William Craig

Father, Husband, Founder.

Building the future of telecom with @SignalHouseSMS, an AI-first SMS aggregator and voice routing engine.

[William Craig @WillCraigSH]

@aakashgupta That's also Max's yacht.

[William Craig @WillCraigSH]

It's about to get very interesting.

[MTS @MTSlive]

SITUATION DETECTED: Anthropic to release Mythos tomorrow, per Sources.

[William Craig @WillCraigSH]

If you think Ozempic is incredible, just wait until Reta is on the market.

It is going to be the Cadillac of drugs.

[unusual_whales @unusual_whales]

Eli Lilly says next-gen obesity drug curbs sleep apnea, among other benefits, per Reuters

[William Craig @WillCraigSH]

Not necessarily sure 50% equity in AI labs is the way to go here, but I actually am in favor of a version of this.

Basically a government-backed equity raise with pre-set terms depending on valuation, growth, EBITDA, etc. w/ proceeds paying for healthcare, UBI, etc.

[MTS @MTSlive]

SITUATION DETECTED: Senator Bernie Sanders has called for a law granting the federal government a 50% stake in each AI lab to create a public sovereign wealth fund.

[William Craig @WillCraigSH]

Prediction markets reward insider information. That's supposed to be the point.

If you want to them to be a heuristic for the truth, there has to be insider information involved.

Will anything come of this? Not sure. My advice: If you're not a sharp, you're a square.

[unusual_whales @unusual_whales]

A Google software engineer allegedly earned $1.2 million by illegally trading contracts on Polymarket that allowed people to bet on who would be revealed as the most searched people of 2025, per WSJ

[William Craig @WillCraigSH]

This was always going to be the question: Do revenues justify the spend?

We're beginning to see more and more evidence that the top-end of the market (Fortune 500, etc.) is not seeing the same efficiency gains startups are seeing.

There's many reasons for this:

1. Disparate data systems
2. Vertical org structures preventing cohesion
3. Perverse incentives (tokenmaxxing)

Will we see revenue flow from token-spend? Yes. We most-certainly will.

When that shows up in the cycle, and where, will determine whether public market CEOs continue to be AI-pilled.

[Polymarket @Polymarket]

JUST IN: Uber’s COO says heavy AI spending is getting harder to justify, as higher token usage fails to show a clear payoff in consumer features.

[William Craig @WillCraigSH]

If you're considering an MBA, I strongly urge you to work for 2 years at an early-stage startup instead.

Best education you can get.

[unusual_whales @unusual_whales]

Business schools are offering up to 50% off MBAs, per Entrepreneur.

[William Craig @WillCraigSH]

This is true, no doubt about it—but as a CEO you should also just be listening to feedback from your team also.

Go to your best engineers, best PMs, best designers, best GTM folks, etc., and ask them to supercharge their output with AI: "For each multiple increase in output without a decrease in quality, I will pay you."

If it's less than you thought, have a conversation about why. Help them help you understand the complexities better so you can help them optimize.

The best orgs have founders who intimately know what's going on at the ground level; that should be from testing the tools yourself and getting extremely direct, unfiltered feedback.

[Aaron Levie @levie]

CEOs are uniquely prone to AI psychosis because they’re sufficiently distant from the last mile of work that still has to happen to generate most value with AI.

So when they play with AI, they see the happy path results, often not considering the next 10 or 20 things that have to happen to get sustainable results from agents.

“Look I made this awesome product prototype”. Yes but you didn’t have to review the code before it went into production and fix a bunch of issues.

“Look I generated a contract”. Yes but you didn’t verify all the terms before it goes out to the counterparty and didn’t have to wire up all the past contracts to work with.

The best thing you can do as a CEO is to use AI a *ton* to figure out the real implications of agents in the enterprise, and come out the other side with an appreciation for both the upside and the real work that goes into them.

[William Craig @WillCraigSH]

In a world where more and more people are terminally online—both personally and professionally—meeting face to face makes so much more of a difference.

It's really easy to get on a zoom call.

Your customers have 8-10 per day. They aren't memorable.

A lunch meeting? That is.

[Tom Blomfield @t_blom]

A founder just apologized for dialing in to office hours from a car. It’s the sixth time he’s done this.

He spends close to 100% of his time meeting customers in unglamorous places a long way from San Francisco.

I wish more founders did this.

[William Craig @WillCraigSH]

To add here, you don't need to start a VC-backed rocket-ship startup.

You can build a business that gives you a nice, comfortable life (no 18-hour days) so much easier today than could have been done in the past.

It's all possible, you just have to take the first step.

[@jason @Jason]

For hundreds of years, business owners have replaced humans with machines that don't complain or get tired.

