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'Work hard, stay loyal, and the system will reward you': the Boomer credo is a Gen X betrayal and a Millennial pipe dream

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Startups & VenturePayPal Holdings

Exclusive: PayPal winds down venture arm as fintech giant restructures under new CEO

By
Ben Weiss
Ben Weiss
Crypto Reporter
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By
Ben Weiss
Ben Weiss
Crypto Reporter
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June 16, 2026, 3:53 PM ET
Enrique Lores, president and CEO of PayPal.
Enrique Lores, president and CEO of PayPal.Annabelle Chih—Bloomberg/Getty Images
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PayPal is shuttering its 10-year-old venture team amid a broader corporate shakeup, according to five sources familiar with the matter. The fund’s headcount has shrunk from more than 10 in late 2025 to now only two, according to an archived version of the website for PayPal Ventures. Meanwhile, the page that listed the venture unit’s employees is no longer visible.

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PayPal is also exploring the sale of some of its positions on the secondary market and has hired the investment bank Jefferies to help with potential transactions, said one source familiar with the matter, who declined to be named while talking about private business dealings. 

“As part of our continued efforts to sharpen our focus, we are exploring strategic options for our corporate venture capital arm, PayPal Ventures,” a company spokesperson said in a statement. “We don’t have additional details to share at this time.”

A spokesperson for Jefferies didn’t immediately respond to a request for comment.

PayPal established its venture arm in 2016, one year after eBay spun off the fintech into an independent company. Since then, PayPal Ventures, which invests off the fintech’s balance sheet, has backed more than 80 companies across three funds that total more than $850 million. Some of its more prominent bets include the fintech Plaid, the crypto custodian Anchorage Digital, and its exits include Bill.com’s acquisition of the startup Divvy in 2021.

The performance of the venture fund’s portfolio contributed 10 cents to PayPal’s $1.53 earnings per share in the fourth quarter of 2025, as opposed to subtracting four cents in 2024, according to a February earnings release.

Other prominent public companies, including Google and Microsoft, maintain significant venture units.

‘Recommit to the fundamentals’

The wind-down of PayPal’s venture team comes after the fintech’s prior CEO Alex Chriss stepped down in February. During Chriss’s almost-three-year tenure, the company’s stock had dropped more than 30%, and the board of directors worried that the payments firm was falling behind competitors, including Stripe and Apple, which have their own checkout products. “The pace of change and execution was not in line with the Board’s expectations,” read a press release announcing the transition. 

In Chriss’s place, PayPal appointed Enrique Lores, who was previously the president and CEO of the consumer device giant HP. The new executive quickly promised to revamp the fintech. He put the consumer payments app Venmo into a separate business vertical, restructured leadership, and spearheaded a sweeping set of cuts announced in May. PayPal is reportedly targeting layoffs of 20% of its staff over the next two or three years. 

Lores said in a May earnings call that the fintech needed to accelerate “AI adoption” and “recommit to the fundamentals.” The company intends to deliver at least $1.5 billion in savings over the next two to three years, said another PayPal executive during the call.

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