Fixing US Loneliness Crisis - Is It Too Late Now? Aaron Hurst & Charlotte Massey | US Chamber of Connection

Shamil Malachiyev: Hello everyone. This is a first for me: two guests at the same time, and not just any guests. Aaron Hurst has spent his career building movements that connect people in ways most of us don't even realize we're missing, from the pro-bono service market with Taproot to purpose-driven workplaces with Imperative. Charlotte Massey is one of those rare founders comfortable both leading a civic movement and inventing outdoor gear. She's the force behind Seattle's chapter of the Chamber of Connection and co-founder of Gnara, an outdoor apparel brand Forbes called one of the most innovative out there. Together they're here to talk about how you actually build trust and connection in a city, everything we all realized after COVID, and maybe even try to solve it for the country. Hi, guys.

Aaron Hurst: Great to be here. Excited for the conversation.

Charlotte Massey: Yeah, thanks for having us.

Shamil Malachiyev: If I gave you both a magic wand and said you can fix one thing about how people connect with each other in Seattle, what's the first thing you'd change?

Aaron Hurst: Go for it, Charlotte.

Charlotte Massey: Well, with magic-wand powers, I'd still tackle one of the issues we're working on with the Seattle Chamber of Connection, which is creating an onboarding process for when people first move to the city. I moved to Seattle in 2021, during the pandemic, and had a really hard time figuring out how to break in. I found Seattle to be an extremely welcoming place once you've made enough connections that you can be introduced to their connections, but until you get to that point it's very challenging. So if I could wave my magic wand and immediately have everyone looking for that first round of connections have them, that's where I'd start.

Aaron Hurst: Very on-message, Charlotte, well done. But the magic wand opens up a whole new set of possibilities, because it doesn't have to be realistic. I think education and kids would be a big part of it. We're not really training our kids to think about connection the right way. A lot of our school system prioritizes a fixed-mindset career mentality and a certain definition of success, when the research shows almost all of our happiness and wellbeing is tied to relationships. But that's not the story we hear. We hear the story of what's going to pay. It sets our kids up for a very unfortunate and often rude awakening at midlife, when they realize they haven't been on the right track. So if we could wave a wand and have kids build those skills, and at graduation it's not "what are you going to be when you grow up," but "what relationships do you want to have, what communities do you want to be part of," that shift in narrative would do a tremendous amount. And I'd create some bug in smartphones that prevented them from being used so much. Or maybe we can't have more than one screen in a room at one time. Some kind of magical mischief.

Shamil Malachiyev: Looking back at our childhoods, we grew up spending a lot of time playing on the streets with friends, getting lost in the city, doing crazy stuff. When you look at kids today, they spend most of their time on gadgets, studying online, socializing online, playing games online with each other. With this shift toward a more remote way of socializing, do you think it's not really solving the problem of connection, and these people are still going to miss that personal connection when they grow up?

Aaron Hurst: I think it's better than nothing, but it's definitely not solving for the need. The research shows physical contact is critical. Situational humor, shared experience, the things you build a friendship on, are harder to do online. A lot of the forms of connection require being in person, knowing your neighbors, being involved in service. These generally don't happen online. Being in contact with someone on Nextdoor is not the same as actually knowing your neighbors. I don't want to say it's completely worthless or all evil, because that's overstating it, and there's research showing some of it is healthy and works. The bigger challenge is that it's all run by corporations whose business models are fundamentally tied to keeping you on there. If a company had a business model that minimized the time you were online, that's never really going to happen, because it's not where the economic incentives are. So it's that corporate incentive structure creating the problem more than the technology itself.

Charlotte Massey: I definitely agree. There's a real magic to being together in person, being able to create your own form of play that's not formally structured, and the benefits of spending time outside in the sun and the air and getting movement. It's more difficult to do that when you're always online. We also know the impacts of cyberbullying. When you put that screen between people and you're not looking at them face to face, it's a lot easier for hurtful things to be said and shared. Talking to the young people in my life, they're all terrified of some quirky, funny moment of themselves being broadcast on the internet and living there forever, which is not a fear my friends experienced when we were posting on Facebook in middle school. I'm scared for them too. That's something people in their teens shouldn't have to be thinking about.

Shamil Malachiyev: Aaron mentioned neighbors. I've noticed the same thing: 10 or 15 years ago it was easier to become friends with your neighbors. Everyone seemed warmer. Now, when you move to a new city, it's almost as if everybody's in their own problems, their own world, and it's really hard to break through and connect on a more personal level. Is that something you see in Seattle as well?

Aaron Hurst: I'm reluctant to make broad statements about it, because there are a lot of exceptions. There are a lot of blocks in Seattle and elsewhere where neighbors are just awesome and take care of their communities. So there's a wide range of experiences. Some of the trends are driven by things that happened during COVID and the general fears that came out of that. And technology is taking care of a lot of the things we used to rely on neighbors for. I always give the example: if you need sugar now, you Amazon Prime it and it's there in an hour. You don't need to go next door and ask. That lack of dependence on others, that technology takes care of, means we lose the thing we know from the research and our own experience actually builds a bond: asking for help and being vulnerable with neighbors. We don't need that as much anymore. Charlotte, I know, is a great neighbor, because she's got an amazing garden.

