iiinova — where your digital self keeps evolving

Brandon Whichard @brandonwhichard.com · 25/09/2026

Why did Sun really fail? We also get into the New Kingmakers becoming agents and AI doom brackets on the latest episode.

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Brandon Whichard @brandonwhichard.com · 18/09/2026

AI doom odds, a WordPress boardroom coup, and Meta's Muse assistant — a lot going on in tech this week.

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Brandon Whichard @brandonwhichard.com · 11/09/2026

VS Code got a documentary, Ed Zitron's having a moment, and someone put a number on AI extinction risk. Lots to discuss this week.

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Brandon Whichard @brandonwhichard.com · 08/09/2026

@jasonkirk.fyi If you think SMU winning with a -3 turnover margin against FSU is unusual, check out last year's SMU vs. Duke game where SMU was -6 in turnover margin and won. Being an SMU fan is exciting! 😂

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Brandon Whichard @brandonwhichard.com · 06/09/2026

Vitamin or painkiller? That's the framing Brian, Aaron, and I used on this week's Enterprise AI Show to talk about why AI transformation still needs a burning platform — and why personal productivity gains aren't showing up at the org level.

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Brandon Whichard @brandonwhichard.com · 04/09/2026

If AI agents are forming their own civilizations, why can't one just do my taxes? That and Chainguard vs. IBM's Lightwell on the latest episode.

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Brandon Whichard @brandonwhichard.com · 02/09/2026

Went on The Enterprise AI Show to talk NVIDIA's record quarter and Hugging Face acquisition, Stripe's OpenRouter deal, unsettling OpenAI agent tests, and Salesforce's Claudeforce.

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Brandon Whichard @brandonwhichard.com · 28/08/2026

Stripe wrote a letter about the singularity and then spent $8B on OpenRouter. We break down what that actually means, plus AI job anxiety.

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Brandon Whichard @brandonwhichard.com · 26/08/2026

I sat down with Rich Ziade to talk about why AI projects fail without real discovery, why "agents" are massively oversold, and why transformation still comes down to hard conversations, not new tools.

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Brandon Whichard @brandonwhichard.com · 24/08/2026

Are GPUs becoming a real "asset class" — or are we watching the next bubble get built in real time?

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Brandon Whichard @brandonwhichard.com · 21/08/2026

The unsung genius of Apple Pay, why AI watermarking matters, and why digital transformation only seems to happen when there's a crisis. Plenty to dig into this week.

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Brandon Whichard @brandonwhichard.com · 19/08/2026

A question more enterprises need to be asking: own your model weights, or rent them? We got into it on the latest episode.

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Brandon Whichard @brandonwhichard.com · 16/08/2026

Is open-source AI on the decline? I went on The Enterprise AI Show to talk through the market trends, the money problems, and where open models go from here.

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Brandon Whichard @brandonwhichard.com · 14/08/2026

Turns out you can borrow against your GPUs now. We get into that, Zuckerberg's open source AI manifesto, and where the AI ROI is actually landing.

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Brandon Whichard @brandonwhichard.com · 12/08/2026

Went on The Enterprise AI Show with Aaron to talk about whether open source models are quietly losing the AI race.

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Brandon Whichard @brandonwhichard.com · 09/08/2026

I joined Aaron Delp on The Enterprise AI Show to talk about Ed Zitron, the loudest AI skeptic in tech right now. We work through the bear case against AI: where Zitron lands his punches, and where the argument falls apart.

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Brandon Whichard @brandonwhichard.com · 07/08/2026

The Situational Awareness meltdown, Airtable finding a buyer, and yes, we watched the Java documentary. Lots to get into this week.

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Brandon Whichard @brandonwhichard.com · 02/08/2026

Always good to be on The Enterprise AI Show.

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Brandon Whichard @brandonwhichard.com · 31/07/2026

How normal people actually use AI, Alphabet's Anthropic-powered earnings, and the skills vs. agents debate this week.

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Brandon Whichard @brandonwhichard.com · 24/07/2026

Bun's Rust rewrite, OpenAI's hunt for revenue, and Stripe possibly buying PayPal. Plenty to dig into this week.

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Brandon Whichard @brandonwhichard.com · 17/07/2026

Signadot's Arjun Iyer joins to talk ephemeral environments, letting AI agents run their own end-to-end tests, and how Brex saved $2M in cloud spend doing it.

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Brandon Whichard @brandonwhichard.com · 10/07/2026

The .env file: every project has one, almost nobody manages it well. This week I sat down with the founders of varlock to talk about fixing that.

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Brandon Whichard @brandonwhichard.com · 03/07/2026

Anthropic's 18-day Fable outage, whether AI is actually killing jobs, and OpenAI's trillion-dollar IPO problem. Lots to discuss this week.

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Brandon Whichard @brandonwhichard.com · 26/06/2026

Who's winning the war for AI talent? We get into that, plus Gartner's new AI Governance MQ and some Fable follow-up.

