Bootstrapped Web

Welcome back, everybody, to another episode of Bootstrap Web. Brian, good to be with you on a Friday.

Jordan. Good to be back. Yeah. Should be good. Alright.

So what do we got? You're you're in Chicago again. You're you're settling in.

Getting settled in. I've only been here for like a week. So it's been been a bit of a whirlwind, but I got myself set up in a co working space. Feeling good, kids are in school. Feels good to be done with this week.

It's been it's been busy. That's how I feel. It is my favorite when it feels like that, when it feels a little chaotic and I'm leaving the office and I'm like almost like a little out of breath. I'm like, oh my god, what just happened? That I think that's my favorite spot.

Yeah. I mean, I think work for me is always kinda chaotic, but we're just finishing up the summer. The kids are starting school on on Monday, and we just did a quick trip half of last week. I just love Airbnb. Like, just as a I I can't believe this is, like, part of our world now.

Like because we were able to just go drive three hours Upstate New York and get a get a lake house. We we wanted to hang out at a lake house. You know? Get a house on a lake with a couple of kayaks and canoes and hiking, and that's what we wanted to do for a few days. And we spent a few $100, and we can go do that.

When we were kids, to to be able to do that, we would either have to own that lake house or have a friend who owns that that lake house. And that's it. You know?

So only two options.

Yeah. So that was

But kinda

but we're we're done with the the trips for a while. I've got a couple of business conferences coming up. But, like, other than that, like, from here through the rest of the year, it's it's heads down work mode. I can't wait to I've got a lot coming up in zip message land, and I can't wait to just really dig into it.

I feel the same way. I think it's partly calendar, you know, like summer ending, and starting school and whatever else, but I feel so happy about being able to focus on work. We left our house in mid July. So it's been six weeks of running around, working on a laptop and all that. And man, it feels great to just be locked in.

It's great. Cool. Well, we got a lot to talk about. So we got a lot of things to cover. Where do you want to start with, man?

The big thing that's been on my mind and what I'm working on every day, this has been all summer long now, is a deep dive on customer research. I've been doing a lot of customer interviews and logging them and learning from them and and using them along with a lot of other data points and and things to really solidify a big new direction in Zip Message. I'm really thinking of it as like a next big how to describe it? Like, it's not a rewrite by any means. It's maybe Zip Message two point zero is the wrong way to put it.

But it's like a big next iteration of the product and the and the marketing focus and the target customer. Yeah. We're we're building on on what we've had. So anyway, that that's one big topic that I wanna talk about. And the other one is this idea of running and working on multiple tracks simultaneously and managing that, trying to stay sane, trying to have like mental models around that.

I can just share a little bit about, because someone asked me this week about, you know, how does one thing that I worked on kind of contribute to the bigger picture direction? Which is a great question. But the answer is that, well, it's just one thing and there's actually a lot more that's going on just on very different timelines. So maybe I would talk a bit about that. Anyway, what do you got?

I got a little bit of personal moving to Chicago and how that's kind of impacted me. And it's closely related to professional, but it's just like one of these topics that I think all of us deal with in terms of like motivation and where it comes from and how your environment shapes it. The big theme on the business side has really been around people. And what I mean by that is hiring resignations, building up teams, building up the organization, trying to figure out who we need in place, how do we find them. So it's been a lot of like, that's been my big focus.

So those two and just how they relate to go to market and bringing in customers and getting them successful and happy.

Yeah. Well, where do you want to start? Why don't you start with one of those?

Yeah. Well, I'll start with the personal. We got here to Chicago like a few weeks ago. We stayed for a week, then we went out to the Hamptons and hung out for a week with my family and then came back here. So we've been here two weeks out of the last like four weeks type of a, you know, kind of an odd thing.

But moving here and just starting to settle in, what I found is that the the environment has a very, very big impact on the conversation I'm having in my head around ambition and money and business and that soup.

What do you mean by environment?

Okay, so we left the New York area and like that very intense, like Westport, you're familiar with it, but maybe, you know, other people aren't pretty intense environment in terms of like money and how showy it is and all that other stuff. We didn't like the direction that was going in. An important element of that was the environment didn't feel that healthy. You know, 18 year olds driving $100,000 cars is kind of like, all right, I get the point on what's going on here. And we decided that that's not our preference to live in a place to raise kids.

Yeah.

So New York.

There's a lot of that around New York and Westchester and parts of Connecticut too. Yeah. Yeah.

