Y Combinator Startup Podcast - #114 - Karn Saroya

Episode Date: February 27, 2019

Karn Saroya is the CEO and cofounder of Cover, which was in the YC Winter 2016 batch.Cover is a nationally licensed insurance brokerage. You can use their app to take a picture of property you want to... insure and they’ll connect you with their insurance partners so that you can get the best price and coverage.You can find Karn on Twitter at @karnsaroya.The YC podcast is hosted by Craig Cannon.***Topics00:36 - Karn’s intro01:01 - Using computer vision to identify and catalogue property2:28 - How Karn ended up starting Cover3:48 - Being a maker vs. an advisor5:58 - Stylekick, Karn’s previous startup9:28 - Joining Shopify10:08 - How the idea for Cover happened11:58 - The capital-light way to start an insurance business16:28 - Underwriting17:58 - Lead generation20:18 - Product development21:28 - Buying Cover.com for $750k24:53 - Being engaged to a cofounder28:43 - Managing two offices and cultures30:58 - Being an international founder in YC31:58 - Advice to people in the current batch of YC

Transcript
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Starting point is 00:00:00 Hey, how's it going? This is Craig Cannon, and you're listening to Y Combinators podcast. Today's episode is with Karn Soroya. Karn is the CEO and co-founder of Cover, which was in the YC winner 2016 batch. Cover is a nationally licensed insurance broker. You can use their app to take a picture of property you want to insure, and they'll connect you with their insurance partners so that you can get the best price and coverage. You can find Karn on Twitter at Karn Saroya. All right, here we go. All right. So today we have Carnes-Roya, the CEO of Cover, which was in the winter 2016 batch of YC. So, Karne, what does Cover do? First of all, thanks for hosting me. I appreciate it. So you can think of Cover as a multi-line national property insurance entity. Our customers download our apps. We ask a couple simple and running questions and they take pictures and videos of things they want to insure. So this could be cars. They could walk us around their homes, pets, jewelry, electronics. We basically make a market for just a bit anything you can take a picture of. And it's processed with computer vision, not human.
Starting point is 00:01:02 On the home side, it's a computer. So we use a tensor flow-based camera to identify catalog your property so that when you need to make a claim, there isn't much of a fuss that's put up by an adjuster. Okay. And now is it assessing more than what the object is? Or is it just like, this is a bicycle? No, no. It's actually, I mean, the value of us being a visual app is twofold.
Starting point is 00:01:25 One, you know, we're acting as a sophisticated front line underwriter, we're proving that property existed in a given time, place, and condition. And that helps materially improve our loss runs. And then for the customer, you know, what it means is that there can't be very much pushback in the instance of a claim. You have proof that your property existed. An adjuster can't come back and say that, hey, that television that you're trying to claim is actually something that's like a, you know, an inferior model or something.
Starting point is 00:01:53 Oh, cool. Gotcha. And so are your models constantly adjusting per person? So should I be photographing everything I buy? So it, again, it's just a tool for us. It's not necessarily the central tenet of what we do. A big part of it is to simplify the onboarding of getting insurance. I'm making it a bit more natural on native mobile.
Starting point is 00:02:14 Okay. And then this is kind of an interesting divergence for you because before you had a style startup, before that you were in consulting. Right. So maybe you should explain like how you ended up here because I think it's yeah. Yeah, yeah, sure. So I was a manager consultant in a past life. So I was at Oliver Wyman specifically in their financial services practice and I got a CFA at some point. I went to MIT, studied finance. So, you know, I was in their finance and risk practice. A little bit of insurance work. It was great. It helped pick me, it helped me pick up a little bit of polish the two years
Starting point is 00:02:48 that I was there. Certainly it can model things. And, you know, build powerpoint slide decks. And that, you know, that was certainly to my benefit. I, you know, I'm appreciative of the experience
Starting point is 00:03:00 that I had there. But at the end of the day, you know, I kind of wasn't getting what I wanted out of the experience. The risk, the risk of just returns to being in professional services like managing consulting or banking or private equity are great. But,
Starting point is 00:03:16 you know, because they're great, I view them as like temporary. And so, you know, I'm looking at it. I'm like in the long run eventually, like, you know, there's aversion to the mean. And I kind of want to make the jump to something where, you know, I'm building things.
