Bootstrapped Web

Hey. It's Bootstrapped Web. We are back. Jordan, how's going, buddy?

Doing pretty well. Brian, good to see you. It's Friday.

Yep.

Excited for the weekend. A little tired. I went out last night, going out tonight, two nights in a row. That hasn't happened since, like, 2019.

Oh. I think I'm I'm at the age where I'm learning that my body is just not built for running outside. I've I've been trying to build a running habit. I've been, you know, walking and biking and stuff for for a long time, but I wanna kinda kick it up a notch. And I started spending the last two or three weeks running and my legs are in so much pain like all the time.

I don't know very much about running, but could it be a technique thing or a shoe thing?

I thought it was. I've read up on that and I have changed the technique and that's helped the shin splints, but then now it's hurting on the other side of the leg and then my knee is rusty and all this different crap. It's like, I don't know.

Well, at least you're trying. I admire you for that. That's not a topic I want to get into. Let's talk about business.

Exactly. Exactly. How's it going? I think you've got some announcements to make. So let's get into that.

I do. I do. And it's, maybe somewhat anticlimactic for for listeners of this podcast. But by the time this episode goes live, we will have made our formal seed round funding announcement. We are doing some press and hopefully we get some good coverage on Tuesday, the twenty sixth.

And that'll be our announcement that we've been talking about on this podcast for a few weeks now around how we're using that announcement as strategically as possible. So,

yeah. So what can you share that's like kind of new new info for folks?

Yeah. Yeah. I want to kind of get into more details and some process stuff and so on. So we raised 5,800,000.0 in seed funding from several VC funds and a bunch of angels. The majority of the money came in a while ago, but we've kind of held on to the news as we've talked about here in this podcast to basically make the most use of it.

So we raised the money, hired the team, built the product, and now that the product is ready, we're using the funding announcement to drive interest in the product. So that's what we're doing. I thought it made more sense to hold off until the product was ready to take on customers instead of announcing three months ago and then just generating some interest. I wanted that interest to turn into actual customers. We're announcing it at a time when we can take on customers.

And the goal is to drive interest from prospects, from like partners to integrate with some investor interest and just general market interest.

Nice. So you're kind of like closing that window between this big announcement and like actually taking on customers. Whereas yeah, like, like most startups kind of announced the big funding, like very early on, and then it's months or a year before something is even ready to show.

Right. That is given the nature of our product where it takes a while to build a reliable checkout. I didn't see much benefit in announcing it just to announce it. So I want to announce it with some strategic kind of intent behind it. It's been it's been a fun process.

The PR thing is my first time doing anything on that front.

Well, before we get even into the announcement, I'm I'm kind of curious, like bigger picture going back further. You know, you were in Cardhook that started out bootstrapped and then into into some funding, but not not this level of of funding. Right?

Yes. Yeah. At Cardiff, we we never had more than, like, 250 k in the bank until until it really took off and got profitable.

And so as you were heading into Rally, like, planning it in the in the earliest days, like, in your mind, were you always headed toward this path of like definitely gonna raise a lot of money, grow a big team very fast and and really, really do this thing? Like that was the path. Yeah.

Yes. Yes. The the the path was always to acknowledge the size of the opportunity in ecommerce. One of the things we did at Cardhook was we proved like, checkout was not thought of as a category. It's still barely thought of as a category.

There are, like, a handful of competitors. Like, it's not like a big thing. And that's because the assumption is that when you choose an e commerce platform, you then accept the checkout provided by it. So at Cardhook, of the things that we proved was there's actually demand for a specialized checkout product. And people on a platform, even like Shopify that has a great checkout will still switch if you give them the right set of features and benefits.

And so the way we think about it sometimes is at Cardhook, we were playing D1 ball. Shopify's checkout is good and the shop pay buying experience is excellent. So to compete with that was really difficult. In the rest of the e commerce world where we live now with Rally, the checkouts aren't as good. So we're kind of taking what we're used to in playing up a few levels and bring it to the rest of the market where the, you know, the WooCommerce checkout is not even close to Shopify.

BigCommerce is better, but still not close. Salesforce, a lot of these. So to me, that sounded like an opportunity that we need to go as fast and big as possible to capture as much of it as possible because Cardhook created a lot of competitors. People took our product at Cardhook and brought it over to WooCommerce and like cloned it and copied it. And there's a lot of that.

I didn't want to even compete at that level. I just wanted to come right over the top and use the credibility and experience from Cardhook. Look, I just found myself, you know, I never expected to be in that position, but coming out of the Cardhook experience, it was, it was more complicated than just raising my hand and asking for money, but it wasn't that much more complicated than that. And so given where VC was given where valuations were, how much money people were raising, I was like, that's, that's the way to do it. That that's what makes sense.

