Natalie Gray

Co-founder & Head of Product, Cover

Natalie Gray is the Co-founder and Head of Product at Cover, a mobile insurance technology company.

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Rohit: Hi, I’m Rohit. I’m the co-founder and the CEO of Stilt and today, we have Natalie with us. Natalie is the co-founder and head of product at Cover. Cover makes getting property insurance — car, home, renters, jewelry as easy as taking a picture. Natalie holds a bachelor of commerce and a BA in Mathematics from Queens University and then she briefly attended NYU for a Masters in Marketing. She’s a Y Combinator Fellow and YC Alumnus. In 2017, she was selected to the Forbes ’30 Under 30’ class. Prior to cover, Natalie was lead designer at Stylekick and then a mobile designer and product growth manager at Shopify. Cover has raised $27 Million in equity from Social Capital, Tribe Capital, Samson Ventures, Y Combinator and others. Thanks for talking to us today!

Natalie: Thank you for having me.

Rohit: I’m excited!

Natalie: Cool.

Rohit: So let’s start with your background. How did you get into the tech industry? So your background is in marketing.

Natalie: I did not get into tech intentionally by any means. So right after graduating from Queens, I was armed with a business degree, so I could do anything I wanted. And my big goal was to work in retail and that’s what I did right after graduating. So I had moved to New York, I had a job with Rush Communications which was the umbrella company for Phat Fashion. So Baby Phat, Phat Farm. That basically was the career that I had wanted for myself.

Rohit: Right.

Natalie: I kind of decided that I had wanted to come back to Canada after a year and a bit in New York and at the time, my current co-founders Karn and Anand — Cover is actually our second business together, they were playing around with the Connect Sensor and ways to assess fit for online shoppers. And given I had a fairly healthy rolodex of New York Retailers, they asked me to also get involved in the sales arm of it. So the rest is history. I did a bunch of different tasks for them and then joined them as co-founder shortly after.

Rohit: Got it, and did you do Stylekick before you went to NYU?

Natalie: No, it was after.

Rohit: And why’d you choose to leave NYU?

Natalie: That was a pretty hard decision. Masters programs are extremely expensive. They’re definitely an investment. NYU was plus 50K USD per year just for tuition. I just didn’t feel for that cost I was truly getting value from that degree, so I made the choice to stop the program a year in.

Rohit: Got it. And a lot of people sort of have to take loans and they have to get into debt financially to do that and then they’re not able to get out of it because it just seems like you have to finish it to get anywhere.

Natalie: Yeah. Breaking that mental barrier of “I started it, so I have to finish it.” That was probably the hardest. And the scariest thing, honest to god, was calling my mom and telling her this is my decision. But she was supportive, I’m still here. So that’s good.

Rohit: So after dropping out of NYU, you want back to Canada?

Natalie: Yes. I was on a visa, I was on a student visa so I did have to come back to Canada.

Rohit: And what did you do there, then?

Natalie: So actually being in the program in NYU, it touched upon math and budgeting, and I had done a lot of accounting and whatever in my first degree in commerce, but again this was like another every level taste of it. I did notice when I was working in New York that I was getting ahead because I was able to do analysis and budgets and finance. So I thought, I had this moment where I was like, I don’t know if I want to get — maybe I want to go into academia, and just overall, maths is just something that I’ve always struggled with. So I decided to go back to Queens and then do my bachelors in mathematics, which I took a 3-year degree and crammed it into one because I felt at 23, I was too old to be in school. That is no true, don’t do that. But that’s what I did and while it’s not a skillset that I’m using on the daily — there’s no place for pure mathematics in my daily job now, I do feel that it made me smarter. I learned how I think, I learned how to learn. I basically figured out — if I need to do anything hard, this is how I can do it.

Rohit: Right, and as you were doing your mathematics degree like programming and coding never interested you or wasn’t something…

Natalie: I touched upon it in some of my classes so I was in 3rd year engineering. I had to get special permission for all these classes and truthfully, they probably shouldn’t have given it to me. But I ended up doing really well, so let’s just put that out there. The coding part of it, MATLAB — it wasn’t something that I truthfully enjoyed. It didn’t really spark some interest in programming that I didn’t know that I had. I was more so always interested in human-computer interaction and design and kind of feeding the art nerd in me as opposed to programming.

