ADHD Jesse Interview, Live in Boise @ Kit Studies during Craft + Commerce 2025 newsletter conference.

[00:00:00]

Chenell: All right. So we're here at Kit Studios in Boise, in Idaho. We're here with a DHD, Jesse, as I called him, and you are well known on social, under that moniker.

Mm-hmm. So, uh, we're excited to kind of chat through how you grew your newsletter. Uh, I already wrote a deep dive on how you grew it, so we, maybe we can like fill in the blanks post. Uh, I think it was like mid 2023, so it's been a minute. Yeah, yeah, yeah. It was two years. Yeah.

Dylan: So a little bit has changed

Jesse: a little bit.

Yeah. A little bit of changes in the last couple years for sure.

Chenell: Yeah.

Jesse: Yeah. Thanks for having me. I'm really excited. I'm a fan of both you and follow all the stuff you're doing and it was really wild reading the, the deep dive into myself and like feeling like I didn't know that I had like a private investigator, like looking into all my stuff.

Uh, I think the most interesting thing about it was. Learning from my own stuff. Like you, you know, unpacking things that I had done and me being able to learn from that was like such a unique and interesting experience of like just seeing like, [00:01:00] oh, that's something I did that was good and I had no idea at the time.

'cause I feel like I. So many creative, we're just winging it. We're just trying, doing so many stuff. We're we're, and yeah, we're doing so many things. It's hard to realize like when a change like affects something like, I remember, I don't remember all the specifics, but I remember you pointing out something that I changed on Instagram and how that had a certain effect and it was like, oh yeah, I completely forgot that I did that.

I, and I definitely never did those. The thing you're supposed to do of like. Hey, let's make a change and see what happens. No, I didn't do that at all. I had no idea. And so, yeah, it was, uh, super. Super interesting, uh, kind of getting to explore my own history from like a unique angle.

Chenell: I always thought it was funny when you said you were reading the, the teasers on social and you're like, oh no, I think this might be me.

Yep.

Jesse: Yeah. I remember I saw one of your teasers that you posted, and I was like, that sounds like it's me. Uh oh.

Chenell: So then the next day the deep dive dropped and Yeah. Yeah, yeah, yeah. Yeah. That's so funny.

Jesse: Yeah, that [00:02:00] was great. Rest. And I knew that you read my newsletter, so I was like, I had. A suspicion that I was like, I think I have, I think I have enough like.

Followers or whatever that I'm kind of in that range that you might look at.

Dylan & Jesse: Yeah. And

Jesse: so I was like kind of a little bit wondering and then I saw it and I was like, oh, that's, I think that's me. That's

Chenell: awesome. So before we get too far into it, do you wanna give people like a little bit of backstory of how you started the newsletter?

Jesse: Yeah, yeah. So, um, what's it called and everything too. Yeah, yeah. Great, great. Uh, so my newsletter is called Extra Focus, um, and I got the extra focus.com, which is, was very exciting. Before it was bought, it was one of those like parked domains by like GoDaddy or something like that. I think they listed it for like $3,000.

And so instead of getting that, I bought extra focus dot everything else, like.net.org, do, and then all the wor I have, I dunno, probably like 40 different extra focus versions. But then I finally at one point was like, I'm gonna, you know, did a little bit of back and forth and made an offer and then got the.com and [00:03:00] oh my gosh.

I would've paid twice as much as they wanted. It's just so, such a relief that kind of, uh, falls off the shoulders. Yeah. Um, once I basically, I imagine like, what would I do if I went here one day and somebody bought it and there was something else here? Yep. I was like, that would've ruined my day. It would've been so awful.

Mm-hmm. So I kind of, like someone said, I basically like price anchored myself. I was like, if, if I went here and somebody owned it, I would pay 6,000 to buy it then. Right. And so I was like, all right, I gotta, I just gotta just do this. Nice. So anyway, yeah. So that's, that's my newsletter, ex Extra Focus. It started back, now I'm like, you know the year, right.

You know, I think it was 2021. Because it was like post the pandemic stuff and I joined, uh, ship 30 for 30. That's where

Dylan: we connected. Yeah.

Chenell: March of 2021. Yeah,

Jesse: yeah, yeah. Yeah. So it was like, I think it was the second ever ship 30 for 30, which was like the first like official one. Yeah. 'cause before that it was just like run on Twitter.

Yeah. And for anyone that doesn't know, ship 30 for 30. The whole premise is basically you write 30 [00:04:00] atomic essays, which is like a, like a 500 ish word essay. Then you ship it, you release it that day. So for 30 days in a row, you're writing every single night and then sending it back. Then Twitter was the main place.

I'm not sure, I'm not sure what they're doing these days. Um, with that. I don't think they run

Chenell: Ship 30 anymore. No. What's that course?

Jesse: I think I got an email recently that they're gonna do a new cohort. But anyway, so that's kinda, I signed up for that. I have no idea why I signed up for it. I previously had no like ambitions to be a writer or a creator.

I mean, I was like a creative, 'cause I do design and stuff like that. Yeah. But no, like I, oh, maybe a content creator. Oh, I'm gonna write a book one day. None of that. None of that ambition really. But for some reason I saw the ship 30 for 30. I was like, that sounds like a fun, uh, thing. I think I'll do that.

Originally I kind of like outlined what topics am I gonna talk about and I put down design. Um, and I put down tech because I've done like talks at tech conferences and stuff like that. So I kind of [00:05:00] thought that might be my thing. And then I also had been diagnosed with A-D-H-D-A few years earlier.

Mm-hmm. And I learned a lot about that to just understand my brain better.

Dylan & Jesse: Yeah.

Jesse: So I thought, oh, maybe I'll do a couple of those on ship 30 for 30 as well. And I did like one or two, and then immediately it was just like. This is, people don't know this stuff. And immediately, like that's, that's the content that people are connecting with and replying to.

And I think especially Ship 30 for 30 is gonna attract a lot of like entrepreneur minded people. And there's like studies showing that entrepreneurs of like way higher percentage likelihood of having a DHD, right? And so there was a lot of people within the cohort itself that were immediately kind of interested in the content that I was writing about.

