Justin Jackson - A conversation with the zen-minded bootstrapper!

Now, I'm quite interested in helping people make better bets and helping people think in the present and the future about how they can be mindful about what they commit themselves to.

Hey everybody, welcome to yet another episode of the Undefeated Underdogs Podcast. I'm your host, Sharath. Today, I have like a very special guest who I admire a lot as a founder, and I've learned a ton from his newsletter, from his podcast, and just his tweets. You know, he's none other than Justin Jackson, the founder of transistor.fm. Justin, thanks for taking time. Welcome to the podcast.

Thanks for having me. It's fun to be here. I was telling you earlier, I've listened to a few episodes of the podcast. I'm really enjoying it.

Thank you. I appreciate your time. For folks who doesn't know Justin, let me give you guys like a brief intro. Justin is a veteran entrepreneur, founder, podcaster, blogger, and he's a dad of 4, which I want to cover later in the episode, and a phenomenal community builder. I love the way you built Mega Maker, by the way. Thank you. the bootstrapper community called Mega Maker. He hosts a podcast called Build Your SaaS and writes about bootstrapping, you know, in his newsletter, which he covers about mindfulness, meditation, habits, you know, many other things. So Justin is, in short, is a jack of all trades. And I'm so glad to have you, Justin. I do have like some notes I've prepared for you, but right off the bat, I wanna, I wanna— dive into your origin story. Let's go back to your, I think, 20s, I guess. I read somewhere when I was doing research on you that you started as a founder of a brick-and-mortar snowboarding shop, I guess, if I'm not wrong. So tell me about it.

Yeah. And then after I graduated from college, I took business in college. And I did my practicum, my internship at a snowboard manufacturing company. They manufacture snowboards and skateboards in Alberta, Canada called Olive. And I was there for, I think, about a year.

Mm-hmm.

And then went back to university to finish my degree in business. And after I was done, I was working. in the nonprofit sector. But I had always dreamed of running my own shop. And part of this was because I grew up in a small town. And, you know, when you grow up in a small town, the, the only kind of entrepreneurialism you can see around you are people who own shops on Main Street.

Right.

And then working in the snowboard and skateboard industry on the manufacturing side, I was always interacting with shop owners. And just as a snowboarder myself in high school, it's kind of every kid's dream to run your own shop. It just seems, you know, to be the coolest. So I started it with my friend Adrian and—

Nice.

We were both working other jobs at the time and we hired my brother to manage it originally. And then Adrian later managed it. And it was interesting. It, it, it was— I think I learned a lot through that process. You know, one was that I wasn't full-time focused on it.

I

was working in the nonprofit sector and would kind of do shop stuff on the side.

Mm-hmm.

But this was kind of the beginning of me learning about how the market Actually, everything that's encapsulated in a market kind of determines how your journey's gonna go, how much momentum there is in the market, the dynamics of that market. And so, you know, running a small snowboard skateboard shop in a small town, you've got market size issues.

Mm-hmm.

You've got profit margin issues. You've got all of the logistics and difficulties of running a brick and mortar company. Mm-hmm. And so, the net result of that was when we closed the shop when I was 25, so I think maybe 5 years later or something, we had lost quite a bit of money. I think it was about $80,000. Wow. And as someone in their early 20s, that was just— it was an expensive lesson. to learn, which made when I got into the software industry later, so that was 2005, I got into the software industry in 2008.

Right.

I could not believe how much simpler it was and how much better the margins were.

Right.

It was just not simple in terms of like, it's easy to start a profitable company, but simple in terms of just the logistics. You don't have to— order inventory. You don't have to worry as much about cash flow. You don't have to hire as many people. You don't have to deal with all of these things.

Theft.

Correct. It was just a simpler business to run. And, you know, I was— my boss, my first software boss, was kind enough to kind of show me the ropes and show me the profit margins in software. I like the profit margins in, in like retail. If you're lucky, you buy a t-shirt for $15 and you sell it for $30.

Right.

Those are your variable costs. That's if you're lucky. A lot of stuff is like 30% margins. But the overall cost of running that business, the, the, the lease, the fixtures, the lighting, the electricity, the employees, the theft, everything. It's, you know, SaaS margins are like 80% plus.

Of course.

You know, it's, it was just blew my mind when I saw that. So, it's nice having the juxtaposition to get that out of my system early and to have the juxtaposition now or back in 2008 of seeing like, wow, this is Quite a bit different.

Right.

And also that, and coming from the nonprofit sector, seeing like we worked so hard in the nonprofit sector, just very, very hard, put in so many hours. And working for the software company felt, definitely felt like easier. It wasn't as much.

Yep.

Just kind of grind, you know?

Right.

So yeah, both of those things together, I think, right, I kind of got woken up to the software industry in 2008. And, and having those experiences working in nonprofits, working in retail, it just like, the juxtaposition was so clear.

