The Shippers Ep 002 with Kevin Alexander

S03 - The Shippers
S03 - The Shippers
The Shippers Ep 002 with Kevin Alexander

The Shippers is an interview series featuring alum who have completed at least one cohort and published at least 26/30 days during it. You’ll meet a new creator, hear how Ship 30 impacted they create online, and what they took away from the experience.

Today we meet Kevin Alexander, a music lover and aviation aficionado. We talked about:

  • how Kevin decided to write about music and aviation (and which does better)
  • what it was like growing up in Portland in the late 80s and early 90s and seeing bands like Nirvana before bleach and Greenday at a 15-person matinee
  • joining out of solidarity with is kids in the pandemic lockdown
  • using “prep the page” in combination with “1-3-1” every day (even when not publishing online)
  • how it is important to worry less about trying to keep up in Ship30 and worry more about making one real personal connection
  • why if you’re in love with the idea of writing more than writing itself, maybe you should sit Ship30 out
  • Kevin’s project to review 100 new-to-him records in one year (check out his substack about music)

If this interview helps you decide to jump aboard a Ship 30 for 30 cohort please consider signing up with this link as it helps me cover the (admittedly small) cost of putting these together.

The following transcript is machine-generated by and cleaned up using It isn’t perfect, but it is as good as it is going to get.

Introduce yourself and the main topics of your writing

Tim: All right, so it’s rolling. We’re rolling. Um, okay. And that means that if you could start out by introducing yourself and the topics that you like to write about online,

Kevin: I’m uh, sure. So I’m Kevin Alexander and I write about music primarily and also aviation.

Tim: Yeah. Sweet. So talk, talk a little bit about that. That’s not the most obvious combination of topics. Where’s the, where are the threads that got you to center on those for your writings?

Kevin: So on the music side, um, I’ve been listening to music since I was a little kid. Like we had a stereo, we didn’t have cable for a long time. Um, but we did have a stereo and just a whole cabinet full of records. It was almost a stereotype. Um, and so I would just listen to those for hours at a time. Um, and then I was really lucky. Um, a lot of the kids in my neighborhood were either older or had older brothers or sisters yeah. They were off at school. And so they would bring back cool music.

Tim: Yeah. Right. Um,

Kevin: You know, I was always that kid, we were always passing music around. I was that kid making mix tapes for everybody. Um, you know what I mean? And like

Tim: High Fidelity.

Kevin: Yeah. Kinda <laugh> Um, and then we were really lucky because we were in Portland, which is right on, your freeway, interstate five. And so every band came through sure. Um, you know, either on their way to LA or on their way to Seattle or whatever. And so we saw everybody and at the same time everybody heard about Seattle sound and, you know, Pearl jam and

Tim: All this. Yeah.

Kevin: Um, Portland had its own scene and it felt like, you know, in the late eighties, early nineties, it felt like every, there was a new band every week, you know, every block.

Tim: Yeah.

Kevin: Um, and so obviously that was a huge wave. And then, um, just kind of kept, you know, that part kind of, you know, I kind of grew out of that, but, uh, just kept going.

Tim: Yeah, no.

Kevin: Yeah. And then, um, on the aviation side is less exciting.

Tim: <laugh>, that’s what I,

Kevin: Yeah. When, you know, when I was 22, I got a job in an airline and I haven’t left. So

Tim: Like the same airline, like you you’ve kind of stayed in the family of whatever airline you’re in.

Kevin: Yeah. So I got hired at, uh, Northwest airlines and, um, now it’s Delta, we merged with Delta about 10 or 11 years ago. And still there

Tim: I’ve flown Delta. And, um, I don’t know if this is interesting to you at all, but as the former CEO of the company that I work at, which is red hat was, uh, I think he cut his teeth at Delta.

Kevin: He did.

Tim: Yeah. So he, he was part of, I don’t know if you were there for that stuff like that, but we kind of heard a bit about like, I don’t know what the, they called it a turnaround effort was like, or whatever, but then, the kind of reorienting of Delta around a new approach or something like that, such that, I mean, that’s kind of the nice way to say it. And I, I don’t know if the experience of that was like something, something that should go ahead.

Kevin: Um, I wasn’t there yet. That was pre-merger. But the story we got and I can’t, his name is escaping me. Yeah.

