To The Moon

$Uber(UBER)$

Performance Overview: From Money-Losing Startup to Market Star

Uber’s stock has been on a tear. If you had invested $10,000 into the ride-hailing company three years ago, your investment would now be worth more than $30,000. That represents a gain of over 300%—nearly five times the return of the S&P 500 over the same period. Few large-cap tech stocks have delivered such an extraordinary performance in recent years.

What makes this rally even more striking is Uber’s competitive cohort. Over the last three years, household names like Microsoft, Apple, Google, and Tesla have all posted respectable returns, but Uber has outpaced them by at least threefold. For a company once known for cash burn, regulatory battles, and skepticism about whether it could ever be profitable, Uber’s resurgence has been nothing short of remarkable.

Yet this dramatic turnaround raises an important question: has Uber’s rally already run its course, or is there more upside left?

Enter Bill Aman: High-Conviction, High-Risk

To answer that, we need to examine the actions of one of the world’s most closely watched investors: billionaire Bill Aman. In the first quarter of 2025, Aman stunned markets by disclosing that his fund had accumulated more than 30 million shares of Uber—a $2.3 billion position. Not only is this an enormous financial commitment, but it also makes Uber his single largest holding.

Aman is not the kind of investor who takes small positions. His style is built around high-conviction bets that either generate legendary profits or catastrophic losses. His track record is filled with both.

On the winning side, Aman is remembered for his post-financial-crisis bet on General Growth Properties, a bankrupt mall operator. While most investors had written the company off, Aman stepped in, provided capital, and held on through the recovery. The trade became one of the greatest distressed-investing victories of all time, returning more than 100 times the original investment.

In 2012, he orchestrated a turnaround of Canadian Pacific Railway by installing new leadership and streamlining operations. The result was a tripling of the stock price within just a few years, proving his ability to engineer operational transformations in legacy industries.

But for every triumph, Aman has endured costly setbacks. His 2015 investment in Valeant Pharmaceuticals collapsed spectacularly, costing him nearly $4 billion. His high-profile short position in Herbalife, a battle he fought loudly for five years while calling the company a pyramid scheme, ended in a humiliating defeat with steep losses.

This duality—epic wins and crushing defeats—defines Aman’s reputation. When he makes a move, markets take notice. His Uber investment has therefore become one of the most hotly debated trades on Wall Street today.

Uber’s Financial Turnaround: From Cash Burn to Cash Machine

At the core of Aman’s Uber thesis is the company’s financial transformation under CEO Dara Khosrowshahi. When Uber went public in 2019, it was known more for its staggering losses than for its disruptive potential. The company routinely burned billions of dollars a year, subsidizing rides and food deliveries in a bid for market share. Many analysts doubted whether the business model could ever achieve sustainable profitability.

Fast forward to today, and the picture has changed dramatically.

• Free Cash Flow: In 2022, Uber turned free cash flow positive for the first time. This is a crucial milestone, as free cash flow measures how much money a company generates after covering expenses and capital investments. For years, Uber’s negative FCF was a red flag. Today, the company generates billions in excess cash annually.

• Net Income: In 2023, Uber posted its first full year of profitability. After years of outspending revenue, Uber finally proved that its platform could scale profitably.

• Balance Sheet Improvements: Uber has also reduced debt levels and improved liquidity, giving it more flexibility to invest in growth opportunities without resorting to constant capital raises.

These milestones show that Uber has crossed an important psychological threshold for investors: it is no longer a speculative, cash-burning startup. It is a profitable, scalable, and increasingly diversified platform business.

The Hidden Catalysts Driving Aman’s Bullish Case

While the financial turnaround lays the groundwork, Aman’s conviction comes from three underappreciated growth engines that he believes the market has not fully priced in: advertising, freight, and self-driving technology.

1. Advertising: Uber’s Quiet Growth Engine

Uber’s advertising business is perhaps its most overlooked revenue stream. Launched in 2022, the unit has already surpassed $1.5 billion in annual revenue, growing at 60% year over year. Unlike ridesharing or food delivery, advertising is a high-margin business with minimal incremental costs.

Uber’s advantage lies in its captive audience. Millions of riders and eaters use Uber’s apps every day, providing a platform for hyper-targeted ads that can drive immediate consumer actions. Restaurants can promote menu items on Uber Eats, while brands can market directly to ride-hailing passengers.

Given the global scale of Uber’s user base, many analysts see advertising as a potential multi-billion-dollar business that could rival the ad revenues of companies like Amazon’s advertising arm. Aman clearly believes this division could become one of Uber’s most profitable verticals.