It's now happening at an accelerated rate.

There is only one solution: learn the tools.

If you can't find a job applying to them, start a company.

We're going to see 100 times as many small- to mid-sized companies in the next decade or two. https://t.co/8rEIrf34o4

[William Craig @WillCraigSH]

If you say: "That's not X, it's Y" anywhere within a post of any kind, I immediately see it as AI slop and no longer care about what you're saying.

[William Craig @WillCraigSH]

The new Sheets logo is horrendous

[William Craig @WillCraigSH]

This can legitimately be really hard for people to understand. It seems callous, unnecessary, and premature: it's not.

As a CEO, your job is to ensure the organization exists long after you've retired.

22% of the workforce lost their jobs today, and that really sucks. But if Zeb didn't act, 100% could lose their job by the end of next year.

That's genuinely how quickly things are moving right now.

When these decisions are made, they aren't made lightly, nor in a vacuum. It's not to get your name in the news or be praised by your VCs/board.

It's to ensure longevity through this, and other future cycles.

To do is to be judged, to not is to die.

[William Craig @WillCraigSH]

I truly feel for everyone affected by this, but Zeb is spot-on in his analysis.

I've been trying to find the right categories to convey my own findings within our org and he does so very well.

Product and design are one and the same now; tasteful PMs are invaluable.

Great engineers are 100x what they were before, and poor engineering derails this (as does PMs shipping code).

System owners own the systems—they architect and scaffold the frameworks within which the Engineers and PMs operate in.

Front-liners have to be engaging with customers daily, being increasingly human in a non-human environment.

Well done.

[Zeb Evans @DJ_CURFEW]

Today we reduced headcount by 22%. The business is the strongest it's ever been. So I think it's important to be direct about what I'm seeing and why.

First, I made this decision and I own it. I did it because the way to operate at the highest level of productivity is changing, and to win the future, ClickUp needs to change with it.

Second, this wasn't about cutting costs. Most savings from this change will flow directly back into the people who stay. We'll be introducing million-dollar salary bands. If you create outsized impact using AI, you'll be paid outside of traditional bands.

Most importantly, I have the deepest gratitude for those affected. We're doing this from a position of strength specifically so we can take care of people properly. Everyone affected receives a package aimed at honoring their contributions and easing the transition.

I only see two options: wait for this to play out gradually in the market or be honest about what I'm seeing and act proactively.

THE 100X ORGANIZATION
The primary change is that we're restructuring around what I call 100x org. The goal is 100x output. The roles required to build at the highest level are fundamentally different than they were a year ago.

Incremental improvements to existing systems won't get us there. We need new ones. That means creating enough disruption to rebuild rather than iterate on what's already broken.

The common narrative is that AI makes everyone more productive. It doesn't. Many of the workflows of today, if left unchanged, create bottlenecks in AI systems.

These roles will evolve. But waiting for that to happen naturally means falling behind now.

The 100x org is actually heavily dependent on people - infinitely more than today. This is only possible with 10x people that have embraced and adopted new ways of working.

THE BUILDERS, AGENT MANAGERS, AND FRONT-LINERS

— THE BUILDERS: 10X ENGINEERS
I don't think most companies have internalized what's actually happening with AI in engineering. The common narrative is that AI makes all engineers more productive. That may be true in isolation, but at an organization level - that is the farthest thing from reality.

Here's what we've validated recently at ClickUp: the great engineers, the ones who can orchestrate, architect, and review, are becoming 100x engineers. They're not writing code. They're directing agents that write code. The skill is judgment.

AI makes the best engineers wildly more productive, and everyone else using AI slows these engineers down.
Think about it - the bottlenecks are (1) orchestration - telling AI what to do, and (2) reviewing - what AI did. Everything is leapfrogged and no longer needed.
So who do you want orchestrating and reviewing code?

And how do you want your best engineers to spend their time?

If your best engineers are spending time reviewing other people's code, then this is inherently an inefficient bottleneck. These engineers can review their agent's code much faster than reviewing human code.

The new world is about enabling your 10x engineers to become 100x.

The wrong strategy is to push every engineer to use infinite tokens. Companies doing this are celebrating 500% more pull requests. But customer outcomes don't match the volume of code being generated.

I call this the great reckoning of AI coding, and every company will face this soon if not already.

More code is just another bottleneck to the best engineers, and ultimately to your company's impact as well.

— THE BUILDERS: 10X PRODUCT MANAGERS
Product management and design roles are merging.

Designers that have customer focus, become more like product managers.

And product managers that have intuition for UX become more like designers.

The bottleneck of user research is gone. It takes us just one mention of an agent to kickoff research and analyze results.