I think about all the different new business ideas that I had over the years. The the steps of like validation, looking at the market, maybe designing a prototype, talking to some some early prospects for customers. In your case, like where did the mechanics of starting to raise and talk to people fit into like the earliest days? Like who, who did you talk to first in terms of like, Hey, I'm starting something new and, you know, raising funding.

So once I made the decision that I should move beyond Cardhook and leave that in someone else's hands and raised Emily up to CEO and I knew, okay, was going to start this new thing. What I did was I had relationships with a few VCs at Cardhook and we got to know each other, but it never really made sense to raise VC for Cardhook. So it was just like we got to know each other and we liked each other. I'm talking about a fund in LA called Rainfall. So I got to know Ron and Kyle over there and we just liked each other and hit it off.

And then when it came time to start Rally, I talked with them about it and I told them my plans and my thinking. And they did something that was really smart for them and really helpful for us. And that was as soon as I told them that I was going out to raise and I was going to put a process together and meet with a bunch of people and so on, They just made an offer. They just said, sounds great. We'll lead it.

And what that did is a few things. It got them involved. It got them involved in a way where they didn't need to compete. It wasn't like, well, that's great that you want to lead, but so do they. So can you beat them?

It removed that entirely. So they got this pole position in the round.

You know, we hear this a lot. Like I know there's probably a lot of, you know, listeners who what does it mean for a fund to lead around? And is that something that generally most funds prefer to do? Or are there cases where they want to be involved, but not not leading? Like, is there a competition to be first to to claim that leading spot and and what do they actually do as the leader?

Like, can you get into that?

It it is really important. And so it depends on the fund. Some funds lead and some don't. And the hardest thing to do is to find a lead. And so what the lead does is they set the terms.

And that's that's huge because if you have a large commitment according to a set of terms, it's much more difficult for someone else to come in and change those terms. So it becomes instead of this open ended negotiation, it becomes a yes or no. I take it or leave it. Here's the deal. Here's the valuation.

Here's how much we're raising. We already have a lead. Do you want in or not? So it kind of sets those terms. And then you're really looking to them in a slightly different way from the other investors.

The other investors are involved. Your lead is who you come crying to. And they say, We hear you, we'll help you. Here's what we need to do. Here's how we can do.

Here's how we can introduce you to.

So And do they also help with bringing in other investors?

That's right. That's right. So they help with the intros, they help with other investors, they introduce you to portfolio companies that might be customers of yours. So they're really taking the lead in terms of money, in terms of terms and in terms of responsibility in the round and really for forever, for the future. Like you get you get married up.

It was an interesting like strategic question on whether or not to bring in series A funds. So what's happened in venture is funds are starting to stretch across stages instead of being just seed and just a and just growth. They're starting to stretch all over the place because they want access. And so series A funds very often now either have started seed funds or seed initiatives, or they're just willing to come in and be involved in seed rounds. There's pluses and minuses there, right?

If you get a series A focused fund that comes into your seed round, the upside of that is they could do the A. So you might just be all set up with your series A. The problem with that is if things don't go well for you and they're not as good as you wanted them to be and the Series A fund is focused on Series A, they're not really helping you that much at the seed stage. And then if you don't get what you need to get to Here's a fund that led your seed round doesn't invest in the A. Now you've a problem.

Now you're sending, you're sending up bad signals because the, the A fund got a look at everything and decided not to invest. So there's all these like strategic considerations. So what we did is we only worked with seed funds on purpose because I wanted everyone to be focused on success at the seed stage and then all of them to be interested in making introductions and positioning us properly for series A because they win when we get to series a also because then they get the markup evaluation.

How about like finding the right funds and people in terms of the space that you're in or the direction that you're going aside from bringing in the funds? Like any strategic considerations?

Yes. Huge. All of it kind of mattered. And to me, the lead, the most important thing was the lead I had this amazing relationship with and I trusted. So rainfall, I had that.

We like I mean, these guys like WhatsApp and text me and just like, Jordan, you're the man. Don't forget. Like seriously, randomly on a Saturday at four p. M. That's the tech kind of text I'll get.

And it's like it just feels like you have someone supporting you and like has your back. It feels great. That the lead, that was like the most important thing for me, the relationship. And then we tried to round things out in the best way possible. So we brought in commerce ventures and they're like have big relationships with really big companies and enterprises.

And they introduced us to visa and they like know that world that's kind of hard to get into. And they usually invest in later rounds, but they wanted to get involved in our seed. And I saw the opportunity and the benefit there. And I work with Matt over there. So they're great.

