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Hello, Fintech Friends!

They say the only constant in life is change. For PayPal, the last couple years have been filled with new beginnings (and one abrupt end).

Former CEO Alex Chriss (who took over for Dan Schulman in 2023) overhauled PayPal’s senior leadership and moved aggressively into new areas like stablecoins, agentic commerce, and advertising, but was ousted just over two years after promising to “shock the world” as PayPal’s core checkout experience atrophied and share loss accelerated.

Enter Enrique Lores, who replaced Chriss as PayPal’s CEO on March 1 (and has been a member of PayPal’s board for nearly five years). Last week, at Lores’ direction, PayPal announced it was reorganizing the company into three distinct segments: one centered around PayPal’s core checkout features; one placing Venmo at the center of an aspirational digital financial services brand; and one with PayPal’s processing assets, including Braintree, and other merchant value-added services.

Although some people believe the reorganization is designed to ease the sale, or separation, of parts of PayPal, a transaction (at least to my untrained eye) does not appear imminent, suggesting PayPal believes work may be needed before shareholder value can be maximized. That makes PayPal’s lack of a more developed strategic plan to share on the first quarter earnings call all the more baffling.

While Lores highlighted PayPal’s “strong foundation” and a “framework” for defining the company’s strategy, he suggested it will take a “few months” before a fully developed plan is implemented (and presumably shared). The lack of financial statements or detail to accompany the newly created segments was also disappointing as key questions about profitability (especially for Venmo and Braintree) must be answered before investors and analysts can begin to confidently quantify a fair value for the different parts of PayPal.

In terms of actual results, PayPal’s solid first quarter performance was overshadowed by weaker second quarter guidance and some cautious commentary. Specifically, branded online checkout TPV growth ticked up to 2% during the first quarter, but was running at the “low-end” of PayPal’s full-year expectation for “slightly positive to low single-digit growth” during the second quarter as PayPal highlighted weakness in the travel vertical and Europe. Finally, after growing 3% during the first quarter, PayPal expects transaction margin dollars excluding interest on customer balances to decline by a low single-digit percentage in the second quarter.

For PayPal, arresting share losses in branded online checkout is imperative to the company’s long-term health. Time is of the essence and multiple shifts (and delays) in strategy (implementation) do not help.

Bob Hammel

p.s. Have feedback? Reach out on X

Charts Corner

Data source: Yahoo Finance

Data source: Yahoo Finance

Data source: Yahoo Finance

Worth Watching

Visa* Reports Strong March Quarter Results

For the first time since the beginning of calendar 2023, Visa’s organic net revenue growth outpaced Mastercard’s: 15% to 12%. Visa’s performance was led by nearly 10% growth in U.S. credit card payment volume and a 27% increase in value-added services (VAS) revenue, which now represents 30% of Visa’s total. Although Visa and Mastercard reported strong results, both presented data showing a slowdown in highly profitable cross-border travel volume during April. Even though some of the April softening is attributable to the Iranian conflict, both companies called out the timing of Ramadan as a contributing factor to April’s slowdown, suggesting underlying momentum is relatively stable.

Disclosure: As of May 6, 2026, I have a long position in Visa.   

FIS and Anthropic Partner on Financial Crimes Agent

FIS announced a partnership with Anthropic to build a financial crimes agent that monitors suspicious activities for FIS’ bank customers with the goal of compressing investigation times and ensuring investigators spend their time making the most critical decisions. FIS employees and Anthropic engineers will collaborate to build the financial crimes AI agent using FIS’ proprietary data. According to FIS, all client data will remain on FIS’ premises, and the FIS and Anthropic collaboration will serve as a roadmap for FIS to build additional future agents independently, including for credit decisioning, deposit retention, customer onboarding, and fraud prevention. BMO and Amalgamated Bank will be the first FIS customers to deploy the financial crimes agent with a broader release planned for the second half of 2026.     

Shopify Falls Despite Strong Results

Shares of Shopify fell nearly 16% despite reporting strong first quarter results, which featured 30% GMV growth and 32% gross profit growth, both on a constant currency basis. While Shopify continues to advance its AI strategy, which includes incorporating AI into everything Shopify does internally (acting as an exoskeleton for employees) and for merchant-facing products like Sidekick (weekly utilization up 4x over the prior year), the market likely harbors lingering concerns over the long-term impact of agentic commerce on Shopify’s business model, which relies in part on subscription fees to create and maintain the online storefronts that attract human shoppers. Additionally, Shopify laid out somewhat disappointing guidance for the upcoming quarter, including approximately mid-single-digit slowdowns in revenue and gross profit growth. Regardless of whether Shopify will benefit or be hurt by AI, a slowdown like the one Shopify is forecasting never bodes well for a stock that is as highly valued as Shopify’s.

Multiples

Data source: Yahoo Finance

Data source: Yahoo Finance

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