Hollie Wegman

Writing about startups, company building, and AI

[Hollie Wegman @dearoperator]

@antisxg @MayorofLondon @TfL @ACT Am I the only one that sees a parrot?

[Hollie Wegman @dearoperator]

@paulg Likability matters more than we want to believe. And, for some, being likable is 100x harder than preparing a polished pitch deck.

[Hollie Wegman @dearoperator]

@paulg AI doesn’t only enter organizations within applications it comes in and builds itself. Replit didn’t underestimate this new world.

[Hollie Wegman @dearoperator]

I wonder if this is partly the decline of the news website, not the news. Reuters says social/video networks have now overtaken publishers own sites/apps for news (54% vs 51%). I still consume the news I just increasingly get it from the newsrooms TikTok or trusted influencers who summarize news and link out.

[Hollie Wegman @dearoperator]

We love people who ship. So we learn which ideas ship.

The familiar over the original. The easy-to-explain over the nuanced. The idea that sails through the meeting over the one that might change something.

Make those trades often enough and you build a career in safe mode.

Read more https://t.co/fl8OxYgs8y

[Hollie Wegman @dearoperator]

No signs we’ve wandered into an episode of Black Mirror. No Skynet or HAL. It’s sunny out. We chat with Claude, deploy our agents, take a Waymo.

Meanwhile, the warnings are getting harder to ignore.

Read more https://t.co/r08XT58JhM

[Hollie Wegman @dearoperator]

@santoshdealdocs The vividness of the sounds, so true. At least you could leave the factory, I don’t know about you but I can’t be 2 feet away from my phone!

[Hollie Wegman @dearoperator]

The 9 to 5 didn’t die because we stopped working 9 to5. It died because we started working all the time.

Read more https://t.co/Orl6KYaLUi

[Hollie Wegman @dearoperator]

@hancengiz You’re definitely not alone in feeling this way. It’s what you’re experiencing that inspired the post. A lot of people want to build again. Sounds like you’re enjoying it and in a great path!

[Hollie Wegman @dearoperator]

IC is the new VP

The old path was: IC -> Manager -> Director -> VP

Now a lot of senior leaders are dreaming of being an IC again. Not for less responsibility, for more time to build.

AI has changed the leverage equation. The highest impact career may no longer be managing the largest team. It may be becoming the best builder in the room.

Read more in this weeks Dear Operator
https://t.co/Hl7rpaY62S

[Hollie Wegman @dearoperator]

We say we want people who take risks.

Then we rank talent by resumes that reward people for joining companies after everyone already knows they’re going to win.

Read more:
https://t.co/X9ocsEbF6Y

[Hollie Wegman @dearoperator]

Authorship is the force that keeps people on a project day after day and year after year, paid or unpaid.

It’s a mind so stuck to something it’s compelled to express it. Maybe in wringing, song, art or otherwise.

AI doesn’t touch it. Watermarks don’t matter.

[Hollie Wegman @dearoperator]

AI use ≠ AI slop

We've started treating AI as the dividing line between good and bad writing and I think that's the wrong distinction. AI isn't what makes writing feel empty. What makes writing feel empty is the absence of authorship.

Read more in this weeks Dear Operator
https://t.co/kgbeUHNzuW

[Hollie Wegman @dearoperator]

A meal gets delivered without the driver ever stepping into the kitchen.

Now with AI, a recommendation gets delivered without the worker ever stepping into the problem.

That's cognitive gig work.

Read more: https://t.co/mfAYctZIX4

[Hollie Wegman @dearoperator]

The biggest organizational mistake of the last 20 years was turning “maker work” into an engineering-only identity. AI is about to expose how much of the company actually depends on deep work.

Read more: https://t.co/tmUeOKJOrp

[Hollie Wegman @dearoperator]

AI is breaking taste itself.

Tasteful branding, elegant copy, polished websites, emotionally calibrated marketing. Everything online suddenly looks sophisticated. And strangely, that may be very good news for real builders.

Read more: https://t.co/Ub8mgANFO2

[Hollie Wegman @dearoperator]

Most GTM drift doesn't start with a bad hire. It starts the moment the founder decides they're done with sales.

Read more: https://t.co/hydT1qZkbC

[Hollie Wegman @dearoperator]

We used to struggle to execute.
Now we struggle to understand what we’re executing.

AI Brain Fry has a cost.

Read more: https://t.co/8zw1r4Nvqd

[Hollie Wegman @dearoperator]

RIP OKRs.

Set a target of 100 and you’ll get 100. AI makes the upside unknowable. So why are we still capping it?

Read more: https://t.co/JXEuu5aDzQ

[Hollie Wegman @dearoperator]

https://t.co/es5NWrvHoO