Bootstrapped Web

Hello, everybody. Welcome back. Another episode of Bootstrapped Web. Mister Brian Castle, great to be with you.

Yeah. Great to be with you, buddy. Here we go. Another one.

Friday. My kids are off school. The whole house smells like waffles and bacon. Focus.

There you go. They, they just finished some renovations in bathroom here. So it's like finally quiet in my house and my dog is finally can can calm down instead of

like barking at these people for three weeks straight. So, yeah.

Oh, yes. Cool. It's Friday. It's it's been a big week for us. I'm a little tired, but it's been good.

I'm looking forward to getting into it, what we're doing, what we're learning. How about you?

Yeah. Always keeping busy. The to do list and the projects. I think I talked about this last time. Like there's just so many things that I need to manage at the same time.

It's, I'm finding that pretty challenging, but here in November, we're about to launch two things that are pretty significant, one coming before the other but I'm excited to like finally get some like new launchable things. There's been a lot of what you know, because I think in the first couple of months of Zip Messages, you know, everything was new, like every the whole thing was new and then every feature was was a big announcement. And then the last like two or three months, you know, there haven't been any major new features to announce publicly and we're just doing a lot of changes like under the hood and preparing stuff. But finally, November, we're going to have more activity coming. So excited about it.

Great. We're entering completely new territory now because we onboarded our first merchants. So we went from, you know, just no customers to yes customers. It feels like it happened all at once. The thing I'm happy about is that the intention of the funding announcement and holding off on it and timing it for when we could take customers on, that worked.

So the announcement and then our pipeline just got filled and then it went from, okay, relatively slow and like networking and partnerships and that sort of thing to all of a sudden sales demos every day. Nice.

Was there a particular story or publication that really drove a lot or is it just like the general activity of it?

The general activity of it. I think the, you know, the tech crunch was like checking a box. I think the business insider story was the best one. I'm really happy with that one. I felt like it towed the line between here's the truth of what happened with Cardoc and Shopify, but no unnecessary drama beyond that And was able to then focus on what we're doing now, which is obviously the goal of that type of an article.

So I got a lot

of the standard stuff, a lot of cold emails from HR software and whatever else, but also a lot of previous contacts that I've worked with in the past saying congrats and this looks interesting. And can I take a look? And when do you have time to talk? And let's do a demo. And I have customers that are on BigCommerce and let's get into that.

And so it all kind of came together all at the same time. I forgot how much I like and how much energy and excitement I get from sales demos. I just haven't done, I haven't done them. I haven't been in that role at Cardhook. I started to, there started to be a lot of distance between myself and the sales conversations and I would get it in what we would call the demo download.

So once a week we would do a demo download and the person doing the demos would give us like, here's who I spoke to, here's how many people, here's who's interested in why these are the feature requests. So I wanted to keep getting that information. But what I always told that person is that they quickly become the most important person in the organization when it comes to feedback and understanding what we need to do next, where to take the product and what's missing, what people are excited about. So it's fun to be back in that seat.

Yeah. And you're doing all those demos yourself.

I am. We have a biz dev person that's doing sales and partnership stuff, but he's a bit more junior and it makes sense for me to do a lot of the demos now. And he joins and is learning and basically seeing how I sell it and how I position certain features and problems and that sort of thing. And I assume that pretty quickly he'll be doing more of them. And I'll do right.

Let's say right now I'm doing either a majority or all of the larger merchants. And in the future that will just start to shrink around the percentage of merchants that I want to handle in the first conversation versus not.

Yeah. When you're on one of those demos, it's like that, that's literally the moment where you can see where is this company at? Where is my comp? How is my company doing? Right?

Because that's literally like how easy those conversations flow or like answers to every question that comes up and request that comes up is like, yes, we have the solution for that or no, we will have the solution but not yet or that's an interesting question. I haven't heard that one before. Like everything sort of like flows down from there. You could talk to your team and see internally where you're at, but ultimately when you talk to the customer, that's where you know what's happening.

Yes. Yeah. I think that's a good way to describe it. You really, you can feel how close or far you are from satisfying what the market wants. So we're definitely getting that really positive feedback around most of it.

And then there's that gap that we know we need to build the integration for that and we'll need to work with this payment processor. And we find a merchant that's perfect, that wants to work with us and everything is amazing, but they use a tool that we don't integrate with. And so we have to hold off another month or two. So. Yeah, I'm I'm trying to keep my like expectations in check because this is not card hook.