Rohit: So your art knowledge is all self-taught or…?

Natalie: I am a self-taught designer.

Rohit: Yeah?

Natalie: As you know, being in a startup, you have to — where is the gap? Can I afford this gap? And if not, you just pick up the slack yourself and I think it’s always better to — especially when you’re making those early valuable hires, have knowledge of who you’re bringing onto your team and the level of control that you’re giving out. So I had designed websites through college, so I thought — I can do this, I can pick this up. And again, using the same learnings as in the maths degree, this is how I acquire skills — so yeah, I am self-taught.

Rohit: And as you were learning it yourself, how did you go about adding structure to it? So a lot of people now learn coding, either on their own — they’re self-taught. There are infinite sources to do it. How did you add structure? Did you have mentors that helped you? How was that process?

Natalie: So I just worked backwards, actually. So I was looking to bring somebody onto the team that was strong in design — having done many interviews looking for the perfect person, I had a list of what are the skills that I truthfully would like to see in someone coming to join Stylekick at the time. And then I worked backwards. I dedicated x number of hours per day in getting better at these skills. At the time, in 2014, 2013-ish, there weren’t as many resources for UI/UX as there is now, but there was Pluralsight — there were tutorials. It was kind of on the cusp of having all of those resources. So I had access to what I could, I used what was available but probably the most valuable thing was picking apps that I used on a daily basis and then deconstructing them.

Rohit: Interesting.

Natalie: So everything from here it is on paper to here it is in a prototype to when tools like Origami came out or Principle — down to the small interactions that you are not necessarily aware of and you can learn a lot from doing that.

Rohit: Interesting. And you did that after you started Stylekick.

Natalie: Yes, this was after. So I had some experience putting together not-so-stellar websites, but this was my first full endeavor into mobile.

Rohit: Right, interesting. Generally, as you’re answering people also — I think the design part came out really well and in my mind I’m thinking okay, that’s a snippet, how you taught yourself to be designer basically. And from what I have seen, people love anecdotes so anything interesting in that, if someone helped you or you faced challenges and then came out of the other side glorious and victorious is what people are hungry for.

Natalie: Okay.

Rohit: Cool. So this is all after Stylekick and let’s just also talk about how you met your co-founders Karn and Anand. I feel like you guys know each other since forever.

Natalie: I don’t, but Karn does. So Karn and I actually met at Queens. So he was studying commerce as well. He was a year ahead of me. It was really strange because all of our friends were mutual and we didn’t meet up until his very last week of his last year and we met super randomly and then we kept in touch. And Anand was Karn’s friend from high school. So they had won a very small high school — actually it wasn’t small, that’s a lie. It was Mississauga, which is a very huge suburb of Toronto. They were in the Mississauga newspaper for having won a business competition. They made like a Kazaa competitor. So they have known each other for over 10-15 years now, maybe probably more. So I think they’ve gone back since kindergarten and Ben was our first hire into Stylekick and he’s just been with us ever since and then joined us with cover as a co-founder.

Rohit: Right, and how did you think about maybe starting a company with them and how did it sort of evolve into Stylekick or Cover? Being friends is one thing, being co-founders is another.

Natalie: Oh yeah. I think I definitely lucked out. I definitely lucked out with 3 really amazing people to work with. We worked so closely together for years and the relationship is still really good and still really healthy. It wasn’t — I don’t think in the early days that you start off thinking that I’m going to build this massive company. You kind of start out with a problem like what is this problem that I want to solve? What do I need to solve it — and then who should I be bringing on to kind of help me? And it slowly kind builds and builds from there up until the point where you discover — I have something of value here that I could make money from, from this solution that I’ve come up with or this understanding of this problem that I have. And that’s really where the journey to beginning a startup really kicks off. And I think the misunderstanding comes along that startup doesn’t mean you start a business. It’s a model that you’re pursuing. There’s a lifestyle business where you’re trying to generate your own revenue to reinvest in your own company. And then startup where you’re looking for huge infusions of cash to get you to certain milestones at a pace that’s breakneck, basically.

Rohit: Right, right — it’s true. And as you sort of decide to start a company with them, where did the idea for Cover come about? How did this evolve into what’s cover today?

