Connecting the World: The pop.in Story with Alex Kruglov

Jake Aaron Villarreal: Welcome to our podcast, From the Ground Up, where we interview startup founders exploring their journeys, their success, challenges, and lessons learned. We hope you be inspired in discovering what it takes to build a thriving startup. I'm your host, Jake Aaron Villarreal, and excited to have with us today Alex Kruglov, founder of pop.in. This is an LA-based startup which has raised $7 million in funding. Alex, welcome to the show.

Alex Kruglov: Hi, how are you?

Jake Aaron Villarreal: I'm doing great. Well Alex, let me give you a little, audience a little background of you, and um kind of we'll set this up and get into really why you're here to talk about your company. But just a little background on Alex. He graduated magna cum laude from Brown University, received his MBA from Harvard University. And he has been part of the tech industry for some time. Uh he was at Hulu for six years that helped launch um, uh their basically their launch team, overseeing all of its content acquisition efforts for nearly 500 content providers, including every studio and major network in the US and most major television and film companies in Europe, Asia, and Latin America. He's a three-time entrepreneur and here to talk about his company today, pop.in. Alex, um before we dive in and start talking about your company, tell us a little bit about where you're from and how did you get into technology?

Alex Kruglov: I was actually born in Ukraine, uh which uh was still at the time part of the Soviet Union. And I moved to the States when I was a teenager, moved to the Boston area. And when I first moved to the States uh I didn't speak English. And uh the way that I ended up not only learning English but also kind of becoming an American teenager was through pop culture. So I became an obsessive consumer of music, TV shows, uh watched movies when I could afford them. Um saved up money to subscribe from my paper route, to subscribe to Rolling Stone magazine. And so um, for me pop culture was not just a way of enjoying uh entertainment, but also as a way of kind of uh joining a community and becoming a part of uh the American fabric uh if you will.

So I, you know I uh, from from a very early sort of age of you know being a '90s teenager, I was quite focused and obsessive about somehow being part of that world. And I had no idea how uh because I wasn't a creative uh per se. I wasn't a musician or a rock star, I wasn't going to be the next Tom Cruise. And um, and so the, when I went to college uh in the late '90s, early 2000s, uh one of the fields I studied was computer science. And I kind of realized that right at that time when Napster came out it became reasonably clear, maybe not to adults but to teenagers, that the intersection of the internet and technology was going to be the future of how creative storytelling was going to um sort of be dissipated to the world. So I became um quite focused on the, sort of that intersection of tech and media. And effectively um other than a stint uh at McKinsey & Company, which is where I started my career where I was just kind of just gener-, generally educated in business uh in six countries around the world. Other than that I've essentially spent my entire career at that intersection of media, storytelling uh and technology.

Jake Aaron Villarreal: You know, storytelling is such a big part of technology. Uh you have to go and create a product, pitch it, present it, solve a problem, and you're telling a story all the, all through that process. Um when you got into Hulu and you joined Hulu, what was it that made you I don't know, excited or I mean, how did that even start? How did you get connected with Hulu?

Alex Kruglov: I was, so I was uh I, I had uh, I'd been involved in two different startups that I found uh when I moved to LA in 200-, uh permanently in 2006. But I started spending a lot of time in LA starting 2004. And they were kind of uh uh, they had played out, uh played their course. And I felt like I was a little bit of an impostor in that I had never actually worked in the industry that I was kind of going after. Uh so I got a job at Sony Pictures working in television. And at the time I was thinking you know what, I'll spend a couple years there, try to learn as much as I can about how, and then I'll bounce out and you know and, and join a startup or do something else. I also worked at Fox Searchlight briefly. And um, that future that I was kind of hoping for happened a little bit sooner than expected.

Um I was uh, I was connected to uh uh gentleman named Jason Kilar who was the CEO of Hulu. And um he reached out and we started talking about the possibility of me joining his team. Which at the time it wasn't called Hulu yet, and it was just essentially an idea around this idea of watching premium video, video uh on the internet. And the job that I ended up getting, which is running content acquisition, was one that I was imminently not qualified for at all. Uh but no, the, the, the sort of the good news for me at the time is that technically nobody was qualified for it. Because Netflix as we know it today didn't exist, and there's no such concept as licensing uh uh uh uh licensing television and film for distribution on digital. And Jason had this strong bias at the time to not bring in industry experts because they had a specific way of doing things, and he wanted to invent a new way of doing it from scratch.

And so I happened to get very lucky in that I was, I had a little bit of experience in entertainment, like a few months' worth, uh, and I was a general athlete who had been an operator who understood technology and who had some business background. So I was you know I was very fortunate to kind of be uh, not just uh, to kind of end up in a place that worked out but to also be there at the right time. Which was 2007 when I joined uh, when I joined Hulu. And it was an exciting ride because it was you know, the first place that I had been where we had a vision for uh a consumer offering um that no one else agreed with. The, the nickname for Hulu at the time was "Clown Co." And then you know 6 to 8 months later, where I used to have to spend you know three, four minutes explaining what I did, all of a sudden uh most people that I would be talking to not only had heard of Hulu but consumed it. Uh the, the funniest I remember, about three or four months in I was talking to a friend of mine and he is Canadian. He was saying that that's the place where he watches hockey, which was totally not, like it was a complete afterthought for us at the time. But that felt like something was happening.

