Bootstrapped Web

Bootstrap web, we are back for another week. Is this actually three in a row, Jordan?

It feels feels pretty good. I like it.

Yeah. Yeah. And all of a sudden, we have Twitter kind of doing the work for us for this podcast. We've got a bunch of questions. I don't know that I would call these, like, technically, like mailbag questions, but it's more like they're, like, helping us come up with interesting topics to riff about.

I love it. Appreciate the help. Absolutely. Yeah.

And there's some good ones here for us to kind of chew on. See where it takes us. It's Friday. I'm in a good mood. I got a button down on, which I don't normally do.

I did the whole family photograph thing. Okay. The holiday cards, you're on that holiday card.

I expect the card every year. I wait by the mailbox every single day in December for the gal card, yep.

Good. You and several other 100 other people.

So we get we got

a beautiful day today and it's so much fun to like, you know, almost you almost take a step back with the photographer and like watch like your family, like posing and be like, wow, look, look, aren't aren't I lucky? That's kind of the the the overwhelming feeling is this gratitude.

Nothing like bragging about your kids with some photos. Yeah. Before we dive into it, so next week, I'm going to what what we call our no snow tiny comp trip out in Colorado. We started this last year. So, you know, we've been doing big snow tiny comp every winter in Vermont and then in Colorado.

And that Colorado crew, we added a fall trip in September starting last year. So, I'm doing that again next week. Dave Rodenbaugh is organizing it again. And instead of skiing and snowboarding, we're doing some hiking and mountain biking and talking business.

Sounds great.

One of my favorite things to do are these tiny conferences. I just can't get enough of them. It's just fun to go hang out with some longtime friends, but I've talked about this before, but it's just such a great exercise. Mean, I I literally, like yesterday I spent at least half a day preparing my slides for a session that I'm only going to give to like 10 people.

Right, but you're thinking about it.

You know, we get into everything that's private, you know, just sharing it all, going going deep, you know, get critical constructive feedback. It's just so valuable. It takes hard work for me to prepare and gather up all the metrics and create a slide deck and frame my session and my questions and things like in a way that will be constructive. It's just a good exercise overall.

Are the sessions, let's take for example, the session you prepared for, is that for you to present information and get feedback? Or is that for you to like teach other people on a topic?

I think when we started in the early days of Big Snow, it was a little bit more like, Hey, just share something cool that you've done. There's little bit of that. It's like just showing But it's also like, I think it's become, since we have the same people coming back going on like nine years now, we are much more open with each other and it's more about, I would call it more like a state of the union, almost like what a shareholder letter or like an investor update email would be, but in the form of a conference talk where you're sitting around like a baller Airbnb in a beautiful location. That's how most of us treat it, is like sharing our numbers, sharing the updates since our last trip a year ago, what's been happening over the last few months, key initiatives right now, and maybe some big open hairy questions that we're dealing with right now.

Yeah, it's a great opportunity.

I mean, really it's a session for like twenty minutes plus like twenty minutes of the whole group kind of digging

And I'm sure the conversation continues when you're out to dinner and having a drink and taking a hike. Yeah, there's so much going on in your own head while walking around during the day to have the opportunity to start sharing that. Sometimes I feel like I'm oversharing. I just meet someone like, yeah, really struggling with this hiring thing. Hungry, hungry for that conversation.

Yeah, man. All right. Well, let's dive into it. Today we've got more questions, so I don't think we'll get to all of them, but definitely some for future episodes. Where should we start?

What do you think?

I mean, I think you want to start with the tools and I want to get it out of the way. Okay. Maybe you, I guess we forget teaching. It's really just sharing how you got to the conclusion to use a certain tool, right? That's kind of where the value I

think this will be probably a somewhat quick one, but I have noticed this thing where, okay, so Zip Message is, well, we're about a year, a little more than a year and a half into this company existing, right? So all of us sell tools to companies, right? If you can market and get your tool in their hands sometime during that first year of the company, you have such a higher likelihood of getting in. Because once some of these tools are just so sticky, like I could already see how we're using Notion right now. It's going to be near impossible for us to leave Notion in the future.

Yeah, which is

kind of okay. Okay, so how do you want to do this? Do you want to talk about an area and just very briefly talk about what we use and why?