Starting point is 00:03:32 I'm taking risks. And, you know, that just gelled better with my personality. So did you find that you were struggling to care while you were consulting or you just didn't feel there was sufficient upside? Well, I was learning to code while I was consulting. Okay. And so I was like, well, I'd rather be a maker of things than an advisor. Yeah. Right. And so it's fine. One of the questions I kept like percolating in my head was like, you know, they're paid millions of dollars to advise banks to do things and, you know, to improve operational processes. And, you know, I kind of wondered why the partners that I worked with just didn't build a bank, right? And I posed that question to a couple of the partners. And the answer was, hey, man, like we make a lot of money doing this. We're not going to end up taking these risks. Quite frankly, the scope of.
Starting point is 00:04:21 building a bank is way, way larger than the thing that we focus on, whether it's like, you know, in insurance context, solvency related, in the banking context, stress testing related or, you know, operational or something to that effect. Yeah. And I was like, well, I'd be the guy that wants to build a bank, right? And so I made a jump and it was kind of, it was kind of ad hoc. I, you know, we, the very first thing that I built with, Anand, who's our CTO, was actually a body scanner.
Starting point is 00:04:51 And so we use the, you know, three connect sensors, because it's like a depth sensor webcam, three points of perspective to get a body form. And we thought that we could use math, the shave away close, and, you know, use that body form to inform like sizing decisions on the internet. Yep. Right. So a super creepy thing. You know, you know, and I think if we had made a couple of logical checks before we had ventured
Starting point is 00:05:17 off to do this thing, like why aren't their body scanners in every month? mall in America. We probably would have realized that if this was something that, you know, consumers would adopt. People wanted. People, it would be there to be like a war for mall space, like mall space across America. And now, was this something that was intended to be a startup or did you just think it was a cool side project?
Starting point is 00:05:36 It was intended to be a startup. So we were left at that point. Yeah, we had left. We were pitching the gap and like a fair number of, you know, large, large retailers and brands. And so we didn't get traction on that. The technology was particularly cool. And so we stepped back and thought about, hey, like, what are we actually trying to do here? We're effectively trying to predict, you know, the sizing and stylistic preferences of our customers.
Starting point is 00:06:02 And so, you know, over the course of like a weekend, we built a super simple app where we scraped a whole bunch of like lifestyle blogger and fashion blogger content and threw up outfits in a single, like a throw up outfits and allowed people to scroll and double tap on individual parts of an outfit. So all we wanted to see that was that, you know, somebody would indicate a preference for like a blouse or like a handbag or like a hat or a pair of shoes. Lo and behold, like the activity was insane. Right. And so we were picking up users. So we eventually stepped back. We pulled it back. And then we built that something that would register the unique structural elements of individual items that people would interact with.
Starting point is 00:06:45 So like if you double tapped on like a handbag, we know like the price point, the colors. The unique structural elements. With computer vision again? Yeah. So actually it was even more rudimentary than that. We're just tagging everything by hand. It was super manual. Okay.
Starting point is 00:06:59 And so that was working. And eventually we started getting at a point where we were predicting what people would want to see next. Okay. And so with Stylekick, actually, we applied to YC like four or five times. We interviewed three times, actually. Man. And by the last time that we interviewed, we had 400,000 active users. And so our in the business was based sort of was it sort of like supply? So it was like
Starting point is 00:07:24 Yeah, it was a marketplace. So eventually what we had was, uh, were, we're designers, um, you know, uh, influencers uploading looks, uh, you know, and we were earning affiliate income doing that. Okay. And at that point, so you had 400,000 active users. Yeah. How much money were you guys making out of those? Not nearly enough. Just barely to cover our hosting costs. Uh, and the reason for that is a lot of the stuff that was being sold was was super high end. So. So, you know, back then on a four-inch screen or smaller, you know, selling a pair of $300 jeans wasn't an impulse price, you know, purchase. It was something, we ended up acting much more like lead gen to a desktop purchasing experience. You know, and in retrospect, you know, what we probably would have done a step back and looked at was actually working within that, you know, the marketplace native mobile e-commerce the things that were working like wish right so impulse price purchases five bucks or 20 bucks
Starting point is 00:08:22 where you didn't need to think twice about what you were buying yeah it was also working um you know we relied heavily on influencer marketing to grow to eventually a million active this was 2014 so it's like 2013 2013 yeah and so if we step back we would have recognized that there were a lot of these you know individual brands that were starting to stand up on top of instagram yeah and we probably could have gone the route of building built actually actually building out a fashion brand or, you know, selling, selling products of our own record. So Glossay is a great example of that. Those are the types that worked.