Tim: Jim, Jim Whitehurst is his name

Kevin: Jim Whitehurst. Yes. So the idea was the story we heard was that he was sort of position to be the CEO or was kind of the CEO in waiting, um, the, he apparent if you will, and he got sort of boxed out and that’s why he left.

Tim: Yeah. Bummer for him, I guess, that these things happen <laugh> and he didn’t, he didn’t do too bad out of, uh, what happened after that. So I guess we don’t have to feel too bad for him. Yeah. <laugh> um, right. The one question I had about the music thing, I know that Seattle and Portland are not the same thing and probably not the same thing, but, I also reckon that they were probably close enough that you might have had opportunities to see like Nirvana and, uh, bikini kill and some of the kind of rock bands that came outta that era, that time in that place. Is that a true fact?

Kevin: That is true. Um, I saw, I saw Nirvana. I was lucky enough to see them, uh, the first time right before bleach came out, um, because they said they were playing songs off their new album or next, you know, record coming out and it would turn out to be bleach. Um, and then I saw them again a little while later, op opening for Sonic youth. And, um, <affirmative> maybe the red hot chili peppers I’d have to look.

Tim: So their trajectory

Kevin: I saw ’em really

Tim: Between the, their trajectory between those two, um, concerts had already started to go pretty, pretty crazy. Eh,

Kevin: They were already going, yeah, it was going straight up. Yeah. So, um, and it was great. I mean, um, there was a PLA, there were two or three venues downtown that, you know, were probably the size of a studio apartment, but they were fantastic. And we would just go all the time and see dance, um, ever clear as a Portland band. We saw them, uh, I saw green day, uh, at a mat, a show with about 15 people that were prom dresses.

Tim: <laugh> cool.

Kevin: Um, so that was cool. I saw them a couple times. I mean, and they’re not from Seattle, but, uh, Pearl jam, I saw they opened, uh, that was right before 10 or maybe right after 10 came out. So they were big enough that they were their own draw, but not really yeah. Where they are now.

What was it that got you over the line joining ship30for30?

Tim: Yeah. Facts. Yeah. My, favorite crossover of my life of Pearl jam is like they did a, a hunters and collectors cover, um, throw your arms around me. It’s called. And that’s like a pretty classic Australian cannon rock and roll song. Oh, okay. So it’s, it’s Eddie better though. So it’s, it’s not a full Pearl jam production, but, um, to kind of segue to the kinda the topic of, um, particularly interested right now is kind of, you’re writing about music and, uh, aviation, and you kind of took part ship 30 for 30, um, program experience, whatever. Um, can you talk a little bit about what it was that got you from maybe to yes? And as far as your participation in that program?

Kevin: Sure. So, um, with, when the pandemic started, do you want the long version or, um,

Tim: Medium, long,

Kevin: Medium, long. Um, I start, I took, my kids had to go to online school and so I started, I said I would go to school too. Um, except, you know, as sort of a solidarity move. Yeah. Um, except I took social, I took writing for social media. Um, I’d been kind of poking around with writing again. Um, and this class was really the catalyst for it. I, you know, I’d kind of put writing on a shelf for a while. Um, and it just, the floodgates opened back up.

Tim: Yeah, cool.

Kevin: I wound up, um, fall joining another cohort-based class. Um, I’d found medium the platform and we, I joined a cohort through there. Um, and the, the curriculum was okay, but the lightning in the bottle was the people that were in it with me.

Tim: Yeah, sure.

Kevin: Like even almost two years later, we all are still talking. That’s awesome. We bounce ideas off each other and run draughts by each other. Yeah.

Tim: Cool.

Kevin: Um, and so I, I was really turned on by the idea of the cohort and the community that kind of came outta that nice. Um, but I had, I didn’t quite get what I needed technically or structurally from the writing. Yep. Um, if that makes sense and what I needed, what I was looking for was I’m always looking to be more economical with my writing. Yep. Um, you know, if I can say it in seven words, I don’t want to use 12, um,

Tim: The school and I needed.

Kevin: Yeah. Right. So I needed something. I was really looking for something like that. And I also had all of these ideas and no way to corral ’em and I wanted to really kind of find my lane and narrow it down a little bit. Yeah. Um, and I had seen, uh, Cole’s writing on medium here and there and it had caught my eye and I had followed him. Um, I really didn’t know a whole lot about, uh, Dickie Bush yet. And one of the women that were in my cohort, uh, the original one, um, started posting a Tom essay.

Tim: Yep.

