Newsletter Coaching Session: Scaling Deep Dives Into a Newsletter Growth Engine

“$250k is when growth changes. It’s when you need systems. You usually can’t do it solo.” — Matt Gira, The Quarter
Matt Gira joins Chenell & Dylan — in person — to share how he went from building underwater drones to launching The Quarter: a newsletter that deep dives into how founders grow bootstrapped businesses to $250K. This is an interview, but also an impromptu coaching session with Matt as we help him figure out how he can grow his newsletter faster and get it in front of the right audience.
We talk content strategy, growth experiments, and the surprising data he's uncovering along the way.
PS - Matt is not only an up-and-coming newsletter creator, he's also a member of the GIR Pro community 🔥
→ Take your newsletter to the next level with GIR Pro >>
KEY TAKEAWAYS
- Why $250k is the key milestone for bootstrapped founders
- How Matt turned a niche data set into a powerful newsletter growth lever
- How he grew his newsletter to 1,200+ subscribers without chasing virality
- Collaborations, events, and the tour that could 10x his reach
- The power of being early, scrappy, and generous in your creator journey
- How Matt reverse engineers founder journeys from YouTube to written content
- The role of YouTube, LinkedIn, and in-person meetups in his growth flywheel
- Strategies he’s testing now: content swaps, data licensing, services
LINKS MENTIONED
- The Quarter (Matt's newsletter)
- The Bootstrapped Report
- Matt on LinkedIn
- Kit's Craft + Commerce conference
- Chenell's Deep Dive on CJ Gustafson of Mostly Metrics
- Ask us a question or submit a podcast topic idea: growthinreverse.com/questions
- Check out the 30 Days of Growth FREE >>
- 30 Days of Growth Course Pre-launch
- Growth In Reverse PRO Community
- Want your newsletter roasted? Submit it here.
- Check out past Growth In Reverse Deep Dives: https://growthinreverse.com/archive/
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Thanks to Tim Forkin for editing these episodes.
AUDIO - Matt Gira V2
Chenell Basilio: [00:00:00] You could get thousands like fast.
Matt Gira: I'm trying not to be algorithm driven, but I also know that's part of the game.
Chenell Basilio: A hundred thousand people on their email list, he essentially gets some of those subscribers and now they're actually paying him to write those articles.
Dylan Redekop: Let's break this down and make this like a brainstorm session of how we could help you, because I think your content's such a good quality and you do such a great job on the deep dives.
I'm like, you should have more.
Matt Gira: You should have more subscribers. More people should see this stuff. So I love you both, your thoughts on this. Okay.
Dylan Redekop: Alright. So we are here at the Kit Studios in Boise with our good friend Matt Gira. Matt, how you doing?
Matt Gira: I'm doing great. Thanks for having me.
Dylan Redekop: Yeah, our pleasure. Our pleasure.
Chenell Basilio: Excited to have you here.
Matt Gira: Mm-hmm. Yeah, this is. I'm proud to be the first in person guest.
Chenell Basilio: Yes. You get to wear that honor.
Matt Gira: I'll get a sticker.
Dylan Redekop: And we're all here because Craft & commerce, right?
Chenell Basilio: Yep.
Dylan Redekop: Um, Matt, you've been to Craft and Commerce before?
Matt Gira: This is my fourth time at Craft and Commerce.
Dylan Redekop: Fourth time.
Chenell Basilio: Wow. You have me beat. I've only been [00:01:00] three
Dylan Redekop: and this, I'm a Craft & Commerce Virgin, so this is my, this is my coming out party, I guess.
Chenell Basilio: Nice.
Dylan Redekop: Yeah. Matt, you've got, you've got a newsletter, you create awesome content. We thought this would be fun to kind of talk through what you do and you share us kinda your story of how you got to where you are and, um, what you create. So why don't you give us like a quick, a quick ish rundown of what you write and maybe why you started it?
Matt Gira: Yeah. So I, I read a newsletter and podcast about how bootstrapped companies go from zero to $250k. In annual revenue. It's really been a kind of a journey of, like originally when I first started entrepreneurship, it was like bootstrap companies are like cute little main street. Like why do they exist kind of deal.
Um, I was very much in like the tech track and ran a company called Fat. We made underwater drones, did the whole tech journey, raised money, went through Techstars, like pitch a team, John from Shark Tank, like I've. Lived it and I was like, why
did we just do all of this
and like all the work that I was doing, like raising money and [00:02:00] I'm like, this is silly.
And so then like we shut that down about six years ago now I. But then it's been like, okay, like what types of businesses are actually like beneficial to the world? Like I don't think we need another unicorn, which that might be a hot take. Um, and so like that's where I was like, and then I see, I came to Craft and Commerce four years ago and I was like, how do we build more kits?
'cause like fully bootstrapped. Like the team wasn't stressed. I'm like, you're like a startup, but not, and you're not. Mm-hmm. Like, you're like a healthy stressed. And I was like, I was always like stressed outta my mind. And so like that's where like a lot of the, like this came about in the last like three years.
Like I was like doing note code tools for a little bit. Then someone here at Kraft and Commerce three years ago was like, do you really want to work with people who don't know how to use A PDF or like work in A PDF? Right. And I was like, absolutely not. Like, that's my mother. I don't want to know.
Chenell Basilio: Sorry, mom.
Yeah.
Matt Gira: Yeah. I love you, but, um, don't want to like, I don't want to be the, you know. The Geek Squad. Yeah. Of all this stuff. So it just kind of transformed. And then last [00:03:00] year I was here and I was like, I wanna do like bootstrapped, which I was like hesitant to be like, oh, this is the, this is the place I didn't want to be.
At least that's what I originally thought. But then like seeing Kit, seeing other people do like what you're, you you've been doing and all that stuff. And I was like. No, like let's go into like some bootstrapped companies that this is actually maybe the future. Hmm. Um, and then saw Carter's data too about like how bootstrapping is becoming a bigger and bigger thing.
And then the ai, like people being like code whatever they want. So like that's where I think a lot of the pla places get into play. And the more I get into doing deep dives and how these companies build, like the more I'm like convinced like this is the way it should be.
Chenell Basilio: That's awesome. So underwater drones.
Matt Gira: Yeah.
