In the Asylum with Nick Chirls

A behind-the-scenes look into what it takes to build a brand that stands out in venture

In venture capital, funds have historically traded creativity for institutional playbooks. But today, breaking the mold has become the new standard, and Asylum Ventures is leading that charge.

With the ethos that "founders are artists, not assets," Asylum is redefining venture capital by seeking the unconventional, the obsessed, and the bold, believing these founders are consequently the true drivers for unparalleled returns.

We spoke with Nick Chirls, Co-founder at Asylum Ventures, to understand why the world needs yet another venture fund and how Asylum has found its unique voice in a crowded venture landscape. Nick shares why timing is the key ingredient, how Asylum redefines founders as creatives in company building, and why standing for something is essential for a fund to stand out.

For those who don’t know Nick, he’s a New York tech scene OG, previously co-founding  Notation Capital and before that, Head of Investments at Betaworks.

Conversation Outline

1. Why the 2024 venture market is optimal for funds to do things differently

2. Why having a clear belief system sets a fund apart in today’s venture landscape. 

3. Why (and how) Asylum is redefining “founders as artists, not assets.”

Nick, congratulations on announcing the new fund! Excited to dive into Asylum. 

We’ve known each other for a long time and a lot has changed in startup land. What would you say are the biggest differences today in 2024 compared to when we met back in 2014?

Back then there was no playbook. It was a bunch of people on the fringes, sort of making it up as they went. And today it’s largely turned into this factory of playbooks, which is one of the reasons we started Asylum.

I don’t know if anyone else described it this way, but I often describe Betaworks in that era as a bunch of kids in their twenties making random things on the internet, which I think is accurate. There was no playbook, no top-down research—just a bunch of passionate, creative kids thinking up cool things to make.

I think that led to this wonderful, creative, underdog energy. A lot of what came out of that era worked, and the natural inclination for everyone, myself included, was to think, "How can we just rinse and repeat this indefinitely?" But I believe something got lost along the way.

When I think about many of the best founders ever—and even some of the more recent, inspiring ones—people like Brian Chesky at Airbnb, Brian Armstrong at Coinbase, Palmer Luckey at Anduril, and Melanie Perkins at Canva come to mind…they all existed on the fringe in their own way and did truly unique, deeply creative things in often strange or unconventional markets, whether that's crypto, defense, or, in Melanie's case, Canva. She famously pitched her idea to around 500+ people, and no one would give her funding.

There was a certain outsider mentality for all of them. I'm really inspired by companies and people who may glance at the playbooks but ultimately choose to do things their own way. Those are the kind of people I’m looking for and want to work with. I believe they still exist.

Tell me more about the “why now” for the new fund. 

These founders often resemble artists just as much as they do business executives. I believe those are the types of founders every investor should want to work with. But it's easy to take the path of least resistance and find founders who look like everyone else, doing things the same way, and trying to arbitrage some small advantage.

The whole industry—startups and venture—has become highly institutionalized. It's much more transactional than it used to be, far more competitive. And often, there’s a lot of short-term, arbitrage-focused thinking rather than a focus on finding founders with real courage, or startups having the courage to do it your own way and lean into your inner artist as much as your inner business executive.

I’ve said this before but I’ll say it again: Asylum could only exist now. If we had launched it 10 years ago, I don’t think it would have been relevant. What excites me about Asylum today is that, in many ways, it’s a reaction to what the industry has become. The beauty of an industry becoming institutionalized and cookie-cutter is that it creates an opportunity for people to do something different.

So, as much as I’m frustrated by the cookie-cutter institutionalization, I’m also grateful for it because it allows us to exist. 

Tell me more about the ethos behind Asylum. How do you see that ethos becoming a key differentiator for the fund in a crowded venture landscape?

I think the part we’ve figured out—and I suspect won’t change much—is that today, in venture, you actually need to believe in something. That wasn’t always the case. If you look at the history of venture capital, in the ’70s and ’80s, just having money was enough. There weren’t many venture firms, and it was a new form of investing. If you had capital, you were in a good spot.

By the dot-com era, things got crowded and bubbly, with countless new venture firms. Even then, in the early days, it was innovative to have funds dedicated solely to internet products. Then came a wave of funds focused on early software-as-a-service companies. So, in what I’d call the second phase, having a clear investment thesis became important.

