We have some exciting news to share! The Motley Fool UK has now become The Twelfth Magpie -- an independent, UK-owned company, led by our long-serving UK management team — Mark Rogers, Chris Nials and Heather Adlington. In practical terms, it’s the same team you know, now fully focused on serving our UK readers and members.

Just as importantly, our approach remains unchanged: long-term, jargon-free, and on your side. This site is our new home, and there will be extra tweaks made across the coming few days as we settle in. So if anything looks a little off, please bear with us!

The content of this article was relevant at the time of publishing. Circumstances change continuously and caution should therefore be exercised when relying upon any content contained within this article.

1 simple question for investors looking at buying PayPal shares

Stephen Wright’s short on reasons to buy shares in a company that has 25% of its free cash flow offset by stock-based compensation costs.

| More on:
Woman using laptop and working from home

Image source: Getty Images

You’re reading a free article with opinions that may differ from The Motley Fool’s Premium Investing Services. Become a Motley Fool member today to get instant access to our top analyst recommendations, in-depth research, investing resources, and more. Learn More.

Investors rushed to buy PayPal (NASDAQ:PYPL) shares on Tuesday (28 October) after the firm announced a deal with OpenAI. But I’ve a big question about the stock for investors.

Over the last 10 years, PayPal’s free cash flow has been around $46bn. So my question is pretty simple: where’s all that money gone?

XXX

Where’s the money gone?

Spoiler alert: I’m not saying there’s anything untoward with PayPal or its accounting practices – to the best of my knowledge, there isn’t. But its cash does just seem to disappear.

The company hasn’t paid a dividend in the last 10 years, so all its cash has been retained in the business. But the firm’s book value has only increased by about $12bn. 

Share buybacks are another part of the story, but PayPal’s only reduced its share count by around 15% in the last decade. Based on the current market-cap, that’s around $10bn.

That still leaves about half of the company’s free cash flow unaccounted for. And this is a question anyone even thinking of buying the stock needs to find an answer to. 

Stock-based compensation

A big part of the answer is stock-based compensation. These are stock options PayPal gives its employees as part of their overall salary. Since they aren’t cash expenses, they don’t affect free cash flow. But the firm has to offset this with share buybacks to avoid diluting its existing shareholders – and that does use up cash.

PayPal’s stock-based compensation expenses since 2015 have has been around $11.2bn. So offsetting this with share repurchases accounts for around 25% of the firm’s free cash.

On the face of it, the stock looks cheap at a free cash flow multiple of around 13. But this is based on entirely ignoring stock-based compensation, which I think is entirely unjustifiable.

OpenAI

The latest news pushing the stock higher is the deal with OpenAI. ChatGPT’s moving into e-commerce and PayPal’s signed a deal to facilitate payments. If this is the future of e-commerce, there’s no doubt it’s where the company needs to be. And while it’s a key reason for long-term optimism, it raises yet more questions.

It isn’t clear, for example, whether the firm’s going to be the exclusive payment provider or just an option. And there isn’t yet confirmation of how the fee structure will work. 

If PayPal’s going to be the sole payment processor on ChatGPT with a promising cut of sales, the potential’s huge. But this hasn’t been confirmed, so investors can’t count on it. 

Sell?

I think PayPal’s share price surging is an opportunity. But I see it as a chance for investors who own the stock to consider getting out of it.

Stock-based compensation costs mean the share price isn’t as cheap as its free cash flow multiple makes it look. And the OpenAI deal is – so far – very light on details. 

Maybe this develops into something more promising. But for now, I think investors should seriously think about whether they can’t find better buying opportunities elsewhere.

Stephen Wright has no position in any of the shares mentioned. The Motley Fool UK has recommended PayPal. Views expressed on the companies mentioned in this article are those of the writer and therefore may differ from the official recommendations we make in our subscription services such as Share Advisor, Hidden Winners and Pro. Here at The Motley Fool we believe that considering a diverse range of insights makes us better investors.

More on Investing Articles

Friends and sisters exploring the outdoors together in Cornwall. They are standing with their arms around each other at the coast.
Investing Articles

£503 buys 14 shares in this FTSE 250 stock that returned 23.9% annually for the last 15 years

This FTSE 250 stock has averaged a huge return for 15 years. At today's price, £503 buys 14 shares. But…

Read more »

Black woman using loudspeaker to be heard
Investing Articles

£1,000 buys 25 shares in this FTSE 100 stock that’s returned 29.2% annually for the last 10 years

This FTSE 100 mining stock has returned close to 30% a year for a decade. At 3,995p, £1,000 buys 25…

Read more »

Female student sitting at the steps and using laptop
Investing Articles

Down 47%, is this growth stock finally worth buying in May?

With a £288m order book and a hidden pipeline of defence and nuclear contracts, is this growth stock now too…

Read more »

House models and one with REIT - standing for real estate investment trust - written on it.
Investing Articles

2 REITs yielding 7%+ to consider for passive income in 2026

A REIT backed by the NHS and another backed by Tesco and Sainsbury's with both yielding 7%+. Here's why I'm…

Read more »

Woman riding her old fashioned bicycle along the Beach Esplanade at Aberdeen, Scotland.
Investing Articles

Just 97 shares of this UK dividend stock generate £238 in passive income

A 5.7% yield, £238 in passive income from just 97 shares, and one of the most divisive dividend stocks on…

Read more »

ISA coins
Investing Articles

£10,000 in an ISA generates a second income of…

The London Stock Exchange is home to some of the world's most generous dividends. But how big a second income…

Read more »

Shot of a senior man drinking coffee and looking thoughtfully out of a window
Investing Articles

Expert recommendations: 2 top income stocks yielding 7%+!

With yields of 7.2% and 7.8% respectively, these two income stocks are catching the eyes of institutional analysts. Should investors…

Read more »

Illustration of flames over a black background
Investing Articles

3 top income-focused stocks to buy in May 2026, according to experts

Looking for a stock to buy for income in May 2026? Experts have flagged these three UK dividend shares as…

Read more »