Yeah. So some people ask about Techstack. We can cover that. Maybe we'll cover like some marketing tools and whatever other ops tools we've got going. How about Techstack?

I know it's not your side of the business, but

It's it's not, and I can't speak them that intelligently on it, but we are a Laravel shop, as we say. So that is our base, and we use a lot of tools in that ecosystem. What's that admin called? Laravel, not Vapor.

Laravel Spark? No,

it's not Spark. So we use a lot of tools from the Laravel ecosystem as our default, hey, we want to build this, What exists already? Which is part of why we love it so much.

Are you guys doing something on the front end like React or Vue or anything like that?

Yeah, we use Angular on the front end.

Angular, okay.

Yep, that was a decision from a few years ago and our front end lead is kind of very good with it. And we effectively have, we have multiple parts. We have the checkout that lives on the web, And then we also have the admin that the merchant interacts with. So we kind of have two products in that way and each tool has its own stack.

I've purposely kind of stayed away from these heavy front end JavaScript frameworks. I just have not felt the need to add that much complication on the front end. Angular seems like the one that I'm hearing. It was huge a few years ago, and then I hear less and less about it. It seems to me like React has sort of replaced it.

But I have not ever used React myself at all. I know Vue is also kind of popular. We are on Ruby on Rails. I love it. I love everything about it.

I feel like I'm gonna be on Rails as long as it's a viable option. You know, back back in 2018 when I was like really deciding like which ecosystem to sink my teeth into and learn, it was either Laravel or Rails. And that that is still my recommendation to anyone if you're trying to learn back end, trying to learn how to build apps. Just choose one Yeah, of

or one of those two.

Yeah, that's correct. Yeah, PHP or Ruby. I mean, front end super lightweight. We use Stimulus JS, which works really well with Rails. I'm really heavy into using Tailwind CSS.

I think that has been just an absolute game changer in the web industry as a whole, but it's been so helpful. I remember that I did not use it in the beginning of when I started ProcessKit. And it was like a year after that when I really got into Tailwind and I completely regretted not using it on prod. It made it so much harder to maintain and refactor and redesign stuff. Zip Message, we can move so much faster, not just building out new stuff, but the big thing is like refactoring with Tailwinds is fantastic.

Does hosting an infrastructure matter as much to you as it does to us?

It does. And this is something that I sort of keep an eye on in the future. I think it'll probably change over time in different areas. So we're still on Heroku for our servers and database. I expect that that will probably change at some point.

It's not like an immediate concern, but we'll we'll probably migrate to something else in the future. AWS, we are heavy users on. We do, basically all of our processing there. We're using multiple AWS services to to run ZipMessage. That too is something I keep an eye on both in terms of costs and complexity to build stuff.

So that too might change at some point, but it's not an immediate, not in the near future.

Yeah. We're AWS all the way. How about on product? How do you manage your roadmap workflow?

Yeah, so heavy into GitHub. GitHub is the tool for us. I would say there's two big project management tools that we use in the company. So GitHub is basically just me plus my developers. GitHub issues, we use the Kanban view in GitHub to organize everyone's queue and what's currently in progress, what's ready to deploy and all that.

And then we have a separate board for bugs and then a separate board for it's just called roadmap, which is where we throw everything else that's for the future that goes there. And that's where I play around and reprioritize things. And then I move it into what we call our current board, what we're currently working on. And that's a heavy, I'm in there all day long.

Right, that's where you end up living most of the most

Yeah, and the other side of the business is Notion. Anything that's like not dev related is kind of organized and communicated in Notion.

Including projects and tasks?

Yes. Yeah, not projects for the developers. That's all in GitHub. Right, all in there. And that's the one that took me longer to adopt, like just even having anything in place in that area of the business.

Like the first year I had basically nothing because it was basically just me.

Yeah. In your head plus roadmap.

Yeah. In my head, or even just like my own personal notes, whatever notes, documents I ever want to use personally. Like I don't, I didn't care about collaboration because it's just me and I might be hiring a contractor here and there, but now I have a marketing team working with me day to day and I needed a legit project management solution. And I tried them all. I tried every single one of them.

Really?

And Notion took so many different tries to finally click with me. And there there are things that that still frustrate me about it, but it is the most flexible. We can create Kanban views. I also like that I what I use Notion a lot for along with Claire in in the company is just kind of brain dumping new ideas for new marketing projects, just using just their their page editor and lists and toggle lists and all that kind of stuff. Just like map it out.