Natalie: So at Stylekick, we got really good at mobile. I think we had pretty good timing on our side. So we initially started off being a brand plug in and then a website, and then kind of fell into mobile as a growth hack and then we just saw so much more traffic through Stylekick and stuck at mobile and through to website. So that’s where Cover being mobile-focused came from learning that part of it. But Cover, the idea as a whole — Stylekick needed business insurance. So I was like — I don’t know where I can get that. We have employees now, we have to get legal. So I legit just texted my mom and was like who sells you insurance? And it was this guy that lived down the street from them for 60 years and has been insuring my family for years and years. We go to his office to drop off a paper check for our small business policy and he’s just got floors upon floors of call center in prime financial district in downtown Toronto. So we were like whoa. This is pretty interesting — this processes wasn’t great. And this was very expensive and there is something here. So we started to be aware of it and then we slowly started coming up with different ideas.

Rohit: So what year was that?

Natalie: Oh my goodness. That was 2015.

Rohit: Okay, so 2015, you need business insurance, you go to this guy who has been living in the same…

Natalie: I think business insurance came — we needed that 2014, and it kind of just marinated for a really long time and Karn worked in consulting previously so he was a consultant for large banks and creating risk modeling and everything. So he had seen that industry from the top. From at the top. And then we were kind of experiencing it from a consumer, on-the-ground kind of level. So it was interesting. We didn’t jump right into this one. We spent some time thinking about it and thinking about the approach and then eventually it came down to ‘let’s do a hack day’. Why shouldn’t insurance be as simple as taking a picture and just getting the insurance?

Rohit: Right, and when was that hack day?

Natalie: I think it was sometime in the fall of 2015. We just kind of put it together and then where YC comes in — we had applied so many times with Stylekick, like 3 times. They interviewed us, they rejected us. It was a pretty emotional rollercoaster on that one. But we reached out to them with Cover and we were able to get into that batch. So we quickly gave notice and moved to California.

Rohit: So earlier you planning to just stay in Canada.

Natalie: Oh yeah. So Stylekick had been acquired in 2015 and we were ready to hang out for a little bit, Shopify was a phenomenal company, so we couldn’t have asked for a better acquire, we got to work together for the initial few months. So we had planned to settle a bit. We didn’t expect the response to cover that we got. The first app was awful. It had 4 buttons and they all opened the camera, and that’s it. And we saw in the first 24 hours, people were trying to give us their credit cards and they were trying to buy insurance from the broker partner that we were sending leads to. So when we got those results, we had the chance to do YC, which had always been so elusive to us previously — we’re like we have to go. We have to do it, it’s still pretty real.

Rohit: So you applied to YC, you flew down here, you interviewed and you got right in.

Natalie: I, to be truthful, did not come to the interview. I was very upset. I just felt like they’re going to bring us down there, they’re going to set the spark alive and tell us ‘no’ again. I’m not even going. Then it happened, so…

Rohit: Okay, and then you decided you’re going. So applying to YC and getting here was the primary reason you moved to the US. What were the initial visa types or statuses that you moved here on and how did that come about? And then we’ll go into the story of cover.

Natalie: So Canada, between the US and Canada, it is a bit more straightforward than other places. Like Canadians are, and I think the US is the same. We’re allowed to stay in our neighbor’s country up to 6 months before we have to be on visa. And given that YC was a learning program, it was fairly straightforward for us. But we eventually we’d have to go onto 2 working visas. And I take my hats off to people because the US and Canada is just very straightforward. It’s one English-speaking to another English-speaking so I can appreciate that that’s a hard process.

Rohit: Okay, so you moved here, you attended YC, you were on this neighboring country NAFTA visa?

Natalie: Yeah we were on the TN NAFTA visa.

Rohit: And you graduate from YC, you raise a [ph ‘C-Chawn’ 24:16]. Right, and that’s when you really started sort of being — as you have to hire people, you started being a full company.

Natalie: Truthfully, we didn’t hire for quite a while outside of YC because we had to get the visa situation in order and insurance is very heavily regulated, so for us to not be shut down by the regulators, there was quite a number of hoops that we had to jump through to make sure that was all done. So we basically heads down worked on that. Through YC we were also operating as a legion. Meaning that w would bring customers in and then send them to 2 broker partners we had vetted. Post YC, we wanted to be the broker and be the brokerage, so we just spent that time making that transformation. So once that was complete, then we started hiring our sales team out, which was I think 4-5 months outside.

