what is your name?

My name is Wilson Chockley but I go by Wil with one ‘L.’ I was named after my grandfather, the original O.G. Wilson. So to distinguish such, I have one ‘L’ in my name, which has been very confusing to everyone throughout my whole life but it gives me a unique name

what do you believe is the most interesting fact about yourself?

I'm one of those guys who, as a kid, absolutely loved dinosaurs, like most kids. But unlike most kids, when I grew up, I never got over dinosaurs. And so when I was in college, I took a class on dinosaurs which turned out to be the hardest class that I took while I was there.

And then recently, during my free time, I decided that I would create a dinosaur-fact Instagram and it basically has no followers. But I post dinosaur facts on Instagram, @DinoKnowledge

I feel like that there are not a lot of people out there with dinosaur themed Instagram accounts, particularly not maybe above the age of eight.

Fun fact: all modern birds by classification are dinosaurs. We have dinosaurs living amongst us.

how long have you been in los angeles?

I have been in Los Angeles for two and a half years.

what is your background?

I grew up in Washington, D.C.

My parents both worked, my Dad is a lawyer and my Mom runs a healthcare think tank. And I was a very, very nerdy kid as you can probably tell about my interesting fact answer on dinosaurs.

I loved, and still love, science fiction and fantasy books and have read an enormous quantity of those books.

I always studied hard and did relatively well in school. I also loved video games and continue to love video games and find myself having to wean off of video games because they can get very addictive very quickly. In high school that meant a lot of Halo and Call of Duty.

I have an older sister, she is awesome. She is incredibly smart, went to Yale and lives in Philadelphia. She has her Master’s in Social Work and currently works with the Community of Philadelphia as a therapist for those in that community that need help.

My sister and I are super different, I’ve always been more outgoing, and she’s always been more introverted. But we have similar views and have gotten along.

In high school, I played a lot of ping pong with my friends who are also very nerdy. Growing up, I was just kind of an average suburban dude.

I went to Dartmouth College in New Hampshire where I was an econ major, which was great because I feel like I got credit for having a science-difficult major without having a science-difficult major. I had no idea what I wanted to do when I was in college, but it seemed like something that would be relatively, generically applicable to any job that I wanted to do going forward.

Little did I know that, past econ 101, everything became relatively theoretical. I think econ 101 is a class that everyone should take because it's relevant to how the world works in so many ways.

But the hardest class that I took at Dartmouth was my dinosaur class. I think anyone would take a class with dinosaurs, thinking it was going to be easy. But it was a rude awakening for everyone. The professor, Kevin Peterson, was a molecular paleo-biologist, and it was everything that a child turned/teenager/turned young adult, dinosaur enthusiast, would want.

After Dartmouth, I relocated to Boston and became a financial consultant. I really had no idea what I wanted to do with my career. There were a couple of kids from earlier classes at Dartmouth who had gone to work at Bain Capital Ventures, a venture firm that I really respected, with people that were the exact combination of smart, personable, and hardworking that I wanted to emulate. And I was like, ‘oh, this is where they go to work? I should probably try to go to work there as well.’

Being a consultant was great in many ways.

It is a great first job in that you learn the basic business toolkit to take anything that you want to do going forward, but the hours end up being pretty long. And frankly, as a junior consultant, you kind of end up just being an Excel and PowerPoint grunt for a couple of years.

But one thing that I absolutely loved was being around the people that I worked with. Three of my closest friends in the world are people that I worked with during my first job as a consultant.

After Boston, I moved to San Francisco and got into the tech world working a bit for startups, and then moved to working at another venture capital company.

When I was working in venture capital, I met a guy named Spencer Rascoff, who co-founded Zillow, and served as their CEO.

At the time, Spencer had just left Zillow and was living in LA, while I was living in San Francisco. LA is Spencer’s hometown and he wanted to start a venture fund in LA. Spencer basically said, ‘Hey. Quit your job. Move to LA, and come help me at 75 & Sunny,’ our venture capital firm.

And so I did, and moved to LA in early 2021 to start 75 & Sunny with Spencer and running that with him.

About a month-and-a-half ago, I took over a company that we had helped launch and incubate called, Dot.LA

Dot.LA is a local tech publication covering the LA tech scene. We are currently in the process of rebranding Dot.LA, bringing it to the potential that we hope to have when we officially relaunch the brand. —

what is Dot.LA? and the mission?

Number one: to shine a spotlight on all the cool stuff that's happening in the LA tech scene. LA is the third biggest startup ecosystem in the country behind San Francisco (Silicon Valley), and New York City.

But yet, there's not been a ton of media coverage on a lot of the cool companies that are based here in LA, with a few exceptions like Snapchat and SpaceX. TikTok’s U.S. headquarters are in LA as well, but outside of a few companies like that, there has really been limited coverage.

