About Asylum Ventures
Founded in 2024, Asylum Ventures is an inception-stage venture capital firm investing in artists, thinkers, and visionaries as they commit to one of the most challenging creative acts: building a company.
BRV Fund Manager Sarah Carr spoke with Mackenzie Regent, COO + Founding Partner at Asylum.
Sarah: Tell me about yourself and your path to VC.
Mackenzie: My path to venture was a bit wonky. It was not a career that I intentionally sought out. I started my career in Big Four accounting at PwC, which was a great place to begin my career. I learned the basics of client services, how to show up, and how to do the job. I’m a Type A person so I always thought that being in a structured environment would suit me.
When I reflected on the reality of my work, I felt like I could foresee what I would be doing every day until I retired. I didn’t want that. So, I did a total 180 and I started working at WeWork during its heyday. That was my first exposure to high velocity startup craziness.
If you’ve consumed any of the content about WeWork, a lot of it was quite accurate. I ended up getting laid off when things crashed and burned but, despite the insanity of the company at that time, I met some of the most dedicated, fun, smart people I had ever worked with. I wondered what it would look like to get closer to working with companies at an early stage.
Through a series of—perhaps—not very intentional events, I ended up meeting Nick Chirls, one of the founding partners at Notation Capital. He and his cofounding partner, Alex Lines, were looking for help with all things non-investment related. It was just the two of them, they had raised three funds, and Notation was one of the first pre-seed firms in New York City. I thought it sounded great. What better way to learn about how to run a venture firm? There certainly was no better way to learn the industry quickly and get work with companies at the very earliest stages across industries and sectors – so, I did it.
Sarah: What is the origin and ethos of Asylum?
Mackenzie: Notation Fund I was a $7M fund raised in 2015 when the concept of pre-seed was still quite new. It was unique and different to anchor a fund’s brand and identity on stage-centric investing, backing founders in New York when SF and Silicon Valley were still the “it” places. It was a bet on the fact that a firm could back companies in NYC at pre-seed–and survive. And it did. Notation did exceptionally well.
Asylum was born in 2024 when Nick came to me with the belief that the art of investing and the humanistic qualities of investing, particularly at the very early stages, have somehow been lost. This idea deeply resonated with me and many of our collaborators and I decided to go with him to raise Fund I.
During that time, the phrase and the language around founders being artists started to pop up in our conversations. Because there’s an intensity and a passion and an obsession that the best founders have…but it’s also blanketed in emotional softness. As in, these are people doing crazy things to try and start something new and taking a big leap of faith to do it. There’s a place and a time for a company to work with the suits and the bankers, but in the very early days of company building, it’s often more of an art than it is a science. And it is a very human thing and a very personal thing—deeply, deeply personal—for somebody to decide to take this leap of faith to start a company. That is what we’re hoping to build and focus on, and why we felt it was the right time to do it.
Sarah: What characteristics signal the spark you’re looking for, the inspiration you’re looking for, in a founder?
Mackenzie: Each of us on the team might say something slightly different. For many of the founders we back, there’s a true need to build, and need is very different than want. A lot of people want to start companies. A lot of people want to be entrepreneurs. A lot of people want to build something that they think will put them on the cover of Forbes.
The founders that we work with quite literally need to build what they’re building for whatever reason it is, and that reason can be a thousand different things. It could be revenge. We talk about people having a chip on their shoulder. We talk about the way people grew up or where they come from, being highly motivated and wanting to change or reshape the world around them. All the different motivating factors bubble up to an ultimate need to do something. We try and spend time with founders to suss that out.
Lola, our third partner, and I were on a call the other day with a prospective LP and they asked how we’re measuring these things. It’s often through a series of questions that are a bit unconventional. There have been many times when we join a call or a pitch with the founder and we can tell they have been back-to-back in meetings all day. They’ve given the same spiel, and they’ve gone through the same slides. We say: wait a second. Before you pull up the deck, before we do anything else, tell us who you are and why you are doing this.
We try to have a real conversation and get to understand who people are. For us, it’s super important to do that because this is also like a marriage. We hope to work with these people for a very, very long time and to have fun doing it.
Sarah: As Chief Operating Officer, how do you bring structure to the softness?
Mackenzie: We’re a small team of three people. We have a $55M fund. We are very lucky that the three of us have worked at other venture firms in the past. Nick and I at Notation, and Lola spent seven years at Hummingbird, which is a firm based in Europe. We have collected lessons and applied them to build Asylum.
Despite being a small firm, it’s very important that we operate beyond what people might expect. When I think about who we are at Asylum from an operating perspective, we might not have as many resources as other firms, but we match them in excellence behind the scenes. That’s not something founders need to know, but it’s extremely important for our LPs.