Yeah, I mean, I think every experience counts, you know, that's what I believe in. Doesn't matter It doesn't depend on the outcomes. It depends purely on how you went from A to Z and what you've learned and kind of what you realized from that experience. That's what really matters mostly.

That's right.

And it might be a costly mistake, costly affair, which you said, like the $80,000 at 25 years is like a bigger thing. It feels like millions at that time. But I feel turning back, I feel the lessons you've learned and the moves you made now is much more wiser. You became wiser, you became smarter and whatnot. And funny enough, you said that I really appreciate you actually acknowledging it, the fact that you failed and you turned into something like a SaaS and you actually like you're becoming successful here. As a founder, I appreciate the transparency. And, you know, like you said, it's— I never dealt with brick and mortar, but I can actually kind of imagine the stress, the pressure, the quality check of the product. You know, sometimes it comes broken and, you know, whatnot. So kudos to you for navigating from, you know, there to here.

Yeah. I think you're right that when we're looking back on experiences that we've made it through, the only thing we can really do is just be at peace with them and go, okay, what did I learn and how am I going to act in the present?

Right.

There is a danger, though, in the present looking forward. I think we do want to be mindful about the kinds of risks we take and the kind of bets we make. Because I made it through, but it's, it's, it's quite possible that, um, uh, it's quite possible that I, I, I might not have. Mm-hmm. Yep. And, um, in some ways there's some survivor bias here in that I, I made it through that, but there, there's a risk with anything you commit yourself to,

right,

that you're going to burn out. Or get crushed by it.

Right.

And in that case, that was $80,000. And it just happened that we were in an up housing market. So, I was able to remortgage my house, which wasn't fun, but I had the means to come up with some money. And then I got lucky again. I got this job offer from a software company and I was able to work my way up in there. There's just a series of fortunate events that happened as well that helped kind of— that helped me make up for the bad bet that I'd made.

Right.

Yeah. And I'm—

Right. Yeah. I think you're right on that front. I would like to add like 2 cents of mine, which is I failed. I also not an $80,000 failure, but I did build a B2B business, which I'm not a customer of and not my problem, like burned my hands. I was just getting a job in the US. I came from India and I spent, like, with a friend, $16,000. We outsourced everything because we were a bunch of non-technical guys, but we have this ambition of building something. we fail miserably. To add to that point, which you said, you have to make a calculated bet from the lessons you've learned on top of it. I think those who have the ambition and the drive to do something, even though they failed, those are the people I think move forward. And in this case, you actually moved forward because you wanted to do something in life. It's not like the end. So I truly believe in your best is yet to come. It's always yet to come. Now, what you do right now is it's a work in progress, but it's not your best. Your best is in the future. So I try to chase that more when I do projects or take up any ideas. I tend to think like, yeah, What can I do better from my past experiences? Number one. Number two is, yeah, this is not my best shot. My best shot is like, you know, it's still there. So, that kind of eases me out.

I like that. I like that. I think having an orientation where you're kind of positive about the future is good. And an orientation where you're willing to keep trying things and keep being in motion So, I think this idea of being in motion, trying things out, almost all my friends who have been successful in the software business were doing— they were in the midst of doing something else when the idea for the business that worked came about. Exactly. So, my buddy Adam Wathan was like, he was building a SaaS app publicly. And he's live coding it and people in the comments just keep asking about how he's writing CSS. And eventually he's like, well, I'll just, you know, create something that helps people write CSS the way I do. And that became Tailwind. And now Tailwind is possibly the most successful, one of the most successful indie projects ever. It's wildly profitable. Right. But he found that idea while he was in the midst of doing something else. He was in motion. And there was lots of things that he was trying that didn't work out, quote unquote.

Yep.

But the idea is to be in motion with an orientation towards, yeah, I'm just like experimenting, trying things out, not overleveraging myself, not over-risking myself, taking appropriate steps each step of the way to determine what's next. Right. There's a quote from Richard Branson where he talks about how he figures out what to do next. And he talks about it like dipping his toe in the water and seeing how it feels. If it feels good, he goes in a bit deeper. If it feels not good, he gets out. And there is that one thing I do see some people do is they come up with an idea and then they just commit too much to it.

Right.

It's, it's like they're, they're like, no, this is the idea that's going to work for me.

Right.

And, you know, we see these folks all the time, the person in your town who's been running that business on Main Street forever. It's not making money, but they're just so invested in it, they can't get out of it.

Right.

And we don't want to do that. We want to be in motion, be trying things out, not risk what, you know, make appropriate risks and, and, you know, just keep searching for the thing that gets the big response. And I also, I also would just want to temper one thing you said, which is I think it's good to be positive. about the present and the future. But I think we also need to be realistic. Absolutely. And, and the, the— sometimes I even get pushback about this. Like, people get upset when I introduce any idea of like being— bringing some realism into the process, but just being realistic. You know, when I opened that skateboard snowboard shop, like being realistic about how many people really are here With money to spend and what are they doing already? And it turns out they were just going to the big city 20 minutes away.

Right.

So, if that's what's happening, I need to be realistic about that.