Dylan Redekop: VC funded. Yeah. Kind of VC funded. Kind of VC funded as you look at it. Okay. Funded. Funded, okay. Thanks.
Matt Gira: Um, we were funded by Techstars, which I guess is a vc, but like I consider them more of like an angel investor. But anyways, that's semantics. Um. So, yeah, we made underwater drones. We are known, like, we were like, we just like, basically the infas, like our drones at the time [00:04:00] was 2015.
Like, so they were just kind of coming online and like they were the big thing. And then I was living with a couple guys and they're like, okay, like what if we, instead of it in the air, like, could you go underwater? Um, because it was like, they like being, I'm originally from Michigan, so the whole thing was like.
Oh, like could we go explore like the Great Lakes, or like all the little lakes in Michigan were just like, probably have tons of like little, you know, secrets and histories and shipwrecks, all that kind of stuff. Mm-hmm. And we're like, yeah, let's see what happens. 'cause no one else was really in the market.
And then we're, we, were dumb enough, like we, this is like the dumbest startup. You really look at it like bunch of college students, hardware and consumer product, and no recurring revenue. Like we are the, the epitome of like the worst startup idea you've ever heard. And we actually like got pretty far for what we did.
Wow. Um, because we did like huge kicks in our campaign and like actually shipped 600 units.
Dylan Redekop: Nice. Really?
Matt Gira: Yeah.
Dylan Redekop: So. I mean that feels exciting and like a bit of a success to what happened basically.
Matt Gira: So like we got to the end of 2018 [00:05:00] and we had just shipped and we were running outta money, but I was like to our investors, like I did like a monthly investor update.
We're gonna take whatever funds we have left, all the resources we have, and it was like, it was like October and I was like, we are gonna like. Just spend it all because if we can't sell during the holidays, like
what are we doing? Mm-hmm.
And we did okay. It wasn't like super thrilled, but it wasn't like super awful.
But then almost every single unit was coming for back for different reasons, for technical reasons. Mm-hmm. Like, oh, this one leaked, this one's got a badge, whatever. Like it was like wasn't on the manufacturer or anything like that. It was totally on us of like this bad design because it is like, again.
College students building. And were you guys like engineers? Most of the team was, I have a degree in chemistry, so like I know, and I've taken enough engineering courses to be dangerous. Okay. But like if you asked me to build that drone, probably not.
Dylan Redekop: And did you build that drone?
Matt Gira: I did not. Okay. There was other people doing it.
Okay. Um, I was on the business side of things and like learning all this stuff about like, oh, you have to do this with investors. Oh, you should actually build relationships [00:06:00] first. Like,
Chenell Basilio: and now you're. Working with Yale too. And you have been for a while.
Matt Gira: Yeah. So ended up, yeah, shut down the startup. Like did like a free agency year is what I call it.
Right after that it was like consulting and on the side found myself back at Yale. 'cause I interned there to go through like their summer program at the time in 2015. And then it's like morphed into like, yeah, now I lead student entrepreneurship at Yale. Essentially, and it's like a wild ride to see like be the person that's like making sure the food arrived to this program and now it's like, oh, you lead the whole thing.
Dylan Redekop: That's really cool. That is cool. So now you are diving into how other bootstrappers are getting to that first 250 K in revenue. So one of the first things I think of is Y two 50 K,
Matt Gira: two 50 K. So it's really a big moment. I think, so one was like when I looked at all the research around like, okay, where like, like Kit has their crater like report they do every year.
Mm-hmm. And they mark two 50 K as like this big number. And then if you look at other like industry reports, like two 50 is always like a. A number. And I was like, why? And I started talking to [00:07:00] founders and like, like started talking here at Craft and Commerce and it was like, oh no. Like that's when things change.
And I was like, why do things change? And it's one is because like your growth is different. Usually at two 50. One is like your growth, like the way you can grow is way different, right? Because you're not like scrapping and calling, like there's has to be systems to get to two 50. And then two is like, you usually can't do it on your own at two 50.
Hmm. Like sometimes. These days, maybe it's more acceptable, but like it's pretty rare when you can do it as a solo at 2, 2 50 and above. So you like team building's becoming a thing, like it just all the numbers change or the things like the systems and like how you operate changes
at two 50 for most.
So.
That's where we're at. Two 50.
Chenell Basilio: Very cool. When did you start this whole newsletter? And now this podcast, right?
Matt Gira: Yeah, this was July of last year when I like did the first like, kind of pilot, like, let's see what happens. Okay. And I did it on Nathan, but not his kid story. 'cause I was like, I want to interview Nathan to get that one.
Yeah. Um, but like totally like nerded out Nathan, like so hard, like, like you do. And I was like, I [00:08:00] feel like I can like hear Nathan in my head at this point. Mm-hmm. And yeah, like got really good reception from like people, like it was like as texting people, I'm like, what do you think of this? And yeah, like now it's just like lots of good feedback and it just kind of snowballs from there.
Chenell Basilio: Very cool. So less than a year in, yeah. What are we, 11 months? Something like
Matt Gira: that. Yeah. About that.
Chenell Basilio: And how many subscribers are you at? What are you? Yeah. You've had some changes happen recently too.
Matt Gira: Yeah, quite a bit. Um, as of 36 hours ago, the website's finally updated. Yay. Okay. Awesome.
Dylan Redekop: Um, so talk us through what it, what you originally launched it as, like name-wise and brand-wise and where it's at now.
Matt Gira: So the whole brand has been like called Station because I've always thought about it as like a train station. Like I can build lot hubs and like, there's a lot of like different brand plays off that I think. But that doesn't really accurately say like what this is for.
Mm.
And so last three, three months, I was like, I gotta rebrand at least, like create a brand underneath that.
And I was like, what? Like we've, yeah, we've been talking and then you said the quarter and I was like, darn it. That's it. Um, and then like I [00:09:00] started passing that around and they're like, yeah, that's it. Like it's simple. And it's like super catchy. Like it just got a lot of things. And then the logo thing was like so easy 'cause it was like, oh, just a pie chart in like a quarter.
Nice. So that's all played out Nice. And now if you would've joined the quarter.com, it's all there. Amazing. Three, six hours ago.
Dylan Redekop: 36 hours. It's exciting. Okay, so now walk us through, you've been doing this for 11 months, maybe talk to us a bit about your content. 'cause you take a really in-depth approach, both in the.
