We recently published a list of Mark Cuban Stock Portfolio: Top 10 Stock Picks. In this article, we are going to take a look at where Uber Technologies, Inc. (NYSE:UBER) stands against other top stock picks from Mark Cuban’s portfolio.

Mark Cuban is a well-known entrepreneur and television personality, recognized for his diverse business ventures and outspoken presence in the sports and entertainment industries. He was the principal owner of an NBA franchise, the Dallas Mavericks, of which he now serves as a minority owner. Raised in Pittsburgh, Pennsylvania, Cuban showed an entrepreneurial spirit from a young age. At age 12, he sold garbage bags to afford a pair of expensive sneakers after which, at 16, he capitalized on a newspaper strike by transporting newspapers. Later, he enrolled at the University of Pittsburgh before transferring to Indiana University’s Kelley School of Business, where he earned a degree in management in 1981.

Cuban started his career at Mellon Bank, where he developed an interest in technology and networking. After being fired from his sales job in a software retailer, he founded MicroSolutions, a company specializing in system integration and software reselling. Under his leadership, the company flourished, generating over $30 million in revenue before Cuban sold it to CompuServe for $6 million in 1990, netting approximately $2 million after taxes. Cuban’s success continued with Audionet, a company he co-founded in 1995 alongside Todd Wagner. Audionet evolved into Broadcast.com, growing rapidly and generating millions in revenue. In 1999, at the height of the dot-com boom, Yahoo! acquired Broadcast.com for $5.7 billion in stock.

Over the years, Mark Cuban has invested in various industries, including social software, networking, entertainment, sports, and cryptocurrency. He was an early investor in IceRocket, a blog search engine, and backed companies like RedSwoosh, Weblogs, Inc., and Goowy Media. In 2005, he experimented with a new business model for online journalism through Sharesleuth.com and later launched Bailoutsleuth.com for government oversight. Cuban also ventured into film distribution with Magnolia Pictures and invested in Motionloft, a storefront analytics company. His Shark Tank investments since 2011 total nearly $20 million, with mixed success. In 2022, he launched Cost Plus Drugs to lower prescription prices and disrupt the U.S. healthcare industry. His sports ventures include owning the Dallas Mavericks from 2000 until selling a majority stake in 2023. Cuban has also been active in cryptocurrency, accepting Dogecoin for Mavericks merchandise and tickets.

Mark Cuban’s investment philosophy is centered on discipline, frugality, and informed decision-making. He emphasizes “living like a student” in the early years to build a financial cushion, saving at least six months’ income before investing in low-cost index funds. Cuban strongly discourages credit card debt due to high interest rates, advocating for cash or debit card use instead. He also promotes strategic spending by negotiating prices and buying essentials in bulk when discounted. For more experienced investors, Cuban suggests deep expertise in a particular domain and holding cash until a unique opportunity arises, rather than following conventional buy-and-hold strategies. Ultimately, his approach prioritizes financial discipline, smart spending, and long-term investing for steady wealth growth.

The outspoken tech mogul has a well-defined investment strategy focused on generating wealth through smart, long-term decisions. He favors dividend-paying stocks, referring to them as “real-world value generators,” emphasizing their ability to provide steady income rather than relying solely on price appreciation. In the rapidly evolving AI sector, Cuban sees massive potential, believing that AI will be essential for every company’s survival. Comparing AI investments to buying Apple stock in the 1980s, he considers them the future of passive wealth. As he puts it, “Non-dividend stocks are basically baseball cards. But AI? That’s a whole different game.”

Cuban also acknowledges the high-risk, high-reward nature of cryptocurrency investments but warns investors to be cautious. He advises only investing in what one can afford to lose and focusing on cryptocurrencies with real-world applications. His stance is clear: “If you’re not a true adventurer, stay away.” For those seeking a more stable approach, he recommends the broader market, which has historically delivered reliable returns of around 10% annually. Additionally, his involvement with private companies through “Shark Tank” highlights the potential of venture capital, though he recognizes that most investors may need to turn to crowdfunding or venture funds to access similar opportunities.

Our Methodology

The stocks listed below were picked from the public comments that Cuban has made on his investments. He has explicitly mentioned some of his private holdings during these public appearances while only alluding to others. However, based on a careful assessment of the comments, the stocks listed below largely align with his investment philosophy. The list is compiled in descending order of the number of hedge funds having stakes in each firm, which was derived using data from over 1,000 hedge funds tracked by Insider Monkey in the fourth quarter of 2024.

