Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups.

Travis Kalanick is one of the most fascinating figures in tech. But here's what matters for early-stage investors: after Uber, he didn't retire to a beach somewhere. He went all-in on CloudKitchens, a ghost kitchen real estate play that's now valued at $15 billion.

And honestly? There's a lot to unpack about his investment approach.

I've been studying Travis Kalanick investments to understand what drives his thinking. Not because I want to copy his strategy (most of us don't have billions to deploy), but because his bets reveal patterns about how operators think about infrastructure plays.

Who is Travis Kalanick now?

Everyone knows the Uber story. Travis co-founded the company, grew it to a $70 billion valuation, and then got pushed out in 2017. What happened next is more interesting for investors.

He started buying real estate. Lots of it. Properties that could be converted into commercial kitchens for delivery-only restaurants. This became CloudKitchens (also called City Storage Systems).

But he didn't stop there. He's made a handful of other investments through his fund, 10100 (pronounced "ten one hundred"). The portfolio is small but focused. Real estate technology, logistics, and what he calls "real world" businesses.

The CloudKitchens thesis: infrastructure for the gig economy

Let's start with the big one. CloudKitchens is not a restaurant company. It's a real estate company that rents kitchen space to restaurants that only do delivery.

The thesis is pretty straightforward: delivery is growing, restaurant margins are terrible, and real estate costs are one of the biggest expenses. If you can provide cheaper kitchen space without the front-of-house costs, restaurants can be more profitable.

Here's why this matters for early-stage investors. Travis saw a massive shift happening (delivery becoming a bigger part of food consumption) and asked: "What infrastructure will this new world need?"

Not "What's a cool app we can build?" but "What boring infrastructure will power this transformation?"

That's a different way of thinking about opportunities. Most consumer investors were backing meal kit companies or restaurant discovery apps. Travis was buying warehouses.

The pattern in Travis Kalanick investments: control the real assets

Looking at his portfolio, there's a clear theme. He's investing in companies that own or control physical assets.

CloudKitchens owns real estate. City Storage Systems (the parent company) is acquiring properties across multiple cities. These aren't SaaS businesses with 90% gross margins. These are capital-intensive businesses with real assets on the balance sheet.

Why does this matter? Because once you control the physical infrastructure, you have pricing power. You're not just a software layer that can be replaced. You own something tangible that's hard to replicate.

This is actually a contrarian bet in venture capital. Most VCs love asset-light businesses. Software companies that can scale without buying physical stuff. Travis is doing the opposite.

What makes CloudKitchens different from WeWork

Here's where it gets interesting. CloudKitchens looks a lot like WeWork on the surface. Both companies lease real estate, renovate it, and sublease it to businesses.

But there are important differences:

1. The unit economics are better: Restaurant operators need commercial kitchens. They can't just work from home or rent a coffee shop for the day. The demand is more stable.

2. Less emphasis on "community": WeWork spent millions on amenities, events, and building a brand. CloudKitchens is focused on providing functional kitchen space. Less overhead, better margins.

3. Multiple revenue streams: CloudKitchens doesn't just rent space. They also provide software for managing orders, data on what menu items sell best, and even financing for kitchen equipment.

The lesson here? If you're going to invest in real estate tech, make sure the unit economics actually work. And look for businesses that can generate revenue beyond just rent.

The "boring infrastructure" investment thesis

Travis has said that he's interested in "real world" businesses. Not just apps and software, but companies that move physical things around.

This is reflected in some of his other investments. He's backed companies in logistics, warehouse automation, and fulfillment. All businesses that touch the physical world.

Why is this interesting? Because most venture investors are still focused on software. There's less competition for deals in physical infrastructure. And if you can find the right opportunities, the moats are deeper.

For early-stage investors, this suggests looking at the infrastructure that powers new consumer behaviors. If everyone's using food delivery apps, who's providing the kitchens? If everyone's shopping online, who's building the fulfillment centers? If everyone's working remotely, who's providing the home office furniture?

Don't just invest in the app layer. Look one level deeper.

What Travis looks for in opportunities

Based on his investments and public statements, here's what seems to matter to him:

Massive markets with broken unit economics: Food delivery is huge, but most restaurants lose money on delivery orders. That's a problem worth solving.

Opportunities to vertically integrate: CloudKitchens doesn't just rent space. They provide software, data, equipment financing. The more of the value chain you control, the more money you capture.

Businesses that benefit from scale: The more properties CloudKitchens owns, the better deals they can negotiate with suppliers, the more data they collect, the more they can invest in technology. Scale creates compounding advantages.

Willingness to be contrarian: Travis is comfortable being in businesses that other VCs think are too capital-intensive or too boring. That creates opportunities.

The risks in Travis Kalanick investments

Let's be honest. This strategy has serious risks.

1. Capital intensity: CloudKitchens requires billions in real estate acquisitions. If the business model doesn't work, you can't just pivot to something else. You're stuck with a bunch of warehouses.

2. Regulatory risk: Cities can change zoning laws, health codes, delivery regulations. Any of these could hurt the business.

3. Execution complexity: Running real estate across dozens of cities is hard. You need local teams, local knowledge, local relationships. It doesn't scale as easily as software.

4. Reputation risk: Travis brings baggage from Uber. Some landlords, regulators, and potential partners are wary of working with him.

For early-stage investors, this is a reminder that not every big swing makes sense at the angel level. Capital-intensive businesses might work for billionaires, but they're risky for smaller investors.

What early-stage investors can learn from Travis's approach

Here's what I think is actually applicable to angel investing:

1. Look for infrastructure plays: When you see consumer behavior changing, ask what infrastructure will be needed to support that change. That's often a better investment than the consumer-facing apps.

2. Focus on unit economics from day one: Travis is obsessed with whether each kitchen location is profitable. Not "can we raise more venture funding?" but "does each unit make money?" Apply this to every deal you evaluate.

3. Vertical integration can create defensibility: Companies that control multiple parts of the value chain are harder to disrupt. Look for startups that aren't just adding a software layer, but actually own critical pieces of infrastructure.

4. Be willing to invest in "boring" businesses: Not everything needs to be a sexy AI company. Sometimes the best returns come from businesses that solve unglamorous problems really well.

5. Think about second-order effects: Travis didn't just think "delivery is growing." He thought "if delivery grows, what else will need to exist?" That kind of second-order thinking reveals opportunities that others miss.

The bottom line for angel investors

Travis Kalanick investments represent a specific approach: go big on infrastructure plays that benefit from scale and vertical integration. This works when you have billions to deploy and a high risk tolerance.

For most angel investors, the lesson isn't "go buy warehouses." It's about the mental model. Look for infrastructure, focus on unit economics, and don't be afraid of businesses that seem boring if they solve real problems.

The key takeaways:

• Infrastructure businesses can have deeper moats than software
• Unit economics matter more than growth at all costs
• Vertical integration creates pricing power
• Scale advantages compound over time
• Being contrarian can reduce competition for deals

And if you're looking to connect with other early-stage investors who think about infrastructure and unit economics, communities like Angel Squad focus on the fundamentals that actually matter for startup success.

Travis's approach won't work for everyone. But understanding how successful operators think about market opportunities, unit economics, and competitive moats? That's valuable for any investor.