Taking the Leap - Launching Your Own Community

Rachel Cossar: Everyone, and welcome to another episode in conversations in the future of work. I am your host, Rachel Cossar, and I’m really excited to have a very special episode focusing on taking the leap, building your own community, writing a ton of content, and knowing when to to go for it. And with us today is Justin Gordon. Justin over to you, please. Welcome to the show. Thanks for having me, Rachel. I appreciate it. Yeah, we I I’m just gonna go ahead and say it. There’s this like crazy dog in my building that’s just really having opinions. So you may hear him sharing some opinions in the background, but, Justin, I’d love to hear just a little bit about, you know, your your bio. Tell us, tell us a bit about yourself. For sure. I’m working on a few things.

Justin Gordon: So always always have my hands in many projects, but all kind of revolving around the same thing, which is content and community. And so right now, writing a newsletter called disco grind, sharing stories of world class founders, how they built their companies, and then building community as well with village lanes. A vetted community of startup founders and then hosting a bunch of different free events to just go grind in Los Angeles and I have an event in SF. Like, there’s always different events kind of going on to bring people together, both from the founder perspective, but also, investors and operators as well, because community is something kind of everyone craves. And I’m very focused on the in person community side of things and then using content on social media and in the newsletter to then find those people and then bring them together. And also on top of that, there’s a little bit more with just being a scout at headline, which is a venture fund based in SF and also being a venture partner at Vialis Venture Capital, because I do come across so many different founders always. So any early stage founders, always gonna have them, basically direct them to different investors that may be helpful for them. Awesome. It’s like you’re the community King.

Rachel Cossar: I love it. Trying. Great. So, I mean, I feel like some pea many people probably would love to do something like what you’re doing and and whether it’s in the community content space or just launching their own business. And I’d love to know, like, when did you know or feel like it was time to take that leap, and and go off on your own? Yeah.

Justin Gordon: I’ve taken a leap a couple different times. So it’s, it it’s always a matter of, like, when I have something bubbling up that I can’t stop thinking about, it it ends up being the time that I wanted to leave. And so for this latest one, I quit my full time job at VIZenture Capital in May of 2023. At the time, the newsletter had grown to maybe 7000 or 8000 people. I was writing that full time as well. Basically, on the side was vitalized. So, like, vitalized was very full time, but then I spent 20 to 30 hours researching and writing this newsletter every week. And I was like, this is probably not sustainable to do both. And so it kept and I did it from February until May. And then I was like, I need to take the lead because I think at that time, I had the confidence that it was growing. I had booked my first sponsor, so revenue was coming in the door. And I was like, I think I can make this into an actual business. And so for me, I always maybe leap a little bit earlier than some, but having the validation of a sponsor and then also seeing the growth trajectory of the newsletter. And then knowing the fallback was, I have, like, an MBA from USC. I had no always, always connections it’s less scary when you have a fallback as well. So I then take a leap in May of 2023 to go full time and all this. That’s awesome.

Rachel Cossar: And can you tell us a little more about you know, the the focus of just go grind and how, like, has that has the focus changed and evolved? Like, how do you how do you come up with the direction for the content. Yeah. It’s been interesting. The content has evolved a lot.

Justin Gordon: So in 2018, it was actually when I started just so ground as a blog originally in January with, like, a career focus. And so anyone who wanna switch careers is looking at what it would be like in different careers. Actually, like, I wanted to share more of those stories. So, like, someone’s a project manager or a product manager. Like, what do they actually do day to day? I was curious about that. And then in June of 2018, I had launched this podcast that I wanted to kinda have those conversations with people to share those stories and it evolved into founders specifically because I found those the most interesting of all. And then investors because I wanted to meet investors that would help founders. And then with the newsletter, the progression was I just wanted to start writing again. I hadn’t written, like, online as, like, a blogging or newsletter, like, content for myself in a long time. And so I just started writing. And then by February of 2023, I became obsessed with just this deep dive profiles because I had heard about Sam Altman from the my first million podcast. I knew who he was high level, but I didn’t know the depth, like, what’s his story? What’s his background? And the content kinda just kept evolving where I wanted to write these deep dives. I found that to be the most fascinating thing being like, what was your full story from early days to how they decide to start their companies and how they grow, how how they progress, and just found those MNC fascinating. So the content has Always just evolves over time, year by year by year, and then always kind of feel by what I’m most interested in and then seeing what the reaction from people is as well. Yeah.