Kevin: And I was like, Hey, what, what is this? And she was like it. Um, and she was like, it’s great. And BA basically gave me the whole rundown, you know, you pick, you pick one core idea and distill it down. And, um, and so that was it. I was like, oh, this is exactly what I’m looking for. And, um, you know, I didn’t know what social proof was, but the idea, you know, here she was, and I trusted her and she was
fantastic and she loved it. And so I was cool. That was it.

What was the technique, tip, framework, hack, or whatever that helped you the most?

Tim: Yeah. That’s awesome. So you, um, you know, you were looking through some structural things and I, I found that there was like quite a lot of stuff that, that, that was available that like, in terms of like, um, you know, the various sessions that they ran for participants and stuff like that. And I’m wondering if you think about all that stuff, the idea generator, the frameworks, uh, headline stuff, like, is there a, like a, a technique or a framework or a tip or something that really, you kind of really grabbed onto that you felt like was a, a big change or unlocked something in your ability to get these ideas down?

Kevin: Yeah. So I’ll give you two. And I use them in combination every day. Sweet. Um, even when I don’t publish. Um, and that is the prep, the page.

Tim: Okay.

Kevin: Where you sort of outline everything first. Yep. And the 1 31 formats.

Tim: Yeah. Everybody loves the 1 31.

Kevin: Everybody loves the 1 31. Um, and the idea, and frankly, it just made it easier, um, having to distill everything down and having those guardrails, you know, word count guardrails. Yeah. Um, and having to do something every day, um, helped, but also having that, that structure and that, you know, Hey, you have to do this, you have to take action every day. Um, but here’s this thing that’s really gonna help you do it. And I do, I use it every day without fail.

Tim: Ma makes it more sustainable if you, if you kind of use those two things together.

Kevin: Yep. And I found even, even when I’m just outlining something or just kind of, you know, writing notes down for later, I started structuring it almost similarly. Um, I noticed a lot of my work emails

Tim: <laugh> improve.

Kevin: I’m sort of right. Like that. Cool. Um, yeah.

Tim: And do you have like a prep to page like a ritual or like, do you have a, like, have you implemented that in a way that is like kind of specific to you? If it can, you can share a little bit about how you, how I get your page set up?

Kevin: Sure. So, um, mine is decidedly, low tech. Uh, I work for an airline and I have a teletype printer right next to my desk. They still have those, we still use ’em. Um, and what I would do is I would take as it prints and we don’t obviously need the message anymore. I take those and I tear them into like, sort of like small all sections, like not quite eight and a half by 11, but maybe like four by five. And I write 1, 1, 2, 3, 1, and I handwrite ’em all out. Oh, nice. And well, and you know, more sort of scribble slash shorthand, write ’em out. And then I go in,

Tim: If another person looking at it would be like, this is what, yeah, not cool. Yeah. I also have my own like kind of freehand thing that is impenetrable to me within three days. Like if I don’t like figuring out what to do with it, it with of the day, it’s kinda like, well, something was there. Absolutely. <laugh>.

Kevin: Yes, exactly.

If you were to start from the beginning again knowing what you know now, what would you do differently?

Tim: Cool. So one and the page is the things that you’ve gotten the most out of, I wonder if you were to back in time with the experience that you have from doing it now, um, sustaining it, um, and start again. What would you do differently if anything?

Kevin: So this is my, this current cohort is my third one mm-hmm <affirmative>. And if, and I would say, if I could go back to day one, I would worry less about trying to keep up. Okay. Um, and even, you know, you see Dicky and Cole talk about it, know we’re fire hose, you with a lot of stuff, go back and look. Um, I would really just focus. I mean, all of that stuff is there for you to go check out like all the videos you can replay later, you can read the chat text, they have it all there. So it’s, you know, you can go in when you need to. And I would worry less about that and really focus on finding even just an hour a day. And that hour can move. Of course, cuz life is messy, but block that one hour a day and right. Yeah. That’s number one at, you know, keeping up with the community or reading other essays is, is, uh, second you, um, and then the other thing I would really focus on making some connections. Like I really was kind of an introvert and they had those matches the first time and my first one didn’t work. Yep. Um, not because of anything bad, the guy just wound up dropping out. Yep. Um, and that was okay. Um,

Tim: Same actually. Yeah.

Kevin: Yeah. And so, um, would say, so I would say focus on the writing, uh, make at least one really deep connection. If not, you know, as many as you want, um, don’t collect them, you know, it’s not a contest, but you know, go deep or not wider.

