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.

Ron Conway has been called the "Godfather of Silicon Valley." And when you look at Ron Conway investments, you understand why. Google, Facebook, Twitter, Airbnb, Pinterest, Dropbox. The list goes on.

But here's what most people miss: Ron's success isn't just about picking winners. It's about building a systematic approach to early-stage investing that creates compound advantages over time.

And the best part? The core principles work whether you're writing $25k checks or $250k checks.

Who Is Ron Conway?

Ron started angel investing in the 1990s after selling his company Personal Training Systems. He founded Angel Investors in 1998, which eventually became SV Angel, one of the most influential early-stage investment firms in Silicon Valley.

What makes Ron different from other super angels is his volume and velocity. SV Angel has invested in over 700 companies. That's not a typo. Seven hundred.

Most angel investors struggle to do 10 deals per year. Ron has been doing 50+ deals per year for decades.

This volume-based approach reveals something important about how he thinks about early-stage investing.

The Core Philosophy Behind Ron Conway Investments

After studying his approach for years, several clear patterns emerge:

1. Invest in People, Then Help Them Win

Ron's most famous quote is: "I invest in people, not ideas." But what does that actually mean in practice?

It means Ron is betting on founders who can adapt, execute, and build teams. The initial idea matters less than the founder's ability to figure things out.

But here's the second part that people forget: Ron doesn't just invest and disappear. He actively helps founders succeed by making introductions, recruiting talent, and solving problems.

This is crucial. His network becomes a competitive advantage for every company he invests in.

2. Portfolio Construction Through Volume

Most VCs try to be highly selective. They see 1,000 companies and invest in 10.

Ron takes a different approach. He invests in way more companies but at smaller check sizes (typically $250k or less for many years, though SV Angel's checks have grown).

This strategy only works if you have systems for deal flow, evaluation, and portfolio support. But if you can make it work, the math is compelling.

In a portfolio of 50+ companies per fund, you only need one or two massive winners to return the entire fund. And the more shots on goal you take, the higher your chances of hitting a Google or Facebook.

3. Speed as a Competitive Advantage

Ron is famous for making investment decisions quickly. Sometimes within hours of meeting a founder.

This isn't reckless. It's strategic.

In competitive deals, founders often go with investors who can move fast and make decisions. By being the fastest, Ron gets access to deals that slower investors miss.

For angel investors, this is a crucial lesson. If you take three weeks to make a decision, the round might close without you. Develop your evaluation framework so you can move quickly on good opportunities.

Breaking Down Specific Ron Conway Investments

Let's look at actual investments and what they reveal:

Google (1999)

Ron invested in Google in 1999 during the company's first major funding round. At the time, there were dozens of search engines. Why would another one succeed?

But Ron saw something different. He saw two technical founders (Larry Page and Sergey Brin) who had built a demonstrably better search algorithm. And he saw that they were focused on user experience rather than just monetization.

This investment became one of the most successful in venture capital history. But the lesson isn't "find the next Google." The lesson is: when you see founders with technical advantages and user-first thinking, pay attention.

Facebook (2004)

Ron invested in Facebook in 2004 when it was still limited to college students. Most investors thought it was just another social network.

But Ron recognized several key signals:

Insane engagement: College students were spending hours per day on the platform.

Network effects: The product got better as more people joined.

Young founder with vision: Mark Zuckerberg was clearly building something bigger than a college directory.

Ron didn't just invest. He helped Facebook recruit talent, make strategic decisions, and navigate rapid growth.

This is the Ron Conway playbook: invest early, then help the company succeed through active support.

Twitter (2007)

Ron was one of Twitter's earliest investors, backing the company when it was still a side project at Odeo.

At the time, Twitter seemed like a toy. 140-character messages? Who cares?

But Ron saw the potential for real-time communication and information sharing. He saw that early users were obsessed with the product, even if they couldn't articulate why.

This investment highlights another aspect of Ron's approach: he's willing to invest in products that seem trivial on the surface but show signs of deep user engagement.

Airbnb (2009)

Ron invested in Airbnb when the company was struggling to gain traction. They'd launched multiple times. Revenue was minimal. Most investors passed.

But Ron saw founders who wouldn't quit. Brian Chesky, Joe Gebbia, and Nathan Blecharczyk had tried everything to make Airbnb work. They'd sold cereal boxes to fund the company. They'd personally photographed listings.