Rohit: Got it. So you built all of this and then you also have to get all the licenses in each state, I think, individually and that process takes a really long time. So you do that, and then what do you do? So now you have all the licenses. Then what’s the next thing you guys did?

Natalie: So there are many layers of licenses in insurance, so first you have — all of us, I’m a licensed broker.

Rohit: Yeah, I remember you guys were studying for an exam or something like that.

Natalie: Yeah, so I wrote the exam, basically all the founders wrote the exam. And the Cover itself had to be a broker. And once you are licensed in each state, then you have to go to the carriers and ask: Can we sell your products? Then you have to get your appointments directly. So there’s a number of layers that we had to go through. So slowly but surely, first was California and then we started adding more and more appointments where we could sell to more customers across the US. So right now we are at 50 states with 30+ carriers and then in Texas we sell our own auto insurance product.

Rohit: Got it. As you are sort of building all of this incredibly complex regulatory hoop-jumping stuff.

Natalie: You can relate.

Rohit: We had to do some of it.

Natalie: Many drinks have been shared on this topic.

Rohit: We have to go, we have to get fingerprinting done. Our investors have to go and get their fingerprints done.

Natalie: We didn’t have that. That’s… okay.

Rohit: We had that too. If anyone owned more than, in some states, 5% of the company, they have to go submit their financial personal residential history and financial history for the last 10 years and we have to convince investors to do that.

Natalie: Yeah, I can imagine.

Rohit: They have to tell you how much money they have and it gets super complex to do it, especially if it’s a big fund, then it’s even more tricky. But as you guys are sort of — you moved here to the US from Canada, how did you go about sort of building a network because you must have needed that for regulatory stuff or other hiring, later, when you did. And also for investors. So you get to know them. I mean obviously YC helped, but what was that process like for you guys?

Natalie: So we had tried to raise — first, okay for quite a while we were back and forth from Toronto to The Valley — so we had a fairly decent network built. A network of no’s if you want to call it that!

Rohit: Let’s talk about Stylekick. When you were trying to raise for Stylekick, how did you find investors to pitch to?

Natalie: So going back to — like the first question with Cover, I’d say YC was critical for that. And then back to Stylekick, where we didn’t have that vetting, a lot of our strategy was to reach out to entrepreneurs or companies that we either wanted advice from, admired, or they were doing something similar and really just pitched them what we were doing at Stylekick. And the ask was, just check what we’re doing, what do you think of our pitch? Just kind of building a network, building a contact we didn’t have previously. And at the end, they liked what we were doing, they liked us. We’d as what they would offer to give us an intro to their investors. The warmer the intro, universally that’s always better. So whether that’s through an entrepreneur that you’ve just met or it’s through YC — warm is always just far more effective than out of the blue. You can get to a partner faster, you can get to a decision faster and then once you’ve got the ball rolling, it’s a lot easier than not.

Rohit: Yeah. And a lot of it is from a point of view of someone who doesn’t have a network here, you guys reached out and did something valuable. Your product was good, so people liked it and they were willing to intro you because of that.

Natalie: I think at Stylekick, they liked us. To be honest, I don’t know if they really loved our product very much, but they liked us. They thought we were interesting people. Canadians, everyone loves us, we’re pretty friendly — but then when we came back with Cover, which is, here is the same people that you like before but now here’s a business that you can see success for — that was a really different ballgame for us.

Rohit: Cool. So now, and since YC, you have raised seed, series A and series B of total $27 Million. How did the — tell us a little bit about the building of the company. You guys are 3 and a half years old now.

Natalie: Yeah, I think we’re 3 and a bit years old. We have just under or at 60 people and those are split between San Francisco and Toronto. And more so — insurance branch is here and then engineering is in Toronto.

Rohit: Cool, so a 2-part discussion. 1 is building a team and hiring people: How did you guys initially sort of go about hiring your first engineers for example?

