DN #36: Hyperlocal Community Apps, Trust Without Background Checks & Grant Writing Hell (w/ Kaia)

Kaia:and I feel like I'm going to fail every day. And I think that's really important to me.

Niklas:Hi and a huge welcome to you, my lovely listener. So glad you're here. Today you are joining me for chat with Kaya. Kaya, so lovely to have you. Thank

Kaia:Thank you so much for having me.

Niklas:You've made a bit of a transition from shareholder value to community impact. I'm really interested in hearing the whole story.

Kaia:Yeah. So just to tell you a brief background of mine, I started my career at BCG and then I went to Pitchburg where I built out the Emerging Health Tech Research Division. And there, you know, working with all the

Niklas:So just to tell you a brief background of mine, I started my c career at BCG and then I went to Pittsburgh where I filled out the Emerging Health Tech Research Division. And there, you know,

Kaia:health tech, even though it was corporate and it was all for profit, I kind of realized like my passion for working with areas that can make an impact. You know, I really believe in the concept of value based care. And I think I really learned about that while I was at Pitchbook and being able to work in. Something that I felt passionate about. After that, you know, I went into the startup world. I worked at Venture Studios. I started a few things. And I kind of like played around and I had a lot of different, like, really great experiences. And I ended up landing on deciding to build my own nonprofit, which I named ShareVita. And ShareVita has the kind of the mission of leveraging technology to bring communities closer together. I believe that for the most part, technology can really

Niklas:experiences and I end up planning on deciding to build my own nonprofit, which I named Share Vita. And Share Vita has the kind of the mission of leveraging technology to bring communities closer together. I believe that for the most part technology

Kaia:be used to bring people apart, you know, everyone living on their phone and not in reality, but I think while used in the right ways and with compassionate care, we can actually use as a tool for creating communities and making friends and helping each other out. So that's really what I was trying to build there.

Niklas:so how did the idea of Share Vita and Share Skippy actually come around?

Kaia:Yeah. So I had a friend who was elderly and you know I would help him out walking his dog and just like with some household chores when I was free. And this is when I was living in Oakland. And then I got a job in San Francisco. I was head of operations at a startup, so I had moved there. And He ended up getting very sick and wasn't able to walk his dog anymore. He's all better now, everything's good. But for a while he was at home and he could let the dog out, but he couldn't walk it. Like he couldn't walk a block. So he was struggling, you know, to take care of his dog. So I posted on Facebook in a buy nothing group. a buy nothing group is a group where people can kind of post things that they want, like, hey, does anyone have ex? Or hey, I have ex. Does anyone want it for free? And the idea is Like, you know, instead of trashing things, you know, sharing it or giving things out to your local community. And I said, hey, I have a friend. he is sick, he's unable to walk his dog, he's home all the time. Would anyone love to borrow his dog to go on a walk? he lives near the lake. And I got an amazing number of responses. I was really excited by it. so I was like, wow, like. People seem really excited to help somebody out to walk the dog. And a lot of people are like, my gosh, like I would love a dog. Like I work, I can't have a dog. Like this would mean so much to me. Or like my kids really want a dog and like we're not doing that. But they would really enjoy getting to walk somebody else's dog. So I thought like it was something that could be really mutually beneficial on both ends, both for the dog owners and for the people walking the dogs.

Niklas:And I mean it's a huge contrast. I've been in consulting, for example, as well. You said you were like PCG. So I like the it's really I already startup and the the consulting world are quite different. Corporate world is also really different. The building impact startup is quite an evolution. And I also think it might be really challenging at times because at the end of the day, there's also the financing aspect. How do you deal with that actually?

