Natalie Dillon is a Principal at Maveron, an early-stage consumer VC firm backing extraordinary founders who shape the way consumers live and the culture of tomorrow.
This interview is interactive and will also feature some fun facts about Natalie. Make sure to click or tap on the various visual elements and squiggly lines that you see. Swipe / scroll right or click the circles at the bottom of the page to keep reading.
80% of my time is spent with founders. That ranges from listening to pitches to working with founders at our portfolio companies.
20% of my time is talking to other investors: trading deals, sharing notes, stress testing a thesis and so on. I will say a lot of my time is spent in meetings. On Fridays, I try to leave my schedule open for deep-thinking, research time, so if there's a space I’m really excited about, I’ll use this time to dive in.
📍Mission Hill, SF
I grew up on these courts.
I really feel so blessed to do my job. I couldn't imagine doing anything else. The thing that truly gets me the most excited (and will bring tears to my eyes) is how companies today are just amazing vehicles for driving social progress.
It’s really, really exciting when you feel like you're backing an extraordinary person that sees the future before anybody else does, and this person isn’t just satisfied with creating a beautiful product or service but wants to actually create a movement. As an investor, it can feel like you've played a tiny role in being a part of that movement.
📍Golden Gate, SF
Golden Gate Park courts are where I met my best friend and then later high school co-captain.
Parade. They want to become the next generations Victoria's Secret and Hanes.
Thinking about how many young women grew up with Victoria's Secret and the reflection of womanhood, sexuality and femininity that was pushed upon them at such a young age was just not right. Victoria Secret had completely unfair expectations of body type, color, size and what it meant to be a woman.
Being able to back a company like Parade that is rewriting America’s underwear story and presenting a totally new and modern view of womanhood, sexuality and femininity is amazing.
Thinking about my daughter and the young women today who will grow up with a brand like Parade makes me so happy. It just gives me goosebumps.
The way I see it, determination is the ability to overcome obstacles through creative problem solving and grit. Usually, that's applying a lot of different strategies and solutions to a singular problem. Whereas persistence is using the same solution to address the same problem. Yes, you still have grit but you’re just using the same tactics.
In a pitch sense, persistence is the founder who continues to send the same cold email with no personalization, whereas the determined founder gets to know a founder in our portfolio and then uses that as a way to get a warm intro to us which makes the entire interaction more personalized and thoughtful. They figured out another way to get in front of us.
I remember when I started interviewing in venture one of the questions I'd always ask the partners was: How do you build conviction? How do you know when to say yes to a deal, especially when there's no data because it's early stage? Nothing’s been proven. How do you know when to say yes and when to say no? A lot of the advice I got was “listen to your gut” or “you have an instinct for it.” While there may be some truth to that statement, how can you teach a “gut instinct” to someone who is trying to learn the craft of investing or get into VC? I never found that advice to be quite helpful.
Another thing that people often say is that it’s really hard to break into venture. There’s definitely some truth to that, but at the same time, if you're not getting invited to the party, start your own. You can host a meet-up, start a blog or a podcast. Showing that you are genuinely passionate about something goes such a long way. You don't have to wait for other people to call you. You can pick up the phone and start your own thing. I think people really, really appreciate that sort of hustle and entrepreneurial spirit. Those would be the two things I feel like I hear people say, and I’ve had to retrain myself to think differently.
📍Stanford, Palo Alto
As a kid, I dreamed of one day playing on the courts at Stanford.
I’m going to cheat a little on this one! But the first major deal I was a part of at Maveron was for this company called Otis, which wants to become the stock market for culture so you can buy shares of shoes, sneakers, collectibles, etc. I'd been thinking about millennials' view of physical assets and investing in sneakers, and I saw a HYPEBEAST article about Otis. I was super curious about Otis, so I slid into Michael (founder of Otis) Twitter DM’s and said “Hey I'm Natalie, I work at Maveron. We back XYZ tech companies, I saw your article on HYPEBEAST, and I’m really interested because of these reasons. I’d love to meet up the next time I’m in New York.” A few months and many meetings later between our team and Michael’s team, Maveron ended up leading the Series A into Otis.
Well, it was actually from Cami , the founder of Parade.
It’s funny because this was many years ago when she was a student at Columbia. She was interning at the time at Rough Draft Ventures and Tusk Ventures. She also always had like 10 different jobs going on and hustled so, so hard. Cami emailed me and had a very specific question about a very specific portfolio company that was not well known. I remember thinking: “Wow, this is the most specific and thoughtful cold email I’ve received, and it’s from a sophomore from college. Who is this person? I’m intrigued.” You know, it turned out obviously she is a very special person, and many years later, we’re leading the Series A into her brand Parade.
I tell VC's to respond to students' emails because you never know, they might start a company of their own. We’re very lucky to be on the Parade bus.
Oh my gosh, 12 year old Natalie was on a social justice warrior path! She would be like “Venture capitalist?! Where did that happen?” That being said, I think she would make sense of how I landed here because I really do believe that companies are just incredible vehicles of social change. I think venture is really unique in that a lot of it is driven by one-on-one relationships. When I think of change and impact on a personal level, it all stems from relationships whether it’s my parents, my mentor, my coach or my best friend. Venture is a place in business where one-on-one relationships can have a huge, huge ripple effect.
📍UIUC, Urbana Champaign
The court at University of Illinois is where we won we won the 2013 National Championship title as the underdog.
Note: Natalie did end up achieving her childhood dream. She attended Stanford and walked-on to the Cardinals Tennis Team. She ended up earning a spot on the Cardinals lineup and playing in all the games by her junior year.
Humor is a great diffuser, if you know how to use it. When you’re in an awkward setting, everyone in the room is appreciative of humor. I try to make fun of myself and not take myself too seriously. If you allow yourself to be vulnerable and be the butt of a joke it opens up the room for other people to joke around and poke fun at each other.
Thanks for reading. If you enjoyed this interview, please subscribe to our newsletter!