And they also have this entryway into a world that I just like can't get into without them. And then we also work with Long Journey Ventures. And that's like Scott Bannister, who was early in PayPal and Lee Jacobs. And so they're dialed into this alternative San Francisco scene, not the main scene, but almost the Peter Thiel PayPal type scene. And I just am drawn to that ideologically also.

So I liked that and we hit it off. Then we work with four ventures and they're as ambitious as any founder. And I like love that. It's like two guys on a metros who we work with and they want to prove themselves. They're as hungry as any founder.

And I was like, these guys going to break through walls for us. And they're in San Francisco and dialed into absolutely everybody. So they're like the entryway into SF. There's a few others. And then what happened to us?

Commerce, long journey, a four and rainfall. Yes. And then what happened was we finished the seed round. We thought we finished the seed round. And then I got a DM on LinkedIn and someone named JP from Felix Capital just DMs me and is like, I love what you're doing.

Can we talk? And normally I would be like, yo, we're done. I don't want to talk to anyone anymore, but something about it kind of hit the right way and we started to talk and then we got into like a relationship.

I hope I don't have any of those DMs in my LinkedIn because I haven't checked it in like ten years.

Yes. Every once in a while I check those DMs. So Felix Capital is more of a series A fund in Europe, but we just hit their like thesis, like right in the bullseye, like fintech, Web three commerce headless. Like they were looking at all of it and we were right in the center of it. And JP and I built up this really trusting relationship and they said, all right, let's just, let's find a way to get involved.

And so then they came in at the end to bring it up to the 5.8 total.

Very cool. So all of that, all of that action, all of that, that closed months ago, right? Yes. Yes. That window of the process and talking to people and closing it, like how long did that kind of last?

And I'm also kind of curious like how that played in with the work of starting to build and hire and all that.

Yes. The initial funding was really important to, you know, create the entity, hire the people, get the health plan in place, all the mechanical stuff that happened right away. And then we used a safe for all the investments, which I had never done before. I had always done convertible notes because we've talked about this before. We did all convertible notes in Cardhook because we always told the people very straightforwardly, we may never raise again.

And if we never raise again and there isn't some type of a fundraising event, then your intention is to buy stock in the company, not to have a note and lend us money. And so let's just convert it to eighteen months. So if we don't raise money and we don't hit that qualified financings like threshold, then you still actually get which is what is the point of this interaction that you get stock in the company. So all of our stuff at Cardoc was convertible notes that automatically converted at eighteen months maturity. And this is different.

This is everyone's aimed towards series A. So we did safes, which, which made more sense.

Yeah. Yeah. I was looking at that too when I started, when I was talking to, you know, potential angel investors for Zip Message and that that's what ended up, you know, not that I would definitely rule out future funding rounds, but I felt like, especially if I took on like several safes with individual, I would feel like the path is supposed to lead to venture, you know?

That's right. Because otherwise you're just gonna have these safes hanging out for years, which is not good, not good for anybody.

Yeah. Not good. And and it's like, you know, for for it to really be a a fantastic return for them, you know, you you kinda have to be the exception. And it's, can't really bank on that. Okay.

So like fast forward to to to now, like like now you're rolling out this announcement, right? So what's what's all happening in that? You've you've got like like a big announcement on the website. You're working with PR people. How's that working?

Yeah. It's been an interesting process. We hired a PR freelancer and her job was

to

get attention for the funding announcement. And then we're going to continue working with her beyond that for podcasts and media appearances. So it has been like a demystifying process because before this, I would always look at, you know, these tech crunch articles about this funding. I'm like, I have no idea how they

do Right. That

My assumption is like, you know, the VCs know the media people and then send an email and they're like, Hey, our new company is getting funded. Can you write about it? I didn't know anything about the process. This has been clarifying where it's pretty straightforward and anyone listening can do PR. You just have to email journalists and say, here's what we're doing.

Here's a draft of the press release that we're going to send out later so it has all the information that you need. And then there's the format for what a press release should look and sound like, especially on something so typical as a funding announcement. And then you have to find an angle on what makes it interesting, but anyone can do it. We just happened to hire a PR person that has done it before. So she was like, alright, now you need this and then this and write this and we'll finalize the draft and then we'll send it out to people.

Does hiring a PR person also bring the benefit of like, she has contacts that like when she cold emails a journalist, they've spoken before. Right?

Yes. Yes. But only to a degree. Like you still need, you still need an angle and a story. And we had some difficulty because we're just announcing the fundraise.

Like that's run of the.

