Newsletter-driven Entrepreneurial Exploration with Corbett Barr
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Brian Casel: [00:00:00] Hey, it's Open Threads. I'm Brian Casel, it's my podcast. Welcome to it. Back on the show today is Corbett Barr for the next half of our conversation. You know what led me to invite Corbett on the show is because I'm a subscriber to his fantastic email newsletter. And I noticed that he's been picking up the frequency, picking up the steam with what he's been writing over there. And clearly he's in this exploration mode where it seems like whether he admits it or not, it seems like he's gearing up for building what looks to be like his next entrepreneurial chapter.

And that's exactly the type of moment that I love to invite folks on this show to hear what they're, you know exploring what they're thinking about. Taking what they've learned in previous businesses and maybe doing things a little bit differently this next time around. I love to kind of hear that kind of stuff in real time. What was really interesting is how [00:01:00] Corbett returned to his go-to creative muscle, which is writing. And how he chose Substack as his newsletter platform of choice to move into this next chapter and explore things with his audience. Lot of really interesting stuff.

Today's show is brought to you by ZipMessage. That's the product that I work on every day. It's a tool for asynchronous communication with your clients, your coworkers, or anyone else, your audience. I'll tell you a thing or two about that later in the show. For now, let's talk to Corbett about using a newsletter to explore what's next.

Talking to Corbett Barr here back on the show. You know, in the last episode we were talking all about your past life on, on the internet through building Fizzle. You know, multiple podcasts and blogs, and then you sort of like reset your social media and blog content, cleared it all out, started fresh, took a big hiatus. We talked all about that in the last episode. What I'm [00:02:00] interested in, and the the reason I invited you on is because it seems like, you know, I'm, I'm a subscriber on your email list and I see you actively writing and sort of exploring in public what you are building into and, and whatever your, your next entrepreneurial chapter will be.

So, your site is @CorbettBarr.com, of course we'll get everything linked up. It looks like you're hosting your content and newsletter on Substack. Where are we at today as we, so we're talking here at the end of November of 2022. Yeah, give us like a state of, of things of, of landscape on, on what you're working on, what you're focused on right now.

Corbett Barr: Yeah. So as we, as we talked about last episode, I, I sold the business that I'd been running for 10 years and that really left me this like unique opportunity to have a completely clean slate and to think about what I wanted to do next. And the more that I thought about it, the more I recognize that I really didn't know specifically what I wanted to do next, but I also really missed some of the [00:03:00] early days of when I started working online. And that was, you know, really when I started blogging way back in 2009.

I just loved those, early days of only worrying about writing and connecting with people and sharing ideas, exploring themes and so on. And, you know, that that building in public process to me is really just about pulling back the curtain and being honest and transparent and vulnerable and letting people in to know where you're at, even if you don't know where you're at specifically. And so for me it's about writing and then organically seeing where it takes me.

At this point, you know, I think I probably will end up writing and podcasting again, starting a new podcast. But after, you know, having run The Fizzle Show for 380 episodes over the course of eight years, I just wanted to take some time to myself, just to like, let things grow slowly. I'm not in a hurry for any reason. I'm just going to [00:04:00] write and connect with people and enjoy that and savor that moment for a while. Because I think a lot of us are in such a hurry to move on to the next thing. You know, especially if you're, your income is dependent on this and you're trying to grow an audience and create a product and so on. I have a bit of luxury to do that more slowly. And so I just wanna make sure that I am doing it for the right reasons and that I have my eyes open and that I'm enjoying what I'm doing.

Brian Casel: You know, you've talked a few times now about this hiatus. I'm curious, like, actually, like what was like the period of time, was there a a point in time? I, I'm guessing it was sometime in 2020 when, when you sort of had the clean slate, but like.. Where you literally stopped working and your, and your day-to-day just completely opened up. And then how long of a stretch of time would you consider yourself in a hiatus? Cuz I'm, I'm curious to know like during that time what were the sort of ideas and, and explorations that you were thinking through? You know..

