Bootstrapped Web

Hello, everybody. Welcome back to another episode of Bootstrap Web. Mr. Brian Castle. Good to be with you.

Good to be with you, Jordan. Yeah, we're back.

We're back. It's Friday. That's nice. I'm sore because I started playing in an old man lacrosse league.

Oh, wow. That's intense lacrosse.

It's a bit intense. You know, my oldest daughter inspired me. She's nine years old. I started going to her practices and coaching her team a little bit when necessary. And then I started, you know, I played all growing up and I

played was gonna ask that was your sport growing up? Yes,

that was my sport and then Very East

Coast thing.

Very East Coast Long Island thing. And I played it into my thirties and then at some point I stopped. And when I moved to Portland, never found a league and just haven't done it since I moved here. And then all of a sudden I took her to the lacrosse store, started talking to the owner and then he gave me the info for like old man, 35 and older league.

Very cool. So I just played second game a

few nights ago and I'm, I forgot about being hit with metal sticks. So I'm sore.

Like pads and everything? Like gear and everything? Oh

yeah. Yeah. So there's no, there's no like, it's the perfect level of intensity. No one's going easy and it's full contact, but no one's, no one's putting their shoulder down and hitting someone because that's ridiculous. You're going to

go to

work the next day. Come on. But I did get hit right in the belly button, which is a very strange feeling. And you just kind of heard me in the middle of the field like, involuntary.

I never picked up lacrosse. I was, I was a baseball and basketball guy and I always sort of regretted like not sticking with one of those and into being an adult. I miss I miss playing team sports.

Yes, me too. I missed it. Yeah. That was fun. How about you?

What do got going on?

Tomorrow my wife and I are going to the city going to New York City for our little date overnight thing for our ten year anniversary.

So And well, first of all. Very nice. And are you going to eat in a restaurant without a mask on? Is that right? That is Amazing.

It's amazing. I went to a party last night. How about that? Like, just a graduation. Not a graduation.

End of year thing for like our third grader. The kids were together and then there were like fifteen, twenty adults just standing around talking with no masks on for a few hours having a few drinks. It was like euphoric, man. It was a trip.

It's unreal. Yesterday I had a haircut. I've been having haircuts all year but this is the first time like my barber and his shop there, no more masks, we're done with that. We're good.

Yep, vaccinated and move on.

Just bought some tickets for a Mets game in a couple weeks like Nice. Back to feels great.

It feels great. I'm looking for any excuse to travel for work. Like just tell me you want to have a meeting or a dinner and I am on a plane. Let's do it. Good.

Well enjoy the weekend. That sounds great.

Before we get too deep in it, wanted to do a plug, a shameless use our podcast here because I'm trying to find two people, especially one person to hire.

Okay. Let's talk about it.

Actually, this follows on what I was talking about, I think in the last episode. You know, I'm trying to build this, it's a software company around zip message, but I'm thinking about it much more like building a media company, a media brand, thinking about doing a lot of podcast content and video content and, and some creative ideas like new ways to build audiences essentially around a brand supported by selling a software product, Zip Message being that.

So we got great feedback on that conversation.

Yeah, I've been getting a lot of good feedback. And so, know, I'm the product person in this in this team. And I'm trying to build out the other key members of this team to run the media side of that business. And so the two roles, I wrote up a couple job descriptions. I don't have the link to say here because it's like a notion doc, but I will put the links in the show notes for this episode.

The first and most important position I think is, is the media creator, role. And so this is a person who I'm, I've been talking to a couple people but it is a really difficult one to find potential candidates. So I'm looking for somebody to essentially like co host podcasts, be a show runner for new podcasts, video content, produce videos. So somebody who is like a great storyteller and has the technical chops like the video production podcast chops, you know, doing interviews with other people, coming up with creative, premises for a new show and just you know, being like just driving the creative content that comes out of this, this small team. And then the other person will, this hire will probably follow on right after the first one is what I'm calling a technical marketer.