Written component, but you also go a layer up with the podcast. So, um, what does like your typical deep dive kind of look like?
Matt Gira: Yeah, so typically it is the, the normal structure of it is doing like the story of like the founders that you have some context. Um, it's also like you get little tidbits of like, oh, didn't even know, like there's been people, I'm like, I'm friends with you for the last like decade.
I didn't even know that was a thing. Right. And so getting that story. And then also I think there's so many unique tidbits I think that you pick up. So they usually, I try to do like their story and like one, like kind of, you think that's really unique to them. Um, so like there's [00:10:00] one that's coming out of like, finally someone was talking about bluish strategy.
So like, I'll talk about a little bit about that too. So like, there's just like some concepts I'll kind of bake into 'em. And then the last half of it is the growth strategies. Like how do they actually do it because like. As you probably have seen, like no one talks wants to like, I don't think it's intentional.
They just don't really talk about like, hi, here's how I did it. Mm-hmm. Or how I actually grew it, especially for bootstrap people, because they're just like, oh, no one cares about my story. Or like, yeah, when actually like press isn't necessarily reaching out to them. They're reaching out. Like if you're backed.
Then you can talk about it and it's like, well, that's like 0.1% of all companies. Um, so like me coming, like, I might be one of the first people that have actually asked like, okay, how did you actually grow this? And you just get like this huge list of stuff. Hmm. Or if it's like really simple and you're like, that's the whole thing, they're like, yeah.
Um, so that's been like the, yeah. So showing the growth strategy so that way people can go implement them on their own too.
Dylan Redekop: Okay. And you are not, 'cause with Chenell's. Um, newsletter. She is doing a lot of just like total secondary research. Like she's going [00:11:00] through podcast episodes, articles, they've written any, anything she can dig up on the way back machine.
Right? Yeah. Um, but you've taken more of a primary research approach where you're actually like interviewing these people, right? Yeah.
Matt Gira: So I, I'll do a little bit, but not to this extent that you do. And so like I'll research, I'll do the way back machine, but like there's only so much you can get, I think, from a lot of these founders.
Yeah. So like if I'm in person, like I now have like a mobile studio in my backpack. Amazing. Love it. And so I can go record with people in person. Um, and I'll do a little bit of, especially if they're like a creator, which like a really cool studio, I'll be like, we're recording virtually. I wanna see your studio in
all of this.
Nice. Um, so like that's been super cool. So yeah, I'll interview with them and just kinda like it's me like. Putting some of the pieces together. 'cause sometimes there's like, oh, like I have this piece, but like, how does this connect to so such and such?
Yeah.
Um, and there's some stuff I'm like, okay, I would've never found that.
So that's been super cool. And like, there's definitely some bias. I know, like, like you've been like, oh I don't wanna talk to people 'cause of the bias piece. Uh, 'cause they're like, they have survivors bias or all [00:12:00] that stuff. Yeah. There's some of that that I have to like, okay, there's like, I need to weed some of that out.
Mm-hmm. Um. But like, yeah, that's me doing the, in the interviews has been super cool. Um, and being in spaces, I'm like, I never would've been in here.
Chenell Basilio: That's awesome. Yeah. So are you seeing that they're sharing your piece of content after you write it or after you publish it?
Matt Gira: Yeah, a lot of 'em will. Um, but it's been, it's been interesting 'cause a lot of 'em will person post them on their personal.
Like channels rather than their business ones. And it's interesting 'cause like they, they're like, here's my story. 'cause a lot of their friends and family might not know their story. Yeah. Oh, okay. And so that's been curious to see some of that. Um, the interesting piece too is like, not all of them, not all of them have right, like the newsletters and things like that.
They, a lot of 'em have like, maybe like YouTube channel or maybe they don't even have a social media presence. Um, so like they will share it, but like, it's been hit or miss of like, actually if it, if it's been helpful or not.
Chenell Basilio: Very cool. Um, how many subscribers are you at today?
Matt Gira: I'm at. Little at 1200.
Chenell Basilio: 1200.
Okay. So small but mighty.
Matt Gira: Yeah, we're getting there. [00:13:00] We're getting there.
Chenell Basilio: Yeah. And you, I think you started this as a YouTube channel first, right?
Matt Gira: Yeah. It was more of like a YouTube channel. I wasn't gonna be a podcast, and then I asked everyone, including the newsletter, like I was like, all right, is this a podcast?
Just like really silly question. Yeah, I was, I thought people would be like very mixed debate. It was like clearly a podcast, like no one put No
Dylan Redekop: that was in the community when you asked that. Or just the newsletter. I could
Matt Gira: put it on LinkedIn and on my newsletter and everyone put yes and I was like, oh, I need to go.
Get this a podcast feed. So,
Dylan Redekop: so how does it change your approach? 'cause when you talked about YouTube and you talk about podcasts, and some people might be like, wasn't that the same thing? So how does that change your approach when you're doing the interviews and stuff?
Matt Gira: Yeah, so like, 'cause I've always seen it as like more of like a TV show type thing.
Okay. Yeah. Like on YouTube. Yeah. But I guess like podcasting is transferring to that a little bit. Mm-hmm. Um, 'cause I'll do more like, like there's slides. There's me drawing in some of 'em, like yeah, there's a lot of like the visual components to this. Um, I try to show like the websites or like the B-roll, all that kinda stuff, which you don't see in the podcast stuff.
[00:14:00] Um, but I guess you do get majority of the content through just like listening to it. So I get why people think it's a podcast as in like why that's a valuable thing. But definitely the best experience is through YouTube.
Dylan Redekop: Yeah, by far. So do you take just the audio basically of the YouTube video and turn that into, yeah.
Yeah. Okay. So you're not doing a whole other take and No, I guess this is a side project for you, so it's not exactly like you can spend every waking hour on it. Yeah,
Matt Gira: and so like if there's been like small little tweaks, I'll be like, like subscribe at the end of the video, whatever. I'll be like, subscribe at the end of the episode and
Dylan Redekop: like, right.
These little things. Interesting. So. Are you monetizing this or do you plan to, and if so, how? Oh, that's
Matt Gira: the
Dylan Redekop: million dollar question.
