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.

I've been following Mario Gabriele's work for years. If you've spent any time in the startup world, you've probably read The Generalist at least once. But here's what most people miss: Mario isn't just a great writer about startups. He's also an active investor making thoughtful bets through his fund, Generalist Capital.

And honestly? Studying Mario Gabriele investments teaches you more about early-stage investing than most VC podcasts ever will.

Who is Mario Gabriele?

Mario started The Generalist in 2019 as a side project while working at a VC firm. What began as a newsletter turned into one of the most influential voices in tech. By 2021, he had over 75,000 subscribers hanging on his every word about startup strategy, market analysis, and emerging trends.

But Mario didn't just want to write about startups. He wanted to back them.

In 2022, he launched Generalist Capital to invest in early-stage companies. The fund focuses on pre-seed and seed rounds, typically writing checks between $100k and $500k. And because Mario built his reputation on deep research and thoughtful analysis, founders actually want him on their cap table.

Here's why that matters: Mario gets access to deals that other early-stage investors never see. Founders trust him because he's proven he can help them think through complex problems and tell their story effectively.

What makes Mario's investment approach different?

After analyzing dozens of Mario Gabriele investments, I've noticed some clear patterns in how he evaluates opportunities.

He invests where he has information advantages

Mario's newsletter gives him an unfair advantage. When he writes deep dives on industries like fintech infrastructure or creator economy tools, he's not just producing content. He's doing research that informs his investment decisions.

This is smart. Most early-stage investors are flying blind, making decisions based on 30-minute pitches and surface-level market research. Mario spends weeks talking to operators, analyzing competitive dynamics, and understanding where markets are heading.

For angel investors, the lesson is clear: develop expertise in specific areas. You don't need to write a popular newsletter, but you should know something about your target markets that other investors don't.

He looks for narrative-driven companies

Mario understands storytelling better than almost anyone in venture capital. And he consistently backs companies that can articulate a compelling narrative about why they exist and where they're going.

This isn't about flashy pitch decks. It's about founders who deeply understand their market and can explain their vision in a way that makes people want to join the mission.

When evaluating deals, Mario asks: Can this founder tell a story that resonates with customers, employees, and future investors? If not, the company will struggle to scale no matter how good the product is.

He focuses on infrastructure and tools

Look at the Mario Gabriele investments portfolio and you'll see a pattern. He tends to back companies building infrastructure for the next generation of startups, not consumer apps hoping to go viral.

Companies like Ramp (corporate cards and expense management), Vanta (security compliance), and Mercado Libre (Latin American e-commerce infrastructure) fit this thesis. These are businesses solving real problems for other businesses, with clear paths to revenue from day one.

This approach makes sense for early-stage investors. Consumer companies are lottery tickets. Infrastructure companies are often just solid businesses that compound over time.

Breaking down specific Mario Gabriele investments

Let's look at some actual investments and what they reveal about his strategy:

Ramp

Mario invested in Ramp early, recognizing that corporate card and expense management was ripe for disruption. The existing solutions (looking at you, Concur) were clunky and hated by users.

But more importantly, Ramp had a clear go-to-market advantage. They could acquire customers profitably because businesses actively search for better expense management solutions. No need for massive ad budgets or growth hacks.

This is classic infrastructure investing. Find a painful problem that businesses will pay to solve, back a team that can execute better than incumbents, and watch it compound.

Mutiny

This investment shows Mario's thesis around personalization and marketing technology. Mutiny helps B2B companies personalize their websites for different visitors, which sounds simple but is actually quite sophisticated.

What's interesting here is the timing. Mario invested when "personalization" was becoming table stakes for consumer companies but B2B companies were still struggling with basic website optimization. He saw the gap and bet on a team that could bridge it.

Mercury

Banking infrastructure for startups. Another perfect example of Mario backing the picks and shovels rather than the gold miners. Startups need bank accounts, and the traditional banking system treats them terribly.