In this last cycle, we’ve seen an explosion of venture firms—sector-specific, geo-focused, and large platforms, which we now refer to as the “big banks.” It’s become hyper-competitive, comparable to hedge funds, private equity, and other asset classes. In that environment, the only thing left to differentiate from a brand perspective is actually standing for something.

Standing for something can be scary for most VCs because it means you’re going to deter as many founders as you attract. By its very nature, standing for something means you can’t please everyone. Otherwise, you’re not really standing for anything. Most VCs are hesitant to do this because they want to see everything, afraid of narrowing their focus and missing out on opportunities.

But in a way, that makes it easier to stand out, even in such a hyper-competitive field. The good news for us—and maybe for other VCs that decide to take this route in the coming decade—is that there are only a handful, maybe five or ten firms, that truly stand for something.

I learned this firsthand with Notation, which was the first pre-seed firm back in 2015. That was a clear stand for a stage, but I saw that approach slowly get arbitraged away as the market caught up. The lesson I took from that is that standing for a stage, geo, or sector isn’t really standing for something—it’s just pursuing an arbitrage. However, if you can stand for something unique and authentic to you, it’s much harder for the market to arbitrage that away.

I think the best example in the market today is Founders Fund. They’re controversial because they stand for something, and whether you agree with them philosophically or not, they are clear about their stance. Whether I agree with their philosophy or not, I respect the courage it takes to stand for something so clearly and authentically. 

I think that’s the opportunity. When you look at most VC brands and websites, they all feel like the same thing. They all say they’re looking for “courageous, unique founders in huge markets,” etc. It’s the same language across the board. Sometimes I look at VC websites just to get inspiration for what not to do.

It’s always about “the world’s best founders building in the largest markets.” But what does the world’s best founders even mean? It’s all this bland, catch-all language that doesn’t really say anything.

I’d much rather, and this is true for startups as well, focus on a small subset of diehard customers who love your product. You shouldn’t aim to sell to everyone who might just like your product a little bit.

Can you walk me through Asylum’s point of view and what you stand for? What were some of the core beliefs that served as the foundation for everything you’ve built?

Our tagline is Founders are artists, not assets. If I had to summarize my core belief, it’s that the best founders, especially in the early days, look more like artists creating a fundamentally new, creative project. They don’t resemble business executives chasing an arbitrage opportunity.

Founders should be treated like artists—in the most heroic sense—not as just another line item on a balance sheet for some asset management firm. For me, this is personal. I’ve written about it before, but I felt like that line item when I worked at Lehman Brothers. In a way, I was saved by these creative, wonderful individuals—probably not even called founders back then—just unemployed people building things on the internet.

In the post-financial crisis era, I was deeply inspired by these people. At that time in my life, it felt like the universe was showing me a different path. I have a deep, deep empathy, love, and respect for what founders do—the risks they take and how much they put on the line. I believe they should be treated like heroic figures. Unfortunately, that’s not how most venture capitalists approach working with founders, and in many ways, I take personal offense to that.

The most successful VC firms in this past cycle have become large asset managers. They don’t look or feel all that different from a Lehman Brothers or a BlackRock. I believe they do a fundamental disservice to early-stage founders, and that really bothers me.

My mission is to provide an alternative to that.

You have this core belief—how did you take that belief and turn it into a name that encapsulates it? Can you walk me through your process of coming up with the name and how it reflects your philosophy?

Well, it was inspired by Asylum Records, David Geffen’s first record label. Geffen was a legendary music and movie producer, and I always loved the name of that label. I was deeply inspired by how he supported the artists and musicians he worked with—people like Joni Mitchell, the Eagles, and Bob Dylan.

He truly viewed them as heroic figures. He was so deeply intertwined in their lives, and he saw it as his responsibility to support not just their work but their lives. He focused on creating an environment where they could do their best work. He wasn’t making or producing the songs; he was building the space for those artists to thrive creatively.

Rick Rubin is another one of those figures I’ve always been inspired by, more contemporary but in the same spirit. And I just love the name Asylum. It doesn’t sound institutional, and it has this dual nature that really resonates with me. The literal meaning is a place of refuge and support, but people often associate it with an insane asylum. Let’s be honest—many of the best artists and founders are eccentric. I’ve always loved that duality.