Matt Gira: Well,
it could be, it could be the million dollar question. Um, yeah, so right now it is not monetized. Okay. Um, I just have like affiliate leagues, which like pay for the software.
Interesting enough. Nice. Okay. But yeah, the ultimately, I like the vision is like to build like an incubator program so we can build from 0 2 50. Um, and so what that looks like, like TBD, but that's ultimately like how do we help people go from zero to two 50 and build a really cool business? [00:15:00] And if they going beyond two 50, that's even better.
Chenell Basilio: So when you think about the people you want to feature, are you. Obviously they've hit two 50. Yeah. Uh, are you thinking about like software or media or like what kind of businesses are these?
Matt Gira: Mm-hmm. Yeah, it's a little bit of everything. It, that's, at least I'm trying to do. It's re it's so easy. Just like grab creators.
Yeah. Yeah. 'cause they're just like here. Yeah. Um, and like those are friends and all that kinda stuff. Um, but yeah, like, it's been so interesting 'cause like a friend of mine does like a, like the last deep dive I just did is like silk screen marketing and they like screen, screen print, t-shirts and all this kind of stuff.
And I was like, I didn't know. This is like such a like robust system. Hmm. Um, and like you could make two 50 K off this. Um, so some of that, um, the retail stuff has been super interesting 'cause like I feel like they get to two 50 so fast, but their profitability's a lot different.
Dylan Redekop: Right. So we're talking overall revenue when we're talking two 50 k.
Yeah. So
Matt Gira: I don't even like ask for profit 'cause it's like. It's such a, it's touchy. It's a touchy and like all these different things. Um, but like, it's been interesting to [00:16:00] see like, like I did one in, on a company that does like, it's kinda like, sounded like paint and sip. It's like candle making and zip.
Um, so that was like super interesting to see like, okay, like you're in a mall, like malls are supposedly dying, but like here you are like killing it. Um. And then I did one, it's like actually they shut down. And so talk about that story too.
Oh, okay.
Um, and then, yeah, there's like creators too, like Chris and Sarah.
They're like a travel vloggers, like how
Dylan Redekop: do you make money traveling and those kind. Yeah. I think what I find really, um. Alluring to your content is not just always the exact same kind of persona in story. It's you're mixing up from people who are like traveling the world in an RV and making money somehow doing that as creators to people who are doing silk screen printing and stuff like that.
So you, I think that's kind of a, I. It's a nice angle and it's kind of a refreshing approach. It's not just always kind of the same sort of cookie cutter story.
Matt Gira: Yeah. 'cause I've also have been thinking about like, okay, like location wise, right? Like I'm in mostly the Midwest and the East coast, but like, what's the West coast look like?
Right. Like, right. So I'm trying to put, like, I, I'm thinking more about as like a data set in a lot of ways, [00:17:00] or like a library.
Oh,
okay. And then that, like, I have like a better picture. 'cause the, the other thing I've realized is like, this is, this is building a really unique data set. Mm-hmm. That like no one really has.
Hmm.
Um, like the growth strategy is like how, like where they, like I have all this different stuff and like, that's the piece that's been even more interesting to
Chenell Basilio: me. So have you found it hard to grow the newsletter and YouTube channel because it's so diverse and there's not like a set person that's like perfect for this content?
Matt Gira: I think it's, there's some of that for sure.
Chenell Basilio: Okay.
Matt Gira: Um, I think the other thing is like, there's just like all the, I don't know if stigma's the right word about bootstrapping, like my original like thesis about bootstrapping is like. A lot of people's like mindset of like, oh, it's like it's cute. It's not really worth it.
There's like a lot of like economic development, like. If you like the other like entrepreneurial support organizations, right? They'll be like, oh, you's moving money around is what their theory is a lot. Which is like not true. I have like a lot of like stories I can show like here's how this is actually building your community and [00:18:00] ecosystem, innovation ecosystem.
So like there's just been interesting like conversations around that and people not taking it as seriously, I think as a pathway. But it's interesting is like people who have built a venture backed company and like maybe they, you know, shut it down, all those kind of things, like they've been like, oh, I get it.
And so that's been interesting to hear some of that feedback too.
Chenell Basilio: So how do you plan to grow this from here?
Matt Gira: So that's been like the. The now that like I have like kind of like, okay, here's, I think what good is good, good content. And the brand is like in a decent, like I can pitch this in a decent spot. I think the growth strategy is like wanna get on different podcasts.
Mm-hmm. Like this one,
um, two check. I got one. Yeah. Um, but then two I think is like, keep doing YouTube, do LinkedIn. Mm-hmm. Um, LinkedIn, I have like a. That's my biggest following in some ways. Yeah. Okay. Which isn't huge. It's only like 4,500 people, but I get decent engagement. So I think just like really leaning into that, even though like I have mixed feelings about LinkedIn.
Mm-hmm. Um, don't we all? Yeah. Don't we all? So I think it's just kinda leaning into some of this. And then what I'm also realizing is like [00:19:00] the data I'm getting is also like a pathway for myself. Um, one of the things I've really learned is if you're building with others, you move so much faster to two 50 k.
Um, so like what the data I have is like if you've to get to two 50 k, the average time to get there from zero to two 50 is about two and a half years. But if you're building in a community with others, it's a year, almost a year shorter.
Chenell Basilio: And that's just like having people around you that are doing something similar or is that like co-founders?
Matt Gira: It's like, yeah. Building around you. So like, it might be like you're in paid communities. Okay. Or like you're working with like other platforms like Hacker News or. Um, like, yeah, so like as long as you're like in a, in a community and there's others working with you and stuff that might be like sharing your content too.
Like that's when you like speed up like crazy.
Dylan Redekop: So like collaborations and that sort of thing. Yeah. Yep. So maybe before we figure out how you're gonna grow this further, how have you gotten to the 1200 subscribers? Like what, what have been your biggest growth growth channels? So, one
Matt Gira: was re most recently is the Bootstrap report.
Okay. Um, so I did like, kind of took like the [00:20:00] first like 50 or so businesses that I, I've done research on. Put them into like the data set, like very, like, here's what they are. And like the growth strategy is like the most used and all those kind of things. Um, that's given me about 150 subscribers in the last like few months.
Okay.