Mercury solved this with better user experience, integrated financial tools, and a brand that actually resonated with founders. Classic product-market fit in an underserved market.

What should angel investors learn from Mario's approach?

After studying Mario Gabriele investments for months, here are the tactical takeaways I think matter most:

1. Build an information moat

You don't need a newsletter with 100,000 subscribers. But you do need some way to develop insights that other investors don't have.

Maybe you work in healthcare and understand the problems hospitals face. Maybe you spent years in e-commerce and know what merchants struggle with. Maybe you're deeply embedded in a specific geography or demographic.

The point is to have an unfair advantage in pattern recognition. When you see a pitch, you should be able to evaluate it based on real knowledge, not just gut feeling.

2. Invest in storytellers

Mario has said explicitly that he looks for founders who can craft compelling narratives. Not because storytelling is a nice-to-have skill, but because it's essential for recruiting, fundraising, and customer acquisition.

When you're evaluating deals, pay attention to how founders talk about their company. Do they ramble? Do they use jargon? Or do they paint a clear picture of the problem they're solving and why they're uniquely positioned to solve it?

The best founders make you feel like you're missing out if you don't invest. That's not manipulation. That's effective communication about something they genuinely believe in.

3. Focus on infrastructure over entertainment

Consumer apps are fun to use and exciting to talk about. But infrastructure companies are easier to evaluate and often generate better returns.

Why? Because infrastructure companies solve clear problems with measurable ROI. A company selling to businesses doesn't need to go viral. They just need to find customers who have the problem and can afford the solution.

This is especially relevant for angel investors with limited capital. You can't afford to make 50 lottery ticket bets hoping one hits. You need to make focused bets on companies that have plausible paths to becoming real businesses.

4. Think about second-order effects

One thing that separates Mario from other investors is his ability to think through second and third-order effects of trends. He doesn't just identify what's happening now. He thinks about what happens next and what opportunities emerge as a result.

For example, the shift to remote work isn't just about video conferencing tools. It's about new infrastructure for distributed teams, new financial products for global workers, new real estate models for flexible office space.

When you're evaluating deals, ask: What trends is this company riding? And what will need to exist for this company to succeed that doesn't exist yet?

5. Add value beyond capital

Mario gets deal access because founders know he'll help them tell their story and think through strategic challenges. He's not just a source of capital, he's a strategic advisor who brings unique skills to the table.

As an angel investor, you should ask yourself: What value do I bring beyond money? Maybe it's customer introductions. Maybe it's product feedback. Maybe it's helping with hiring.

If your only value is writing checks, you're going to struggle getting into the best deals. And honestly, you probably shouldn't be angel investing in the first place.

The bigger picture on Mario's investing philosophy

What makes Mario Gabriele investments interesting isn't just the specific companies he backs. It's the framework he uses to evaluate opportunities.

He's patient. He doesn't chase hype. He does deep research before making commitments. And he backs founders who are building real businesses, not just pitching compelling stories.

This approach won't generate the same Twitter buzz as backing the hot AI company everyone's fighting to get into. But it's a more sustainable strategy for building a portfolio that actually returns capital.

That's exactly why we built Angel Squad. We wanted to create a community where investors could learn these frameworks, get access to quality deal flow, and invest alongside experienced operators who are actually helpful to founders.

For those of us making our own early-stage investments, whether through angel syndicates or joining communities focused on backing emerging managers, Mario's approach offers a model worth studying. The key is developing genuine expertise, thinking critically about market opportunities, and building relationships with founders before everyone else recognizes how special they are.

That's the real lesson from studying Mario Gabriele investments. Success in early-stage investing isn't about being the loudest voice in the room or having the biggest Twitter following. It's about doing the work to understand markets deeply, recognizing exceptional founders early, and being genuinely helpful once you've invested.

And if you can write as well as Mario? That doesn't hurt either.