There's a lot of just like knowledge and like a lot of strategic planning happens in docs there.

I like how flexible it is where you can go from paragraph to bullet points to task list, in real fluid. There's no, you don't need to change anything. Have to go to a different doc. It's just kind of a blank space.

And we also heavily use databases in Notion for a lot of different things, you know?

Oh, like the Excel looking?

Yeah. Yeah. So while I'm still on Notion and project management, like we use ZipMessage a lot too. So we link a ZipMessage thread to a a Notion page or a Notion project so that we have, like, a running async video conversation about the project that happens on ZipMessage, and then we have it kind of tracked in Notion. But then databases in Notion we use for one is one that logs every every person does a month a weekly update where they record a Zip message.

Here's my weekly standup, what I did this week, what I'm working on next week, any blockers. They log that in a database and post it in ZipMessage. I got this idea from Rob at MicroConf, a marketing change log, which was such a great idea. I can't believe I wasn't doing it earlier.

Like marketing website change log or?

Well, he called it a marketing change log and we use it mostly for that, but it's like an everything change log internally so that we have a running log. It's a database in Notion for any change that might affect a revenue graph.

Like pricing changes, onboarding change.

Every little change that if I ever want to look back in history and I see a little blip on a graph somewhere, well, what happened during that week? Oh, we, we logged the fact that we changed our pricing that week, or we logged that we pushed out a new feature update or, or that we sent out an email newsletter announcing a new feature or that we got a new mention on some big blog or all that stuff gets logged into the change log. Same thing with infrastructure changes too. I started logging those too, like dev, because we do server upgrades. We change out a tool for this or that.

It's good to track the history of that stuff. So it's all in the same change log. We just categorize it with tags and yeah.

I like that. That's clever.

And just recently, since we're talking about it, we could talk about tools that we're using for analytics. Mixpanel is one of the many tools I'm using for analytics, but they have a really cool feature called annotations or something like that. And I rigged up an automation so that anytime we add something to the change log in our Notion database, it automatically fires an annotation into Mixpanel. You

can have it

on the graph. So, and literally every graph that we ever look at in Mixpanel has every notation of what happened.

I knew you were gonna put me to shame in this conversation. That is very clever, very cool. On our side, we are super deep in Jira and Confluence. That is where the entire development process lives. Everything from planning to current sprint to change logs to release notes to features being planned, scoped.

It's all in Jira and Confluence. And that's our religion basically in the company.

I know those are so popular and I've never even touched those tools in any work. I've just never seen them.

They're popular in the sense that you expect that a ton of companies use them and they're a little antiquated and old and annoying, but as long as everyone uses it, it's incredibly useful. Yeah. So that's us and that's like we have this ongoing kind of joke between myself and Jessica, our VP of Product, because she's super organized and loves Jira and Confluence and I always want to use other stuff. Our company has a developer first DNA because we built the product for like twelve months before doing anything on the marketing side. So that's really that side of the organization.

That's how I was with ZipMessage. That's I didn't even really settle into Notion until a little bit later on. What do you do on the marketing side and projects and things like that?

So sales and marketing are still immature in the organization. And what we did there on sales is we used Pipedrive for a while. And that is just so flexible and so easy and just get it started, put a few integrations in and boom, you're going.

So that's all over Pipedrive in audience ops. Cool.

Yeah, that's what we did for maybe the first six months of starting to go to market. And on marketing, we didn't really have anything. We used Asana a little bit, but it didn't really, there wasn't that much activity beyond what I was doing. And we recently brought on both a sales team and a marketer. And they immediately got together and came to me within a week of joining the company and both said the same thing.

Either HubSpot or Salesforce, which one do you want? And it's interesting that the way we think about tools and how we sell tools to other companies and so on. You mentioned being able to get into a company early as an advantage. We always feel like in that conversation, the advantage to those two companies, that they feel like the only two options of any maturing company.

The sooner that you can get into those, the less pain that you'll have in the future when you'll inevitably want to go to one on one.

Exactly. And everyone wants the proverbial single source of truth, right? They want to understand a customer's history from the time they engaged with a marketing asset all the way through to sales and then onboarding and success and then like upgrade.

You went with what HubSpot?

We do go to HubSpot.

