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.

Paul Buchheit created Gmail. He also came up with Google's "Don't Be Evil" motto. But what most early-stage investors should care about is this: he's one of the most successful angel investors of the last decade, backing companies like Airbnb, Stripe, and Reddit before anyone knew what they'd become.

Studying Paul Buchheit investments isn't about hero worship. It's about understanding how someone who built breakthrough products evaluates early-stage companies. And trust me, there's a method here that's worth unpacking.

Who is Paul Buchheit?

Before we dig into his investment approach, let's get the basics straight. Buchheit joined Google as employee #23 in 1999. He built Gmail, which fundamentally changed how we use email. He also created the first prototype of AdSense, which became Google's main revenue driver.

After Google, he joined Y Combinator as a partner, where he started angel investing seriously. In 2010, he left YC to focus on his own investments and eventually cofounded Y Combinator Continuity Fund. Now he invests through his own fund and has one of the most impressive early-stage track records in Silicon Valley.

His portfolio reads like a who's who of successful startups: Airbnb, Stripe, Reddit, Dropbox, Twitch (sold to Amazon for $970 million), and dozens of others. But the interesting part isn't the names. It's why he picked them when they were nothing.

The Core Pattern in Paul Buchheit Investments

Looking at Buchheit's investments over the years, some clear patterns emerge. He's not spray-and-pray investing. He's got a specific lens for evaluating companies.

He looks for products that feel like magic. Buchheit has said this explicitly in interviews. He wants products that make users say "wow, this is amazing" the first time they use it. Gmail felt like magic when it launched. Infinite storage (or what felt like it) when everyone else gave you 2MB. Conversation threading. Fast search. It was fundamentally different.

This shows up in his investments. Airbnb felt like magic because you could stay in someone's home for cheap. Stripe felt like magic because you could accept payments with seven lines of code instead of months of enterprise integration.

For early-stage investors, this is a useful filter. Does the product make you go "wow" when you first see it? Or is it just incrementally better than what exists?

He backs founders who obsess over details. Buchheit came from Google's product culture, where details mattered intensely. He looks for founders who have that same obsession. Not just vision, but execution on the small stuff that makes products feel polished.

This is something you can evaluate in a pitch meeting. Does the founder talk about specific user feedback? Do they obsess over conversion rates or user retention? Or do they just talk in big vague terms about changing the world?

He invests in platforms, not features. Gmail wasn't just an email client. It was a platform that other services could build on. Same with Stripe (payments platform), Twitch (streaming platform), and Airbnb (hospitality platform).

Buchheit seems to prefer companies that could become foundational infrastructure rather than point solutions. This makes sense. Platforms have more defensibility, higher margins, and bigger outcomes.

What Paul Buchheit Looks for in Founders

Beyond product, Buchheit has some clear preferences when it comes to founders:

Technical Depth

Buchheit is an engineer, and it shows in his investments. He backs technical founders who can actually build the product themselves. He's less interested in "idea people" who need to hire a team to execute.

This doesn't mean every founder needs to be a coder. But they need to deeply understand the technical challenges they're solving. When Buchheit invested in Stripe, the Collison brothers weren't just business guys with an idea. They were building the payment infrastructure themselves.

For early-stage investors, this matters. Technical founders can iterate faster, make better product decisions, and are less likely to get stuck when hitting technical roadblocks.

Speed of Execution

Buchheit values speed. He's said that one of the things that impressed him about Airbnb was how quickly the founders iterated. They'd launch features, get feedback, and ship improvements within days.

This is something you can evaluate. Look at a founder's track record. Do they ship quickly? Or do they talk about what they're going to build without actually building it?

Willingness to Do Things That Don't Scale

This is classic YC advice, but Buchheit really believes it. The Airbnb founders went door to door taking professional photos of listings. The Stripe founders personally integrated their API for early customers. These aren't scalable activities, but they're essential for learning what users actually need.

When you're evaluating deals, ask founders what they're doing that doesn't scale. If they don't have a good answer, that's a yellow flag.

The Airbnb Investment: A Case Study

Let's dig into one specific Paul Buchheit investment: Airbnb. This is probably his most famous win, and it's instructive.

Buchheit invested in Airbnb in 2009 when they were part of YC. At the time, the idea sounded crazy. Let strangers sleep in your house? Most investors thought it would never work. The market seemed too small (who actually wants to do this?), and the trust issues seemed insurmountable.

But Buchheit saw something others didn't. The founders were relentless. They'd flown to New York to personally photograph listings. They were getting real users and real revenue, even if it was small. And the product felt magical when you used it. You could stay in someone's beautiful apartment in Paris for a fraction of hotel costs.

This is the pattern: magical product, relentless founders, early traction even if small. Buchheit bet on those signals when others saw only risks.