This isn't years in that we can say yes to so many. Right now, the percentage of merchants that are qualified and want to work with us, but that we can satisfy is the lowest it'll ever be. It's at the starting point of who we can satisfy and say yes to and be able to accommodate. And that's just going to take time to be able to say, to increase that percentage.

Yeah. I go in and out of this with ZipMessage. Like I feel like I'm less directly in touch with customers than I was in the earlier months. And it's been very different than like, than it was with Process Kit because like with Process Kit, those demos were a big part of it. Like pretty long phone calls walking through all the features and how you can build out workflows and things like that.

With Zip Messages, it's just not that type of tool. It's so fast for a customer to start using that a demo is almost, I don't wanna say pointless, but like, I just haven't, I haven't had requests or needs to do a demo because it's like, if you want a demo here, let's just have a zip message conversation. Now we're using it. That's the whole product. And that's how it's been.

Like, would send messages to new trialing users to ask them how it's going and how they're using it and get a sense that way. But I haven't done that in a couple of weeks. So I need to get back on that. You know, I feel a little, a little bit out of touch from where I was a few months ago.

Here's a question for you on that. You feel more out of touch because you're doing fewer demos or is it because you're moving toward a self serve model that doesn't rely on direct conversations every time?

It has been self serve pretty much since the beginning. In terms of being in touch, it's literally like, am I getting on ZipMessage conversations with the customers or am I not? And, you know, for the first few months I was doing that very often and now lately I've been so busy that I haven't haven't been on as on top of that as as I usually am. I get into conversations when when they naturally come in like through support requests or feature requests and stuff like that. And then, and then I get into a good conversation.

But a few weeks back I was, I have a list of the current trialing users and I can, I can send each of them a zip message and, and that's been really good? So I need to get back into that habit like that. That's my form of, of doing demos is like, because there's never been like a manual onboarding or, or pre like before they sign up, like showing them how it works. There's none of that. They just sign up and then they can start.

You can fire up a ZipMessage right away, know.

That's an advantage.

It's really gonna change. Actually the thing I want to talk about today is I hope we're ready to launch this by the time this episode airs next week. We are launching or at least experimenting with a free plan. So we're going to try, the freemium model on, on Zip Message.

Okay. And so let's, let's dig into that.

Up until now, since the beginning, we've had a fourteen day free trial, no credit card upfront.

Okay, no credit card. So you can you can still come in and make an account right now before you before you have a freemium tier.

And starting when we launch this next week, there will be no more free trial. There will just be a free forever plan and you can upgrade whenever the time is right for you and you know hopefully the way that we're designing it, I could talk about this is you will bump into the limits of the free plan multiple ways. My hypothesis is pretty quickly you would hit some of these limits And the other part of the hypothesis is that it does, it's the type of product that takes more than two weeks to know that you are using it regularly enough to warrant paying for it. I think that combined with the limits should convert free users to paying. I just think that a free plan is the better form of trial for this type of product than a timed trial.

Time based. That's one of them and then when you think about freemium, it's a marketing strategy and a growth strategy. So Zip Message has a viral component to it. Almost every time you use it, you're sharing it with someone else, whether it's, whether they're within your organization or very commonly someone outside of your organization. That's sort of a big positioning factor for zip messages.

Like you can, you can talk to your teammates on it, but you could also talk to your freelancers. You could also talk to your clients and your customers with it, your new hires and things like that.

So yeah, I agree with focusing on that element of the model as, as right.

That's the big reason for doing it is like, it is a viral product. And I think that without the free forever plan, just really hampers that the virality piece of it. So a big, like another big focus in product going forward will be the shareability of it, you know, making sure that we have the right prompts and calls to action to, and, you know, we already have like powered by zip message, but like just more opportunities to like, Hey, like invite someone else into this conversation and share this, you know.

Right. Or be able to use this yourself, click here for free. I mean, every time I sign something on DocuSign, I'm presented with a, you just use DocuSign, click here to get your free account. I happen to have an account with DocuSign, but still the nature of that makes sense where if I have a good experience with the product as a user, I might want my users to have a similar experience with that.

Yeah. Yeah. And so I, you know, I spent a lot of time thinking through what the limits should be on the free plan.

Yeah. What are you worried about there?

Yeah. So, I mean, the first one is obvious, like we'll have to limit the length of time that you're able to record messages. If you're on a paid plan, you can record messages currently for for for an unlimited period of time. If you're gonna be on the free plan, out of the gate, I went back and forth on the number of minutes, but we're gonna start with a one minute limit on each individual message, but you could still have unlimited messages within a conversation and you can still have unlimited conversations. So you can still use it as much as you want and share it with as many people as you want and use it as frequently as you want, except every time you record a message, once you reach sixty seconds, it'll, it'll stop you.