Corbett Barr: Yeah. I, I haven't been fully on a hiatus. I mean, [00:05:00] you know, I'm, I'm just not that kind of person. I can't idle entirely

Brian Casel: That's why I ask about it cuz I could never imagine actually not working. . Like, I don't even know what that would be like.

Corbett Barr: No And I I think you know for me taking a hiatus from content creation is really what it's been.

Brian Casel: Right.

Corbett Barr: But I've been plenty busy with other things behind the scenes but that is a pretty serious break. You know I think having your brain wired into constantly thinking about what am I going to create and and how is this going to affect other people and responding to them and so on. It it takes a lot of energy and focus. And so I knew that after ending The Fizzle Show and after wiping the the slate clean with my blog posts and social media and so on that I needed to take some time off in order to regain the energy and mental clarity that it would take to do it again.

Brian Casel: What kind of, what kind of other were you getting into? Like, like consulting or software or, or anything like that.

Corbett Barr: Yeah Over the past couple of years I've been involved with a company called Sounds True which is a 35 [00:06:00] year old publisher of mindfulness, meditation, Eastern philosophy that sort of stuff. Founded by a woman named Tami Simon in Boulder, Colorado. And they represent all kinds of authors that you've probably heard of, people like Thich Nhat Hanh, Wim Hof, Eckhart Tolle, Brené Brown, you know, hundreds of others. You know, they're not really in the space that a lot of us in the entrepreneurial circles and social media and and content creation would know but they are an incredible publisher. And they have this like amazing stable of authors but they're not very technically savvy.

And it turns out that a woman I had coached six or eight years ago, on writing a book and getting her blog established, ended up becoming the chief business officer at this company. And one thing led to another, I had started a SaaS platform for communities a while back called Palapa. And she brought me in for some light consulting because they were kind of stuck with their technology pursuits. And I [00:07:00] ended up taking on this project to launch a new platform for them called Sounds True One which is a lot like Fizzle was. It's basically live daily classes, an archive of on-demand content, community, and content that you can purchase like audiobooks, eBooks, and so on. All in one package that is both on the web and on mobile.

And so, to do this I've grown a team of software developers, product developers, designers, all that sort of thing and built that over the past couple of years. And it's been like, in some ways, similar to what I've done in the past but in other ways very different. It was the kind of thing that it wasn't necessarily easy, but it was in some ways easy for me to find the energy to do it because I was able to draw on what I did before I was an entrepreneur and when I was a consultant way back in the day working at the Fortune 500 companies. So I was able to put on a different hat.[00:08:00]

Brian Casel: Yeah, I could see how you could like, draw on all your previous skills and like, you, you'd be like the perfect person to come in and, and build a, a community based thing for a company like that, right? But I'm curious to know, you know, you've been a, a founder, a business owner all these years, and then you, you spend this time sort of away from the spotlight, like quietly in this kind of deep consulting.

Like, like what was transition like? It, I wonder like, was it kind of like refreshing to sink your creative teeth into something where it's, it's not your own business. You're, you're working with this other team but it's still interesting, like, can you speak to that a bit?

Corbett Barr: Yeah It's it's both. I mean it it basically was an instant opportunity for me to create like a mini agency in a way. On my staff now, for this consulting entity that I created out of thin air, we have like 12 people working on this project. So there was some entrepreneurial piece to it but on the other hand the company which is 35 years old and has an amazing founder who was really[00:09:00] open to tapping into my skillset and experience and knowledge as really a a true consultant. But then I was also able to tap into feeling like part of a team again as opposed- a big team -as opposed to you know just being a founder with a couple of employees around. So it was refreshing and it was the right time because it was during the pandemic and everything was kind of up in the air anyway. So I'm really thankful for it. It was it was a nice kind of diversion and way for me to stay occupied without getting too existential about what I wanted to do my own entrepreneurial journey next.

Brian Casel: I, I sometimes look back on.. The last time I was actually like employed by a company was 2008 or I I, or 2007. I, I went self-employed in the beginning of 2008. And I literally remember this feeling of, and I worked in a web agency in an office in New York City, like stepping out of the office and going home [00:10:00] at five o'clock, you know, getting on the train, like the mental freedom of like that separation of like leaving the computer. Now I'm on my own time, you know?