Yeah. You need something, something juicy, something, something really interesting and different.

You need a hot space. You need a story. You need an amazing client. You need something to go with it, whether it's an eye popping number or so we had to come up with our different angles. Since that happened, you know, every, I think I've done a handful now, but I'll just jump on a call with a journalist, which the first one was nerve wracking, man.

It was was nerve wracking.

Are these, like, pretty, like, major publications or, like, who who are you talking to?

Yeah. So we, you know, we we TechCrunch, we talked to on Monday, and hopefully they hopefully they cover it. It's funny. TechCrunch, like ignore and dismiss. But what if you want to do a funny announcement?

It's all about TechCrunch, obviously.

Did did it even happen if it was if it

was not on TechCrunch? Well, I hope they cover it. It's not a short thing. You know, publications like Business Insider and CNBC and and stuff like that. And you really like you wanna give a good interview and impress them and not come off like a jerk.

It's it's a new experience. It's not that dissimilar from jumping on someone's podcast and you're like, alright, I have to perform now. But it felt it felt scarier because Yeah. They could write they could write bad words about you. Yeah.

Yep.

You can answer the the questions as well as you can, but you never know how they're gonna end up spinning it to to make it click, you know, click baity and and get eyeballs and all that.

And I kind of had to go through that experience of like, okay, what happens if they write something basically a negative take on like an eye roll? Oh god. Another headless e commerce thing and thinks this, but blah, blah, blah. What if it comes out and it's bad? I have to just start being Okay with that, which feels strange, but that's Okay.

But ultimately, like this early on, like any press is good unless it's like really bad press. It's it's about making noise. Right?

Yes. Yes. That's it. So here we are. So by the time this goes up, we'll have our own blog post about it.

And then hopefully there's some decent press coverage on it and we'll use that as much as we can to get more traction. And then what I've seen people do successfully is they stack the news. So they'll bundle an announcement like, you know, for our series A eventually we won't just announce a fundraise. We'll announce the fundraise with this new feature set and this customer and a partnership with this. So it's like you're giving as much meat to the story as possible.

And I see the need for that now because the journalists are like, well, you know, what can I write about? No one cares that you raised $5,000,000. What they care about is like what you're doing and who's using it and who's involved and who your competitors are and that sort of thing. So it's definitely a different take on it.

Very cool. Very cool.

Yeah. And we'll see. And how about you? What's what's happening?

You know what I'm, I'm running into like, like just higher level, bigger picture. I'm still getting used to the idea of running this type of company and business and operation terms of like because I'm coming from audience ops and I've been hacking on SaaS products a couple of years now, now I'm fully full time focused on building Zip Message as a company. And I'm also at the stage in this first year where the product is the core of it is very well built. We've already passed all the bug fixes, not all the bug fixes, but a lot, like we just don't see bug reports.

Right, the preliminary.

You know, nearly as much as we used to. Also, the feature requests are actually like fewer and fewer and far between. Like there are definitely some and we have a big roadmap. So we're at the stage now where we talked about last time, like I'm really starting to turn the focus to upgrading all fronts of the marketing plan. You know, before it was sort of just organic building in public, telling people about what I'm working on, talking about it on this podcast.

But now, so now I'm at the stage where there are multiple, very big projects happening and I'm a solo founder and I have a very, very minimal team around me. I'm finding that pretty difficult because like in audience ops, it was always like build a process, then hire people to fulfill the role and do it repeatedly for years. But this is like, we've got three or four big things to build and I need to give my personal input on them, but I also need to hire people to do a lot of the heavy lifting on this stuff and then manage them day to day and give my input. It's not just one big thing. It's like literally three or four big things.

So number one, there there's always the product work. Me and the developer, I do build some features, but right now we're actually doing a very, very big not gonna get too into it, but it's we're reworking a lot of infrastructure in the app around billing and around the business model for Zip Message, and and that'll be rolling out in in November. But it's the kind of thing that, like, oh, I thought that would take, two weeks, and it's taken definitely more than two weeks. And it's, like, also super complex, the the things that we're reworking under the hood. I need hours of my time to really hash it out with my developer.

So we've been doing that, but it's coming along. And then I'm doing a website redesign, just kind of began that process. And this time, you know, in almost all my websites over the years, I've done the full design myself. This time around, I did hire a designer. She's in India, and so far off to a really great start with her.

How long do you expect something like that to take?

This is a brand new person that I'm working with. So I'm, I'm just getting to know like her turnaround speed and things like that. My hope is that, I mean, we're recording this on October 22. My hope is to get the new website out by mid November, which, okay, let's be real, probably November. You are so fast, man.