Shamil Malachiyev: Just invite everyone to the barbecue. That's it. Friends for life.

Charlotte Massey: That can be the start of it. We've heard from lots of people who have hosted or participated in block parties that getting everyone together, so you can break the ice and learn each other's names, can go a really long way in connecting a neighborhood. My experience with neighbors in Seattle has been very mixed. I've lived in two different neighborhoods, both times as a renter. The first time, in two years, I only met the neighbors right next to me, and it was not a very pleasant experience. They were not excited to have renters next door in their duplex. Then I moved to a neighborhood where people were much more friendly and excited to connect, but it was on me to go out and meet them. They weren't bringing me cookies.

It's a lot of effort to get to know your neighbors, especially if they might not be there long. My garden is one of the ways I do it, because it's in the planting strip between the road and the sidewalk. So whenever I'm out there, people walk by and comment on my tomatoes, and I ask their name and which house they're in, and it lets me build connections I wouldn't have otherwise. A lot of people say walking their dog is how they meet their neighbors, and then remembering the people's names in addition to the dog's names. Or asking for help. Even if you can't Amazon Prime your sugar, you can still go next door and ask if anyone has extra, or invent some other need, even if you could do it yourself. If you ask for help, it opens the door for them to ask you for help back, so you create an opportunity for mutual support, not just mooching.

Shamil Malachiyev: So with the Chamber of Connection, your main ICP is people who have cats. Basically people without dogs.

Charlotte Massey: I don't know, in Seattle I see people walking their cats fairly often too, so that might be an even bigger conversation starter.

Shamil Malachiyev: That shows the desperation in the community. People get jealous of all the dogs facilitating connections, like, my cat can do the same.

Charlotte Massey: Now maybe that's one motivation.

Shamil Malachiyev: Aaron, how did the movement come to be, from an idea in your head to something you actively decided to tackle, to look for other people to build this vision?

Aaron Hurst: I've been working in and around this topic most of my career, so it's not a brand-new field. What really stood out to me were two things. At a strategic level, I saw that this is the number-one problem in our country, and at the same time saw there's a real leadership gap at a systems level on it. For the number-one issue to have no systems-level leadership is very concerning, and as a social entrepreneur, it's also very exciting, because you've got the biggest issue and a gap right where the need is. That's a very compelling social-impact sandbox to play in. The second piece is more personal. Having moved 12 times, being about to become an empty-nester, having worked way too much in my career, and especially as a CEO, you don't generally make friends with the rest of the team the way other people do. It's a very isolating role. You have this midlife epiphany around: huh, friends are really the thing that's going to matter, and if I don't invest more time in it, we all know where that story ends. As I talked to folks, it was rare I found someone who didn't have that same story.

Shamil Malachiyev: Taking friendship professionally, basically. Making sure you put in the effort, put it on your schedule. It's not just something that happens by itself.

Aaron Hurst: Yeah, it's prioritizing it, learning how to do it, and recognizing it doesn't happen organically. There are a lot of myths about connection in our society that get in the way, including a belief in a friendship-love-at-first-sight model, where you bump into someone and it's smooth sailing from then on. That happens occasionally. Charlotte made one of her best friends on a ski lift. But generally that's not the model for how friendship works. It's recognizing the amount of investment involved and making space for it, and also just initiating. A lot of people wait for everyone else to initiate. If you initiate, you're well on your way.

Shamil Malachiyev: Charlotte, when did you realize connection was something you wanted to invest a lot of your time and energy into?

Charlotte Massey: I told you about my experience moving to Seattle during the pandemic. I moved here with my then-boyfriend, now my husband, so that investment worked out. He had some friends here from college. I knew hardly anyone, I was working remotely, and I was living in an area that wasn't walkable, so I wasn't organically going to bump into anyone. I really had to actively put myself out there to make connections, and it was a uniquely challenging time to do so. There weren't many opportunities to be in person, especially during the Seattle winter. So I realized I was going to need to be very intentional and active around friendship. I built a spreadsheet of friend leads, and I treated it like a sales funnel. I went through my list of people I'd seen on TikTok or Instagram, or had mutual connections with on LinkedIn, or had been quoted in articles with, and I reached out to all of them asking if they wanted to get coffee or do something active. A lot of people never responded. Some responded and were really difficult to schedule with. But I also had a lot of first friend dates.

Having that approach, starting with a lot of people so I could narrow down to a few I could really spend time with, helped me feel okay knowing some of the friendships just weren't going to work, and that it might just be that we were in different life phases. There were people I really connected with who were then pregnant, or about to move out of the city to a big house in the suburbs, so we just weren't going to be able to spend much time together. I was really looking for best friends, people who'd want to hang out multiple times a week, and I was able to find them, but it took a lot of activity. Even the friend I met on a chairlift only happened because I got her number and then texted her four times asking her to do things before she finally came out with me. Now we're really close friends, but it didn't just happen. It took planning and follow-through.