I think of HubSpot as like a big tool that covers a lot of big areas, right? So is that your CRM and your email marketing tool and what else?

So it's interesting. I always pay attention when we deal with HubSpot because they're very good at what they do. And I learned a lot from the last sales process of CardHook. So similar thing. What you'll see HubSpot do is all about bundling.

So they have a sales tool, support tool, a marketing tool, like they have all these different things and then you can buy them in a bundle. And so really what they want you to do is just adopt it for everything and the pricing is so no brainer that you should just get the whole bundle.

Customer support ticketing too, you're using it.

Yes. Well, here's the thing. Next week on Monday, we have our first customer success manager joining. She's going to have a big decision to make on whether she wants to run customer success and support inside of HubSpot or go with the tool that I like best for that, which is Entercom. So I like to leave it up to the managers of each thing and then basically tell them, here's the deal.

If you want HubSpot, we will pay for it. And it's whatever it is, $20 a year, but then you're going to use it. So don't come back to me in a month and say, I don't love it. Can we go to something else? It's one of those things where you're just making the decision and like, that's it.

Yeah. Yeah. So covering some of those pieces. Email marketing, I'm still on customer.io. I really like it.

They've they've been really powerful for basically anything we wanna do. I really like the way that they they have set up their interface and capabilities on automations and stuff. Haven't done a lot of really complex stuff for Zip Message on that front, but I like that it's all there and there's a lot of power that we can

You can go as far as you want there. Yeah. We have used customer.io up until now and now the marketing team wants to suck it into HubSpot.

Yeah. That's what I think of when I think of HubSpot. It's mainly email marketing plus they cover all these other bases.

Yeah. Look, Microsoft laid out the inevitable path for domination. You just get deep enough in with a company and then whenever there's an innovation, you copy it. It's not quite as good, but it's still a no brainer to use it because you're already paying for the bundle. And that you can look at intercoms, like their breadth, how wide they're going, look at hubs.

But like this is just kind of the obvious path if you want to win and go public and get all the metrics that you need to do that. It's not fun.

Email support help desk. I use, I think they're bootstrapped, I'm not sure, HelpSpace. So I really like them. I switched from I was a long time through many businesses using HelpScout, which I still think are great. They're sort of like the go to for a lot of companies for help desks.

I switched to HelpSpace about a year ago. You know, the main reason I I really like them is because they put a lot of love into the KB docs. They've got some features there that I I always felt like that was one of the areas that helps help Scout was a little bit behind on is the the managing the KB docs. Like the editor, they've got markdown, which I like. But what I also really like is the ability to easily interlink between docs, which is so huge.

When you're writing up a new KB doc, got to be able to easily link to the related feature over there. And that was a little bit clunky. So

I like seeing this thing happen that you're alluding to where you might launch a look at HelpScout for a sec, right? You're launching a shared inbox for support. But then the way customers actually use it is so closely tied to knowledge base that all of sudden you have no choice. You now have to run two products in order to compete because as soon as you link them together, it becomes so much more valuable that if your competitors put them together and you don't, you'll lose every comparison. We saw that with recharge and subscriptions.

And then right next to that, what developed was a customer portal because shoppers want to be able to go on and change their subscription. And now every subscription product needs to have a customer portal. And we are actually encountering that they also have to have a hosted checkout to capture the payment. They're dying because it's too much surface area and they're looking to us to outsource the checkout. It's kind of funny.

Yeah. That's interesting.

Yeah. Yeah. Like, you know, you get a you get your product and you get pulled into potentially something very, very closely adjacent. You feel like you have no choice but to do it.

Yeah. Yeah. Totally. The the key piece there also is is the beacon in in the app. And HelpScout has this.

HelpSpace also does a good job of this. So that's I sort of intentionally don't do live chat support, like intercom.

You don't? I like it so much.

I mean, I definitely get the benefit. I've seen the benefit in previous businesses, but I don't like having it there if I'm not gonna be live all the time and I'm not staffing it up. But I really like and I think it's important to offer a beacon where someone's in the app, they need help on this page, they can click here and and get the doc, like, embedded in the app. Yeah.

There you go. A third product for a company like that. Now you need to input notifications in.

What do you do on metrics? How are you tracking everything and reporting and what are you looking at?

So, okay, I'm looking at a product called Grafana. Have you heard of it?