Yes. And look, part of it is ego. And part of it is not liking being around people that I feel are more successful. And so there's definitely like that insecurity ego stuff that happens a 100%. We moved to Portland and one of the things we loved about Portland is that we felt none of it.

We lived in like this nice area and there were barely even like luxury cars. So you get a beautiful house and a Subaru that's five years old up front, you know, and we were like, oh, that that feels healthy because people focused on how nice and good of a person are you, not what do you do for a living? How much money do you make? How fancy is your stuff? So we love that.

The the issue with it is when I was in that New York environment, I had a never ending source of ambition and energy because you're literally surrounded by it all day, every day, and it makes you wanna strive.

That's true, especially when you live in the city. I lived in Brooklyn and Queens for multiple years there. And, yeah, just being around that environment does give you that energy for sure.

Yes.

Yeah. But, I mean, Long Island and and then we were in Norwalk, is right next to Westport in Connecticut. You're you're right. Like, it's what I've seen in growing up in Long Island just like you, you know, like, yeah, there's a lot of money around. But especially as I'm getting older, like, the value just seems like so out of whack.

You know? Like, everything is way more expensive than it even should be in terms of the quality and the and the quality of life and all this different stuff. But like people still

They just do

it. Live there.

It's And

all that, you know? Yes, yes. Yeah.

So in Portland, that didn't exist and that felt like a healthier culture to live in and raise a family. But I didn't have didn't have very much of the external stimulus that created ambition and striving. I still have it, but it was like internally generated. Like I conceptually would be sitting behind a desk at a computer and thinking about, I want to be successful, I want to be ambitious. I'm looking at Twitter.

I'm talking to friends. I see what other people do. But it wasn't like in the environment, like around me. And coming to Chicago feels like this in between because, you know, we moved to this town, it's beautiful. And some of the houses are jaw dropping.

And so I am getting that stimulus that I used to get where you just you can't help it. At least I can't help it. I just now I want more. I'm just I feel that energy to strive again. But the Midwest element doesn't have the same edge where New York kind of whispers like, you poor bastard.

It kind of like points at you. It

does seem like there's a lot of like faking happening in New York, whereas Chicago and the Midwest is a little bit more real.

Yeah. A little off the gas and less in your face and less aggressive about it and all those things. So it's been an interesting experience to just kind of feel that stuff and acknowledge what's happening internally and like, okay, you know, how do I use this in the right way, in the way toward the light and not toward the dark? Because I can go in either direction. It brings me, it forces me into like these reactions and the conversation I have in my head, how I feel about myself, all this stuff.

So I feel like I'm now starting this process of like settling into it and working out in my mind, like, how do I feel about it? What's my interaction with the environment? How am I going to let it create the ambition without the resentment and anger that that I used to, you know, characterize it

with. So what I'm hearing is in Portland, you were you were in an area where there's just like a mix of of what you see in terms of, like, value of of real estate and cars and lifestyles and

And people.

And and and like the culture around that. Right? And you're you're now in a suburb of Chicago with you're you're visually seeing, like, beautiful homes.

Yes. Like, that's back.

The visual. And and that lifestyle that you weren't, like, visually it wasn't like on your block when you were in Portland.

Yes. Not nearly in the same way. It's just like a different thing.

And I see it here too. Like, and we moved a little bit further up into Connecticut, which is a little bit weird because the property valley like, the the prices go way down, but the houses get huge around here. And even we live in a in a in a property that, like, I never dreamed we would have this this much land, like, for for such a low price. Right? Yeah.

I like, I'm around it too. Just on my block, there are million dollar homes, you know, and it's like, I don't know that that, like, it's that big of a change or a shift for for me in in in the areas that I've and and the and, you know, the people that I that I hang out with. I will say, like, one one thing that maybe this is sort of related. So last week, a couple of longtime great friends of mine that I that I grew up with, we got together and went went to see Rage Against the Machine at Madison Square Garden.

Cool. That's fun.

Amazing. Which by the way, we had those tickets since 2020, and they finally did the show this year.

Talking about that. Oh my goodness.

Amazing show. But, you know, we we had dinner beforehand and everything and, like, just hanging out with with with my friends. Everyone's, like, doing well in their careers and and making a lot more money and and, you know, you know, buying amazing homes and all this stuff. And, like, actually, I'm not the only business owner in in the group, but, like, the only one really doing what I'm doing, which is, like, software startups online. You know?