And we've got like a ten second warning countdown kind of thing.

Right. Yeah. I think about that with, I use loom and the other day I was using it, but I wasn't logged in to the right account and I was recording something important and I hit the five minute limit. And then every once in while I hit the think it's 25 total videos in your free Loom account. And so you reach that.

That's kind of easier. I just go in and I delete one that is unnecessary.

Yeah. Well, so that that's also what we'll be doing. The free plan, you'll be able to see thirty days of history. Any messages that are that are more than thirty days old, will not be visible to you. So that's another one.

And then another another limit is the vanity URL. So with zip message and this is one of the big differences from from from Loom is that, you know, we give you your own shareable link like just like a Calendly link or a SavvyCal link, you can share your zip message link to start an async conversation with anybody. So when you sign up for a free plan, it'll be zipmessage.com a random string. And we actually built a thing where you can see if your name is available and you can hey, it's available. You can upgrade to get your name, you know?

So, so there'll be that sort of prompt for you. But yeah, you would need to upgrade into one of the paid plans to, to get zipmessage.com/jordan or whatever, you know. The recording length, the history, the vanity URL, and then a couple of other like features like, like transcripts are not available on free and message templates and stuff like that are not available on free.

Right. So you can really, you could use the core functionality of the

conversation And we have a Slack integration, which is not available on free as well.

Yeah. Well, these sound like dials you can turn and experiment with.

Yep. Yep. So we'll see. It'll be interesting. A lot of the effort over the last three weeks has been just preparing all those billing aspects and you know, there's a lot more to it than just clamping on a limit on, on like hiding a feature or something like that.

There's like, what do you do when someone has been unpaid and then they, and then they cancel or they downgrade back to free. Now we have to like, you know, reset certain settings in their, in their account and things like that. So we've had to work through a lot of that logic. And then also a lot of dev hours on just being able to track usage in the way that we need. Cause you know, with free, like I'm going to need to really keep an eye on a lot more key metrics now.

I mean, how much are free users recording? And, and how frequently and what is that costing us and all that. Like there's, there's going to be a lot of, a lot of tracking there.

Yes. And how many people are hitting that sixty second limit constantly, if that's the right number. All right. So we're going to come back to this conversation in a few weeks, months, and look back and say, all right, what happened with freemium and see if you're sticking with it or if you want to change it up or which metrics you're changing over time.

When I first started Zip Message, I think I talked about it on the podcast a while back. Was like, thought that freemium would sort of made sense for this type of product, but then by the time I launched it, I had changed my mind. I never default to a freemium model. It's always pretty scary. So, so and I think I launched it with the fear of doing free so I just went with the fourteen day free trial.

But you know the other thing that I think is important is if I'm going to experiment with free, I think it's a lot easier to do that now, like during the first year of ZipMessage than much later, you know. Let me learn about it now while the stakes are relatively lower than they would be a few years from now, you know.

Yeah. I'm curious to see what impact it has, if any, on just the sheer number of signups, because you don't add much friction into your free trial right now. Right? You're not asking for a credit card upfront. So it's not like you're removing the credit card requirement at the same time.

They're not

Right. Yeah. I think off the bat, it's not going to make a big impact on the number of signups. Just introducing the free plan is not going to drive a ton of new traffic into the top of the funnel. Like I am working on traffic strategies as well right now and making a lot of plans there.

But I think it's a little bit more longer term as we build our traffic, hopefully that flywheel will get up and running faster whereas like when we, cause you know, we'll get our current level of free trial signups maybe slightly more with the free plan but those free trials are A going to share it a lot more and they would stick around longer. Like they're not just limited to fourteen days. Right now, you don't convert after fourteen days.

Right. You're no longer in the pool.

You're no longer in the pool of people who could share it and spread it, you know? And that should expand over time, you know?

Yeah. I think that's, that's where the biggest impact will be that the pool of potential customers and people sharing it just grows much, much larger over time. Okay, cool. We're going to see how the experiment shakes out.

Yeah, man. What else? What else do On you

our side, we just had an all hands a few days ago, two days ago. And the theme there that I wanted to make sure that everyone in the company took away from that all hands meeting was like prepare yourself for a different challenge. Like, let's say you've been working at the company for six months. You are used to a certain cadence and a certain set of priorities around what you're doing. Let's say you're a front end engineer and you have your plate pretty full with what your responsibilities are and what's divvied out among the team and how what you do fits in and what you're responsible for and so on.