Starting point is 00:08:55 Either you went vertical or you went impulse price purchase. Because something in the middle was just never going to happen. Did you consider, you know, a full desktop interface where people could save and then purchase? We did. I think, you know, it's like Netta Porte and Farfetch and a bunch of these guys went that route. Yeah. I think we just ran out of steam. you know what I mean.
Starting point is 00:09:16 Okay. Yeah, of course. Yeah. And, you know, in and around the time we were running out of Steam, you know, we got to know the folks at Shopify particularly well. Craig Miller, who's a current CPO, Sateech, who's a VP, like in a GM there. And, you know, we had a longstanding relationship. And ultimately, we decided to join Shopify and run a mobile product team.
Starting point is 00:09:37 So, you know, we were there for a little under a year. We were building experimental marketplace apps for them. But we still had the itch, right? We knew that we could build, you know, really beautiful mobile products. Stylekick itself was, you know, featured in just about every market, you know, on the app store, on the part page repeatedly. We were like number one for style in like France. It was crazy. You know, we were driven millions of people through the app so you knew how to drive distribution via native mobile.
Starting point is 00:10:05 And so we started thinking about, you know, what is the next thing that we want to do? We knew we wanted to be mobile because that was one of our core strengths. We knew we could drive customers. we wanted to make sure at this point that the basic economic model worked, right? And so we built things on weekends. You know, we drive to like Northern Ontario and Miskoka and just have a couple of beers and think about what we wanted to build. So we tried, you know, things in health care.
Starting point is 00:10:34 We considered entertainment again because Natalie worked for Russell Simmons and it's kind of the impetus of us moving forward, style kick. Okay. There were a couple of things we tried. And eventually we just we settled on insurance. And the reason was, you know, we had been working with insurance brokers in the past to help us pick up policies for style kicking for ourselves. But this is not necessarily obvious, right?
Starting point is 00:10:55 Because you were in Toronto and now covers in the U.S. with a more competitive market, right? So, I mean, what really got, what convinced you that this could work? Yeah. So I think what we wanted to prove was that the pipe was big enough to drive a significantly least sized business, right? I mean, at the end of the day, it was the back of the envelope math that showed us that this could work, right? Like a single auto policy that we sell in California, the average premium is something like $1,600. Just as a distributor of insurance,
Starting point is 00:11:25 never mind underwriting or, you know, moving down the margin stack. Yeah. You know, we earn anywhere between $200 and $300 of that policy in perpetuity, right? And so if you think about what churn looks like in insurance, like a very, very good broker is churning 10%. per year, right? A good broker is turning 15%. So the LTV on a single auto insurance policy is thousands of dollars, right? Which is why you see GEICO and State Farm spend billions of dollars a year trying to acquire these customers. Yeah, because they're just massive. But you also in the beginning knew that you couldn't afford to underwrite this stuff. Yeah. Correct. Yeah, correct. I mean, so we were thinking about what's the like the capital light way of entering this business. And so the
Starting point is 00:12:09 very first version of cover was super simple, right? It was. It was. we didn't have any licenses because we weren't selling any insurance. We didn't know anything really about insurance distribution. It was just a handful of views leading to a camera view with a preamble that said, take a picture or something you want to insure. That's it. And we launched it and we used the methods that we used to grow style kick to grow cover. You know, we ended up being the number one ranked insurance app in Canada the second day.