It’s a highly memorable name and doesn’t sound like the forgettable names of many other venture firms. I fell in love with it immediately and kept it in the back of my mind for years. We actually got talked out of using it for about a year. The legal name of our fund is something very boring and placeholder-like.

But finally, like many things, in the last few months we just said, You know what? Fuck it. This was always the name. It’s our favorite, and we’re sticking with it. The name Asylum best represents what we’re trying to do, so we decided to take a risk and go for it. 

Walk me through the decision to make your website feel like a manifesto or a love letter to artists. You could have taken it in so many different directions, especially with a name like Asylum. 

Can you share the thought behind that choice? How did you and the team land on this approach, and what was the thinking process that led you there?

I don’t know if that will always be our website, and I suspect it won’t. But Asylum Ventures right now is really just that statement. We don’t have a portfolio yet. We’ve raised the fund, but we haven’t made any investments. We haven’t done anything yet. Now comes the hard part—actually going out, living up to, and executing these ideals.

At the moment, all we are is three people, an idea, and a mission. So, in many ways, the simplest and truest expression of that is the words on the page. It’s also nice to have everything live in one place, rather than creating a separate blog somewhere. It just felt right. Plus, it’s a good reminder for us. We don’t spend much time on our own website, but whenever we do, it’s a grounding experience. What started as an internal document now lives as an external one, and in a way, that holds us accountable in an important way.

For example, when we start making investments and put them on the site—which we will eventually—if they don’t align with those words, it will diminish the value and strength of what we stand for. So in a sense, those words hold us accountable to make decisions that truly represent what we believe, because they will live alongside those commitments.

As a former founder, one of the things I really loved about reading your manifesto was how you call out company building as a creative act. Can you elaborate on that? How do you think about building a company in ways that others in the ecosystem haven’t fully grasped?

Starting a company isn’t just a creative act—it’s often a deeply personal expression of the founder or group of founders. At the risk of sounding hyperbolic, I believe it’s quite brave and courageous to express yourself in such an honest way, whether it’s building a brand, creating a painting, or starting a company.

To the extent that a company is truly representative of the person behind it, I think the odds of success are much higher. Building something entirely new that no one has ever done before—that’s art, right? Great art isn’t derivative; it’s a fundamentally new idea or creative expression. I believe the parallel is almost one-to-one. If you’re doing something truly new, regardless of the medium, you’re making art.

I think when people hear the word art, they often associate it with art projects that aren’t commercial, big, or meaningful. I also happen to be a slightly obsessive, very early-stage art collector, and many fantastic artists are highly commercial. There's a common misperception that art and commerce can’t coexist. Many of the best artists my wife and I have become friends with over the years want to make great art, and they understand that to keep doing that, they need to be commercial in some way. 

I see a similar dynamic with startups. Often, it begins with wanting to solve a problem—whether it’s your own or someone else’s—and finding a creative, novel way to do it. To continue doing that for the long term, you need to build a commercial apparatus around it. And again, I think a lot of great artists are doing the same thing.

A lot of people don’t realize that many great artists are also managing large teams. Depending on the artist, once they reach a certain scale, they aren’t executing every stroke or handling every detail of their work themselves. They’re leading and managing teams of people. I’ve been trying to find holes in the comparison, but the overlap between art and building companies is significant.

Of course, there are obvious examples like Steve Jobs, who most people would see as a truly epic artist and designer. But it doesn't have to be limited to creative products. The parallels run deeper than that.

You don’t have to be making design software to be creating art, in my view. Take Elon building spaceships—that guy is definitely making art. Whether people like it or not, the Cybertruck, for example, is an art project in its own right. He made a bold, creative decision, and that's what art is about.

When you're meeting with founders, are there specific things that you look for? What's the difference when somebody's pitching who feels more like a traditional “executive” vs. an “artist”? How do you kind of parse between those two things?

I try not to put too much weight on resumes. I spent my first year out of college as a trader at Lehman Brothers, an investment bank. If I held that against myself or judged others solely by their past roles, I don’t think that’d be fair.

Especially for people early in their careers, who are trying different things and figuring out what suits them, it’s important to allow space for that exploration. It took me years to find my own path.

One of the things I love to do with almost every founder I meet is understand their story, their history, and what motivates them. I love hearing where people grew up and the important or formative experiences they remember from their childhood. I think it's crucial to understand what shapes someone and drives them—the "why" behind what they’re doing.