And so that person will be focused on distribution and optimizing all the channels for distributing content, but also optimizing the SaaS funnels, you know, getting, getting into the trials and metrics and, and, and, you know, doing all the little things to execute, focusing on analytics, conversion rate optimization, doing some outreach, doing some, you know, distribution kind of stuff, social media, email marketing. Like I said in the last episode, to execute this plan, it needs to be like a two person strategy, like a like a creative lead and a distribution lead and have them working together and I'll be in the mix with that stuff Let as

me look at this from a slightly different point of view, right? Because I'm in moving in the same direction as you are. I think you did a great job on the job listing. I stole it, shared it internally. We're going to abuse the hell out of it.

Thank you very much. Please do. But it feels like what you're really what you're saying is that there needs to be a function that creates an audience and does that by understanding what the audience wants and providing value to it and then the media that supports it and delivers that value.

And then I would say yes and coming up with creative new ideas like a new new premise, not just find a 100 founders to go interview every week, like new angles, new new premise.

Yeah, I noticed that you emphasize that in the job listing where it was like, we don't want to do the same stuff. We want to really think about why we would do something and then, and then look at the format that way, not just, well, let's just do it on the podcast because that's what everyone does.

Yeah. Like what, like how many times have, I'm sure many of us have mentioned, talked about the show song exploder. It's a cool premise for a show. You know, they take one song, they explode it, they break it apart. How was it made?

What was the story behind this song? You know, it's a unique concept for a podcast. It's different. Yes. And it's really well produced and it reaches a huge audience because we're talking about popular music, right?

Yes. Yeah, dissect. So like that's, that's an example of a really powerful premise for a brand new show. And then that show went on to become a Netflix series like, you know.

Okay, cool. So I got it. A unique take on the media. Cole Kuchner does a podcast called dissect where they do that for an album. So he'll look at Kendrick Lamar's like latest entire album song and every episode is a song and it breaks down that song.

It's just unbelievably educational, entertaining. Okay, cool. So first step audience. And now this technical marketer role is really the transition between the audience and the product. It's like the bridge on identifying some people in the audience are going to be interested in what we're doing as a product, not everyone.

And you're not building the audience solely for the purpose, like, because that people see through that. You want the authentic version of media and an audience and value, and then allowing for a bridge from there over to the product.

Yeah. And it's about thinking about that target audience and distribution before we even create the content. So if the technical marketer and myself are in the mix on coming up with ideas in collaboration with our media creator, It's about we know that at the end of the day we wanna reach this segment of people. So how can we start to come up with creative ideas for a show with an awesome premise for that audience would just eat up every single day. And the technical marketer can think about as we're ideating on this stuff.

Okay, if we're going after that audience, these are the types of channels that we can go to distribute that show and grow the audience for it if if if we were to go down that path and even produce that show.

Here's what a funnel looks like

for Here's what a funnel looks like. Like think about it end to end before we even create it. And then actually do the execution. Like I'm focused on product. I can't do the mechanics of that every day, but I want it to happen, you know?

That's what I was getting to is that it's interesting that you sit in the third part, right? You're the product. It's like audience and then the bridge over and then the product has to satisfy what people are looking for and understand why they're looking for it and deliver the value from a software point of view on an ongoing basis. I'm going to argue that there's a third function, a third role that we're going to bump up against immediately and that is of community. Because it is a really tall task to ask someone to lead the media creation efforts and also focus on community.

Some people are magically talented and do that almost inherently. They just can't even help it. They just create media and form an audience around it and communicate with that community at the same time. And it can be the same person for a certain amount of time, but they are like, there's a third element there around community and fostering it and kind of communicating

with it. For that community piece, I think my thinking has changed a little bit. You go back like about a year ago, I was talking about that. Like if we could build a community around our product, like this community driven marketing idea, I was really excited about that. And I tried to execute that with process kit.

That's right. I remember you had, was it a Slack group?

Yes, Slack group. And we did a little bit like we started to dabble in like doing like AMAs to try to get community engaged in a Slack group. My thinking on that is now if you want like an engaged community who is interacting with each other, the audience has to come first.