So that that happened. And then I think everyone just within Ship 30, were talking about things you should do. And so someone was saying like, oh, you should, now's a great time to jump on TikTok because there's a [00:06:00] lot of people viewing it, but there's not enough educational content. And so there's a lot of like people in their thirties and forties that are on TikTok and there's not enough content for them.

Yeah. Um, and then somebody else saying like, you should have a newsletter, like get a newsletter right away. And, uh, so like a week in, I think back then it was, so I immediately signed up for Substack, which was free. Back then it was free up to a thousand subscribers.

Dylan & Jesse: Okay. And

Jesse: so that when I signed up, I did Substack 'cause it was free and I just started, basically I was just sharing the atomic essays I was writing.

Yeah. So I'd do like a weekly newsletter. It was like, here's the four things that I wrote about A DHD this week.

Dylan: Yep.

Jesse: Then it's kind of snowballed a lot since then. The

Dylan: snowball is no longer a ball, it's more avalanche and yeah. That's awesome. Do you wanna share

Chenell: some numbers from now to give people context, like how, how many subscribers you have and that kind of thing?

Yeah. So the

Jesse: newsletter has grown a lot. Um, it's up to [00:07:00] 70,000, uh, subscribers now.

Dylan & Jesse: Nice.

Jesse: Which is pretty, yeah, it's pretty, pretty wild. Um. So that's the, that's a newsletter. And then I kind of, you know, I've done a lot of the other stuff. So I have like, I dunno, roughly like across like Twitter and Instagram and Blue Sky and like Threads.

I probably have like four to 500,000 followers across all those. And then I have a YouTube channel with like 85,000 sub uh, subscribers or. Subscribers. That's what they call em, right? Yeah, yeah. It's, it's so like different platforms. Sometimes subscriber means like a financial, like substack sub. Anyway, it's like a whole thing.

But yeah, so it's kind of wild how all this has happened. Especially because I've been working full-time, um, during all this, like I said, I was in tech, I've been a front end, uh, designer and developer, and I was, I had a full-time job all of this time as well as like, I have a family with three kids, right?

And so I, I was really just like trying, kind of making this thing happen on the [00:08:00] side. Um, as well as writing a book. I didn't mention that too. I, which, that actually came directly outta ship 30, uh, because I. I did the first ship, 30 for 30, and I was like, this is amazing. I want to keep writing. Mm-hmm. And then I actually, I did like two more cohorts.

Uh, I didn't do all 30 days, the other two. Yeah. But I wrote a lot. And then at some point I was looking at all the essays I had done and I was like, this is like, this was like 25, 30,000 words right here. This is, this is basically a book. Mm-hmm. I should write a book. I can just, this will be really quick and easy.

Yeah. Uh, it's spoiler a lot. It is. Spoiler alert. It is not easy writing a book is, I, I, I think I used none of those words, but that was like my original foundation. Got it. And then you find, find out that writing a book is so much harder than just putting much of essays in a row. Uh, 'cause there's so much like context building and like a storyline.

Like not necessarily a storyline, but some sort of. Path through line. Yeah. Through line for readers to follow. Yeah. For things to make sense and like, uh, anyway, this [00:09:00] isn't a book podcast, but it's like a whole other thing. And, but that really, I think, kind of helped cement me, like within the A DHD community having like now I'm an author and, um, yeah.

So that's been, it's been kind of wild doing all of this. Somehow on the side, uh, while having to do the main, the full-time job and, uh, raise family in family. Mm-hmm. Yeah,

Dylan: I was gonna make the joke, like, oh, you have a full-time job and you're doing all this, so you must be single. Right, right. Yeah,

Jesse: yeah, yeah.

Or like, like single and independently wealthy Yes. Or something like that to like inheritance.

Dylan & Jesse: Yeah. Yes.

Jesse: I, I hire someone to do all my stuff, right? Mm-hmm. And I'm single and have no responsibilities. That's right. Yeah. No, no, I, that is not the case. I mean, I, I am married and my wife's amazing and does. A lot of stuff for the family for sure.

And that's, that is something I think a lot of, uh. People forget to mention. Mm-hmm. Mm-hmm. Especially the, like, the, you know, the big, the, the white male that talks about how they're like [00:10:00] grinding to get the stuff done. It's like, yeah. Well, who's working behind the scenes? Like for me, it's my wife. She's working behind the scenes Yeah.

And doing a lot to, uh, take care of her family and get a lot of those stuff done. Especially you to do this. Yeah. Yeah. Really, and being amazing and supportive of like, doing this stuff and especially having a DHD. Um, she doesn't have a DH adhd. Mm-hmm. And so that helps a lot. Like schedules and things like that is so hard with kids.

Because it's just, it's, I do not know if, if, if I didn't have my wife, I would have to hire somebody to manage just my kids' schedules because it's, it's so, they're doing sports and music and it, it's like, it's wild. And how many kids do you have? Three

Dylan: kids. I have three kids. Three

Jesse: kids? Yeah. So eight, 12, and 14.

Oh

Dylan: yeah. That's like busy sports and Yeah. It's like they're all just getting into

Jesse: that now and yeah. It's, it's intense. Wow. Yeah. We're, we're just coming out of like right at the end of the year too. So like. Everything just happened. Oh yeah. Yeah. It's like there's the end of the school year things happening [00:11:00] and like the concerts are happening.

Right. And then like the ba, the final baseball games and like all, everything is just like wild uh, right now.

Dylan: Well, thank you to your wife for allowing you to be here even. Yeah. Yes. Right. Yeah. Absolute. Absolutely. An hour flight away from home or so roughly that you drove. Well, 10 hour drive drove. I drove.

Oh, you drove? I drove, yeah. Wow. That's

Jesse: actually my favorite part. That's the reason I came to Craft and Commerce. In the first place three years ago. Wow. This is my third time because I love a solo road trip. Like, just like, yeah. Cruising in my car by myself, uh, is amazing. So it's about a 10 hour drive for me, uh, from the Seattle area.

Dylan: Okay.

Jesse: And the best is actually going back because the conference ends and then I get to just like, sit by myself on the car driving home and really kind of decompress and like. Think about like, okay, how am I gonna put these into practice? Yeah. And also it gives me that gap before I'm home and suddenly have all the dad responsibilities.