Um, and that was like posted on like Indie Hackers, like it was the top hit for Indie Hackers for a little bit. Um, so that drove a good amount. And then just being shared out too. Um, there's definitely some word of mouth elements. I can't figure out where they're coming from. Yeah. Hmm. Um, and then the other piece is like creator network with kit.
Um, there's been some other creators who are like, Hey, I'll just like recommend you, and they've submitted, they've sent me a, probably like a third of that list. Okay. Um, and then the rest is just YouTube. 'cause I was doing like Airtable content and notion content and like your typical like tools and things like that.
Mm-hmm. Uh, with like, here's a template, here's like this, like all that kind of thing. So that's probably where the like 500 of the list or So
Dylan Redekop: from YouTube, do you do, uh, call to action to get your report, your bootstrap report in there or? Yeah.
Matt Gira: So now the bootstrap report's everywhere. Like it should be hard to miss.
Dylan Redekop: [00:21:00] Okay. Okay.
Matt Gira: Yeah, it is like everywhere. So it's in all the blog post now. It's on the YouTube channel, it's in LinkedIn like crazy. So like ultimately, like I'm trying to drive everything through that because I think that's the best resource. Like in terms of like, okay, here's what, 'cause if you like the bootstrap report, you're gonna like the content.
Mm-hmm. And so, but if I did like other lead Mannings, I don't think you might stick around like the people that are like signing up for like, oh, here's a free financial model. Like. You probably don't care about the deep dives. Yeah, you didn't come in through that.
Dylan Redekop: Okay, so plans for growth. What's worked is YouTube and Bootstrap Report.
We could probably put those at number one. Two. Yeah. So where, what is the next, if you had to plan out like the next six months-ish of growth strategies, what would you, yeah. Or, or do you, let's break this down and make this like a brainstorm session of how we could help you, because I think. Part of the reason Chenell's, I told Chenell, I'm like, I think we should have Matt on.
Yeah. And she's like, I agree. And because I think your content's such a good quality and you do such a great job on the deep dives. I'm like, you should have more, you should have more subscribers. More people should see this stuff. [00:22:00] This content is really good. And you put so much effort into it. It's not just something somebody's doing like, you know, for an hour a week kind of thing.
It's, you've put a lot of time into it, so I want more people to see it. So let's like get in front of more people. How, how can we do that? What, what's your plan for, for that? I would,
Matt Gira: so I'd love you both. Your thoughts on this. Okay. Like. I, that's part of like, the question, like this month is like, how to do that.
And like, so the collab has been on my mind. Mm-hmm. It's, I'm doing a little bit, um, actually today on LinkedIn, I was like, let me see if I can, can I package these? Yeah. Those people stuff, does that send stuff? Um, so kind of experiment with that. Everyone seems to be like, Matt, you need to go on a podcast.
Mm-hmm. And I'm like, okay. Interesting. So, and then like YouTube, YouTube is just such a commitment. It's, I feel like it's that that's like the hardest. Platform to really do it at like a really elite level. But yeah, I'm trying not to be algorithm like driven, but I also know that's part of the game.
Chenell Basilio: Okay.
Well, YouTube also has Evergreen, which is nice in a sense of like, yes, it's harder, but it lasts way longer than a LinkedIn post or anything. So, and I feel like I. When I first saw your content [00:23:00] start to like the new stuff 11 months ago, I was like, his YouTube channel is really good 'cause it's just you spend the time to make it.
Mm-hmm. Good. And like a good quality and you know, I'm all about that kind of insanely valuable content. So yeah, I do like that you're doing YouTube. I'm sure it's really hard though. Have you thought about like. Not that I'm suggesting this, but paid ads at all.
Matt Gira: It has in my mind. Um, I think it's been like, okay, what does that look like?
Yeah. And then what's the flywheel if there's no revenue coming? Yeah. So I think that's the piece of like, alright, do we do like the incubator now? I. So like, that becomes more of an option too.
Chenell Basilio: Are you ready to start the incubator?
Matt Gira: I don't know. Uh, I want to, I really do. I I think there might, I might be ready.
Okay. Have you been part of one
Dylan Redekop: before?
Matt Gira: Yeah. I mean, I've, I haven't, I mean, I've been part of a bunch of incubators.
Dylan Redekop: Okay. So you know how they, you know how they operate, how to run one, probably them for like a
Matt Gira: decade now.
Dylan Redekop: Dude, you're ready. You're
Matt Gira: ready? Yeah. Um, like I have, I, uh, there's a really good friend of mine.
He is like, Matt, you're just a walking Rolodex. [00:24:00] I'll just be like, oh, you should meet so and so. Yeah. And so like that part of it is just comes natural to me. I think it's more of just like, okay, who's actually paying for this? Like, who are like the first 10 or so people? I. And then going from there and like really be like doing that, doing the initial pilot seems to be like the, the har the snowball effect.
But that's the hardest lift it feels like. Yeah. Zero to one. Yeah.
Mm-hmm.
Chenell Basilio: And you're probably gonna have to take a little bit of a break from content to start that. Maybe Potentially,
Matt Gira: yeah. Or like get so far ahead in content.
Chenell Basilio: Do you think there's a world where you would do like services of like helping someone who's trying to get off the ground and like just give them part of your Rolodex?
Maybe.
Matt Gira: I've thought about that too. I think it's been like, okay, what does that actually look like? Mm-hmm. It just like, like. Product I service is also a thing I've learned. Mm-hmm. It's like where everyone's like, does really well. So it's like, yeah, what does that look like? But maybe that's like a, a like a one of the tiers of the incubator too, where it's like more like one-on-one support too.
Dylan Redekop: Yep. So what you could do, just going back to the paid ads idea, the Bootstrap report feels like a really good lead in, right? So advertising [00:25:00] that and then then in the backend, the flywheel, so to speak. Shane talked to us about this morning. You can just have. A start pitching this incubator. 'cause the people who are gonna be interested in, in a bootstrap report are probably gonna be at least interested in a, in an incubator of some sort.
Chenell Basilio: Here's my other thought. So Dan Runcie does the business of hip hop. Oh yeah. And he has a report, which is free. But then there's also a higher tier for industry professionals. I have to wonder if other VCs or investors are interested in the content you're creating and like the data set that you have. I almost wonder if there's a way to create a free version, like maybe you update it soon.