Kaia:The financing is tricky, you know. We try to apply for a lot of grants, we take donations, you know, continually looking out for things. so it's not easy. And I have gone back and I'm working on another project, you know, part-time as I run this, just because in this, you know, political landscape, it's just not great to do fundraising. And in addition to share vita, we also have a ride share component. I am fortunate that it is pretty low cost to run. And I have a great team of interns who are. helping out with everything. And the thing about being a nonprofit is you are able to have interns who are volunteer and not paid. I'm a strong proponent of paying people who work with you, but you know, as a nonprofit, you know, when somebody wants to volunteer and do something that they believe is impactful on the side, it is, you know, legal to do that and not pay them where it's not legal for corporations. So we've been able to keep it pretty low cost. But we are always looking for those funding opportunities, which Are not fun to apply for. They're very redundant, that grant writing. It's yeah, it's not the sexy part of the job.

Niklas:Yeah, I think I I'm so I I did I did a PhD after finishing my master's and actually I had to write these research proposals as well during that time. And I can fully agree. So this is just it's really boring work, I would call it. You have to do it, but but it's not something that is really fun. Another thing that I think is challenging, but it's challenging everywhere, is actually growth. And I would be interesting without a marketing budget or something like that, how do you actually handle that?

Kaia:Yeah, so we Have two components. We have the sheer skippy side of Share Vida, and then we have the Rideshare Tahoe. So just to give you a brief overview of Rideshare Tahoe first, the idea of Rightshare Tahoe, we mostly just run in the winter, and it's for people who want to crawl from, you know, Sacramento, Reno, San Francisco, Oakland, South Bay, you know, anywhere in the Bay or Reno to Tahoe and back. And the concept with that is crop pooling in the US generally does not work. It's been proven time and time and again due to trust issues, the way our public transport and our highways and our roads. Are set up, it's very tricky. But with skiing, everyone's going to and from the same place at the same time. So it's a lot easier for people to do that carpooling. And that's a bit easier to advertise because I partner with the slopes who are really excited to have people crawl pooling and are willing to, you know, kind of get that marketing out there for me because they have limited parking and the traffic is, you know, not fun. It's worse than riding grants. and then for Share Skippy, it has been a lot. You know, fortunately my interns have been really good about posting on our Instagram and Facebook page and getting the word out there. I've spent a lot of time just putting flyers up around town. You know, that worked incredibly well in the beginning. You know, in my first, you know, two, three weeks of putting up flyers, we got about three, four thousand users. so that was showing like a really high like RI on time and commitment, but you can't just put up posters for forever. I have started partnering with some elderly centers who, you know, have a lot of people who need dog walking and then their volunteers. Find out about it through them and then they're able to help people who are not just at the center, but other people on Share Skippy as well. I've been having, you know, local newspapers and articles write about us, so that's been helpful as well. I would say that's kind of been the biggest slump in growth is the inability to do marketing without that budget. But there are creative ways to do it.

Niklas:Yeah, I mean to be honest, I think distribution generally is something that is struggle with it, especially also if you look at X solo Founders struggle with it, especially if you want to like have profitable growth. I think if you

Kaia:Yeah.

Niklas:don't really care about losing money, that's a different story. But that also only works for a certain amount of time, right? So the I think that it's actually quite hard. Then when we look at technology and what you're dealing with, I think it's often associated to loneliness. And then on the other hand, what you are dealing with are tools that try to fight it at least a bit like how how do you design tools that intentionally bring people together in real life?

Kaia:Yeah, so the thing about both of them, you know, Cher Skippy and Right Share Tahoe is you are meeting people in your hyperlocal community, right? Like if you're gonna be walking the dog, you're you're not gonna wanna have to drive twenty minutes to do that, right? If you're gonna be carpooling, it's gonna be with somebody nearby, you know, carpooling, you're spending three hours in the car with them each way driving up. So it's like it gives you time to get to know them. I've hitched rides home from Tahoe with complete strangers. I've met on the chairlifts and they've ended up becoming some of my best friends. So it really enables you to build these friendships that can then grow outside of how you met, I believe. And with Cher Skippy, you know, like one user story somebody emailed me and they're like, hey, I found out about Cher Skippy through this, you know, newsletter that you guys were written in the Grand Lake Times. And my best friend and dog of 13 years died six months ago and I haven't brought my To find another one, and you know, she said she met this person who had the same type of dog and they started meeting up, and this dog used to be crated twice a week, and now she's taking care of it twice a week instead of the dog being in the crate. But this young lady who has the dog who works in person and was, you know, unable to take care of her dog also got to know her, you know, in the drop-offs and pickups, and you know, they met the first time and hung out together to see how the dog interacted with her. So they got to just know each other at a personal level and it's almost like creating these little micro excuses to get to know your neighbors. And once you know them, you can do what you want with that, right? and I think I'm hoping that these friendships extend beyond just the dog.