At Asylum, we've even played around with a tagline: Don't do this. The common wisdom in Silicon Valley is that everyone should do a startup, much like the earlier meme that everyone should learn to code. But we've been leaning into the idea of saying: Don't do a startup—definitely don't do that. Because for all the wonderful, joyful moments, it's also going to basically ruin your life—whether it goes well or not. If it does go well, good luck. You're in for a very difficult 10 or 15 years. That’s why it’s so important to understand the motivation behind why someone is doing this.

We look for obsession. We try to gauge if someone needs to do this. You can tell them as many times as you want not to, but they’re going to do it anyway. I’m looking for people who really care about the details—not just product or design details, but cultural ones, too. It’s about how they tell their story, how they message what they’re doing to customers, investors, and employees. I’m searching for people who are special communicators and leaders.

I'm also looking for markets and ideas that feel genuinely novel, not just derivatives of something else. If it's a decent, obvious idea, I assume there are 20 to 50 teams working on it already. We meet people so early that it's impossible to meet all of them and determine which one or two teams are the best. So, I’d much rather invest in products or markets that may seem overlooked today but could be really interesting in the future. There’s probably only one team working on them because the idea feels a little weird, fringe, or overlooked in some way.

And because the idea might be overlooked, it becomes easier to understand if the founder is truly obsessed with it. Most people would look at it and think, Why on earth would you be doing that? Why would you spend your life on this? The answer is usually that the founder is genuinely obsessed.

That doesn’t necessarily mean it's a good idea, but if someone is dedicating their time to a strange, niche area, it's often because of a deep, genuine obsession.

How much does a founder’s point of view and belief system factor into your investment decision? Do you prioritize founders or visions that stand for something, or is it more about the strength of the product or idea? How do you balance these elements when deciding to invest?

We actually used to ask a specific question on our Get in Touch page: What do you believe that others don’t? Or, What is it about this idea, project, or company that you believe in, but the rest of the market doesn’t yet? I think it’s a critically important question.

The way people answer this question tells you a lot—not just in the content of their response, but in the style. A simple, passionate response can be so powerful. I love a good revenge arc or knife fight mentality. When someone says, “This is the simple thing I believe in, and I don’t understand why others don’t get it yet. We’re going to go all in until they do,” that gets me fired up.

I love the us versus them mentality. I love working with people who are on a mission and ready to prove themselves. That’s why I think it’s such an important question. If what you're building is something that everyone already understands and agrees with, that’s often a problem.

We’re looking for people who have a specific belief about the future that others don’t yet understand. And it’s got to be simple. Simplicity is key. If it takes four paragraphs to explain, it’s too complicated. It should be something that can be captured in a sentence or two.

What do you hope founders will say about Asylum five to ten years from now?

This may sound a bit "squishy," and I hate saying that, but another major source of inspiration for me—and I’m sure for many others—has been A24. They’re a perfect comparison to venture because they were a response to the big Hollywood studios over the past decade. They provided an alternative for artists and creatives who didn’t want to feel like they were working with bankers at the major studios.

Their success has been phenomenal. I’ve obsessively read everything written about them, and I’m fortunate to have friends who work there. When you read interviews with artists about A24, a few things really stand out. One is their clear, well-defined, and distinct sense of taste. Another is their deep appreciation for the artist and the commitment to full creative control.

The comparison to venture is a bit different because we don’t have control to begin with, but there are ways VCs try to expand their influence. I believe the best companies are built by unique founders who have full control over how they build their company.

The last thing, and maybe the most interesting, is how many artists say that working with A24 just feels different. They’re not always great at describing it, but they insist that the experience is real. It’s everything—from the small interactions to how they meet, evaluate things, and collaborate.

In many ways, that’s my North Star: when you ask what it means to work with Asylum, a founder should be able to definitively say, “It just doesn’t feel like anything else in venture.” It’s kind of abstract, but it’s the sort of thing where you know it when you experience it.

About Nick Chirls

Nick has been building and investing in startups in NYC for the past 15 years. Previous to Asylum, Nick was the co-founder of Notation, a pre-seed firm dedicated to partnering with technical founders in the earliest stages of a company. Nick was named to the Midas Brink List in 2023.

You can find Nick on Twitter or LinkedIn.