Rachel Cossar: And I I know, like, what I’ve really appreciated about your deep dives is like the full picture of the person Right? I find as a founder myself, I’m constantly craving the, like, realness. I want, like, the real stories of, like, challenge and, like, how people really came out on the other end and were successful or or were not successful. Like, it’s it’s it’s helpful to know that it’s a tough journey for everyone. Yeah. I found that too, actually.

Justin Gordon: And, like, even so the deep dives and also the pockets interviews themselves, you know, I’ve done over time 400 plus podcasts across multiple shows. And it is interesting that some of the podcasts I did from the earlier days, you know, 2018, 2019, some of those founders, they’re they’re companies failed or they quit and, like, they have a job now, but other ones are like, they progressed, and now they’re running companies are doing 1,000,000 and 1,000,000 in revenue, and they’ve raised series Bs and series Cs and, you know, 1,000,000 in more funding and, like, Everyone has their own journey, but now everyone has exceeded it from that, but they’re still at it and still doing their own thing and figuring it out, which is it’s more real. It’s more human, which I always enjoy. Totally. I totally agree.

Rachel Cossar: So are there any similarities that you found between successful founders? And and and vice successful. Again, like, it doesn’t have to mean that the company itself ended up being, like, you know, rocket ship, but you know, yeah, just curious what comes up pretty. Yeah.

Justin Gordon: I mean, the first thing that comes to mind is, the YC founder, like Paul Graham always mentions, like, being relentlessly resourceful and founders. And, That is undoubtedly something that comes up again and again, both a mixture of, like, being high agency and relentlessly resourceful. That thread comes out through pretty much every founder because especially with the newsletter, I’m only studying world class founders. And that, for the most part, is they’ve started companies there. Worth 100 of 1,000,000,000 of dollars, but not 1,000,000,000 of dollars. And especially early days, even as they grow, the resourcefulness that it had, just to get things off the ground, to find customers to grow their team. The struggles that happened, I know one of them extends out. I was like, Ush Maguag from gobble. She started that company. I think she sold it for, like, multiple 100 of 1,000,000 of dollars. And she went through 4 different iterations of her business model, even killing off business models that were working. Because it wasn’t core to what she wanted to build on the end, and she had to be responsible about figuring it out. She also got screwed over by investor who kind of pulled their term sheet late and tried to lower her valuation, but like 10x, she went through a lot. And the resource from this kind of needed to overcome that and just to continue pressing on, staying true to your vision, that combination of things is a threat that comes out through most of the founders, both being relentlessly resourceful, being kind of high agency, and then sticking with the vision that they had. And, you know, it may evolve over time, but sticking with it over time, but to stay true to what they want to build, that comes out again and again and again. Yeah. That makes sense.

Rachel Cossar: I actually, Chris Savage, CEO and founder at Wistia. We had him on the show, a few weeks ago, and he said something recently on LinkedIn that was in a similar vein. Things, like, early on in their journey they were approached by, like, Hollywood and, got some, was it, like, Adam Sandler or something? Tom Hanks. And, they were like, oh, we’d love to use your platform, your video platform for this very specific use case, which wasn’t what they were doing at the time, but it would have been a huge contract and they ultimately decided to decline because it wasn’t in line with where they really wanted to be taking the company and it was gonna be a huge resource, gobbler, you know, and I think especially when you’re young as a company, you have to make some pretty tough decisions in terms of where you’re gonna put your your resources. And it I mean, I think it would be so hard to have such a, like, revenue heavy opportunity come your way. And then to decline that. Like, that that takes a lot of effort, I think.