Jake Aaron Villarreal: That's great. Now when Hulu launched and became a streaming application and provider, how far along was Netflix and was that a target that you were looking at as they were building a service and a video content appli- location that kind of was I don't know, in the same vein that you were building? Or kind of how far after did Hulu come around?

Alex Kruglov: Netflix had been around for a long time as a DVD by mail uh service. Uh and at the time when Hulu launched, Netflix was starting to dip its toe in the water by having some of their movies available uh on a website uh for free to subscribers. So it wasn't an extra cost, it was just kind of a, an extra benefit that they threw out uh there. We as the team at Hulu were deeply aware of it and we looked at it very closely, but the, our uh the money behind Hulu uh and the media companies that were involved with Hulu were not concerned about Netflix at all. Uh their focus was on piracy, which at the time was a really big deal. So there's a bunch of stuff that nobody remembers, but there were uh pirate sites like Pirate Bay and Mininova that were very popular, lots of people were downloading uh um downloading HBO shows and, and stuff like that from there. And uh Google had just bought YouTube and there was a real concern that uh potentially YouTube was going to become the home for premium entertainment you know without there being proper compensation uh for the media companies. So Hulu was really um founded with a focus on that. And remember at the time you're saying application, which you, we use that term too, but nobody thought that at the time. It was just a website, there were no mobile devices, there was no iPhone, uh you know, and certainly no desktop devices, no sorry excuse me, consoles or television devices where you could watch video. All of that came later.

Jake Aaron Villarreal: Makes that's, makes a lot of sense. It sounds like it was almost like a startup within a bigger company, that you were building something and paving a path. Um you know with really no...

Alex Kruglov: Arguably, arguably the reason Hulu worked was because it wasn't that. So it was a joint venture between two media companies, but it was set up as a separate thing with separate funding. So we had our own office and we had a board of directors, and we had an outside investor that was like, like a VC type investor, a private equity firm called Providence Equity Partners. And for the first three years, we were really set up to run as an independent venture that was not governed by the media companies. And I think that if that hadn't been the case, we wouldn't have been able to um uh to kind of uh uh start out the gate the way we did. There was also interestingly enough there was also a writers' strike back then, which people don't remember as much now but just like there is today.

Jake Aaron Villarreal: Yeah, that's crazy. It's all about content. Uh um, you had some startups uh before pop.in. Um three mentioned, maybe more than that. Um kind of give us a little flavor of the type of startups you, you had built. Did you have any acquisitions and kind of give us a little bit more context there?

Alex Kruglov: First startup was when I was uh in college, uh I was a co-founder uh with a couple friends of a, of an online magazine, uh an online photography magazine. This is back in the late '90s. Um it uh, it was uh uh very early, uh and the idea of consuming a magazine online was very kind of strange uh for people. Um but, but uh uh it was called Glimpse magazine and it ended up uh running for about eight or nine years and [was] acquired by National Geographic uh eventually. Uh so I did not stick around um after college because I didn't grow up with any wealth or any money, so it was very important uh to get a job that paid the bills and had health insurance uh after college, especially because I have a chronic uh illness. Uh so that was the first, that was the first uh startup.

Um I, uh uh my second one was a media company where our biggest uh uh contribution to humanity if you will was uh a hip-hop musical, uh the first ever to move to Off-Broadway. And the feedback that we, it was a big hit in LA. And then when we moved it to, to New York, the big feedback was that nobody would ever see a hip-hop musical in New York. Uh so, uh so this is my second time being a little bit too early uh to something that sort of ended up working out uh uh, great success you know, some number of years later.

And then my third startup was a uh uh, the vision behind it was to acquire rights to TV shows and movies from around the world for digital distribution. The problem at the time was not only did, did, had Netflix not launched and Hulu certainly not launched, but even Apple uh with iTunes only had a music service. So we got the rights but there was no revenue and no consumers at the time. And then ironically 18 months later I was on the, I was the buyer of the exact same business plan. So I literally shared my business plan with the companies that we were dealing with who were basically doing the exact same thing uh 18 months later. So Hulu was the first time where... and it wasn't obviously, I wasn't the founder of Hulu, I was just kind of there early, but it was the first time where I saw an idea that felt like it was a little bit ahead of its time land at the right time. And so timing was definitely a thing uh that uh I experienced at Hulu which uh timing and luck uh in addition to a great idea and great execution, which is a crucial ingredient uh to, to startups.

Jake Aaron Villarreal: Yeah, timing is essential for almost everything in life, but specifically with startups and funding and going to market and finding the product-market fit, all those things. Timing is critically important. It's good to be ahead of the curve, not too far and not too, not too far, that's right... late.

Alex Kruglov: Yeah, yeah, certainly not too late, yeah.

Jake Aaron Villarreal: Talk to us about pop.in. Um this is your current company today. It's been around... we call it a startup, it's been around for seven, eight years, is that correct?

Alex Kruglov: Yeah. So we first started a company called Smiletime. And uh it ran uh for about five years. Uh it was [a] competitor to Twitch uh with a slightly different value proposition. It was uh you could call it a different startup, uh but technically it's the same company. So we you know we pivoted and started pop.in. Uh Smiletime was in the interactive live streaming business and pop.in uh came... uh so, so that did really well and kind of ran its course. Um and we worked with a number of different uh media companies, uh uh studios and creators.