Why are we interested in the stocks that hedge funds pile into? The reason is simple: our research has shown that we can outperform the market by imitating the top stock picks of the best hedge funds. Our quarterly newsletter’s strategy selects 14 small-cap and large-cap stocks every quarter and has returned 373.4% since May 2014, beating its benchmark by 218 percentage points (see more details here).

Uber Technologies, Inc. (NYSE:UBER)

Number of Hedge Fund Holders as of Q4: 166

Although Mark Cuban once had the opportunity to invest in Uber Technologies, Inc. (NYSE:UBER), he passed on it – a decision he regretted for at least nine years. Cuban had previously invested in Uber CEO Travis Kalanick’s first startup, Red Swoosh, but hesitated when Kalanick pitched the idea of Uber to him, citing concerns over regulatory battles with taxi associations and transportation authorities. After questioning Uber’s valuation, he never heard back from Kalanick, and the company was founded in 2009 and went on to revolutionize the transportation industry. Reflecting on his missed opportunity at the SXSW Conference in Austin, Texas in 2017, Cuban admitted that Kalanick’s willingness to challenge regulations ultimately led to Uber’s massive success. Acknowledging his mistake, Cuban emphasized that he now seeks bold, world-changing ideas, encouraging entrepreneurs to present disruptive innovations without fear of obstacles.

On February 05, 2025, Uber Technologies, Inc. (NYSE:UBER) reported its financial results for Q4 and the full year ending December 31, 2024, highlighting its strongest quarter to date. CEO Dara Khosrowshahi credited the company’s success to accelerated growth in monthly active platform consumers (MAPCs), trips, and gross bookings. He emphasized Uber’s ongoing innovation, particularly in autonomous vehicles, as a key driver of momentum heading into 2025. CFO Prashanth Mahendra-Rajah echoed this optimism, noting record-breaking demand in both Mobility and Delivery services. He stated that the company surpassed its three-year outlook for gross bookings, adjusted EBITDA, and free cash flow, and despite these strong fundamentals, the company still sees itself as undervalued, with plans to actively repurchase stock.

Uber Technologies, Inc. (NYSE:UBER)’s financial performance in Q4 2024 reflected this momentum, with trips increasing 18% year-over-year to 3.1 billion, averaging around 33 million trips per day. Revenue surged 20% from Q4 2023 to $12.0 billion, with Mobility and Delivery revenue climbing 23% to $10.7 billion. With strong demand across its services and a focus on long-term strategy, Uber continues to position itself for sustained growth in 2025 and beyond.

Ariel Appreciation Fund stated the following regarding Uber Technologies, Inc. (NYSE:UBER) in its Q4 2024 investor letter:

“During the quarter, we initiated three new investments, each in companies we have followed closely for a considerable time. At various points, we viewed them as missed opportunities; however, our experience with Mr. Market has taught us that patience often creates inevitable entry points. This quarter, some exciting opportunities presented themselves. The three investments are Amazon (NASDAQ: AMZN), Diageo (NYSE:DEO), and Uber Technologies, Inc. (NYSE:UBER). We will discuss each in detail below

At the halfway point of the year, Uber was one of the top-performing stocks in the S&P, and we couldn’t help but kick ourselves for having spent considerable time researching the company—demonstrating gen[1]uine interest—only to never invest a dime. By year-end, however, Uber’s stock had not only surrendered all its gains but had fallen even further. So, what changed? Hype, plain and simple. Specifically, hype surrounding fully autonomous vehicles (AVs).

While we are excited by the advancements toward full autonomy and have friends who rave about their experiences with Waymo, the narrative (there’s that word again!) surrounding the inevitability of AVs has become so pervasive that it’s taken on a life of its own in markets…” (Click here to read the full text)

Overall, UBER ranks 4th on our list of top stock picks from Mark Cuban’s portfolio. While we acknowledge the potential for UBER as an investment, our conviction lies in the belief that some AI stocks hold greater promise for delivering higher returns and doing so within a shorter time frame. If you are looking for an AI stock that is more promising than UBER but that trades at less than 5 times its earnings, check out our report about the cheapest AI stock.

READ NEXT: 20 Best AI Stocks To Buy Now and 30 Best Stocks to Buy Now According to Billionaires

Disclosure: None. This article is originally published at Insider Monkey.