Niklas:When when you look at feature design like more detail, like how does sa a tool like Share Skippy actually solve that and what matters mu matters most for s topics like trust, safety or these offline connections at the end of the day?

Kaia:Yeah, so for trust and safety, that is a hard thing we've gone back and forth with. We would love to do like background checks and ID verification that is, you know, pricey. So we have not done that. We've thrown around the idea of letting people, you know, pay and verify themselves, but there's still like those processing fees and that setup that we have not done. What we do do is ask everyone to upload their social medias, their LinkedIn, their Instagrams, their Facebooks. So you kind of have some social identification, verification. We ask everyone to meet in public in a safe space the first time. Don't just let somebody come to your house and you know drop off or pick up a dog. Don't let them have it until you've kind of met them and talked to them a little bit. But at the end of the day, like there is always that concern and that risk. we do have people leave reviews. So you can see, okay, this person has driven other people to Tahoe, people have left good reviews, that social verification component that you see on a lot of other, you know, apps like couch surfing or something. But I think it is tricky, you know, and we kind of there are some laws basically saying, you know, if people meet on social media and something happens, the social media isn't deemed liable. you know, if people Meet on a dating app and something happens, the dating app is not deemed liable. People decide what they want to do off of it. And but of course, like that's not what we're hoping for. We don't want anything to come about. So we try to put everything in place that we can. We have ability to block people, to report people, to flag them. So we're trying to keep a close eye on what's happening to make sure everyone has a safe experience.

Niklas:I remember like quite a long time ago now, like eight or nine years ago, I thought about an app with a friend that was called like Travelmate and the idea was that you could meet locals in places like for example, if you flew s to Sri Sri Lanka you would have the ability to search like people because I always believed that ex like you'd experience a place through like the food and the people you meet and so on. And we actually didn't launch the app in the end because we were so worried about this trust problem. I mean you are like hyperlocal, but we just figured like if somebody something really bad happened in in a certain place due to this and to due to the people that were met, like that that would be something we couldn't like and we we didn't find a way to mitigate. So it's really interesting to hear Hear about that, actually.

Kaia:Yeah, I think it it is a concern. And I think part of kind of my mentality did play into it. I tend to be a very trusting person. And that's just like kind of how I go about my personal life. and I think, you know, like proceed with caution, right? Like life always has risks, and you're not going to be able to completely mitigate that. But I think, you know, you can try to do things in a safe way. And, you know, we have like explanations on our websites about like how we recommend meeting, how we recommend talking, you know, on Ride Showtaha we ask everyone for the license plate. we track every ride, assuming you book it through our website so that we know, you know, like X went with this person on this day and this car with this license plate. so we're able to keep better understanding there.

Niklas:What I find interesting, so I've looked at Pitchbook back in the day when when I looked at like early stage startups for evaluation. So the I think this research background that you you have over there, that's quite interesting. And I would like to understand how this actually translates to like a a startup or an app that you are building. What what did you take from those days?

