Bootstrapped Web

Welcome back, everybody, to another episode of Bootstrap Web. Mr. Brian Castle, how are you?

Hey, how's it going? Good. Here we go.

Good. Good. It's Friday. Just had lunch with my wife, came down to the co working space, went outside. Beautiful day still.

Feels like Chicago is clearly enjoying like the perfect few weeks in the fall. Beautiful. Before the plunge.

Yeah. Today, it's it's beautiful over here. It's like the first kind of chilly day. And it feels great because it's one of those like early fall, like like kind of cool, really sunny. But like inside my house, it becomes an icebox.

Today is day one of like sweatpants, slippers, sweatshirt, you know. Yesterday I was in like shorts, today I'm in sweats. So here we go.

All right,

Bud, the weekend's coming up.

Yeah. So over the summer, we had a little summer project on our house. My wife and I built out a whole gravel area in our backyard and we built a fire pit. And so tonight, I think we are doing our first fire, first first s'mores in the backyard.

Okay. Nice. Well, I just had a very strong cold brew, so I'm ready.

Okay. Thanks to the people got more energy than I do.

Oh, I'm pumped up. Thanks to the people who responded to your tweet around what to potentially talk about today. So we got things over there. Yeah, got a couple of

good ones. Let's, know, let's, I guess, just dive right into that stuff.

Yeah. Hell yeah. Why not?

Why don't we start with the one about operations versus growth? What All do right. So Daniel, I've seen Daniel around on a lot of stuff. Can never pronounce his last name. Sorry, Daniel.

Daniel Montzuras?

Yeah.

The question was like, you know, what should we talk about on the show? And he said, dedicating time to operations versus growth, how are you prioritizing it? It sometimes feels like a chicken or egg situation, which it definitely does. So what are you thinking on here, Andre?

So I think it depends on your business, but everyone has some version of this. So a lot of times like agencies, right? That is servicing your customers versus going out and getting new customers. So operations versus growth, that might be what Daniel's kind of alluding to, something like that.

It is different in SaaS.

Yeah, every business, but there is like a like.

I mean, there's still that friction. Definitely, I feel it, but it's a different, it is different than like an agency or freelancer where it's like, I have projects and I have to try to keep the pipeline for future projects. I think with SaaS, it's like, yeah, like build what's currently happening in the current cycles, but we have to be planning for upcoming roadmap.

Yeah. Good. So it

depends on the business. For us, we have it at the business level and then I have it at like my personal or like contributor level. So the way we talk about it internally, the way I like frame it is that we never want to punish for sales success. Meaning, how do we separate the two? How do we separate the people and the activities that go out and get new customers?

And how do we make sure that they don't get bogged down by being successful by adding new customers? So the way I talk about it in the company is like, need to let the sales and marketing run out in front of us. And whatever wake they leave behind them, we will figure out how to handle. And we don't want them to have to look back at the wake and say, is that too much for you? Right?

We just want to say go, go, go, go, go, go, go nonstop. So at the company level, that's kind of how I think about it. Over the last month, we hired a bunch of people, we had seven people, many of those were on sales and marketing. So now it feels very much like, people can start to run and there's enough people in the organization to handle whatever wake comes their way. It's not all ironed out, but we still don't want it to slow down.

So it's better off like just throw more stuff at us. And then we'll figure out what mistakes we're making and who we're going after and why, and are they a good fit and maybe making some adjustments upfront to the sales marketing. But right now it's like, just bring it.

Yeah, yeah. I think where I feel this tension is, I think a part of it is due to our small size of the team and my role being, I feel like I'm an integral part of everything that's going on, which means that I am definitely the bottleneck on everything. And so, you know, we're much smaller than your team. So I work with Claire to kind of coordinate all of our marketing efforts and we have multiple projects. And also on that side of the business, there's a writer, an SEO strategist, a VA, but Claire is the main person that I'm like kind of collaborating with on stuff.

And then on the other side is the product. It's me plus the developers. And I feel like I am the creative directorproject manager on both sides of the business. And I'm contributing actual, like I'm building on code features and I'm collaborating on technical stuff. We just shipped a major feature on the product side with video editing this week.

Awesome, looks nice.

And that was a huge, huge lift in terms of like hours on my part, on both of my developers. It was a huge thing for us to get built. It was super complex. And then we had several weeks of just testing and ironing out the edge cases. So that was a big time suck.

I'm so glad that was out the door. But then on the other side, I think in terms of like my left and my right side, right? Like my left side is marketing and like we're launching a big new marketing project. And so what I think about, I'm constantly going in these cycles of building mode and then it's like, it becomes an engine that just keeps running. And this is especially on the marketing side.

So like a few months ago, we were sort of building and retooling our article development SEO operation between our keyword research into topics and search intent and then writing article briefs and then having the article written and edited and published, distributed, link building, all that stuff was a huge two, three month effort of like finding the right people, putting them in the right seats, giving them the right process. And that was like building mode. But now that's like up and running as an engine that I don't have to really touch too much. I give input here and there, but like the team is running with that.