Uh whereas with pop.in, our goal was to create an ecosystem uh for consumers, and specifically an ecosystem that allowed humans to connect with other humans without there being uh production involved and without there necessarily being influencers uh at play to kind of facilitate uh the human connection. Um we had experienced elements of it with our previous uh uh startup Smiletime, but our goal with pop.in was to figure out how do we create it at scale and how do we do it uh in a way that is repeatable. Um and we realized that the kind of games that people play together in groups uh at game night uh with friends and family, scale themselves to uh an experience that welcomes uh human interplay without there being pressure on conversations or politics or toxicity or any of that stuff that, that sort of permeates online exchanges.

So the thing that we had to solve for was, one, distance. So how do you create an environment where people feel a sense of presence without being at the same room at the same time, um which you and I are doing right now. Uh and then the second is, how do you get strangers to feel comfortable engaging with other strangers reasonably quickly. Um and that's basically the vision behind pop.in. So it's essentially, it's a gaming platform that where people play uh games together in groups. So it effectively functions as a real-time uh social network where people play with existing friends but where they also make new friends, and essentially create matchmaking environments where people you know, get so close on our platform that you know, we know they take vacations together uh in the real world even though they live uh you know half a world away. So that's, that's basically the vision and the execution behind pop.in. We call all of that "joyful togetherness."

Jake Aaron Villarreal: That's great. You know when you started the first company, Smiletime, and then it evolved, was there a point where you said it ran its course, where you had to make a change? You know, was there a pivot there? Was there any sort of a, you kind of saw the writing on the wall of the current product and the landscape and it was time to look at something that was maybe different? Walk through that.

Alex Kruglov: Yeah, it was definitely a pivot. So we saw some success uh and we saw... essentially our you know our vision behind launch for Smiletime was to launch it uh as a, what, what we you know what you were referred to in business as a B2B2C environment. Meaning we partnered with businesses to launch [a] direct to consumer offering powered by Smiletime. But where the push and might was behind big companies like the CW Network and TMZ that had large audiences and had resources and production, they could pay us and all that good stuff. And uh, and we had some really strong uh out of the gate success. And then as, as it continued we realized that we wanted to become a direct to consumer company, and not just power and empower other businesses. And essentially as we were trying to create that transition, the world of live streaming outside of games (which, which, which Twitch owned) was quite nascent. Um and so once again we were a little bit early uh in a space where you know you saw at scale those kinds of experiences work in China, in Korea, in Japan. Whereas in the US, you saw some live shopping here and there, uh you definitely saw a lot of live streaming for games, but you didn't see a lot of day-to-day uh live experience that was interactive pre- uh pre-COVID.

Um and so we essentially were seeing that we could make a choice. We could continue going down the B2B path uh and essentially become a partner to studios, networks and creators. Uh but that was a business that candidly, we, the founding team was not all that excited about doing indefinitely. Um or we could pivot and do something else. And we decided to go with the latter choice. And candidly it was because if we hadn't, we probably would have not stayed together as a team. And you know, doing something together that motivated all of us was a huge priority uh at the time. So that was the motivation behind it.

Jake Aaron Villarreal: That's great. Yeah, every company seems to have to go through a pivot at some point, whether it's early or later in stage of their company. And there's unfortunately not a, a playbook that walks you through how to do it. So what are some of the lessons you've learned in having done that pivot and maybe other pivots that you know, the listeners might gain some insights from you on?

Alex Kruglov: For sure, made a lot of mistakes uh as well. So the, the biggest learning for me is if you feel you're going to cut, cut early uh not late. So the earlier you do the pivot, the better off you are. Uh the simplest reason is because you want to have money in the bank to continue being able to operate. Um I heard somewhere, so this is not my quote, I didn't come up with this idea, that there are only two reasons that startups ever uh uh finish. And one is you run out of money, and two is the founders don't get along. Um and, and that really kind of resonates. Now of course you know, the reason the founders don't get along or the reason you run out of money is because the startup wasn't working. But from a technical standpoint those are the two, the two kind of reasons. And so you want to avoid both as much as possible. So you want to have uh disagreements among the founders, but you want them to be creative disagreements, you don't want them to be "kill the company" type of disagreements. And then you want to be able to continue paying salaries because without it you won't have the folks that are doing the work.

So we've, so that, when it comes to pivoting, the biggest learning definitely is to try to you know, still have a little bit of money in the bank to be able to build the new prototype of whatever you're building, so that your investors come on board. The thing we didn't do is we didn't recap the company. In retrospect it might have been a good idea to have done that, but I'm a you know, reasonably loyal person. And I felt a sense of loyalty to my investors, and I wanted them to be able to benefit from whatever upside we created. So you could, you could call it a learning, you could call it a, you know, you could look at it both ways, but that's the thing we didn't do.

Jake Aaron Villarreal: Got it. I want to go back to that. You talked about recapping the company. For some investors, what does that mean?

Alex Kruglov: So you know there's this concept of a cap table, which stands for capitalization table. Cap table is uh is you know who owns the company, uh and it's split between uh the founders, the employees, and of course the investors. And the more money you raise uh from investors, the more uh the larger percentage of the company the investors own. So if the investors invest in Company X, and then Company X says, "You know what, we're not going to do that anymore," then the typical way that you go about a recap is to do one of two things. You either say "we're gonna shut down Company X and we're going to start Company Y, and then you're welcome to invest in Company Y. But if you don't, you know, that's it." And of course you open yourself up to potential lawsuits and stuff like that uh from investors if you were to do that. Another way to do a recap is to say "from now on we're going to issue a bunch of new equity that will essentially dilute uh the existing investors, and then existing investors have the opportunity to buy into the new company under, you know, under the new equity structure, or not. And if they don't, they don't believe in the new thing, then you know they essentially get washed out. And if they do, then they get you know, then they get a piece of something new." This is what the most famous example of this was when uh Twitter pivoted away from a company called Odeo, which is a, which was a podcasting business which wasn't working because they were too early to podcasting. And when they became Twitter they essentially recapped the company and washed out a lot of the Odeo investors.