Kaia:Love research. I think researching is definitely my happy place. I love going out and just like learning new things and like digging down rabbit holes and kind of like building my own frames of thoughts based on like everything else. Like I find that super, super exciting. I think in building this, you know, you have your hypotheses and you're constantly trying to prove yourself wrong as fast as possible so that you don't invest time into something that's going to fail. So I think in doing that, you know, when we went out, we're like Like, okay, like there's people who like can't walk their dog, and you know, they want help. But we went out and we did research, we talked to everyone who's using we're like, wow, like the market is so much bigger than that, right? People are excited by it because they work in person, or a lot of people just have small kids and they have this dog, and now they don't have time for the dog, or they're pregnant. So you're like trying to just go out and like ask people as many questions as possible to like learn and kind of shape your theses off of that. One of my favorite books is called The mom test. If you haven't read it, I really recommend it. It's about you know how to ask questions where you're going to get the right answer, and people will just say what you want to hear. Because especially when you go out and you're like, Hey, I'm doing a non-profit, like it's gonna enable people to ride you up to Tahoe and you know save the environment and save money and save gas. Everyone's like, that's great, right? but you really need to go out and be like Hey, you know, if you had the opportunity to find somebody online to curl pull up to Tahoe, would that be something that you would ever even consider? You know, and pitch it in a way that you're not egging people on to be excited for you in order to get the truth.

Niklas:I think this also leads me to the next point. Usually are a lot of apps are at the end of the day transactional. And now you're scaling a community that that isn't in that sense transactional, at least not on a monetary basis. How do you how does it work? How do you keep it like more community based and not so transactional?

Kaia:I mean, I think at the end of the day, it is still transactional, right? Like, hey I need somebody to walk my dog. There is a benefit to that. And I'm somebody who wants to walk dogs. I'm somebody who lives in the bay making 300,000 a year, and I feel guilty that I never help any of my neighbors and I want to find a way to give back. And this makes me feel good about myself, right? Like there is kind of like the both people are gaining. There is a mutual beneficial transactional component to it. But I think you know it doesn't need to be monetarily transactional. And I think sometimes society like high Of fixates on, like, it's only transactional if it's monetary. And I think it's okay to make things transactional. I think it's okay to be like, hey, like, how can we help each other? I think that's kind of the basis of a lot of relationships. Like the people I'm friends with, I have fun and I learn and I grow from them. And that's why I want to spend time with them. And they want to spend time with me for you know, whatever other reason that they benefit. It's kind of that transactional nature. But I think shifting it away from the money and being like, hey, how can we help and benefit each each other, that's not just purely based on the wallet is an interesting way to think about relationships. And it kind of like brings in this different point of view that a lot of people just often forget. And I think it kind of reminds people of like, like there's so much I can gain from others or ways I can help others that don't revolve around a paycheck.

Niklas:When you when we go back to yourself, I think you have written about your cat chaotic brain and why founding Fed like the only job that matched it. Can you unpack that a bit for me?

Kaia:Yeah, I think for me working the typical nine to five sitting on a desk all day is really hard. I love, you know, jumping around and like putting out fires and figuring out the next thing to fix. I wouldn't, you know, my schedule looks like, you know, I get up, I do work for a few hours, I hit the gym, I work for a few more hours, I go on a walk with some friends, I work for a few more hours, I go hang out with my friends in the evening, then I come home and I do a little bit of more work for a few hours. And I think like being able to jump around just really like stimulates me and helps me keep moving and keep thinking and the blood flowing. I also think Isa found that like you get to work on so many different things, which is just exciting. Right. and I feel like I'm going to fail every day. And I think that's really important to me. If I had a job where I thought I was gonna, you know, go in, do a great job, get praise, and go home, I would get so bored that I wouldn't be able to give it my all, I think, and then I wouldn't end up doing a great job. So I think, you know, just as a founder, this all that responsibility, but all that stress alongside it that I think like really pushes me. It's like the good pressure.

Niklas:I think that's really great because I think if you ask yourself like if you should start a company or be a founder, you're not really sure and you need some assurance on that, you're actually probably not suitable because it will

Kaia:Yes.

Niklas:be so painful, like at the end of the day, if you if you start into it, because things go wrong all the time. You have to find ways to finance things. And I think this is really it's really interesting to see what led you there. And then again, how do you actually or what would you advise to other people whose brains kind of work the same way? Would you think they should do the same thing or can they also find something else?