I look at that and I'm like three months at least.

Yeah. Well, you know, I'm very much involved in this project. Like like, I'm hiring the designer to not do the whole thing start to finish. Like, I started it. I, hashed out the the sitemap.

This this is a very strategic website redesign. This isn't just a paint change. This is like, it is a visual paint change. That's why I wanted to hire the designer to make it look super impressive. But the purpose of it is that the current version of zipmessage.com, I created seven or eight months ago when it was super early and it was based on a lot of assumptions and based on like the earliest of the early conversations.

So what does the new site need to do that the current one isn't?

The new site, I mean, the positioning is all changing. The key use case, we're focusing much more in on that.

I like that positioning you got going on this week, my friend.

Yeah. So this this week, one one of my little marketing projects was to finally get around to writing and launching some of these comparison pages. You know, you might call them like competitor. We're going off on a little tangent here, but like these, competitor pages. But I think of them as like, okay, like the one against Loom.

Yeah. That's a direct competitor page. But some of these other ones are like more like competing against a use case or it's like use us and that. You don't need to replace that. It's just this should be in the mix.

So like I created four of these pages. One is a Loom alternative page. Another one is against Zoom fatigue. So we're not here to replace Zoom, but we are here to replace Zoom fatigue. Like that's the whole message on And that

that's what I'm referring to by the position that I really liked on

that one. Yeah. And then we did a third one. It's sort of against like Calendly, but really it's against calendar appointments and calendar booking tools in general. And again, we're not here to replace those things, but we are here to replace calendar appointments.

That's Behavioral literally competition as opposed to product competition.

I mean, literally all of the best customers on ZipMessage, and I constantly, constantly ask people, like, what's your favorite way to use ZipMessage? How are you using it? What types of conversations? I I can't stop asking customers that that question. I'm probably annoying the hell out of them with it.

It's fine.

But they keep telling me, some versions of like, these are calls that I would have had on zoom with my teammates or with clients that now we're doing asynchronously. Like we're replacing calendar bookings. That page that I made is it's basically making the argument like, yeah, you should have account. Like I have a SavvyCal booking link. Of course I do, you know?

Right. And use zoom, but it should be relegated to when it's actually needed.

But, but I also have my zip message link that I can send to anyone if I want to hop into an async video conversation with them. So, kind of making the argument there. Then like the fourth one is for slack. We already have a slack integration, but the thing with Slack is it's confined to your workspace. The, and the argument that I'm making is Zip Message extends outside of your Slack workspace.

So when you have all those people that you work with and that you talk to regularly, so freelancers, potential new hires, investors, vendors, biz dev partners, like those are conversations that companies are having all the time, but they're external. You wouldn't invite those people into your internal Right. Slack, you

Not as often.

So that's the point of that page. So so anyway, I created those pages and, made some tweet threads for them, you know, tried to SEO optimize them as as best I could.

So the site needs to needs to convey these options.

Those comparison pages, that's that's one section of the website. But the homepage and then we have like two or three use case pages. One is all about your team communication. One is all about your client communication. These are like alternate versions of the homepage.

Just reworking all of the copy, all of the key headlines and key pain points and benefits. So I'm doing all of that work like writing and rewriting these copy bits. I'm trying to restrain myself on the layout work, the wireframes, because I want to not influence the designer as much.

That must be hard for you.

It is very hard, you know? But we're off to a pretty good start. I've only been working with her for a couple of days now. And you know, I gave her my site map and my rough wireframe and draft copy stuff. She gets, she came back to me with, with like mood board, like pulling bits and pieces from other websites and like, she and came up with some really awesome ideas for layout that I wouldn't have come up with.

And so I'm really pretty excited about that.

So you're also looking at it from a branding point of view on like potentially new colors and new way to do it.

The logo, which I designed is going to stay The the red as as the branding is going to stay, but but we also might tweak the color palette around that and and fonts we are changing and and just the overall visual aesthetic of the website is gonna really be upgraded. So she's going work on those mockups in Figma over the next two or three weeks, and I'll be heavily involved day to day giving feedback. And then once she finishes that, I'll be the one who actually builds the website. Building it and shipping it will be on me and that'll happen in November.

Were you doing that these days? Do you still prefer WordPress? Do you go to Webflow?

No. On ZipMessage, and this is a total exception on just ZipMessage, but I wouldn't normally do it this way, but all of ZipMessage is the app. Zipmessage.com is the Rails app. The only reason I did that is because we have those shareable links. Like my Zipmessage link is zipmessage.com/brian.