Jake Aaron Villarreal: Yeah, we invest in companies too, we just, we were part of one of those recaps. So I, I understand it. But it, it's uh, it's not great from an investor standpoint.

Alex Kruglov: No, you don't feel very good about it, but you want to still have some, you know, some ownership in the, the future of what that could be. So you're kind of in, in between a rock and a hard place.

Jake Aaron Villarreal: Uh yes.

Alex Kruglov: I do have investors now that you know, that invested you know seven or eight years ago and that barely even know what we're doing because they're you know individuals and it wasn't a very big check. So it's kind of interesting to sort of you know keep updating them as to what we're up to and stuff like that. But thankfully you know, we'll see what happens.

Jake Aaron Villarreal: You talked about uh getting along with your partners as potentially being one of the issues that can stop a startup. How many partners do you have today and have they been with you from the beginning?

Alex Kruglov: Two co-founders um of pop.in. And they've been with me from a large chunk of, of Smiletime, uh and definitely you know they, they conceived, we conceived pop.in together. Uh one is a gentleman named Rory McKenna, he's our Chief Technology Officer. And the other one is Alex Jao who is kind of a jack of all trades, but our Head of Product.

Jake Aaron Villarreal: Yeah, that's great. It's, it's hard to find partners. How did you find your partners?

Alex Kruglov: So they were not the co-founders of Smiletime when you know the original, the original Smiletime. But they were uh, Alex was one of my very first hires, and Rory was uh, uh was you know reasonably soon after. The, people talk a lot about culture fit. And to me that's a little bit of a nonsensical statement in the early days of a startup. Because by definition you don't have a culture, you know, you just have a vision and you want to be able to build a team. And my general perspection, percept-, perspective from a hiring standpoint is that I only want to hire people who are at least 10 times better than me at the thing that I am hiring them to do. Uh so I couldn't do their job. Um and, and they can't do what I do, but the thing that they do, they have to be you know dramatically better than me so I can learn from them. Um uh Mark Zuckerberg has this line uh that I like but don't quite uh don't quite agree with. Which is that you want to be able to work for the person who you hired to work for you. There's something there, but that assumes that you're essentially doing the same thing. Whereas I'm a big believer in hiring you know 10x uh engineers, 10x product people, 10x designers, u- 10x marketers you know, whoever it is for the role. Uh so that they can feel very comfortable and secure in the role that they're doing, and they feel motivated to contribute.

Um so I'm, I'm, I'm overhead. So I'm essentially a person who is, who kind of knows about everything that's going on in the company, but who doesn't directly own any of the specific uh functional uh areas. And I'm sensitive to the fact uh that um I need to sort of play my part, and we need to essentially uh together with the co-founders and with the whole team uh there needs to be... it's a little bit of a jazz orchestra uh where you know the, the, the pieces aren't written uh but you want to sound good uh together somehow. And I'm sort of the conductor of a jazz orchestra, which I understand makes the analogy faulty because a typical jazz orchestra doesn't have a conductor, uh but that's effectively my role.

Jake Aaron Villarreal: Yeah, that's great. You know, we are a believer internally that we, when we interview people we talk to them. And I've interviewed over 20,000 people personally for our company, we put people to work, that's what we do um for startups and bigger companies. But I always ask, when we hire our own people, could I see myself working for that person? Like when we're interviewing, whether they're junior, mid-level or senior, could I, could I get, could I get along with them, and could I actually see myself at some point, maybe not today, but could I listen to them and take direction from them, and would I feel good about that? And that's kind of one of the litmus tests. If that's Zuckerberg, that's great. I didn't really think about that, but there's some [truth] to that. I don't think it's 100% proof, but it certainly is one of our, our gauges.

Alex Kruglov: I have a slightly contrarian view to that. Because uh, certainly not my co-founders, but there's certainly individuals on the team that are uh individual contributors rather than managers. And there are some individual contributors who are not necessarily cut out to be managers. But they're amazingly good at what they do. So my general perspective is you want them to be truly great at the thing you want them to be doing, and you want to see a path for them to be truly great for at least let's call it three years. Um and I'm kind of okay... you know my, my other thing that I sort of think about a lot is when you're competing with the world's greatest technology companies on hiring, and you can't afford to pay not only pay... you can't afford to pay more, but you can't pay as much as they do. How do you hire great people? So we're not willing to compromise on quality, but we are willing to compromise on just about everything else. Location. Hours, meaning like they could work weird hours, you know like in the middle of the night, you know some engineers are into that. And also we're more than happy to hire kind of quirky, weird individuals who have strange uh preferences, and might not have a typical profession- hygiene you know in terms of working in a large office. And so you know, we have folks, we have a uh folks all around the country, one person in Vietnam. So you know we, we sort of, you, you kind of want to be able to uh play to your strengths when it comes to being a startup.

