PayPal’s Big Bet on TV Ads Meets a Contrarian Billionaire’s Vote of Confidence

The payment giant is placing a wager on advertising that connects directly to the checkout counter, while one of Wall Street’s most famous skeptics is quietly building a stake in the company.

On April 22, 2026, PayPal officially launched “Curated Ads,” a platform designed to bridge the gap between television commercials and actual purchases. The service targets the connected TV market and the open web, offering advertisers something the industry has long chased: proof that an ad led to a real sale, not just a click.

The mechanics are straightforward. Instead of counting impressions or engagement metrics, PayPal links ad exposure directly to confirmed transactions within its payment ecosystem. With roughly 25 billion transactions processed annually across its network, the company has a data advantage that few rivals can match. Mark Grether, PayPal’s advertising chief, puts it bluntly: the industry has historically measured purchase intent. PayPal now measures actual purchases.

Where this differs from traditional retail media networks is scope. Amazon and Walmart can only track purchases on their own platforms. PayPal, by contrast, follows buying behavior across millions of merchant sites wherever its payment services are embedded.

The push into advertising is no sideshow. PayPal’s core checkout business is growing more slowly than it once did, and with 439 million active accounts, the company sits on a trove of transaction data it has barely monetized. There is also a tailwind from industry dysfunction: according to the Association of National Advertisers, programmatic ad waste has surged 34 percent over the past two years. PayPal’s pitch—delivering verifiable purchase data—gives advertisers a compelling reason to listen.

The advertising capabilities are also slated for integration into Venmo, PayPal’s peer-to-peer payment app, which counts roughly 100 million US users and has generated little revenue to date.

The stock market has yet to reward the strategy shift. PayPal shares trade at around EUR 42, more than 14 percent below their level at the start of the year and well off the 52-week high.

A Contrarian Takes the Other Side

While the broader market remains cautious, Michael Burry has emerged as a notable buyer. The investor, famous for betting against subprime mortgages before the 2008 financial crisis, has built a position of roughly 3.5 percent in PayPal. His entry price was around USD 49 per share.

Should investors sell immediately? Or is it worth buying PayPal?

Burry views the recent selloff in software stocks not as a reflection of fundamental weakness, but as a technical chain reaction tied to private credit markets—an area where PayPal has no exposure. That isolation, in his view, makes the stock attractive. The disclosure triggered a surge of activity on platforms like Stocktwits, where message volume around the stock nearly doubled.

Wall Street analysts remain far more measured. BMO Capital Markets initiated coverage with a neutral rating and a USD 52 price target, pointing to intense competition from Apple Pay, Shopify, and Stripe. The company is also navigating its third leadership change in a short span, which carries operational risk.

Of the 44 analysts covering PayPal, only ten rate it a buy. The majority recommend holding the shares.

The caution is rooted in recent history. In February, the stock cratered more than 20 percent in a single day after weak earnings and the departure of CEO Alex Chriss. Enrique Lores, the former board chairman known for operational discipline, took over in March.

The stock has shown some recovery, gaining roughly 12 percent over the past 30 days to trade at EUR 43.10. Still, it remains down about 13 percent year-to-date. Rumors of a potential activist investor have also provided support in recent sessions.

The Earnings Test

Both narratives—the advertising pivot and the contrarian bet—converge on May 5, when PayPal reports first-quarter results before the market opens. The report will serve as the first major test for CEO Lores. Investors will be watching for signs of merchant adoption of Curated Ads, margin trends in the new advertising business, and progress on the core branded checkout growth that management has flagged for the year.

If Lores can deliver on those targets, it could lay the groundwork for a sustained recovery. If not, even a billionaire’s endorsement may not be enough to reverse the stock’s fortunes.