Brandon Whichard

Brandon Whichard

@brandonwhichard.com

Product Marketing and Management, Host of Software Defined Talk

104 followers46 following151 posts

Is AI a single-player game? We get into that this week, along with sovereign cloud, CoreWeave's debt, and what we took away from the Postgres conference.

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This week, @brandonwhichard.com and @cote.io discuss sovereign cloud, Postgres conference takeaways, CoreWeave's debt, and why AI is a single-player game. Plus, whether home automation is worth it. https://www.softwaredefinedtalk.com/595

If your CI still boots a fresh VM for every job and reruns the same steps, you're already behind. Dan Manges breaks down why on this week's show.

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@brandonwhichard.com talks with @rwx.com CEO Dan Manges on @theentaishow.bsky.social about why CI is the bottleneck in the agent era: fast feedback loops, graph-based pipelines over VM jobs, and letting agents run CI before opening a PR. https://www.theenterpriseaishow.com/episodes/19994499

Building a professional-grade app is now within reach of millions of people. Finding demand and building a business are as hard as ever. I get into that with Brian on The Enterprise AI Show, along with CoreWeave's financing and the CIO ROI problem.

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@brandonwhichard.com joins @bgracely.bsky.social on @theentaishow.bsky.social for the month's AI news: CoreWeave's rising borrowing costs, CIOs hunting for ROI, Meta's Muse agent, and whether software fundamentally changed in the last two weeks. https://www.theenterpriseaishow.com/episodes/19980899

Should AI be the one making the yes/no call? We also get into the SaaS apocalypse, Bending Spoons, and Oxide's funding.

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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss AI yes/no deciders, the SaaS apocalypse, Bending Spoons, and Oxide's funding. Plus, why Google Docs still has no dark mode https://www.softwaredefinedtalk.com/594

Data sovereignty keeps getting more important. This week we looked at what it takes to run your own infrastructure without depending on another country's cloud.

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@brandonwhichard.com talks with Dominic Williams of the DFINITY Foundation on @theentaishow.bsky.social about building a cloud nobody owns: sovereign infrastructure for the agent era, with software that's tamper-resistant and always available. https://www.theenterpriseaishow.com/episodes/19945153

Google Docs finally gets Markdown, Cloudflare's new CLI, and the agentic AI abandonment stat everyone's going to misquote. Plus forward deployed engineers.

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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss Google Docs finally getting Markdown, Cloudflare's CF CLI, Gartner's agentic AI abandonment stat, and forward deployed engineers. Plus, Coté forgets his laptop. https://www.softwaredefinedtalk.com/593

Are agents the new kingmakers? I asked Stephen O'Grady on The Enterprise AI Show.

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On @theentaishow.bsky.social, @brandonwhichard.com interviews @redmonk.com's Stephen O'Grady. They discuss his original thesis that developers are The New Kingmakers and what's changing in the world of agents. https://theenterpriseaishow.com/episodes/19921034

Oracle's force majeure notice is worth watching. If other companies follow, AI infrastructure commitments are under stress. We talked it through on The Enterprise AI Show, along with the agent launches and Meta's MongoDB hire.

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@brandonwhichard.com joins @bgracely.bsky.social on @theentaishow.bsky.social to discuss Oracle's force majeure notice, agents getting their own cloud computers, and Meta hiring MongoDB's CEO. https://www.theenterpriseaishow.com/episodes/19904932

Meta's Muse, who's spending $500 million on tokens, and why nobody can measure AI ROI. Plenty to dig into this week.