Kaia:I think you can find jobs, right? Like I was at Pitchbrook, I was very happy. You know, I went to a venture studio leading ideation and research and I was very happy. I think, you know, finding a job though where you get to have ownership is really important, you know, like being micromanaged I know doesn't work for me. So I think that's really important. Or I know some people with similar types of brains where they just find a job that has really great work life balance, right? Like, you know, they're working like 30 hours a week and then they find a side project that they're passionate about. And then they kind of still get to jump around and explore since they're doing their day job, you know, like twenty, thirty hours a week and doing their own stuff. So they get that variety and versatility that I think is really nice. I think a lot of people like Can jump into the founder thing too early before they're ready. And like it is hard. financially, it can be stressful, work-wise, it is it is stressful. And I think people should do it, you know, with a grain of salt, you know, like test it out, see if it works for you. I also think for me, like solo founding is very difficult. I love collaborating with people. So I think it has been a bit lonely. I like really do highly recommend like finding a co founder, right? I think I've figured my way out of this loneliness through my amazing group of interns. But I think most people, you know, aren't able to do that, right? Just because hiring early on can be expensive and most people don't have the money to hire interns. you know, if you're not a non profit.

Niklas:Yeah, I mean also you you need people I think in a startup that are kind of working on it full time. Like that that would at least be my my opinion. Maybe it works with interns as well, but like in general, for example for sales you want somebody who does that like five days a week, every week,

Kaia:Yeah.

Niklas:to get the consistency going. I think that that's important. You cannot exchange these people every two two months because they

Kaia:Yeah.

Niklas:Client relationships will move on and so on. So I think it has its limit. I think there are some people who are really, really

Kaia:Mm-hmm. For sure. For sure.

Niklas:foc yeah, really focused on solo founding who say, Okay, I'm I'm super happy that I had just have a few contractors and I don't have to deal with my business problems with other people. And then I think there's the other side that you just said. So it's the biggest benefit probably is that you can actually discuss your biggest problems with somebody kind of

Kaia:Yeah.

Niklas:and you're not stuck off with them alone, I think that's a big challenge as a as a solo founder. And I know for example one we see who explicitly for that reason doesn't invest in solo founder. He says I want one technical person and like one hustler, one salesperson. That's kind of the team I want to see when I look at founding teams. Otherwise I would probably not invest in you.

Kaia:It is interesting though, YC now is 20% solo founders. You know, a few years ago it was 5%, and now they're up to 20%. You know, you've seen some interesting things in YC with them kind of shifting, you know, with AI. I think they're kind of like second guessing some of their investment types in what they're going after, you know, just with all these changes coming about. But I think like mentality and mental health, like, I really suggest having a co-founder. And I think you're right, like the interns do not replace having somebody like fully committed in it. and there's the training, there's the turnover, and you know, they're less experienced, which is great. And I love building these people up and I find so much joy out of that. But they're not able to push back, you know, and tell me my ideas are stupid as much as I would like. I think with me, one thing that does help is because it is kind of a community app. It's something that my friends do understand, right? When I talk to them about it, they're able to kind of understand what it is and what I'm going through to a basic level. And I rely very heavily on my friends, you know, as almost like my part-time co-founders, to be like, why are you doing that? And I think I'm very fortunate to be able to have like really smart intellectual friends that I can go to for advice who are also excited to talk about what I'm building. And that's because I'm doing, you know, a consumer type of project.

Niklas:Yeah, I also think you're just in the right place. So I've been like in San Francisco, I think last week. so and it actually there are just I I feel there are just a lot of people who are interested in startups and have seen startup problems. So that's I think very helpful. I've also met and that's that's interesting, I think the founder of a company called Polsia. I think he's raised like thirty million as a solo founder. with a goal to build like the first one person one billion company. So the first one person unicorn, that's the the vision he had in mind. And he said he had so many co-founder conflicts that his last company that he said or startup that he decided to just go by himself and

Kaia:Alright.

Niklas:just work with contractors and move alone. So I think that's the other side. I still believe that if you find a co-founder That you ideally have known for a long time. So maybe n not somebody you met yesterday, but

Kaia:It's hard.

Niklas:somebody you knew ten years ago. You know that you'll survive the day where you fight because things will go wrong. Then it's probably a good idea to start something as a team because you just increase your odds of success. it's very rare that you have people that are really good at everything. So yeah.