Corbett Barr: Yeah

Brian Casel: I literally don't, I haven't experienced that in the last you know, 14, 15 years because all of my work since then has been on stuff that I personally own. So even if I'm not at the computer working, I'm still thinking about it on a, on a Sunday morning or, or on a vacation or something. Right? Whereas before it was like, I didn't have to think about it. It wasn't.. I don't know. I don't know what made me think of that, but it seems like this is obviously a much larger thing, and you grew your own team for, for this, but it seems like a refreshing change of pace.

Corbett Barr: There there is some of that and I think part of it just comes from having a lot of people involved and knowing if you relax and trust that you can rely on other people to pick up the slack when you're on vacation or whatever it is that you want to do. So that that part has been nice. It is, in some ways, less stressful or stressful in different ways. Which, which is nice because you can [00:11:00] let that entrepreneurial part of you relax a little bit while you're focused on this this other consulting mode thing.

Brian Casel: Yeah. So I mean, you know, you picked up the writing habit again, and, and started sending to the list, and.. That seems like it's just like the natural muscle for you that you're, that you're getting back into. Right? So what are you thinking about exploring? What, what's getting you excited about, like, the potential?

So you did move to Substack, which is interesting. Can you talk a little bit about that? I mean, it seems like there's, I don't wanna get into like, reviews of different tools here, but like.. I do hear a lot of people like questioning, like, should I, you know, people who want to start a content-based, newsletter business or, podcasting business. The decision to go to Substack versus like hosting it your own or, or you know, building out something else like

Corbett Barr: Yeah And I I had a lot of conversations about this because you know been using email for business for like 15 or 17 years, something like that. And so there are definitely a lot experiences that I've had and considerations and also I know people in this space. [00:12:00] The founder of Convert Kit is is a friend of mine, Nathan Barry, and he offers newsletters through his service as well. And then there are other choices to make.

For me, moving to Substack was really because that's where the energy is right now, there's just so much momentum on it. And also because they added something to email which which didn't really exist before, which is discoverability. They've made it so that there is like a a leaderboard of most popular Substacks, there are places that you can go to search, you can recommend other Substacks from yours. And so there's this network effect happening on Substack and you see some people at the top end of the pyramid growing incredibly quickly. Some people are adding, literally, tens of thousands of people a month to their Substack because they're being by so many others.

So, it it's turned into a bit of what you've seen in social media, with Twitter and other things, it's just become easy to organically grow through the platform. And because I was bringing my own email [00:13:00] list that meant I had a chance to crack the top 10 or top 20 in certain categories to begin with, versus if I just continued on my own then it's you know up to really word of mouth and uh SEO to drive traffic your way.

Brian Casel: Interesting.

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Okay, back to the show.

How about like the, the creative process for you right now, finding things to write about? I know you, you're writing a lot about the, you know, creative entrepreneurship starting things from the ground up as a creator. I know that's a big focus for you. I mean, you know, correct me if I'm wrong, I'm seeing a lot of parallels with the focus of Fizzle [00:15:00] and the types of people and topics that you were speaking to then. I know that wasn't just you in Fizzle, but what are you sort of like exploring in terms of like topics? Are you approaching this like this could grow into a business or, you know, or community or something? Or is it really still just like getting content and ideas out there and just as like a, a way to express yourself?

Corbett Barr: Yeah I mean of course like in the back of my mind there's always.. I always think of anything I'm working on as a potential future like business pursuit. However in this case I didn't want to put any like timelines or constraints on it. I also didn't want to box myself into a particular topic in case I started exploring ideas and and felt like there was something that I wanted to you know pursue instead or in addition to. And so the the title Starting Things really was meant to be kind of a nod to entrepreneurship, which is my foundation, but also open enough that I could write about [00:16:00] other things if I want to.

So you know so far I'm really interested in, of course, self-employment, entrepreneurship, the creator economy new media, decentralized employment, freelancing, all that sort of stuff. But I've also always been really interested in the psychology of working for yourself and the personal growth that happens when you have to go like build your own business or support yourself in some way - whether that be freelancing or or through entrepreneurship. And so I'm weaving those things in and I don't think that's necessarily completely unlike what we did at Fizzle but I'm leaning into that more.