That level of determination mattered more than the current metrics.

This is a crucial insight: early-stage investing is about founder resilience as much as product-market fit.

What Should Early-Stage Investors Learn from Ron's Approach?

1. Build a Repeatable Evaluation Process

Ron can make investment decisions quickly because he has a clear framework for evaluating founders and companies.

For angel investors, this means developing your own checklist. What signals are you looking for? What questions do you always ask? What red flags make you pass immediately?

Some things Ron looks for:

• Founders who have deep domain expertise
• Products with early signs of user love
• Markets that could be enormous if the product works
• Founders who are coachable and willing to take advice
• Teams that can attract top talent

Your framework will be different. But having a framework means you can move faster and make more consistent decisions.

2. Your Network Is Your Competitive Advantage

Ron's superpower isn't just picking winners. It's helping them win through introductions, advice, and access.

As an early-stage investor, your network is one of the most valuable things you can offer founders. Not just for fundraising, but for hiring, partnerships, and strategic decisions.

Ask yourself: what unique value can I provide beyond capital?

Maybe you have deep expertise in a specific industry. Maybe you know great engineers or designers. Maybe you've built and sold companies before.

Whatever your advantage is, lean into it. And invest in companies where your network actually helps.

3. Volume Investing Can Work (If You Have Systems)

Ron's approach of investing in 50+ companies per year isn't for everyone. It requires deal flow, quick evaluation, and systems for portfolio support.

But the principle scales down. If you're writing $5k checks, you could potentially do 10-20 investments per year instead of 2-3.

More shots on goal means higher chances of hitting a winner. And in early-stage investing, you only need one big winner to make your returns.

The key is having systems so you're not overwhelmed. Templates for due diligence. Standard processes for evaluating founders. Clear criteria for passing quickly.

4. Speed Wins Deals

In competitive rounds, founders often go with investors who can move fast.

This doesn't mean you should skip due diligence. It means you should have a process that lets you do due diligence quickly.

Some ways to speed up your process:

• Have standard questions you always ask
• Request specific materials upfront (deck, financials, cap table)
• Set clear timelines with founders about when you'll make a decision
• Trust your gut on red flags instead of spending weeks investigating

The founders who close their rounds in two weeks aren't working with investors who take a month to decide.

The Ron Conway "Mafia" Effect

Here's something that doesn't get talked about enough: Ron's portfolio companies help each other succeed.

Founders in the SV Angel portfolio make introductions to each other. They share best practices. They recruit from each other's companies. They become customers of each other's products.

This network effect compounds over time. Every successful company in Ron's portfolio makes future investments more valuable because they can help the next generation of founders.

For angel investors, this suggests a strategy: invest in clusters of related companies where introductions and knowledge sharing create value.

If you invest in five fintech companies, they can learn from each other. If you invest in three healthcare startups, they can share regulatory insights.

Your portfolio becomes more valuable when the companies help each other succeed.

What About the Failures?

Let's be real. Ron has invested in 700+ companies. A lot of them failed. Probably most of them.

But that's the point. His portfolio construction assumes that most investments won't return capital. He's betting that a few massive winners will more than make up for the losses.

This is crucial for angel investors to understand. If you're investing in early-stage companies, you need to be comfortable with a high failure rate.

The question isn't "will some of these companies fail?" The question is "will my winners be big enough to make up for my losses?"

The Tactical Takeaway for Angel Investors

Ron's approach boils down to a few core principles that work at any scale:

Develop a clear evaluation framework: Know what signals you're looking for so you can move fast.

Use your network as a competitive advantage: Invest where you can actually help beyond just capital.

Consider volume over concentration: More shots on goal can increase your odds of hitting a winner.

Move fast on good opportunities: In competitive deals, speed matters.

Help your portfolio companies succeed: Active support often makes the difference between success and failure.

Most importantly, Ron's success comes from having a systematic, repeatable approach. He's not guessing. He has a playbook that works.

And through Angel Squad, we're helping other early-stage investors develop their own systematic approaches while getting access to some of the best seed-stage deals we see.

The question isn't whether you can become the next Ron Conway. The question is: can you build a systematic approach that works for your investment strategy and network?