Starting point is 00:12:34 And during YCE, we were actually like two weeks into launch. Like we were featured for like under the best new apps in the United States, right? Again, we didn't have any insurance licenses. Like, we didn't know anything about insurance. All we could see was that every 60 seconds we're getting an insurance request. Right. So how did those conversations with investors go? Because I think you could, yeah, as just a distributor, I think a common pushback would be like,
Starting point is 00:12:58 isn't this just like running to zero margin? Yeah. So I think like any pure lead gen business is just relying on a marketing arbitrage to continue to exist. And there are lots of examples of that in insurance. I don't think that you can build a durable business. is just a lead gen, you know, a lead gen service for a couple of reasons. One, those arbitrage opportunities eventually dissipate. The second is you're not building any brand like equity or value and you're certainly not,
Starting point is 00:13:25 you know, doing your customers of service by vacuuming up their contact information and selling it on 10 times to juice, you know, average revenue per user. Right. Especially as a startup, a venture back startup. Yeah, yeah. And so we were like, well, we knew exactly what we needed to do. We were like, okay, well, we need to start owning like the actual. customer service, like the selling experience and eventually more, right? And so during YC, we're like, okay, well, we're committed to getting licensed across
Starting point is 00:13:50 the country. We're committed to getting as many insurance markets as we can on the cover platform so that when a customer comes in the door, irrespective of what it is, they're looking to cover, we're a competitive place. And so we stood up a national insurance brokerage in under 12 months, right? So we were in 49 states with 30 carriers in under 12 months, which is, I think, enough to show that, you know, we could de-risk ourselves from an execution perspective, because that's a non-trivial thing to do. Sure. And so how much did you have to raise to
Starting point is 00:14:21 accomplish that? So that was YC. So if you're in winter 2016, so by winter 2017, you were in that position. Yeah. Right. And so post-demo day. I mean, we raised 3.2 million bucks at Demo Day. So some of it before Demo Day, a lot of it after Demo Day. We actually had most of our seed rounds still when we raise our A. And a big part of it was we knew that there was going to be a ramp. So we didn't make our first hire for probably the first year and a half, right? We knew that it would take a little bit of time to get everything tooled before we could start to scale. But yeah, we raised our A as soon as we were in a position to be able to be selling insurance business.
Starting point is 00:15:00 Okay. And so when you raised your A, did you feel that you had product market fit? I mean, if you take a look at our reviews. Reviews or reviews? Reviews. Like for cover, I think we do. I mean, we do everything we say we're going to do, right? You know, a customer comes into the door.
Starting point is 00:15:15 We make the underwriting application process super simple. You know, we do not spam our customers with phone calls or emails. Every single one of our customers gets a dedicated text line where they can text us back and forth to ask questions. It's a truly like, I think millennial first experience, which is a cliche thing to say, but it's like the thing that we do. So, yeah, I mean, like we do what we say in doing well because of it. And so when it comes to growth, you guys just raised a B in 2018.
Starting point is 00:15:49 Correct. It's still compared to Geico, you know, nothing, like a tiny amount of cash. Yeah, no, we have, I mean, there are other insured tax that have raised hundreds of millions of dollars now, right? Yeah. Still a drop in the bucket, well, in the insurance market. There are $500 billion in insurance premiums that are written just in the property market in the United States every year. Right. And so look, like that's sort of concern to us because, one, we don't take balance sheet risk yet. I mean, eventually we may be because we can be pretty opportunistic about the types of requests that are coming in and whether we want to stand up products for those.
Starting point is 00:16:24 So, yeah, in practical terms for people, our insurance. What does that mean? That means that, like, if we see, if we see a lot of customers who are coming in for a specific thing, right? Like maybe it's home or maybe it's auto in a given geography and we're writing it profitably. We should be, we can actually just step in and underwrite the business ourselves, meaning that we take the risk or we price the risk, take part of the risk and sell the rest of it on. Okay.
Starting point is 00:16:49 And if we take any risk at all, we need to hold the capital and reserve to be able to take that risk. Right. Right now we do not. Right. And so which is why we can, we can be fairly capital light. And so focus mostly. on, you know, the distribution aspect of the business and acting as sophisticated front line underwriters, right?