The others are either in jobs or brick and mortar businesses. Right? There is always this feeling of, yeah. Like, we're very comfortable right now, and I've had some wins in businesses that afford a a pretty good lifestyle right now. But the actual salary is nothing compared to what most of most of my peers, especially those who who don't own their own businesses are are making in in their in their high salary jobs.

Right?

Yeah. It's almost like at this age, it's it's pretty stark. It's like, yes. If if you were willing to go that route, you do make more money. It's kind of pretty straightforward.

You don't have the opportunity to make, you know, tremendous money, but you cruise and keep going higher. And Yeah.

And you can invest it wisely and Oh, yeah. But we own our assets, you know? And that that's the thing that keeps me going. That that keeps me unemployable really is is that I own my own thing. And and what I'm building here is an asset that that will result in a in a in a much bigger win down the road.

And maybe down the road is just a few years, maybe down the road is many more years. But for me, it's also a lot about my current lifestyle and the freedom that it has, not just working remotely and everything, but getting to choose what I what I work on and the type of people I get to work with and and all that kind of stuff. Right? That that all folds into the value prop of of all this, you know.

I had difficulty with it in New York because I was in finance. My friends were in finance. And then I went toward my own business and being an entrepreneur. And at some point, around, I guess, 30 years old, my friends were making a shit ton of money. And I had gone the entrepreneur route and was quite happy about it.

But I started to have a pretty difficult time, like like in terms of like my ego and how happy I was when I go hang out with my friends and I was in the struggle and I was trying to build a business and I wasn't making anywhere near what they were making. What it did is made me uncomfortable about the decision that I made and made me start to look back at like, maybe I shouldn't have done it. I was like, is stupid. That's external. I'm happy doing what I'm doing.

Why should I allow myself to be unhappy in comparison to other people instead of just finding your own path? And that made leaving and really going out on our own feel great. And we started traveling and then all the happiness bubbled up and then success came with that happiness and it felt amazing. So it's interesting to kind of come back into the fold a little bit, right? Last night when you go back to school night, there are five people there that were walking around with that I went to school with in Michigan.

So we're back in the fold of those same circles. Yeah, it's true.

You guys are much more socially networked than than we probably are here. I I've got a lot of friends and that I've grown up with, you know, from New York and everything and and family and stuff, but then a a whole group of friends online on the Internet, you know, our our our circles who who are running running businesses like this. And it's such a night and day difference when, you know, when I'm out to dinner in in New York with with folks who aren't doing software startups. There there's just, like, zero material to kinda commiserate on. There's a lot of other stuff.

But like, for for me, there there's there's a lot of that energy in inspiration ideas, which is all positive. But there's plenty of the negative stuff of like, man, friends that I've come up with in this industry where we were at the same level a few years ago have multiple times surpassed where I'm at with my stupid MRR graph. Right? And you you can't get away from that kind of shit.

That's right. That's right. So it's an ongoing effort. So that's that's been a big thing that's been on my mind. How about you?

What's going on?

So I've tweeted about this multiple times. I've talked a bit about it on on the podcast. This summer, I would say, has been a deep dive in customer research. And, you know, let me preface this by saying, like, Zip Message is is is doing really well. We actually just surpassed a pretty big milestone.

I don't wanna talk numbers, but it but it's it's a good one. But I I still don't consider what we have today to be quote unquote product market fit. You know? I think we're I think we're close, but we're not there. There there are definitely signs that, like, it it has not fully clicked yet in a in a way that you would expect SaaS to click and and hit product market fit and grow.

That has driven a lot of effort on my end to do to to understand what what do we have here? Because we do have something. We we get plenty of sign ups and plenty of paying customers every month, and there's plenty of churn too, just to be transparent about it. My task this whole summer has been to let me understand this as best as I possibly can. You know?

And Zip Message compared to all my previous businesses has been so different and so weird in so many ways. There are so many SaaS out there, especially in our bootstrapped SaaS circles where you start with an industry and you're building the solution for an industry. And and you know mechanically how to like, what you need to build to solve a problem for some industry and you build that software. Zip Message, as you know, you've been listening to the pod. Like early on, it was basically just like an idea that I threw at the wall among several other ideas.

And it sort of just resonated with some people. And I had some ideas for use cases for it, but it was sort of wide open. It was very broad. And for the whole first year, it was super broad and it was growing. That, I think part of that helped it grow.

But also what it resulted in by the time we got to 2022 was what I actually believe is kind of like a one feature product, really. Like really ZipMessage, if if I'm honest about it, we've built a lot, but we've built a lot around a single feature, and that is the video and audio and text asynchronous messaging thread.