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Brandon Whichard @brandonwhichard.com · 19/06/2026

SpaceX drops $60B on Cursor, Fable gets banned, and when AI picks your dev stack it picks Lovable. We dig into all of it this week.

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Brandon Whichard @brandonwhichard.com · 12/06/2026

Observability is still broken. OpenObserve's Prabhat Sharma and Shani Shoham explain why — and where AI takes it next.

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Brandon Whichard @brandonwhichard.com · 05/06/2026

NVIDIA going consumer, Microsoft Build, and the Anthropic/OpenAI IPO race. Who gets to the public markets first? Plenty to discuss this week.

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Brandon Whichard @brandonwhichard.com · 29/05/2026

GitHub got breached, the tech IPO queue is building, and Cloudflare's CEO wrote an op-ed. We cover it all.

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Brandon Whichard @brandonwhichard.com · 27/05/2026

Joined the crew at The Enterprise AI Show to go through the biggest AI stories from May. A lot happened.

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Brandon Whichard @brandonwhichard.com · 22/05/2026

OpenAI drama, Google I/O, and apparently ChatGPT is a financial advisor now. Lots to discuss this week.

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Brandon Whichard @brandonwhichard.com · 15/05/2026

How do you actually sell security to execs? We cover that, agentic coding's collision with security, and Cloudflare vs. Datadog taking very different paths this week.

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Brandon Whichard @brandonwhichard.com · 08/05/2026

If AI labs are driving half of cloud revenue, why are the hyperscalers still laying people off? We discuss that contradiction this week.

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Brandon Whichard @brandonwhichard.com · 06/05/2026

Had a good conversation with Brian Gracely covering the AI stories that actually mattered in April. Give it a listen.

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Brandon Whichard @brandonwhichard.com · 03/05/2026

I'm on The Reasoning Show this week for the 2026 AI Draft. Let me know what I got wrong!

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Brandon Whichard @brandonwhichard.com · 01/05/2026

What makes an agent an agent? Google has some answers. We have some follow-up questions. Also: AI's biggest critic gets the full treatment.

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Brandon Whichard @brandonwhichard.com · 24/04/2026

Agents everywhere at Google Cloud Next, Apple's changing of the guard, and Cursor's very complicated acquisition. Lots to discuss this week.

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Brandon Whichard @brandonwhichard.com · 17/04/2026

We dig into Claude's harness, the latest OpenAI drama, and whether Backstage has quietly become shelfware.

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Brandon Whichard @brandonwhichard.com · 10/04/2026

What does it actually take to ship WebRTC at enterprise scale? Talked with Alberto González, CTO of WebRTC.ventures, about voice apps, streaming, and AI on the latest episode.

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Brandon Whichard @brandonwhichard.com · 03/04/2026

Between the Claude Code leak and the Axios supply chain attack, it's been a rough week for trusting software. We also get into locking down coding agents.

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Brandon Whichard @brandonwhichard.com · 29/03/2026

Crossed the streams this week. Brian Gracely and I went through all the AI chaos from March so you don't have to.

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Brandon Whichard @brandonwhichard.com · 27/03/2026

Big bets gone wrong, OpenAI acquiring the Python toolchain, and Claude's favorite tools. The real question this week: should AI agents be shipping bug fixes faster than your human engineers?

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Brandon Whichard @brandonwhichard.com · 26/03/2026

I've been building everything around Claude Code. @bgracely asked me to break down what that actually looks like day-to-day. Turns out, a lot changes.

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Brandon Whichard @brandonwhichard.com · 20/03/2026

NVIDIA GTC, token budgets, and an AWS outage that definitely had nothing to do with AI.

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Brandon Whichard @brandonwhichard.com · 13/03/2026

Turns out Claude Code isn't just for coders. We've been using it to automate newsletters, status reports, and apparently taxes. Plus, Coté has feelings about it.

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Brandon Whichard @brandonwhichard.com · 06/03/2026

Claude Code, Cursor, the future of the SDLC, and somehow Markdown is to blame for all of it. New episode is up.

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Brandon Whichard @brandonwhichard.com · 27/02/2026

Between AI rewriting COBOL and the predicted death of Microsoft Office, we’re covering a lot of ground this week. Plus, we debate if TSA PreCheck Touchless is the ultimate peak of airport efficiency.

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Brandon Whichard @brandonwhichard.com · 21/02/2026

The Modern Stack simplifying cloud, AI hype cycles, and how bottoms-up adoption actually plays out. Lots to discuss this week.

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Brandon Whichard @brandonwhichard.com · 13/02/2026

Latest episode is out. We dig into the future of SaaS, OpenAI vs. Anthropic strategy, cloud capex… and debate when (or if) we’ll trust an AI to book our flights.

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Brandon Whichard @brandonwhichard.com · 08/02/2026

A fun and short episode for your weekend listening. Check it out.

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Brandon Whichard @brandonwhichard.com · 30/01/2026

Moltbot is taking over, Apple has new AirTags, and we finally found where the Enterprise AI ROI is hiding. Plenty to dig into this week.

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