Yeah. Is, which feels like that's kind of what you need to do so that you don't interrupt the forward progress.

Yeah. But now we're onto like, sort of like the next big marketing project. I don't want to say what it is yet because we're going to be launching it in a few weeks. Right now it's actually like soft launching with like invite only with some first few people, but it's like a big project like the brand audience space by Zip Message. And I was giving a lot of creative input and a little bit of technical, like setting up a new web page and some technical stuff.

Claire is going to be running with that. And then as that gets actually launched, then again, I can like step back and not really be involved. But like the friction for me is like, I've been talking about how I've been doing all these research interviews. I have a really clear roadmap and I've started to design the new features that we'll be building, especially toward coaches. And as this comes together, I'll talk more about what these new features are going to be, but that's a it's a really big roadmap ahead.

And frankly, we haven't been able to really crack into it too much other than me designing some of the UI because a, the product team has been focused on this video editing feature. That's now done. But meanwhile, bugs have been piling up in their queues, right? And then on the marketing side, like all my time has been sucked into collaborating and getting things going. And then I have to try to squeeze in like quick wins, like doing a webinar over here and there and doing a quick integration when we did a ConvertKit integration.

And like what I'm thinking about is like the thing that the business really, really needs is to build these big new things and which will take us to a whole new position in the market in terms of what we are, even what we can charge. It's going to take us to a whole new position, but that's a huge effort. But I have too many projects that are sucking my time right now. So that's the tension for me.

Yeah, I think most people listening will sympathize. I certainly sympathize. And I don't know if it's going to make you feel any better, but having millions of dollars in the bank doesn't actually help. So I feel feel a bit trapped. It's almost like I'm trapped by like, I mean, it's reality.

I want us to build what I think the product needs to be in the future. But we won't be around long enough unless we get the traction from the current market and then are able to raise more money, right, generate new revenue and raise more money in the future. And sometimes I get frustrated because when I was a card, I had like an easy excuse. I said, Well, we got to we got to stay profitable and we got to keep an eye on the bank account. And we're like, you know, working within the confines of like a profitable business without a ton of resources.

And what that meant was doesn't really matter what I want to happen three years into the future, because I got to I got to focus on now. I really hoped that raising venture would allow us to be more disconnected from like the day to day realities.

Because it just extends your roadmap so much.

Right, right. And you do have more resources, you do have more people. I mean, your runway. Right. Runway resources, people, energy, the number of developers, designers, all that stuff.

But it still feels pretty confined, pretty constrained, I should say.

When you describe that in your situation, it makes me think of like a playoff series in whatever, baseball or basketball or something where it's like

Like looking ahead to the next opponent, but you gotta win the

first It's like the Mets are gonna need to pitch DeGrom in a game one or or a game two. Like, they're they're ace pitcher. Right? You can't just, like, save him for a game five or game six situation because if you lose game three, then your season game four, your your season is done. Like, you have to focus on, like, what you need to survive right now.

Yeah. But I'm not sure if I'm right. Because that feels like the safe way to go. And I sometimes have this fear hanging around that someone's going to come out with a product that I think needs to exist in the future and that I know needs to exist. And I'm not being brave enough to just build it and basically hope that the market gets there around the time that the product's ready.

That's an interesting thing. I deal with it too, because it's like, I wonder how you think about it. Because I think about it like, all right, like literally this week I had two more research calls with coaches who are using Zip Message and they came out of coaches who, first of all, they Google searched and they found Zip Message and they became customers. And then just like so many others before them, their first support messages, like I'm trying to do this and this, How do I do that? Or can I integrate it with that or this tool because I'm trying to achieve this, which is exactly what all these other coaches have been trying to do?

And it's just like, again, it's like the thirty fifth person that has like reconfirmed what we need to build. But I'm like, if I go do this webinar over there, I'm gonna get 10 more customers this month. Or if I don't collaborate with my marketing team to get then these engines that we need to be up and running are gonna be two more months delayed, you know? And that's a long game anyway. So the log we delay, then all of a sudden, like all these things that we need to build are not being built.

So it's like, so I could, like the choice is, I could just say, no, I'm not going to work on marketing or no, I'm, you know, I'm not going to, I'm going to say no to all these little quick win opportunities and just go heads down and build the stuff. But then we go months with just continuing a plateau and that's not sustainable.

It is. It is risk, by the way. You are taking the risk either way. And I think often we we try to split the difference. And that feels dangerous too.

So it's I mean, for us, it is it is very straightforward and it is not a mystery. All the GMV right now in e commerce is on the big platforms, the BigCommerce, Salesforce, WooCommerce, right Shopify, of course, but we don't deal with them. And so building a checkout for the BigCommerce, WooCommerce, Salesforce, Magento, that is what makes sense right now because that's where the customers are. But we want to build a checkout for the headless e commerce ecosystem so that developers can take a front end and a back end and use our checkout as the glue between the two to make it really easy to build new e commerce experiences for brands.

