Ari A.

Doing EM things in tech places.

[Ari A. @hayd_ari]

Would be really funny if Anthropic moved to the EU after getting Fable blocked by the US 😂

[Ari A. @hayd_ari]

Also - Downtime actually has 2 paying users, which is 2 more than any other side thing I've built 🎉

[Ari A. @hayd_ari]

Credit where it's due - the mobile despatch mode of Codex has been working much better than when I tried to use Claude's a few months ago. Built a new feature and a full app store submission from my phone while chilling at a restaurant in a different country.

[Ari A. @hayd_ari]

🤮🤮
Ambitions have gone from creating superintelligence to being Deloitte.

[Greg Brockman @gdb]

Introducing the OpenAI Deployment Company, which will help businesses maximally succeed with their deployments of AI.

Starting with 150 Forward Deployed Engineers and Deployment Specialists, and $4 billion of initial investment from 19 partners.

[Ari A. @hayd_ari]

Don't mean to diss Coinbase but if you ask your managers to manage 20 ICs AND be hands on in the tech - oh boy are you going to have a fun time. No IC who cares about their growth should be joining a company where their lead has 19 other reports.

[Ari A. @hayd_ari]

In the middle of building this Claude decided to use my 5h quota after 5 prompts, so I continued with Codex instead. Seems like the field of play is equalising - really happy with Codex so far. Marketing images also the courtesy of Codex.

Now if only I could figure out marketing

[Ari A. @hayd_ari]

Built yet another thing: https://t.co/lrpfetSMXo

You want an app that simply blocks your work apps outside of work hours? Or social media apps in the mornings and evenings? It's for you.

[Ari A. @hayd_ari]

Took me about 15 minutes to go from "I need an app that blocks me out from social media between certain times of day" to having the app working on my phone. Still a surreal feeling.

[Ari A. @hayd_ari]

https://t.co/VaPSXzSl6i

[Elad Gil @eladgil]

In short run, many coming "we are doing layoffs due to AI" PR will be correcting for sins of 2020 era of over hiring versus anything to do w AI

Many larger tech companies could slim down 50% w/o any AI changes

Most AI productivity impact is still around bend

[Ari A. @hayd_ari]

Why bother going public when you can stay private? AI rush proved there's billions you can raise in private markets. https://t.co/yHu8C9jcbm

[Ari A. @hayd_ari]

Yes. And a "nondecision" decision will always:
- create more confusion & distrust
- be perceived materially worse than the equivalent decision that is transparently communicated

[staysaasy @staysaasy]

the more senior you are in an organization, the greater the degree that not making a decision is functionally equivalent to making a decision

[Bridge @Stablecoin]

Bridge has received OCC conditional approval to organize a federally chartered national trust bank. This will enable us to operate stablecoin products and services under direct federal oversight, including:
- Custody
- Orchestration
- Issuance
- Reserves management

Stablecoins are becoming core financial infrastructure. Institutions need regulatory clarity, operational resilience, and scalable systems to build with confidence. A national trust bank establishes that foundation.

[Ari A. @hayd_ari]

Today on Things My Wife Said:

"I forgot the lyrics"

(she was singing the alphabet song)

[Ari A. @hayd_ari]

Late to the party but.. What's a $2B seed round? Should call it a granary round at that point. How will any of these companies' valuations survive a listing? Who's printing this money?

[Ari A. @hayd_ari]

Sums up the UK that it takes 20 years and billions of pounds to just renovate a building complex.

[Politics UK @PolitlcsUK]

🚨 NEW: MPs and peers must vote on two options to restore the Palace of Westminster

1: Fully move-out for 19–24 years (£11-15bn)

2: Phased works over 38–61 years, in which the Lords move out to a conference centre and MPs use their chamber for 2 years from 2041 (£19-39bn)

[Politics UK @PolitlcsUK]

🚨 NEW: MPs and peers must vote on two options to restore the Palace of Westminster

1: Fully move-out for 19–24 years (£11-15bn)

2: Phased works over 38–61 years, in which the Lords move out to a conference centre and MPs use their chamber for 2 years from 2041 (£19-39bn)

[Ari A. @hayd_ari]

It was also the first time I've sat in front of my laptop coding for many hours in.. years. If you got into software engineering because you liked debugging, boy you're going to thrive in the world of building software with coding agents.

[Ari A. @hayd_ari]

Built a thing!

https://t.co/gFYc9KCa64

Since switching from Android to iPhones I've been missing a good replacement for Loop Habit Tracker on iOS. Couldn't find any that did the job, so did it myself with Claude.

[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.