Starting point is 00:17:09 So we're being actually pretty prudent about the types of risks that we do send to our carrier partners. Okay. Yeah, I mean, you can think of insurance as three discrete businesses, right? Like distribution, which is a business end of itself, underwriting, claims servicing, and, you know, regulatory overhead. Folks who are attacking, you know, every aspect of this at once are probably not going to get any. of them right and burn a lot of money right out the gate. And those are the folks that have tended to raise hundreds of millions of dollars to get to that point. I think our goal right now is to make sure that we're continuously iterating on the best possible front end experience,
Starting point is 00:17:48 making sure that we're proving out that the product of self is a good way, a mechanism to filter out bad risks. Yeah. And then move into underwriting and maybe the rest of the stack. Okay. Yeah. Gotcha. And so how does your lead gen work now? Yeah. We acquire exclusively through your apps. So the app store of Google Play. Really? So just highly rated. So it's all search. Yeah. So I mean, yeah. So we were the beneficiaries of like pretty decent ASO very early on. And we run a lot, we run a lot of paid. But we take a generally speaking like a portfolio approach to growth, right? So, you know, like you, we would acquire via all the channels you expect, Facebook and Instagram, Reddit, like what have you. We're good at ASO. We're starting to buildup cover.com.
Starting point is 00:18:32 that'll probably be a fair material entity for us. Yeah. And then we build things that are like what we consider be pre-insurance, right? And so these are tools that we think are useful to our customers, irrespective of whether they buy insurance from us right away or not. Yep. A good example of that is like in the cover up, price drop alerts. You don't have to buy insurance from us.
Starting point is 00:18:54 What we can do is just programmatically remarkets you. Every time we see like a violation fall off of your record, you know, or a claim fall off of your record. or you're coming up for renewal. That's a service you don't need to pay for, but it's pretty valuable because you don't have to think about it. Yeah, that's pretty good. Another example is, you know, for certain markets,
Starting point is 00:19:13 we're giving away access to a defensive driving school, right? So if you go to driving.com, you know, give you a very stylish example. In Texas, you know, if you go to a defensive driving school, you can get a violation knocked off of your record or get access to an insurance discount, right? So it can be material. It can be like 10% of that. the overall premiums. We're talking about hundreds of dollars, right? Usually those things,
Starting point is 00:19:37 like there are entities that charge anywhere from like 25 to 150 bucks to go through that course. It takes like a couple hours. We're a technology company. We just build it and give it away for free. And so, and that can be funneled directly into our products. So, you know, in Texas, there are like 480,000 people, you know, over the course of the last 18 months that went through a defensive driving school. Just in Texas, right? And so it's like, if you think, If you think about, like, hey, where can I be? Like, where are my customers? And how could I build product to, you know,
Starting point is 00:20:09 facilitate a transition of those customers from those sources to the actual, the apps? You can build fairly durable distribution. And were you thinking about these kinds of programs when you're in YC? Or is this just by talking to your customers, figuring it out all the way? I think it was observing the types of things that, like, you know, folks were asking, like, do you have a defensive driving discount? Yeah.
Starting point is 00:20:30 They will literally ask us, do you have a military, discount. Do you have this? Do you have that? And we're like, oh, maybe we haven't considered this and we should go build something to support this. The other thing I do is like I read a lot of insurance rate filings. And so it's a weird thing to do. But I get to get a fuller appreciation of the way that one, the filings are structured, but also discounts that are generally speaking available to our customers. And how we can build product to make it easier to access those discounts. Right. And so, yeah, when someone might be. might be shopping around.
Starting point is 00:21:04 They're going to start comparing these things. And this fringe benefit might matter a lot to them. Yeah. Yeah. I mean, Geico, for example, has this weird, you know,
Starting point is 00:21:11 affiliate discount where if you own a share of Berkshire Class B stock, you get 8% discount on Geico, right? Really? Which is crazy. Yeah. Well, there you go. Now you know.