Right.

And too much magical thinking, too much like, you know, I'm going to harness this Steve Jobs energy and just like bend the universe to my will.

Bend reality.

It's not healthy. You need to have some realism. Oh, yes. And I think it's easy for us to delude ourselves.

Absolutely.

And that's why we need good partners. That's why we need accountability groups. That's why we need people who are willing to call out our bullshit and say, hey, I'm glad you're positive about this idea. I'm glad you're trying it out. I'm glad you're experimenting. But Here's— let's look at how realistic this is.

Exactly.

And be very clear about that.

Yeah. It boils down to a lot of qualities like self-awareness, what we're doing, what we're dealing, where we are, how risk assessment and all that. It's more of like, I think that's why I really admire founders who are self-aware of what their situations and yet, they want to take a chance, move forward, take a step. Yes. And self-awareness, it's one quality. The other important quality is actually keeping your expectations low. The next thing you do is not the next big thing. That's why you should have a lot of fun, ultimate fun, have the joy of enjoying the process going from A to B to C to D. That's it. Like, Z is this goal, which is like, which is a bubble in my opinion, which can be achievable or can be like, you know, can get into a burst. So yeah, having that self-awareness with kind of like, you know, having zero expectations is something like a balance a founder, a lot of founders should do, you know. And to your point, it brings It actually brings the best of it. That's the equation or the formula, maybe, you know.

Yeah. Yeah. I think I like that too. Although, on the other hand, see, so many of these ideas are held in tension. So, it's true that keeping your expectations reasonable, like, oh, you know, when we started Transistor, John and I were like, this might not work. This might not make any money. This might hit $1,000 in recurring revenue and then stop.

Right.

This could all be gone tomorrow. We say that all the time. So that's true. It's good to have low expectations. And then as things progress, it's like, oh, wow, this is better than what we thought. That's, that's great. But on the other hand, it's also good to have It's also good to seek what you want. So it's a, it's an odd tension because when we were starting Transistor, I was trying to keep my expectations low of, you know, I, who knows, this might work, it might not. But on the other hand, there was definitely something that I was seeking that I wanted.

Mm-hmm.

I wanted financial freedom. I wanted to build something that was high quality that many people used. I wanted to, you know, for John and I to build a company that gave us a better life. So, you're kind of holding all of these ideas in tension with the other thing. And part of it is timing.

Oh, yeah.

The right advice at the wrong time is wrong advice or something like that. I think—

So true.

I think that, and so many startup truisms are like that. You know, it's like you can give people advice and say, well, keep your expectations low, but maybe for the timing of where they're at, they actually need to be expecting more from their ideas. And, you know, maybe expecting more from an idea might mean, you know what, I've been doing this for 2 years and it has not met the bar for what I needed or wanted. And so now I need to get out of here, right?

Right, right.

I need to stop keeping my expectations low. I need to raise my expectations so that I can get rid of— get ejected out of this, this bad idea.

Yeah, absolutely true. So you've touched on a very, very interesting point, which is you have to seek, you have to talk to the universe in a way, you have to like put your intentions out. You have to manifest. That's all. Like, that's what I'm hearing from you. That's in the last couple minutes.

I mean, I wouldn't put it that way, but I understand the idea. I mean, that might be a little too woo for me. I think if by manifest we mean we're just engaging in a process where we're seeking out something that we want and we're going through a process of being in motion to keep trying things, iterate, find, you know, the opportunities that are a good fit for us and for what we want, then yeah, I think that's the path.

That's what I meant. So, okay, so let's go back to Canada. You burned $80,000, shop's closed. You're done, wrap it up. At that time, what were you seeking and what led you to join a software startup? That's like your next in 2005 to 2008. What was in your mind?

I mean, for most of my life, because we had kids so young, we had our daughter when we were 22. The most immediate thing was I just need to provide for this family. And Ben Ornstein jokes about it. He says, I was living life on hard mode. And it's true. Right. I wouldn't even necessarily— I wouldn't recommend this path for other people because It just, you know, from the moment we had our daughter, I realized that, you know, making $36,000 a year working for a nonprofit was not going to be enough money to survive. And so, a lot of my seeking in all of these years was 2 things. Purpose, you know, how how can I have work and do engage in activities that give me a sense of purpose? But then the second one was how can I make enough money enough money for my family? And for a lot of years, it was just how can I make enough money to for us to be you know treading water. Like, how can we just raise the income so we're paying most of our bills? And then once I hit that, then it was, you know, how can we not just have, you know, enough to merely survive, but how can we have enough money to thrive and, you know, to live the best possible life we can? And so, I think that's actually Between purpose and having enough money to survive and thrive, I think that's led a lot of my seeking, right? Like, I got a big raise when I started working in the software business. I got a much— I was working so many hours before, like 60 to 80 hours a week. Wow. when I was working in nonprofits and then to go to a software job where it was like 8 hours a day, but we got an hour for lunch and it just started at 9 and it ended at 5. And then there was an hour-long lunch break in the middle. That was, so, yeah, I think those, it's actually 3 things. It's a sense of purpose in my work, this idea that I'm contributing to the world in some sort of meaningful way. Financial, just making enough money for the family to survive and thrive. And third, now I lost it.