I have not.

I think it's G R A F A N A. Yeah, Grafana, open observability platform. So this is what our engineers take. And I can say, I would like to see a list of merchants, how much they've processed, how much of that is checkout revenue versus post purchase revenue, what their domain is, and be able to cut that up. Last twenty four hours, last one hour, last seven days.

I want to know that. It tells me growth. It tells me if someone slipped. If I look at the past thirty days and I see X number of merchants have processed revenue, and then I go over the seven days and it's much lower, consider myself, Okay, who dropped off? So that Grafana is what allows us to create a visual layer for nontechnical people with all of our data stuff.

Yeah. Man, this has been such an ongoing running headache for me is getting the metric tracking and the tools set up in the way that I need them.

This is internal for you or for the customer facing it?

No, internal. Okay. Internal. Just seeing what's what's going on in the business. I I feel like a year and a half in, we're finally in a in a better place in terms of, like, being able to collect the right data and report it.

And it took a surprisingly difficult road to get here. Everyone loves to say like, oh, just use this or that tool, plug it in and quote unquote, it just works. Like, I'm sorry. It doesn't just work. Like, it it requires code.

It requires crazy integrations.

Okay. So You're never a 100% sure if it's accurate.

You're never no. And that's a big deal. And I'm not just talking about the edges. I mean, things can be way off. And some of these tools, well established tools, have pretty surprising gaps in their features that can cause some issues.

All right. So we are now today using so I still have ProfitWell plugged in, but I'm mainly using ChartMogul for just tracking SaaS metrics. I think it's a great tool, fantastic interface. We had a lot of road bumps in getting it to report the way that we need to, especially since we're freemium, which Chartmogul had some issues supporting. But their their customer support has been incredibly helpful, like really technical in in the trenches with us, and that's been great.

Mixpanel is the other one that we use. Their their customer support is also very technical and very, very helpful. Even I I've since upgraded Mixpanel, but even when I was when I was a totally free user, they were giving me some serious like, they spent hours on my support tickets. It was pretty great. And that's that's I think I'm really impressed with Mixpanel.

The alternative on that one would be Amplitude, which seems really good too. I got Mixpanel working and it's one of these things that's like, man, I spent, I've invested so many hours, like we're You not

don't wanna touch it.

That's right. For folks who aren't that familiar with this stuff, use case for different tools. You probably need one to track your SaaS financial metrics. And that basically comes down to Chartmogul and ProfitWell. There's probably several others out there that are worth looking at.

But so SaaS metrics like MRR, churn rate, trial like conversion, all this different stuff. And then Mixpanel and Amplitude are used for event tracking and usage and how active users are and what types of activities are they doing and conversion through your activation funnel and things like that. And in both ChartMogul and Mixpanel, we did a ton of work to be able to segment. This is where it gets really dicey and time consuming to really get the reporting right is so I finally got it to a point where I can break down all of our graphs based on source of the customer or based on the customer's use case for Zip Message. You know, I can see, like, if they're a coach, how are they converting compared to if they're just a team user?

Or if they came from a Google search versus if they came from an affiliate link. Like, I can see like, I could break it down that way in both Chartmogul and Mixpanel. On the top of the funnel, like the traffic, still have Google Analytics installed. I still have both the Universal Analytics and the GA four installed. As many people know, Universal Analytics, like the Google Analytics that you have known for many years, that is going away in 2023.

They're shutting it down. So they're moving to Google Analytics four, which is a piece of shit, just for the record.

Just be blunt about it.

Look, it's it's just terrible. I'm sorry. Like, I've I have gone really deep on it. I tried to learn it. I tried to, like if this is the future, then I get then I need to learn it.

I I did all that. It's it's terrible. The interface, the way that they track, it's just I still have it there just to get the data, but so I just recommend install some other tool probably sooner rather than later so that you're not missing out on history. Fathom Analytics is a really great option. I I actually ended up, unfortunately, guys, if you're listening, sorry.

I I went with, I got Plausible installed because they're using ZipMessage too. I got into a Oh, cool. A good conversation with with those guys. And they they were also very helpful in debugging some of the installation issues. Both of those are really, really good

tools. I was going to say, Jack, that is a very good reason to go use your competitor when they're an actual customer of your software. And this is actually Jack's, Jack Ellis, we're talking about his question about the tech stack. So he and Laura Roeder are gonna be pumped that we spent the entire podcast on this.

