Why PayPal Is Now My Portfolio's Largest Position

I bought my first [$PYPL](https://x.com/search?q=%24PYPL&src=cashtag_click) shares in January 2023. 1,009 days later, the stock price is lower, but I kept buying. Today, PayPal is my largest portfolio position, here is why. In my article, I explain why I’ve made **PayPal** the largest position in my portfolio, despite the stock being deeply out of favor. The core of my thesis is not short-term growth optimism, but a structural mispricing driven by narrative fatigue, misunderstood fundamentals, and what I describe as **demand asymmetry**. The market largely treats PayPal as a stagnating legacy fintech, yet its underlying business continues to generate strong cash flows, earnings, and shareholder returns. The disconnect between perception and economic reality has created an unusually attractive setup. A key part of my analysis is comparing today’s price to 2017, not just nominally, but **in real, inflation-adjusted terms**. Since 2017, cumulative U.S. inflation has been roughly 30%+. This means that a PayPal share trading around the mid-$50s today is equivalent to paying roughly low-$40s in 2017 dollars. In other words, even though the stock price appears flat over many years, investors are actually paying significantly less in real purchasing-power terms than they were nearly a decade ago. This is especially striking given that the company today is larger, more profitable, and far more cash-generative than it was at that time. The most important concept in the article, however, is demand asymmetry. In 2017, PayPal had a much larger share count and a very different shareholder base. Growth and momentum investors dominated ownership, and rising prices were met with ample selling pressure. Today, the situation is structurally different. Through aggressive buybacks, the share count has fallen materially, meaning each marginal dollar invested now buys a larger percentage of the business than it did in the past. At the same time, many short-term or narrative-driven holders have already exited. What remains is a shareholder base with stronger hands, investors focused on cash flow, valuation, and long-term ownership rather than short-term price action. This creates an asymmetric setup where **future demand has a much larger impact on price than it used to**, while supply has become structurally constrained. Even modest positive shifts in sentiment, fundamentals, or capital allocation can move the stock disproportionately, because there are fewer willing sellers and fewer shares available. In 2017, PayPal needed massive inflows just to maintain valuation levels. Today, it needs far less incremental demand to reprice meaningfully upward.