Shamil Malachiyev: Both of you being entrepreneurs, when you build something together, picking a partner is an incredibly important step to get right. How did you know you were right for each other building this?

Aaron Hurst: I'll let Charlotte go first. I'm curious what she says.

Charlotte Massey: I was going to say I'm curious what you say. Well, I knew I was really interested in this problem. I knew I wanted to stay in the social-connection space, and, like Aaron said, there weren't many organizations actively tackling this issue at a large scale. So my options were a community role at a larger organization, where I could create connection for a small group but not change structures or make a larger-scale impact, or starting something. Aaron is extremely experienced and smart. I saw early how skilled he was at getting important people in a room together to make things happen, so much faster than would be possible without those connections. I was also coming out of a startup I'd started in college with other students my age, and something I'd wanted in my next role was to be under a manager I could learn a lot from. So the opportunity to start something with someone with a lot more experience and connections, who I could also learn from, was one I was not going to pass up.

Aaron Hurst: Nice answer. Well done, Charlotte. For me, when I start something, I get excited about it, I go meet a lot of people, I'm aware of different needs, but I'm also looking for where there's chemistry and a clarity of one plus one equaling 6,000. Meeting Charlotte, a couple of things were really clear. One is that Charlotte's just someone to get shit done. This work is authentically what she wants to do. It's not just a smart idea. There's clearly a commitment to it. She's got entrepreneurial experience. A lot of folks interested in doing this work don't have that operating experience, which makes it really hard to actually get anything done. Despite being separated by decades, she and I share a lot of weird experiences as entrepreneurs growing up, and how that manifests, so there was a lot of similarity, but with radically different journeys around those early stages that I could really relate to. The generational thing is really important, because the primary population we're working with is at least 10, but more like 20 to 30, years younger than I am. My insight into that population, my ability to be a spokesperson for it, my network, my understanding of the brands, are all things I'd have to spend a lot of time learning. The way to do it is to have a partner who authentically breathes in that space and can lead that work, and Charlotte has that in spades. I look at what we've gotten done in Seattle, and what we hear from everyone is that no organization, for-profit or nonprofit, has gotten as much done as we have, and we've done it on a bootstrap budget. So clearly something's working.

Shamil Malachiyev: How did your past endeavors help shape you into the person now getting shit done quickly and effectively?

Aaron Hurst: A couple of things. One is that I've been working in this field for over 25 years now, plus even before then in Silicon Valley, so I just know a lot of people. One of my strengths has always been reaching out to find people who can either do the work or have the answers I need. I have no need to be the one with the answer or the one who has to do the work. Being able to use the network to get things done is something I've honed as a skill. Secondly, through the Taproot Foundation, I learned that the number-one currency for good people is creating meaning for them. They value that above money, unless they're in a very dire situation, and most of them are really starved for meaning in their lives. The ability to be part of something bigger than themselves, to do work that's actually fulfilling, if you frame it the right way, gets a lot of people excited to be part of the team. We've got over 150 volunteers working on this in Seattle alone, because we understand that doing service toward this actually makes people happier, and it's a rare opportunity to be part of something so important, as scaling and ambitious as we are. I've also been a product manager and run organizations, so I understand all the functions of an organization and can do them at a basic level. It's not always the best strategy, but there's never a roadblock in moving forward. Charlotte's very similar. We can fake it well enough if we have to, whether it's an HR, finance, marketing, tech or sales issue, and do it with enough courage to get us to the next step. It's not the long-term answer, but it's what enables short-term traction.

Shamil Malachiyev: What about you, Charlotte? I was studying all the way back to selling artwork as a kid, before Gnara.

Charlotte Massey: One of the big learnings for me has been prototyping, getting more confident putting something out there even when it's not ready, and especially when it's not fully developed, because that's how you get feedback and know what to change so you can build better next time. We've definitely been doing that with Chamber of Connection programs, putting things out there and getting lots and lots of feedback and making rapid changes, which is often overwhelming, but effective at making sure what we scale is actually going to work. In my earlier entrepreneurial endeavors I had a tendency to be too committed to the product and too precious about it. I'm also now at a stage where I realize no company or organization I'm working on is going to be my whole identity or my whole career. So if it's going to fail, I'd rather it fail quickly, so I know it's not going to be what I spend the next decade on and I can get on to the next thing. That freedom from the desperation of needing something to work lets me be more realistic about where we're at and not force something to function in a way it just isn't going to.

Shamil Malachiyev: What were some of the surprising or unexpected challenges you've encountered building the Chamber of Connection?