Right. Oh, I love that. Yeah. And the kids are gonna want to do, you know, all [00:12:00] that then. And then you lose all that like context that you're kind of holding in your brain this week, being at the conference. So that drive home is gonna be great.

Dylan: Well, let's, let's quickly touch on like what are some big takeaways from, I know this isn't a con, a podcast above the conference, but it's all very relatable to Yeah.

Yeah. Newsletters and growth and. Authenticity is a big theme. Yeah. Yeah. So like how, what, what are some of the takeaways that you've had from this conference so far

Chenell: and before just to level set. So you had a day job and you no longer have a day job. Yes. So I feel like all of these ideas are coming in through a new lens now.

'cause you probably have a little bit more time and flexibility to like implement some of 'em.

Jesse: Yeah, absolutely. So that's been, I, I feel, um, again, with speaking about craft and commerce for the last couple years, uh, it's been a little bit weird 'cause I'll, I'll talk with people. And they're like, oh, what are you doing?

And I was like, well, I'm, I like, don't really have a business. I'm building an audience, but I don't have the time Yeah. To figure out how to actually make a business out of it. So I've been just sort of, kind of doing it backwards in that [00:13:00] way. Um, but yeah, so as you mentioned, I, uh, a couple months ago I got laid off for my job and which was in the tech field.

So it is like the, it's the golden handcuffs problem where. Like, you want to leave because like, I want to want to dive into this creator thing and I've got a lot of, um, you know, I don't know the term I said audience, I usually don't use that, but just like I have a lot of people I know that I can help.

Dylan & Jesse: Mm-hmm.

Jesse: And I want to be able to put more time into doing that. Mm-hmm. And I haven't been able to, 'cause I have full-time job and the family and so when I got laid off, I immediately was like, obviously I'm like, well, I gotta replace that income. I gotta find another job right away. But. I, I basically kind of like wrestled with a little bit and then decided like, no, no, no.

Like if I, if I jump into another job right now, then I'm never gonna do this. Mm. It's just like, it's never gonna happen. Yep. And then that mixed with the fact that I. I just outta nowhere lost my income and it was completely outta my [00:14:00] control. Right. There was zero that I could do. Yep. It wasn't even like, I didn't get fired, so it wasn't like I didn't even do anything that messed up at work.

Yeah. It was just somebody else like, you know, did whatever. And then my, I took the result of it were impacted. Yeah. I was impacted. Yeah. And suddenly all that like revenue went away. Mm. And I had no control over it. Yeah. And so that's another part of it too, of. It'll take a while to figure that's what I'm doing right now, like navigate and kind of figure this out.

But then I have the control. Yeah. And um, so I'm looking forward to, to that and kind of figuring that out, which is a lot of what kinda take away from this conference of how am I going to do that and turn, turning, turning education into a business that makes sense and can help people and support me and all of that.

So. I think there was a, the question that, I forgot what it was. That's okay. So I've been talking for a while.

Dylan: That is a classic, uh, I can relate a hundred percent to that because I dunno how many podcasts I've been on where I'm be like, I've been rambling and I don't even know what the question I was answering.

Yeah. What happens when [00:15:00] three people with a d ADHD come into a room and do podcasts? Right. Um, so I think what I was asking you is kinda like what is your, what is your big takeaway or opportunity maybe that you see based on something you've learned here at the conference that you. Are excited to implement into your business if your, uh, newsletter business or whatever it might be.

Jesse: Yeah. So there's a, there's a couple of things. Um, one, I'd say, as you kind of mentioned, there's a lot of focus on the authenticity and like being with how AI is kind of, you know, over changing everything. Yeah. Being a part of everything, like leaning into what makes you human. And I think that's something if just to be like transparent, I feel like that's something I've kind of lost with my newsletter maybe in the last year.

I've felt like it's been harder to do that. Um, and part of that is when that number gets high enough that so many, you start to overthink, should I be more streamlined? And like every newsletter is exactly a strategy with three takeaways. And like, it's really hard to not do that. [00:16:00] But now it's like AI can spit that out like that.

Yeah. And so that's not the value that I'm gonna be adding.

Dylan & Jesse: Yeah.

Jesse: And I really need to, so that's something I'm hoping to kind of recapture is like getting back to. What I was doing kind of early, especially I think my second year doing the newsletter was when it really started to grow. Mm-hmm. So partly I'm like, I just need to go back and look at that and remember kind of what I was doing and be more true to myself and talk about things I'm learning and things I'm excited about and stuff like that.

Because I think it, it's so easy to get in your head and be like, it's gotta be an exact. Formula for every week. Yeah. And that's not, I think that's not really what people want.

Dylan: Not anymore, I don't think. Yeah. I think there was a place and a time for that. Mm-hmm. Yeah. And now I think it's gonna come back to a lot more of like, I know Jesse and I know.

Like, I like his vibe. I've stayed, I've been a reader of his for a while. I kinda wanna hear like about him a bit more about what he's doing in his life, you know, dealing with the same things I'm struggling with and how he navigates them. Right, right. As opposed to like, here are three ways that you can overcome this problem with a D.

You know what I mean? It's like, [00:17:00] yeah, I know nobody, like we're overloaded with information and advice. And I think when you weave story and personal, I think you wrote, if I remember correctly, when I was subscribed to your newsletter. Which I can't remember honestly if I still am or not, but, um, I remember you talking more about your own personal experiences with it Yeah.

And how you came to learn about it. And you just like kinda shared a bit of those stories, but then you'd also have a bit of a takeaway at the end and Right. And a lesson to learn. So I appreciated that as somebody who was kind of newly diagnosed with it. So yeah, I think there's a place for that. And that's probably why a lot of people si signed up and stayed signed up.

Jesse: Yeah. Yeah. I think there's that. It's, it's the whole. Um, I forget the phrase, but basically the problem of becoming more of an expert in your, you know, the curse of expertise. Oh, yeah. Yeah. And it, it, it gets, um, I've found that with myself lately where I assume that everyone knows this base level of knowledge.

Curse of knowledge. Yeah. Curse of knowledge. Yeah. And they don't, like, I find out all the time people don't know that. Yeah. And assuming that not only does that mean I didn't help them, but [00:18:00] then it almost makes them less want to come to me. Sure. Because it, it feels like, oh, he's. He doesn't even get me.