I think you just released it a couple months ago, but um, maybe the next time you update it, you could do that or get some sponsors for the report and then that could. Maybe there's a way you could do like a, I don't know, like a hybrid model for sponsorships. Like here's the base, uh, package to get you in the deck or the PDF or whatever you're selling it as.
And then it, as we add, you know, a hundred more [00:26:00] subscribers or 1500 more subscribers, they like start, I. I don't know how that would work, but I'm just riffing here.
Matt Gira: No, I know. Like, um, Richard Vander does the LinkedIn one. LinkedIn guy. Yeah. Um, he's been interesting 'cause yeah, I'm like, I don't have the data set you have, but like, that's where I feel like I'm trending mm-hmm.
In terms of the data. Um, so yeah. What does that look like? Yeah. And so I'm kind of like, I've been like, anytime like someone has a report or like does anything like community-wise and like building in public, I'm like, oh, safe.
Dylan Redekop: Yeah. What is your biggest challenge you're facing, like right now?
Matt Gira: I think just like growing the newsletter, I think it's like the growth side, like what's the system that like really grows this consistently.
Okay. Um, LinkedIn, like I feel like can get lots of decent amount of eyeballs on stuff. Mm-hmm. But like does that translate to newsletter growth?
Dylan Redekop: Yeah. Would you say that, I mean, LinkedIn is a professional network, so you'd think somebody who's trying to bootstrap a business would probably be there to some degree, but have you found that to be the case?
Matt Gira: Yeah. So there's a lot of like, right. LinkedIn's known for the lurkers and so I have a lot of that. Because when he's coming in per like, I'll be in person [00:27:00] and stuff and they'll be like, oh, I saw that content. I'm like, I didn't even know you existed. Yeah, right. Or like, I didn't know you were watching.
Never even hit like before. Yeah. Yeah. And so there's a lot of that. And like they're not in the newsletter. They're not. So that's why I'm like, I can't abandon LinkedIn completely. Mm-hmm. Um, because it is hitting the right people a lot of the times.
Dylan Redekop: Yeah, definitely. So in terms of collaborations, 'cause you did touch briefly on that podcast is one way to do it.
We've done some cross promos together. Um, what is another, is there more of a meat on that bone that you could, you could chew on? So the
Matt Gira: one, right, like I do most of my like, so the like, right. A lot of what I know is like in person.
Chenell Basilio: Yeah.
Matt Gira: So it's been like, okay, like is there a way to do events? Is there a way to partner with other organizations, especially to put on events, um, especially with like the local, like entrepreneurial support organizations.
Um, they're always like looking for people to do events with. Um, I think it, like, there's, that, that's a different time commitment, but you also get like a deeper level of subscribers. So it's like, it's the ROI piece of it, of like the quality [00:28:00] versus quantity thing. Um, and like is the ratio right, I guess.
Dylan Redekop: You were looking at doing a tour Yeah. This spring. Right? Walk us through that idea. 'cause I thought it was a really cool idea and, and you told us about it, uh, a few months ago and then it kind of fell off. But just walk us through that idea. 'cause I think that's like a form of collaboration. It's like a form of a bunch of things like collaborate, collaboration.
In events in person. So talk to us a little bit about that because I think yeah, maybe, maybe next year you might be able to take, take that one off the ground. Yeah. Fingers crossed. Fingers crossed.
Matt Gira: Yeah, so the whole idea for the tour was, okay, if I can go tour around the, the country, like go to these different cities, go to the different co-working spaces, incubators, those kind of things.
Go one, go interview people that have done two 50 K in person, those kind of things. Like maybe have a full backlog for the year. Mm-hmm. Don't have to record the rest of the year.
Yeah.
So that was one angle of it. Two was like, yeah. If I could do, like, do the, essentially do the interviews like in person, maybe in front of like, some of them do them in front of an audience.
[00:29:00] Right. Do like a fireside chat. Do the first part of it as like the content for YouTube. 'cause what I do, I don't do it like straight con like, 'cause not every founder's great at interviews. Um, so I'll like interview them and they'll, I'll cut it up and like, then like put it, piece it all together. So if I took like the 20 minutes of that fireside chat to get, okay, here's what I need, and the rest could be just like, more open q and a.
That seems to be like a, like a really good fireside chat, I think. And you'd get like, if you know the newsletter, which isn't a ton of people obviously, but like if you know that like you're gonna see the format and like be able to do all that. Um, so like that felt like okay, that could be really catalytic in terms of like getting in front of people, all that kind of stuff.
Um, and if I can get content recorded for like a year, that would be.
Dylan Redekop: Incredible. That's almost the value to you selfishly, like Yeah. Yeah. And also
Matt Gira: just like get out and like go hear from people. Mm-hmm. Mm-hmm. Like what's the piece that's like most helpful or all those kind of things. And also, right, if you're building community, right?
Like being in person with people is like so much better than digitally.
Chenell Basilio: I'm curious if you've thought about, I [00:30:00] don't, I don't, this is always on my mind lately, but CJ Gus of mostly metrics, he does like sponsored. Posts with brands. So he will go to a brand and say like, Hey, let me write an article for your newsletter.
He, they have a hundred thousand people on their email list. He essentially gets some of those subscribers and now they're actually paying him to write those articles. And now, I mean, he doesn't even have to create net new content like they're just sharing his stuff. I'm curious if there's a way that you could take something from that and maybe go out to software companies or startup like that, cater to these founders and say like.
Hey, let me like write something for you and like those are your people on their audience. I have to wonder if there's something there.
Matt Gira: Totally. Um, 'cause I'm doing like one pilot. Um, so basically there's a group called Midwest House. Okay. In the Midwest, they're like this, they cover the Midwest obviously, but it's like all the Midwest startups and like they do a big event.
I think they're biggest event. It's out, it's at South by Southwest and they get like 3000 people within like three days. Um, but they do a newsletter on [00:31:00] Substack and they were like, well, what if you just like. Posted one of your deep dives in our newsletter. Like, you'll own the newsletter for once a month.
That's interesting. And so like, we're kind of piloting that to see how that goes. Okay. Um, but yeah, like the other thought has been like, as a prioritized service has been like, okay, what if I did like the deep dives on other centers and other, like for companies and things like that? And then if I could get the rights to that data, that gives me a whole new data set too that I can keep building off of.