Is the headless market mature? That's part one of the question. Part two is like, is your pipeline, your leads, are they headless people or are they a mix?

So no, because the marketing and the sales that we're doing are toward the platforms. And we have a great partner in BigCommerce and working together and, you know, when we're building a Salesforce integration. So it's kind of like that is what makes sense in front of us. The headless ecosystem is not mature. It is maturing, but it is not mature.

The thing that bothers me is that what I honestly think is that our product is a key piece to the maturation of the headless ecosystem because it is not easy. Nobody wants to build and maintain their own checkout. And we think of headless very differently than most people. Most people think, oh, I got a Shopify store and I'm going go, you know, spend six months and $250 to go build a front end that works with my existing Shopify store. That's going be a giant pain in the ass to manage.

That's not what we think of headless. We think grab builder.io, grab rally, grab swell. All of a sudden you have this new no code, low code stack that is a lot more free in terms of the ability to do what you want on it than a Shopify and more cost effective and much more modern in terms of the tech stack. But like. That is risky compared to just going to a big commerce merchant that does $5,000,000 a year and say, hey, we'll give you better checkout features.

So to me, right thing to do is focus on what's in front of us, get the traction, get revenue, get to the next level, raise more money and then figure out a way to have the resources to go toward toward the future. But it is it is it is a mixed bag. And I think that's what the tweet is about. Everyone has their own version of that. Should I do what's in front of me?

Or should I do what I think I need to be doing for two months, three months, six months, twelve months out in the future?

Yeah, totally. It's like the age old question, you know?

Yeah, it's tough.

Should we move on to this other one? This one might get really interesting. Let's see. Pascal. Yeah.

He he asks, if you were to start anew, what three industries, verticals, niches would you would each of you invest time digging into bit by bit? Oh, you might have too much fun with this one. I don't know.

First of all, shout out to Pascal for having an awesome name. Pascal La Liberte.

He's the man. Worked with Pascal a little bit several months ago. Was really helpful for me in analyzing some of the early jobs to be done interviews that he

was doing.

So basically I was doing the interviews and then he would listen to the recordings and then he and I would go on Zip Message and just share our each of our notes on them. It was really helpful.

That's cool. Well, Pascal the free, thanks for the tweet. All right. So if you were to start anew, what industries, verticals, niches would each of you invest time digging into?

I mean, I wish that I had time to actually think about this question before we hit record, but we were talking a little bit off air. My first thought is I wish that I had the opportunity to step away from all businesses for an extended period of time, like call it six months or so, or a year, to just be away and then analyze the world and be super strategic about where I want to invest my energy into the next business. And the reason I say that is because every business that I've ever had has been a reaction to the previous business.

So it's been connected in

some It's always connected. I could literally, it's a chain link, going from freelancer to WordPress themes, to restaurant engine, to audience ops, to ops calendar, then, you know, and then process kit and then zip message. It's been I had a really good conversation with my friend, Caitlin Jordan on my other podcast over on OpenThreads about this. How like every business idea for me has been like trying to solve whatever problem or challenge I had in the previous one or like doubling down on something that was sort of working in

the past. Right, or something that you learned from one Okay, so what you're saying is if you

And I think that hasn't always been beneficial for me. I don't have a strong opinion one way or another on like scratching your own itch. I tend to go for things that do scratch my own itch initially. There are definitely times, I experienced this with ProcessKit, I experienced it at times with Zip Message, but although I'm very into what we're doing at Zip Message now, where it's like, man, if I had a little bit more time and space to be more strategic about the market and the problem set that we're choosing from the outset, maybe I would have done this or that differently. But it was more like I was in the moment.

My judgment was clouded by my most recent experience. So, you know.

Yeah. Well, Rally, obviously pretty closely related to the previous company. And I'm I think it's totally Okay to not be consistent because I like you love what we're doing. I don't have a bigger idea. I'm very happy doing this for a long time.

But I sometimes think back on like, what if I just sold Cardhook kind of the way I thought it was going to end? And like, I even be in e commerce at all? Yeah. So, okay. So let's, right, let's, let's

fantasize a little bit here. Right.

Okay, let's say your business disappears in a good way. No connection. You don't have to do anything for it. You get enough money dropped into your bank account that you are calm and patient, and you get to go out and observe the world without a rush toward this next thing. You have a few months, six months, twelve months, you have time.

Where do you think you get drawn into? I'm for me, I think I think it's Okay, an obvious three

let's see.

Again, I wish I had a little bit more time, but one thing that I'm interested in right now, and it seems to be the trending topic on Twitter this month is AI driven, especially image generation, illustration and and image generation. But there there's also the the writing tools, like AI driven writing tools, which I think on both of these fronts, the actual quality and output is still a little bit janky in general. It's pretty impressive how far it's come, but to me, it's completely obvious that this is not just a fad that's going to disappear. I do think that AI driven tech is going to be a major game changer in our industry for sure, and probably much further beyond that. And and I mean, you can absolutely see it in graphic design, like like generating graphics for things and writing, like whatever, articles, content.