The bottleneck of product <> design iteration is also gone. The product builder iterates on their own, along with agents and skills that ensure alignment with quality and strategy.

Also controversial today - I believe that the wrong strategy is to have your PMs shipping code - that just introduces another bottleneck that the best engineers will waste their time on.

To be clear, PMs should be coding but they should do this in a playground to iterate, validate, and scope. That code should not go to production.

Everything outside of managing systems, orchestrating AI, and reviewing output becomes a bottleneck.
That's why the other roles that are critical along with these are the systems managers (to reduce bottlenecks) along with a bottleneck you can't replace - customer meeting time.

— THE SYSTEM MANAGERS
Ironically, the people that automate their jobs with AI will always have a job. They become owners of the AI systems - agent managers. We have many examples of these people at ClickUp.

The underlying systems in which we operate are absolutely critical to get right. I think most companies are delusional to think they can iterate on existing systems and compete in this new world.

You must create enough disruption so that old systems are deprecated entirely. If there's any definition for 'AI native' that's what it is.

— THE FRONT-LINERS
In a world that will become saturated with AI communication, the human touch will matter more than anything to customers.

This is a bottleneck that you shouldn't replace - even when agents are high enough quality to do video meetings.

One-on-one meeting time with customers is something that shouldn't be automated. The systems around the meetings should be - so that front-liners spend nearly 100% of their time with customers.

REWARDING 100X IMPACT
In a world where companies are able to do so much more with less, where does that excess money go?
In our case, much of the savings in this new operating model will flow directly back to those that enabled it.

We must reward people that create productivity accordingly. This aligns incentives on both sides. Plus, in a world where your best people create 100x impact, you can't afford to lose them.

You should aim to retain these employees for decades. The context they have and their ability to efficiently orchestrate and review will be nearly impossible to replace.

Compensation bands of today should be thrown out the door. We're introducing $1 million cash/year salary bands with a path available to nearly everyone in the company if they produce 100x impact by creating or managing AI systems.

THE FUTURE
Nearly every company will make changes like these. The ones that do it proactively will define what comes next.

The future is not fewer people. It's different work, new roles, and better rewards for those who embrace it. We're already seeing entirely new roles emerge, like Agent Managers, that didn't exist a year ago.

ClickUp is positioning to lead this shift, not just internally, but for our customers too. I've never been more certain about where we're headed.

[William Craig @WillCraigSH]

As it should. What you've done is a predictive heuristic of future achievement.

I do not care what school you went to, the private experiences your family's wealth afforded you, or your past job title.

I care about your body of work, attitude, and ability to grow.

A meritocratic analysis of you vs. the other candidates I'm reviewing.

Some of the best people I've ever hired have been those who weren't afforded the same opportunities as their peers due to a low-SES background.

They had grit, determination, and made things happen.

Something those who were silver-spoon-fed simply don't understand; they 'wait until things come to them.'

Resumes are an elitist framework; portfolios and work-product (whether it was deployed or generated purely for the interview) are achievable by all.

Show me what you can build and understand how it will help me. You do that? You're hired.

[unusual_whales @unusual_whales]

The resume is dying, as hiring shifts towards skills, portfolios and real work proof, per Forbes.

[William Craig @WillCraigSH]

If you're using a single model to drive product output (whatever that model is), you're doing it wrong—and you'll be left behind.

We're making models compete with each other and check their competitors' work.

Tokenmaxxing? Maybe. Outputmaxxing? Yes.

[William Craig @WillCraigSH]

@nikitabier AR-15, easily.

[William Craig @WillCraigSH]

Yes, AI outputs will always be average because of inherent power law.

1% of things hit, and when you’re trained on the 100%, a human with taste will need to be in the loop.

That said, AI is getting better at identifying what is good about the 1% and replicating it—finding patterns and through lines in what you’re doing as well.

I agree with the premise but the framing is wrong:

The most here is brand. Anyone can create a GTA. But it’s not GTA. There’s only one GTA, and the ownership of mindshare is what sells the game on day 1.

The experience is the long tail value capture, but make no mistake: you’re buying the brand.

[Mario Nawfal @MarioNawfal]

The CEO of Take-Two, the company behind GTA, just said something the entire AI industry doesn't want to hear.

And he said it without being anti-AI.

Strauss Zelnick's argument is precise. AI is built on datasets. Datasets are backward-looking. Creativity is forward-looking. A model trained on everything that already exists cannot, by definition, produce something genuinely unexpected. And all hits, by their very nature, are unexpected.

Asset creation and hit creation are not the same thing. AI is getting very good at the first one. The second one is what actually makes money, builds franchises, and changes culture. Nobody has shown AI can do that yet.