Is that like right. Features almost like not good enough because you have a lot of features.

We have a lot of small features that that all contribute to the same task, the same thing to do, which is a messaging thread with someone else or or the group. We built a lot of the core during the first year. And then into the second year, we started to just keep improving that that feature. We, you know, we improved our recording interface. We improved our reliability.

We improved the speed. We improved we're close to shipping now the ability to edit your videos, which is another feature, but it's still part of the same thing. Recording, editing, and sending. And it was a little bit of like, I didn't know which direction to build toward. Who who are we building for?

That was always a really murky question. Right? So, all that's to say is I, as I've talked about, I I've dove into doing a lot of jobs to be done interviews to better understand the people who are using Zip Message, the people who are really happy paying customers, also the people who have used it and then they churned. And I've also interviewed people who fit some profile that that have never even used Zip Message. So far, I've done 30 plus interviews.

And I did a round back in June, which would would, I would say, were really jobs to be done interviews. Like talking to many different types of users and really understanding the goal of that round was to figure out who is the best customer. And coming out of that, I did learn that coaches, like professional coaches are the best user. And even going all the way back, I think I talked about this on Bootstrap Web in early twenty twenty one. Very early on when I just launched Zip Message for the first time, I felt like I needed to niche it down.

That's the playbook. You're supposed to niche it down. Right? And my thought was like, I think coaches are are using this more than others. I think I should niche down.

And I decided not to at that time. And I decided to stick with horizontal and and then grew it from there for for a year plus. And and then the interviews in June sort of confirmed that original hunch that, yes, in fact, the customers who who are, according to metrics, are the best customers. They are the the people who are using it for some form of coaching. There are con consultants too, and there there's a lot of overlap there.

That's what came out of the June interviews. Then here in in August, I did another round of like 15 plus interviews only with coaches. Just talking to to our customers who are coaches, talking to other coaches who I was introduced to, to really go deep on like, okay, well, if coaches are the best user, what can we do to make this product even more valuable for them, more sticky for them, and really solve what they're trying to do? And it and it definitely became clear. I won't get into all the details, but there are some pretty big jobs to be done things where where coaches are definitely stringing together, duct taping together multiple tools, us plus two or three other tools that they pay for that aren't meant for the thing that they're trying to use those tools for.

And and that's pretty clear.

Coaching's a relatively developed vertical at this point.

Yes. It is a vertical, but I would say coaching is actually even larger than I thought it was. When we think about coaching, a lot of us think of like business coaches and executive coaches and leadership coaches. There's plenty of those. And we see a lot of them in in ZipMessage.

Then then even just even within the business realm, you have a lot of sub so you've got like sales coaches, marketing coaches, branding coaches. Then you've got consumer coaches. Like life coaches, nutrition coaches, health coaches, fitness, guitar teachers, language coaches, speaking coaches. These are literally all customers of Zip Message. Like, people have found Zip Message, and and they come from these industries.

So there's more to do there.

There's a lot

more to do And

I'm and and and, you know, I've dabbled in coaching with with my productized stuff in the past, but I've never really been a full time professional coach. I'm talking to all these people, and I'm really understanding what what do they aim to do? What are they doing? What have they done? And what are the what are the tooling around that?

And so what this means going forward oh, and the other thing I wanted to talk about is these customer interviews are incredibly insightful, illuminating. Like like, they keep saying the same things and using the same words. And and Claire on my team, and we're we're going through these recordings. We're doing voice of customer, you know, analysis and all this different stuff. That's amazing.

But for me, what what gets really exciting is corroborating that evidence with other evidence. We get a reason for for why they cancel. So looking at all the reasons that people type into that form. I also get a lot of presales questions. Before they even sign up, like, they're they ask for certain features.

Right. And you're starting to see all these things like

Yeah. And and then you see like support tickets. Like, how can I integrate ZipMessage with with that because I'm trying to do this? And I see literally the same questions come in again and again and again, specifically from coaches. Other people don't ask those, but the coaches do.

And they and they are the best customer for us. And we actually see a lot of customers who come in, try it, and then pay for it and then cancel because they were trying to do the same thing as 10 other people.

Right. Didn't quite get them there.

And then there's another thing where it's like, they were trying to do this thing. All these different customers were trying to do this thing that we don't even advertise that we are for that. They were just trying to do that. Like they were trying to fit us into this use case that like, we don't even have a page on our site about that.