Charlotte Massey: A lot of the challenges have been expected, but finding product-market fit for the programming has been a bigger challenge than I expected. Our first program is our Welcome Day orientation for people new to the city, and we had a much higher proportion of non-newcomers attending than I expected. We had lots of people who were empty-nesters, or newly retired, or who had lived in the city a long time but didn't feel they had the connections they needed. Everybody wanted our product, which is great, but we'd designed it as a program for people who are new, and the curriculum focuses on peer coaching and connections between people with similarities, the similarity being that you're a newcomer. It's open to everybody across all life stages and backgrounds who are newcomers. So it was exciting that everyone was interested, but it also meant we hadn't nailed our marketing or our target audience. That threw us into wondering whether we needed to change our product, add products, or move to an application basis. We've ended up adding products. Now we have a membership open to everyone, more focused on empowering people to be leaders in their communities around connection. We also found a lot of people who wanted to volunteer, at least partly motivated by wanting access to the curriculum, but in a way where they didn't have to admit they were isolated and lonely. There's a large stigma around that, which we can somewhat get around with the newcomer persona, because of course you need connection if you're new, that's no fault of your own. But if you're not new, why haven't you done this for yourself yet? The reason is we're not structurally set up to support people, and it's really challenging to make friends as an adult. That's what our programming aims to support.

Aaron Hurst: I'd add a macro-level one. When I started working on this, the presidential election hadn't happened yet. By the time we committed, the election had happened. As an entrepreneur, crisis is great. If a tree gets hit by lightning, it's like, awesome, look at all that wood I can use. But in this case we had a forest fire, which is a very different kind of issue. It's harder to know what to do when it's charred earth in every direction. Companies all froze because they didn't know what to do. Foundations froze, trying to figure out whether to give all their money to organizations having their federal funding cut. Individual donors froze because the stock market might collapse. So everyone froze. Retrospectively it makes a good story, but there's truth in it: to a large degree, we just focused on programs and doing the work, because early on, fundraising and those higher-level partnerships wouldn't have gone anywhere. What we're seeing now, emerging this summer, is that chaos is the new normal, people are adjusting, and companies and funders are coming around, ready to talk, and we have evidence of what we've gotten done. So it's been semi-intentional, somewhat unintentional, but effective. A lot of the surprise for me has been how hard the marketing and getting to newcomers is. I thought that would be easier. I thought we could go to realtors, that companies would open the doors for their new employees, that universities would. There's a lot of risk aversion at every level to doing that. I thought social media would give us much more immediate virality, and we've had to do a lot more hand-to-hand, on-the-ground work to bring folks in. The surprise in the other direction has been how much media attention this has gotten. We've had coverage in just about every outlet in Seattle, national media interest, and partnerships with media companies wanting regular content. It's become a great content opportunity we've only partially leveraged, because the story's great. It's a feel-good story, a story of the time.

Shamil Malachiyev: What have you noticed with the implementation of AI into everyone's life? A lot of people are trying to solve their loneliness by finding companionship with AI models, therapists, coaches, just somebody to talk to, and that alleviates the need to have another person to talk to. Do you think it affects how easy it is to get people to break out of their shell and go outside and meet real people?

Aaron Hurst: For sure. There are some productive uses of AI in this area, but overwhelmingly it's not. The parallel I give is that what porn did to romantic relationships, AI is doing to platonic relationships, where a lot of that need can get met. What's better than a friend who always agrees with you, always tells you how great your ideas are, pushes you on different concepts, and is always available, even when you wake up at 4am like I do? It's pretty hard to compete with that. We've created this perfectly imperfect friend in AI. A lot of people get frustrated with real people, and it's easy to retreat into that.

Shamil Malachiyev: It's almost like a muscle. You have to get used to being okay with getting frustrated with other people, bit by bit, because they're other individuals, and that's okay. It doesn't mean it's a bad relationship. But if you don't practice it.

Aaron Hurst: Totally. It's interesting. One of my friends and I go for a walk each week, and back in the day you'd obviously check in about how everyone's doing, how's Bob, what's going on with Sue. Now every time we end up talking about what the best conversations we had with AI this week were, what we've learned, how far we pushed it. One of my friends is working on a book through it. Another is looking at different philosophy and how far to push it. It's almost become a mutual friend we talk about when we go for a walk, which is hilarious and scary to me.

Shamil Malachiyev: Maybe we should ask OpenAI to get ChatGPT to actually start connecting people. If you're in Seattle, here are my other friends you should meet.

Aaron Hurst: That would be awesome and incredibly creepy at the same time. Charlotte, are you seeing a lot of people in your social community using AI to meet that need, or is it happening underground, or do you think it's just not happening?

Charlotte Massey: I have a fair number of friends who refuse to use AI and just won't touch it, mostly in academia or working at non-profits, concerned about the energy usage, water usage, and the impact on their writing style. And I certainly have friends using AI for work and efficiency. I don't know that any of my friends are befriending AI, or at least we're not talking about it. But I'm sure it's happening in my age demographic.

Aaron Hurst: It's why I use the parallel. I think it's much more widely used than people talk about. There's a shame in it.