2. Uber Freight: Solving Trucking Inefficiencies

Uber Freight is another underappreciated asset. The logistics division functions as a brokerage platform, connecting shippers with trucking companies. By leveraging artificial intelligence and real-time data, Uber Freight optimizes routes and reduces “empty miles”—the industry term for trucks traveling without cargo.

A recent report estimated that roughly 35% of U.S. trucks on highways are empty at any given time. Solving this inefficiency represents a multi-billion-dollar opportunity.

Uber Freight already generates billions in revenue annually, and Aman sees it as a long-term play on modernizing the fragmented trucking industry. If Uber can capture even a modest share of this market, the upside is enormous.

3. Self-Driving Partnerships: The Robo-Taxi Future

The third catalyst is Uber’s push into autonomous vehicles. Rather than developing self-driving technology entirely in-house—a path that proved expensive and risky in the past—Uber has partnered with industry leaders such as Waymo and Aurora.

Waymo’s autonomous cars are already available on Uber’s platform in select markets, with coverage expected to expand significantly in 2025 and beyond. By integrating robo-taxis, Uber could reduce its reliance on human drivers, cut costs, and open up new revenue streams.

While self-driving remains a long-term bet, Aman views Uber’s partnerships as a low-capex way to capture upside from one of the most transformative technologies of the coming decade.

The Risks: Competition and Regulation Loom Large

For all its promise, Uber still faces significant risks that could derail growth.

Competitive Pressures

• Ridesharing: In the U.S., Uber controls about 76% of monthly rideshare sales versus Lyft’s 24%. While Uber enjoys dominance, Lyft remains a viable competitor that forces Uber to keep prices competitive.

• Food Delivery: Here, Uber struggles. DoorDash controls nearly two-thirds of the U.S. market, while Uber Eats holds less than a quarter. Given that delivery contributes about 32% of Uber’s revenue, losing ground here is a serious concern.

• Freight: The logistics sector is crowded, with established brokers and startups all vying for market share. Uber must prove its technological edge translates into durable competitive advantages.

Regulatory Threats

The bigger threat may be regulatory. Uber’s business model hinges on classifying drivers as independent contractors. If U.S. courts or lawmakers force Uber to reclassify drivers as employees, it could add more than $4 billion in annual labor costs.

This is not a hypothetical risk. In the U.K., Uber is already required to pay minimum wage and benefits, significantly raising operating expenses. Similar rulings in the U.S. or Europe could erode profitability quickly.

For Aman’s thesis to hold, Uber must not only execute well but also navigate this minefield of regulatory challenges.

Financial Valuation and Investor Sentiment

As of mid-2025, Uber trades at a valuation that reflects its new profitability but arguably still underprices its future growth. The company’s forward P/E ratio is significantly lower than other large-cap tech peers, partly because investors remain cautious about its regulatory exposure and competitive landscape.

However, bulls argue that if Uber’s advertising and freight divisions scale as expected, the company could command a valuation more in line with other diversified tech platforms. Aman’s $2.3 billion bet suggests he believes Uber’s intrinsic value is far higher than the market currently reflects.

Verdict: High Risk, High Reward

Uber’s stock has already delivered an extraordinary three-year run, but according to Bill Aman, the story is far from over. The company has transitioned from a money-losing disruptor to a profitable platform with multiple high-margin growth engines. Advertising, freight, and self-driving technology provide avenues for future expansion that investors may be underestimating.

At the same time, Uber faces stiff competition and potentially devastating regulatory risks. These risks make it a binary trade: if the catalysts play out, Uber could compound far beyond today’s valuation; if not, the downside could be steep.

Entry Price Zone: For long-term investors, an attractive entry could be in the $65–70 per share range, which provides a margin of safety relative to projected cash flows and industry growth assumptions. Short-term volatility should be expected, particularly around regulatory headlines.

Conclusion: A Classic Bill Aman Trade

Bill Aman’s investment in Uber embodies everything about his style: bold, controversial, and binary. It could become the next Canadian Pacific—a multibagger success story—or another Valeant, a painful reminder of high-conviction gone wrong.

For investors, Uber represents one of the most fascinating opportunities in today’s tech landscape. Its transformation into a cash-generating business, combined with new growth verticals, makes it far more than just a ridesharing app. But the risks are just as real, demanding patience and a tolerance for volatility.

As with many of Aman’s trades, the outcome will likely be remembered for years to come—either as a masterstroke of foresight or a cautionary tale of overconfidence.