Uber (UBER): Cash Machine With a Labor-Law Landmine

Uber just printed about $9B in free cash. The market yawned and asked about robots.
For: growth-tilted investors
Horizon: 5+ years — not a trade

You don’t get to call Uber a science project anymore.

It’s throwing off real free cash flow. It’s investment-grade. It’s buying back stock like management finally believes the story.

The question now isn’t “can this make money?”
It’s “does the model survive the lawyers?”

Core Thesis

Uber is now a real free-cash-flow compounder trading at roughly 20× FCF — attractive if drivers stay contractors in most key markets, a problem if global labor law flips and turns the whole thing into an employer model.

I’m not paying for robotaxis. I’m paying for a scaled, asset-light network that spits cash. Autonomy is upside. Labor law is the kill shot.

The Business in Plain English

Uber is a tollbooth on movement: rides, delivery, and freight. It takes a cut on gross bookings and lets everyone else own the assets.

The numbers finally match that story. Free cash flow went from roughly $3.4B in 2023 to about $6.9B in 2024, and by mid-2025 it was running at around $9B on a trailing twelve-month basis. Revenue and gross bookings are still growing double digits. Trips are up high teens. This isn’t limping along; it’s scaling.

The balance sheet isn’t a fire hazard anymore. Uber is sitting on several billion in unrestricted cash, modest net debt, and leverage around 1× EBITDA. The ratings agencies have it at investment-grade with a stable outlook. That’s a long way from “burn cash and pray.”

Capital allocation finally caught up. In 2024, Uber authorized its first-ever $7B buyback and executed a $1.5B accelerated repurchase under that program. In 2025, the board went further and approved a new $20B repurchase plan. Put together, those authorizations add up to low- to mid-teens percent of the company’s value at recent prices.

Do the rough math: with a market cap in the high-$100 billions and trailing FCF around $9B, you’re paying about 20× FCF — a ~5% FCF yield — for a business still growing that cash pile.

Not a steal. Not stupid either.

Where the Cracks Really Are

There are a lot of headlines. Only one of them can actually break the model.

Driver classification is the real risk.
If big markets force Uber to treat drivers as employees, you’re not tweaking a line item. You’re rewriting the cost structure and killing the flexibility that makes the marketplace work. In a hard version of that world, it’s easy to see 20–30% pressure on profits as benefits, scheduling rules, and rigidity kick in.

Everything else is a sideshow by comparison:

• License and fee fights (London, airports, cities) are a tax on margins, not a death blow.
• AV is real, but Uber is lining up partnerships instead of trying to out-spend Tesla and Waymo on hardware.
• Freight can lose money and still be fixed, shrunk, or sold.

The story doesn’t break because robotaxis exist. It breaks if the law decides the marketplace model itself is no longer acceptable.

What the Market Is Already Pricing In

The market isn’t clueless.

Consensus assumes:

• Revenue keeps growing low- to mid-teens.
• Free cash flow stays in the high single- to low-teens billions over the next few years.
• Margins grind higher as scale, pricing, and ads do their work.
• A premium multiple is justified because this is a dominant global network with optionality on autonomy.

Where I disagree isn’t the base case cash flow. It’s the story people tell themselves.

I’m not buying Uber because I think AV is about to fall into its lap. I’m buying it because the existing rides + Eats engine can keep compounding FCF per share while management retires stock and keeps the balance sheet clean.

If AV works, the equity gets a bonus.
If AV disappoints but drivers stay contractors, the equity is still fine.
If labor law flips hard, the equity has to be repriced.

What Could Actually Move This

Upside over the next 6–24 months is boring in a good way:

• Quarter after quarter of clean FCF and EBITDA beats.
• Buybacks quietly taking a real chunk out of the share count.
• Membership, ads, and product tweaks pushing more spend through the same base.
• AV pilots that show Uber taking a cut on autonomous miles without loading its own balance sheet with cars.

Downside is simple too:

• A major employee-status ruling in a big U.S. state or EU country that obviously sets a template for others.
• Guidance cuts tied to incentives or regulatory costs that don’t roll off.
• AV or freight spend ramping faster than cash flow.

This isn’t a “one headline doubles it” stock. It’s a grinder with a legal overhang.

How It Trades

The market already rewarded the turnaround.

The stock has rerated from “will this ever make money?” to “this is a profitable platform with a premium multiple.” It’s closer to its highs than its lows. Earnings that would’ve sent it vertical two years ago now sometimes sell off, because expectations and factor flows matter as much as the actual print.

This lives in the Growth / Quality / Momentum bucket. It’s in the big cap-growth ETFs. It’s on every growth manager’s list. The buyback is a strong bid under the stock, but it doesn’t cancel factor rotations.

If the market decides it only wants 8× earnings and hard value, Uber bleeds with the rest of its bucket.

Long-Term Return Math

Strip out the noise and you’re left with this:

• Trailing FCF is about $9B.
• The market is valuing that at roughly the high-$100 billions.

That’s a ~5% FCF yield on a business that just doubled FCF in a year and still has room to grow.

If FCF per share grows 10–12% a year over the next five years and the market is willing to keep paying around 20× FCF for a scaled, asset-light platform with visible buybacks and a clean balance sheet, you’re looking at high single- to low double-digit annual returns.

No heroics. Just a real business compounding off a real cash base.

If labor law turns and the model gets forced into an employer structure, the yield needs to be higher, the multiple comes down, and your return math changes quickly.

That’s the trade-off.

What Would Change My Mind

I’d lean more bullish if:

• FCF per share compounding 15%+ for a few years is backed by discipline on leverage.
• AV moves from slideware to a line item with real contribution, without trashing capex.

I’d get much more cautious if:

• A big jurisdiction sets a clear employee-status precedent that obviously scales elsewhere.
• FCF flatlines for a couple of years while spend on AV and freight climbs.

When the model stops compounding, I stop pretending it’s a compounding story.

Kill Switch

My line is simple:

• If net leverage pushes and stays above ~2× EBITDA and FCF growth drops under 10% for a couple of years, I’m out.
• Or if drivers are broadly reclassified as employees in a way that clearly extends beyond one market.

No debating it. Uber’s edge is being a scaled, asset-light marketplace. If it becomes a capital-heavy, legally constrained employer, I’m not going to argue the stock back up on nostalgia.

Final Take: Who This Is For

If you want growing free cash flow, can live with one big binary risk (labor law), and don’t need a dividend to sleep at night, Uber makes sense here.

The cash engine is real.
Management finally acts like owners.
The robot story is extra, not required.

If you want clean income and hate legal overhangs, skip it. There are easier ways to make 8–10% a year.

My stance (for my own portfolio):
Buy candidate, sized as a core position, as long as drivers remain contractors in most key markets and FCF keeps compounding.

If you want more deep dives built this way—cash flow first, expectations and flows second, hype last—

👉 Subscribe to Phaetrix Investing

Disclaimer: This content is for informational and educational purposes only and is not financial advice. Nothing here is a recommendation to buy or sell any security. I’m explaining how I analyze companies, not what you should do with your money.