The derivative property problem is real. You can clone GTA with existing technology. You could do it before AI. It would take 3 years and look identical. It still wouldn't sell. Because it isn't GTA. It's a clone of GTA.

And consumers, despite what the industry occasionally pretends, can feel the difference between something genuinely new and something assembled from the residue of things that already worked.

Thousands of mobile games ship every year. 0 to 5 hits get made. The same studios make them every time. The technology to make more games has been commoditized for years. It didn't democratize hit creation. It just flooded the market with more forgettable product.

The Silicon Valley thesis that AI unlocks game creation for everyone is true in the same way that cheap cameras unlocked filmmaking for everyone. They did. And the same 5 studios still make the movies everyone watches.

What Zelnick is saying, without quite saying it, is that the thing AI cannot replicate is taste. The instinct for what hasn't been done yet. The cultural antenna that detects the gap in the market before the data can see it.

Data tells you what people wanted. Hits tell people what they want next.

Those are different jobs.

[William Craig @WillCraigSH]

Yes, the talent density in SF is higher than elsewhere.

Yes, it is generally easier to build a business in-person.

Here's the thing though: when you build a business in SF, you are marrying yourself to an endless cycle of raising capital and diluting equity.

You have to raise to hire good people; you must pay them salaries that founders elsewhere are more than happy making (while giving them equity).

Your building costs are 5x higher than elsewhere.

You have to exit as a unicorn to have an exit you can retire on. And that's if you're lucky. Many founders exit multi-$B businesses with 1-5%. Some at 0%.

Contrast that with Austin, Miami, (or in my case, Columbus).

You hire incredible people who live here and others who don't.

You meet in person as often as you can, pay people well, bootstrap the business (or take very little funding), and create a compelling, fast-growing product that doesn't require you to jump into a blender every day.

I get the allure of SF. It's fun to be 'where everything happens.' But you can also make something happen anywhere.

And SF is only a plane ride away. There's lots of hotels. You don't need to live there to find success.

[William Craig @WillCraigSH]

Move. You can start a unicorn literally anywhere, at any age.

It's totally fine to be comfortable with your life at any level of success. That is, in many ways, the dream.

But if you aren't, do something about it.

[Deedy @deedydas]

The vibes in SF feel pretty frenetic right now. The divide in outcomes is the worst I've ever seen.

Over the last 5yrs, a group of ~10k people - employees at Anthropic, OpenAI, xAI, Nvidia, Meta TBD, founders - have hit retirement wealth of well above $20M (back of the envelope AI estimation).

Everyone outside that group feels like they can work their well-paying (but <$500k) job for their whole life and never get there.

Worse yet, layoffs are in full swing. Many software engineers feel like their life's skill is no longer useful. The day to day role of most jobs has changed overnight with AI.

As a result,
1. The corporate ladder looks like the wrong building to climb.
Everyone's trying to align with a new set of career "paths": should I be a founder? Is it too late to join Anthropic / OpenAI? should I get into AI? what company stock will 10x next? People are demanding higher salaries and switching jobs more and more.

2. There’s a deep malaise about work (and its future).
Why even work at all for “peanuts”? Will my job even exist in a few years? Many feel helpless. You hear the “permanent underclass” conversation a lot, esp from young people. It's hard to focus on doing good work when you think "man, if I joined Anthropic 2yrs ago, I could retire"

3. The mid to late middle managers feel paralyzed.
Many have families and don't feel like they have the energy or network to just "start a company". They don't particularly have any AI skills. They see the writing on the wall: middle management is being hollowed out in many companies.

4. The rich aren’t particularly happy either.
No one is shedding tears for them (and rightfully so). But those who have "made it" experience a profound lack of purpose too. Some have gone from <$150k to >$50M in a few years with no ramp. It flips your life plans upside down. For some, comparison is the thief of joy. For some, they escape to NYC to "live life". For others still, they start companies "just cuz", often to win status points. They never imagined that by age 30, they'd be set. I once asked a post-economic founder friend why they didn't just sell the co and they said "and do what? right now, everyone wants to talk to me. if i sell, I will only have money."

I understand that many reading this scoff at the champagne problems of the valley. Society is warped in this tech bubble. What is often well-off anywhere else in the world is bang average here.

Unlike many other places, tenure, intelligence and hard work can be loosely correlated with outcomes in the Bay. Living through a societally transformative gold rush in that environment can be paralyzing. "Am I in the right place? Should I move? Is there time still left? Am I gonna make it?" It psychologically torments many who have moved here in search of "success".

Ironically, a frequent side effect of this torment is to spin up the very products making everyone rich in hopes that you too can vibecode your path to economic enlightenment.