Kaia:Yeah, I work with a few co-founders doing like some co-founder therapy sometimes on the side. And, you know, I work with some people when they're like starting up and trying to figure it out. And I always tell them, write a pre mortem, you know, write your prenup before you get started. And it sounds bad to be like, hey, do you want to co found this with me? Like, what are we gonna do when we break up? But there's You know, like just like people getting prenups before you get married, have that prenup before you engage with a co-founder. So you just understand, you know, if somebody decides they don't want to work with you anymore, you know, what discount are you buying them out at? How are you gonna go about that? Are you allowed to fire each other? You know, and I think some people are like, we're just gonna create a clause where we're not allowed to fire each other, like we have to quit. And what happens then is somebody decides, I don't wanna work with this person anymore, but I don't wanna quit, and things just get nasty. And I'm like, that doesn't work. You guys need to figure out like before it happens. And it's sad. It sucks. But it's better to do it when you're in a happy place.

Niklas:Yeah, so definitely I mean there are reasons why you might not want to do that and that's also fine.

Kaia:Yeah.

Niklas:I think if you go full time into it, you might do it part time with a friend and just say we want to create something together and then it it might actually work this way. When you get venture capitalists in they probably demand some kind of vesting schedule again from you, so then it's it's sorted anyway. But yeah, I I agree it It makes sense to discuss these ugly topics early and not not like because it's too late. When things go wrong, it's it's already wrong. It's really hard to fix. And I have seen like co-founder conflicts and it's this is always very ugly. And the sad story is that's the other side of it. I've rarely seen a company really survive it. So that's the other other side of it. So I'm not sure how how much then will survive. So if an early stage startup loses the founders, I'm a very strong believer in that, then the company is just dead. That can cannot be saved. it's my opinion. looking back at you, what I would find very interesting is when do you feel successful actually currently? If you look at your startups, how do you measure success?

Kaia:So, you know, I am a data person, so I love my KPIs. You know, I look at like number of people on the platform, number of matches, number of rideshare, number of dogs walked, you know, repeat users. but then, you know, it is a personal thing. So then I also look at like When I get an email and somebody's like, hey, like I just want to reach out and tell you about this awesome experience I had because of you. Like that's what makes me really feel successful, right? Then some of my successfulness, it's like when I first started this, I had never touched the terminal. I did not know how to code at all. And I was able to build it from scratch. Of course, vibe coding, Claude helped a lot. but I was able to do that without by myself. And I felt super successful. I was like, you know what, even if this fails, like I learned, I gained something. And that felt like success to me. And then also with my interns, you know, when my interns like struggle to do something or work through them something together and they figure it out and they learn and now they have this skill they can take elsewhere, that feels like success for me. You know, I love, I really love managing and like building people and like mentoring. So I think it's like it varies. What is success?

Niklas:One last question. If somebody now thinks about starting a purpose driven free community tool, what would you recommend to them?

Kaia:I would say You know, unless if you have the savings, you know, do it on the side, gain some traction before going full time. that funding and the grant is is hard. So don't rely on that too early. And I would say try to bring if it's a community focused, you know, driven app, reach out to as many people as you can. Like see if you can get anyone excited or on board with it. Find, you know, similar people who have a lot of ideas. There's a lot of people floating these ideas who might want to, you know, partner with you or be ways early on they can market it, you know, like, There's mutual aid websites. There's a lot of like similar things out there. So like kind of like lean on to another one if possible. And then also the area you're interested in, a great way to kind of get to know the people and figure out how to go about it is start volunteering, right? Like if you want to like decrease clothing waste and start something about that, go to every clothing swap you can find for three months and meet everyone there and talk to people because those are gonna be your first. customers and find ways to find the community that might already exist. You know with Ride Shire Tahoe, I was a big skier. So it was like I was already immersed in that community, which really helped it grow.

Niklas:Thanks for the final words, Kaya, as well. So nice to have you on the podcast, and to you, my lovely listener, see you next time.

Kaia:Thank you so much. Thank you so much, Nicholas. Great day.