And what we're about to do is we're about to scramble people's priorities in a challenging way because A new merchant comes in. That's the priority. The priority now is traction and getting enough traction to get to series A and then building out the team even farther and getting even more traction. But right now we have the team that built the product. We don't have the team to handle the customers and the traction.

I don't want to go out and hire too far ahead of ourselves here. So we're not hiring a big support team and a big success team. We're saying to ourselves, no, we're going to do the support and success because that's who needs to really hear everything. We want the engineering, right? So Rock is getting on.

Rock's not getting on the sales call. I'm doing the sales call. And then that next onboarding call is with our VP of product, the absolute top person in the company at the product level and our CTO, because that's who needs to hear from customers directly right now. And that's why I want to make sure is directly in touch with customers. So normally that would be like a success role, someone who's responsible for onboarding.

And so as we fill this pipeline and start onboarding people, it's going to be a full team effort. So you're not, going to be siloed off. If you're a front end engineer, you're not going to be siloed off from what merchants need. They're to start to scramble your priorities. And then we're going to have this difficult period that we're about to enter into over the next few months where we don't have the onboarding team.

We don't have the solutions engineering team. We don't have those people who absorb that work from the pipeline. And so it's going to fall directly to the engineers who are building and we're really going to be asking them to keep building the way they are and keep with the roadmap and the priorities on the product and the timelines that we've set there. Oh, and also here are these new unknown tasks that real merchants are going to start to have, and it's also going to be a responsibility. So it's really like a this is going to be a challenging

like like quick ship features or changes or things like that.

That's right. We already had one. We already had a hot fix, right? So we we we were onboarding a merchant and we went to onboard their account and it didn't work because it was a it was a situation we hadn't seen before. They were building their front end completely detached from the platform swell that their back end and our swell integration required a front end.

It was like looking for that piece of logic and it returned a null effectively because we hadn't built that out yet. So immediately we say, Okay, we're sorry about this onboarding call, not going the way we expected to. Let's have another call tomorrow. And then from that time to the time of the next meeting, got to get the hotfix out. So that's just an example of like, you know, sure, it's a small fix, but you know what it does to an engineer.

It throws them off for hours to make sure that go through the QA process, then deployment, all these other things. So we're about to go through a challenging period where we say to ourselves, merchants and traction are the most important thing. Oh, and also don't lose track of the roadmap because merchants want all these features so we can get the traction. So it's, it's just going to be a difficult few weeks.

And it sounds like it's that strategic. That's not like, I mean, yes, it's out of necessity. You don't actually have customer success and onboarding people on the team yet, but it's also strategic. You want that you want those engineers, the team to be bought into this is what customers actually want. You are directly hearing it from customers.

That's that's why that's that's the meaning behind what you're, what we're pushing towards here.

That's right. And we're also building out the process as we do it. So we're running over the railroad tracks for the first time is the analogy that we like to use internally. And so we say it doesn't matter that we don't know exactly what the process looks like. We're going to lay down the next set of railroad ties as we need it.

And that is really difficult to do all at the same time. But then once the railroad tracks are set, it's easy to run back and forth over them. So we're having all these very synchronous, very Zoom, very six people on one call, like inefficient type meetings because we're saying to ourselves, Okay, we got a merchant. They're interested. They came.

We had the onboarding call. They're integrated. Like, what's next? What are we thinking of? What are we not thinking of?

Who's responsible for it? So we're just building out this process for the first time and identifying, Okay, so that means they when they come into the system, they're in Asana and then they're at the top of the funnel. And so we also want the tech team to have a Confluence doc that goes with that. Okay. So now when you create an element in Asana, a Confluence doc also so that the product and engineering team can follow along with what's happening in the process.

So there's a bunch of new stuff and I like it. I'm very comfortable with not knowing what comes next, but a lot of other people kind of want more structure.

Yeah. Zip message is so small that it's those tooling in the project management tools and workflows are so minimal and so not figured out yet because it's with my developers, just me and him in GitHub and that's we've got our systems down in there. But then when it comes to marketing, it's basically just me and I'm working with a couple of different marketing people here and there and bringing someone, someone on soon have just have not figured out how do we manage what everybody's working on

right now? I would say there are some advantages to not being overbuilt and overdeveloped, and we have some disadvantages than just the sheer number of people involved. And so we're trying to not Hamper ourselves even more by hiring more people and building up processes before they're ready and so on. But it is interesting just the balance where now there is an added factor on traction and how to use that traction to get towards series A. And that really informs like informs timing, informs who to work with, how many to work with, how many we feel that we need to work with or should work with.