Yeah. And I feel like that's, that was sort of the strength of what I was doing early on. People felt really, really seen because they, because they felt like I got them. Yeah. Because I've been there too. I understand what it's like living with A DHD, especially undiagnosed. I was, you know, I'm not diagnosed to my.

Mid thirties. Mm-hmm. And so, and that's, that's really what I'm trying to, hopefully to recapture with my newsletter and just like that, that voice and not trying to be the expert. Yeah. Which I feel like you said if like last year or something, like a year and a half ago, it felt like things were suggesting I should move that way.

Mm-hmm. And now I'm feeling like I think I should pull, I think I went too far that way. Yeah. And then I didn't love it either. Right. Because it was like that this isn't even what I enjoy doing. So. It's almost like the newsletter becomes a chore. Mm-hmm. Yeah. And when that becomes the case, every reader feels that.

Yeah. You can feel when the newsletter, the transfer [00:19:00] of

Chenell: energy. Yeah.

Jesse: Yeah. They, you feel when they're not in it. Yeah. And so I'm hoping to really recapture what I loved about that, uh, for most of the time mm-hmm. That I was doing it. Um, it'll probably make it

Chenell: easier to write too, like Yeah,

Jesse: absolutely. Like write right now.

I feel like I've, for months, I've just like dreaded it and I don't, that's no fun. Yeah. Yeah. I don't want to do that. And no one wants to read that. Like if I dreaded writing it or like, yeah, that's, that's no good for anybody. And so I'm really hoping to just recapture like what I actually wanna write about.

Um, that is going to be, yeah, kind of authentic to that beginner, just like recapturing, um, that sort of thing is. That's my hope. So that, that's a, that's a big one. Yeah. Takeaway, uh, kind of from this conference and a lot of the stuff I'm hearing, um, a little bit more practically as I'm like trying to figure out the business side of things, um, is there's been so, like Jay Klaus will sometimes say like, he's set a bunch lately.

I feel like that he thinks [00:20:00] courses are basically going away.

Dylan & Jesse: Mm-hmm.

Jesse: I don't know. That feels a little extreme. Yep. But it is interesting to hear him say that while I'm like, Hey, I'm launching my course. You

Dylan & Jesse: and me both. Yeah, it's okay.

Jesse: Yeah, yeah, yeah. Um, but so that's something I'm really thinking about. Um, like the, I think the marriage of like a course and a membership

Dylan & Jesse: Yeah.

Jesse: And how to do that in a way that really, um, that helps people and, uh, helps people connect with other people. Because that, that was again, with like the A DHD thing. That's what I found so valuable when I got diagnosed was finding other people that had it too, and knowing that like, oh, I'm gonna be able to connect with them.

Mm-hmm. Yeah. Because now we have this like shared understanding. Yeah. Mm-hmm. And I, that's the sort of thing that, that I hope to, with some sort of membership. That's a big part of what I want to bring to people is a way to connect with other people. Again, sort of like with Jay Klaus being in the lab, being able to like connect with people that are sort of in.

A similar space that you're in is really [00:21:00] great. Yeah. And so like a community like that could be super valuable where you kinda have this baseline understanding, like you can complain, complain about things that maybe you wouldn't complain about with your neurotypical friends, or maybe your neurotypical spouse.

Your spouse. Yeah. Yeah, yeah. 'cause there's some things where if you don't have a DH, ADHD. This isn't gonna make sense. This is just gonna make me look like a lazy jerk or something like that. Mm. Yeah. But people with a DHD get the struggle. Mm-hmm. Yep. And so that's really what I'm hoping to kind of, I, I feel like I'm hearing in multiple places that a model that seems to be working for people right now, I.

Is doing a course and then moving into a membership from that course. I was gonna say yeah, a hundred

Chenell: percent. I keep hearing that too.

Jesse: Yeah. I think, uh, Becky Pearson Davidson, I was just talking with her 'cause she was in the lab and we just did like the mastermind thing and she was talking a lot about that.

Chenell: Yeah.

Jesse: And so that's, that's definitely a way that I'm leaning and I feel like that's something that I've heard a lot from my, like from c the community and readers and stuff, that they want to be able to connect with more people. Like the, the silly thing [00:22:00] is that I've, I've done some courses before, like, uh, live cohort courses.

Okay. Or, you know, like virtual live cohort courses and we'll, like, maybe I'll throw together like a Slack channel or something for the, like three weeks we do it, and then at the end of it, every time they're like, oh, I wish we could keep doing this. And, um, you're like, I'm the idiot. They're like, no, we can't, can't see you.

Bye. They're like begging you to Yeah. They're take my

Dylan: money for a community, basically. Yeah.

Jesse: And so hopefully at the end of, uh, so I did launch, I did like a launch window for a course. Mm-hmm. And we're going through that right now. And hopefully at the end of this one, people start to say that again. And I can say, well actually that's a great idea.

Yeah, let's do it. Um, I still, is this a

Chenell: cohort course?

Jesse: It's sort of a hybrid, is what I'm doing. Okay. 'cause I didn't, I sold the course and I didn't have anything done yet. I had like an outline and I had kind of an idea of what the content would be, but I, I didn't want to teach all of it live like I wanted to get to [00:23:00] having a recorded asset.

Okay. Um, and having like, maybe some, maybe it'll be an evergreen, probably not, but possibly. And so I wanted to have that done so that I didn't have to. Reinvented. I, I think when I've done the course, I, like I've mentioned, I've done a few cohort courses in the past and I always feel like I have to reinvent it every time.

Yeah. Right. So I kind of wanted something that like, I'm gonna do this one and I'll record basically a module every week, and then I can kind of adapt a little bit based on what people are saying. Mm-hmm. And then at the end of it, I'll be like, cool, no matter what, Jesse, you don't need to record more. Use this for two years.

Yeah. And then maybe after two years, rerecord it up with learning and stuff like that. Yep. That was sort of like, it was very, this was sort of like a, I, I called it like a founding cohort because it was really like, this is to set the foundation. I specifically priced it cheaper than I planned to so that I would get more people in there to be able to get testimonials.