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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss Meta's Muse, who's spending $500 million on tokens, and why nobody can measure AI ROI. Plus, the case for importing NyQuil by the suitcase. https://www.softwaredefinedtalk.com/592

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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This week, @brandonwhichard.com and @mattray.dev discuss why Sun really failed, the New Kingmakers becoming agents, and AI doom brackets. Plus, the NC State fumble and tech's biggest own goals. https://www.softwaredefinedtalk.com/591

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

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This week, @brandonwhichard.com and @mattray.dev discuss AI doom odds, WordPress's boardroom coup, and Meta's Muse assistant. Plus, a robot vacuum fire scare. https://www.softwaredefinedtalk.com/590

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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This week, @brandonwhichard.com, @mattray.dev and special guest Aaron Delp discuss the VS Code documentary, Ed Zitron's rise to fame, and a 10% AI extinction forecast. Plus, the NFL's Australia travel gamble. https://www.softwaredefinedtalk.com/589

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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@brandonwhichard.com joins @bgracely.bsky.social and Aaron on @theentaishow.bsky.social to ask: is AI a vitamin or a painkiller? Why transformation needs a burning-platform moment, and why personal AI gains aren't scaling org-wide. https://www.theenterpriseaishow.com/episodes/19761188

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss rogue AI agent civilizations, why AI can't fix your tax forms, and Chainguard vs. IBM's Lightwell. Plus, refrigerator magnet marketing. https://www.softwaredefinedtalk.com/588

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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@brandonwhichard.com joins @bgracely.bsky.social and Aaron on @theentaishow.bsky.social to cover NVIDIA's record quarter, its Hugging Face acquisition, Stripe's OpenRouter deal, unsettling OpenAI agent tests, and Salesforce's Claudeforce. https://www.theenterpriseaishow.com/episodes/19740297

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss Stripe's singularity letter, its $8B Open Router buy, and AI job anxiety. Plus, Matt plays “Bot or Not” on another podcast. https://www.softwaredefinedtalk.com/587

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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New episode of @theentaishow.bsky.social: @brandonwhichard.com interviews Rich Ziade, founder of Aboard, on why AI projects fail without real discovery, why "agents" are oversold, and why digital transformation still requires hard conversations. https://www.theenterpriseaishow.com/episodes/19702320

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

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@brandonwhichard.com joins @bgracely.bsky.social and Aaron Delp on @theentaishow.bsky.social to discuss whether GPUs are becoming a financialized "asset class" — or the next bubble. https://www.theenterpriseaishow.com/episodes/19688218

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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This week, @brandonwhichard.com and @cote.io discuss the unsung genius of Apple Pay, AI watermarking, and why digital transformation fails without a crisis. Plus, D&D Beyond's secret character API. https://www.softwaredefinedtalk.com/586

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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@brandonwhichard.com joined Aaron on @theentaishow.bsky.social to dig into owning vs. renting your model weights — and what that tradeoff really means for the enterprise. https://www.theenterpriseaishow.com/episodes/19668501

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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Is open-source AI on the decline? @brandonwhichard.com sits down with Aaron Delp on @theentaishow.bsky.social to talk through the market trends, financial challenges, and what's next for open-source models in the AI landscape. https://www.theenterpriseaishow.com/episodes/19625247

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev 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. https://www.softwaredefinedtalk.com/585

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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Is open source losing the AI model race? @brandonwhichard.com joined Aaron on @theentaishow.bsky.social to argue it might be — the market trends, the money problems, and what's left for OSS in an AI world. www.theenterpriseaishow.com/episodes/196...

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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@brandonwhichard.com joined Aaron Delp on @theentaishow.bsky.social to talk about Ed Zitron, the loudest AI skeptic in tech right now. They work through the bear case against AI: where Zitron lands his punches, and where the argument falls apart. www.theenterpriseaishow.com/episodes/196...

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss the Situational Awareness meltdown, Airtable getting sold, and review the Java documentary. Plus, what you should actually buy at IKEA. https://www.softwaredefinedtalk.com/584

Always good to be on The Enterprise AI Show.

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@brandonwhichard.com joins @bgracely.bsky.social on @theentaishow.bsky.social to break down the biggest AI news stories from July 2026. www.theenterpriseaishow.com/episodes/195...