If I had like unlimited time and resources to just play around as a technical person, I would be playing with this technology and thinking about and trying to explore specific use cases that I could build into and really try to take advantage of some of the early mover advantage because it is a cutting edge technology. I think it's one of those things where it's like, there's a lot of cutting edge tech out there at all times, but this one to me is like such an obvious use case. Or there are so many obvious use cases for AI generated graphic design, let's say, right? So that like, to me, it's hard to imagine that this is not a significant tech in our future. So I would be probably looking to build something in that area.

That's just one, the first thing that comes to mind, because it's sort of on my Twitter timeline this week.

So that's like a, you're identifying something that's A, interesting to you, and B, feels like it's an obvious ground floor type of an entry point that's going to

I'll say this, I think that A, it's interesting technology wise, but it's also like, there are very few opportunities where you can actually take advantage of a first mover advantage being one of the early Think about like Basecamp was like an early mover on project management software and SaaS in general. Right? I don't know, like Stripe with payments. I'm trying to think like better examples. But like, this is one of those things where we're still in like pre game.

We're in the pre season of AI driven technology, but the season is coming and there are gonna be players that, and there are gonna be companies that emerge out of this technology. I think it's even opportunities for bootstrappers in this space too. That's one. But yeah, bounce it over to you.

I get worried that the biggest companies are going to have, you know, that AI will require so much compute power that it does end up in where all the money is, where the resources and the compute power ends up.

It could go that way, but I think that there it'll be more than just the technology itself. Think that it'll spawn It'll spawn all sorts of things, service businesses. And I do think that there's still a place for creative people, designers who can manipulate AI prompts in a really creative, interesting way. Like that could be just a-

Right, almost like you end up as a director, producer.

Yeah, like you could be like a, I don't know what they'll call it, like an AI whisperer. Like whatever, you know, like.

Have you seen what Peter Levels has been doing? Messing around with like house design?

No, I don't think

I saw Peter, the nomad guy. Check out his Twitter feed because he's gotten into some of this AI generated artwork, but he's been playing around with it on like, what can you do to like mash things up? So he's been using prompts around architecture. So he's getting designs, but then he's trying to figure out how do I get the blueprints and then the house designed on top of it so that they match? It's kind of like an interesting thread for him, thread to follow.

That's a perfect example. Like, who knows what that could turn into, you know? Right. Right.

Okay. Cool. I like it.

What are what are you thinking? What what's like the I mean, you're gonna start talking about crypto. So here we go.

Okay. So I I'm obviously gonna start talking about crypto. So my first one, I'm not gonna make crypto. I'm gonna make one of other ones. And that is I am fascinated by the by I guess you would call media businesses in the modern web.

Yep.

I just don't think there's ever, ever been anything like the one to many ratio that we're seeing now. So, you know, I don't want to I'm not going to delve into like adult content, but OnlyFans to me a is sign of what's to come. Right?

It's a person. This is getting very interesting.

Well, it's just the most extreme because it's the most base human version of this. You can also look at TikTok influencers. You can look at people on YouTube. There's never been a situation where one person can have more power and generate the same level of revenue as like a gigantic media company. So it would feel crazy to not go after something like that.

I wouldn't want to be a creator. I would want to basically build a company that helps people do that. Basically like the media company of the future is either one person or that person using a media company services to generate and monetize an audience.

Yeah. So like, what would this look like? Do you mean like you would become like a brand that hires talent to generate content in different niche verticals? Like, I don't know.

Yes. Yeah. I don't know if it's like a, it's not really a talent agency, but it's just helping the most talented people create audiences online. Right now, it is a very, very specialized skill to not only be very interesting and talented, but to also understand how to do all this stuff. And there a lot more talented people out in the world.

And these days, what talent can do, you can be talented in nearly anything and have a massive audience because the whole thing's been flattened and you're global. And as things, I mean, right, touching on the crypto side of it, that will flatten economics and monetization and all of that along with it. And so there's just the ability to get huge audiences for very niche things that in the past would never make sense because the audience just simply isn't big enough. So now if you can show, I mean, some of the stuff on TikTok will show you how niche things get where, you know, I don't know what the hell I came across. Some like jacked, like older dude, basically teaching people that it was the most niche thing ever.

It was like, if you Like sprint

fitness for old people?

Yes. If you sprint this many times a week, it will increase your testosterone and longevity and sex drive and all this other stuff, this health benefits. It's like the most niche thing ever. And then you go and he has like 500,000 followers.

So

it's things like that. So I would be looking to capitalize on that dynamic.

Little sidetrack on, I tweeted on, because I keep hearing people talk about TikTok as this emerging platform. Obviously it's become a major network now, but I mean, it's emerging in terms of like, we should be thinking about it or have some, I don't know, like presence or like, or leveraging it in business in some way. And I keep hearing that sort of sentiment come up again and again. I'm like, what? You know?