The audience is the raw material in some ways that allows for

it Yeah. To And and like for a brand new community, like if you wanna start a Slack group or or or a circle or or whatever you're gonna use for your community, it's just such an insanely difficult boulder to push up a hill if you don't have an audience to begin with or if your audience is very small. Because the truth of the matter is for every 100 people who follow you, only five of them or less are the type of people who will actually leave a comment in the community. The other 95 might lurk, they might watch, but they're just not commenters. That's just the nature.

So you need thousands and thousands of followers to just spark a community, you know? I mean, that could happen after a year or after two years of, of, of growing a really strong audience. Like then, then it starts to be like everybody listens to this, to the podcast. So they're like, they're very much like each other. So let's just put them together.

Let's invite them to a conference.

That's right.

Do stuff like that.

But like it's, it's come for the content, stay for the community.

And in terms of building the early team and the end where to invest the resources. I think that too early on trying to create a community out of a very small audience, you're gonna waste resources. You're gonna waste like people or waste hours, waste money on a extremely difficult uphill battle where now my thinking is like invest that stuff into audience growth and obviously optimizing all the things that you need to do from an SEO standpoint and a funnel standpoint on your product site. Like there's a lot of, lot lot of just mechanics that need to happen from a marketing perspective. So you don't want to like waste these cycles on trying to get people to talk to each other in a Slack group.

If, unless they're just like banging down the doors like, hey, there's a lot of us we need to.

Yes, if you don't create it, we're going to create it off on our own. I think of what's that podcast called with Sean Parr? It's like my first million.

Yeah, I started listening to that recently.

Right that that was come for the content state for the community. It reminds me of Ian Carr. I'm not sure if I'm pronouncing his name properly, but he writes Fintech Today, which was a newsletter that so that was the content, and that generated an audience, and then that turned into a community, and then that turned into like a syndicate fund. And now it's like, it's like a whole, it's all community. It's its own like little universe.

Okay. So it makes sense. So now you have these two roles open and anyone listening who finds that interesting, I have that role open but it's not a published job ad. I'm just having quiet conversations on the side. Yes.

I wanna talk about that. There's just one more note on this, you know, because especially for that media creator role, it's a really difficult I am talking to a couple of people, but I think what I'm also starting to look at, I don't even know how viable this is, is to sort of be like a scout and try to find people who have like a small, like a young podcast or YouTube channel or both sort of in the space and maybe look to acquire them and that show and and enroll with that you know. But like how do you find someone who hasn't blown up yet you know.

This is it. This is what we talked But about last you can

see the talent like on the page and it's And thinking about that

this is kind of an opportunity for someone listening or someone that they're familiar with to just raise your hand and basically say, well, I'm talented. I just need a chance. I just need some budget. I need a bigger stage to perform on.

That's what I really feel. The top here.

Yeah, cool.

What's the role that you're looking at?

It's a very similar role. It is to create audience around the content that we think our eventual community would be attracted to. There's a few different angles on it, but I'm taking like you a media angle. Sometimes I think about it as news. I think about it as reporting.

Yeah. I think of other

things that I

have It on my mind really it really feels like, you know, when I try to think about decision makers, founders, marketing teams in these direct to consumer brands. And I think about our real our real targets, right? The people that we really love to work with are these just very cool direct to consumer brands are forward thinking. They're growing. They they're not clicking on ads.

They're just, they're just, it's just not happening that way. And so what they do is they talk to their peers and that is the most important channel. And then you start to think about it. Okay, what are they actually reading and what are they actually looking at? What are they actually talking about?

And to me, I can't help but I keep going back to news. Like what's happening in your industry? Who's doing what? Who's collaborating with who? Who raised money?

Who hired who? Who left this? Who's starting something new? Like that's the stuff you talk about on a day to day basis. And I think there's an opportunity to create media around that, that turns that media brand into a destination and somewhere that people look to regularly.

And that would be, that would be power.

That's like one of a handful of like new show ideas that I would love to see happen someday, whether it's from us or from someone else. Like for sort of our space, like a weekly news show of like, like one idea is like get get all the podcasts and I pick out the highlights from from all the current podcasts out there.