Brian Casel: I just gotta say, you, you just said a phrase that I've never heard before, decentralized employment? I mean, I never thought of it that way but I could totally see the connection now. I mean, obviously decentralized whatever, finance and Web3 and all that that, that we see today. But freelancing and consultants and creative [00:17:00] builders in our circles, right have been around for decades.

And, and I think about the teams that I've built, they've always been quote unquote decentralized people, right? You can call them contractors, but like, I've always built teams with long-term, like multi-year. I consider them very much to be day-to-day team members, but they might only be working on my stuff three or four days a week. And then they have their own stuff outside of that. Maybe other clients, their own, their own business, whatever it might be.

And there are so many talented people who seek that out and they, they need that. They have families, they travel, whatever it may. Decentralized employment is such an interesting way to, to put it. I like that.

Corbett Barr: Yeah. and I I think, like you said, there are a lot of people who want that. They want the-

Brian Casel: Yeah.

Corbett Barr: -freedom of working for a couple of different projects at once and being able to maybe turn it off when something comes up so that they don't have to work as much. And you know it was it was um really interesting to hear as Elon Musk was [00:18:00] firing whatever it was you know 75% of Twitter's workforce employees. Then you came to find out that he also let go of 80% of the the contractors and that they had I forget the exact number but it was like 4,000 contractors. And so you know that that represented half of their organization or something at that point.

So there are a lot of companies out there that do rely on contractors and I think.. You know maybe there was a time when it was kind of a a dirty word or whatever but I think now it's to the point where you can build a career around contracting. Especially if you have an eye towards building something that is your own that's a little more stable. Because you know it it's tough to to fund your startup or your business idea entirely from your own pocket and so if you're able to do some consulting a few days a week, work on your own thing, grow your own thing up until it's sort of supporting you and then use contracting to bridge the gaps. It's just a a really interesting model [00:19:00] for the future I think especially as you know so many of us get burned out on working for the same company for for very long.

Brian Casel: A hundred percent. And it's also sort of a win-win for, for like a bootstrapped business. Who wants to get some of the best talent in the world, but can't afford that talent full-time. Right? But, but three days of a really talented person a week could, could be a huge value for a business, right?

Corbett Barr: And a lot of times you can get the impact that you need or you know or the majority of the impact from having someone around a couple of days a week. Because they're really just giving you their specialty. And you know they can do that in a couple of days and you get the value.

Brian Casel: Yeah, yeah, for sure. So maybe like echoing what we were talking about in the previous episode a little bit. Things that you've learned from past experiences, building up community-based and content-based businesses to what you're starting to explore now with, with your own newsletter and writing. Potentially growing into [00:20:00] community, content based business stuff. Is there anything that, that is like a definite, like, I will do this differently this time, or things that you consciously want to avoid or just do things in a different way?

Corbett Barr: Yeah One of the things is I'm trying to be very conscious of my energy levels and not forcing output too much. You know, consistency is important but at the same time consistency doesn't matter at all if one day you just stop because you you overdid it or you burned out. So, I'm intentionally putting plenty of time off on my calendar. Reserving days where all I have to do is write, you know, something like the entire day basically. And if I finish great I can move on to something else but otherwise there's no pressure for me to try to wedge it in between a couple of things.

So, really just giving it the space to breathe and then also really thinking about following my curiosity instead of, you know, people get so focused on following your passion..[00:21:00] I think it was Liz Gilbert who, you know, said that you should follow your curiosity instead. Takes the pressure off and most really interesting projects come from just diving in and and understanding something.

And so for me the curiosity right now is where is content creation today, versus what I knew from writing online you know 10 years ago or from podcasting in there ear early days. Where is it today and what are people craving and and what what are people tired of. You know, I think there's there's so much content out there. It's a lot different than it was when you and I started, you know, 13, 14 years ago. I'm trying to be very cognizant of creating signal instead of noise and not just building something for the sake of capturing people's attention, but instead trying to be the thing that is worthy of people's attention because it's thoughtful, it's calm, it is in depth and not just surface level like you [00:22:00] see so many places.

