Hollie Wegman

Writing about startups, company building, and AI

[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

[Hollie Wegman @dearoperator]

For years, software has been judged by what it can do, not how easily it can be used. If something was technically possible, that was enough. That’s the arrogance of capability. AI is about to expose that.

Read more: https://t.co/yaMeB5THvh

[Hollie Wegman @dearoperator]

We spent a decade making software multiplayer.

AI quietly reset us back to single-player.

It makes you faster alone. It doesn’t yet help teams think in the same system. That gap is going to matter.

Read more:
https://t.co/3fVHAxRG84

[Hollie Wegman @dearoperator]

Craft once implied a craftsman. With AI that’s rapidly changing and founder’s need to adapt.

Read more:
https://t.co/hSa5f6SE5r

[Hollie Wegman @dearoperator]

Agents don’t believe in your brand. They test what works. That changes everything.

Read more: https://t.co/hb0ZkUd9kx

[Hollie Wegman @dearoperator]

@KHashemee Services are going to be crucial in this era. That’s a clever bet!

[Hollie Wegman @dearoperator]

Proficiency with AI tools will matter.

But if you don’t also have 2 of these 3 skills, it won’t be enough to thrive in the AI era:

Systems thinking — designing intelligent workflows
Founder thinking — starting bold new initiatives
Craft thinking — bringing art, taste and judgment

Tool fluency is becoming table stakes.

Read more:
https://t.co/cWsbVzrn6E

[Hollie Wegman @dearoperator]

AI is making us all move faster and in roughly the same direction. True breakthroughs are going to become increasingly rare.

Read more: https://t.co/soe0HP75n2

[Hollie Wegman @dearoperator]

Anthropic’s recent report sparked a lot of discussion about how much knowledge work AI might automate.

Let's push the scenario further

Imagine AI eventually handles something like 80% of the work people in tech do today.

Who gets the jobs tied to the 20% that remain?

Read more:
https://t.co/cWsbVzrn6E

[Hollie Wegman @dearoperator]

@samshank Susan Wojcicki, former CEO of YouTube, famously measured "watch time" and there was a billion hour goal. What was cool about watch time versus something like view counts was it rewarded engagement instead of click bait. One metric can be very powerful!

[Hollie Wegman @dearoperator]

We are entering software’s third era.
Human-led → AI-assisted → Agent-led

In this era well designed governance becomes an unfair advantage for founders.

Read more:
https://t.co/s8ahN4unz3

[Hollie Wegman @dearoperator]

@psomkar1 Will they need developers? They will need brands though.

[Hollie Wegman @dearoperator]

Studied the open roles at Cursor, Harvey, ElevenLabs, LangChain and more.

They’re organizing around agents, deployment-heavy GTM, and AI-foward legal and finance.

AI Startups aren't just building different products they are building different companies.

Read more:
https://t.co/C9ZCTaHHTj