@tamarawinter From 3rd world to first - Lee Kwan Yew (or his direct memoirs, 1st vol.)
The Fire Next Time - James Baldwin
When Breath Becomes Air - Paul Kalanithi
Surely You’re Joking, Mr. Feynman - feynman
FOR THE FIRST TIME IN 53 YEARS, THE KNICKS ARE NBA CHAMPIONS 🏆
New York defeats San Antonio 4-1 in the NBA Finals, capturing their third championship in franchise history!
Fintech was a revolution that digitized the front end of finance
Stablecoins are enabling finance to digitize the backend, and upgrade existing core ledgers
We’re redefining how the world gets paid.
Introducing the Deel stablecoin wallet allowing contractors to hold earnings in DLUSD, earn rewards and spend anywhere.
All on @deel.
Big thanks to our partners at @Stablecoin@privy_io@tempo@Morpho@SentoraHQ for making this possible.
Been thinking more about the “shape” of the organization I want to build (e.g. when should people build big teams?) and came across this @Alex_Danco quote. Most systems changes require parallel effort. You can’t do it alone.
Biggest red flag I hear from early stage founders?
“We’re working on self-serve onboarding”
Your product currently requires you to talk to every new customer?
That’s a good thing.
@krishnanrohit Misleading… sure $20M perhaps for net operational burn
But they spent $200M plus acquiring the Windsurf GTM team with ~200 headcount.
^ that team & their enterprise selling experience, is one of the largest factors in this story so far
I am genuinely stoked for @tempo's new virtual addresses feature that they announced yesterday. I think this could be a real sleeper hit and I'm guessing that most people who don't have first-hand experience building on-chain don't realize it.
In almost 8 years building in crypto I've had to solve the deposit-address problem at literally _every single company_ I've worked at. Every time its the same build out:
Generate a unique address per customer
Sweep funds back to a master wallet
Manage gas in every leaf address
Reconcile timing differences
Handle the edge cases
It's the kind of thing that sounds simple in a design doc and then can end up eating a quarter of your team's roadmap.
It is _so cool_ to make this a protocol primitive - and totally obvious in hindsight. No sweeps, no per-address gas, no state bloat from millions of customer accounts sitting around with minuscule amounts of dust in them.
This is another one of those things that - if you've built any kind of systems in payments before - seems like an absolute no-brainer, yet somehow we don't have any blockchains with virtual accounts as a first-class citizen yet (Solana's ATAs partially get there but you still need to pay rent per account).
Bullish on how much friction this will remove for teams bringing AR / AP on chain and on more protocols bringing more "obvious" payments primitives on chain in general. Hat tip.
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.
I’d put it differently: your business is a direct reflection of your nervous system
(and if you’re not grounded or avoid certain emotions, this will absolutely show up in the company)