You're talking about time, the luxury of—

Yeah, the third was to maybe— oh yeah, the third was just to have a better life for myself, you know, to have more more peace, more time, more calm, more margin in my life.

Being more mindful in a way.

Yeah. And, and, or just even having more, having the space to be mindful. Like when, when you've got 4 kids and you're working 60 to 80 hours a week, you just have no margin in your life to be anything, to be mindful, to, to have peace, to have calm. So yeah, that was what I was seeking for sure.

I think let's go a little deeper on this topic, which one of the questions I have, you're also very big on mental health, being mindful. You wrote a lot about that in your newsletter, Quiet Times. So how are you managing from 60 to 80-hour week to what you're doing right now? Even now, you, I assume, work really, really hard. It's not easy to maintain a podcast and a newsletter and running a company like Transistor.

I don't work as hard now. I don't work as hard now. That's one of the big changes is that, and this is something that it's one reason I'm so excited about indie businesses. Because my friends who are in the startup world or my friends who are in the tech, corporate tech world, they're to, to earn more money, they need to make this awful trade, which is they need to work harder. They need to have more stress. They need to spend more hours at the office. They need to give up more. They need to sacrifice more.

Right.

I think it does take hard work and sacrifice. To,

of course,

achieve good things. But at the, the, for John and I, the aim was eventually we want to get to a point, not where, not a point where we become complacent or lazy, but a point where we just have tons of margin.

Hmm.

And, um, you know, there are people working in agriculture jobs, picking strawberries, picking apples that are working 100 times harder than I am.

Of course. And they earn, of course, less than what you, what you make.

That, and, and making less money as well. And I think there's not, there, there isn't a direct correlation between hours worked or hard work And even what is hard work? You know, like I'm in here in an air-conditioned office and, you know, right out my door there's people fixing a road that are working way harder than I am in way worse conditions. So the goal for us was eventually And, and with mental health, this is actually my desire for everybody. Mm-hmm. Whether you're fixing roads or running your own business or working for a big company, is that everybody would be given the margin to have peace and calm and space in their life. So, as an example, this call that you and I are on is the only Meeting I have today. Tomorrow I have a meeting with an old friend. Thursday we have our staff meeting. Friday I'm recording another podcast. But and this is a busy week for me in terms of meetings. One meeting a day. That is calm. There's space. I've

right.

I've got um. I had a bad sleep two nights ago. And I decided to sleep in. You know, I woke up at 4 in the morning, couldn't get back to sleep, finally got back to sleep around 7, and I just slept until 11.

Hmm.

Space, margin, calm. That's the aim. And this seems to be a feature that's only present or is primarily present in indie businesses where the founders have mindfully shaped the business to produce this kind of calm.

Right.

And this isn't just calm for John and I as co-founders. This is also calm that we want our employees to have as well.

Sure.

And I think we've accomplished that so far. And I think— I hope that this is attainable for more people. What originally set me on this path was this old article I read in Fortune magazine, I think, from the founders of a bread company. And it was called The Good Life and How to Get It. Yeah, I read this back in 2000 while I was still in college. It's about the founders of the Great Harvest Bread Company. You can find it on my blog if you search Justin Jackson and The Good Life. And this is the quote that really resonated with me.

Hmm.

When all your choices are made with freedom and simplicity in mind, then freedom and simplicity is inevitable. And so this couple that started this bread company, which is a brick-and-mortar business, which is you know you have all of the you have equipment that's expensive, you have employees that are expensive. They they they purposefully shaped the business so that they in the beginning, in the early days, they always had a two-day weekend.

Mm-hmm.

And that combined, the two of them worked about 50 hours a week. So, 25 hours each.

Hmm.

And they didn't talk about work at home. So, they set up these guardrails as they were building the business, as they were crafting the business, so that they didn't have to look like the trope of a business owner who's somebody working 60 to 80 hours a week and is always stressed and always has lots to go and must fill up their calendar with a billion meetings to look important or whatever. You can just do it a different way. And it's been— again, there may be a time where I have to hustle again.

Mm-hmm.

Like I did, you know, in some of those early days. There's— there is a time to hustle. There's a time to sacrifice. There's a time to work hard. There's a time to grind, but you can't do that forever. And I'm— I really want people to know and feel how good it feels to have gone from being that person in my 20s who was working 60 to 80 hours to, you know, trying to build a life like the one I have now, it feels so good. It's so calm. It is. It's just the peace that I have, the space that I have to explore, to be mindful, to think about ideas, to engage in relationships, to be there for my kids, to be there for my friends, to— It's just a life with no margin is is is not. It's you're just constantly running just to keep up. You're constantly treading water just to keep your head above water. It's not a good feeling. But when you have space in your life, you can. You know, I have a friend whose wife is going through a a really hard medical. thing right now. And I was able to say, hey, listen, I'm— anytime you need me, you need me to pick you up some food, you need to call me for 3 hours and talk, you need me to bring over some beers and, you know, just chat with you, you need me to watch the kids, I have space to do that. And that this life that I have right now is so good. And I think you can hopefully, I think it's accessible to more people and that's what I desire for them. And for people to not always assume that a business owner has to be this person who's always busy, who's working hard, who's stressed out. Again, a lot of my founder friends who own indie businesses, especially who have bootstrapped,

Mm-hmm.