Jake Aaron Villarreal: Yeah. You know, one of the mistakes we see uh with a lot of the companies and startups that we work with, is as they grow and, and, and they end up scaling up, is you sometimes you get the best individual contributor at something, and you put them into a management role because they, they're not necessarily qualified. Yeah right. And the two, we look at [it] as two ladders. You have one ladder, individual contributors, and one ladder is leadership. And you need to ask people early on in their career what is it they want to do. What ladder do they want to be on? So they could be individual contributor, at some point they want to cross over and go up a different ladder of leadership. But if you put the wrong person in a role that they don't believe they should be on that ladder, they're never going to be happy. And you can put them back into the other ladder and they are all of a sudden very happy. So there's, I think it's important to understand as you're building your company, what ladder do you want to put people on and be clear about it. Because that's when people leave, they're not happy, they don't like the responsibility. So that's uh really interesting to, to kind of hear your thoughts.

Um I had a question for you. If you were to rank what's most important, there's three items. One is getting your hiring strategy right, meaning hiring the right people, that's one. Two, getting your product strategy right, meaning building the right product. Or three, getting your leadership strategy right, hiring the right leaders in your company. Which one of those three, they're [all] essential, would you rank maybe tier one, tier two and tier three?

Alex Kruglov: That's very tricky because I mean you, you asked the question in a way that was intended to be non-obvious. Um uh so the, the three just to, just to repeat. So one is hiring, one is leadership, one is product. Is that right? Those are the three?

Jake Aaron Villarreal: Yeah, you're gonna pivot the product, so...

Alex Kruglov: I think that, you know, I would put that last with a strong caveat. So I'm a big believer in two-way doors. Uh you know, in sort of understanding those concepts that Jeff Bezos talks about of two-way doors versus one-way doors. So what you don't want to do is to early on, go from a product standpoint, go into a one-way door. Meaning a door that you can't go back out of, and make sort of an early wrong product decision that, that's very difficult to recover from. And product is not just consumer facing, it can also be a technical solution to your uh architecture of your technology uh company. But aside from that, uh it's easy to uh pivot the product, uh and products can be changed. I would, so counterintuitively, I would put people ahead of leaders. So I would put people, then leaders, then uh uh then uh product.

And the reason I would put people ahead of leaders is because I think most uh business books and sort of folks who talk about strategy and startups and all of that talk a lot about leadership, and not enough about individual contributors. And unless you actually have people who are doing the actual work, who are very, very good and uh motivated and ideally self-motivated uh and sort of push above and beyond, it's very, very difficult to have your head above the water and to be able to feel confident with sort of the execution. So leadership is crucial. Um but I put some of that burden on myself. Meaning I don't necessarily need three or four tiers of leadership. Um I can sort of step in and help out on an as-needed basis. And I've definitely become uh, the more you know, the longer I live in a startup land, the more I've become a believer in having world class individual contributors ahead of... especially what we don't have for sure, because we're small. But even in a place like you know, at a bigger company, I'm really not a big fan of managers who have managers under them, who have managers under them, who then kind of have individual contributors kind of three or four levels down. Um so leadership is, is a, is a tenuous term, but I would put that second. Uh world class builders first. Uh and product, which is crucially important, especially in the consumer business, um I would reluctantly put that third.

Jake Aaron Villarreal: Got it. That's, that's great. I actually agree with you in that, in that process. What insights could you share that help you get the hiring process right, getting the right people on the team? Like what have you learned over the years? You've been doing this for a while and multiple companies, that you kind of know "here's the mistakes I've made, here's how I can get it right, and what would, what would be helpful for others to, to, to learn?"

Alex Kruglov: This is again where we have a very counterintuitive process. We probably do it differently from most. So when I've worked at bigger companies, the process is kind of long interviews, uh multiple rounds, uh lots of people to really validate uh the individual. Um and, and I never liked that process. Because I find that being good at interviewing uh is not necessarily the same skill set of being good at your job. Uh some, you know there's interview prep courses at you know McKinsey where I started my career. Uh there's a case interview, and case interview is as much about the skill of being good at case interview uh as it is about actually being good at the potential job.

Quick aside. My wife, after having worked at McKinsey for six years and, and not only been a senior person there, but also having done, having uh uh conducted multiple case interviews where she was the interviewer, she interviewed for a company whose name I won't mention. And the person who was interviewing her gave her a case. And this person worked briefly at a different consulting firm years earlier, much more junior than my wife was. Anyway, this person felt like she didn't do very well at the case interview and didn't continue the process beyond that. So just goes to show kind of how that sort of consulting process works.

Anyway, my uh, my... so, so I had been dissatisfied with the long interview process and I wanted to come up with a better solution. Long story short, our approach is very simple. If we get a sense after uh two or three people talk to an individual for a half hour that potentially there's something there, we give them a project. We pay them for that project. So we don't ask them to work for free, we pay them on a, a sort of the equivalent of a contractor or consulting basis to do the project. And they effectively work for us for a period of anywhere between two and eight weeks, depending on the individual, depending on you know what the role is and so on. And that gives them the opportunity to interview us, and to figure out whether they want to work with us. And it gives us the opportunity to see whether they actually can do the work, and whether we you know, whether this person can fit as part of the team. And then at the end of that process, we go into a full-time offer or not.

Jake Aaron Villarreal: Do you have certain traits you try and look for in anybody that you bring on board?

