The Story of XPO Logistics

This is an honest, raw Paper Hands confession—a mistake that's haunted me for years. When I was relatively new to the stock market, I bought 144 shares of XPO Logistics at $1.44, a huge investment for me at the time.

The shares were underwater for what seemed like an interminable period, but I stubbornly held on, hoping to one day recover my $207 investment. The shares doubled and I continued to hold in spite of the fact that I desperately needed the money.

I held on because I heard Brad Jacobs made a large investment in the company. All of the pundits I followed were talking about him and his proficiency in business, so how could I lose?

The name resonated with me because I worked on-site at Qualcomm in the mid-2000s as a copy machine repairman. Like many other San Diego residents, I was in awe of Dr. Irwin Jacobs, the MIT grad who co-founded Qualcomm in the den of his house and ended up donating millions to charity.

I often parked my 2003 Mitsubishi Lancer beside his son's Lotus and frequently chatted with him and his trainer in the company gym. His trainer was one of the most beautiful women I had ever seen and the experience certainly made an impression.

Under Jacobs' leadership, the share price of XPO skyrocketed. With significant credit card debt and a young daughter, however, I made the difficult decision of cashing out at around $14.

That $207 had turned into $2,016; boy did I feel like a genius!

Survival is the ultimate goal with investing, of course, but watching XPO from the sidelines over the years generated a substantial amount of scar tissue. Spending time thinking about what could have been will drive you crazy, but if I had simply held on it would have been life changing.

With XPO trading above $150 in early 2026, and factoring in the GXO and RXO spin-offs, my original investment could have grown to over $31,000. The power of compound growth in stocks like XPO is truly staggering.

Turns out Brad Jacobs is not related to Irwin Jacobs! (the person I worked out with and parked beside was likely Mark Jacobs). I found this out today after some research. Who knows if I would have held on to the shares or not if I had known that?

If nothing else, this admission is proof I'm willing to be honest and vulnerable here. I had the wrong idea for years, however, it's worth pointing out that research was harder to get back then.

I've sold other winners too early—Netflix, Apple, Google—sometimes out of fear, sometimes out of necessity. The biggest lesson isn't just about numbers or the importance of doing the research; it's about conviction, patience, and understanding your own motivations as an investor.

Curious about the real Brad Jacobs? Check out his bio below.

Brad Jacobs: The Visionary Behind XPO's Transformation

Brad Jacobs is a renowned entrepreneur and dealmaker. Born in 1956, Jacobs built several billion-dollar companies before turning his attention to XPO. In 2011, he invested $150 million in XPO (then Express-1 Expedited Solutions), became chairman and CEO, and launched an aggressive strategy of acquisitions and growth. Under his leadership, XPO became a global logistics powerhouse, spun off GXO Logistics in 2021 and RXO in 2022, and focused XPO on less-than-truckload (LTL) shipping. Jacobs is known for his relentless focus on technology, operational excellence, and shareholder value. In late 2025, he stepped down from XPO and GXO to focus on his new venture, QXO, aiming to disrupt the building products distribution industry.

Final Thoughts

My XPO story isn't just about missed financial opportunity—it's about learning, growth, and the importance of conviction. Sometimes, life's priorities come first, and that's nothing to regret. But if you're investing for the long term, patience and belief in your decisions can be your greatest allies.

Want more stories and lessons from the trenches of investing? Subscribe to The Pinnacle for real, human insights on building wealth.