Right. They don't need you to get there. They just need the breadcrumb and they're already going to where they wanna go.

Yeah. Yeah. And so that what that leads to is we need to build more more features. We need to adapt what we have in this direction. And this is not I I don't think that this is gonna become a disjointed beast of a of a do it all product that that has 15 different features that do different things.

I really think that we have an opportunity just looking at all the all the there's there's a lot of different competitors and alternatives that people use. Some are coaching specific, a lot are not at all. We have this angle where we are for asynchronous messaging conversations back and forth. And there's a lot of other types of interactivity that coaches look to do when they're communicating with their clients other than just sending and receiving a message. Like a lot of them need to send an assessment form or, or deliver some course content or deliver a worksheet or or give them their their template checklist for this or that.

Like coaches have a library of things that they pull from and insert into their conversations with clients. You know? So that's a big direction that we're building into running group coaching is a big thing. Group cohorts and things like that. So there's a lot that we have now on a roadmap that is clear.

And I feel pretty damn confident now having done all this research. And it's like now for the first time in a while, we actually I actually know what product we need to build. Because because before, it was all about like, let's just make this really cool asynchronous messaging tool, which is a which is a cool one trick pony, but it's it's not a a proper product that solves a big problem that is super valuable for people who build a business this way. So I'm pretty excited about it, but it's a long road ahead. And then the question, and so now is like, how do we actually execute on this?

I want to avoid going into a cave and building it all and then launching it a year from now. So it has to be incremental. And there's a long list of things that we need to build and features that we need to adapt and refactor the UI in different ways to fit this direction. But we have to be strategic about a, building the most important things in the right order and b, designing them in a way that doesn't disrupt our current users and then rolling them out in a in a incremental way, you know?

Right. So people get value along the way instead of wait waiting until it's done.

Yeah. And like, so just this week after months of research and really understanding all this stuff, like I'm finally like actually opening up Figma and designing like, is, are these changes going to look like, you know? And I think the current zip message is really gonna stay as it is. The current zip message is essentially in simple terms gonna be the base plan of what we have. And, and all this new stuff goes into the middle plan and a new upper plan and that's sort of where it's headed, you know.

Cool.

Well, I like it, it feels like you've built up the confidence in the right way to make the bet in this direction. Right, that's effectively what it is. It reminds me a lot of the same conversations that I had, the same messages that I read, all of these different things when we made the decision to build the checkout product after running a abandoned cart product for two years.

You and your experience with CartHook, see, this is what I do when I reach out to friends and advisors for advice. Really what I look for is like, can you share any experiences in your past that have any sort of parallel to what I'm what I'm faced with today? And and I have several friends who Everyone has a completely different path, obviously. Everyone has different variables, different realities on the ground. But this is what I look to when I when I seek feedback.

And and looking at you with Carthook, and you're definitely one of the case studies that that I had been thinking of where where you had the checkout product, the abandoned cart product for what, a year plus, right, for two years. And then and then it was like, there's this bigger opportunity. Right?

Right. But the the the matrix, that view of understanding all these different parts and how they come together took a while. And then at some point it's like, oh shit, I see something that I have confidence in that not many other people see, and that we're in the right place to take advantage of. And then it gets to a place where, okay, I'm willing to make that bet. I'm willing to take the risk of foregoing other opportunities, other niches, other things, because, right, you get to a level where you've spoken to enough people, you've read enough things, you've got the cancellation, the support, all these different pieces of information.

And you're sitting at the top of that with the view that's good enough to take all that together and say, Okay, I got it. Now I know what the market wants. I got it. Let let let me let me get going.

Yeah. Yeah. It's true. It it does bring a sense of relief to, a, know what the roadmap is and what we're building towards and just just put the resources in in place to execute on this and make a plan and prioritize and all that. Yeah.

Now I know what I can say no to. Because before before having this clarity, I would get feature requests all over the place. I would I would get different marketing opportunities and things that wouldn't necessarily help us achieve any specific goal other than bringing more random users. And now now we have a we are executing a lot on marketing, but now it's all pointed in the same direction. Know, now it's all and there's a lot more that we haven't even launched yet in that regard.

Yeah. So it's actually a perfect transition to my side of things because what you're talking about is very important and essential, but not enough. Like now you need to execute properly. And that doesn't just mean building what you're supposed to build. The order of how things should be built and who to listen to most and how do you provide value along the way so people can pay you over the next year and get value out of it?