Yeah. Like what's happening in remote work today.

Yeah. And like what like or this company just shipped this feature or this this acquisition just happened and like just a roundup of, of the current week's news, without having to keep tabs on everything, you know, most mornings I listened to Axios today. Axios is the big news site and it's like a ten minutes, ten minute podcast, a daily podcast of just like basically three big stories, you know?

Yeah, I do it subconsciously. I get into the kitchen, I go, Alexa, what's the news? Yeah. You know, and that's it.

And it's like the morning brew newsletter. It's like that, like the idea of like, get, get like the quick hits, you know?

Yeah. And there's some aggregation there and I respect the hell out of people who go long form and original thought and original ideas. But the way I find them is I consume the newsletters that aggregate those. And so I read LeanLux and I read web, you know, web's email at 2PM. And that's how I get my e commerce news.

And that's what I actually digest and read. So my thinking is like, if we could effectively sponsor that, that is the right way to go as opposed to writing blog posts and content about ourselves. And you know, that'll happen anyway when we like release features and stuff.

Our friend Matt Wensing, reached, I think he sent us both a message, with this link to an out of beta episode from back in 2021 when he spoke to the founder of Freightwaves, which nobody in our industry would know, but, but apparently they're a pretty big deal in the logistics and shipping industry. Right? This is a fascinating episode. I tweeted the other day. It was a great interview.

This guy, Craig Fuller, who basically built a media brand in the logistics space to sell their SaaS. And they made the connection of like, it's, it's the Bloomberg model, right? You know, like Bloomberg built this huge media empire, but they sell the what is it? The Bloomberg terminal. Right?

Like he talked about themselves as like the Bloomberg of of logistics. Right? Like they they have this huge like media arm, hired a bunch of journalists and everything and they sell a SaaS product, you know.

Yes. Yes. But they earned the attention of all the money. Everybody with the money.

And so speaking of Axios, we're just going on tangents here.

Yeah, whatever man.

Speaking of Axios, I don't know if anyone knows or how successful this is, but I keep seeing in the, in their, on their website and in the feed, they're promoting their own software product now. Like Axios came out with this, it's some sort of like writing tool, like a tool to, I think to like write like Axios articles are written, which are like very bullet point, like brief articles. I forgot the name of it, but they have some technology around how they structure written articles with some AI involved and making it brief and and succinct and and they're and they're trying to sell a software product out of that. So it's just this this merger of media brand and software, there's this is a direction that things are happening.

Yes. Best way to get attention, best way to monetize with the best multiple. Yeah. And Axios was recently acquired by some faceless gigantic company called IFS. And so I wouldn't be surprised if they're offering software potentially owned by another company that IFS owns.

And they're just, they literally bought audience, right? This is the same thing that we talked about with Barstool Sports, where is it DraftKings? Right? The gambling site? They just bought the exact audience that gambles.

It's very natural alignment.

Yep. Yep.

Cool, man. Well, I have a feeling we're gonna we're gonna talk a lot more about this and we're gonna pretend not to be fighting over people for the same role. Right. But we we are.

Yeah. So, yeah. What what else you got going on?

What else? You know, I have had this feeling recently. I do a lot of calls and I learn a lot from it and I kind of welcome it and not every call leads to a potential customer, but it always leads to some type of a learning. And the feeling I've had recently is basically at the end of the call, my hope is that I have planted a seed that like the legend of Rally grows. Like that's what I want.

Every conversation, I want to make sure I communicate the gospel, what we believe and why and what we're all about. And where I see it successful is when at the end of the conversation, it's really like a, it was great talking with you. Doesn't sound like it's going to make sense for us to be a customer in the short term, but I'm really glad that there's a company out there doing what you're doing. It's almost like I'm just spreading the gospel one conversation at a time. And then what that's really getting to is one on one, one on one, one on one, And then we can take that same message and start to go one to many.