Starting point is 00:21:19 Man, I should take advantage. Okay. Just pop up in Robin Hood. Yeah. So, so you mentioned cover.com, and I forgot to put this in my notes,
Starting point is 00:21:30 but you guys just bought this domain fairly recently. right. Yeah. So we've never talked about this on the podcast, but you spent a lot of money on it. Yeah, and I got all that crap for it too on Hacker News. Really? Yeah, yeah. I mean, look, like, um, the crux of it is like, what's the ROI on buying, you know, something like that? Yeah. Um, look, it, buying a very expensive domain is not going to make or break our business. Like, because we bought cover.com does not mean we're going to be successful. It also doesn't
Starting point is 00:21:57 mean that we're going to fail, right? We're going to, we would fail if we did something fundamentally wrong or, you know, continue to be. build on something that didn't have product market fit. We know we have product market fit. People buy our products. People spend thousands of dollars with us. So from my perspective, it was, hey, look, right now we're super surgical about how we acquire, right? Like, we have to be because you're capital constrained. At some point or another, we know that, like, in equilibrium, we are competing on general awareness, right? We're in the trust business. And any minor change, right, in conversion, given super high LTVs, is going to make a huge impact, right?
Starting point is 00:22:38 If you have a $2,000 LTV and conversion moves up a couple bips, or up or down a couple bips when you have tens of thousands of people coming through every single day, the domain pays for itself, right? Very, very quickly. And so, you know, outside of that, if we're competing on general awareness, yeah, we care about discoverability, right? That matters. We care that we're discoverable, you know, and we own like one of the more common words in the English language.
Starting point is 00:23:05 And so, in other words, you would say if you have the cash, do it. I think it's on a case-by-case basis. I think if it makes sense for your business, and you have to have like a very good sense of what the underlying economic model is, right? Like we can do the sensitivity analysis. It's like minor changes in conversion and how that eventually affects the bottom line for us. Yeah. And for us, it's like, if we're writing a million policies a year, it's going to actually take
Starting point is 00:23:28 like a couple thousand policies, like less than a couple thousand policies to pay for this. Because it was 900, roughly. So we paid $750 for it. And then there were broker fees. Okay. Got you. Do you have any pro tips? It's a, I mean, look, like the guy that we worked with, if you're actually considering, you know, buying a domain, who's great.
Starting point is 00:23:49 You know, he's a professional who's introduced to us by Arjun, set the tribe. It's like on our board. our lead investor. But a lot of the folks in this space are super shady, right? You should be pretty careful. I would recommend using a broker irrespective of the general shadiness. You know, the initial bids that we were getting were in like the million and a half to $2 million range, right?
Starting point is 00:24:14 And I can guarantee you that if we had tried to buy it after our B or our C, we'd be looking at like $5, $6 million. Right. Okay. So did they know it was you? No, they didn't. Okay. Yeah.
Starting point is 00:24:25 We had a broker who proxy through. another broker. Really? So that... Yeah, because I've heard about people who own many, like, of these big TLDs. They will only work with the customer. Yeah. Yeah.
Starting point is 00:24:36 I mean, you know, I think we were lucky enough to have network access, right? Yeah. It's not necessarily afford to everybody, but it saved us a lot of money. Okay. Yeah. That's great. So to go off on a tangent a little bit, you are engaged to one of your co-founders. Yeah.
Starting point is 00:24:54 Yeah. Right. So I got engaged in now. who heads up all the product at cover when we were at Shopify because we were thinking that we would be there for a while. Okay. And this would be a little bit more stable than, you know, the ups and downs of working for a wedding.
Starting point is 00:25:12 You can budget for a wedding. Yeah. Given how Shopify stock is done. Yeah. Yeah. So we were at Shopify. We're like, okay, this is going to happen. Like, we'll plan the sale.
Starting point is 00:25:23 We have some time now. Yeah. Then we apply to YC, right? And so we were like, oh, okay. For the fifth time or something. Yeah, we've been rejected so many times. Like, what's another time? And so we applied and like, you know, we got in, right?
Starting point is 00:25:38 And it was like a basic prototype. We didn't have any users really, which is, I guess, the way the world goes. And then like two weeks later, we flew from Toronto to California, right? And used Zeus at the last minute to get some housing. Yeah. And since then, it's been a roller coaster, right? Because we've, you know, we did YC, raised our seed, started scaling a team, building up the business.