Because it might take a year to actually come to fruition on all the stuff that you see as sufficient to satisfy this problem. That's where experience comes in. And that's almost like the other side of being the business owner, right? The idea and the insight, phenomenal and important. And now to understand what you need to put together, who you need to put together to get it done.

The like taste that you're adding to it in your own sense of things. It's like, it's fun. This is kind of what we're talking about before, it was running your own business. It is a creation process. I'm no artist, but this is where we get to do it as humans to create and build something.

And we're doing it online, but it is a form of building.

And I would say this whole research process has, I've done plenty of customer interviews in my previous businesses, but I've never gone this deep before. And the creative side of it is like, man, I know the problems so much more in detail on this one than I did in the previous ones. And so that's the creative side is like, well, how can we come up with a solution that, A, works really great for these customers and B, like, there's another angle to this is like, well, if we're building this, how how are we positioned it? How how will this be positioned in the market? So if we're up against these competitors in this side of the market, how are we different from them?

And then there's these competitors on that side of the market, how are we different from them? Strategizing around that is a big part of it too. Yeah,

it's fun. We're engaged in right now is building up the team and the processes that are essential in effectively taking the software product that we've built, and then the entire mechanism of getting people interested, getting people to know about it, get interested in it, want to try it, sign up for it, onboard it, become successful with it, stay with it. Like, so we have-

What's that look like? Is the-

Yeah, we've a lot of like team things happen. I don't know how else to say it. There's been turmoil is the wrong word, movement. So we've had a lot of, we fired one person, we hired one person, one person resigned, we hired two more people. This person joined, this person's moving here, this person's resigning.

There's just been a lot of movement over the last month or so. And I feel like fully engaged. It's kind of a weird feeling. I'm very, very engaged in it, but it's almost like I'm having very little emotional response. I feel like I'm acting like a professional when it comes to this.

I'm very sad to fire someone. That sucks. But I my emotional register is pretty flat. I'm like, that is not good. I don't like that.

That's partly my failure and the company's failure and partly the person's failure. And it's right for us to split. And now what needs to happen next? I don't know if calculating is the right word is. I'm trying to it's hard to describe, but it is No.

Mean,

everyone knows this. Letting someone go is the worst. Nobody ever sets out to end up there. How many times have we seen, and myself included, I'm sure you too, where you have someone who you know there's a problem here or it's just, this is not getting it done, this is not a good fit, and they stay on for longer than you would have Right. Worse.

So,

yeah. So we've brought on a sales team and it feels like I'm cobbling together these pieces that will form the process. So if we think about it from a funnel point of view, right, let's start at the top of the funnel. We've brought in a director of marketing. This is an interesting case where like the macro environment has an impact on your company.

Our one of our direct competitors failed to raise money and is going out of business. Sucks, right? We all sympathize. But it created an opportunity for a marketer that has been working on a checkout product in the e commerce space to come over and just bring all of that institutional knowledge. So that was like this fantastic opportunity.

And she is senior enough that we can look to her to drive strategy also. And it's been a funny experience with her because I used to think of myself as a marketing minded founder, and I'm no longer that. And when she came in, we started talking about it, I had to like, brush away the cobwebs of my marketing Like, oh, I have not thought deeply on marketing in too long. And some of it was, there was an element of shame.

Are there any like big ideas, big concepts that you can talk about? Like not your specific marketing, but like, I don't know, things that

I mean, is where that chain comes in. Because some the very, very basic stuff we have not been doing, because we have been doing a different thing. We have been acquiring customers through direct sales. And what that really means is that you're not reliant on like posting content. And then you get that rolling and then all of a sudden you realize, oh, our little startup hasn't published a blog post in six months.

And I am embarrassed about it.

No. But same here, though. I mean, and like with content specifically, we're doing it in in a way that I I believe is the right way to do it, but it's completely different. And I ran a content marketing company for six years, and we didn't even do it the way that we're currently doing it on Zip Message, you know? And it's like, wow, this is this is so much there there's actually

a strategy here, you know? Yes. So it feels it feels amazing to bring someone in like that. And she's basically taking the baton and saying, don't worry, I got it. You know, and it kind of soothing me on like, you don't need to feel guilty.

Here's what we're going to do. And then it really turns into an exercise in, Okay, let me admit that I am not going to be doing the marketing. I'm not going to be thinking about marketing needle as much as this person. My role right now is to empower this person, tell them to think big and ambitiously and let them know that I got their back and whatever resources they need up to an extent they have. So be aggressive.