You know, like you could have these brand, you know, zipmessage.com/rally. Like the, the shareability of, of these links is, you know, I was talking to Derek. I mean, the SavvyCal is, is the same way you need to have the root domain be shareable as part of the app, like compared to any other site that I've ever done, like, like process kit, the app is that app. Process kit.

Right. We've always separated for that reason.

And I would always recommend doing that except if you need this like shareability aspect.

Interesting. Did not think of that.

So, so it does make it a little bit more difficult on the marketing side because I'll be building it, but like, I don't really see an easy path to get into like an easy CMS that I can bring a team into. Like, we're not going to use WordPress or, or like Webflow or any of these because it's like, it's all in the Rails app. So, so that's that.

So you have a lot to juggle at the same time.

Yeah. So that was, at least I did find the designer and we're off and running. That that's like in, in progress.

Like life as a Gantt chart.

Yeah, exactly dude. You start this together. That's literally how I feel right now. I am finding it mentally difficult to manage it all because I have to switch from extremely technical conversations with my developer to design conversation with the designer to Yeah,

that's a lot of switching.

This next thing, which is content, right?

That is the founder thing. That is so hard to do. And we just take it as like, well, that's what you're supposed to do. But that is a lot of value generation, like in so many different directions.

Yeah. Yeah. You know, I I think a lot of people, you know, describe these kinds of things like, oh, why don't you just hire this or that person and and and outsource that or or delegate better? But in this early stage and just my style in general, like, there is an element of creativity and and strategy and literally talking to customers every single day. Like I have to bring that knowledge to the project.

I can't just hand it off to someone else, you know?

So of all those things, what's is there one that's most important? Like, is it all about repositioning? Is it all about new customers? Is it all about, like, learning from the existing customers? Like, what's what's the most important thing?

Yes. Yeah, competing priorities.

It's all of them. I actually do feel like they all need to happen at the same time because the developer is working on some pretty big product changes that I think need a new website to go with them. They probably won't launch on the same exact day, but ultimately they both need to be launched before the November, you know? Yeah. So so there's that.

But then then the other thing that I feel is falling behind now is content. And I'm still kinda strategizing around like what what is that gonna look like for Zip Message? I have all sorts of ideas that I would love to see happen, but it it cannot be just me doing this, right? So there is SEO content opportunities that we should be developing content assets and starting to rank for certain things that we don't have pages written out and guides written out and things like that. I wrote those competitor pages.

You know, there there's, we could be doing customer case study pages. I would like to continue doing like, like podcast content. I would like to get into a better newsletter cadence, not just announcing features, but like, let's actually build some, build an audience and build, build some real customer, maybe like a sub brand underneath Zip Message to really grow an audience. There's a lot of that kind of stuff that I wanna do. And and what I what I'm looking for, and I've been posting this nonstop for the last, like, three or four weeks is I'm looking for a writer, primarily somebody who is a really, really great writer, but I think of it as like writer plus.

And I know people are going listen to this and say like, oh, you're looking for a jack of trades and you're never going to find someone who has this mix of skills. This is where I'm going to get all complainy and rant

about shit. I don't think it's complaining, but okay.

Okay. Well, first, let me just describe what's going on. I've been buying job ads on a bunch of different job boards. Usually the headline is I'm looking for a content creator slash content strategist, and I'm looking for this person, not as a full time salary marketing position, but as a, basically a freelance contract retainer. I wrote in the ad like I'm, I'm ready to commit to at least six months, but my goal is this would be much longer than that.

I did not put like exact dollar amounts in the ad. My assumption is it would probably be a couple thousand dollars a month. Oftentimes I get the question back like, well, how many hours do you need? I feel like I'm not here to define or dictate how many hours.

How long it takes you.

Yeah. I'm here to say these are the goals for the business. This is what we want to do. Help me scope that out. What do you think we should do?

Because you're an expert in content strategy. So how about together we come up with a content strategy plan for six to twelve months and then we figure out what is that going to take in terms of time, in terms of skills that we need. Can can you deliver this alone? Do we need to outsource certain pieces of it to someone else? I'm looking for the person to have those professional conversations with and map it out and execute it and then figure out what the cost is.

And so I tried to put enough info in these job ads to say like, these are the types of things like wanna be doing written content, wanna be doing newsletters, probably developing a podcast. I wrote like that. You don't need to have podcasting experience, but if that interests you, that's a bonus. Like so far in the last three weeks, these are paid like featured job ads and pretty prominent job boards. I've received like 10 emails, like 10 responses.

And most of them are not even close to being good fits.

So what does that tell you?

Are you I don't know.

