Simon Moore

Focused on the intersection of tech and investing.

[Rohan Paul @rohanpaul_ai]

Powerful new Harvard Business Review study.

"AI does not reduce work. It intensifies it. "

A 8-month field study at a US tech company with about 200 employees found that AI use did not shrink work, it intensified it, and made employees busier.

Task expansion happened because AI filled in gaps in knowledge, so people started doing work that used to belong to other roles or would have been outsourced or deferred.

That shift created extra coordination and review work for specialists, including fixing AI-assisted drafts and coaching colleagues whose work was only partly correct or complete.

Boundaries blurred because starting became as easy as writing a prompt, so work slipped into lunch, meetings, and the minutes right before stepping away.

Multitasking rose because people ran multiple AI threads at once and kept checking outputs, which increased attention switching and mental load.

Over time, this faster rhythm raised expectations for speed through what became visible and normal, even without explicit pressure from managers.

[Nicolas Bustamante @nicbstme]

https://t.co/v7sot4WCI2

[David Marcus @davidmarcus]

A few thoughts about PayPal, nearly 12 years after I left.

I woke up this morning to dozens of messages from former PayPal colleagues. It pushed me to finally speak up.

I never spoke publicly about the company after I left. Part of that was loyalty to John Donahoe, who gave me an unlikely opportunity, handing the reins of PayPal to a startup guy who, on paper, had no business running a then 15,000-person organization. But part of it was something else: I had left. I chose not to stay and fight for the changes I believed in. Speaking from the sidelines felt like armchair commentary. Easy opinions without the burden of execution. So I stayed quiet.

But twelve years of silence is long enough. And today's news makes it clear the pattern I've watched unfold isn't self-correcting.

I left PayPal in 2014 because I was deeply frustrated. We had executed a silent turnaround of a company that had lost its soul. We brought back engineering talent, shipped good products quickly, and acquired Braintree and Venmo. The company was on a tear. So much so that Carl Icahn felt compelled to accumulate a position in eBay and push for a PayPal spinoff. At the time, eBay decided to fight Icahn.

It was a difficult period for me, caught between what I felt was right for PayPal and my loyalty to the eBay team.

This is when Mark Zuckerberg approached me to join Facebook. The combination of his conviction that messaging would become foundational, the appeal of going back to building products at scale, and my growing exhaustion with the internal politics at PayPal and eBay eventually convinced me to leave and join one of the best teams in the world, one I had admired for a long time.

In the summer of 2014, I met John in a café in Portola Valley and told him I had decided to leave. During that conversation, he told me that Icahn had effectively won the fight, that PayPal was going to become an independent company, and he tried to convince me to stay on as CEO, but I had already said yes to Mark, and my word is my bond. There was no turning back.

After my departure, the board scrambled to find a replacement, and it took a few months for them to land on Dan Schulman. The leadership style shifted from product-led to financially-led. Over time, product conviction gave way to financial optimization.

Much of the momentum we had created still persisted and carried the company forward, mainly driven by Bill Ready, who came over in the Braintree acquisition and rose to COO. Under his leadership, Venmo grew exponentially, and total payment volume (TPV) accelerated quickly. But the shift under Schulman became more pronounced after Bill's departure at the end of 2019. With him went the product conviction that had defined the post-spinoff momentum. Then, for a period, COVID-fueled online shopping hid a lot of the company's new weaknesses.

During that period, the company made a fundamental miscalculation: it optimized for payment volume instead of margin and differentiation. It leaned into unbranded checkout, where PayPal had the least leverage, instead of branded checkout, where the margin, data, and customer relationship actually lived.

Visa masterfully structured a deal that effectively ended PayPal's ability to steer customers toward bank-funded transactions, which had been a core driver of PayPal's economics. Not long after, PayPal lost a significant portion of eBay's volume. Over time, it saw its share of checkout among its most profitable customers steadily erode as Apple Pay and others continued to execute well.

The same pattern repeated itself across lending, buy-now-pay-later (BNPL), and new rails.

On lending, PayPal missed the opportunity to turn it into a platform weapon. Products like Working Capital were conservative, short-duration, and optimized for loss minimization. Lending never became programmable, never became identity-driven, and never became a reason for merchants or consumers to choose PayPal over something else.