And it's almost like I'm testing the messaging. When we go hire the media creator, a lot of the strategy around what to say and who to say it to and why that will be attractive to them is because on these calls, I'm digging into something that's one layer below the surface. Like, let me be a little more straightforward with it. Not everybody loves Shopify. And publicly, you don't see that because on Twitter, it's a lot of love fest and they're a darling and all this other stuff.

But under the surface in these private calls, there's a lot of dissatisfaction.

In like the technology and like the limitations or what is it?

A combination of the technology and the approach that it's being distributed in or even know how to say that. But basically, it's a combination of this feature isn't available and it's not in our interests to give you this feature so you can't have it. So that combination of like, this is just what happens with big platforms. People start to get sour on being told what they can and can't do. And so when I talk to both other app developers and merchants, I start to understand what the right messaging is for us.

Not to like point at Shopify and say that's the enemy, but to articulate what these people are feeling and their frustrations and looking for alternatives. Our whole thesis is that these big platforms are not right for everybody. They're right for a lot, especially for the lower end of the smaller end of the market. But these merchants who know what they're doing and don't want to be told what they can and can't do with the product, they're the ones that are going to start to look toward the headless ecosystem as something that gives them more freedom. And our checkout makes moving to the headless ecosystem easier.

So these calls and like the gospel and getting the feedback is what's going to inform our content and our media and our point of view.

It it's such a difficult and really important thing to figure out that tagline. Right? Or or the the the thing that you lead with when you talk about rally or zip message or whatever the

Or what you're known for that that

Yeah. Like when when you're introducing it to someone whether you're on a call or whether you're writing the when you're writing the tagline, when you're posting it somewhere else where where people might see it for the very first time.

Right. The impression you want everyone to have. Yeah. How do you how

do you like succinctly describe what it is, make it attractive, make it intriguing enough that they wanna learn more and resonate with the thing that they're probably have been secretly searching for? Like how do you how do you wrap that up into like a a one liner that invites them to wanna hear 10 more lines about it?

And and I was reading a tweet by April Dunfield. Where's her book? I have it right here. Dunford. And someone was asking her a question about how do you position when you have multiple products?

And what she was saying was, well, look, multiple products is complicated, but when you have one product, is a lot simpler than having multiple products, but you still want to position both the company and the product with the same positioning. That's what we're saying right now. We're talking about a separation between the product and the company, the product and like what people interact with in the content and the media and that positioning. So you ideally want them to be with the same positioning. So if you look at something like Basecamp, it was almost like their content had better positioning than their product did.

It did, the audience was so massive and the affinity was so great that it did lead into a ton in the product. There was alignment in terms of, you know, this product enables you to be remote and enables you to work in this better way and calmer way and so on. Made sense. So we think about that also where our product gives you freedom, right? It gives you the ability to decide whatever you want to use on the front end, you can, whatever you want to use in the back end, you can.

And so how do we make sure that that stays in alignment with our company stands for freedom? Our company stands for the merchant being right and let them decide what their Yes, stack looks and then our content can kind of be from that same angle. So if you see us coming up with content around platform stuff, even if it isn't in e commerce, but it's people doing things that give people more freedom that that will still be in the same positioning realm for us.

Unlike the media stuff, it just needs to be like it needs to stand alone as if we're just building, we're trying to reach a large audience and that audience is likely to contain lots of potential customers or that audience will will talk about it. Like, I would see like Zip Message as just being the default sponsor on, on every show we produce. Right? The shows are not going to be about Zip Message or promotional of Zip Message except for the mid roll or whatever the presented by Zip Message, like whatever it's going to be, you know? Yeah.

I'm not there yet. I'm still I still want it under the umbrella. I still want it to be the rally podcast and the rally newsletter. And I'm not I'm not convinced yet that the separation in like different brands and different names and everything is necessary in order for the

I think for the rally brand, it sort of makes sense because rally, you could feel it in the name rally like that could that

could mean Right toward the freedom. Yeah. Angle.