I should also mention, we've also built a lot of tracking in our own database and our own app and and like internal dashboards on stuff. Like, we're tracking stuff that is important, like, for us. So like like number of minutes recorded per per account, like average number of minutes recorded, average, you know.

For the things that are uniquely step message.

Yeah. And and also, like, we we have a viral loop, so we have to be able to track, like, for every user, how many other accounts do they refer on average, and And then how many of those accounts convert to paying customers? And so that's a really complicated logic to be able to track, but I think we finally nailed it down.

Very cool. And look, we have to give a shout out

to the GOAT,

the absolute best tool of all, Slack.

Slack?

Best. The absolute

What? Like notifications?

No. Just everything. I use the hell out of Slack. Oh, yeah. I just admit that I live in Slack and I have started to just go with that reality.

And so I have channels set up for, let's say for all hands. So we do a monthly all hands and I want to make sure I highlight certain things there. So as I see things happening in Slack, I'll just copy a link to that conversation and I just put into an all hands channel. And then when I go do slides for all hands, I have a whole bunch of stuff that happened throughout the month that I can highlight. I do the same thing for investor updates.

We brought on a business admin partner, which is like a super admin basically. And she and I have our own channel that I just put in random thoughts. And then next time we have like a work session that we're working together, we just go there. I've just outsourced memory to Slack. Everything that I wish I could remember, I just put it, I just have a place.

That that's what I use Notion for. But because, like, Slack, if I throw it in there, like, it's probably going to be forgotten for me. And and we we definitely use it for day to day chats and quest and quick questions and, like, updates. I made it clear with the team in audience ops and now again in ZipMessage. You know?

If it's a question that requires, like, an a a real action from me or someone else, just make make it like a comment or something in Notion or send a zip message where it's like where ultimately, I I want that in my email inbox. Like, if it's if you need something from me, send it in in in Notion so that it's logged in where we're tracking it or reply to the zip message conversation because that will send me an email notification, and then it's in my inbox, and I'll deal with it in time. If it's Slack, I'll see it when I see it, I might lose it.

I have an easy time when it's things like all hands. I know I'm going back to that channel. I don't have to think about it. But sometimes I abuse the mark as unread. I abuse that feature in Slack to make sure that I don't something doesn't disappear.

And sometimes the mobile app is not as reliable as you want it to be. Sometimes you open it and look and something will highlight bold at the top and then disappear. I'm like, shit. What was that? I'll I'll never see it again.

See if

there's anything else that I'm sort of forgetting about. Like, have a lot of like little tools that we use for stuff, but those are like the big ones, I think.

Alright. What other what what else we got going on here?

Yeah. Let's get to the other stuff.

All right. So John Dougherty, our friend at Credo asked about funding and what's changed and more specifically like hiring ahead of revenue versus behind revenue.

Yeah, and a little bit of like hiring when you're bootstrapped versus when you're funded.

Yeah, because some of the other questions are also in a similar vein where they're asking like when to hire your first hire and in what area should it be? How to know when to hire a CFO to keep track of that? So a lot of it comes out of resource constraints. When should I move on from the multiple roles that I'm doing to hire? Should I hire someone for something that I'm good at or what I'm specifically bad at or what I think is most important or least important?

All that stuff.

All right. So a lot of sub questions under hiring here. Let's start with the one like, who do we hire first in the business? That is so an it depends question. I think if I had to boil it down to one piece of advice, or at least just in my experience for me, it's been the first hire has always been the person who helps make the product happen.

In audience ops, the very first hire was a writer. It was actually I actually hired three writers at at in the very, very beginning because the product is we write articles. So we need writers. Right? Like, the business wouldn't exist without that.

So I I started there.

That's an interesting reveal of of a bit of bias because you assume that you can just you can just get customers because you have that confidence. So you're like, I'm not gonna have a problem getting customers. I have a problem on the delivery of the product. That's I my

guess it's a little bit more like my circumstance at the time and the type of business it was. Because in general, like, if I'm if if we're literally starting from nothing, if I'm just like a freelancer and I'm trying to start a business, then then probably that first product creator is gonna be me, myself, and just hustle and do it. And and I that's actually what I did on Zip Message. Zip Zip Message was I'll say, like, the first hire was was my developer, but it but the circumstance was that I I still owned ProcessKit, and I already had a developer relationship actively working on ProcessKit. And what I did was he was maintaining and working on ProcessKit while I went off and did a little side hustle project building the prototype for Zip Message.