All these other factors are just part of it. And there's kind of no avoiding that. It doesn't make sense to avoid it.

Yeah. Nothing like real customers to kind of drive what's most important. It's the thing that the customer is asking for. Okay.

Yep. Yep. Yep. Which is which is oddly kind of new to us.

Yeah. Yeah. Talked about, I think last time I have started working on a website redesign for Zip Message and I hired a designer and this is a very collaborative project and we're making really good progress on it now. It's not close to launching, but I am hoping before the November I can get this launched, which will require a lot of hustling on my part. But it has been a very interesting process of designing this site.

It's been very different from all the other ones because I would always do everything myself and this time I have a designer working with me, but I'm still very, very involved. So like, I mean, purpose of doing this at this point is that it's the current site, copy and the positioning was from many months ago. So I've learned so much about what the key use cases are and what our true positioning should be. So I rewrote all the copy and I did some layouts and then and then I had the designer really created a really awesome like just refreshed look and feel. We didn't redesign the logo, but we have new fonts, slightly new colors.

Yeah. I saw on Twitter, it looked good.

Yeah. So I, so I really liked that. And so now I'm at that point where it's, it's tricky because like the homepage has, it's supposed to have a lot of screenshots of the app obviously. And we're going to have a bunch of videos and like animated, like real screenshots, but like animated with video and stuff like that on the homepage. It's going to be pretty cool.

But since we're tweaking the look and feel of the site on the front end, a lot of those tweaks in styling and fonts and colors need to be carried into the app as well. And those apps screenshots that we're going to feature on the homepage need to show the new look and feel. So now I've been working in the last week or two on making all these like stylistic updates in the, really refining the interface in the app to kind of match up with where the front end website is going so that I can then take screenshots and videos and then feature them on. It's like a chicken and the egg thing, right? Like you designed the new website, then you got to update the app and then you can go back to the website.

I mean, none of that stuff is live yet. That'll, that'll come in like later November. But when I'm working in my local dev environment, it's just visually a lot of the changes are super minor, but then taken together across the entire screen, it's just visually a lot more polished and it feels like just like a much more mature product, even though it's still pretty young, you know?

Okay. You feel like you have the positioning a bit better in terms of the, just the headline and features that you're highlighting?

I really think so. I mean, there's definitely gonna be some learning there once that goes live. I mean, the top headlines and everything are gonna be changing. So I'll still need to dial in exactly what wording we're using and and which phrases from customers mouths that we're gonna pull into this copy bits here and there. Right?

I have like a draft of it all and like I know where we're focusing and and the and the main message, but I think as as I get into closer to launch, I'm going to really try to dial in the exact words we're using. That'll be really interesting because I think once we have the new website up, you know, thinking about marketing like that it does change these kinds of things. This early in a product's life cycle is also a chicken or an egg thing because the customers that we've had up until now were attracted to ZipMessage based on what they've heard about it and what they see on the current and like old website and the positioning. Right. And some of them have converted, you know, we have really good customers and then we have a bunch of people who did not convert or they converted and then they churned or something like that.

So it's like we want to make the new website based on what we've learned from the current customers. But the new website is going to attract hopefully more of the better customers and less of the random people, you know?

Yes. Yes. You could always be taking a step back accidentally, but you know, what else can you do? Yeah. We're doing a little facelift.

I have been able to like kind of look at

the current customer base and see like, okay, this segment of users are using it a lot and they've been using it for many months pretty regularly. Like how can we get more of them? And that's what the new positioning is kind of aimed at.

We are, we're doing a little facelift next week on the site. Like you said, these little adjustments, but they do add up to a better experience. But we have a more daunting challenge over the next few months of like the full website because right now it really is like a glorified landing page with a with a blog. So about page will come out, Some different changes, but I feel like we have we have a big job. I'm starting to talk to copywriters just to see if we can get some help on it.

Yeah. Yeah, man. So that's that's all we got.

Yeah. That's about it for me. Friday afternoon. I don't know what I'm gonna do with myself. It's beautiful out and go hang out with the kids for a little bit now that they're off school.

Nice. That's it.

Gonna enjoy some some fall weather out here. Should be a good weekend.

Heading to San Francisco this weekend. We're excited for that.

Alright, folks. We'll see you hopefully next week. Maybe the week after. Yes. We can make it happen.

Alright. See you, Brian.

Later.