And then start to put in a framework of reporting and accountability and like ideas and then start to back away. And it feels like I need to do that over and over and over again. So right, that is on the marketing side. On the sales side, we brought in a consultant. And he helped hire two AEs that are now full time, and they are often running and they are generating demos and they close the deal.

It's only been a week and a half. And so now here we go. So now that's starting to run. And then again, I have to admit, I'm not a salesperson. Don't know the right thing.

I need a leader in there that's going to report it to me. And then I need to tell them, here's your budget, here are your resources, tell me what you need. And then, you know, this morning I had an interview with a customer success, like leadership role. So now it's like, okay, this really building a Really

build that process.

That's right. And then kind of explain, okay, here's how customer success works in this business. Here's why it's so important. Here's the hard part. Here's where we don't have an issue getting someone interested.

When we show the demo, the majority of people are interested. That's not the hard part. The hard part is going from interested to live and processing revenue. Therefore, this is what you're measured on. And this is why it's hugely important.

And here's the VP of product that you're going to talk to and make sure we get things right for the customers. Here's the person leading sales because you're going to work very closely together in a good way, not in a butthead sort of way because that can happen, right? Sales can bring people in that success fails to onboard properly and then success gets upset. So I'm like, oh, I'm almost like remembering these.

Yeah, like the friction that happened.

Yeah, they're not detailed. It's like how the machine works. And fortunately, it feels like now is when we're gonna get the benefit of having done this before at Cardhook, because I'm literally conveying here's what you should expect, good, bad, ugly, healthy, not healthy, all that stuff. So it feels like Do there

find, I've seen this in a lot of my businesses and I see this with a lot of SaaS, especially B2B SaaS that are big solutions. You have to catch the customer at the right time. They have to be looking to, I guess in your case, would you say it's like overhauling their checkout? Like they have to be in the mode of like, we're gonna overhaul our checkout this quarter.

You know, it's not that way for us. And it is both a strength and weakness of our business. Our weakness is that nobody wakes up one day and says, you know what I'm going to do? I'm going to look around for a new checkout. They don't do that because they don't even know that it's possible.

So that's the con side of it, the weakness part. The strength of it is that no one's doing it. And it's so new and so interesting and exciting to these people because it's like you're running your business day to day and then someone comes along and says, I got something for you you've never seen before that can make a huge impact in your business. And like, it's legit. I'm serious about it.

It's not just like a promise I mean. And so what we have to do is figure out, we have to figure out two levels, right? When it comes to marketing, the way we're thinking about it is we don't just need to tell the market about our solution. We have to first convince the market that they need a checkout solution and they should not be happy with what they have right now. And then that needs to lead into rally being the obvious choice, partly because rally is the one that educated them on their need for a checkout.

But we have to be okay with not winning the entire market. We still need to do the education.

We run into this actually quite a bit because we, now we get a lot more leads who are just organically finding us, But there's a small number who actually Google search for a solution. And we have and that's where we're developing our SEO content strategies around like this intent based stuff. But that's a very there just aren't that many people searching for this total product as a solution. So, I've done a lot of guest posts. I did like a webinar on SPI last week and two two webinars actually last week.

And like so like and guest articles. Like people are just like hearing about it in in random places. And so like, they just stumble across this thing called zip message. It's like, oh, maybe I could use that. And then they go sign up.

Like they they weren't in a mode of like in the market searching for it. And and actually what I found is is they stumble into us. They hear about us in some random place. They they sign up, and then they go sign up for competitors. And then and then it, like, kicks off a whole Right.

Like, you introduced a concept.

The idea to them, and and now they're comparing us against competitors. Yes. Which sort of sucks, sort of good. I don't know.

I'm trying to remove the sucks part of that mindset because there's enough benefit for being the ones that introduce the concept. And we've all experienced it with like other products and other companies and other brands that once you establish yourself as like the source of that concept, you do win the majority of things because you are that source, you still have to execute. On the sales front, it's slightly different because it's really more focused on the second part of that, which is knocking on people's foreheads and saying, Hey, do you want to see this new thing you can do? But it all falls apart unless you can onboard people properly. And if the features aren't right, and it's like, okay, we're building the machine.

I know it's sort of just coming together for your customer success team now, but like, what does that look like for someone to go from, okay, they they are excited from the sales call. Now, what else needs to happen for them to be active and using it?

A lot.