Starting point is 00:26:01 And it's been a pretty aggressive run. We're probably going to get married this summer. Okay. Congrats. Yeah. Very exciting. And so how do you manage that relationship, you know, because they're obviously, you know, relationship tension, co-founder tension.
Starting point is 00:26:14 And then you have to deal with, you know, employees at the same time. Yeah. Yeah. I think like, look, co-mingling professional and personal risk, like, especially if you're starting a startup. up. I mean, it's not necessarily a recipe for success, right? To be quite frank, I think we're the beneficiaries of having worked on two businesses together now being acquired into Shopify and working on the same product team, right? And there's like a clear division of, you know,
Starting point is 00:26:44 the scope of responsibility of role. She was, she, she's an exceptional designer. She's an exceptional product person. She got, you know, style kick and cover featured on the front page of the US App Store simultaneously, which I think very few people like Havette can have claimed to. And I trust her completely to take care of that function, right? I work on the rest of the business. So I work on the insurance aspects of the business. I'm thinking about what do we need to do to continue to deliver an exceptional product experience. So what products should we be standing up? Who should be, we should be working with. They're very different roles, right? So that helps a lot. But I think it's been a net benefit, right?
Starting point is 00:27:25 Because the cohesiveness of our co-founder team, I think, is like not, you know, it's pretty atypical. You know, Ann, I went to high school with Natalie. I'm engaged to. Ben was our first hire into style kick. And so we've been working with him for six years, right? That helps a lot. Yeah. And it's like, one, the strength of that core team because they're all, you know,
Starting point is 00:27:51 awesome of what they do. It's helped us hire very well. And when it comes down to the actual tactics that you use to make sure the relationship, you know, the conflicts will obviously happen, but it doesn't implode. Like what are the tactics that you use? Yeah, yeah. I mean, like eventually you feel out, you know, with your partner, what you need to do to de-escalate, you know, you will know what buttons you can push and you shouldn't be pushing.
Starting point is 00:28:18 And you, you know, you step back and you realize that you're on the same. team. And that helps, certainly. Do you have to put any rules in place in terms of, you know, like living together or working together? I don't think there are no hard and fast rules. Actually, our co-founder still live together. Oh.
Starting point is 00:28:33 Yeah. Wow. So, I mean, we're as tight as you can get, I think. Yeah. Okay. So now that you guys have raised your series B and, yeah, are quite large, you have two offices. So you have the Toronto and you have your San Francisco office. Yeah.
Starting point is 00:28:49 as the CEO, how do you manage that and how do you make sure everyone's kind of on the same page? So, Anand is full time in Toronto. Natalie flies between the two offices. I mean, most of the products that's in Toronto. We have some senior engineering in San Francisco. Sales lives in San Francisco. Insurance operations lives in San Francisco. So, I mean, the folks are like running their respective functions are where their teams are. And then I make an effort to be wherever we can be.
Starting point is 00:29:18 And we run these off-sites. Like we're heading to Vegas next week. Okay. For the entire, the entire team will be together. Okay. Yeah. So, again,
Starting point is 00:29:27 division of labor, we invest, we've invested in Zoom rooms and like very high quality, you know, AV equipment to make sure that, you know, at least communication is a solved problem.
Starting point is 00:29:39 Okay. And in terms of culture, how do you keep people on the same page? Yeah. So that's interesting. I mean, actually, I think the cultures are,
Starting point is 00:29:45 the individual cultures are pretty different, right? Like, like one is very, product oriented. And we have a sales office in San Francisco that's like super rambunctious, right? I actually don't have a problem with that, right? As of this point, I think what my job primarily is, is to make sure that we're all aligned in what the ultimate goals are for our organization, right? And we're trying to build out a fair and sustainable insurance entity at the
Starting point is 00:30:10 end of the day, right? We know what we need to do. We need to make getting insurance easier. We need to make it fairly priced for individuals for whom it should be fairly priced. We need to be in around when claims are being made and help facilitate those claims so that our customers have positive experiences around that because that's the ultimate function of an insurance company. Right. And yeah, effectively act in that advisory capacity and scale that across just about any line of business. Okay. And insurance that we can. That makes sense.