I mean there's so many so many newsletters that, you know, I I guess I get a little something from but they're just so surface. When you think about The Hustle and Morning Brew and, you know, all of the the daily or or frequent newsletters that are just like bullet points. It's playing into the fact that people don't have attention spans anymore obviously because it's bullet points. But at the same time like after getting off of social media I I feel like my attention span has gotten better and so I want to lean into that and not accelerate the destruction of human attention.

Brian Casel: Yeah. I am kind of curious about your creative process. We'll, we'll start to wrap up on this, but like.. You know, cuz this is something that I've struggled with, especially in in more recent years, I was much more consistent about writing, you know, full articles and newsletters and tweets and, and things. And recent years I'm much more focused on designing and building software products. So all my creative energy goes into that and I don't have the time or frankly the [00:23:00] interest in spending hours to research and edit and like come up with truly unique insightful things that are, that are really worthy of putting out.

And I've now settled on like podcasting. That's the, that's the thing that I can do where I can just show up for an hour with someone, or Jordan, my co-host on the other show. And hand it to an editor, and then I can go back to work on software. Right. Like how do you think about like, planning the next newsletter, the next interesting idea that that's worth your reader's time? Like how.. I guess I'm curious to know like how much background research, note taking, exploration, before it actually gets sent and published?

Corbett Barr: I would say you know everything that I publish is is between like six hours and two full days of work and that's a lot, right? That's a big commitment.

Brian Casel: Mm-hmm.

Corbett Barr: And I I expect that I'll probably get in a bit more of a groove and and become more efficient at it. [00:24:00] But for me right now a lot of it is about exploring my thoughts because nothing crystallizes what you think about something more than writing. In fact, I don't think you can really know what you think about something until you spend that amount of time researching, writing down, you know, explaining things, synthesizing information. So, you know, it depends on what I'm talking about but whether it's like, what's wrong with social media, that took me several days to write. And really just helped me get to the bottom of what I think about it. And then it also made me make major changes in my life. And so I'm hoping that more of the articles that I write will do that.

So my creative process right now is just really following what interests me and then diving deeper and deeper into it. The what I'm gonna work on next I think is um decentralized social media, Mastodon that sort of stuff and really get beyond the surface level and and try to understand for myself like [00:25:00] what's going on there and what the future will be. And so there could be opportunities that come out of that or it could just be that maybe I live a little longer and I stave off dementia because I spend more time thinking about things. I don't know exactly.

Brian Casel: As they say uh, you don't really know what you fully think about something until you have to like, write it down or teach it to someone-

Corbett Barr: Exactly.

Brian Casel: -or, you know, get, get your thoughts on a page. I, I've certainly seen that myself. I mean, I've actually gotten to a point where, I think in the years past I was much more a writer and now I'm much more comfortable on, on a podcast.

Corbett Barr: Mm-hmm.

Brian Casel: And that's how I get my thoughts out. Even if it's like private voice notes or voice like journal to myself just to like speak it or, or like a, a small group friends and advisors, I might send them an audio message. Because when it's swirling around in, in my head or just things that I observe on social media, it, it sort of just all doesn't make sense. But when I have to like, verbalize it and make a point or make an argument in some way and the same way if, if you're writing it. You know it, you have to make, make sense for the reader, [00:26:00] which makes sense for yourself. Right. Interesting.

Well uh, Corbett, I mean everything that you're, that you're writing and creating is, is interesting as always. I can't wait to see how, how this chapter sort of evolves for you. I'll, I'll keep watching and reading. Well, thanks for, thanks for doing this.

Corbett Barr: Thank you so much, Brian. Appreciate it.

Brian Casel: All right. Take care.

Well, that wraps up today's Open Thread. Hey, tell me what you think. I'm on Twitter @casjam, and right after that, head over to iTunes and give this show a five star review. Really helps it reach more folks like us. I appreciate it. Talk to you next week.