Todd Dailey

22 years at Apple. AI positioning, executive briefings, tech demos, technical sales enablement. Now independent.

[Todd Dailey @twid]

Here’s an Apple secret:
Success comes from culture, not technology.

Like many at Apple, I worked for many years under John Brandon, our longtime head of sales. He had his “Top Ten Rules for Success” which I carried around and lived by.

It’s easy to spot someone from Brandon’s team by how they collaborate. I tried to be one of them. I mopped the floor (literally at times), I shared everything I knew without gatekeeping, I always assumed the customer knew their business.

I think about AI the same way. Most AI advice right now is for builders. Almost nobody is helping the marketers, sales engineers, and execs who actually have to put AI in front of customers. That’s the gap I work in.

I left Apple last month after 22 years. After some thinking and a lot of conversations, I’m now doing what I did inside Apple, but for other organizations: AI positioning, helping businesses understand AI, and creating Apple-level presentations and content.

[Todd Dailey @twid]

Just out and on my reading stack @trevorpaglen’s “How to see like a machine” and @CaballeroAnaMa’s new book of poetry “Material”

[Todd Dailey @twid]

Prompt

A happy MacBook Pro user sitting in a professional modern office space. They are using the Mac at their desk. Style of a magazine ad pro lifestyle photoshoot for a laptop. Behind them on the wall it says “ACME CORPORATION” with a modern logo. At the side of the desk is a coffee mug that says “Todd is awesome”

[Todd Dailey @twid]

Not too impressed with my first run of @ideogram_ai with my standard test prompt

1 - twin in back, sign makes no sense
2 - best of the four but body is in the desk
3 - legs 😆 - desk makes no sense
4 - desk makes no sense - lamp makes no sense

Doesn’t feel SOTA.

[Todd Dailey @twid]

Grok (dvd slot and weird screen - not good)

[Todd Dailey @twid]

OpenAI

[Todd Dailey @twid]

Gemini (nano banana 2)

[Todd Dailey @twid]

Proto-GIF’s!!!

[NB @Noahbolanowski]

Incredible to think that for nearly 300 years, we have desired & displayed framed animated artworks - brought to fruition via the most cutting edge technology of the day.

Below: Animated Musical Tableau with Clock by A. Tharin & Henri Marc, 1840-50 | Morris Museum Collection.

[Todd Dailey @twid]

@AnthropicAI

[Todd Dailey @twid]

building a family reunion site with @AnthropicAI Claude Code, kept getting things like "The IP reminder isn't relevant so I won't do anything..." - so I asked. Interesting!

[Todd Dailey @twid]

Excited to go to @lennysan’s summit in September!

[Todd Dailey @twid]

@trevin @lennysan Me too! See you there!

[Patrick Hsu @pdhsu]

people aren’t celebrating this pancreatic cancer breakthrough enough. it should be international news

[Todd Dailey @twid]

Agree just picked up a 128GB MacBook Pro and it’s an incredible laptop. The fast memory bandwidth important for on-device AI, plus nano texture and much better brightness for use outside. Claude and Codex Mac clients both spin up Linux containers on Mac, so 8GB won’t work.

Different machines for different purposes! I have a Neo for couch surfing and love it.

[Matt Van Horn @mvanhorn]

Introducing Agent Cookie. 🥷🏻🍪 For anyone running @OpenClaw or @NousResearch's Hermes on a Mac mini: I kept finding my agent logged out of everything, and it sucked. So I fixed it.

"Add this to my Amazon cart." Sorry, logged out again. "Order my usual on Instacart." Nope, not logged in anymore.
The fix: your laptop's cookies, CLI tokens, and API keys sync to your Mac mini. Continuously. Encrypted end-to-end over your Tailscale tailnet. No logging in twice.

🌐 https://t.co/41VezMs9S6

[Todd Dailey @twid]

@mvanhorn @openclaw @NousResearch Ooo this is great - hit this all the time!

[Todd Dailey @twid]

@Interface_art Thank you! The color idea was all Anne’s - I was just the implementer. Great to have an artist bring ideas to the design.

[Todd Dailey @twid]

@ivanfioravanti I will show you the South Bay!

[Todd Dailey @twid]

Smart companies will realize that middle-management is no longer needed at the ratios of the past. One person should be able to manage ten people easily now, while also being a contributor, not just a manager. Too many levels just add friction and slows down decision making.

[Peter H. Diamandis, MD @PeterDiamandis]

Two people with Claude can replicate a Fortune 500 business line in 60–90 days. 80% of enterprise AI projects are failing, but because companies are automating hierarchy rather than technology, they're not replacing it. Salim Ismail calls it the Organizational Singularity... the org chart as we know it is dead.

-- Middle management's coordination role drops ~90%. A company of 800 can run with 80.

-- Cognition Labs went fully AI-native and grew ARR 73x.

-- The biggest moat isn't data, regulation, or brand — it's an intelligence moat.

-- Sheikh Mohammed wants 50% of the Emirati government running on this model.

[Todd Dailey @twid]

Great write up from Ivan with actual set-up notes on 2x M3 Ultra Mac Studios running DeepSeek V4 Flash at 30tps or so using ds4

[Ivan Fioravanti ᯅ @ivanfioravanti]

https://t.co/R1D4h6hnfW

[Todd Dailey @twid]

@sofiagarcia_io I built an AI thing that made a summary. Pretty good I think!

https://t.co/VnWGpJHEgh