Yep. Smart. And so I was trying to like really do a bunch of stuff that's going [00:24:00] to, um, set me in a good place for the future so that I can do it. Easier in the future so that I can focus on some other things, like probably the community things. Yeah. Mm-hmm. Um, yeah,

Chenell: I think that community sounds like an awesome spot.

Yeah. Like it would be so fun to have a place to go and it's like. Hey, did anyone else just get yelled at for this whatever, by, or, I'm so embarrassed I did this thing. Yeah,

Jesse: yeah, because there's so many things. Yeah. With A DHD, like this isn't an A DH ADHD podcast, but there's so many things with A DHD where it's just, it's so easy to feel the, just like the immense shame.

Yeah. Yeah. Because you have these intentions and your actions so often don't meet what your intention is.

Dylan & Jesse: Yeah.

Jesse: And. People that aren't a DHD, it's so hard for 'em to understand that. So it feels like your intentions are bad.

Dylan & Jesse: Right? Right.

Jesse: And because of that, there's all this like shame that gets involved and misunderstanding.

Yeah. And all these things and yeah, you feel like most people aren't gonna understand, which is how I felt, you know, 35 years of my life. Mm-hmm. Like no one else understands. No one else gets it. And so when [00:25:00] you have somebody that you can talk to that gets it, you can talk about the really like. Things that are embarrassing to tell someone that is neurotypical.

Mm-hmm. And, and, and get understanding instead of like, uh, blame or whatever it would be.

Chenell: So I feel like you just wrote the sales page right there. There we go. I gotta, I gotta, I'll download

Jesse: this right afterwards. Link in the bio for all the

Chenell: No, that's right. Link in the description for all of the course and community stuff.

Yeah. That's

Dylan: so funny. Love it. So you have a, uh, paid aspect of your newsletter Right on Substack.

Jesse: Yeah. Yeah. Okay. Uh, so I'll say, let's talk about that. Yeah. So the story with that, um, well, I've been like bouncing back and forth between Substack and Kit since I started. 'cause like I mentioned, when I very first signed up, I did it on Substack because it was free.

Mm-hmm. I can't even remember the specifics, but I remember I hit a thousand and I can't remember what it was, but that was like a, oh, now you're gonna have to pay something. And, which is not the case anymore. Yeah. But something at that point was a catalyst at [00:26:00] specifically a thousand. So I jumped over to ConvertKit at that point.

Oh,

Dylan & Jesse: okay. Okay. I,

Jesse: I don't, I, yeah. I can't recall exactly what it was. Um, but, so I moved over to ConvertKit and then I was there for a while and then I started, uh, the recommendations started happening. Oh yeah. Right on substack. And, you know, back then they were the only ones doing it. I was like feeling really like jealous of like people that were getting that free growth.

Yeah. And so I jumped back to sub, uh, Substack, which was a great move because I've probably gotten like eight, 9,000 subscribers through recommendations. Okay. On substack. But that has its own problems. Uh, but anyway, so when I jumped back, when I was like, I, I want the recommendations, I want the other stuff I'm gonna set like, yeah, I'm going all in on Substack.

I, they had something called pledges, and so paid newsletters were, was their big thing. But I was like, ah, that, that doesn't really feel like me. Yeah. Um, but this pledge thing, sure, I'll do that. [00:27:00] And then with the

Dylan: Patreon sort of model where you can like,

Jesse: well sort of touch your support. So pledge is, you would basically say, if you turn on a paid newsletter, I would give you this much.

Oh.

Dylan & Jesse: That sort of

Jesse: a thing. Okay.

Dylan & Jesse: Okay. And

Jesse: so it's like not quite going, but then the way it worked is people could pledge. Then you could just say, yeah, I'm gonna go paid. And all those pledges would like, would get charged. Oh wow. Okay. Yeah. Wow. And that was really weird to me. I was like, I would never want to do that.

I would never pledge. And then just like, it's like writing a check and having no idea when, when it's gonna, or if it's gonna be cashed.

Chenell: Did they get like a notification before that? I don't. I

Jesse: don't actually know. Okay. But basically I kind of like walked through what the process would be for a reader. I was like, well, this sucks.

Um. I guess I'll just turn on paid. Yeah. So that's what I did. So I turned on paid and I didn't have any plan for what to do if people became paid. I Oh, that's funny. Just turned it on and see what happened and, uh, like 150 people or something Dang. [00:28:00] Signed up to be paid like right away. Shoot. I was like, oh, well, interesting.

But it's, it's hard to grow paid subscribers. Mm-hmm. On Substack, I've found out. Um, so it seemed like, oh, well I'm gonna be making like. 500 K in just a few months here. I just keep bumping up that by a hundred every month. Uh, that's not that that easy to do, not how it works, how it works, not quite how it works, but it's kind of complicated now because I have, um, I have grown that somewhat.

So I think I have like close to 400, uh, subscribers on Substack. Paid. Paid subscribers. Yeah. Okay. Yeah. Yeah. And, but it, there's kind of this weird thing where I don't do a lot for them.

Dylan & Jesse: Mm.

Jesse: Partly because most of the time that's been a paid newsletter. Like I said, I had the full-time job and the family.

Yeah. So it was like not really doing much. It was basically like, Hey, if you wanna support the work I'm doing, yeah. You can pay $8 a month. And then you also get. Free access to the archive. And occasionally I would do like, like I'd do like an annual, um, like an [00:29:00] annual review template. Okay. And so I might do like a plan your year workshop.

And that's free for anyone that's paid. Yep. Paid members. Okay. Like a few little things like that. Yep. But not a lot. Um, and also the price point's really low. Mm-hmm. Because it's like $8 a month. And so now I'm, that's the thing I have to figure out because when I launched this membership out of the course thing.

I don't know what I'm gonna charge, but it's gonna be more than $8. Like $8 just isn't really gonna be sustainable.

Dylan: Yeah.

Jesse: But now what do I do for the people that are paid? That's something I'm trying to figure out how to, like, do I offer them a discount? Do I just like kill the paid newsletter and then launch?

That's a whole thing. I'm trying to. Navigate right now. So, uh, any advice? What would you guys do? I

Chenell: would just say be careful. 'cause if you have stuff outside of Substack, they don't like that necessarily. Right. No,

Jesse: I know. So that's been when I like launched, uh, the court. So right now I have my 70 sub 70 K subscribers and Substack and in ConvertKit.