Justin Gordon: What even come back to the original one, when y stands out, it’s like they had You know, the goal was really more around kind of the direct to consumer model of, of, like, cooking and that experience of cooking in your own meals and having meal delivery kits that they eventually figured out, but the opportunity she turned out was, like, the enterprise catering model that was making a lot of money for them. But she’s like, I didn’t get into this business. To do enterprise catering. Like, that was not the goal. And so you have to think about that always and be like, what was I actually trying to build? I’m coming across that even now with, like, Village Lane stuff. I’m thinking about, like, this online pool of building an online community for founders, and there’s plenty of online communities for founders. And right now, there’s people who have mentioned in, like, applications that they would pay for something online. But the core of what I wanna build is in person. So staying true to that, if, like, the in person connection is why I want to build this, then you know you’re sticking with that vision, it’s gonna change a lot of different ways that how that plays out. But staying with that core, I’m reminded of that from all these different interviews and deep dives I’ve written around, like, what was the core of what you want to build in the first place and staying true that over time? Yeah. Totally.

Rachel Cossar: That’s such a that’s, I think, something that, as a founder, you kind of keep on wanting to come back to, because it really is easy to get swept away. By a number of different pressures. Everyone has an opinion. Right? So so for sure. Yeah. Absolutely. So what are your biggest learnings for either the 1st year or 1st few years of, you know, being out on your own. Yeah. And there’s so many different things that have happened.

Justin Gordon: I think the ability to iterate enroll with things and experiments. I do experiments all the time for different things, and I’m I’m lucky enough to build an audience over the last few years. That’s helpful because I can get more feedback faster. But everything has been iteration. Everything has been experiments. Kind of constantly testing different things, whether it be for, like, sales outreach and different messaging or whether it be for what the content is itself on the newsletter. Obviously, there’s different people I cover and that are deep dives, but even within that, like, I played around with, like, not just listening to podcasts and reading profiles and writing, writing a deep dive from that. I’ve read full books. I’ve read, like, Disney’s 800 page biography plus another book that was on him to write the Disney deep dive. Like, that was an experiment. I was like, could I do this? Would it be overwhelming? It took, like, 2 weeks instead of 1 week. Like, those types of things in the last year have always been testing, and you figure out what works over time and also even now, like, iterating with the business model as well as another experiment. Like, I was doing mostly sponsorships for the newsletter. The first you know, year ish or so. And I was just like, not that I wouldn’t do sponsors moving forward, but I’m moving towards more of a membership model and moving towards a mixture of this kind of in person component which I wanted to be core to what I was doing. And then having the online component of the content. And so only from the last year, figuring out this, like, testing and experimenting that mindset has been super helpful in terms of, like, figuring all of this out. And then also the other thing which has been a big learning is being more public about what what you’re building, people are willing to help you out. And so I knew that kind of inherently before and had other products I’ve done. I’ve seen that even with, like, growing vitalized angels, which is an angel investing group, like, finalize, like, knowing Building that in public, people got we got buy in from people from that and founders found us with that and other members found us. Same thing would just go grind and also even with village land. Like, something that will come out soon, depending on when this is released, is I’m working on a retreat for buy for Village Lane and a founder who sold this company for, like, $600,000,000 found me through Twitter. We talked a couple times. He’s gonna speak at this thing and then also, like, just willing to help people. So I wouldn’t have found them without being public about what I’m building and then also asking for help, which a lot of founders struggle with. I don’t struggle too much with it. I’m realizing how beneficial it is. Even with him, I was just asking for his feedback on stuff. And then he wanted to help more because I would just implement what he said. So Right. This is now less than from this last, like, years. It’s like, you’re asking for help side of things, the experimenting, all that’s been helpful for me. That’s awesome.

Rachel Cossar: And it’s interesting to hear you talk about how so much of that help and support has come from the online community, even though, you know, the in person community is what you’re really looking to build out. Yeah.