They, you know, they might work 3 hours a day, like actual, like work, you know, like actual I'm coding or actual whatever. It doesn't— it's probably less than a lot of people think. And I think that's a good thing. I think it's a good thing for— Yeah. us to kind of cultivate that kind of culture.

Right. No, for folks who are listening and who can't see Justin's face, I can 200% tell the level of peace and calm in his voice, in his face. I feel like, you know, and bootstrapping in a way makes you your own boss. You decide what to do. You decide like you know when to stop, when to kickstart, when to hustle, and that's like the the the the good thing about you know owning your own business and owning your own equity in your time and whatnot for yourself, right?

Mm-hmm.

I absolutely love.

And by the way, it also doesn't mean that we're moving slow.

Right.

The the the benefit of a small team is that a small team where everybody is putting in a good. 3, 4 hours of focused work a day and doesn't have all of the other distractions that can be involved in company life, we can ship really fast. We can have a really nice release schedule that, you know, compared to our bigger competitors, our Our pace is faster. So, they're working harder. They've got more meetings. They've got more on the calendar. They're putting more hours in at the office, but they're achieving less. There's not a direct correlation between hours at the office. I mean, Patio 11's talked a lot about this in the Japanese salaryman culture where you're just expected to be at the office for— whatever, 12, 15 hours a day, but they're not expecting productivity. They're just expecting you to be there.

Be there. Yeah.

Let's flip that around. Let's, let's be productive when it counts. And then let's have space in the margins to do everything else.

Right. Yeah. Let— I love, I love that. So many incredible takeaways in the last 5 minutes for founders who are especially like, you know, bootstrapping and juggling between things. I love certain values you've told us right now. Let's kind of switch gears a little bit. Let's talk about your reason why you get into SaaS in the first place. When did you fall in love? When did you saw like, you know what, let me do this versus— you know, I don't want to go venture. I don't want to raise capital. I don't want that stress. Where was like the transition that happened? Like, you know what, this is it. Let me actually go all in into bootstrapping and into SaaS.

Yeah. I mean, it probably started because the first software company I worked for was this company called Mailout in Edmonton. It was like a Mailchimp competitor.

Mm-hmm.

And they were bootstrapped. And I think my first week on the job, my boss sent me a copy of Getting Real by 37signals. And I read it in an evening. Mm-hmm. And just every one of those essays was just, I was just like, it resonated so strongly with me. Like all of these principles. And, you know, some of it's quasi-religious. You know, there's a little bit of cult around 37signals Basecamp. Right. But there, just those principles resonated with me so strongly. And, you know, since then, that was 2008, it took another 10 years before I was able to launch Transistor with John. And there was lots of steps in between. Right. But I think it was always there that, wow, these are great businesses. Hmm. And you can run a business like this differently than the way a lot of other people are running their businesses. And, you know, so Basecamp was an early model. Peldi at Balsamiq was an early model. Right. Derek Shivers was an early model. These were all— yeah, Mailchimp. Yeah.

Right.

You know, these were all principled founders who, you know, self-funded these businesses. And I— there was just something about that ethos That really resonated. So, yeah, it did take a while because I think, you know, actually starting a successful software business is not— there's a lot of things that have to align in order for it to work.

Absolutely.

And so, you know, in the in-between years, I was in motion just trying things out, just doing things the best I could, just, you know, iterating through different jobs and different ideas and different experiments. But then, you know, when Transistor came along, just a lot of things aligned. And it's not, it's not a crazy growth market. You know, podcasting has grown about 10, 15% a year for the last decade.

Hmm.

There's, there's Arguably, I think there's like 4.5 million podcasts or something, but there's arguably maybe 100,000 to 150,000 that are actually in active production.

Right.

So, the numbers are very low. There's probably something like, I don't know, 60 million YouTube channels with more than 10 subscribers, and there's probably 500 million blogs that are still being actively, you know, published on. So podcasting by comparison is small, but it was a big enough opportunity. Hmm. And it felt worth pursuing it because it aligned for Jon and I in so many other ways. It was like, there's enough demand here, there's enough people paying for podcast hosting. And, you know, Jon had previously built a podcast hosting company, so that helped. I had been podcasting since 2012. I was, you know, I developed all these product and marketing skills. John was developed all these full-stack development skills. We had this network from a lifetime now, you know, decades in tech. We had audience, we had, and then just the podcasting itself resonated with us philosophically. It's slow. technology. It's mindful technology. It doesn't depend on ads and, you know, addicting people so they're scrolling all day. You know, it doesn't, it doesn't depend on an algorithm to, you know, get people addicted and to work. You know, it's just very slow, mindful technology. And with all of those things in place,

Right.