Mm. Because I, the one thing I don't have right now, which I love to have, is like the venture backed data. Of like, can I do apples? Like compare them right. And be like, are these different, how are they, like, how are they different? And that like, I don't really wanna do the content on them necessarily. Yeah.
But I want the data. Yeah. Um, so that's a piece of like, what does that look like? But also like, right. These reports, I feel like are a really good lead magnet for so many people, um, especially with these B2B businesses. So like, I'm really comfortable with 'em. They're really fun to do, even if they're not necessarily like my, like the bootstrap people.
Mm-hmm. [00:32:00] Um, like if they're, if they're about the companies and I can like. Do that. I think that'd be sweet.
Chenell Basilio: That would be super interesting. Mm-hmm. Because I feel like that's just a way to get in front of such a big audience quickly and like you're not doing cross promos and getting like 20 subscribers here, maybe 50 there.
Yeah. It's like you could get thousands like fast.
Matt Gira: Yeah, and I think there's just like, okay, who are those groups that like need that data and like how much time does it, time and effort does it take to go get those reports done?
Chenell Basilio: You could also create like, like pitch one of these companies. Go to them and say like, Hey, I have all this data.
I wanna write a report for you on like. The top 10 ways. These people, these bootstrap founders, are growing something that would help their readers and they would kind of see value from, and then you don't have to worry too much about the data right away. And it's, it's still coming from your data set.
Matt Gira: Yeah.
Chenell Basilio: And then you can kind of like pitch the founder of the bootstrap founder report as like a lead magnet. Yeah.
Matt Gira: Yeah. I think there's a lot of stuff like, like Chambers of Commerce are interesting to me. I don't know a ton. They're kind of outside my normal world in some ways. Um, so [00:33:00] it's like, is there a play with them too, because they're like, they have these huge.
Amounts of communities and things like that. Yeah. Um, yeah. Is there a way, like, because a lot of the times, like a lot of these organizations, right, they're like, h how do we show that? Like, we're actually valuable because like the data's hard for them to get. So if there's a way like that, I could do that for them.
I think that's a big value to you for them. But
Dylan Redekop: then it's like, is that distraction? I don't know. How do you think about other colleges and universities in terms of growth? Because. I dunno why it just occurred to me now, like a bootstrap founder is probably like a third, fourth year, um, student potentially.
Right. So have you gone down that rabbit hole at all? Yes. I feel like because you work at a,
Matt Gira: you work at a university. Yeah. I do feel like I have a lot of hot takes about universities. This say. Oh, okay. Okay. Um, I think the bootstrap founders, I think that like, it just, we don't talk about it enough at the university level.
It's like, 'cause all the VCs and everyone just like clamoring for like the venture backed companies all the time. Mm-hmm. There's a value to [00:34:00] that. 'cause I think there's like excitement and like that like, oh, I can go build the next, pick a company. Right, right. Yeah. That's like a, it's a nice little carrot, but then like they are like, right.
Like I was like, where are the worst nightmare for vc? So it's like, okay, we're dangling them and like expecting them to do that. But then they're measuring it off of like how much money they've raised. So like they like, they might go raise money. Like kind of we were like, go raise a bunch of money and like, we're like a cool story for like a year, but when we flame out we just like disappear and then you move on to the next.
Mm-hmm.
And that's not like a good ecosystem bill there. And so like that's where it's like how do we support the ones that are actually gonna build something that lasts for longer? And so like, I think about that quite a bit because the other thing I've learned with the Bootstrap report, particularly like the, one of the things I've measured was years of experience.
Dylan Redekop: Okay.
Matt Gira: And what I learned was like, you need, it's about eight and a half years of experience typically when they start their, like the business like gets 'em at two 50, which is about 32, which is about where I'm at, age 32. And so it's like, which makes sense based [00:35:00] on like my own optics, I think it made sense.
'cause like, oh yeah, like you start your first venture, go work, go make a little bit of money, you get sick of that and then you go move to your like go build a venture. So like that all like put together like made sense to me. So I think it's the group that's after they leave university. Okay. I think.
Dylan Redekop: But like, how do you do that?
I don't know yet. So your target newsletter audience would not necessarily be university students? Not
Matt Gira: necessarily yet. I think some of them will be like, I, I keep saying like there's gonna be a university that figures out like, Hey, boost rep companies are like a focus. And I, I think it's gonna be someone that doesn't have a big VC space.
Okay. Or big VC network around it. And they're gonna absolutely crush. 'cause like you don't have to worry about the VCs necessarily. You can, like, you have to pitch differently. The communication's gonna be a lot different. Um, but like you could build a really, really cool local ecosystem just with doing the focus on that.
Chenell Basilio: I still feel, yeah, I feel like the brand angle is great. I think the tour. It's gonna be amazing if you do still want to do that. [00:36:00] I think it, it's just like, I remember a friend of mine did it, I don't know, 2016 or something and he went to all the credit unions in the us Uh, it was more about like personal finance and stuff, but I think there's an angle there where it's just like compound and you build like every stop that you're at, it's like people talk about it more.
There's more like. PR and like images online, and it's like creating a sense of fomo.
Matt Gira: Totally. Right. And then like yeah, the PR angle, right? Like, it's such an easy, especially if there's founders, like, um, like I just did, I haven't published it yet, but there's a deep dive. It's an agency that runs, they do $30 million in revenue.
They're fully bootstrapped. He is never asked to be on a fireside chat, which blows my mind. Hmm, wow. Like, blows my mind that no one knows that. Like, like they, they're like, oh yeah, like we know them, but they don't understand. Like what they've built and then what size is it's at
Dylan Redekop: like the impressiveness of it.
Yeah. Yeah.
Matt Gira: And I'm like, he should be on a fireside chat, like monthly in this community. Like there's not many of him. Um, he's available. Like that's the crazy, like
Dylan Redekop: And [00:37:00] you've and you interviewed him?
Matt Gira: Yeah. Yeah. Like, he's been a mentor of mine for a long time and I, I was like, he doesn't talk like he doesn't do any events.
Yeah. And I'm like, like people might know who he is, but like he's not this big. I think, but if he was like venture backed, he would be talked about all the time,
Dylan Redekop: right? 'cause that's sort of a sexy headline, right? They raised $50 million from a 16 Z or whoever. I think it's
Chenell Basilio: more sexy to have that headline.