It sounds to me like a potential mismatch of where the job ad is, who is reading the job ad and what the job ad is saying. If you are offering what you just described in a sea of full time marketing jobs and the people reading it are looking for a full time job, I mean, might be one reason why you're just not getting the response.

I guess so.

It's it's a difficult because what you're saying is you need someone that has gone beyond the individual contributor level, beyond just executing on the strategy, has and has gotten to the point of giving input on that strategy, if not outright setting that strategy overall. But in that crossing over in someone's career and skill level, right, there's like a pyramid. So there are fewer people higher up and the demand for those people is way up. So a lot of those people are, they have either, either working for themselves in their own agency or are working full time jobs.

Yeah. And that's the thing. Like, I'm not as interested in hiring an agency because I

Just the nature of an agency? I mean, it's it's just individual people.

The the the nature of it, the cost of it. My hope is is to develop a long term, really fruitful relationship with an individual to be a key essential early part of the team on Zip Message. And I know it's not a full time salary, so maybe you don't call that part of the team, but in my view, let's work together for a long period of time and maybe that'll grow into something full time. And if you're not into full time, then you can continue as a contract retainer. Like, I'm sort of open to all those different structures, but the idea is collaborating with a person long term and let's build stuff together content wise, Right.

You

And it's not like you're like low balling or not able to offer anything. Is still significant amount

of Like I'm time trying to spend on this and I'm trying to find someone great. And then, you know, there's also like finding someone who is not completely foreign to this world of startups and remote work and asynchronous and just B2B SaaS in general. Like I've had a couple of contacts from people who are, who seem pretty talented, but they're just not from this world. And it would feel like a little bit of, too much legwork to bring them up to speed on all the different storylines and people in this world, you know?

We get that on the e commerce front where it's like, even if you're great to learn the language from scratch and the concerns is is a tall task. The recommendation that I made to, before we started recording was to look at a service called marketer hire and marketer hires is like top towel, but for marketing.

That's cool. I haven't heard of that one. That's cool.

It's it's it's big in the direct to consumer world because direct to consumer brands had a really big need. Right. Their teams got good at product development and branding. And then when they went to hire, they realized, Okay, we don't have a Facebook, Instagram, social media expert on hand. So and we're not maybe not ready to hire them full time.

And that's where marketer hire filled that gap. So it started off in the e commerce direct to consumer world, but now they've kind of gone toward marketing overall. And my understanding is that they're doing quite well. So that's, that's a good place to look.

Yeah, that, that is. I mean, a few months back, I did work with two different, basically freelance marketers and each one only lasted about a month or a month and a half with me. Both of them are really cool guys. We had really good relationships. I'm still in touch with them today, but what ended up happening was both of them were entrepreneurial and they were like, this is, this is cool, but I've got to work on my own stuff.

And they ended up like ending off client work and to focus on entrepreneurial stuff and, and like that. And I totally respect that. I totally get it. And that is the challenge with hiring for, for, for, I think specifically hiring marketers, because you don't see this with hiring developers. You don't see this with hiring designers.

It's relatively easy to find someone with those skills and bring them on, on, on a, on like a part time contract basis, but with marketing, there are so many skills involved. So yes, you could hire just a specific writer to write a specific thing that you need written, or you could hire a PPC expert to run your PPC ads. And I'm not looking to do PPC right now. I'm just saying, I do think that, especially when we're talking about content strategy, it's not just writing. Like writing is number one.

Like you got to be a fantastic writer first, But if you're in this space, especially if you're working with SaaS companies, you're not just a writer. You're writing email newsletters. You're setting up email automation. You're doing Twitter threads. You're on LinkedIn.

You're doing interviews with other people, you you've probably been on podcasts or or been around them, like, or listening to them. You're not a stranger to these kinds of things. Like, that's I think what what marketing in in B2B SaaS kind of looks like. Like you're, you're literally using lots of different tools and skill sets and mixing, mixing and matching, you know? So I'm sort of looking for someone to, to be that like creative force.

I mean, I'll tell you what, what we did is we broke up the strategy from the execution. So when we hired Sylvia as head of content, she's strategic. Now, she's she still does a lot of stuff. Right. And she she sets up Asana and she sets up the content calendar for the next six months and it's color coded and everything is like tricked out.

But when it comes time to write the article, she hires a writer to execute on writing that article. Now that individual writer, we want to work with at a longer capacity, not just once. We want them to get to know the company in the field and all that stuff. So right, so we have Katie as a writer and she's helped us write multiple articles. She's helped me edit my blog posts.

And then when we look at the content calendar, we assign Katie one or two articles every month.

Did you say Silvia? Yep. Is the is like the higher level strategist.