Yeah. Like, what is like implementation? What does activation look like? And how, how are you thinking about, how are you thinking about jumping them through these hoops? Because I, I, that's a constant thing with us.

Like, like I've overhauled our onboarding multiple times and, and as we build these new features, it's gonna become more hands on, I think. I think we're eventually gonna get to a point where we're doing more concierge onboarding, done with onboarding, all that kind of stuff.

Yeah. We are not even pretending. We are just going fully hands on for the foreseeable future. Yeah. And that's really, that's the only thing that makes sense for a while.

It is not necessarily a bad thing. We had a great time doing it at Cardhook. You build up the relationships, you build the forgiveness buffer, you get to add value, you learn a lot. We love that part of it. The single most difficult role that we have had at both Cardhook and Rally is the solutions engineer.

The engineering work that goes into onboarding, we do not know what to do with. We are trying to figure it out. One of the people that resigned was the solutions engineer that we brought on board. He was around for a month. Like, that's not good.

Like, maybe sure, he deserves some of the blame on maybe not understanding what he was getting himself into or whatever else. But there's definitely a healthy portion of that that's our fault. And so I am currently engaged in like a fact finding research mission on like how are companies doing this? Is it a success role, a support role, a sales role? Is it a rotation of engineers?

Like how do we do this? How do we find-

When it's like, you have to get your hands dirty with the code. That means you have to have some engineering chops.

Right. You have the engineering chops, but you're not building features. And you're also talking to customers and it's really, it's a really difficult.

Or at least they're talking to your customer success person, right? Like they don't necessarily have to be Maybe they're in a call with a customer, but they don't have to be have that personality of being a customer success. Like the customer success person can lead that and then just delegate to the engineer.

Yes. But you want them able to talk to merchants. You don't want to go through the success manager for every single interaction. So you just need to be personal enough and ideally enjoy it.

Could this be like a junior junior engineer?

We've it all. We've tried junior. We've tried just out of coding school. We've tried full blown, full stack engineer. We've we've tried it all.

And it is a difficult one to figure out. I'm determined to figure it out because it's necessary in order to accomplish the successful onboarding. That's that.

Some of the guys over in Confund are starting to put together this no code as a service concept, and they're sort of experimenting with it. I don't even know if that's public, but and I was talking to them a little bit, but because I see a lot of these no code consultants. There there there are a lot of them. We we've had several customers who literally, that's what they do. Companies hire them to rig up complex no code solutions using multiple no code tools out there, right?

That sounds ridiculous, but I understand what you

mean. Totally. I mean, it's not just a basic Zapier zap. It's a super complex Zapier zap that talks to Airtable's power features that talks to this and that and that spreadsheet and all this different stuff. Right?

Your CRM. So I think that like, yes, there's that need. Companies always need to rig up their internal ops with no code stuff. But I think this, what you're describing, this solutions engineer, I don't know if it's the right thing for Rally, but like in general, there's a lot of SaaS who who need that that last step, that onboarding to integrate your SaaS with the four other tools that are integral to their business, have somebody like instead of pointing them to your knowledge base docs, or instead of telling them, hey, go to Zapier. We've got a Zapier integration.

Go figure it out. Like, no, have someone on your team who is a no code wizard and that's their role is just hook them up with what And it's gonna be different for every customer, but that's what they thrive in.

Yeah, what we found is there's one degree or maybe several degrees higher technical ability required in order to accomplish it than no code solutions. That's the bottom line. That's thing. Yeah, when someone goes, we are using, how do we use one payment processor for our BigCommerce checkout and one payment processor for Alley? Like, you know what?

That's no code. That's just a yes, we have that feature. But then the next question is how do I get these tracking scripts for Instagram, TikTok and Snap from my Google Tag Manager at the BigCommerce level over to the Rally Checker to make sure it works? Like, okay, cool. You can copy and paste.

Great. Now test it out. Now make tweaks. Now make adjustments. Oh, it's coming in, but it's actually showing the wrong price.

It's not taking shipping into account. So like at some point you got to start looking underneath and understanding what's happened. Yeah.

Holy man. How are we doing on time? Should we wrap it up?

I think we should wrap it up. I feel like, you know, we just keep going this conversation for a long time. Yeah, it's been about an hour.

Good stuff.

Yeah, I feel like today was a good view on like, you know, just what's on our mind on the promise of trying to solve.

That's right. That's right. Well, hopefully we'll get a bunch more updates in the next few weeks. I'm excited. Yeah.

Good stuff. Thanks for listening, everyone.

Later, folks.