Bob Fine #IVRHA

Engineer, Environmentalist, IT Architect, Publisher: [email protected]

[Bob Fine #IVRHA @bobfine]

https://t.co/BL3U3eapLY

I had a wonderful time this morning talking with director/producer/host Sean King O'Grady and psychiatrist Dr. Joel Gold from @MountSinaiNYC .

We discussed the topic of #AI and the detrimental #health impacts it is having on a subset of the population. It coincides with the debut today of their series: Suspicious Minds: AI and #Psychosis.

You can now watch the first two episodes of the 8-part series. URLs are in the podcast notes with links to YouTube, Apple, Spotify and iHeart. #letswondermind

cc @letswondermind @selenagomez @rarebeauty

[Bob Fine #IVRHA @bobfine]

@sama Sam, I'm building https://t.co/sVGjADD9U0 and believe using VR for collecting spatial training data for humanoid robotics training is a significant need and opportunity. We'd love to work with you to ensure we're building for your needs. - [email protected]

[Bob Fine #IVRHA @bobfine]

@Teamly Can I use my own Claude key?

[Bob Fine #IVRHA @bobfine]

@downingARK Great read!

[Frank Downing @downingARK]

https://t.co/najMqP3mxN

[Bob Fine #IVRHA @bobfine]

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[Bob Fine #IVRHA @bobfine]

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[Bob Fine #IVRHA @bobfine]

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[Elon Musk @elonmusk]

Cybercab driving itself out of the GigaTexas factory

[Bob Fine #IVRHA @bobfine]

@StephNass Playbook

[Bob Fine #IVRHA @bobfine]

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[William Shatner @WilliamShatner]

The needs of the many can be overrated. 😑😏

[Bob Fine #IVRHA @bobfine]

@gregisenberg Great read!

[Ryan Cohen @ryancohen]

Responsibilities include finding out where the money is going…

[Bob Fine #IVRHA @bobfine]

Great read!

[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.

[Bob Fine #IVRHA @bobfine]

@StephNass Open deck

[Ethan Brooks @alt_w_v_g]

You used to sell stuff on eBay.

Maybe an old camera. Maybe Beanie Babies. Maybe a coat that didn't fit.

You paid a small fee. The buyer got the thing. Everyone went home.

That eBay is gone.

The website looks the same. The logo is the same. The 135 million buyers are still there.

But the company isn't really a marketplace anymore.

It is an advertising business with a marketplace attached for distribution.

Last year, sellers paid eBay $2 billion just to make sure their own listings showed up.

Read that again.

The board calls this growth.

A Canadian who runs a video game store called it something else.

Here is what actually happened.

In 2020 the board hired a new CEO. His name is Jamie Iannone. He arrived with a strategy called focused categories.

In plain English, that means leaning into the stuff people pay extra for. Sneakers. Watches. Trading cards. Auto parts.

The everyday seller, the person with the camera and the coat, was no longer the customer.

The customer was now the seller who would pay to be seen.

In 2025 eBay did $80 billion in transactions. They kept $11 billion of that as revenue. Of that $11 billion, $2 billion came from advertising.

Sellers paid them $2 billion to promote listings on a website those sellers already pay fees to use.

That is the growth story.

In the same year, the number of enthusiast buyers, eBay's own term for their best customers, was 16 million.

It was also 16 million the year before.

And the year before that.

And the year before that.

Four years. Zero growth. They mention this on every earnings call without mentioning it.

So what does a company do when growth stops?

It buys back its own stock.

In 2025, eBay returned over $3 billion to shareholders. Most of that was buybacks. In February the board authorized another $2 billion on top.

Buybacks shrink the share count. Earnings per share goes up even when earnings stay flat. The stock price follows.

The stock was $68 a year ago. It is $108 today.

The company did not improve. The denominator got smaller.

Then a man from Canada noticed.

His name is Ryan Cohen. He runs GameStop. He started his career selling pet food online and sold it to PetSmart for $3.35 billion.

He looked at eBay. 135 million buyers. $80 billion in transactions. Real margins. Real cash flow. A board harvesting the business instead of running it.

He bought 5% of the company through derivatives and stock.

Then on May 4, he offered to buy the rest. $125 per share. $56 billion total.

On May 12, the eBay board rejected the bid. They called it not credible.

The math is credible.

What the board means by not credible is we would have to explain why we sold.

Then Cohen went on Piers Morgan.

He said eBay is run by a bunch of losers with perverse financial incentives.

He pointed out that eBay's CEO has been paid $144 million over six years.

He pointed out that he personally takes no salary and has put $128 million of his own money into the company he runs.

You do not have to like Ryan Cohen to notice he is making a point that is hard to argue with.

eBay used to be a place where regular people sold things to other regular people.

Now it is a $48 billion company whose largest growth driver is charging its own sellers to advertise to a buyer base that stopped growing four years ago, while spending billions a year buying its own stock to make the chart go up.

The board calls this strategy.

A video game CEO from Canada called it what it is.

The market is now waiting to see who else agrees.

Plz fix. Thx.

Sent from my iPhone

[Paul Branham @BoilerPaulie]

Allow me to translate this letter from eBay for those who don’t speak legalese:

Ryan,

We got your unsolicited offer to buy eBay for $125/share (half cash, half stock) supported by your 5% economic interest in eBay.

Our board, backed by the usual crew of bankers and lawyers who get paid either way, “thoroughly reviewed” it.

We’re rejecting it. Not because the math doesn’t work. Not because the highly confident letter from TD Securities for up to $20B on top of your $9B+ cash pile is fake. None of that.