Shamil Malachiyev: Do you think we're going to be referring to this as an AI addiction, ChatGPT addiction, the same way men now talk about porn addiction, with people coming in groups asking how to get out there and talk to other people instead?

Aaron Hurst: It's absolutely built to be addictive, there's just no question about it.

Charlotte Massey: And without the ability to actually work through real challenges, it's hard to develop an actual relationship. But it's easy for it to be addicting, much easier than any relationship you'd find in the real world. And then you're one software update away from losing your best friend and having to retrain it to be exactly what it was before.

Shamil Malachiyev: It's a friend with Alzheimer's.

Aaron Hurst: We'll see how the business model evolves for AI. Right now it's subscription. It's kind of like what Facebook in theory was at first, which was actually about the content and the interaction, and then it became advertising. So far, subscription-based without advertising is the current model. In that model, they want you to use it, but not too much, because it costs them money for each use. They want you to use it enough to renew the subscription and give them the content they want, but they don't actually want you on it all day long. The second you introduce another economic model to AI that makes it in their best interest for you to stay online all day, we're hosed. You won't be able to tell whether it's recommending a recipe because it's the best thing or because it's trying to sell you flour and sugar. It'll know how to hook us: oh, I saw it's raining outside, you don't want to go out, I'm sure you'll come back over here. It'll be able to manipulate the hell out of us. Right now it's not intended to do that, but it's inevitable that AI business models will be built to keep you from ever leaving.

Shamil Malachiyev: Do you remember that Black Mirror episode where they'd improve their abilities but at any point in the day it would be like, hey, buy this coffee. I think in the next couple of years we'll notice our mutual friend starting to sell a lot of stuff.

Aaron Hurst: It very well could.

Shamil Malachiyev: Building something is hard. A lot of people who haven't tried building something don't realize just how hard it is. What helps you get through the moments where you get home and think, this doesn't work, it's never going to work, I'm not sure I can do this? How do you pick yourself up and get into the right frame of mind to keep going? One of my friends says success is being able to stay optimistic regardless of the failures along the way. What helps you get through that?

Aaron Hurst: It's great to have a co-founder, first of all. It's helpful to be on that journey together, so you can't spiral as much and you can put things in perspective. That's much easier than going it alone. And I'm just stubborn as fuck. Like a dog on a bone, I'm going to figure it out. If this isn't the right strategy, dump it, go to the next one. I like what Charlotte said earlier: you can't fall in love with your product, you have to fall in love with your mission, and be willing to constantly abort every product that doesn't work and go to the next one, because you're trying to get the mission achieved. It's that ability to bounce to other solutions. A lot of people get stuck on their product, which becomes really challenging. The thing that prevents me from moving forward is if I lose vision. If I don't see a path forward, even a 1 percent chance of success, all the air in my balloon goes out, because I don't know what energy or hypothesis is going to lead anywhere.

Shamil Malachiyev: Before we jump to Charlotte, it's interesting: when you haven't had 20 or 30 years of building something and failing and having it affect your self-confidence, and having to get back on the horse. I can see you've almost become numb to that feeling of, this is telling me something about myself. No, it's not, because you kept overcoming those stumbles.

Aaron Hurst: It's a lovely story. I don't know if it's true. I've gotten better at it. With the Taproot Foundation, I had a huge success at a relatively young age, and that sets the bar that everything needs to be that level of success, which creates tension. A lot of things, even if successful, don't feel big enough or in keeping with the legacy of what I've already built, so there's a lot of pressure on myself that way. As a social entrepreneur, one thing folks on the commercial side don't understand is that we don't have equity. You put in your own cash and your own time, and we never get repaid for that. As you ramp up to a mature organization and get paid something resembling market salary, you've already lost hundreds of thousands of dollars in opportunity cost you're never going to recoup. And if you don't get to that stage, you never recoup them and you've just spent three years with no income, spending your own money to make it happen, without the potential of winning a lottery ticket. In some ways it's more honest, because the vast majority of commercial startups blow up too. You should do it for the right reasons, because statistically very few things work. As you get older, there's this sense that retirement's closer, that I need to be contributing to savings. In my twenties, that was so far off, but now there's a much more finite sense of the years you have to make it happen, and you also have kids in college and all these financial things, which is a different type of pressure than I had in my twenties.

Shamil Malachiyev: Where were you, Charlotte?

Charlotte Massey: For me, a mistake I made in my first company was tying my identity so tightly to it that it made it really difficult to leave. I had to create a new identity for myself in order to feel comfortable shifting away from it. So that's something I'm paying a lot more attention to this time, maintaining my own relationships and my own activities that aren't fully tied to work, so I have better work-life balance and I'm still me. I'm not just Charlotte the pants girl or Charlotte the connection girl. And with that, making sure I take chunks of time off. I definitely have a tendency to just keep working. I can sit and work for any number of hours, but I notice my quality of work and my creativity are hit significantly if I don't give myself time to rest. When I step away, that's usually when the big ideas happen and things fit together. I've also gotten a lot better at telling when I'm on the verge of burnout so I can pull back before it happens. Some of my strategies are movement, going to an exercise class or on a walk, or doing something creative. I like to paint. Spending time in my garden is something I do daily, because I don't want my tomatoes to die, and it helps my mental health a lot and forces me to go outside. That looks different for different people, but finding what brings you back from the verge of burnout, before it happens, is critical to not spiraling into a place where you can't be productive because you're so depleted.