For early-stage investors, this is the playbook. Don't get hung up on the reasons something won't work. Focus on the signals that it might work. Is the product magical? Are the founders executing relentlessly? Is there any traction at all?

Paul Buchheit's Contrarian Views

Buchheit has some views that go against conventional VC wisdom:

He doesn't care about market size as much as most VCs. He's said that he invested in Airbnb when the "market" seemed tiny. Same with Stripe. He's more interested in whether a product is magical and whether founders can execute than whether there's a giant obvious market.

This makes sense. The biggest outcomes often come from markets that don't look big at first. Facebook was "just for college students" when it started. Airbnb was "just for conferences" at first. The market expands as the product gets better.

He's skeptical of "market research" and focus groups. Buchheit believes in building products, shipping them, and seeing what users do. Not asking users what they want. Gmail wasn't built based on focus groups. It was built based on what the team knew email should be.

For early-stage investors, this means being skeptical of founders who spend too much time doing research and not enough time building and shipping.

He thinks most startup advice is wrong. Buchheit has written that following conventional wisdom is a good way to build a mediocre company. The best companies do things that seem crazy at first. Airbnb. Stripe. Gmail itself seemed unnecessary when it launched because everyone already had email.

What Makes Paul Buchheit Different From Other Angels

Here's what separates Buchheit from most angel investors:

He has genuine product taste. Because he built Gmail, he understands what makes products work at a gut level. He can see a early prototype and identify whether it has "it" or not. Most investors don't have this. They rely on metrics and traction because they can't evaluate product quality directly.

He's willing to be contrarian. Buchheit will invest in ideas that seem bad to other investors if he believes in the founders and product. This is rare. Most angels follow the herd because it's safer for their reputation.

He actually helps portfolio companies. Buchheit doesn't just write checks. He helps with product strategy, hiring, and thinking through hard problems. His portfolio founders consistently say he's one of the most helpful investors they have.

The "Don't Be Evil" Philosophy Applied to Investing

Buchheit created Google's famous motto, and it influences how he invests. He's backed companies that are trying to make things better, not just extract value. Stripe makes payments easier. Airbnb makes travel more accessible. These aren't zero-sum businesses.

For early-stage investors, this is worth considering. Are you backing companies that create genuine value? Or are you just betting on companies that can extract rent from existing systems?

The best outcomes often come from companies that genuinely improve things for users. Users stick around, retention is high, and word-of-mouth is strong.

Tactical Takeaways from Paul Buchheit Investments

Here's what you can actually apply to your own angel investing:

1. The "magic" test matters more than you think

Don't just evaluate whether a product is good. Evaluate whether it's magical. Does it make users go "wow"? If not, it's going to be hard to grow through word-of-mouth.

2. Back technical founders who can ship

Ideas are cheap. Execution is everything. Technical founders who can build and ship quickly have a massive advantage. Prioritize them.

3. Look for early traction, even if it's tiny

Buchheit invested in Airbnb when their revenue was tiny. But it was real revenue from real users. That signal matters more than TAM slides and projections.

4. Be willing to look stupid

The best returns come from investments that seem crazy at first. If everyone agrees something is a good idea, you're probably too late. Be willing to invest in things that make other investors skeptical.

5. Platform > feature

Companies that could become platforms are worth more than companies that are just features. Ask yourself: could this become foundational infrastructure that other companies build on?

6. Speed of iteration matters

How fast does the team ship? How quickly do they incorporate feedback? This is a leading indicator of success. Fast teams learn faster and have more at-bats.

Where Buchheit Focuses Now

Buchheit is still actively investing, though more selectively. Recent areas of focus include:

Developer tools and infrastructure. He understands this space deeply from his Gmail/AdSense days and continues to back companies building foundational tools.

Products that feel like magic. This hasn't changed. He's still looking for products that make users go "wow" on first use.

Technical founders solving hard problems. The pattern holds. He wants builders, not talkers.

The Bottom Line for Angel Investors

Paul Buchheit investments teach us that the best early-stage investing comes from genuine product taste, willingness to be contrarian, and backing founders who ship relentlessly. The magic product test, technical founder preference, and platform-over-feature thinking are all applicable whether you're writing $50k or $500k checks.

If you're looking to connect with other early-stage investors who think deeply about product and execution, Angel Squad brings together operators-turned-angels who share this philosophy. We focus on backing exceptional founders at the earliest stages, where product intuition and execution matter most. Check us out if you want to invest alongside people who care about building real businesses, not just chasing hype.

Key lessons from studying Buchheit:

• Magic product test: does it make users say "wow"?
• Back technical founders who ship quickly
• Look for early traction, even if tiny
• Be contrarian and willing to look stupid
• Platforms beat features for long-term value
• Speed of iteration predicts success

Buchheit's success isn't about being the smartest investor. It's about having genuine product taste, backing relentless founders, and being willing to invest in ideas that seem crazy to everyone else. That's something every early-stage investor can learn from.