Alex Kruglov: That's a tricky question because it kind of depends on the role. But the simple way I would describe it is: if I have a perception of where the bar should be, I want them to exceed the bar. Because this goes back to what I said earlier, which is I want them to be 10 times better at the job than I would be. And generally you know, in a small startup I can sort of do most things uh that people do. You know I haven't coded, even though I studied computer science uh somewhat as an undergrad. I haven't coded professionally uh but I can code a little. I can certainly read code. But I can't code right. So that's, that's kind of the thing I can do the least. But you know things like marketing, certainly things like product, I can do some of it. And so, and then of course as we have individuals who are much better than me, I could see the bar that they're setting. And so when we're hiring somebody, we have an idea as to kind of what you know, kind of a cutline of what we think they should be doing. And I always want them to be far ahead of that cutline.

Jake Aaron Villarreal: Got it, that's great. I think um I want to dive a little bit deeper into pop.in. So this is a product you've built. Um talk to us a little bit about how big it's gotten. What's the user community like? If you are not a uh a user of the application, what could you benefit from using it?

Alex Kruglov: The biggest, you know, the, the, the thing that I use... so I, I, I can say all kinds of things of praise for my own product. But I really you know spend a lot of time talking to our users uh and our team does too uh. And in hearing from them, kind of what is their feedback and how would they put it. Uh and, and we have this wonderful luxury of essentially having constant real-time focus groups that are going on on the app at all times. Because it's an app where people can turn on audio and speak to you, and video in certain games as well. So we can effectively run real-time focus groups you know, ask people are playing, and they can kind of tell you what's going on. Uh there's never a time when there's a bug in the app when our users don't tell us about it within seconds. So it's wonderful to be, to be in the middle of a, of a romantic dinner with my wife and getting a ping saying "h-, something's broken." Oh okay, we got to get into it. Um apologize for swearing.

So the, the, the, the... I would say that the biggest kind of uh definitional element of pop.in is a sense of community. Uh so if you uh Jake were to download the app uh and you know join one of... we have these, we have you can play you know individual games anytime with your friends and family. But we have these scheduled uh events that are happening on a daily basis, kind of on the hour, starting around 4:00 p.m. Pacific. And, and if you are new, you know meaning, you know, meaning somebody hadn't seen you before. So not necessarily you are new to the app. But if you're new to them they'd be like, "Oh you know, whatever your username is, what's going on? You know, like you know let me, do you know how to play you know, have you played Spades before? Let me show you how to play Spades," or what you know, whatever game you're playing. And there's this real sense of inclusivity, and there's a sense of uh you know even though you know we've gotten to a significant scale, uh there's a real sense of like intimacy. Uh because most games are played in tables of four. So you know you really get to kind of feel uh a sense of uh con-, connectivity with the humans that, that you're playing with.

Now, the, the experience... you know, one of the downsides is this, you know some people are introverted. They don't necessarily want to uh uh uh be talking to a whole bunch of people. So we're sensitive to that, and uh and you know you can play any of the games without turning on uh your mic or your uh camera. And you're just kind of an avatar and, and you're uh you're playing. But what tends to happen is, you wait around and then everyone turns on their mic and they say "Hey Jake, good game, you know good for you." And so all of a sudden you kind of want to turn on your mic and say, "Oh thanks so much, I really appre-, appreci-." And all of a sudden you find yourself by the end of the game session letting them know what the name of your cat is, and so on. So it's funny where you know it's easier for extroverts to immediately jump into the app. But the people that we retain the most tend to be introverts because they feel like uh you know they feel recognized uh and they feel a sense of community. And they feel like uh uh and they feel like they can kind of control how much and whether uh they engage with uh with other uh with other humans. So, so you know uh the, the thing that I'm most proud of is a sense of community and a sense of engagement uh of our ecosystem.

So a typical uh a typical uh you know our core metric that we pay the most attention to is not time spent uh on the app, but time playing with other humans. Uh that's the core uh metric. And you know we're seeing that when people play, they tend to play you know an hour and a half or so uh per day. Um and uh you know we always, we always want them to go outside or to go hang out with their family or to go, go to a dinner party or whatever else. But when you happen to be you know alone uh at your house, there's this real sense of presence and a real sense of community uh that you can join. That's, that's, I think it's great.

Jake Aaron Villarreal: I mean in this remote world that we've been in since the pandemic, you know you work from home, you do things in your house, there's that social connection that you don't get as much maybe as, as you used to.

Alex Kruglov: Yes.

Jake Aaron Villarreal: So any game that you can play is great. And if you can connect with others I think that's even better. Do you actually see them? Like, is there, can you join a game and are you seeing people before you join?

Alex Kruglov: It's, it's fully integrated. So essentially the easiest way to think about it is like you know, think about a tabletop uh game right. Where you know people are playing cards around a table uh, and marry that with FaceTime. That's kind of what it looks like.

Jake Aaron Villarreal: Okay.

Alex Kruglov: So it's, it's a full screen uh on your mobile phone. And you know some people you know don't turn on their video. And so you don't see them, uh and so they just show up as whatever avatar you know. It's either a photo of themselves or like a cartoon avatar you know that, that we provide for you that looks really cool and slick. Um but uh, but absolutely people can join on, on video and they can have uh you know a nice uh a nice chat. And, and we have a lot of tools around uh safety uh and around uh uh community uh to really make sure that if there are bad seeds that join that they're quickly weeded out of the app. And we're not a libertarian open-to-all platform. So if people misbehave they get kicked out and they can't come back.