Tim: They’re not Pokemon.

Kevin: Yeah. Right. <laugh> exactly. Um, and, and worry less out the sort of keeping up, especially now that they’ve kind of gamified it with badges and stuff. Yeah. And I know, you know, that I understand the psychology behind it and I know it’s mainly to keep people motivated and rolling and whatever. Um, if you don’t have all 15, it’s fine. I think the main, the main value add in this course compared to any of the other ones I’ve ever taken is that, and the other ones, the lessons were sort of theoretical. Like this is what you should be doing for 30. You have to actually take action to make it

Tim: Work. It’s a little more practical.

Kevin: This course doesn’t work if you don’t write. Yeah. So if you’re not writing every day and maybe seeing data points or even just building your writing muscle. Yeah. It won’t do you any good. So really that’s, you know, sort of your Northstar finds that one or right, right. And go

What reasons would you tell someone not to do ship30?

Tim: From there, connect where you can and go from there. Yeah. So, you kinda said about if you, um, about like other courses and being more theoretical, I wonder I was an awkward segue, but I, I wonder if, if somebody, if you were to like have a conversation, is there anything that you would say, some, somebody comes up to you and say something you would, that would make you say, ah, this probably isn’t for you right now. Like what reasons would you say a person shouldn’t take it.

Kevin: So one of the things I ran into quite a bit while I was looking around for something yep. You know, there are a lot of Facebook groups or, you know, online chat or even on Twitter. Yeah. I felt like I kept running into a lot of people that were sort of in love with the idea of writing. Sure. More than actually writing. Yep. You know, they were in groups all day. Uh, I would see them commenting on others’ work all day long, you know, for weeks at a time I never saw any of their own stuff.

Tim: Yep.

Kevin: Uh, so I guess all of that, it’s a long way around to say if you’re not ready to actually start writing. Yep. And actually, just put pen to paper or, you know, fingers to keyboard this isn’t for you. Okay. You’ll get overwhelmed. You know, your old habits of just living in the comment section. Um, and you’ll wipe out fast.

Tim: Yeah. Nice.

Kevin: Um, that’s if you’re not ready, just hang out and wait for the next cohort when maybe you are. And the other one, uh, the other thing I would say is if you, for whatever reason, uh, can’t find an hour to block in your day, whether it’s early morning, late night lunch break, um, then just hang on and wait. Yeah. You’ll just get overwhelmed and you’ll get frustrated and yeah. You know, you’ll chase a deadline and, and

Tim: Yeah. Yeah. And

Tim: To like the double, double tab to like dig into that a little bit, part of the reason is I, and I think, and you can tell me if you’d agree, is that so much of the effects of this are cumulative is, is like, if you just do it once on the, a little bit at the beginning and then two weeks later, another thing, it doesn’t, it won’t, you won’t feel the same kind of say snowball effect. Um, if you a hundred. Yeah. It really is about taking the time to do it every day because, the effect of doing it for a lot of days in a row is way more than it would be of doing it once every now and again, kinda thing.

Kevin: Right. Not, not just for the data points that they talk about, but also the momentum like you in your own mind, you know, you get that momentum going, you know, you start more ideas, start springing organically from that, what you’re writing. Um, I find even when I take a day or two off, like, you know, even just in between cohorts, like you take a week off, it’s hard to jump back in. Yeah.

Tim: Facts. Um, so it’s easier to just keep the ball rolling.

Kevin: It is. Yeah.

What are some unexpected benefits you’ve seen from your participation in the program?

Tim: Yeah. Have you seen any unexpected benefits from the participation? You talked about the writing and the momentum and stuff. What else has shown up in your life for doing this?

Kevin: Um, the, I talked about wishing I had pushed, you know, I went out and met some people more. Um, so that was a huge thing to that. I wasn’t really expecting, like, I’d, I’d been in a cohort like I said, I’d been in a couple and it had all been asynchronous, you know, in slack channels or online. And it was really, um, beneficial. Like I really got a lot of value out of it. They’re great people, you know, I’d like to think they’re friends, we’ve supported each other’s work this class or this cohort, uh, took that further and it wasn’t just networking. Um, you know, one of them, one of the people I met in the first cohort, we wound up doing a zoom call and, um, uh, the Phoenix pan maybe seen her work. Um, super nice. We couldn’t be more opposite. Like she’s a Ph.D. in math, I’m writing about music.