Because it's like, to me, TikTok is amazing for funny videos that I can enjoy with my kids. You know, like-

Yeah, but it's just people. It's like Facebook was good for connecting with friends.

So I asked Twitter the other day. I was like, what what else is there? Like, what what other version of TikTok am I not seeing here? And and some of the responses are interesting. Like like, people like search for, I guess, like cooking recipes is an interesting one.

Somebody said a thing about like locations. Like if I'm looking for a rooftop bar in NYC, like I would I was like, why wouldn't you use Google Maps for that? But I guess there's a whole location based thing TikTok.

That's right. There was a study done like in our world around brands. And Google is very concerned because ages, I forgot what it was, like 19 to 29 or whatever, some like important segment. The majority of them were going to TikTok for their searches.

Yeah. Which is amazing to me.

It's amazing.

Yeah. So anyway, like it just goes to show that there are totally different use cases from the obvious use case of almost anything, but definitely that. I want to try to think through this question from like a bootstrappers perspective right now. Okay. All right.

So like if you're bootstrapping, if you've been maybe consulting or if you're at a job, like it's 2022, what kind of opportunities would I be thinking about in terms of trying to launch a business? I'm trying to be more strategic about this and avoid the thing that's right in front of me lately, but I'll just talk about it. It's the only thing I have right

now. Yeah. Go for it. I don't think I would use software.

I'm not saying this is necessarily like for me, my preferences, but just for other people. I do think that there is an opportunity to offer coaching because I just think that this is more prevalent now than it was even just a few years ago. And it's more of an opportunity and easy opportunity. There's always been like coaching, whether it's like business coaching or life coaching or nutrition or health coaching, right? But I think that the tools, obviously Zip Message, other tools out there that offer asynchronous coaching and group coaching and small group coaching is just an easier way to add value.

It's an easy way to be effective and really to get paying clients. If you're trying to grow revenue and build trust in a particular market and even learn more from a particular market, you know, I think it's a great stepping stone into something larger. And it goes hand in hand with growing like an audience and a community.

Yes. Similar.

But what I like about it is that it's fast to launch. I think speed is everything if you're a Bootstrapper and really in SaaS in general, we were just talking about that. Like just you have to move through the roadmap as quickly as possible. So I think that that's one of those things, just like productized services that I've talked about for years, but I think this is an even simpler, more direct way to provide value is to, if you're a solo person, you don't necessarily want to grow a team yet, just get a handful of clients on coaching in some particular area.

Yeah. That feels like one of the best business models online.

Yeah.

Like business expertise on a one to many basis is really, you know, I used to follow lists like back in the day, maybe before Cardhook, I used to follow some of like the marketing, like guru type coaches. And they were just able to build unbelievably good businesses by showing proof that they knew what they were doing, giving a lot of value upfront, and then having cohort based coaching. And you could absolutely print money. You can make an enormous impact on your customers and make an enormous amount of money very efficiently.

I think what I'm trying to say with this is that like, there's actually a movement that I'm seeing. I see it clearly in all these research interviews I've been doing all summer, which is like, just a couple of years ago, it was all about courses.

Okay.

Somebody wants to, like a bootstrapper wants to write and sell an ebook or write and sell a course. That was the thing to do to make quote unquote passive income online.

Like the Nathan Barry, like buy it for 50, buy it for 200, buy it for 800, like the theater from tears. Okay.

That became a very popular model. I followed it with my productized stuff, and it worked worked pretty well for those years.

So what's different now?

And that stuff will always be around. There will always be eBooks and stuff to buy. But I think that what most people are finding now, both the creators and the people who buy that stuff, is that it's not enough to just passively deliver a course or passively consume a course or an ebook. What coaches have learned is that, you know, because most coaches also have some form of a course or usually like a library of assets. And I see this so closely in everything I talk to them about, but they add the personalized attention element, right?

Student B is a little bit more advanced than student A. So let's direct student B to just this and that module instead of these other modules. And let's actually have some like interactive Q and A or feedback or exercises or assessments personalized to each person. And let's do it at scale because we could do it asynchronously. Like this obviously gets into what we're building with Zip Message.

But what I'm saying is like, I do think that there is an opportunity if you are some form of a creator and you like helping people and you like working directly with people, there is a very nice business, a bootstrapped business that you can launch pretty quickly recurring revenue with this sort of model.

So that's really a response to the reality that the totally passive course doesn't lead to success often enough.

That's the big thing. It's like, you hear this again and again, like the percentage of people who buy a course that are actually successful with it or let alone even take any sort of action with it is so low, it's like embarrassingly low.

Right, and so you're really making promises and getting people to buy based on them wanting to get promise Based on the that value chain

page, but there's no follow through on the implementation, the accountability, the community, everything.

Right, the elements that make success more likely. So at the same time, you don't want to go totally custom because then you lose a lot of the efficiency and you have

to charge It's too not scalable to go on an hour long Zoom call with every single buyer. If you could do it on a group level, if you could do it asynchronously.