Shamil Malachiyev: Would you say that's the ultimate cost of being an entrepreneur, that you have to really look for that off button?

Charlotte Massey: There are lots of costs. Like Aaron said, there's a monetary cost. Most of the time you don't get a huge payout. Even the majority of founders who have exited their companies probably didn't have a lucrative exit, and you put in so much work that even if you exit with millions of dollars, you might have made that much just working a corporate job over the seven years you poured into your startup. So if you're trying to found a company with the goal of getting rich quick, there are probably easier ways, working a normal finance or consulting job. If you don't love it and don't feel like you have to do it, I'd recommend against it. Aaron and I have talked about how it's an addiction to want to build things, and I do feel that's somewhat true. Then there are the social costs. I'm trying really hard not to do it this time, but when you're working crazy hours, constantly traveling for work, and dealing with problems totally different from what other people in your social circle are dealing with, it can be really easy to get socially isolated. There was a two-month period where I decided that to handle the amount of stress at work, my strategy was just not leaving the house. That was a terrible idea. It did not work. But it was a real thing I tried. You just lose out on normal life.

Shamil Malachiyev: Trial and error. What about you, Aaron?

Aaron Hurst: It's exhilarating a lot of the time, it really is. The studies have shown that entrepreneurs generally have mental-health problems, and that's part of what drives it. It's not a rational, sane thing to do. It doesn't make economic sense, stability sense, or really social sense. It's a compulsion and a specific wiring. It's romanticized way too much, and it makes kids think it's the right thing to do, the heroic thing to do. The long odds, in some ways, even make it more attractive. It's like becoming an NFL quarterback: I know the odds are low, but I'm going to be that quarterback who makes it onto the Seahawks.

Charlotte Massey: And the stories we hear are about the people who took the big risks and it paid off: I put all my savings in, I maxed out all my personal credit cards, but it was all worth it because I made the big bet on myself and it worked out. We don't hear the stories of all the people who did that and it didn't work out, and now they're just working their way out of debt, which is most people in that situation.

Shamil Malachiyev: It's almost like we're reading stories about lottery winners. I sold everything, bought that ticket, became a billionaire, everyone should do this. And you're like, oh yeah, this is something to strive for.

Aaron Hurst: That's part of it. I've been believing more and more that there's an entrepreneurship economy, and a lot of people make money on entrepreneurs. If I think about who makes money in entrepreneurship, the entrepreneur is the one who makes the least. The higher staff get paid. The VCs generally have a way to get their money back. The company that acquires them typically gets a great deal because they need it for whatever reason. AWS gets paid for the software. Salesforce gets paid for their sales-management software. You've got your 16 different SaaS subscriptions, your lawyers, your banks. Everyone's making money off an entrepreneur before they make a penny, and the majority never make it past that stage. And who's romanticizing entrepreneurship? It's all those vendors. If you look at who's making money in AI right now, it's the OpenAIs, the ones with the platforms, not the ones actually building the stuff, the majority of whom are racking up OpenAI costs and not going to produce anything with it. But we romanticize it. So there's an economic incentive to build an entrepreneurship marketplace and romanticize it, without actually looking at the math.

Shamil Malachiyev: Do you ever get jealous of the people in cushy jobs at huge corporations, with a lot of people around them? You can go to the office anytime, there's free coffee everywhere, you don't have to pay salaries at the end of the month, deal with taxes or retention. You just do your work, nine to five, go home, have a normal life. Did you ever consider, maybe I'm doing the stupid thing here, trying to start something, all this craziness?

Aaron Hurst: That's the right frame, because it's a wiring question. My wife works as an executive. She typically leaves at eight in the morning and often doesn't get home until 10 or 11 at night. If you're wired like a striver, it matters where you work, but it doesn't matter where you work, because you're going to be ambitious in whatever setting you're in. If Charlotte and I tried to dial it in, nine to five, it would pretty quickly get annoying. We'd notice the people around us weren't really trying that hard, and that the CEO wasn't ambitious enough to want to do more. There'd be days like, this is awesome, I went to a movie tonight, how crazy is that. But I don't. I have those fantasies, but I immediately jump out of it, because that sounds so easy, and then the interpersonal shit you deal with inside companies is brutal. It sounds lovely from the outside, but the number of times your ideas get killed for the dumbest reasons, or someone's political ambitions get in the way, or you build something amazing but the company strategy shifts and it gets turned off after three years, or a sales deal you've worked on for four years falls through because of something outside your control. There's trauma in all these areas. So I'm careful not to romanticize that, being married to someone who loves her job and does amazing work. It's just not that.