Like, I did that myself for about a month. And once once I was like, oh, there's something here, then I pulled that same developer off of ProcessKit and had him start working with me on Zip Message. That's sort of how that started out, I guess.

Yeah. I think this is what John was asking about, I think, is where there's like a the first split in the road is, are you bootstrapping versus taking outside money? And that has a black and white impact on how to think about hiring, who you're hiring first, and so on. So at Cardhook, guess I had the option. I had some budget to work with, but it made no sense to just start burning money.

So it was, let's get a product done first and then let's go try to sell the product. And then it's almost like this real time adjustment based on what's necessary. So, okay, now you have customers like, uh-oh, we need customer support because Or after that or before that it's success or something, someone to work with the actual customers unless you want to go work with the customers. And then you have to think, well, I still need more customers. So now I need marketing or sales help.

So it really feels like it is like very reality based. What's happening now in the business and what it needs and what it might need a little bit into the future? Whereas the funding path is kind of like, well, how do we build a machine that can grow quickly and we can't really mess around. We can't spend much time waiting for certain things to happen before we hire the people and put the things in place.

But it

feels like much more of a rush.

The interesting thing about customer support hires for me has been Audience Ops was weird because it was like a productized service. So I definitely hired a lot of account managers who are probably the equivalent of a customer support rep in a SaaS business because they're customer facing. So let's put that aside because it's more of a service business. But Restaurant Engine was really like the last time where I actually felt the pain and the need to pretty quickly in the business hire customer support reps to handle the influx of emails from customers. In my opinion, that comes down to like the nature of the product and the market that you're selling to.

Like, restaurant owners were just so much more needy in their support needs, and it was like a low leverage support response. Like if I'm the one just handling the support, it's like, how do I reset my password? It's how do I do these basic things? And I'm not learning a lot as the founder by doing that every day. So I needed to get it off my plate.

But like fast forward to ProcessKit and then ZipMessage, which both of them have had hundreds of customers and ZipMessage has that plus many thousands of free users too. So like, I'm kind of surprised at how little of a pain the customer support burden is. I don't feel the need to hire a support rep in the near future. There definitely is customer support questions that come in and I handle them, but the vast majority of those for me are totally insightful. Like I need to get them.

I see patterns in those.

Right. You don't want that siloed off completely.

Yeah. And a lot of them in the earlier days have been like, there's a gap in the product here. There's a gap in the product here. There's a gap in the product. And I kind of needed that.

Yeah. We're waiting on support also. We didn't have someone in support or success. Basically, it was our salesperson, biz, dev, do everything person that did the support also. And now success feels much more it feels like it needs to come first.

That is the nature of our sales process. At Cardhook, we were doing free trials and the volume was so high that we had to have support as soon as possible. That was actually the first hire outside of the founders and the founding team. The first person was support because we couldn't get away. We couldn't think.

We couldn't spend our time on anything other than support.

Yeah. Like marketing hires, I would say I'm definitely hiring more in that area for ZipMessage than I have in previous businesses. And I think definitely hiring in general, both on product and marketing, and I actually just looked at it yesterday while I was preparing this talk, like, I'm spending, like, almost double on marketing expenses, people and marketing spend than I am on developers right now. Like being even a tiny bit funded definitely has an impact. Probably wouldn't hire this quickly if it wasn't for that.

Yeah. We've talked about before, like the staircase looking graph of hiring that we had at Cardhook where was always willing to hire a little bit of head of revenue, but not too much, and then let it catch up, hit profitability or very close to it, and then take the next step up. That felt appropriately stressful. It was like, well, we want to push hard, so we're not going to be fully comfortable. But we're not that far from course correcting back toward profitability.

Rally feels absolutely insane comparatively. And one of the biggest mental challenges for me was to get comfortable with how uncomfortable it is to spend that far ahead of revenue. And it feels nuts.

That's where I am too. Even on a different level in terms of funding from Rally, this type of mindset is definitely new for me in Zip Message. In previous ones, Audience Ops was basically profitable the whole way through from start to finish. All the hires came at it was a productized service. So there was almost every single hire was kind of attached to a piece of our revenue.