So that's okay. That helps. It also helps understand your vision around SIP message in being a key tool.

And this totally doesn't answer Pascal's question. I'm just talking about my product now.

Yeah, whatever. Pascal, I appreciate the tweet. This is our podcast now.

Yeah, but yeah. I have one more point. I mean, do you another one you want to talk about on this?

Yeah, what do I got? What do I got? I don't know, is it your turn? I don't know where we are.

I got one more thought on this. Just in terms of like, for me at least, it's always like the grass is always greener whatever I'm not working on. And this is probably why I've had like shiny object syndrome my whole career. Right? You know, I think the other thing that I would probably be thinking about now, if let's say I am set on the idea of doing a SaaS, which is probably an open question too.

Like we could get into like, what would you do if you weren't in SaaS? But anyway, if I'm a independent person, bootstrap, especially a bootstrap person who I want, and I want to build a successful SaaS company, where would I start in 2022? I would probably try to find a niche industry and really understand a problem that I can not only build a good solution for, but I can charge hundreds per month, not tens per month. And I would go directly to that from the outset. This is almost like SaaS 101 these days.

It's like, if you can raise your ARPU, you will have an easier time, you know, you just don't need as many customers to grow. Now you could go much higher ARPU and then you get into the realm of like productized services and consulting, but then that requires a lot more people. But if you're in a niche industry that has money and you're selling to businesses and you can have some insider track, whether it's just you or you have a brother-in-law or someone who works in some industry and you know of some problem that the larger world doesn't really know about, but this industry feels that if you could replace those messy spreadsheets, and I mean, that's been the game plan for the last fifteen years of bootstrapped SaaS, but I do still think that those things are out there and, you know, if so that's like a for me, that's like a grass is always greener because I'm doing zip message, which is not that. It's, you know, it's so that's where

I More would risky is the right way to put it or what. Yeah, for me, I'll save everyone the pain of hearing me talk about crypto again. I see that similar to how you talked about AI, where it feels very obvious that it is inevitable. There's a lot of stuff to do there and it feels like it's on the Ground Floor, maybe not Ground Floor quite the same way. So what I would talk about is my guess is everyone listening has something that kind of like sparks their interest and passion outside of business.

For me these days, it's around like food media and like the David Chang podcast world, Mamafuku, like so the food world is fascinating to me. And if I like had the time and wherewithal to kind of like explore, that sounds like an area that I would be interested in going into in terms of like an actual interest and a passion to kind of explore and get involved in that. Oftentimes it's better off to not mix business with that. But if I had the magic wand and I had time and I didn't have to kind of think about what to do next very quickly, That feels like something that I could be passionate about, right? I think about my I had a friend.

She's still a friend, although I don't see her as much. And she worked for zero point zero productions. So that is the production company that did Anthony Bourdain show and Mind of a Chef. And that to me is just fascinating because the actual product that comes out of it is so interesting and like something to be so proud of. You know, it's art.

You really, at the end of the day, you're creating some type of art and it makes people feel a certain way. And I haven't touched that side of life in a long time because you focused on commerce and you focused on the web and you focused on software and money and businesses and B2B

So in

space, would you want to get into a business that sells products to professional chefs or to people who are serious about, you know?

I don't know. Don't. I don't know what that means. Don't if you

to start a restaurant.

Don't think I would start a restaurant because that's almost like it's so obvious, the pain, it's right in front of you. It's like you already know before you even start what it means.

Have you watched Bear? Yep. The show?

Yes. Fantastic show. Here's the thing. When I watch that show, I would want to be in the business of creating shows like that. Exactly.

Not actually opening a restaurant.

The restaurant looks like a total nightmare, but the show is incredible.

It's almost like, how could you be the basically the owner, the one that puts this together and brings the money and the director and the producer? At the end of the day, like what your company does is create, it helps put together the people that create the end product, whether that's a TV show or something like that. I don't know if it's that or ends up like a direct to consumer type of a product business, but I'm just interested in that one.

It's an interesting question of whether it's wise or not to get into a business that tracks with your personal hobby or interest. And like, I almost did this back in 2015 when I was in, I I had sold Restaurant Engine and I was exploring ideas, which ultimately became Audience Ops. But before I settled on Audience Ops, I was very seriously looking at avenues into building a business in music. And I still think that there are opportunities there, like for professional music producers, and because the landscape of music needs in the whole world, not only on television and film, but now on the internet and video games, which has all exploded in the last few years, there's a huge industry of producers who compose music for that stuff. And then all those people like buy thousands of dollars worth of gear.

There's affiliate marketing opportunities. There's training. Again, there's coaching, there's community opportunity, all that kind of stuff, software, SaaS for that crowd. And these are not struggling musicians. These are career music producers who creates media like music for media.

You know?

Yeah. Right. The intention behind it is to make your life more involved with it. Yeah. And have that be a bigger part of your life.

