Caleb Chan

CEO @TryLance (YC W26) We're Hiring link below! | dropped out @ucberkeley | @google

[Caleb Chan @calebychan]

Future of Hotels Is Run by Lance.

@TryLance now backed by @ycombinator

[Sue @suekhim]

AI is making kids dumber.

It should be making them geniuses.

Introducing Koji, the first AI tutor that gets kids to actually think. 👇

[Aaron Epstein @aaron_epstein]

The biggest hack I’ve seen for founders to close deals faster: just show up.

Get on a plane, fly to their office, meet in person, bond with the whole team.

Instantly replaces weeks of zoom calls.

[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.

[Caleb Chan @calebychan]

One of the most rewarding parts of deploying new AI technology is we have the opportunity to transform entire lives.

For the longest time the world told us that you had to go to a good school, you had to speak English, come from a wealthy background.

AI will be the democratizing force in human history and it’s an honor to help empower people who have been overlooked for far too long.

For the first time ever housekeepers, the people who truly run the hotel are empowered with the intelligence of 10,000 phds at their fingertips.

If this is a mission you believe in come join us :)

https://t.co/yTI2Y1pO43

[Caleb Chan @calebychan]

Mythos worst nightmare

[Caleb Chan @calebychan]

@TryLance Shoutout!!

[Raphael Schaad @raphaelschaad]

MIT student asked a question earlier today that a lot of young founders are quietly wondering about:

"Won’t the frontier labs just do everything?"

Yes it's true that OAI/Ant are shipping at incredible pace, but it's quite easy to avoid their blast radius and build amazing startups:

OpenAI is not going to build a cattle-herding drone, buy an old F-150 and drive from ranch to ranch like the founder of one of the fastest-growing YC W26 startups, Graze Mate.

Anthropic is not going to integrate with dental insurance verification systems (Lance).

Google is not going to navigate NATO procurement (Milliray).

The value is in the last mile, not the model. Sales cycles require humans who understand the customer. And most importantly, the market is expanding, not shrinking: AI isn't cannibalizing the existing 1% software spend — it's unlocking the other 5-6% that was going to humans. That's a much bigger market for startups yet-to-be-founded than the one the labs are playing in.

Now, what DOES seem risky?

A thin UI layer on top of ChatGPT with no domain expertise; a general-purpose chatbot or assistant; or a product that gets obsolete when model capabilities improve.

But — tools for specific industries; "full-stack" AI companies that actually are the service (AI law firm, AI accounting firm, AI uranium exploration company); or generally products where the customer doesn't want a tool but an outcome — are defensible ideas for startups.

[Caleb Chan @calebychan]

Less than 5 😊

[Ryan Petersen @typesfast]

@ycombinator @TryLance Can it check me into the hotel in under 10 minutes?

[Y Combinator @ycombinator]

Congrats to @TryLance on their $5M seed!

Lance builds AI agents that run hotel operations, handling guest communication and executing the work behind the scenes.

Hotels still rely on calls, radios, and manual coordination. Staff miss inbound calls, juggle requests across disconnected systems, and spend hours on repetitive tasks instead of serving guests.

Lance acts like an autonomous operator. Their agents answer calls and messages, create and route work orders, update systems, and coordinate staff in real time. This means faster responses, fewer missed bookings, and a more efficient operation overall.

https://t.co/oo6B5goZKo

[Jibran Hutchins @jibranhutch]

We at @Haladirofficial just raised our seed round, bringing our total amount of funding to $4.3M to build operational superintelligence. Led by @BoxGroup and @SusaVentures, with participation from @seedtosunflower, @Valkyrie_vc, XPRESS Ventures, and various angels, with prior round funding from @ycombinator and @svangel, and our first believer, @Joshuabrowder.

[Caleb Chan @calebychan]

@agustormakh @vercel @aisdk @NotionHQ Fire

[Claude @claudeai]

Computer use is now in Claude Code.

Claude can open your apps, click through your UI, and test what it built, right from the CLI.

Now in research preview on Pro and Max plans.

[Caleb Chan @calebychan]

@MRadhuber @shiprajhahirani @sdianahu @vivianmshen Q1 is crazy

[Caleb Chan @calebychan]

@vivianmshen Goat partner. Thank you!

[Caleb Chan @calebychan]

LeDemo Day

@TryLance

[Caleb Chan @calebychan]

Mr Auramans glasses @jibranhutch

[Jibran Hutchins @jibranhutch]

Great demo day @ycombinator.

[Xinwei He @xinwei_97]

Back to @ycombinator for W26 Alumni Demo Day.

Watching 100+ companies pitch reminded me why I love this community - everyone's building something that didn't exist a year ago.

[Vivian Midha Shen @vivianmshen]

perfect day for an alumni demo day at YC

[Vesting ⚡ @vesting_tv]

He got a Google offer at 19, helped build AgentForce at Salesforce, then quit everything because hotels are still running on DOS systems from the 70s 🏨

"We were like holy shit — hotels haven't even touched the surface of AI yet."

Host - @brycent

@calebychan @GavinBrennen @GatikTriv

@TryLance

[Caleb Chan @calebychan]

We’re Hiring! Check us out in bio :)

[Brycent @brycent]

For the first time ever, a @ycombinator startup, @TryLance, announced their oversubscribed $3.7m seed round on the @vesting_tv show: 🥳

@calebychan, @GavinBrennen, and @GatikTriv reached out and said they wanted to announce the moment prior to demo day.

Lance is building AI agents that run hotel operations and so far they're in 43 hotels, have $2.2m in contracted revenue, and have found product-market fit (in just thee months).

Exceptional team, solving major pain points for hotels.

I am humbled and honored for the opportunity to join them for such an incredible moment.

🔗: https://t.co/abjJCv3Sh3