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.

Hunter Walk has been making moves in the startup world for over a decade. As co-founder of Homebrew, he's backed companies like Plaid, ClassDojo, and Managed by Q. But here's the thing – studying Hunter Walk investments isn't just about name-dropping portfolio companies.

It's about understanding how a successful investor thinks, evaluates deals, and builds relationships with founders. And trust me, there's a lot we can learn from his approach.

Who is Hunter Walk, anyway?

Before we dive into his investment philosophy, let's get the basics down. Hunter co-founded Homebrew in 2013 with Satya Patel. Before that, he spent time at YouTube (as Director of Product Management) and Google.

But here's what makes Hunter interesting: he's not your typical Sand Hill Road VC. Homebrew focuses on pre-seed and seed-stage companies, writing checks between $500k and $1.5m. They're looking for companies at the intersection of "bottom up" adoption and "top down" sales – basically, products that people love to use but enterprises are willing to pay for.

Sound familiar? Yeah, it should. This is the sweet spot where a lot of successful companies live.

What's Hunter Walk's investment thesis?

Hunter has been pretty transparent about Homebrew's investment approach on his blog. They focus on three main areas:

1. The "New Work" theme: This covers how people work, learn, and organize. Think tools for remote teams, education platforms, or productivity software that actually makes people more productive (not just busier).

2. Consumer experiences that monetize through B2B: These are products that consumers love but make money from businesses. Slack is the classic example – people loved using it, but the real revenue came from enterprise contracts.

3. Infrastructure for the next generation of apps: The boring stuff that makes the cool stuff possible. APIs, developer tools, data infrastructure – the picks and shovels of the modern startup ecosystem.

But here's where it gets interesting. Hunter doesn't just invest in themes. He invests in people. And his approach to evaluating founders is something every early-stage investor should pay attention to.

How does Hunter evaluate deals?

I've been tracking Hunter Walk investments for a while now, and there are some clear patterns in how he approaches deal evaluation.

He looks for missionary founders, not mercenaries: Hunter has said this explicitly on X: he wants founders who are obsessed with the problem they're solving, not just building a company to flip it. These are founders who will stick with the company through the inevitable ups and downs of startup life.

This is huge. As early-stage investors, we're basically betting on founders to execute for 7-10 years. If they're not genuinely passionate about the problem, they'll burn out when things get tough.

He values product intuition over everything else: Hunter came from a product background, so this makes sense. But he's not just looking for founders who can build good products – he's looking for founders who understand what makes products sticky and valuable.

This means founders who think about user experience, retention metrics, and product-market fit from day one. Not founders who think they can figure out the product stuff later.

He's obsessed with go-to-market strategy: Here's something that separates Hunter from a lot of other VCs: he really cares about how companies are going to acquire customers. Not just the initial few customers, but how they're going to scale customer acquisition profitably.

This is where his "bottom up adoption, top down sales" thesis comes in. He wants to see products that can spread organically but also have a clear path to monetization.

What can we learn from Homebrew's portfolio companies?

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

Plaid: This was a perfect Homebrew investment. Developers loved using Plaid's APIs to connect bank accounts to their apps. But the real money came from fintech companies paying for enterprise-level access and support.

Bottom up adoption (developers), top down sales (fintech companies). Exactly what Hunter looks for.

ClassDojo: On the surface, this looks like an education company. But dig deeper and you see the Homebrew thesis at work. Teachers and students loved using ClassDojo. But the monetization came from school districts paying for premium features.

Again – consumer love, enterprise monetization.

Managed by Q: This one's interesting because it eventually shut down. But you can see why Hunter invested. Office managers loved the platform for booking services. The monetization came from facilities management companies.

The fact that it didn't work out doesn't mean it was a bad investment thesis. Sometimes great ideas just don't execute well enough to survive.

What should early-stage investors learn from Hunter's approach?

Studying Hunter Walk investments has taught me a few things that apply to all early-stage investing:

1. Have a clear thesis: Hunter doesn't just invest in "good companies." He has a specific point of view about where the world is going and what types of companies will succeed. This helps him say no to deals that don't fit, even if they look promising.

For us angel investors, this means developing our own investment thesis. Maybe it's vertical SaaS for specific industries. Maybe it's tools for remote work. Maybe it's infrastructure for crypto applications. The point is to have a framework for making decisions.

2. Focus on the founder-market fit: Hunter consistently invests in founders who have deep expertise in the markets they're targeting. Not just general startup experience, but specific knowledge about the problem they're solving.

This is something we can evaluate as early-stage investors. Does this founder really understand their customers? Have they experienced the problem themselves? Do they have unique insights about the market?

3. Think about monetization from day one: Too many early-stage investors get caught up in growth metrics and forget to ask how the company will actually make money. Hunter's focus on companies that can monetize through B2B sales is smart because B2B customers generally pay more and have higher retention than consumers.

When we're evaluating deals, we should be asking: "How will this company make money? And how will they make more money over time?"

What about Hunter's contrarian bets?

Not all Hunter Walk investments fit neatly into the Homebrew thesis. And that's actually instructive too.

Hunter has made investments in companies like Cruise (autonomous vehicles) and Boom Technology (supersonic flights). These don't fit the "bottom up adoption, top down sales" model at all.

But they do fit another part of Hunter's approach: investing in founders who are tackling really hard problems with unique insights.

This is a good reminder that even with a clear investment thesis, there's room for contrarian bets on exceptional founders.

What's the bottom line for angel investors?

Hunter Walk's approach to investing isn't revolutionary. But it's disciplined, thoughtful, and grounded in real experience building products and companies. If you're looking to connect with other early-stage investors who share this philosophy of being genuinely helpful to founders, Angel Squad brings together operators-turned-angels who are focused on building real relationships with the companies they back.

The key takeaways for early-stage investors:

• Develop a clear investment thesis and stick to it
• Focus on founder-market fit, not just general founder quality
• Understand how the company will make money and scale revenue
• Look for products that users love but enterprises will pay for
• Don't be afraid to make contrarian bets on exceptional founders

Most importantly, Hunter's success comes from being genuinely helpful to founders. He doesn't just write checks – he helps companies think through product strategy, go-to-market approaches, and hiring decisions.

That's the real lesson here. Whether you're writing $500k checks like Homebrew or $25k checks as an angel investor, the companies that succeed are the ones where investors add real value beyond just capital.

And that's something every investor can learn from Hunter Walk's approach.