That's why I like that name so much, know. Like in my case though, like, like Zip Message is very a product centric name for a product. So that's why to me it just makes sense to think more about like, let's just create awesome stuff and sort of merge it with the potential audience. Not to say like we're not gonna do the traditional SaaS marketing stuff for ZipMessage itself. That stuff is going to happen.

Again, that'll be part of what the technical marketers is, is, is working on. But what I found in B2B SaaS marketing in recent times is like the volume is just not the volume and the attention, the competition for attention for a brand new product. It's, you know,

It's a mountain to climb.

It's crazy. It's just an insane mountain to climb. And so if you can also build an audience that that's just a multiplier on all the, all the regular marketing stuff you're

going to do.

Yeah. It's under the surface, but a lot of it really matters a lot in terms of how you name it and where it lives and all that. And I go back to Basecamp, I think about signal versus noise.

But like when it comes to the product itself though, what you were talking about like when you're having conversations and I have the same thing too. I'm on calls about zip message or any of my previous products like it was just call after call after call honing in on how I explain the thing and which because there's always gonna be like three, four or five different key benefits or key reasons why people like the product but the difficult thing is figuring out what is the most important benefit that you want to lead with in that first sentence. And it's also like online, like if I'm going to mention this thing in a post that I make to a forum somewhere where people scrolling through my like, and I'm the founder of Zip Message. It's a tool for asynchronous. So I'm actually working through this question right now, right?

Like I tend to go with it's for asynchronous video conversations. Sometimes they say asynchronous conversations with your customers or your colleagues. Like I know I want to get a sync in there. I know I want conversations in there because I

was going to say just use those two. It's very synchronous conversations.

Yeah. And this is what I struggle with because like Slack is for asynchronous conversations too, but we're not Slack. And then there's the other big differentiator that's like you can just share the link and it's zero friction for your customer to reply on video. So it's like how do you work in all these different benefits and you can't work all of them in so you so which one do you lead with? Right?

Yep. Yeah.

It's a tough process to go through. Yeah. Sometimes someone just asks me, can you send me a quick blurb on what you're doing and I'll forward it on? I'm like, I I'll try. Yeah.

Getting it down to a sentence as opposed to a paragraph.

Yeah. Tricky.

Cool. Well, I don't actually have that much more time. I gotta keep it short today.

Alright.

You have anything else you wanna cover for a few minutes? I I do not on my side, so feel free.

Yeah. Well, so just the only thing that I'm working on, I mean, it's been, it's been pretty cool with ZipMessage having a, the customers are growing like the numbers are growing every week and it's kind of fun. You know, I still have that, that mindset of skepticism about everything because they are converting fast and easy and I'm not used to that and I'm skeptical of it.

All right. Let's, let's see what really happens in a month.

And it's just like, it's because the tool is simple. It's just easy to adopt. And that was the whole reason I went into Zip Message is because it's easy to adopt. But that's actually the case and people are converting without ever speaking to me, without any pre sales questions.

It's too good to be true after, after doing a lot of work for conversions.

And so my next order of business here that I really need to get going in the next, I'd say thirty days is trials are not open for everyone. Like, I'm just sending invites every week. So there's still that limitation at the top of the funnel and, and people are converting through that, through this very tight, tightly held funnel. I don't feel ready to open it up. I have more invites to send, but more importantly, there are two things that are really missing.

We have absolutely no onboarding whatsoever. It's just brand new users. We're converting really well and there's plenty of people who probably would have converted if they weren't completely confused.

Right. So people are figuring out on their own.

You know, there's still bugs, in certain versions of certain browsers that make a really bad experience. So we we gotta get that stuff smoothed out before I, before I open up, the bucket. And so, yeah, hopefully in the next like two to four weeks between all this hiring stuff and everything else that I've got going on, I'm I'm trying to stay heads down on getting the product shaped up and top shape to be able to open the door to trials. Not going, not doing like a product hunt launch yet or anything like that, but just start start to have like a real trial funnel going because right now it's like I'm I'm just inviting.

Cool. That sounds good. So far so good.

Hey man. Cool.

Good stuff. Thanks for listening everybody. Friday. Enjoy your weekend.

Later folks. See you.