Kevin: Um, but she made me completely rethink the way I was writing, not just for music, but aviation as well, because it’s really easy to sort of go inside the park and just write the way you’d, you know, wanna write. And her both, you know, being a math teacher and an academic really sort of forced me to rethink the way I was writing. So I could communicate a simple idea to a wider audience. Um, that was a huge value add. I would’ve never seen them coming plus she’s just awesome and great. Um, another person I met, um, wound up supporting my SubT stack. So that was, I mean, obviously from a strictly financial point, that’s a value add. It’s also one of the nicest guys I’ve run into online. So, um, and a third would send me all of these, you know, in our discussions, he would sort of forcing me in these directions I hadn’t thought about, um, and kind of pushed me up against the corners of my comfort zone a little bit in a great way. Yeah. Um, which, you know, and there, and you can sort of multiply that across, you know, all the, you know, don’t, those are the top three, for sure. Yeah. Um, you know, connection-wise. Um, but I, you know, dozens of connections like we’re talking about right now. I mean, this wouldn’t have happened if we hadn’t been in the cohort and we’re having, I

Tim: Was there. Yeah. You know, mm-hmm <affirmative>

Kevin: Um, and then, so obviously making connections was huge on the writing side. Uh, I wasn’t, we talked about data, and data points in the course. I wasn’t sure, you know, people like to write about music, um, and read about it. I didn’t know if anyone wanted, wanna read about aviation. And so I kind of, I, I had kind of resigned myself to writing about it anyway, just for my own self. And I was already posting for free and aviation, um, related forums. And I didn’t really have anything to lose. I was very surprised how interested people were in sort of real aviation, not just the sort of everything is terrible headlines that you see.

Tim: No, no, no. I’ll be honest. I follow I followed you for your aviation content. Like before I knew anything about the music side, just cuz like I was like, oh, he’s writing about like strip and the impact of strikes on the aviation, in the industry from an insider’s perspective. That was like, just like, you know, the, what I like about doing this sort of thing is that you get these windows of experience that you just would have no access to if it wasn’t for other people sharing it. And I found that really sure.

Kevin: Right. Yeah. And, and that was, that was sort of a revelation. Like I, would’ve never, there are all kinds of stories, storylines like that happening all the time that aren’t getting talked about or maybe just talked about at a local level. And I would’ve never thought that there was an appetite for that. So that was a huge, um, you know, silver line for me. It was really, yeah.

Plug yourself!

Tim: So I wonder if you could kind of, uh, bring it home by shouting out something that you’re working on that you want people to, to check out, give yourself a little plug. Kevin

Kevin: <laugh>. So, uh, right now what I’m focused on, um, is I’m writing about music obviously, and I have a SubT stack, uh, it’s called on repeat and I three times a week, I send out one song and um, with a little something attached, maybe it’s liner notes or an interview quote or something. Uh, if PE yeah. If people want to take the song and run, that’s great. If they wanna go a little deeper, uh, that’s even better if they want to talk about it or swap some stories in the comment section, that’s the best. And then, uh, usually about once a week I send that’s Monday, Wednesday, Friday, and then usually once a week, a longer essay or something. And of course playlists cuz you know, music

Tim: Because music gets right <laugh>

Kevin: And uh, so that’s on SubT stack and that’s at the Kevin Alexander dot SubT stack. Uh, and then otherwise still writing on medium and just kind of plugging away. And the other thing, the last thing I’m doing and you can kind of find these on type share or SubT stack. I’ve been kind of syndicating ’em crossed, which is another thing I realize we could do, um, is I’m listening to a hundred records reviewing a hundred new to me records this year. Awesome. And writing about ’em. So I’m at, at like 20 right now.

Tim: Good on you. That sounds like a pretty cool challenge.

Kevin: It’s been fun. It’s taken me down some really weird roads, but it’s been really fun and uh, really kind of forced me to listen to music in a new way again. Yeah,

Tim: Sure. So, well, thanks for sharing that out. I’m interested in checking out a bunch of those and I hope people watching this will be too. Uh, I really want to thank you for sharing all this stuff, Kevin, it was nice to meet you and hear a bit of your story.

You too. And thanks for having me. I appreciate it. This has been fun. Cool.

Tim: Cool. I’m gonna hit stop recording now.

If this interview helps you decide to jump aboard a Ship 30 for 30 cohort please consider signing up with this link as it helps me cover the (admittedly small) cost of putting these together.

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