We’re rejecting it because your entire approach to running a company is an existential threat to how we like to operate here.

Here are the reasons we feel this way, and the things we considered before paying consultants to write this:

1) We’d rather keep milking eBay as a “standalone” cash cow than let you turn it into something bigger and better.

2) Sure, you’ve got real financing lined up and you “know people” with deep pockets, but we’re going to call it “uncertain” anyway so we don’t have to engage.

3) Your plan would actually force real long-term growth and profitability changes we’d rather not be held accountable for.

4) The debt we pretended you can’t even obtain, the operational integration and focus on seller satisfaction, and most importantly, putting someone like you in charge of the combined entity all sound like a nightmare for our current leadership structure because all of us would have zero job security.

5) The valuation math only looks bad if you ignore the 46% premium you’re offering our shareholders and the upside from fixing eBay the way you fixed GameStop, which we are choosing to do and hoping nobody notices.

6) And I hope we buried the lede far enough here: Your governance and executive incentives are completely incompatible with ours. You and your board take zero cash, no salary, no bonuses, no golden parachutes. You buy shares with your own money and only get paid if shareholders win. We, on the other hand, like our nice, reliable annual payouts regardless of whether the stock is flat or the company is just coasting. We’re not about to hand over our golden goose to a guy who eats only what he kills.

Look, eBay is “strong” and “resilient” in the way every entrenched public company says it is while handing out eight-figure checks and perks to the C-suite. We’ve done the usual incremental stuff: tweaked the marketplace a bit, returned some capital, and we’d like to keep doing that without any cowboy from GameStop coming in and demanding actual skin-in-the-game accountability. Can you just leave us alone?

Our team remains focused on protecting the current regime and delivering “value”… mostly to ourselves and our consultants.

Thanks, but no thanks,

Paul S. Pressler
Chairman of the Board, eBay
(And proud beneficiary of the status quo)

[Bob Fine #IVRHA @bobfine]

@DarrelFrater DM

[bad robot ventures @foxenflask]

In light of $EBAY rejecting the $GME offer this morning against their fiduciary responsibilities, let's take a look at Paul S. Pressler, the board Chair, who is a shining example of what failing upwards looks like in corporate America.

He has been a director since 2015. Chairs the Corporate Governance & Nominating Committee. Has been Chairman of the Board since 2020.

He was present throughout the 2019 stalking crimes, and now sits as Chairman of the full board. In 2019, he chaired the Compensation Committee, making him central to one of the most controversial decisions in the company's history: a board meeting was convened specifically to consider whether to activate the clawback provision on Devin Wenig's exit package, and the board voted not to proceed. That package was worth approximately $57 million. During a September 2024 deposition in the civil litigation, eBay's Director Ethics Counsel testified under oath that Wenig's departure was a firing, not a resignation, and that it was directly related to the stalking scandal. Despite this, the board publicly framed the exit as a mutual decision for months, a characterization that governance critics argue constitutes a material misrepresentation to investors.

Pressler's committee also oversaw a quiet exit for former SVP Wendy Jones, who was interviewed by eBay's internal investigators on August 30 and September 6, 2019 in connection with the criminal conduct and was nonetheless allowed to remain employed through December 2020. Jones ultimately received compensation packages totaling over $11 million upon her eventual departure. Pressler became Chairman in May 2020, taking the seat from outgoing Chairman Thomas Tierney immediately after those decisions were made.

The board waited until February 26, 2026 to reform its committee charters governing risk, audit, governance, technology, and compensation. That restructuring happened one day after the Steiners' civil lawsuit settled with undisclosed terms. eBay had not restructured governance at any point after the crimes became public in 2020, after entering a federal deferred prosecution agreement admitting to six felony offenses in January 2024, or at any time while the civil trial was pending. Critics at the time noted that reforming governance while litigation was active could have made those drafts discoverable and usable as evidence by the plaintiffs' attorneys. Pressler, as Chairman, would have been the chief architect of that timing decision.

Currently, Pressler chairs the Corporate Governance and Nominating Committee, the same committee that oversees Aaron Johnson, eBay's Chief Ethics Officer. Johnson was copied on the August 2019 "Whatever. It. Takes." email from then-Communications Chief Steve Wymer before the crimes occurred. His promotion to lead company ethics, under Pressler's oversight, has drawn sustained criticism from governance observers.

Before joining eBay's board, Pressler served as President and CEO of Gap Inc. from 2002 to 2007. Former employees interviewed by BusinessWeek characterized his tenure as "total system failure." Gap recorded its third consecutive dismal holiday shopping season under his leadership, and the board moved to remove him in January 2007 after months of investor pressure and public calls for his ouster from Wall Street. Founder Don Fisher had publicly defended Pressler in the months before the termination, but the defense did not hold. The board's post-departure statement that it needed someone with "deep retail expertise" was widely read as a direct indictment of Pressler's qualifications for the role. His exit triggered immediate speculation about a sale of the company. He collected $14.5 million in severance.

Pressler served as Chairman of David's Bridal from 2012 to approximately 2018, during the period when the company was owned by private equity. By the time of his departure, David's Bridal carried approximately $760 million in debt. The company filed for Chapter 11 bankruptcy in November 2018 to restructure over $400 million of that obligation. It subsequently filed for bankruptcy a second time in April 2023, this time laying off more than 9,200 employees with no funds expected to be available to unsecured creditors. The structural financial condition of the company at the time of its first bankruptcy was built during Pressler's chairmanship.

As an eBay shareholder myself, I am calling for Paul Pressler to resign immediately. No golden parachute either.