We have clients who pay x and that funds these roles to serve those clients. And and that's really the model there plus profit. Yeah, Zip Message is still in startup mode. We're still burning through a runway. So yeah, it's definitely a mental I was probably slower in the first eight to ten months of Zip Message to like, I was basically still operating like Bootstrapper, and it it wasn't until almost a year end that I started to like kick the spending into gear, being more okay with spending ahead of profitability.

Yeah. I know if I'll ever actually get over it after having the bootstrap profitable mindset for so long. And it's a little bit of the impostor syndrome thing attached to the spend because I remember the way I thought of people in my position now. And you've raised a bunch of money and you start spending it, a lot of it. And it's all relative because I look at my competitors and I'm like, you raised a billion dollars and you're burning through money.

But in our own way, we're doing the same thing. And it kind of doesn't matter as long as you manage to get to the goal. The stress

of it

is very, very different. And what I really don't like, but it is an inevitable reality is that you are always thinking about financing. You're always thinking about when do we run out of money? What do we need to do to raise more money before that happens? What do we need to do today so that we're in a good position by then to raise more money so that we don't.

The way I would describe it is it feels like an inevitable march towards success. The only thing that can stop us is running out of money. That's

how

I honestly feel about this business. And running out of money just looms very large in my mind because I'm like, that's the enemy to vanquish.

Yeah. Yeah. For anyone running a productized service business, I know some of the people listening might be. I just wanted to speak to because I'm not running this type of business today anymore, but when I was, I definitely learned a few things like the hard way when it came to hiring. I wanted to share it real quick.

So again, this is specific to a service based, like a productized service type of model. I think SaaS is different work. But in the service, the more that you can tie the spending on whatever contractors or part time employees to like a variable that goes up and down with service load, the better. What I mean is like early on, we were growing a lot, and then I converted some some of these variable contractors to full time salary employees. And then when our revenue graph got pretty bumpy, it it got pretty scary because, you know, the the expenses stayed the same.

The advice there is and I also don't advocate for paying by the hour. I much prefer like, I like to sell a productized service, and and I like to buy services like a productized service. So a lot of the contractors that I work with, even still through this day, I like to just agree on here's a monthly retainer, just a set flat fee.

Right. Here are the expectations.

And here are the expectations. But in a service business, I like that flat fee to be per deliverable if if possible. So, like, every widget that we service involves this, this, and this. So every person that I hire to do this, this, and this, we we agree that, like, $300 per this what we're going to pay. It's just a question of how many of those widgets you're going to service every month.

And you want to go up and down. You want to be able to ratchet that up and you know, because that's the other big learning with a product type service as you get into these higher price points, like higher revenue per account. It's great because you can grow a really fantastic recurring revenue business very quickly with just 10 to 20 to 30 customers. The downside is that churn can take some wild swings. Yeah.

Big swings. Could you could, like, lose three customers in a week, and you just churned, 10 k MRR. Like Right.

And and then and then shedding one or two people on the team is not easy because you've trained them, you like them, you want to keep them, all these other, that's when it gets tough. It is important to acknowledge that labor costs are determined by the business. Like you get to decide how much you're spending on labor. It's not like Europe. American companies can really just decide to just cut workforce.

You don't need all these reasons and that much time, which is important for the business. But that does not mean that it's easy and it does not mean that you'll actually have the stomach to have those swings or that you'll conclude that it's smart to do that because it also hurts.

Yeah, It absolutely does. And I mean, that's why in that business, the service business, we really optimized the whole business around hiring people who are not only comfortable, but they seek out roles like that. Like they want to be freelancers with a really steady high quality retainer. And that's what made that really work well. Yeah, clear trade off.

Cool, man. Well, we got a bunch more questions, but I think we're out of time. It's Friday, I got a few more things to finish up before I call it a day. Don't if you got any good plans, but enjoy the weekend.

No, I'm just going to hang out and then I'm going to head out to Colorado next week. I don't know if we'll be able to record next week, but I will be back on Friday morning, so we'll see. Okay, Cool. But, yeah.

Thanks for listening.

Thanks for the questions folks. Keep them, keep them rolling in, you know, get us up on, on Twitter and, then we'll actually know what to do on this podcast. All right. See you later folks.