And, you know, we hit the timing. There's just so many things you need to have hit right. But

I know

that it was enough for us to kind of build a company that made it work.

I love that. I love—

yeah, you never know what's going to happen tomorrow. But for now, it's working.

Yeah, I love that. Congrats on all the, you know, all the persons converting all the personal experience into like a product and productizing it so that People like me, we are— I'm using Transistor, by the way. Shout out to you guys. You guys made my life so easy on one tap of a button. Again, this is not a sponsored thing, but I'm genuinely loving Transistor because with one tap of a button, you can distribute like, you know, to every possible podcast channel out there. And that's it. And so easy to use, so intuitive. You know, it doesn't require like a lot of Learnings. And this is my first time ever doing podcasting, and I'm just— it actually reduces the friction for me as a podcaster, and that allowed me to focus more on writing questions, finding guests, interacting with them, having an authentic conversation. Earlier, it used to be like, I have to go— at least there's an amount of friction you guys are taking away. Which you know I'm thankful for. So congrats, and that's so great to hear, guys.

Oh, that's so great to hear. I appreciate it, and I appreciate you, you giving us a chance and trying us out.

Absolutely.

And and that and that feeds into the purpose part we talked about earlier, right? So if you can build something that can give you a good life, that can create the margin you want, you you have this foundation. To have this purpose of serving customers, of making their lives better, of having them hire your product to do a job in their lives. And for that, and then for you to actually do the job well, you know?

Right.

That is so just wonderful. It's just wonderful to have that role in people's lives. And for me, I'm a fan of podcasts. You know, when you launched your show, I was excited to hear it. And we have, you know, we have thousands of customers, but it's— the number is low enough that I can still check out a lot of people's new shows.

Correct.

And be a cheerleader. And, you know, just, it's almost like I get as much joy from seeing other people podcasting and getting something out of it as I would if I was podcasting. Myself, you know, it's just so gratifying to be involved in all that.

Absolutely. That's the word. I think I genuinely feel, I genuinely want founders who are listening to this podcast, you know, feel what Justin is feeling, which is you genuinely have to care about your customers. That's one other thing I really admire about you, Justin. 2 instances just for the sake of this conversation is number one, when I approached you, I'm like trying Transistor for the first time. I really asked because I'm in the area of making podcasting as a hobby because I don't have a ton of money as a sponsorship and whatnot. And you gracefully instantly replied me with a code. That's number one. Number two is— when I'm having some certain issues with the website, you were right on top of it. You were chatting with your team, sending screenshots, helping me, even though technically it's not your headache. You can just say, you know what, use it, or you go find another website builder, build your website. And that to me is really important. And that to me is really a lot of founders should do. And I did it in my bootstrap product called Shoutout is giving personal attention, like one-on-one attention right there when a customer is asking or seeking help. That speaks volumes of what you believe in, and that speaks like truly, you know, you enjoy and take pride in what you work at. So yeah, I appreciate you for both instances. Oh, that's great to hear.

Yeah. I mean, this is actually an essay in Getting Real by 37signals. It's, you can't fake enthusiasm. Right. So, this is why, you know, when software developers sometimes approach me with ideas and they're like, oh, I'm building an application for real estate agents. And I would say, well, like, do you like real estate agents that much? Like, are you— do you like that industry that much? Do you really want to serve those people every single day? You want to, you want to answer their emails, you want to answer their support tickets? Like, that gets you fired up? If it does, go for it.

But just go do it.

Yep. You can't fake enthusiasm. And that enthusiasm ends up being a competitive advantage. So, you know, sometimes in a lot of these markets, you know, you're as an indie founder, especially, you're gonna like be trying to get to feature parity with whoever the big company is, or, you know, at least some level of feature parity. And people will ask you, well, why should I go with you over somebody else?

Hmm.

And sometimes my answer is just, I, I care more.

Yeah.

We, we care more.

Right. Absolutely.

The CEO of that publicly traded company that you're thinking about going with is not answering support tickets.

Yep.

At 11 o'clock on a Friday night. I am. I'm doing it. And, uh, again, and I'm doing it with margin and calm and I'm not overworking myself.

With intention.

But we care. We just care. We're passionate. We're enthusiastic about This, this whole category. It's why I'm, I'm also passionate about protecting it. I think there's a lot of big mega corporations that would love to own podcasting. And I think they'd ruin it. I think they would ruin what makes it so great. And so when you care like that, Right. And, you know, people come to me also and say, hey, I really wanna get advertisers for my podcast. And for me to care enough to say, you know what, I haven't seen that work for most podcasters. You know what actually does work is having patrons, having monthly supporters, having people who, you know, pay you $10 a month to get a shout out at the end of every episode. That works.