Natalie: Really, we hired backend engineering first. It was really a function of need. At that time, all the founders were still operating as IC’s so we know which founder needs assistance at this time and that’s really what dictated which hires went to which team effectively. So back then, you know — Karn was growth and financing. I was design and operations, I want to say, but really that was just maintaining the house that we lived in, making sure the bills were paid. And then Anand was backend and Ben was front end. So we were quite a backend-heavy product so our first 2 engineers were backend and that’s really what dictated how and when we hired people.

Rohit: And how did you go about finding those first 2 engineers?

Natalie: So those first 2 engineers were based in Canada just because of network. Hiring in SF is hard. And when you have a very big network in another city of talented people, you just kind of take what you can get when you’re small. And for us it just snowballed into creating our product engineering office over there. There’s a lot of really good people out there.

Rohit: So when did you really start hiring in SF? When was your first hire in SF?

Natalie: Again, so we kept it fairly small. Our first hire was an insurance person. We didn’t have that yet, so it was really helpful. So we just really hired a former commercial agent and then we hired a previous VP out of Metromile. So that was [ph ‘TX Start’ 32:33] the whole sales org piece of it, which was not in any of our discipline.

Rohit: And the sales org is in SF?

Natalie: Yeah, it’s based here. So as an American brokerage, we too have to have boots on the ground here.

Rohit: Interesting, so as you are sort of building a team — obviously because of network, you started hiring first in Canada, which makes total sense also, it’s cheaper to hire there. How do you sort of manage a remote office from the beginning?

Natalie: It’s hard. It’s a lot harder than I think any of us really expected to be. You really have to be intentional with the type of remote model you are pursuing. If the entire company is remote, it’s very different in how you manage your building process, your documentation, your communication as opposed to being partially remote. So the way that it runs, Cover sales and insurance is here and then product engineering is there. So we do have 2 complete offices. And having teams partially remote doesn’t work as well. So with each additional 10 people, maybe even less, you do have to continually revisit this hypothesis of remote to make sure that everybody has all the information they need, are they being their best, most productive self? And then just retro-ing and changing it when things start to break.

Rohit: And those are some key points that I want to touch on further, so what were — I know Anand flies a lot to Toronto. At least 50% of the time I met you guys, he’s like “I’m flying to Toronto.” Or “I’m in Toronto, I’m going to fly back.” You were there for a month or so yourself.

Natalie: I’ve been there since February, actually but I did come back just in time not to be there for the Eastern Conference finals. Not upset. Pretty upset.

Rohit: Yeah, so I actually see that it’s tricky to manage that kind of team? What were some initial kinds of challenges that you guys faced and how did you figure out the processes to cope?

Natalie: Well, I think for my own team, I like to be very collaborative. There’s nothing, I think, better than a good whiteboarding session — that’s exceptionally hard to do with a conference call and a camera. Initially, I was more so based here. I like being close to our sales team, they’re the main touchpoint for our customers — but then when my role evolved more so to a people management type of role, it was critical that I be there. Communication has just been substantially better. It’s better to get things solved more quickly. So that kind of was the trigger for me to now spend the majority of my time in Toronto and part of my time here.

Rohit: And how many people do you manage actively now?

Natalie: I believe our product team is 10 people but my direct reports are 3.

Rohit: 3. And have you managed people before, or is it the first time.

Natalie: This is the first time I’m managing a scaling product org and it’s like that’s a new kind of hard.

Rohit: Yes — So let’s talk about this new kind of hard. How do you learn to manage? I’m sure everyone makes mistakes. Maybe you did too. What were some initial mistakes and how did you learn to manage such a fast-growing company.

Natalie: So I think there’s a point in time for every founder when they realize — at this pace and at the scale they want to reach that they’re better off getting expertise elsewhere. It’s kind of ingrained into us that if you want to do something, just learn it, do it quickly, execute, iterate. And at some period in the company’s history, that kind of breaks. So really, we’re — our roles as founders kind of change into basically money, vision, hiring. So I know that there are designers out there that are substantially better than I am. There are product managers that are substantially better. So my best value to the team at this time is making sure I can bring those people in and then keep them. Definitely have made management mistakes. Probably one of the biggest ones is assuming that everybody thinks and behaves the same way as the founding group because that’s not — that’s grossly untrue. Whether it is how they want to talk about work or talk about their personal growth. I think probably managing and cultivating personal growth is very, very important to people in a scaling org and needs to be a cornerstone of each of those departments scaling. So that was something that needs to be attended to continuously and I think that getting very seasoned managers, people that have scaled before — that type of experience and insight is invaluable to any growing company.