So I'm actually doing both. Okay. [00:30:00] Because for the course launch, I needed, excuse me, I needed the power that ConvertKit gives me to, 'cause I didn't want to send. 10 emails to every single person. Right. So I like sent out an email and then if they clicked a thing or did something that showed interest and then they got additional emails.

Yeah. But most people just saw, I think three total. Okay. Emails over like two weeks. Um, and so, but now I'm trying to navigate how to do both and it's, it's a nightmare. But I also can't leave Substack 'cause I have like, like 250 people that recommend me or something like that. And so I can't. So I, I have this like crazy automation with, I think it's make.com, is that?

Yep. I saw somewhere. And so I have a thing that does that and then brings them over to ConvertKit. Okay. But it's complicated and it's, it's like, it's, it's a whole thing. What do I do guys? I do the

Chenell: same thing, but with Zapier, it's really simple. Oh, you can do it.

Jesse: I tried to do it with Zepi before, and. I'd much rather have it.

I do do most things. I don't think it's like

Chenell: kosher, but they [00:31:00] send you an email every time you get That's exactly

Jesse: what I do. Yes. What makes, so the email comes in with, and it grabs that and then it pulls it over. Yeah. So I, let's talk after so I can, because I, because I'm paying for. Zapier and make, oh shoot.

How? 'cause I saw a guide and it only showed the way to do it with make. Oh yeah. I'll show

Chenell: you how to do that.

Jesse: Yeah. So that's step one. That, that's good. Now I know that. Okay, that'll save me that. Whatever I'm paying for make.com. So

Dylan: I got one thought on the, um, 'cause you asked what you should do with the, yeah, yeah.

So could you not bundle, keep those people at the $8, $8 a month price point, but then have your upper tier be like, include. The community, like a higher tier on Substack, or do they not let you do that? They don't

Jesse: really do that. They have like, I mean they have like I, I believe they just have like monthly, annual, and then they have this like, founder, yes, enter whatever.

You enter a certain

Dylan: price that has to start at a certain price or whatever.

Jesse: Right, right. Okay. Yeah. And then the other problem is I'm even more tied in with Substack. Another pro, like as far as like my membership, that's [00:32:00] not gonna be run there at all. And the other problem is substack, like we just said, we're having to do this weird work around.

Mm-hmm. 'cause they have no API. Yeah. No way to like really. So if somebody does that and buys on there, I have to do some weird work around to be able to get them into my like circle community or whatever, wherever. Do you still

Chenell: send emails from Substack?

Jesse: So that's something I've been like thinking about a lot this week.

Yes. Okay. So currently right now. Yes. And I've thought about like, now that I moved everyone back over to ConvertKit, should I just start sending all my main newsletter through ConvertKit and keep Substack and keep pulling people from it? And then, then there's all the complications of like, well, if I do that, should I still post the same newsletter in Substack so that like the public one is there and just not actually send it?

Dylan & Jesse: Mm-hmm. Yeah. To

Jesse: anybody. But one thing I've thought about with that is people that are paid subscribers, if they want to. Cancel their thing. Now, that's not linked in the newsletter, and so it becomes like if, if I'm a [00:33:00] paid newsletter subscriber and I like, oh, I want to go cancel my subscription, where do I go?

Dylan: Can you have just like a baked in link in your footer saying cancel subscription there? I mean, it sounds really

Jesse: dumb and easy when you say it like that, so yeah, probably it, it sounds like a really complicated problem in my head, but yeah, I probably could just do something like that.

Dylan: That would just take 'em to like a cancellation page.

Jesse: Yeah. Yeah. Mm-hmm.

Dylan: The only challenge is, I don't know if it would carry the UTM parameter from their email over or what, but you could, right. You could at least take them to your main Substack page that would have them logged in and then they could like click on, I could even put

Jesse: together a landing page that says how to do it as well.

Yeah. Yeah. So. It sounds so much easier when you're talking to somebody else.

Dylan & Jesse: It really was like, I

Jesse: would probably, I'd probably put way too many hours into thinking about this on the side, but yeah. Yeah, so I think that is probably what I'm gonna ultimately end up doing. Yeah. Is start sending the main newsletter through ConvertKit or through Kit and just sort of like copy it over to Substack so that it still maintains its like Blos or whatever.

Chenell: Yeah. [00:34:00] I think that's a good move. Yeah. But the commu, I mean, the community sounds like a no brainer in my opinion. Yeah. Even if people aren't in the course necessarily. I don't know. That's tricky. So that's,

Jesse: that's the thing I'm trying to figure out. Like do I want it to be like, the course is the prerequisite.

I was gonna say,

Dylan: I think that's. If it was me, I would feel that that should be the, maybe the way to go. It depends like

Chenell: what is the course, I guess having,

Dylan: having it be the prerequisite would be the way to go. That's what you're saying. I think that's kinda like, that's your in, if you wanna get in this in the community, um.

Take the course so that you understand the fundamentals. What, right. It kind of sets the

Jesse: baseline Yeah. A little bit. Even though I'm certain that people aren't gonna go through the whole thing, and, but at least there's, yeah,

Dylan: there's the expectation at least that you have taken some of the information. Or if you, if you wanted to do the cheat route and you're like, yeah, yeah, I'll take the course and then like, complete, complete, complete.

Right. And you get in the community and people are talking about the course and you're like, oh, damn, maybe I should go back and actually help you. Right? Yeah, yeah, yeah, yeah. And they have the access then.

Jesse: I

Dylan: dunno.

Jesse: Yeah. Yeah. I like that. Um, there is the whole thing, like part of me [00:35:00] has tried to think about like, should I do, should I make the course evergreen, but at like a higher price and without a live element?

And then do like occasional launches where we'll go through the course and do like some of the live stuff. And it's like at a, then I do like kind of the launch window thing. That's where I'm, I'm trying to figure out that 'cause. I launched a course last month. Yeah. And it'd be cool if money was coming in like today.

So

Dylan: that's where

Jesse: I'm like, did you do a presale tempted to like figure out the Evergreen as well? I'm not sure.

Dylan: Yeah. Did you do a presale?