Um it's funny because our you know, people say think gaming and then so they think about you know, they think it's a bunch of 16-year-old boys. But I would say our core user is probably like a 29-year-old mom who three years earlier uh would maybe go clubbing uh or go on dates you know on her Thursday night. And now it's 8:00 and uh you know she put her kid to bed and she kind of wants to you know hang out with a bunch of people, and she can do that without having to put on a bunch of makeup.

Jake Aaron Villarreal: That's great, I love it. What's the business model?

Alex Kruglov: Uh the business model. So we don't have ads. And the business model is around microtransactions. So uh users can play for free, it's completely free to play. Uh and they have the opportunity to earn uh our currency which we call pops uh by doing well uh and by playing a lot. Uh but there's also a bunch of things that you can buy uh inside of the app. A bunch of merch, uh some of it is physical merch uh like this t-shirt that I'm wearing uh and uh and this and this uh water box, bottle. And, and uh uh, but much of it is, is digital merch, you know just like you have in lots of other uh free-to-play uh free-to-play games. So if you want to kind of pimp out your experience uh you can spend. And if you don't, then you know it's completely free to play.

Uh we're also introducing a feature uh in the coming weeks that we're really excited about, which kind of continues to go down the path of what we call joyful togetherness and community. That we're going to be calling Kudos. And the idea there is that people can buy these uh uh um uh emotions to gift to others. So uh, so somebody can be gifted uh as a "thank you." You know they're very helpful, they're very funny, uh and you know they can wear those as a badge. So you can buy them, but you can't give them to yourself. Uh you can only get them uh from others by being a good individual. And so those cost the buyer uh, they don't cost anything uh to the receiver. So it's just another like little you know fun thing that we're playing with.

Jake Aaron Villarreal: That's really cool. Yeah, no, loneliness is such a big problem to solve and it causes a lot of mental... maybe it's not mental illness, maybe there's just like things that are going on in your life where you know you're out of a relationship or you just, you want that sense of community and you don't always know where to get it, you know?

Alex Kruglov: And our Surgeon General is, is referring to loneliness as an epidemic. Uh I would argue that loneliness is a dramatic uh problem uh. And it is especially a problem... you know I'm a parent of three uh children, one of them is a teenager. Um and you know, thankfully she's back to normal when it comes to school uh, but there's, there's, especially with the pandemic or post-pandemic, but even before the pandemic, uh there's, there's a strong sense of loneliness among community. There's much less family among people of you, who are under 40. Uh people are less connected to their friends, people move around. Um and so anything that we can do to contribute to human togetherness... and again, in-person human togetherness is always better uh than not in-person, but we can't always you know uh uh uh experience that as, as humans. Um and so we you know, delivering joy to people is, is absolutely our core mission.

Jake Aaron Villarreal: There's, there's other applications and platforms out there, social networks, but it seems like you've carved out a nit- [niche]. Um, who would you say is your biggest competitor today in this area?

Alex Kruglov: Well it kind of depends what category you're looking at, you know. So if, if, if you know there, there are certainly many gaming companies uh that are out there. Uh and uh most, most of them don't have much human interaction. Uh but uh hardcore uh hardcore AAA games uh uh, people play with headsets and they're talking to other players that they're playing uh against. So a game like Fortnite would certainly be in the category of potential competition uh to us uh for [a] certain category of users. Now Fortnite is not necessarily welcoming to a very casual gamer. Uh but it absolutely is in the same competitive set, and it is a place where people hang out. Um those games, you know that game and a number of others tend to uh be much more skew towards people talking to people they already know, uh rather than kind of making new friends or meeting new people. Um and so in, in that world uh are you know...

And there's obviously lots of dating apps, which are around dating. Um and so we, we're not directly in the romantic dating space. But we call what we you know, what we do to some extent as kind of platonic long-distance dating among you know, amongst uh friends. So you could, you could say that the dating apps are in our competitive set. And there's also locally based Meetup type of uh uh experiences where people meet up to play you know trivia night at a bar or whatever else. And so you know we respect them and we want them to do really well, but you could argue that they're in a competitive set.

Uh I would argue that uh social networks, even though they're called social networks, are not very social. They're just mostly feeds of things that you consume and scroll through. When it comes to actual human interaction, action, that's not what they do. Um the exception to that probably uh is Snapchat. Uh where the majority of engagement on Snapchat actually happens with people you know interacting with other people. But again, that tends to be mostly focused on existing friends and existing friend groups rather than new folks.

Jake Aaron Villarreal: Yeah, I hear you. That's cool. I, you know there's... I have two young boys, and I know that gaming even at a young age, you know they're both under eight, but they're already getting into games. And you can kind of lose people when they get too focused and they're kind of on their own doing it. Um...

Alex Kruglov: It's funny, my uh my 10-year-old, what she does is she essentially recreates pop.in but on Roblox. So what she does is she gets on the iPad, she FaceTimes with her real world friends on the iPad, and then while they're on FaceTime they open up Roblox and they tell each other which spec-, which server and which game they're in, they're at, and which game they're playing. And so they see each other on Roblox where you can't talk to each other, but they're talking to each other on FaceTime. So essentially that's basically what pop.in is. She just kind of you know, hacks it.

Jake Aaron Villarreal: That's really cool. I got, so is there like an age range? You said females typically 29 or older, you seem to be like that's like our you know, if you, if you kind of have that you know the target like, "this is our sweet spot"?