That's right.

That's right. She's basically a content strategist.

That's exactly right. So she's at the director level, head of content. Now at the same time, she's still like, okay, managing our Twitter and our LinkedIn. And she's telling me, Jordan, I'm going to tweet this from the company account. You retweet it and add your comments.

Or once you've written your tweet thread, make sure you go over LinkedIn and write it there and then I'll promote it with the comp. So there's like this coordination happening. And a lot of it is on the ground level of, you know, LinkedIn posts, you write it out and you hit enter. Like, no one's doing that for you.

I guess that could be one way to think about it is like, I hire a content strategist or marketing strategist, but not not the person creating the the stuff. Because a lot of these very smart marketers are starting to reposition their their offerings to be more like productized offerings around just the strategy. Like like a high price but one time engagement, we'll work with you, do a lot of interviews and stuff, and give you the strategy and the roadmap, but we won't execute. We won't write and create and ship stuff for you. We'll just give you the roadmap.

Now it's on you to go hire the writers and do the thing. So I've seen those around and that seems interesting, but I always sort of, in my mind, I keep thinking about this idea of someone who we just collaborate very closely at first it's about the strategy. And then you continue to work with me and execute the strategy that you helped come up with. Like, I think it's harder to find that combination, you know?

I would argue that the more valuable part of that is the strategy. And that's why it's harder to find. And if you can find the strategic part separate from the execution, then you should grab the strategic. Now, look, when I think about Sylvia, she's still gonna write a few blog posts. She's still gonna do things.

It's just that she's not responsible for all of

it. But that's what I mean is like, if you are great at content strategy, you're not a bad writer. You're probably a great writer.

Right. You you you have to be part of the content creation as well. Yeah. What got me about Sylvia and what, like, made me I mean, it's her and, like, personally is why we really wanted her to be on the team. But the thing that initially piqued her interest is she just created her own.

It's not a podcast. It is a podcast with video. And she just did it. She lived in San Francisco and she just got these amazing people to come on to her show and no one did it for her, which means she just hustled her way into getting the guests and then actually hosting and then producing and then publishing. Was like, so, so if you have the strategy part and you did it for yourself in this other way, then like, okay, you're the unicorn and just tell me how much you need.

And I guess this comes back to the funding. So is she full time salary?

She's full time salary. She's currently on maternity leave. Right? So all these things are like factors. I'm like, I'm going to leave this job and what's gonna happen when I have a baby.

We can be like, this is how you're gonna be treated.

Yeah. Like very competitive salary benefits, all

this kind

of stuff. And then, and, and then you have the budget to go hire the, the writers and all the other little things.

That's right. It was a very important part of it for her to know that she had budget because if then she gets hired and has to do everything herself, she's limited as opposed to here's right. The way I tell managers is that you are responsible for everything. That doesn't mean you're responsible for doing everything. You're just responsible that it gets done.

So I wouldn't look at that and be like, Oh, I can't do that. I would just separate these parts out and then add resources as you can.

Given my funding and constraints and also my interest in taking a much more active role in the content itself, like my thought is like, I will be very involved in the content strategy, like almost like co strategizing the content. Like I bring the customer knowledge and the space knowledge, but I want someone to bring the SEO analysis.

Yeah. Podcast and press and all these different channels.

And then also like the structure of how we should roll out content to achieve these goals. Like I bring the business goals to the content, right? So yeah, again, like it's like, feel like I'm, I am sort of being the content strategist, but I still need someone to work with. I can't just do it all myself, you know? Yeah.

Yeah. That's really just one piece of the overall strategy. I'm not putting all my eggs in just content. Like I have all these other things that I need to be doing, including like biz dev relationships and integration, sales, like all that stuff. I'm doing that.

I'm doing podcast tours myself. Like that's going to happen, but we do need this engine going for the next year. And I'm trying to like hire someone to make sure that that engine keeps going. I'm finding it very distracting right now, you know, but it's like something that also needs to get done.

Yeah. I think you'll, I think you'll find the right person. Maybe you have to adjust some expectations in how you think about it, but you'll you'll you'll find them. And if anyone out there is listening, that sounds interesting. Like, come on.

Make some intros. Let's go. Alright. I'm not only going out to dinner tonight with friends. I'm going out to lunch with a friend.

So I've gotten social crazy. Hopefully, I don't end up with like There

you go, man. Week. Good stuff, buddy. So, yeah, we'll probably be a couple more weeks until we hop back on the feed here, but,

yeah. Yes. Yes. Can't do next week. Thanks everyone for listening.

Brian, have a great weekend.

Later, bro.