Jesse: Um, no. I did like a, I did like a launch window. I did, uh, I dunno if you know Jeff Walker, he's the whole product launch formula thing. I basically, I read, I read the book, um, a year ago and I was like, that's cool, I should do that.

And then I got distracted by things, but then with this I was like, I'm just gonna follow it. Exactly as the book says for this launch. Okay. And then see how that goes. And it went pretty well. The one thing that didn't work well for me was doing like a webinar. And so I [00:36:00] did like, like a masterclass webinar sort of thing.

And that didn't seem to move the needle at all for me. Huh? But like referring again, back to the lab, I posted about it in the lab and I got like, I don't know, like 15 replies and people were like, oh, well that's 'cause you gotta do this and you gotta do this. So those. Part of me was hoping that it would like, that it would flop.

And I think that's probably why it flopped. You know, it's like I did a, I did a good job, I think, but I didn't optimize in a lot of the ways I probably could have. Yeah. And so part of me was like hoping that I wouldn't have to do it, but I probably just need to do it better. Yeah. Next, next time around.

Yeah. Let's see

Dylan: if I could sort of half-ass this thing. Yeah. A little bit. And it'll still succeed maybe. Yeah,

Jesse: a little bit. I feel that.

Dylan: I feel that. Cool. So. Um, the other thing I think that you could, you mentioned it too, with the paid, like what do I do with these, you know, 400 paid subscribers? Yeah, yeah.

You could either like, just put that, um, the monthly amount that they're paying towards maybe the new membership, which isn't a much, it's like eight bucks. Mm-hmm. Or you could just [00:37:00] be like, um, maybe look at grandfathering them in or something to some degree. Mm-hmm. Or giving them some kind of special discount for loyalty of being with you for X amount of time or.

I dunno, but yeah, like

Chenell: depending on how much they paid, maybe you give them a discount that would get a little tricky. Could get muddy.

Jesse: Yeah. Yeah. But the thing I, I think the, like should I, I mean, I don't know. The, the thing I'm wrestling with is should I aim to kill the paid subscription through Substack and try to move those people over to, you know, whatever I'm doing for like Circle community or whatever, like a, just a Stripe membership that's no longer.

Tied to the substack thing. That's, I think that's sort of the thing I'm trying, like should I be trying to move those people or do I still sort of have both and yeah,

Dylan: my gut says like, yes, I would eliminate that. But you also don't wanna do that before, you know, the other thing is, I know that's exactly like, I'm not,

Jesse: I don't want to turn off the money.

That's like helping, you know, put groceries on the table right now. Yes. So there's that. Kind of thing to figure [00:38:00] out first. Yeah. Yeah. Because like I said, like for, it's not, it's not enough to sustain us, but it's some money that's coming in right now. Totally. While they don't have a job. Yeah. And so that's the, like, how do I figure it out without turning off a valve that brings money into my bank account?

Chenell: Yes. Yeah. I think if you set up a decent enough email sequence to those people specifically mm-hmm. And say like, Hey, here's the direction I'm moving. You can keep paying if you'd like, but I don't want you to just pay for something you're not really getting.

Dylan & Jesse: Right. Right.

Chenell: Um, and then you can offer them like however much off the course if you want.

If they wanna upgrade.

Jesse: Yeah, yeah, yeah,

Chenell: yeah. Um, but yeah, if you're not spending time there and like you're, it's just kind of like, well that was cool that happened. Like yeah, they're not really getting too much more. It might be something to migrate away from. And

Dylan: it also like, hang over your, I dunno about you.

For me, it would just like hang over my head like I got Yeah. So like, it'd be nice if they just, everybody was getting the same value in the same spot.

Jesse: Right? Totally. Because that's the, I didn't even mention this, but before, for a little while, I had a Patreon and not very many people were there. And [00:39:00] so it was like it wasn't bringing in much money.

Yeah. But I felt constant guilt about it. But I also couldn't, because I was, my time was so limited, I couldn't justify. Putting time into something that only how, you know, like 30 people we're gonna see. Right, right. I was like, I can't, I gotta just do it free. So it was never worth it to put time into something for these 30 people, but they're giving me money every month.

It was such a bad kind of dynamic. So I just like shut that off and like just said, thank you so much for supporting, I'm gonna be shutting this down. Yeah, yeah. Um, but company for my

Dylan: $8 a month subscription. Yeah.

Jesse: And so unfortunately, I mean, no fortunately. I have the problem of a lot of people are subscribed on, on Substack, so I just have to figure out how to Yeah.

Kind of navigate that cleanly Yeah. To hopefully get them moved onto something that, um, that works a little bit better. Yeah. And like you, like you said, like I have, I'm only offering like a thing to a, to one type of community, not trying to manage several different ones. Mm-hmm. With different, yeah. That's like a whole [00:40:00] mess.

Dylan: I think it would be interesting, we only have a few minutes left, but um, I'd be really curious like. How you, what channels you were using just to really like, see a lot of growth. 'cause I know you were, like, you were growing on Twitter quite a bit. Yeah. Um, and then you started posting, I think you said like your cousin's wife was on Instagram and she was blowing up.

Yeah, yeah, yeah, yeah. And then you kind of started following in those footsteps a bit too yourself.

Jesse: Yeah. So it's, it's, so my wife's cousin, she's, she was really big on Instagram. That's right. I was only doing Twitter. That was like, that was my channel. Um, I did TikTok for like a brief window of time and had some success there, but it, like, ate my brain.

I was just like constantly thinking of like, what's the next TikTok gonna be? And so that was like a mental health choice of like, I just, I can't do this. So I, I cut that off. Um, but yeah, so I was primarily just doing, uh, TikTok or Twitter and the newsletter and then. So, um, my wife's cousin, she actually lives like East Coast, but her mom lives where I live.

Um, and so I was [00:41:00] actually talking with her at some random family event. Yeah. And she's like, oh, you should, you should sign up for Instagram. My daughter's doing so well there. And I was like, well, maybe I can just do like the bare minimum version of like, literally just screenshotting my tweets. Yeah. And posting it on Instagram.

I did that and it freaking worked. So it was really like, it worked. Yeah, it worked really well and I was able, so I'm kind of a weird, uh, Instagrammer because I don't really do, occasionally I'll do like a reel, but for the most part, I know a lot of the, like most of the other A DHD content creators that are really big on Instagram.