Justin Gordon: And those deeper relationships, though, I mean, they a lot of things, especially now, just think about how work is operating now, things that start online and then end up in person. Is, like, another depth. So an example, again, for Connex, when we’re recording this, yesterday, I had a dinner dinner with headline venture firm. And I’m a scout for them, and they had brought all their scouts together. That started from them reaching out through LinkedIn because they had found the newsletter had found value from the newsletter, Nua heads, audience of founders. Then they were like, we’re just starting the scout program. We’d love to have you be part of it. And then eventually, this is, like, months months later, they’re like, now we’re doing a dinner for all scouts in LA. So, like, the online, the the, like, the online, so, like, in person, like, funnel is very real if you kind of nurture that. And then it does deeper relationships to all these people because even there, There’s a bunch of people from, like, Twitter that I’ve never seen in person, that I saw the in person the first time in this dinner. Now we’re, like, following up and now we’re having calls. So Like, that’s an interesting thing to see as well. Totally. I’ve found that a lot.

Rachel Cossar: I mean, I think we both shared in a digital nomad experience. At some point during the pandemic. And Yeah. And it was really fascinating to activate different cities and get to go to different places where you did have some of those online communities and connections and get to meet people in person while you were there, that was such a cool experience. And I would imagine that it’s just gonna continue to it’d be like that. I think they will crave it.

Justin Gordon: I mean, for sure, that’s something a lot of people kind of have experimented with the digital nomad side of things. And I did that. I went to I actually went to your city. I went to Boston. I went to Minneapolis. I went to New York. I went all over during the digital nomad thing, and, like, Chicago I’m more like me, West And East Coast because I’m on the West Coast. And I always reached out to people from, like, Twitter or from the news that, like, I’d have a newsletter at the time, but from Twitter, that I wanted to meet up with in person, and it was, like, it was tremendous. And then you go meet up in person, then the next time you’re engaging online, I was more engaged as well because, like, I know them. I actually met them. It’s a whole different level as well, which is interesting to see how that kind of goes. Totally.

Rachel Cossar: So switching gears a little bit and focusing or kind of, yeah, following that thread of this new world of work and and all that. What trends have you seen, either in different companies and startups that you’ve you’ve seen and are connected to that you think are net benefit when it comes to this new world of work? Yeah.

Justin Gordon: The thing I’m, I mean, obviously, I’m very biased towards in person and figuring out what this looks like, but even, like, recently, I think I tweeted a poll and wanted to see where people were working from. And 73% I think was working from home. And then, like, 14% was you know, working from an office, then people working from co working spaces and coffee shops. I know that I’ve realized we invested in ground floor, which is like a co working space, but more of a community thing. People are craving community, and I talk about to a lot of founders, and that’s for sure what they’re craving. Even this morning, I talked to someone, and they’re, you know, interested in Village Lane. I was like, why they were saying it’s, mostly for the community piece of it and, like, the in person connection. So in terms of future work, it’s like, how do you build that with your employees? How do you build that with even your partners and stuff. I know a lot of VCs host events to get to know founders and other service providers and everything. Same thing with if you see the companies like, like, Brex doing Brex dinners and, that is the same type of thing at work. Like, people are trying to get together in person. And with people, it’s a drive business. Drive connection between employees, between pension partners. I think that’s gonna only continue. And so coming out of the COVID, you know, 2020, 2021, all of that, it seems like an even more a bigger pull. And then because people are working kind of from home or working remote, they’re trying to find more and more ways to combat that and just in terms of, like, how they find connection and and purpose and meaning. And so even the company like like Marco experiences, I think they’re doing a bunch of like, organizing your retreats for companies, and they are crushing it. And I looked at them for my own stuff, and I think that’s gonna be interesting. So more, like, retreats in connection in this world of remote work because you can’t just be online forever. I think you need to see people, whether it be, you know, quarterly or annually or whatever it ends up being. So I think that trend will continue. The interesting piece, though, is then all this, like, real estate that was for offices that is now maybe empty or partially empty a lot more of the time. What does that become? In work. And so I don’t know if that becomes more community spaces. I think that could be part of it. Yeah. That like, a co working ish type of thing or some other use because of this trend in future work that is, like, what I’m curious about because I’m seeing that, like, these spaces as well are open. And I had someone I talked to in, who’s in Vancouver, who they just reached out to offices that are open on weekends to co I do co working stuff. And because they’re empty. And it’s just like, what does that look like for work? Is there opportunity to do something there too? So there’s a lot of different things in in work, but I have community in in person. Yeah. Definitely.