I agree.
Dylan Redekop: I agree. It's like this guy
Chenell Basilio: built this business by himself and like figured it out and now he is sitting on this like $30 million project.
Matt Gira: Yeah. And like just, they do incredible work like crazy. I feel like every time I talk to 'em, there's like crazy stories in such a good way. And I'm like, how are you not in front of a mic all the time, but
Hmm.
Chenell Basilio: Do these people all hang out in like a specific community together? Is there like anything that Not really.
Matt Gira: They like, maybe they'll go to chamber events, kind of here and there.
Chenell Basilio: B, B and I type things. Is that even a thing for those folks? Yeah.
Matt Gira: Yeah. Like if they're doing, like, they'll do a little bit, but a lot of times they're kind of solo or like their network is [00:38:00] outside of their local region too.
Mm-hmm. I've learned like, oh, they met 'em, like there's this conference they go to and that's really just like hang out. So it's just like, it, it just pockets everywhere. Um, or like there's a, yeah, there's a, um, another group which like, now I've featured like three or four of them, um, together. But basically like, there's like these networking groups that like people sign up for.
And they just like keep relationship. Like there's this full network of people, like of deep dives, like there's brand Bruski and then like Aaron Roland Hagen and Eduardo pae, like they were all connected. They're not even in the same vicinity. Like Aaron's in Iowa, city of all places. Brandy's in New York or New Jersey, New York.
Um, and then, um, Eduardo's in New York. But like they're all just like super connected and like that, they're just talking all the time.
Chenell Basilio: I wonder if you can go to these conferences and just like hand out, like. Stickers or something like
Matt Gira: stickers or like me just like sitting in front of like a bench with studio and like, Hey, anyone wanna sit and ta talk with me?
Dylan Redekop: Yeah, yeah. Holding your funky, expensive camera mic thing.
Chenell Basilio: Yeah. Yeah. Get like the Justin Moore backpack that lights up. Yeah. And you can have it say like, are [00:39:00] you a bootstrap founder? Come talk to me. Keep
Matt Gira: a T-shirt. Yeah, banner, yeah.
Chenell Basilio: Draws up like a banana or something.
Matt Gira: Yes.
Chenell Basilio: A quarter, you could dress up like a quarter.
Matt Gira: Oh, wow. Or
Chenell Basilio: have somebody else dress up, like a quarter you dress
Matt Gira: up on, like, I forget, I don't know, I don't even know if president's on the quarter, but like dress up as that person.
Dylan Redekop: I'm Canadian, so I have no idea what president's on the quarter. Yeah, I know there's a moose on our quarter or an elk. Geez.
I'm gonna get canceled by Canadians. There's an elk on our quarter. That's it. We're
Chenell Basilio: gonna get canceled by Americans. We don't even know what's on quarter. This is your brand now you have noose on the quarter.
Dylan Redekop: I should. I'll look that up when get Amazing. Any parting thoughts or words like, I think anybody listening might be like, well, I don't even have 1200 subscribers, or, um.
And I'm, I'm struggling. Like, do you have any words of advice? You might feel like I only have 1200 subscribers, but there was a play a point in time 11 months ago where you had zero. Yeah. Um, what's the, like Matt's word of wisdom for the day? I.
Matt Gira: I feel like everything I've learned is just like stick with it.
[00:40:00] And like is if you feel like you're providing value for people that it's gonna hit eventually. Yeah. It hits faster than other, like for others, like everyone's on a different timeline. Mm-hmm. It's like, in my head it's been like, it's hard to do it, like compete against yourself versus like someone else.
Yeah. And which is hard. It's also hard, like especially doing these deep dives, I'm like, oh, they grew so fast. Or like, but then you'll hear people be like, oh yeah, it took seven years, whatever it is. Like mm-hmm. So it just like do good stuff and I think consistently growing that mentality, I think that's where it matters.
Dylan Redekop: Your story kind of reminds me of that, um, Jack Butcher diagram where it's like, you know, oh yeah. Small line, small line, small line, small line, and then all of a sudden, boom. And it says like,
Chenell Basilio: this is pointless at the bottom. Exactly. If you think it's like
Dylan Redekop: you give up
Chenell Basilio: right before you give. Yeah. Right before you give up.
It's like nothing's happening and then all of a sudden it's like explosion.
Dylan Redekop: Mm-hmm. Mm-hmm. And there you can feel when there's like a little bit of momentum building, but when you're getting the signal, I guess, that like crickets, nobody's watching or listening, then maybe [00:41:00] it's time. You don't wanna do the same thing over and over, um, for years.
But my point is like you're getting a bit of momentum and you're getting that. Growth. Maybe not as fast as you want, but I mean, we see the quality of content you're putting out there and work you do. So I think it's just a matter of time. If you stick with it, appreciate
Chenell Basilio: that. And I think you have the experience, the knowledge, and like
Dylan Redekop: Yeah,
Chenell Basilio: it's going to happen.
Yeah. It's inevitable. It's just like patience.
Matt Gira: Yeah. It's just hard. I know
Chenell Basilio: where,
Matt Gira: yeah. But I think, yeah, totally. I think, right. And then like the in person elements, like when I go to events and like people are like, oh yeah, I read X, Y, Z thing, and like, this is really helpful. I'm like. I had no idea you're even on the newsletter.
Mm-hmm. So it's those like signals that I'm like, that's the more important piece to me right now. Yep. Yeah. Like the one deep dive has like 34 views on YouTube or something, and I'm like. Darn it. Like that is such a good video.
Dylan Redekop: Yeah.
Matt Gira: But then like before, a wa like the 34, I guess 34 people still,
Dylan Redekop: so. Yeah. It is.
It is. So people can find you on LinkedIn, Matt Jira.
Matt Gira: Yeah. Um, yeah, find me there. And the [00:42:00] bootstrap report is join the quarter.com/bootstrapped.
Dylan Redekop: We'll put all those links all down below where you're watching this. And man, it is so great meeting you in person. Yeah, for real. You have legs. Yeah, you have legs.
That's right. You're not just the head. You're just the head. Uh, thanks for hanging out with us. Yeah, yeah. Thanks Matt. Thanks for having me. This is always fun.
Chenell Basilio: Awesome.