The missed opportunity in BNPL was even more striking. Klarna, Affirm, and Afterpay didn't just offer installment payments, they built consumer finance brands, persistent credit identities, and new shopping behaviors. PayPal saw the BNPL turn, entered the market, and had every advantage: distribution, trust, and merchant relationships. But BNPL was treated as a defensive checkout feature rather than an offensive category. There was no attempt to turn it into a core consumer relationship, no super-app behavior, and no meaningful differentiation for merchants. Others built platforms, PayPal added a feature.

The failure to lean into building and owning new rails followed the same logic. After the spinoff, PayPal had a once-in-a-generation opportunity to build a global, at scale payment network. Instead, the company focused on building on top of existing networks and third-party rails.

More recently, that mindset carried over to PYUSD. Technically, the product was sound. Strategically, it launched without a compelling transactional reason to exist. PYUSD had distribution, but no organic demand. It was not embedded deeply enough into flows to become a true settlement layer, a cross-border merchant rail, or a programmable money primitive. It sat adjacent to the product instead of inside the core of it.

Acquisitions during this period followed a similar pattern. Honey was not a strategic acquisition for PayPal. It added activity, but not leverage. It lived outside the transaction, monetized affiliate economics rather than payment economics, and never meaningfully strengthened PayPal's control of the customer or the checkout moment. Xoom solved a real problem in remittances, but it never compounded PayPal's advantage. It scaled volume without changing the underlying rails, identity graph, or settlement model, and as importantly, it didn’t cater to a high-value, high-margin customer archetype.

None of these were bad companies. They were just a wrong fit for PayPal and became unnecessary distractions.

The board eventually recognized the problem. In 2023, they brought in Alex Chriss, an Intuit veteran with a strong product background, explicitly to restore product conviction. It was the right instinct.

But Alex came from software, not payments. He understood SMB product development. He didn't have the muscle memory for transaction economics, network effects, or settlement infrastructure.

In hindsight, he also made an error: clearing out much of the leadership team that understood payments deeply. Executives with years of institutional knowledge departed within his first year.

This morning, Alex was removed as CEO. Branded checkout grew 1% last quarter. The board tapped another operator, Enrique Lores, the former HP CEO who's been on the PayPal board for five years.

I don’t know Enrique. And he might be a great leader, but on paper at least, he’s a hardware executive. For a payments company.

The common thread through all of this is incentive design. Once PayPal became independent, short/medium-term predictability beat long-term vision and ambition. Stock performance mattered more than platform risk and network opportunity. Financial optimization replaced product conviction.

I'm not claiming I would have made every call differently. Running a public company at scale involves tradeoffs I didn't have to make after I left. But the pattern, choosing predictability over platform risk, again and again, was a choice, not an inevitability.

Over time, the company that had every advantage and could’ve become the most consequential and relevant payments company of our time, lost its mojo, its product edge, and its ability to compete in a market that’s being rewired and reinvented in front of our eyes.

That's the part that's hardest to watch for a company I care so deeply about.

[Kevin Mak @KevinLMak]

https://t.co/hZaWCNlDjL

[Alexey Strygin @strygah]

I tracked every billionaire who died in the last decade.
389 deaths. $2.17 trillion in wealth. 6 helicopter crashes.
Here's what I found.

[Andrew Wilkinson @awilkinson]

Every financial journalist seems to be shouting about how we’re in a datacenter bubble.

The bears say that OpenAI and Anthropic are burning money, and that AI isn’t adding real economic value.

It reminds of how people attacked Google in the early days because it didn’t have a business model (we all know how that turned out).

I would argue that:

1. Nobody is going back to traditional search.

We increasingly demand the intelligence, reasoning, and analysis that LLMs provide.

This requires inference compute (in addition to massive amounts of training), which requires datacenters.

Insatiable demand for compute is here to stay, and it’s going to keep compounding for decades.

2. OpenAI has captured consumer intent far beyond Google Search.

Monetization is only a matter of time (they are slowly rolling this out, but I expect it will quickly become one of the world's greatest businesses).

3. If you want to demonstrate economic value from AI, look no further than the world of programming.

Talented programmers were previously one of the world’s most finite and expensive resources.

Now, 100 of them live in my Mac’s terminal in Claude code.

Me and my companies are pouring tens of thousands of dollars into Claude credits each month because it’s finally delivering real, economic value—doing $200,000 of human work with $5,000 of AI tokens.

This is about to ripple through the entire economy, delivering GDP growth, massive amounts of innovation, and empowering everybody to build.

Ignore the noise. LFG.