Charlotte Massey: I definitely considered it. I intended to get a more normal job after I left my startup, even just to get a dropped comparison, because I started my company in college, then worked on a campaign, then at a digital agency remotely for eight months. That's the extent of my normal work experience at this point in my career. I think I could try it if it were for a shorter period and either paid very well, setting me up to do something more interesting after, or if it were truly quite manageable in workload, and then I could start something else on the side and it would give me the funds to work on my creative pursuits. It never ends with just, oh, I have an easy job. There would need to be additional personal projects for that to sound fun. And I do think it would be pretty soul-crushing to build something and not have control over having it actually exist in the world. That's the most rewarding thing to me.

Aaron Hurst: There are different entrepreneurial profiles. Charlotte and I are similar, not exactly the same, but in a similar ilk that comes out of creativity. The act of creation is a big part of what motivates both of us, and you see fewer of those people. That role is harder inside companies. There are other people who are just tinkerers, or economically motivated, and it's easier for them to make that shift. I've met a lot of for-profit entrepreneurs who are like, I'm just going to make this widget 2 percent faster, and I say, awesome, dude, go for it. They figured out a way to compress something and make it work, and it sounds like they're going to make millions, but I don't give a flying fuck, who needs that, why would I spend a minute on it. That form of entrepreneur can transition more into other areas, because their drivers are different.

Shamil Malachiyev: Charlotte, is this your first experience working at a nonprofit?

Charlotte Massey: I worked on a political campaign, which is similar, and I worked at a non-profit in high school. My first job was at an art non-profit, and I famously told the boss interviewing me that she could not find a more qualified person. I was like 16. She hired me, and I did some of the programming and the website and helped with the rebrand. So it definitely felt like working at a startup, even though the nonprofit had been around for about a decade at that point. But this is my first time trying to build a nonprofit at scale. There are definitely some things that are different, but we're building a nonprofit as though we're building a venture-scale company. So the ambition is similar.

Shamil Malachiyev: In terms of solving the connection crisis, do you think being a non-profit is more of a pro or a con?

Charlotte Massey: I think it's a pro. It's helpful to orient toward solving the problem as the primary end goal, rather than as a secondary goal to making as much money as possible. There are still economic drivers, we need funding in some form for the organization to exist, and that can look like bringing in revenue through customers, and support from companies and foundations. So in a lot of ways it's similar. But there's not the pressure to 10x revenue or shut down the way there is with for-profit, and that gives a little more flexibility to build for the longer term, rather than having external pressure to build really fast and then get shut down for not hitting revenue targets. Aaron, what do you think?

Aaron Hurst: It depends on the situation. Taking on investment is generally a pain, and something I'd prefer not to do. On the nonprofit side, people contribute and support it, but it's not the same relationship, because they don't have the same thing riding on it. They care about the impact. We just have countless horror stories of investors, which is a different dynamic. As a nonprofit you're still selling something, going to a company or others, and there's a credibility that comes from being a nonprofit, a competitive advantage in a lot of cases. It can be the opposite too, but it's often an advantage. There are parts that are hard. Typically you're selling something twice: to some philanthropic or government body, but then the product itself is for an end consumer, so you've got a customer and a proxy customer who may or may not be aligned. In a nonprofit I find I can generally attract better talent if you know how to market it, because you get people to actually give a damn. The talent I had at Taproot now runs many of the corporate foundations and is in key roles. I'd also say I'm a very unusual nonprofit social entrepreneur, in that I'm very business-oriented. I've run for-profit, I've worked in for-profit, I'm highly competitive and don't like to fail. I'm all for collaborating if it moves the mission forward, but I don't see a need for collaborating for the sake of it, which a lot of nonprofits start with. I'm willing to fail and break things, because from my standpoint things aren't working now, so if we do something that's not the right thing, it's probably not going to make anything worse, and it could create something better. I don't have that sacred concern a lot of folks in the sector have. So we're very much a hybrid, with a bit of a startup-backed mindset in some ways, though grateful not in all ways.

Shamil Malachiyev: Aaron, what would you say is the main benefit of having a co-founder with that much experience? I remember the days when I'd find a co-founder and we didn't know what was ahead of us, what we were getting into, but it was so much fun not knowing. Now, with Aaron, he kind of has an idea of what's coming. Is it much different?

Charlotte Massey: He has an idea. It's not always the right idea. But he always has an idea, for sure. For me, like I said, I spent seven years building something with a team that had about the same level of experience as me, so I was just learning by teaching myself on YouTube videos or through accelerator programs. It's helpful for my career development to work with people who have a lot more experience, not just Aaron, but the whole rest of our team. I'm learning so much about how different organizations and companies operate that I didn't know, because I was in the small apparel space, which is a very specific industry. I think I'm also getting better and more comfortable at pushing back when I think we're not heading in the right direction, or when I think something would resonate more with my demographic or the people we're working with. That's certainly a dynamic if you're working with someone who has a lot more experience than you, so if someone is deciding on a co-founder relationship, I'd keep that in mind and make sure you feel comfortable advocating for yourself.

