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 tracking Cyan Banister investments for years now, and honestly, her approach to early-stage investing is refreshingly different from the typical Sand Hill Road playbook. As someone who's spent years in the trenches of startup investing at Hustle Fund, I find her strategy both instructive and, frankly, a bit humbling.

Who is Cyan Banister?

Cyan is a partner at Founders Fund, where she's been backing companies since 2012. But here's what makes her story interesting: she wasn't born into Silicon Valley privilege. She started as an angel investor after founding and selling her own company, IronPort (which eventually sold to Cisco for $830 million).

Her early investments? Companies like Uber, SpaceX, Postmates, and Affirm. Yeah, not a bad track record for someone who started angel investing with her own money.

But what really sets Cyan apart isn't just her portfolio returns. It's her approach to finding founders and evaluating opportunities that most other investors pass on.

What Cyan Looks for in Founders

I've read dozens of interviews with Cyan, and a few patterns emerge in what she values:

Grit over pedigree: Cyan herself didn't come from privilege, so she recognizes resilience when she sees it. She's looking for founders who've overcome real obstacles and have something to prove.

Unique market insights: She wants founders who see opportunities that others miss. Not because they're smarter, but because they have different life experiences that give them unique perspectives on problems.

Ability to build movements: Many of Cyan's investments are in companies that don't just have customers. They have communities. Think about Uber's early drivers, SpaceX's space enthusiasts, or Affirm's mission-driven approach to consumer finance.

This is something we think about at Hustle Fund too. The best early-stage companies aren't just building products. They're building movements around ideas that resonate with specific communities.

The "Invest in What Others Miss" Strategy

Here's where it gets tactical. Looking at Cyan Banister investments over the years, there's a clear pattern: she's willing to back companies in spaces that other investors think are either too hard or too unsexy.

SpaceX (when she invested): Most investors thought private space exploration was crazy. Too capital intensive, too much regulatory risk, too long to exit. Cyan saw something different.

Affirm: When most fintech investors were focused on payments or lending platforms, Cyan backed Max Levchin's vision for transparent consumer finance. The thesis? People are tired of credit card tricks and hidden fees.

Postmates: Before on-demand delivery was proven, Cyan bet on the idea that people would pay for convenience. This was 2011, remember. Uber was barely a thing.

The lesson here isn't that you should invest in space companies or delivery apps. The lesson is that Cyan is willing to have conviction in ideas that seem obvious to her, even when they seem crazy to everyone else.

That's actually really hard to do. As early-stage investors, we're constantly battling FOMO and consensus thinking. It's easy to invest in the hot AI company that every other VC is chasing. It's much harder to write a check for something that feels contrarian.

How Cyan Adds Value Beyond Capital

Here's something that doesn't get talked about enough: Cyan's value-add to founders isn't about making fancy introductions or sitting in board meetings.

From what I've gathered, she's genuinely helpful in a few specific ways:

1. Product thinking: She came from building products herself, so she can have meaningful conversations with founders about user experience, pricing strategy, and feature prioritization.
2. Founder mental health: Cyan has been open about her own struggles and challenges. She's someone founders can talk to when things aren't going well. And trust me, things don't go well a lot in startups.
3. Long-term thinking: She's not pushing founders to optimize for the next fundraise. She's pushing them to build real businesses that can stand the test of time.

This is something every early-stage investor should think about. What's your actual value-add to founders? If it's just capital and introductions, you're not differentiated. Find the unique ways you can actually be helpful based on your own experience.

The Anti-Consensus Approach to Portfolio Construction

One thing that's interesting about Cyan Banister investments is that she's not spray-and-pray investing. She writes bigger checks into fewer companies than typical angel investors.

Her approach seems to be: have high conviction, write meaningful checks, and actually be involved with helping the companies succeed.

This is different from the typical angel investor playbook of writing small checks into 50+ companies and hoping a few work out. Cyan's approach requires more work per investment, but it also means she can actually add value to each company.

For angels and small fund managers, there's a real question here: do you want to be a passive investor in 100 companies, or an active investor in 20?

There's no wrong answer, but you should be intentional about it. At Hustle Fund, we write a lot of checks, but we also have specific ways we add value to every portfolio company through our Redwood School program and our community of founders.

What Early-Stage Investors Can Learn From Cyan

Okay, let's get practical. What can we actually take away from studying Cyan Banister investments?

1. Develop anti-consensus conviction: Don't just invest in what everyone else thinks is hot. Find opportunities that seem obvious to you but crazy to others. That's where the real alpha is.

2. Look beyond traditional signals: Pedigree matters, but it's not everything. Some of the best founders are the ones who don't fit the typical mold. Be willing to back founders who others might pass on.

3. Write bigger checks into fewer companies: If you're going to be a value-add investor, you need meaningful ownership to make it worth the time. Don't spread yourself too thin.

4. Find your unique value-add: What can you help founders with that other investors can't? For Cyan, it's product thinking and founder support. For you, it might be something completely different based on your background.

5. Be patient: Many of Cyan's best investments took years to pay off. SpaceX, Uber, Affirm – these weren't quick flips. If you're investing in transformational companies, you need to be in it for the long haul.

The Bottom Line

Cyan Banister's investment approach isn't something you can copy exactly. She has unique advantages based on her network, experience, and position at Founders Fund.

But the principles behind her strategy are applicable to any early-stage investor: have conviction in contrarian ideas, look for founders others miss, and actually add value beyond capital.

The venture world is increasingly competitive, with more investors chasing the same "obvious" deals. The investors who will succeed are the ones who can see opportunities that others miss and have the conviction to back founders who don't fit traditional patterns. If you're serious about learning from successful investors like Cyan and want to practice these principles with real capital at stake, Angel Squad gives you the opportunity to invest alongside Hustle Fund in early-stage companies while learning from a community of operators-turned-investors who are all figuring this out together.

That's what Cyan's been doing for over a decade. And that's what we should all be aspiring to do.