(Keen to hear from the bears 🐻)

[John Arnold @johnarnold]

Just returned from my first trip to China, mostly looking at the energy and robotics industries. Fascinating. Random observations, both business and general, below...
1/x

[Miss Ally @MissAlly_01]

I run every day for 20 minutes & if I miss a day, I add 20 minutes to the next day. This has truly been a game changer. Tomorrow, I'm supposed to run for 4 months.

[Guido Appenzeller @appenz]

One hour Waymo ride from San Francisco to Menlo Park via highway 280. It’s over, cars are self-driving. Everything else is just about rolling this out to the rest of the world.

[Simon Moore @simonwmoore]

What Hassett As Potential Fed Chair Would Mean For Interest Rates via @forbes https://t.co/ONdbIhhBVf

[Simon Moore @simonwmoore]

As Government Shutdown Risk Looms, Here’s The Likely Market Impact via @forbes https://t.co/ksiVtqpHuR

[Gavin Baker @GavinSBaker]

Google’s dominance of the Pareto frontier for AI has been shattered.

And actually wild that Grok 4 Fast *also* has a 2m token context window.

[Simon Moore @simonwmoore]

@SteveMiran I should clarify that these forecasts are anonymous, so could theoretically be any committee member, but this is the main change since the June projections with Miran the only new member.

[Simon Moore @simonwmoore]

Welcome to the #FOMC @SteveMiran

[Greg Ip @greg_ip]

This chart illustrates why it's so hard to decide whether the economy is getting better or worse. Nominal wage income has decelerated, as nominal retail sales have picked up. One possible explanation: consumption is increasingly driven by stock market gains rather than income.

[Aaron Levie @levie]

There really are 2 different worlds of AI adoption right now. Most individuals, teams, and organizations have *finally* gotten around to implementing AI chat systems for the first time.

But this is happening at the exact same moment when it’s getting clearer what the future of AI agents are going to look like.

The type ahead or chat interaction paradigm of AI maxes out at double digit productivity gains because you’re inherently rate limited by how fast you can type or interact with the system. You’re still doing most of the work, and AI is just providing quick answers and suggestions to move you along faster.

The AI agent model, where you can run many agents in the background in parallel, actually can deliver multiples in productivity gains. Coding is where we’re seeing this first, but it will come for most categories of knowledge work.

The only trick is that it’s likely not as easy to adopt as the first paradigm was, because it requires a change in workflow. But those that get there are going to see the future faster, and get more compounding returns, than those that don’t.

[Shawn Gorham @shawngorham]

I want to share something deeply personal, I hope you will find the time to read this:

I have some friends I attended church with in the past. They left church and started leaning left/liberal on key social justice issues where Christians have a firm stance. They became very political posting non stop on current issues like George Floyd, abortion, LGBTQ, Trump, Charlie Kirk and all other hot button topics and current events.

I found myself filled with anger reading their posts.
"How can they believe that?"
"Are you serious?"
"You are the problem with the world today"

With every post more enraged but disciplined enough not to comment or engage.

Based on their posts, we have nothing in common anymore. Anger filled my heart towards past friends.

Then last week he called me for a Real Estate question/advice!

We laughed, he was funny, he asked about all my kids, told me about his. It was a life giving 45 minute phone call with an old friend who I deeply enjoyed in the past and again in that moment.

Moses has this line he said to me (many times now) "I think you two have more in common than you dont"

Social media is dividing us. I found myself thinking things about a friend I would never ever say to him in person. He is not my enemy. I believe he loves me very much and would do anything for me if I called him.

We dont have to agree on politics or hot topic devisive subjects, we dont. I can lean conservative, you can lean liberal and we can still have a good relationship even though we dont agree, we can, I promise.

If I only engaged with those whos beliefs lined up with mine, my life would not be as good as it is today, it wouldnt

We need to lower the tone. You can still be bold, you can still proclaim your beliefs, but you dont have to hate your neighbor to do it.

Social media is dividing us. We have to fight against it.

[Simon Moore @simonwmoore]

What To Look From The Fed’s September Meeting via @forbes https://t.co/jBMq86F5vK

[Simon Moore @simonwmoore]

Online travel platforms prepare for rise of artificial intelligence ‘agents’ https://t.co/YCChgBGawZ via @ft

[Jim Gillies @JimPGillies]

I hate that this exists. I love that this exists. I don’t want to buy it. I’m gonna buy it.

(And if I don’t, Lulu will.)