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.

Aaron Levie has spent nearly two decades building Box from a USC dorm room idea into a multi-billion dollar enterprise cloud company. But what most people don't know is that he's also been quietly making angel investments on the side. And his approach to investing is just as thoughtful as his approach to building products.

Here's what studying Aaron Levie investments can teach us about early-stage investing.

Who is Aaron Levie?

Aaron co-founded Box in 2005 when he was just 19 years old. The company went public in 2015 and now serves over 100,000 businesses with cloud content management. But Aaron isn't just a one-hit wonder who got lucky with Box.

He's been an active angel investor for years, writing checks into companies across enterprise software, developer tools, and infrastructure. And his investment approach reflects the hard-won lessons from building Box over nearly 20 years.

What Aaron looks for in investments

Based on his public statements and portfolio companies, Aaron's investment thesis centers on a few key themes:

Enterprise software that solves real problems: Aaron has said repeatedly that the best enterprise companies solve problems that customers will pay serious money to fix. Not nice-to-have features. Must-have solutions.

This makes sense. Box succeeded because enterprises desperately needed secure cloud storage and collaboration tools. Aaron looks for that same level of urgency in the problems his portfolio companies solve.

Developer-first go-to-market: Many Aaron Levie investments follow a bottom-up adoption model. Developers or individual users discover the product, love it, and then it spreads throughout the organization.

This was Box's playbook too. Individual users would sign up for free accounts, love the product, and eventually convince their IT departments to buy enterprise licenses.

Infrastructure for the next generation of apps: Aaron is bullish on the infrastructure layer. He's invested in companies building APIs, developer tools, and backend services that enable other companies to build better products.

This reflects his belief that the most valuable companies often build the picks and shovels that others depend on.

Breaking down Aaron's investment approach

Let's get tactical about how Aaron evaluates deals. Based on interviews and his public writing, here's what he cares about:

1. Product-market fit signals

Aaron came up building products, so he knows what real product-market fit looks like. He's not impressed by vanity metrics or hockey stick projections.

Instead, he looks for qualitative signals like:

• Are users genuinely excited about the product?
• Do they tell their friends about it unprompted?
• Would they be upset if the product disappeared tomorrow?

These are the same questions we should be asking when evaluating early-stage companies.

2. Understanding of enterprise buyers

Here's where Aaron's experience building Box gives him an edge. He knows that selling to enterprises is completely different from selling to consumers.

Enterprise sales requires understanding procurement processes, compliance requirements, and how buying decisions actually get made in large organizations. Aaron looks for founders who get this, even at the early stage.

3. Technical depth

Aaron is a technical founder himself, and he looks for that same technical depth in the founders he backs. Not just the ability to code, but the ability to think through complex technical architectures and scaling challenges.

This matters because enterprise companies eventually need to handle massive scale, complex security requirements, and integration with legacy systems. Founders who can't think through these challenges will struggle later.

What we can learn from Aaron's portfolio

Let's look at some actual Aaron Levie investments and what they tell us about his approach:

Plaid: This is a classic Aaron investment. Plaid built infrastructure (APIs for connecting bank accounts) that other companies depend on. It started with developers who loved the product, then scaled to enterprise customers.

Bottom-up adoption. Infrastructure play. Enterprise monetization. Exactly what Aaron looks for.

Airtable: On the surface, Airtable looks like a consumer product. But dig deeper and you see the enterprise DNA. Companies use Airtable to build custom workflows and databases without needing engineers.

This fits Aaron's thesis of products that individuals love but enterprises will pay for.

Figma: Before Adobe acquired it for $20 billion, Figma was another bottom-up success story. Designers loved using it. Then design teams adopted it. Then entire companies standardized on it.

The pattern repeats: product that users love, enterprise monetization, infrastructure that others depend on.

What makes Aaron's investment style different

Here's what separates Aaron from other angel investors writing checks in Silicon Valley:

He's actually run an enterprise company at scale: Most angels have never dealt with enterprise sales cycles, procurement processes, or navigating compliance requirements. Aaron has lived this for nearly 20 years.

This gives him pattern recognition that most angels lack. He can spot founders who understand enterprise sales versus founders who are just guessing.

He focuses on long-term category creation: Aaron isn't looking for quick flips or companies riding short-term trends. He invests in founders building category-defining companies that will matter in 10+ years.

This long-term orientation comes from his experience building Box. He knows that great enterprise companies take time to build.

He values contrarian thinking: Aaron has said that Box succeeded partly because they made contrarian bets that others thought were crazy. He looks for that same contrarian thinking in founders he backs.

Not contrarian for the sake of being different. But contrarian based on unique insights about how the market will evolve.

Tactical takeaways for angel investors

Studying Aaron Levie investments reveals several principles we can apply to our own angel investing:

1. Invest in infrastructure and tools

Companies building infrastructure for other companies often have stronger economics than end-user applications. They have higher retention, better unit economics, and more defensible moats.

Look for companies building the tools and infrastructure that enable the next generation of applications.

2. Prioritize bottom-up adoption

Products that spread organically through organizations are way more capital-efficient than products requiring expensive top-down sales. And they often have stronger product-market fit.

When evaluating deals, ask: "Can this product spread virally within organizations?"

3. Understand enterprise buying patterns

If you're investing in B2B companies, you need to understand how enterprises actually buy software. Who are the decision makers? What's the approval process? How long do sales cycles take?

Founders who don't understand these dynamics will struggle to scale, even with great products.

4. Look for technical depth in founders

This doesn't mean every founder needs to be an engineer. But they need to understand the technical challenges they'll face as they scale.

Can they articulate their technical architecture? Do they understand their scaling bottlenecks? Can they recruit strong technical talent?

5. Think long-term

Aaron's best investments are in companies building for the long haul. These aren't companies trying to flip in 2-3 years. They're building category-defining businesses that will matter in a decade.

This requires patience. But it also leads to better outcomes.

What about Aaron's investment misses?

Not every Aaron Levie investment has been a home run. And that's instructive too.

The reality is that even the best investors get it wrong sometimes. What separates good investors from great ones isn't their hit rate. It's their ability to size positions appropriately and help their winners succeed.

Aaron has said that some of his best learning has come from investments that didn't work out. Understanding why companies fail is just as valuable as understanding why they succeed.

The bottom line for early-stage investors

Aaron Levie's investment approach isn't complicated. But it's disciplined and grounded in real operating experience.

He invests in infrastructure and tools that enable other companies. He looks for bottom-up adoption models with enterprise monetization. He values technical depth and long-term thinking. And he's patient enough to let great companies develop over time.

For angel investors who want to build meaningful portfolios, there's a lot to learn from how Aaron thinks about investing. The companies that win aren't necessarily the flashiest or fastest-growing. They're the ones solving real problems for customers who will pay to have those problems solved. If you're interested in learning more about early-stage investing alongside other operators who've made the leap to angel investing, that's exactly what we focus on at Angel Squad. We help people learn to evaluate deals, build portfolios, and connect with founders solving meaningful problems.

The key is developing your own pattern recognition, just like Aaron has. That comes from seeing lots of deals, making investments, learning from both successes and failures, and building genuine relationships with founders.

And that's something every investor can learn from Aaron's approach to backing the next generation of enterprise companies.