, 2025  |  15 mins 49 secs

short

This week, we try a shorter format inspired by the Dithering podcast. The conversation digs into the difference between apps built with AI from the ground up and those with AI bolted on after the fact.

Episode 524: It’s a Box in a Box

June 20th, 2025  |  1 hr 3 mins

This week, we cover Apple’s WWDC updates—from containerization to Foundation Models—and the Linux Foundation’s new FAIR Package Manager. Plus, we crown the best SDT Uber rider.

Episode 523: Sterling Chin on APIs, AI, and Building MCP Servers

June 13th, 2025  |  1 hr 9 mins

interview

Brandon talks with Sterling Chin, Senior Developer Advocate at Postman, about building great APIs, why AI needs APIs, and what’s new at Postman. Plus, hear how he made the leap from 3rd-grade teacher to dev advocate.

Episode 522: A 5-star cannot stand

June 6th, 2025  |  1 hr 20 secs

This week, we discuss Apple reversioning macOS, the steady state of private cloud, and Snowflake’s acquisition of CrunchyData. Plus, the eternal quest for a 5-star Uber rating.

Episode 521: The MacGuffin

May 30th, 2025  |  1 hr 4 mins

This week, we discuss OpenAI acquiring io, Salesforce buying Informatica, and the future of AI agents. Plus, Coté shares details about a sensitive procedure and ceiling puzzles.

Episode 520: Excited is overused

May 23rd, 2025  |  1 hr 3 mins

This week, we recap Microsoft Build, Google I/O, and Java turning 30. Plus, more Vegemite talk and a discussion on whether tech presenters really need to tell us they’re “excited.”