Right.

And so to be honest with people and to steer them in the right direction and to help them avoid the pitfalls of you know, hey, I'm gonna join this network and they say they're gonna give me X number of advertising dollars. And, and just to be open with people and say, well, uh, here's the truth, here's what I'm seeing, here's, you know, because I care. I care about the category, I care about your show, I want you to have success. And that's a competitive advantage for indies. Absolutely. Jason Cohen says this, uh, he's the founder of WP Engine, a massive company now. But he says that the truth is a lot of indie hackers give way better support than big multimillion, multibillion-dollar companies because the founder cares.

Yeah.

And if you're— and if you are not in a place to care that much, I mean, that's where, you know, in the early days of Transistor, I was grinding hard. It was like, I'm making money in other places in my life, but then I'm contributing all this energy and time to Transistor. And it was unhealthy in the sense that it wasn't sustainable for a long period of

time.

But those early wins, they're still that care, that enthusiasm, caring more than the competition. It's still paying dividends today. I had someone from a big magazine, like big, big magazine, who's— they're launching their first podcast program. And they wanted to talk to me at this conference I was at. And I was like, why are you approaching us? Like, we're, we're too small for you guys. And she said, well, when I was, I was working for this, this documentary company right when you started, and I reached out to you on Instant, on, on the chat, and you answered right away and really helped me out even though I wasn't a customer. I've never forgotten it, she said.

Yep.

And so this is the key. This is where we can be competitive as indie makers is we can just care more.

Absolutely. Yeah. And I think customer support, customer service should be on top of feature list. Like,

yes,

everything else is, of course, is an added bonus. You're trying to solve a problem. You're saving time. You're saving effort, money, all that shit is good.

Yeah.

But I think for every founder, for every product, customer service is like the number one feature that you offer, like 24/7 support and support tickets.

Yes, absolutely.

And I think that care is what people sense and they become loyalists and they become adopters to loyalists. Like, they stick with you forever, right?

Yeah.

And that's the advantage of being an indie hacker is you wipe up another product and you just like launch another landing page with another idea. The ones who use your previous product will actually come join your next product because they love you, not the product, you know, as a founder. Yeah. That's a massive, massive advantage. And just like, just to switch gears a little bit on Do you want to pick your brain on a couple of things? One is you write a lot and you podcast a lot. How do you come up with ideas? You know, what's your process look like?

Most ideas these days come from listening to podcasts. I'll be listening to something and it'll— something will kind of pique my interest. I'll write down notes in Apple Notes and then For me, I'm— I would actually like to dedicate more time to being a better writer because I think most of the stuff I end up publishing is okay. But at least the benefit is if I, if I get inspired by something, if I'm— if I kind of jump on that inspiration before it kind of runs out, Mm-hmm. That's generally the way I publish most of my stuff. And that's where most of my ideas come from is just hearing something on a podcast, seeing something in a tweet, reading something, reading a book about something, experiencing something in my own life, having a conversation with somebody. Right. And I like, you know, I like a lot of this advice of Writing, like writing a newsletter, an article, as if you're writing to one person. I think that can be effective.

Yeah. Yeah.

I think also just being fired up about something and being like, I'm gonna, I'm gonna chase this down and get it out of my system.

Yep.

Is helpful. And the nice thing now is like, I used to have to write and tweet and podcast. as a way of making my primary— a primary way of making a living, you know. I did that for a while where I was, you know, whether it was my membership site, Mega Maker, or advertising on my other podcast or selling a course or getting invited to speak at conferences.

Right.

It's been nice to not have to do speaking, writing, and podcasting with the ultimate aim of earning a living. I think it's been freeing because now I can write and talk about things that are actually not that popular. And but I'm able to chase down my curiosity on that stuff and explore things that I think are meaningful. Right. Yeah. So my tweets and articles about mental health are not as popular as my bootstrapping articles. My tweets and articles and podcasts about climate change are not as popular. My critiques of Elon Musk are not as popular. But these are meaningful topics for me that where I get inspired, something hits me and I go, I got to talk about this. This is important. And so, ideas come back from there too.

Yeah. You basically have to consume to create in a way. That's one thing I kind of make it as a habit is like consume great content so that you can create great content. For yourself and maybe like, you know, one other person.

Because everything is just a reaction to something else. We're human beings, like we're just bouncing off, you know, you're creating art or writing or whatever, you're bouncing off something. And so the, this is why I think podcasting is such a cool, especially shows like this where you're bouncing off each other.

It Right.

It, it, I, if I can react to your question, then it, it generates new thoughts. It generates, you know, it helps me put together existing things I've already experienced and researched.

Right.

This is kind of how it all happens. And so I think most good writing, good podcasting, good content is a reaction to something. It's like, whoa, I just found out this cool new way to write CSS. So you're reacting to something, right? You're reacting to this discovery. Whoa, I really disagree with the way that Elon Musk is, you know, carrying on in public. Okay, well, I should write about that. That's a reaction. Right. I think that the kind of bad writing is the stuff that isn't really— it is like the uninspired Non-reaction where you're just kind of writing for writing's sake, or you're just—

Or, you know, or you're basically like following a trend, you know, which is—

Or following a trend. Yeah.

