Joshua Webster

In CA this month, we’re literally required as a venture firm to ask each of our CEO’s in a survey if they are gay. Meanwhile today in Texas the voting machine is like, Y or N, “Ban gender nonsense in K-12?” “Ban sharia law?” 🇺🇸

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 admire your work with YC and agree start ups are key. Would you support 1000 trade schools, an industrial development bank, AI literacy in K-12, tech job centers across California & America, $10 day childcare (for care jobs), high pay for home care workers with AI tools, Medicare for All so we don't have job lock and can have more founders, an open social web to allow portability of social media graph...there may be some overlap.

I met today with the founder of Starcloud and I realized this is going to be one of the biggest engineering projects of our era. When you look at the tradeoffs, it seems inevitable that all the GPUs are going to live in space.

We just raised $5.6m from our top customers on Frec, and the round was oversubscribed in under 48 hours! Here’s how it all went down. Customers have been asking to invest in Frec since we launched, so we kept track of those who asked, provided valuable feedback, or referred customers. The list started growing quickly after launching long short. Although we had the bulk of our Series A still in the bank, we saw an opportunity to make our top customers owners in Frec. So I pitched the idea to the board. The pitch was simple. Customers who want to invest work at some of the most impressive companies in the world, like Nvidia, Meta, Apple, Netflix, Snowflake, Databricks, Stripe, Shopify, Uber, Robinhood, Plaid, Workday, Block, Two Sigma, JP Morgan, and more. Their colleagues are exactly the type of people who could benefit from Frec the most. Offering these customers ownership would create an incredible customer advisory board. The board agreed. And when I sent the invites to the customers, the reactions were heartwarming: “Heck yes, I’m 100% in. Thank you for thinking of me for this. I’d love to be part of it. You know I’m very bullish on Frec’s future.” “I am impressed with how smart it is to engage your best customers with ownership this way.” “I'm glad to be a customer and now glad to be an investor. Eager to see how things grow and develop.” …and many more 🙏 So we raised the money in a YC SAFE note for a fast and efficient close, and we used an AngelList Roll Up Vehicle (RUV) to keep our cap table clean. I’m excited to welcome our newest investors. We always value customers who engage with us and hope to include more of them as investors in future opportunities.

We just raised $5.6m from our top customers on Frec, and the round was oversubscribed in under 48 hours! Here’s how it all went down. Customers have been asking to invest in Frec since we launched, so we kept track of those who asked, provided valuable feedback, or referred customers. The list started growing quickly after launching long short. Although we had the bulk of our Series A still in the bank, we saw an opportunity to make our top customers owners in Frec. So I pitched the idea to the board. The pitch was simple. Customers who want to invest work at some of the most impressive companies in the world, like Nvidia, Meta, Apple, Netflix, Snowflake, Databricks, Stripe, Shopify, Uber, Robinhood, Plaid, Workday, Block, Two Sigma, JP Morgan, and more. Their colleagues are exactly the type of people who could benefit from Frec the most. Offering these customers ownership would create an incredible customer advisory board. The board agreed. And when I sent the invites to the customers, the reactions were heartwarming: “Heck yes, I’m 100% in. Thank you for thinking of me for this. I’d love to be part of it. You know I’m very bullish on Frec’s future.” “I am impressed with how smart it is to engage your best customers with ownership this way.” “I'm glad to be a customer and now glad to be an investor. Eager to see how things grow and develop.” …and many more 🙏 So we raised the money in a YC SAFE note for a fast and efficient close, and we used an AngelList Roll Up Vehicle (RUV) to keep our cap table clean. I’m excited to welcome our newest investors. We always value customers who engage with us and hope to include more of them as investors in future opportunities.