Rohit: And sometimes this becomes a little YC or something else where you find people who can — who are like mentors or guides for helping you make less mistakes. You still make mistakes but you may make less mistakes. Have you found any mentors or people who have been helping you throughout? That can be investors or others who you know personally.

Natalie: Our main investor so far has been Arjun Sethi from Tribe — so definitely known him for his experience, especially as a prior operator. Really be engaged in the startup community, like even our conversations — like [ph ‘paying you’ 38:53] like, “Oh man, I’m stressed, do you have anything about this? Oh no? Just listen.” I think it’s always good to share those stories because it always feels like your story is the most unique, the hardest thing that has ever happened in the face of the world because we are millenials. But there’s a lot of great programs, I think, being offered from funds that now see helping and coaching their investments past the seed and A stage is really critical. YC Growth for one, has been great. I’m part of a group being hosted by first round — that’s specifically targeted towards product founders. So there’s resources out there and I think there will be more as the success of these early programs kind of shows.

Rohit: Yeah, and that’s kind of how you sort of learn to scale yourself, Mae less mistakes and just makes the company growth…

Natalie: I mean the big mistakes are inevitable. I think the more we grow as companies, I know so little as compared to… I know nothing, I literally know nothing. And just kind of being open to that, because you are continually going everyday into new unknowns you could not have anticipated when you were 4 founders trying to put together a seed deck.

Rohit: Right, fair enough. That’s good. Now let’s just dive a little bit into what next. So what’s Cover going to do in the next 2-3 years?

Natalie: That’s an eternity in startup land. So for ourselves, we just recently launched our own auto insurance product in Texas. So basically instead of just buying through Cover, you will be buying policies from Cover. So we’d like to expand that. Selling more of our auto insurance policies in more states and then growing to more lines. One thing with insurance, it kind of tracks your life like your bank accounts and people want — we can offer discounts of there are bundles. So auto, home, really any other property lines and then owning more so of the servicing experience, so transforming into the full stack, full service carrier would be our long-term goal that we are working towards.

Rohit: And you guys are going to be focused on making the app better and it’s going to be a mobile product.

Natalie: I don’t think it’s going to be outside of the app. Mobile has always been our area of expertise. So far, it is our flagship product, but I’ve always thought of it that Cover has an app, not that Cover is an app. So the way that we’re building product it to set ourselves up for that. How do people want to buy insurance? How do they want to interact with their insurance. I think what we learn from the bigger carriers is that as long as we’re really in tune with that, we’ll be successful.

Rohit: Cool. One question I just remembered. You guys spent $800,000 on buying the domain name. How was that? I think Anand has wrote something about that!

Natalie: Yeah. It’s interesting when prospective hires are like, were you those people? We’re like yeah, we’re those people. Good decision. Insurance is very competitive. Especially with SEO on web. We viewed it as Cover is the name we want to go with. That’s the branding that we want to pursue, it makes a lot of sense for insurance and the larger we grew when people were squatting on these domains, the more expensive they’ll become in the future. I don’t recommend doing a move like that to every founder. I actually advise very strongly like — “Don’t do it!” directly to the camera. You have to make a very conscious choice, you have to really decide that this is the branding we want to pursue, this is the word that we want to buy effectively and then be sure of that, because at our stage we could have either rebranded, chose something else that was substantially less money, or kind of full leaned into it. So I think that again is the choice of the founders.

Rohit: But I’m also trying to sort of imagine what the discussions would be like — who floated the idea of “Let’s buy it for…” this and then surely someone would have said this sounds like a dumb decision! To spend so much money on buying a domain name. And then there are investors whose money is being spent on that like — I don’t know how they would respond, like are you guys crazy?

Natalie: We worked very closely with our investors, which is why we got such a good deal!

Rohit: Okay!