Not only do we want the LA tech community to be shared here locally in LA, but we are on a mission to share what is happening in LA tech with the world.

Number two: through our media products, editorial content, to become the center of LA tech digitally and physically in-person, hosting events that bring founders, investors, operators, executives, pretty much anyone that is interested in the LA tech community to know of a physical hub that is available to them.

Historically, Dot.LA put on a couple of great events. Last year, we put on a summit which brought together a hundred VC folks, and it was a fantastic opportunity. We are really focused on this, putting together dinners, panels, and things that can really get the LA tech-scene ball rolling.

how does one approach a VC if they have a product?

If you are a founder, I would be looking for any connections possible. These common connection voids are what we will be fulfilling at Dot.LA, as going in cold, without a connection, is rarely feasible.

VCs are going through dozens, if not hundreds, of emails a week of cold pitches from founders. It is really impossible to sit through all of those, so the most effective way has to get on a VCs radar through a warm connection, something that we are providing to Dot.LA.

generally speaking, what are VCs looking for today?

I think one thing that is being focused on is retention because everybody can have a high number of users, but some might be inactive, say for an online app or product, to use as an example. Then of-course, the need, and competition within the space to keep it short.

But generally, the way to see if there is a space is to see if the market is relatively fragmented with low customer satisfaction, and are there a large number of legacy companies that are not super innovative.

on los angeles vs. san francisco as it pertains to tech…

When COVID happened, a lot of people started to understand that remote work was possible, and that people could live where they wanted to live. And people want to live in LA because it is such a great place to live.

I think that if you asked me five years ago, would I be working in the LA tech scene, I would have probably said no.

But when COVID happened, and remote work, I think that this distributed workforce geographically has meant freedom in choosing.

In LA, the weather is perfect, ninety-percent of the year. The quality of life: you can go to the beach, you can simply do whatever you want, do whatever it is that you love, in Los Angeles.

I have noticed that there’s been a large migration of people from San Francisco to LA over the last three years. But to truly compare and contrast LA or San Francisco to ecosystems, well, they are obviously very different.

San Francisco, as far as I am concerned, will always be the center of the global software tech industry. So if you are a founder, or a VC, you are always going to be competing for a share of the pie.

In LA, there is a shared goal of going for the whole pie, rather than just competing for a share of the pie.

In LA, it’s much more collaborative in many ways than San Francisco. Obviously, the tech community is smaller in LA, but that allows for the community to become a bit tighter-knit as well.

And on top of this, everybody in Los Angeles is just friendlier. Again, we all have the same goal: how can we make LA more of a startup tech scene than an audience? 

what are your hobbies?

When I moved to LA a few years ago, I lived in Santa Monica, and moved here with my girlfriend, now fiance. We wanted to live close to the beach, and every weekend, we’d simply go to the beach and just hangout: read a book, play flag football, whatever it might be.

what are you reading? watching?

I am reading a book called, ‘The Death and Life of Great American Cities,’ by Jane Jacobs. It is a book on how we can help cities become the best versions of themselves, and it is actually an older book, with I believe the first edition coming out in the sixties.

It’s a really interesting book to read, as we are trying to make LA the best version of itself because it is such an amazing location that we have. It should be the greatest city in the world but we just have to push it there.

So that is what I am reading, and as far as watching, well, I am going to give you the trashy reality TV that my fiance and I have been watching and that’s ‘Love Island, Season 10,’ the U.K. version. Let me tell you, it is addictive.

what is a phrase, or a mentality that you try to live by?

My Mom has a phrase that has kind of been a part of our family, and that is, ‘life works out.’ I think that’s just a good way to look into the world.

Life does work out, and this will lead to something better. I think that this is just a good kind of overview, so I try to keep that.

where is your favorite los angeles morning hangout spot?

Santa Monica Beach on a Saturday morning before the crowds have gotten there.

where is your favorite los angeles morning hangout spot?

The Father’s Office in Santa Monica

how would you describe los angeles?

A city of potential.

People come here to pursue their dreams. I mean, the classic example are those living here to pursue their dreams in Hollywood.

But now, people are starting to do this with the tech industry, and I think of the city, as I alluded to earlier, as one that has so much potential. I think it’s such an absolutely fantastic location by the beach. The weather is so perfect.

I think LA has a lot of potential to be a much better version of itself in twenty to thirty years.

how would los angeles describe Wil Chockley?

I would think LA would describe me as a friendly and comfortable dude and somebody just trying to make LA a better place in the tech scene.

Interested in sharing how you are curating LA? Surf with us, we’d love to catch some vibes and hear about what you’re doing