I feel like I've rediscovered my love for playing guitar and playing music because I am intentionally like, that is my hobby. That's not my business.

I don't really, I don't know if I care for the separation.

Yeah.

Because whatever I'm doing right now, what I'm obsessed with is like, how will you change nature of platforms and ownership in the e commerce world? And like, I like my life being about that, and my business being about that. And I'm endlessly interested in it. And I'm happy thinking about it all day. So it's kind of like, I don't really need the separation to be happy.

I'm actually quite happy to not have separation. And just think about the same thing all day and dive all the way into it. I'm fine with

that.

I gotta be, I've always been super impressed with my buddy, Chad Deshaun. He's the founder of boardgametables.com, which is a tremendous business now. They're like the leader in that space. It's incredible. And so they started with like custom built high end board game tables, and then they got into like mass manufactured tables and now they actually produce and create board games.

You know, we're not talking about monopoly. We're talking about like niche, but it's a huge gaming industry. Right? And he's a guy who started out in just SaaS. He built and sold a previous SaaS and then he just decided to go into his hobby and build a business and like dominate the industry.

Like it's incredible.

So

Chad, awesome dude.

Yep. I'm looking at the site now and I remember meeting him at a microconf, must have been close to ten years ago.

Yeah. He's an every year attendee of Big Stone. That's right.

So like that, I don't think I have any problem with that. I don't need to separate anything. Yep.

Yep. Then of course, and crypto.

What do we got? Are we wrapping or you got anything else?

Yeah, don't know. You got anything else? This is a free flowing. Anyone who's still hanging out with us is just hanging out. So shout out for hanging out.

Let's see if we want to hang out anymore. You got anything else? I really like the format these days of podcast hangs. There's the bar stool, like bunch of dudes hanging around thing. The truth is you actually find a lot of this on TikTok because they use it for distribution and there's all types of podcasts.

So a lot of things on TikTok are just video segments, you know, thirty second to two minute videos that are podcast recordings. And what it does is it gives you a glimpse into their conversation and their personalities. And then you might wanna listen to the podcast. I've found several podcasts like that.

I'm gonna do a shameless plug of my other, it's a newer podcast that I started earlier this year called OpenThreads. What is it? It's openthreads.co. I don't even know the website, my own thing. I haven't been very promotional of it except to my newsletter, but I'm having fun with it.

What you just said, like these like podcast hangouts. I just wanted something as much as I love doing this show with you, which I hope we do forever, you know, I just wanted another excuse to hop on the mics with all of our other friends, like founder friends, to talk about a range of different issues. And there's obviously a lot of episodes about business, but like there's a lot of stuff in there that is non business, like getting into other topics, whether it's music or politics or family or location independence, like all this different stuff. So my approach over there has been like, A, just an excuse to stay in touch with people I find interesting and I wanna talk more about cool stuff with, but also like I to nail down like one or two key topics to focus on, not just like a random episode, but like, and not like your life story. It's just like one Yeah.

Thing per Right.

Yeah, I'm sometimes coming across podcasts that have massive audiences. And then I'll listen to the actual show. And I'm like, these people are not talking about anything. They are just kind of existing on a mic. And people are identifying with them because they are like them.

And the only way you get there is if the people are just being themselves. And if you come across that and it's not for you, like, that's fine. It's unintended to be for everyone, But there's definitely something happening there around like just being online more and letting people get to know the real you more is the way toward the real audience.

Yeah. I know we probably got to run here, but another thing that I've been thinking about on that note of like just being public, like working in public, building in public, obviously something that you and I both have been doing for many years now. I feel like on Twitter specifically, I'm still on it every single day, but I'm like less active or less intentional about the content that I put out on Twitter. And it's mostly because I don't have like the time to really think about it or be strategic about it, but something that I keep thinking about. Like, maybe if I could like set aside like once a month, just like actually like draft out some thoughtful ideas that I can put out.

I don't know

what to post anymore.

Yeah.

I don't know. I'm with you. I still love Twitter and I'm a consumer and I look to it for news.

I'm not trying to debate. Not trying to post something.

Right, who wants to

argue? That's, I can't stand that. That is so annoying on Twitter. And just don't wanna debate and and that's and I try not to provoke that, which ends up being like, I end up not you know what? I end up not tweeting because it's like, alright.

Here's here's an idea that I have, but here are the 10 annoying responses that I know are going to come.

So you're so you're stopping yourself right from it, which is kind of like the that's the ugly side of what's happening psychologically to people as they look to Twitter and what to post. And it's the people who want that or don't care or are intentional enough about their promotion. It feels very strange to like decide to go on Twitter to fight with people, that feels ridiculous. It also feels it's so off putting to me to go onto Twitter to brag. I don't want to brag.