They're all like doing the reels like stories. Yep. You pull up the thing of the stories and it's got like, you know, like 23 the dots or whatever. 'cause they're just posting stuff all day long and I'm like the weirdo that most people on that follow me on Instagram don't even maybe know what I look like other than my avatar.

Yeah. Because I'm just like not really posting that sort of content there. But because of that I've [00:42:00] really been able to use. My, my content format is kind of weird. It's just kind of this, like, I do like tweets, basically, like little kind of joke meme Yeah. Kind of, uh, quips or something. Yep. And that's really been something that I kind of just stumbled onto, like, uh, for whatever reason I seem to be good at this.

Mm-hmm. Like kind of connecting the A DHD experience to like, I. I get a lot of replies from people that say, I feel both seen and attacked. Yeah. I think I've

Chenell: commented that exact phrase on a couple of your posts before.

Jesse: Right. Which, uh, I love that. I think that's, uh, so, so, uh, so funny. So great. But because that text content is kind of my main thing.

I'm able to post it like almost everywhere. Yeah. And so I, so I'm on Twitter, blue Sky threads, Mastodon, Instagram,

Dylan: LinkedIn.

Jesse: Uh, LinkedIn. Are you LinkedIn? It doesn't work as much. No, it doesn't work hardly at all. I, I, I keep considering like maybe I should just turn off the LinkedIn 'cause uh, it's never, I think I have like [00:43:00] 2000 followers there.

Mm-hmm. And so it just like pales compared to where I'm in most places. Um, and yeah, I feel like. I feel like I, if I'm gonna really do LinkedIn, I need to like, have a, a LinkedIn strategy because the, the, the quip tweet sort sort of thing that I do works everywhere else. Mm-hmm. But not, not LinkedIn. It's just not business savvy enough, I think.

Chenell: Are you, are you automating these platforms together?

Jesse: Yeah, so I, I use Buffer. Okay. Okay. Yeah. And I have, I actually have, so I, at one point I, so I exported all my tweets from Twitter and I had this giant database. I before ai, AI would've really helped. I was like manually doing all this stuff to sift through that, uh, data to basically now I have a giant, uh, notion table that has like all the like tweets that I did for like two or three years.

Wow. And then I used that to help. And I have like, 'cause I exported all the data from, um, [00:44:00] Twitter. I have like how many likes it got and retweet right. And things like that. And so I'm able to like sort through that. I was really precious about it for a while, not wanting to repurpose content, and now I'm fully in on the, like now.

Oh yeah. It's like every time I post it, I, I still get comments that clearly people are seeing this for the first time.

Chenell: Oh yeah. Or they just don't remember, or they, or

Dylan: they just don't remember that too. Especially baby adhd. They might be like, whew.

Chenell: Yeah. Yeah.

Jesse: And I, I think so before I did it, I was so worried.

Someone's gonna be like, didn't you post this already? Or something like that. And I've never gotten a single one of those. That's amazing. Which is wild. I was so worried about it, and no one ever said that. And the only thing I would get, sometimes I would have somebody actually say something like, oh, I love this one, which is kind of funny.

Like, oh, they see it, they know I'm repurposing it, and they love that. Yeah. There's no problem with it at all. So it's so easy to just. Get in your head about that sort of stuff. Self-conscious and stuff. Yeah, yeah, yeah. Like the head trash. Yeah. Where you're [00:45:00] just like, yeah, yeah, it's, no, it's no good. And so a lot of that I think just like, I like to say, like start messy and then keep going.

Yeah. And so I really try to embrace that and just like, just do the thing. Find out what happens. Maybe. Maybe it's something you need to retreat from, but. It's so easy to retreat from something. Mm-hmm. And just be like, oh, that's not working. Or people don't like that. Well, I'll stop doing that and everyone will forget literally tomorrow.

Yeah. And it doesn't really matter. And so I feel like it's so easy to get in your head and think everything is permanent. Like I have to, I do that a lot with the newsletter of like, I have to have the perfect format where I've got this here and then this thing, and then I do that there, and then if I change it next week, everyone will, I don't know, be upset for some reason.

And no one cares about that stuff. Yeah. So, yeah, I think it's the, the overthinking is something I'm sure. So many of us just struggle with,

Chenell: I have struggled with that a lot. Mm-hmm. Like writing deep dives every week got very, very hard. Yeah. And so, like, I've definitely strayed away from it a little bit.

Mm-hmm. And people still love what I put out. It's like, they're like, it doesn't matter if it's a deep dive. And some people still [00:46:00] call it the things that I put out deep dives and I'm like, okay. Sure. Yeah. Nice. We'll

Dylan: call them that. Right? We are, we're right at two 30. Okay. So, um, Jesse. It's been so awesome.

Absolutely. Um, like I feel like an, you're like an old friend, like we're just like shooting the shit. Yeah. And um, yeah, we're just like really cheering you on. I think you're a great guy. Yeah. And we're happy to see you in person and hang out here. So thanks for hanging out with us. Yeah. And sharing your story, man.

Jesse: Yeah, absolutely. Thanks for inviting me. This has been awesome. I feel the same. It's just like hanging out with some friends. Uh, yeah. Just chatting about random business stuff and yeah. I love it. It is great. We'll have to do

Chenell: a round two in a maybe a year or so and see how your stuff's changed since then.

Yeah. When

Jesse: I'm like big time at that point. Yeah, that's right.

Dylan: You're already big time, but that's okay. Quickly share where people can find you and follow you.

Jesse: Yeah, so my usernames a DH, adhd, Jesse, on all of the platforms I mentioned. Sweet. Uh, which is great that I have that. I got the same one everywhere.

And then my newsletter's extra focus.com.

Dylan: Beautiful. Awesome.

Jesse: Yeah. Love it. Thanks you sir. Thanks again. Thanks.

Dylan: I think that's a pod. [00:47:00]

Chenell: We haven't figured out like an ending to the pod. Yeah. Yeah. So he is trying to steal Sam Pars like Totally. That's totally still. Oh, is that what Sam

Jesse: Par does?

Chenell: He does the pod.

And

Jesse: the pod. That's a pod. That's a pod.

Chenell: Thank you man.

Dylan: That was great. Oh yeah. That was awesome. So good.