Shamil Malachiyev: So would you say becoming more assertive was an important element for you?

Charlotte Massey: Yes, which has been an important element throughout my life, not just in this organization. Another thing we did that's helpful, and people should keep in mind when starting any organization, is that we worked together for a couple of months before deciding to be co-founders. I was helping Aaron with Chamber of Connection projects before coming on as a co-founder. That's really helpful, because I already knew how we worked together, I'd already pushed back and seen that he listened to me. Without that, I don't know that I'd have been comfortable joining, because I wouldn't have known whether I'd just be putting in a lot of free labor and getting steamrolled when I had ideas about other directions.

Aaron Hurst: It matters so much on the specific people, and on whether you're looking for someone who's truly a partner. If you're not looking for someone who can really partner, take ownership, and bring ideas you're not going to have, that's a big mistake. If you had two identical people, and I somewhat had that with my last venture, where a co-founder was very similar to me, it actually created a lot of problems. We both wanted to do the exact same work all the time, and the dark side of both our personalities amplified each other, because we'd both get excited about things we shouldn't get excited about. So having overlap with some differences is incredibly important. It's also my personality: I'm highly opinionated but open-minded. I sound like I'm so certain, because I am, but if I hear a better idea, I'll drop it in three seconds. Charlotte always had some amazing ideas, and I'd say, yep, that's better, let's go. But if someone's not the right personality and doesn't know how to engage with me, it'll sound like I'm not open to that, because I state things with so much passion and confidence.

Shamil Malachiyev: What is the culture you're trying to build?

Aaron Hurst: We haven't spent a lot of time talking about that. We've been so busy trying to figure out what we're doing. It's an area where we're actually having our first hire, we just posted a job for it, and I think it's the first time it's going to force us to have that conversation. It's been more, how can we find volunteers, how do we get this done, how do we prove it. We don't necessarily know exactly what we're going to be doing, which could shift what the culture needs to be. So it's probably something that comes to the foreground in the next three months, but it hasn't had to be yet. Charlotte, does that seem right to you, or do you have a different perspective?

Charlotte Massey: We haven't intentionally sat down and thought about our company culture, because, like Aaron said, we don't have employees right now, we just have volunteers who are amazing. There are a couple of things we know. We're a hybrid. We like being able to work together in person in Seattle, so the position we're hiring, we want based here so we can collaborate. And we want to really be supporting and empowering the people we're working with. That's something I've admired about Aaron's leadership, supporting people even if it means they don't keep working with us. There's no possession, no sense that you need to do the maximum number of hours and be dependent on the relationship with us. Instead we support everyone, making connections, doing skill-development work so people are set up to move into other roles, so their time volunteering with us is almost an incubation. That's done a lot for our core team of volunteers wanting to continue working with us for months, even when we don't have budget to pay people.

Shamil Malachiyev: You have a fantastic co-founder dynamic, and I can see that when volunteers see that, they also want to be part of a warm, friendly, supportive environment. If you could convey one message to everyone in Seattle who feels lonely but doesn't have the courage to go out and start meeting new people and being open to the world, what's the simple message you'd want to convey?

Charlotte Massey: I'd want to communicate that it's normal to be lonely in the way that our society is set up. It's not your fault. But also, you can take personal action and change your circumstances, and that's something I know because I did it, and I've seen many other people do it through our programming. You don't have to be extroverted or super skilled. You just have to say hi to your neighbors and attend events and say hi to people, and it will be somewhat scary. Some people won't be the right fit for you, but if you keep putting yourself out there, you will make connections.

Aaron Hurst: Amen. It's about empathy, and then taking baby steps and being open. One of the things people don't do enough is invite people into their homes. That's one of the most powerful ways to get started, because it shows the generosity and vulnerability to make that happen, so it's something I encourage people to do.

Shamil Malachiyev: We have to clean up first.

Aaron Hurst: I think just find things you love to do and stop doing them by yourself. Go find a way to do it with other people. We know it takes about six times before you get comfortable in a group. Commit to the six times, not the one time, so you have a chance to actually see if it's a fit. I've wanted to jettison out of groups very quickly many times, but when I sit in them, the shared experiences are a lot of what creates the value, which you just aren't going to have the first time. You have to have seen things together, or have things you can relate back to, remember that time, or know that a given joke is going to land with somebody. By definition you can't have that the first time out.

Shamil Malachiyev: Thanks so much for coming on the podcast today. I wish you all the best with your endeavor. What you're doing is only becoming more and more important in a lot of people's lives, and I really hope you turn it into a massive success, and we'll see Seattle booming with a lot of happy people spending time outside, meeting each other, spending time together, enjoying activities together, and finally ending this era of post-COVID loneliness. Thanks so much for being part of this conversation.

Aaron Hurst: Appreciate it. Thanks for having us. It was fun.

Charlotte Massey: Yeah, thank you.