RT Dividendology
$PYPL PayPal is now down over 86% in the last 5 years, and 47% in the last year.
The performance has been so bad, they’ve started to become the butt of ‘finance jokes’…
For example, I present to you, the new fear & greed index:
PayPal recently reported earnings, and the stock dropped 20%.
They also replaced CEO Alex Chriss with Enrique Lores, HP’s current CEO.
Is PayPal Failing?
A failing business usually shows:
• Falling revenue
• Collapsing margins
• Shrinking user base
• Weak cash generation
PayPal shows none of those… Yet.
So what’s the problem?
PayPal generates most of its revenue from e-commerce.
E-commerce is growing ~7% annually-
But PayPal’s branded checkout volume grew only 1% this quarter.
Investors fear PayPal is losing market share to Apple Pay, Shopify, and others.
Under new leadership, PayPal is now:
• Deploying full feature packages instead of rolling out one tool at a time
• Creating dedicated teams for top merchants
• Aligning merchant incentives to share in conversion upside
• Investing $1.5–$2B back into growth in 2026
That investment will pressure margins short-term, but it’s aimed directly at stopping market share erosion.
But in my opinion, the real bull case for PayPal right now is the math behind its share buybacks.
As a quick refresher, if a company bought back 50% of its outstanding shares, even without earnings growing or a change in the valuation multiple-
The stock would still double.
So what does this mean for PayPal?
Well, management recently guided towards $6 billion of share repurchases in 2026 alone.
At today’s price of roughly $41 per share, that math becomes very interesting.
$6,000,000,000 ÷ $41 = 146 million shares
That means if the stock price stayed around current levels, PayPal could retire approximately 146 million shares in just one year.
At the end of 2025, they had 959 million shares outstanding.
That’s a reduction of approximately 15% of the entire company in a single year.
Let that sink in.
That means even if:
- Revenue doesn’t grow
- Margins don’t expand
- The valuation multiple doesn’t change
The stock would climb by 15%.
Ironically enough, reducing shares through buybacks also makes it easier for companies to grow their dividend payments over time.
With that being said, PayPal is priced at peak fear, with the market currently pricing in nearly -8% annual free cash flow growth over the next decade.
While the company is undoubtedly facing serious issues and has lost market share, they seem to be priced as if the company is quite literally set to die.
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