If we can structure our foundation to create a world in which things behind the scenes are humming, we can then do everything that we want to do—the stuff that’s a bit more fun and a bit more exciting like collaborating with founders, spending meaningful time with those founders after we back them—because we’re not getting distracted and bogged down by admin and compliance that ends up taking so much time.
There is a fine line between over-institutionalizing what we’re doing and having the flexibility to learn and adapt. We’re doing a good job of holding ourselves accountable to high standards. That includes everything from ops and founder interactions to running a tight process when we’re looking at potential investments. We try to balance being heads down and focused with fun and experimentation.
As a team, our qualities are complementary and help us keep one foot in the fun zone where we take big swings and try new things and another foot in the responsible zone where we have a huge obligation to manage this fund and follow all the legal compliance and other guidelines.
Nick loves experimenting. Too much experimenting makes me so nervous because I’m very Type A. I like a process, and I like everything to be in its little box. Lola is somewhere in the middle. She understands where I’m coming from, but she’s also a visionary thinker. We balance each other out. It’s a dance, but I think we’re doing a pretty good job.
Sarah: I want to know your astrological sign.
Mackenzie: I’m a Taurus. We’re also big fans of the Enneagram here too. I’m Type 6, which someone once described to me as a boy scout or a girl scout. You know, you get your badge, you do your thing, you collect your patches and sew them on your vest. It’s a very COO sign/Enneagram Type to have.
Sarah: From your perspective (see grounded earth sign, Enneagram Type 6), what would you say is the most underrated operational function in a VC firm that outsiders never see?
Mackenzie: Something that we spend a lot of time on is network and community management. I don’t know if it’s obvious or underrated, but community management is a very hard problem to solve, particularly at the pre-seed stage. There are a hundred CRMs that you could use to manage your network, and each is…adequate. There is a lot more to getting what you want from a CRM. A CRM’s purpose is not simply to make lists, like, here, make a list for this, make a list of these people that you want to invite to this party…It’s so much more than that. There is so much uncaptured value within a network and a community of people. If you have the right tools to help tap into that, you can uncover so much. I don’t think that there’s any single product off the shelf that does that successfully.
We use a tool called Attio. We wonder what we can build around it and what we can do to supplement it so that we can truly understand the people who are in our universe. As early-stage investors, it’s our job to meet people and get to know them—oftentimes before they even start a company or before they even quit their jobs. They’re not totally sure when the right time is. It’s our job to cultivate an amazing relationship with them so that, if they do end up starting a company, we’re the first people they call. If you’re not doing that well and you’re not reflecting on who you’re speaking with and who you’re interacting with, you can lose a lot.
I think every venture firm has this challenge and is probably thinking about it in different ways. For us, it’s one of the critical areas to get right, and it’s something we’re still working on. Everybody has a different appetite for tracking things. I’m the ops nerd, so I don’t mind logging into a tool and using it to tag my network. For some people, it’s less natural. They think, “oh my god! What an awful task to have to go into a CRM and log my week’s meetings!” It feels so administrative.
How can you create a world where you’re meeting people where they are in terms of their individual work style while also designing a standard process so that you’re still able to extract the same value if there is turnover or if there is team growth or if people just straight up have different preferences? If you can’t do that, then you’re back to Square One.
Sarah: What advice do you have for someone who wants to work in VC?
Mackenzie: Do not be afraid to be relentless, but intentionally so. There are so many people who want to work in venture and there are so many different flavors and profiles of firms and founding partners and teams and stages and sectors. There are a million different varieties of what working in VC could be. Be brutally honest with yourself about what you want to spend time on.
It’s an intense job. It is hugely time-consuming. It’s not a 9 to 5. Figure out if there is a particular type of role or firm you are drawn to. Have conversations with people to understand what different versions of working in venture might look like and then be intentionally relentless in pursuing what you are interested in doing.
But don’t spam people. There are certain names that I’m starting to recognize because we receive the same emails from them. Persistent emails like, “I’d love to work there.” While I appreciate the hustle, it’s perhaps not the most valuable use of time. Instead of creating noise when you’re trying to meet people at firms, ask if you can create value, and can you continually re-create that value over and over again?
There is one guy that recently graduated from college, and he started emailing us with deal flow a couple years ago. He started doing the job before he got the job. He has become a trusted source for us. If he sends an investment opportunity, I’ll look at it. His emails have become high value.
A few things have happened through this. We know him. We’ve introduced him to other firms. We’re not hiring right now but maybe in the future, he would be on the shortlist depending on the role.
He’s been very intentional. He’s taken time to understand who we are at Asylum, what we are looking for, what type of founder. And he doesn’t stop. Even if we say, “no, this deal’s not for us,” or “this deal might not work out,” or “this is not ideal,” he comes back again. He’s intentionally relentless, and that’s made a difference.
If you want to work in VC, there’s a degree of straight hustling. Things that need to be done. You can tell when people really, really want it. That’s what I would say.