I just want to talk. I just want to see, like here's this interesting thing, or here's this new thing that we just did and kind of let people know about it, maybe get some response. But it is a bit of a strange place. Some people are very, very good at it and it feels like they're the ones that continue posting and are getting all the attention rightfully because they're really good at it. But it doesn't feel like people

People always naturally retweet and like the big MRR graphs and stuff. And then people get rewarded for that and the algorithm and all that crap. But like I do the build in public thing, but not because of any strategy. It's just because that is the most interesting thing to me. Like sharing something that I just worked on creatively, technically in the business, on the product.

Like, I want to see more of that from other people. I want to see behind the scenes in real time what you just shipped and why you shipped it and your thinking behind it. And to me, that's not bragging. And, you know, yes, I'm showing Zip Message, but I'm not trying to like necessarily market it in that way, although it has an effect on marketing. It's just like, look, this is what I work on every day and what I think about, I'm networked with a lot of other smart product people, but show your work, you know, like show what you're working

on. Right. I have found that that happens much more freely in closed off communities. It's just kind of a reality. And that's why I like am hungry.

You know, when someone is like, do you want to join my Slack group? I'm like, yes, I want many Slack groups because that's where that's where I see it's a lot where where my socializing happens. Yeah. So I'll see tweets and then I'll bring them into my Portland Slack group. And then me and Ruben Gomez and John from Roaster Tools will kind of really get into it.

And then we'll ask about, well, Jordan, what are you seeing on these new salespeople that you hired? Like, what's that going like? And then Ruben will say, oh, I just heard from this other founder. And like, then you're really getting into the good stuff. And it feels like you just can't do that in public.

I think Ruben is like the common denominator in like every Slack group. He's in the one that I'm in and like all of them like are like that. Like, yeah. And totally like and that's where we go talk politics and go talk all the shit that

Right. Because you can be more honest without worrying about responses and you can find some nuance and you don't have to be worried and anticipating what the comments back are.

Yep. Yep.

Also, I'd love to work a lot less. That's how

I People say that. That's one of things that people brag about on Twitter is like how much they're not working or they're going on sabbatical or this or that.

I'm Honestly, like here's my summer house, this ridiculous multimillion dollar amazing cabin you built. Keep that shit to your fucking self. What are you doing to people? It's not cool. You know how people feel when they see that stuff.

And I almost look at it and I'm like, I remember myself ten years ago when I didn't have the same resources and comfort that I have now, and that should make me feel horrible. And now you think I'm going to post my like. Now that I finally have like this,

Yeah, it's just like a jealousy bomb.

Yes, it's just throwing out there. It's like, you know what it is? It's like inverse jealousy. It is getting joy from creating jealousy in other people. It is disgusting.

And anyone, when I see that, I just fucking block it immediately. I cannot stand that.

While we are ranting about things that-

I got pissed off there. Did you see that? I got all pumped up.

Dude, know what it gets for me? The thing that really gets to me, because I have been affected by this and then I've learned to deal with it mentally and block it out mentally, which is, and you see this all over Twitter, especially in our circles, which is like and look, everyone is well meaning behind this, but it has an effect, which is putting out a vaguely worded tweet of like what not to do. Like, don't do this. You're making a mistake if you do it this way, or if you build a business that way, or it'll say something like, I see a lot of people making this mistake. Okay.

Like, first of all, it's so vague that you can think of like a thousand different, like, well, what if this or that situation? So you'll go crazy parsing all the different, if this, then that. Second of all, you thinking might that you're tweeting to a certain person or to a certain group of people who are clearly making that mistake, but there's such a wider range of people who are going to interpret that as like, oh, maybe they're talking about what I'm doing. Now I'm going to self question what I'm doing. Maybe I'm doing the wrong thing.

And of course, there's no taking into account each individual person's background experience, information that they have in front of them.

So you get mad over the bad advice.

But the thing is that it might be good advice, it might be bad advice, but it's way too general for a tweet and it's going to affect way too many people in the wrong way. That like a maturing unintended way.

Yeah. Yeah. It's almost like I mean, that is no way to build an audience.

I just think that there's an alternate way to give the same advice, which is like, you could either be negative or you can be positive and more constructive. Right? You either say like, you can either go negative and say like, don't do that. You're making a mistake if you do it this way. Or you can say like, here's something that sort of worked in this case.

I found success with this. Like maybe you might too, maybe you can take a kernel from this and use it in some way. Maybe not. I just wanna share it and share it publicly. And maybe you can find that helpful.

The sharing, the humble sharing of lessons learned with caveats and nuance is like doesn't do well. Well, hopefully, hopefully something comes along next. You know, hopefully some some 40 year old creates like a like a link. Excuse me. I said LinkedIn.

I was going to say TikTok, but LinkedIn mashup for, you know, for professionals or something or other.

Yep, yep, yep.

Or we'll just co op TikTok and we'll flood it with old people like ourselves talking about business instead of doing dances.

Well, Jordan, I think we've outdone ourselves on like maybe the most random Bootstrapped Web episode yet.

Yep. Who knows? Look, this is a good reason we don't take sponsorships.

I'll sponsor my TikTok.

Yep, there

you go.

It's good

to see you.

All right. Yeah.