Rachel Cossar: I think there’s what I’m always curious about is that level of intentionality in terms of how and when and why people gather. Right? Cause I do think that there is a lot to be said for having the flexibility of being able to work remotely and be taken seriously as a professional, but coming into an office, you know, should be more than just coming into an office to be on video calls all day. Yeah. We’re seeing a lot of that with some of these kind of like the larger companies were just like, yep, you’re just back in the office. You know, I have a colleague, or a friend of mine who works at Fidelity. And she they’re required to come in, like, 1 or 2 weeks a month. She’s the only one on her team who actually is in Boston. And so she’s like, literally, she’s like, I come into the office and then I sit in one of the silent phone booths because I actually, like, don’t wanna be disturbed. Yeah. And then I connect over video with the rest of my team who are all over the country. And you’re like, wow. Like, that none of that makes sense. No. That’s not the office. I think people experience people want.

Justin Gordon: Oh my god. Just solving that.

Rachel Cossar: You know, the other thing that I saw today, and I haven’t done my own research into this, but I’m curious if you’ve heard something similar. It’s not good. But apparently, some companies are like calling people back into the office in a slightly more aggressive way trying to get people to, like, try to weed out people who wanna just quit so they don’t have to fire them.

Justin Gordon: I’m not gonna say knowing how much severance can be. Right. It makes a ton of sense, but it’s, like, basically, this revolt, right, of, like, what what happens then. From employees. Yeah. We’re not just gonna change companies. It’s just, like, pretty clear. And, like, it also a thing of, like, from a talent perspective, like, your top talent, what helps them stay, and what helps them stay happy, and then what helps them do their best work and all of those things. I just finished writing a deep dive on, founder of Patagonia. And them having, like, a childcare facility early on for, like, 1 of the first corporate childcare facilities and having all these things that, like, it’s obviously very mission driven company, but even besides that, like, like, to the core, they’re helping their employees and everyone else. And that obviously makes people stay, and their wellness is, the best places to work. So if you’re gonna stand out as a company, how are you thinking about that for your employees? And given the work environment where it is maybe flexible and remote, also one of those things where it’s like, you do have to stick to your guns, though. If you wanna build an in person culture, cool, but you have to especially, you know, freaking, like, restart that and you don’t already have that. You’re gonna lose out a lot of people, but then you will attract people who want that, which is fine. It’s just, like, can you can you survive through that turnover if you’re having already switched over? Or if you’re starting from scratch today, knowing what kind of culture you’re trying to build is important. Are you trying to put in person? Are you gonna be remote? Like, I think about beehive coming in that’s crushed it. They’re, like, remote from the beginning, but you have other companies who are doing it. Like, obviously, if it’s more deep tech and, like, in person’s gonna be the thing, it makes sense. That’s what you’re building. So septic thing about that as well. Totally. Yeah. The more intentional, I think, the better.

Rachel Cossar: And and being able to design something that might be flexible. So that you can meet multiple needs at the same time. But I’m no no no one size fits. I’ll answer. That’s for sure. Yeah. For sure. Awesome. Well, Justin, thank you so much for joining us and sharing your insights. Where can people find you connect with you, follow your work? Yeah. I’m most active on Twitter, probably.

Justin Gordon: So Justin Gordon, 2 12 on Twitter. Otherwise, jiscogind.com is where I have more of the. And then villagelane. Io is where I’m doing this better community for founders. Awesome. Great. Well, thank you so much.

Rachel Cossar: And as always, thanks to our audience for tuning in. See you next time. Thank you.