Alex Kruglov: Uh it tends to be uh out of college uh is our typical kind of age range. Uh meaning you know, in college you know it's about a social experience as you can possibly have, uh not people who are actually in college, I'm not talking about everyone who's college age. Um uh so it tends to be sort of out of college. It tends to be a little bit more female than male because our games are casual, but it's about you know 56, 44 male uh female/male ratio. Um we don't let anybody under 17 uh join just because the possibility of being on audio and video, the threat associated with uh the potential of uh negative behavior uh uh you know we think of that threat as bigger than the benefit that we could offer uh that community. Uh but that's the basic, that's kind of the, you know we probably have a big chunk of folks that are, that are kind of in the young parent age. And then we have another chunk that's not insignificant that are kind of empty nesters uh where their kids are not out of the house. And we have some grandmas, and the grandmas are you know very active. They ask a lot of questions, they're not necessarily the most technically savvy uh but they're, but they're very active.

Jake Aaron Villarreal: That's great. What uh what type of games are on the platform today? What are your most popular games?

Alex Kruglov: Our most... so our typical games are real world games that you're familiar with that you play in groups. We actually started out with a game that wasn't very well known called Liar's Dice, that was our first game. And it's kind of like a poor man's poker, but you play it with you know rolled dice. People might have seen it in Pirates of the Caribbean and it's mentioned in the book Liar's Poker by Michael Lewis. But it's not, it's not a super well uh uh, is not a super well-known game. And one of the side effects uh of having a game that isn't super well-known but having lots of human interaction is that we learned that our best onboarding is like another human teaching you how to play. Which is much better than reading a tutorial. Uh so that was kind of our first experience when we kind of were in beta of pop.in.

Uh today our most popular games are probably Spades and dominoes. And the other game that was kind of [a] surprise, that we did as an experiment but has really worked out for us is actually crosswords. So we partner with the Hearst Corporation, they provide us with you know a bunch of daily crosswords. And what's interesting is that we essentially created the only mode uh on mobile that you can get on, on the App Store and Play Store, the only time that you can play crossword with other humans. Which you know if you think about it, is you know if you, if you are working on your Sunday crossword and you, you know, you don't [have a] clue, you just ask someone who is next to you like, "Hey, do you know what you know, what you know word that starts with u and ends with a that protects you from rain or whatever, right?" And they get, they tell you it's "umbrella." But like, but now there's actually a bunch of humans who are playing with you at the same time. It's both collaborative and competitive. Uh so it's really fun uh uh to do crossword together with other humans.

Jake Aaron Villarreal: That's great. God I got to share this with my family and we're local in the, in SoCal and also in Norther-, Northern California. So yeah I could really get some good uh good evenings together and some good family time which we can't get all the time. I think that would be really fun to do. What's one of the problems or not problems, but one of the challenges you didn't anticipate when you started pop.in? I know you transitioned it, but when you transitioned to pop.in what's something that you've learned that you didn't anticipate that you've had to solve for, and, and you feel like it's insightful that you could share with the, with the [listeners]?

Alex Kruglov: One thing that's uh very interesting is that uh what is our biggest strength is also arguably one of our bigger weaknesses. So the thing that you hear from our users, especially active users, the best thing about pop.in is that "I met my new best friend on here." The best thing about pop.in is that "I formed these amazing relationships with people from all around and I got to know them and I feel so close to them." So that seems wonderful right, like you know, why would that be a negative? Well the negative is that sometimes, and this goes back to loneliness, this goes back to kind of quirky individuals. Sometimes they don't necessarily want to bring people from their real world into this experience. So sometimes the fact that it's an escape, the fact that it's an opportunity to connect with others, the side effect of that is they don't necessarily have uh a strong incentive to go bring 10 of their real world friends uh into the app. As opposed to on Fortnite, where you need a crew to kind of play with, you know, of existing friends. And so there's a v-, virality that's kind of built in. So we are sensitive to the fact that we don't want to kind of force users to connect with their real world friends. On the other hand, you know, we want to have a strong word of mouth growth uh ecosystem uh where there's it, that's kind of built into the app. And walking that fine line is definitely non-trivial.

Jake Aaron Villarreal: Gotcha. If someone wanted to find pop.in or connect with you, where would they go?

Alex Kruglov: Well the good news is our name is literally our URL. So pop.in is our website. So if you go there uh it will show you the links to download in the Play Store and uh and the uh uh in the App Store. Or you can just obviously search for them. Um we have an Instagram and Twitter handle, they're not very active but we have them. Uh and uh if you want to follow me on akruglov on most [platforms].

Jake Aaron Villarreal: That's great. Well as we wrap up here Alex, I want to thank you for your time today and joining us, and also want to thank the listeners for spending your time listening to stories about startups and hopefully you got some insights out of here. I certainly did. Um I look forward to catching up with you in the future Alex and seeing how pop.in goes and how you grow. And to all our listeners on the next episode, enjoy the rest of your day. And until next time, peace out.

Alex Kruglov: Thank you so much.

Jake Aaron Villarreal: Before we wrap up I want to give a big shout out to all the entrepreneurs that have joined to make this podcast possible. And for all the listeners for listening, it means the world to me that you chose to spend your time with us today. I'm your host Jake Aaron Villarreal signing off for now. We can't wait to connect with you all soon on the next episode. Take care.  

This show is sponsored by Match Relevant, a company that helps venture-backed startups find the best people in the market and they do it in three simple steps. First, they sit down with founders to understand their story. Second, they tell their story into multiple candidate channels. And third, they schedule interviews within 48 hours. Find us at matchrelevant.com to learn more about how we do it.  

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