Starting point is 00:30:38 And so as an international founder, we have a million questions coming in from Twitter all the time. It's like, oh, how do you deal with this as an international founder applying to YC? You're doing YC or post YC is actually, I think, the most common place of anxiety where people are like, I think I can figure this out in a three month term. Longer term, what is your advice to those people? Like, how do they make it work? Yeah. So look, like, we were all in San Francisco and decided to open a Toronto office, right? Because we know the market.
Starting point is 00:31:10 We knew where to look. we have a pretty good, and it's a super high quality team, right? That decision we made concertedly because we had an edge in doing that. I mean, if you're talking specifically about, hey, like, if I'm an international founder, should I stay in the Bay Area or should I be somewhere else? You know, my objective opinion on that is this is the beating heart, right? Like, this is the beating heart of everything technology. And you should have a presence here.
Starting point is 00:31:36 Absolutely. If you can get your visa issues resolved. Yeah. I mean, even we had issues. Like, Anand was stopped at the border like three times, turned around. We had to get them at 01, which is kind of ridiculous. But that stuff happens. You just have to work through it.
Starting point is 00:31:49 Yeah, it happens to everyone. And it's just like, you make it through. But obviously, neither of us are lawyers. Yeah, okay. Consult. So the new batch is starting. Yep. You guys haven't been out for that long, winter 2016.
Starting point is 00:32:04 So it's in recent memory still. What advice would you give to the people just entering the batch? Yeah, so actually I ran a SARP school batch, right? So there are in a couple of the companies that were in my batch for now in YC. And certainly, like, I've been doing this for a little while, like, which is like pre-coaching folks who are running in YC. One of the folks, the first folks I did it for was Austin at Lambda School. Okay, cool. And I ended up being like one of the first investors.
Starting point is 00:32:30 Give me the opportunity to be one of the first investors in Lambda School, too. Look, I think the core advice that I give is actually not that different from what YC partners. give, right? It's like, hey, pick a KPI, make sure you're growing that that KPI. You know, everyone implicitly knows that a couple inches deep into your startup, everything is held together by duct tape and glue. The bet that folks are making on you is that eventually you're going to figure it out, right? So go into it with that in mind. Make sure you hit your KPI and you talk about it, right? Because it's important to actually talk about your successes. And then outside of that, the typical advice, you know, is don't hire anybody,
Starting point is 00:33:13 because you shouldn't be hiring anybody. Don't go to conferences or parties that are not directly related to the KPI. So if it's going to make you revenue, if you're going to build revenue doing it, fine. But otherwise, don't be doing it. And otherwise, like, don't get distracted. This is like a three-month, like, sprint for you to truly accelerate what you're doing. Yeah. And either get to, you know, why? C is like forcing a function, right? It's like if you're, if you're not, if you don't have product market fit, it's going to help, it's going to help you determine that you don't have product market fit pretty quickly. And if you do have product market fit, it's going to be like, okay, fine. It's an accelerant. Yeah. And what about post YC? I know, I know there are many companies who kind of go through a lull and they need to decompress for, you know, a week or something. Yeah. But how did you guys find your rhythm again? Yeah, I think, I mean, we're the, we're the beneficiaries of having done this a second time. So the ups and downs are not as aggressive. Right. Like the highs are not as high, the lows are not as low. And so we kind of just kept our heads down. All the lessons we learned from the first time around were compost. Right. And so we could, we have to put a pretty good cadence of just making sure we're hitting our goals. And communicating that to investors, just why we raise an A pretty quickly, right? But yeah, you just, you keep doing what you were doing during YC. You should be okay. Okay. Yeah. Cool, man. Well, this has been great. Thank you so much. Yeah. Thanks for having me. I appreciate it. All right. Thanks for listening. So as always, you can find the transcript and the video at blog.wycombinator.com.
Starting point is 00:34:41 And if you have a second, it would be awesome to give us a rating and review wherever you find your podcast. See you next time.

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