Natalie: That wasn’t the first offer at all. That world of domain selling — that’s a different world. I don’t know a ton about that, but they were supportive. If you give good reasoning, you have your logic as to why this is a good decision, your investors will support you. That’s why you partnered with them in the first place. If every time we were like we want to spend radical, they’re culling us down — that’s probably not the best working relationship to have, but it wasn’t made lightly. I think we kind of throw it around like oh, here we go. But it wasn’t. It was a really serious conversation amongst the founders, our investors — even our our broader team, if this is something that we should be doing. And we had committed that cover was the right name and brand for us — so I do remember the moment that we called the broker where we were like, “Do it. We’ll send you the wire.” We just didn’t talk for a little bit. I think we were on our way to South Bay and we just kind of opened the windows and let it sink it, what had just happened.

Rohit: I mean we also spent like $50k. Compared to $800k it just seems so much cheaper. We waited for 9 months to buy this domain and tried to rationalize it every possible way in terms of future brand value, how many customers we can get and does it even make sense? We had the .co — so we were still .co and what made us change our mind was that people were not trusting the .co domain.

Natalie: That’s true.

Rohit: People were like, “Oh, this is a company from Colombia giving money…. Because .co, I thin is the national domain of Columbia. Like this is a company from Columbia giving money to immigrants. They just want your personal information and they’ll never give you money. And a couple of comments like those just made me think — if that kind of narrative continues, it will be difficult to just gain people’s trust.

Natalie: For sure. And insurance is very much the same. You have competitors spending billion dollars per year on brand equity and awareness and trust, so we couldn’t be use Cover, getcoverapp.com We wanted to own that domain, own that space. That’s another thing about having Cover as a word, it wasn’t a word we made up. There were no misspellings, we owned it. So we have both cover.com and coverinsurance.com.

Rohit: Got it. Cool. So as you’ve gone through this journey, doing Stylekick — companies in Canada and the US. What’s your advice for new founders starting companies?

Natalie: Starting companies from Canada?

Rohit: Or the US — whichever one you want to pick.

Natalie: Oh man, that’s a very large question.

Rohit: Just give us your stream of consciousness on the things they should definitely do, things to 100% avoid, making tough decisions like buying an 800k domain or the initial hiring.

Natalie: I think through all of that, what has really helped me is just the amount of trust that I have in my fellow founders. Seeing through hard decisions, hard minute decisions, failures, successes — just having that core group and being able to fully trust their areas of ownership has been, I think, just that is our success. So when choosing, I know that it’s always — I have 2 technical co-founders, that’s very important. But when looking, if you are a non-technical co-founder looking for somebody else, it’s more than they just took computer science and they know how to code. It’s really do they believe in the mission as well? Will they see you through hard times and is it a resume builder or is this something that they truly want to do with their career? And if you choose those people, very carefully approach problems from a logic perspective always. It can get heated and we’ve been lucky where we don’t get heated because we know we’re all in there. We all have a common goal.

Rohit: Anand and Ben are super chill — I don’t expect them to…

Natalie: I have the most energy. By sure, out of the 4 of us and they have kind of accepted that, but again we all want Cover to be successful. So we all may have four different hypothesis of how to get there, then it’s an exercise. Okay let’s flush out these 4 approaches. Which one can we validate faster, which one will cost more up front, and then we make all of our decisions based upon logic and among the common goal of succeeding. So that has been the way that we have approached most things. And if we have trouble on our own teams or trouble not the choices we’ve made, we still have that core group that we can come back with. And even though we’re on opposite sides of the content, we do make time to have our catch up amongst the 4 of us twice per week to make sure that we stay on the same page. And if you are a brand new founder and you are living with your co-founders, invest in cleaners. Your life will be substantially better if you do that.

Rohit: Yeah, we’ve been there a couple of times. It’s just like you eat, you work, you go to the gym and you just stay there all day long.

Natalie: We still live together, it’s still fine.

Rohit: Oh, it’s still the same place?

Natalie: It’s still the same place.

Rohit: Interesting. So definitely, at least twice a week.

Natalie: We do it once every two weeks, to be honest. That’s all we need. There’s nothing to fight about if you can approach your work problems…

Rohit: Who fights about it? Like who doesn’t clean that you have to…

Natalie: But that’s the beauty, that doesn’t matter. There’s no finger-pointing.

Rohit: Okay. Cool. Thanks for talking to us — you’re super fun. Appreciate it.

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