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

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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss how normal people use AI, Alphabet's Anthropic-fueled earnings, and skills vs. agents. Plus, catching AI-cheating students with a hidden prompt. https://www.softwaredefinedtalk.com/583

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

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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss Bun's move to Rust, OpenAI hunting for revenue, and Stripe's bid for PayPal. Plus, Coté's Dad wisdom. https://www.softwaredefinedtalk.com/582

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.

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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Every project has environment variables. Almost nobody manages them well. This week @brandonwhichard.com talks with Phil Miller and @theozero.bsky.social, who built varlock to fix that — bringing structure and security to the humble .env file. https://www.softwaredefinedtalk.com/580

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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This week, @brandonwhichard.com and @cote.io 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. https://www.softwaredefinedtalk.com/579

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss Fable follow-up, Gartner's AI Governance MQ, and the war for AI talent. Plus, Matt and Brandon review "Disclosure Day." https://www.softwaredefinedtalk.com/578

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev 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. https://www.softwaredefinedtalk.com/577

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

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@brandonwhichard.com talks with OpenObserve's Prabhat Sharma and Shani Shoham: why observability is still broken, how they fixed it, and where AI takes it next. https://www.softwaredefinedtalk.com/576

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss NVIDIA going consumer, Microsoft Build, and the Anthropic/OpenAI IPO race. Plus, does credit card insurance work? https://www.softwaredefinedtalk.com/575

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss the Cloudflare CEO's op-ed, upcoming tech IPOs and GitHub getting breached. Plus, ranking our favorite manifestos. https://www.softwaredefinedtalk.com/574

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

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@brandonwhichard.com joins @bgracely.bsky.social on @theentaishow.bsky.social to break down the biggest AI stories from May 2026. theenterpriseaishow.com/episodes/192...

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

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This week, @brandonwhichard.com and @mattray.dev discuss Google I/O, the OpenAI soap opera, and ChatGPT going full financial advisor. Plus, thoughts on improving the conference hallway track. https://www.softwaredefinedtalk.com/573

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev 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. https://www.softwaredefinedtalk.com/572

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev 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. https://www.softwaredefinedtalk.com/571

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

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@brandonwhichard.com joins @bgracely.bsky.social on @reasoningshow.bsky.social to break down the biggest AI stories from April 2026. https://www.reasoning.show/episodes/19128484

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

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@brandonwhichard.com joins @bgracely.bsky.social on @reasoningshow.bsky.social this week for the 2026 AI Draft — picking winners, losers, and the headlines that'll define the next year in AI. https://www.reasoning.show/episodes/19114514

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss Google's enterprise agent stack, what makes an agent an agent, and AI's biggest critic. Plus, Coté wants better vision. https://www.softwaredefinedtalk.com/570

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss agents taking over at Google Cloud Next, Apple's new CEO, and Cursor getting acquired (sort of). Plus, Coté's e-waste has no exit strategy. https://www.softwaredefinedtalk.com/569

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

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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss Claude's harness, OpenAI's ongoing drama, and whether Backstage is still a thing. Plus, Coté gives up on the green screen. https://www.softwaredefinedtalk.com/568

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.

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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This week, @brandonwhichard.com, @cote.io and @mattray.dev discuss the Claude Code leak, locking down coding agents, and the Axios supply chain attack. Plus, Coté considers breaking up with his Gmail address of 20+ years. https://www.softwaredefinedtalk.com/566

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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@brandonwhichard.com crossed over to @reasoningshow.bsky.social this week — he and @bgracely.bsky.social dug into the biggest AI stories from March. If you're trying to make sense of the last month in AI, start here. https://www.reasoning.show/episodes/18922706

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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This week, @brandonwhichard.com and @mattray.dev discuss big bets gone wrong, OpenAI buying the Python toolchain, and Claude's favorite tools. Plus, how fast should AI agents ship bug fixes? https://www.softwaredefinedtalk.com/565