Yeah. I think I prefer following curiosity more than a trend because at the end of the day, you really love what you put out as your work, what you produce, what you create. You'll be proud of yourself.

Yeah.

Or you have to— if you find a trend, you again are tagging to expectations like, do people like it? am I writing to live up to other people's expectations? Or am I satisfying them or pleasing them? Then it's not fun. It's work. It's kind of like you're putting in a position where you'll give up the thing you started. So I love what you said about consuming.

Yeah, yeah, I think you're right. I think you got to consume, you got to be reading interesting books. I think also you've got to be So consuming is part of it, but you also have to be doing interesting things. So that the, the, the most popular stuff I've written, I mean, some of the most popular stuff I've written is based on experiences I have had where— Oh, yes. Sometimes it's, sometimes it's visiting an interesting place or going to a conference, but there's some stuff that's just like, When John and I were bootstrapping Transistor, I stopped drinking for 2, 3 years, I think. And that article, I think it's just based on my experience of stopping drinking. And I think it's called Non-Alcoholic Drinks You Can Order at a Bar or something. It— Me sharing that experience and then, you know, giving a list of kind of the discoveries I made. That's the most searched blog post on my site, I think, is just people looking for, you know, non-alcoholic drinks. But that was, that was the product of me doing something interesting, which was I'm going to stop drinking for whatever it was, 2, 3 years.

Yeah.

So it's consuming, but then you're also, you got to be doing some things too. You got to be experimenting, trying things, and then sharing your experience.

Yeah, you're absolutely right. Love that. All right, I think, Justin, you and I, we know we can go on and on. We love podcasting. Seems like there is good chemistry between us. Yes. But I want to be mindful with your time as well as the listeners' time. So I have this segment called Rapid Fire 5, where I ask like 5 really interesting questions. But yeah, let's go. Just whatever comes to your mind, just shoot it out. Okay. Okay. Question, uh, which podcasts are you listening to these days? You're hooked to?

I listen to a lot of bootstrapping podcasts where it's 2 people just sharing their weekly update. I really like, uh, Bootstrapped Web with Brian Kassel and Jordan Gall.

Nice. Love that. And by the way, everything Justin mentioned from a resources standpoint, I'll put it in the show notes. Uh, question 2, One growth tip you want to suggest to SaaS founders who are just getting started?

Oh, yeah. Well, the number one growth tip is that 99% of your growth is going to be from choosing the right idea in the right market. So look for the right market first. That's gonna, that's gonna provide so much of the fuel of the energy is just picking a market where there's some sort of momentum. Doesn't have to be like a massive, massive industry, but it, there needs to be at least the possibility of hundreds of thousands of potential customers, right? So choose the right market. And that's the number one way to grow. Most of the momentum is in the market. Right. It's not in the marketing tactics that you're going to apply. You can apply the same tactics in different markets. and get wildly different results. And that is a result of momentum in the market. It's not what you do in terms of marketing tactics. It's choosing the right market first.

Right. Love that. If you want to give a shout out to a podcast host you're loving, who would that be?

I really like the gals at Software Social.

Nice.

They're Michelle and Colleen. It's just a wonderful show. It's in that same genre of 2 bootstrappers talking to each other, but they have a different tone that I really enjoy. It's really, it's a refreshing take on that format. I highly recommend it.

Love that. Love that. What are you reading currently? A book or it can be an article.

Yeah. The folks at Every suggested this book called The Metaphors That Make Us.

Oh, nice.

So I'm— I think that's what it's called, The Metaphors We Live By. Sorry, I'm reading that, which is interesting. It's kind of a book about linguistics, but I am enjoying it. And then on Audible, I'm listening to this history book. Let's see if I can remember what it's called. Where is it?

History book. That's interesting.

Yeah. Yeah. It's economic history, Slouching Towards Utopia: An Economic History of the 20th Century. Really enjoying it. I listened to the interview with the author, Brad DeLong, on the Every Podcast and bought the book. And it's fascinating. If you want to give yourself a context for how the history of kind of capitalism worked, why we are here today. Give yourself a sense of why things work the way they work. Slouching Towards Utopia is really good and the audiobook's pretty good.

Yeah. Adding to my wishlist. Last question. What's your favorite pastime as a dad?

Oh, as a dad? Oh man, it changes now. My kids are all

Let me ask you this. What's your favorite pastime with each kid? You have like 4 of them.

Yeah.

What do you do

with— I mean, all sorts of things. To be honest, one thing that's been true for all of them that is just wonderful is just taking a car ride with just one kid at a time. So, just honestly, just like picking them up from whatever activity they were doing. And then you have this opportunity to— they share the music they're listening with. Sometimes you're just driving along for 5 minutes and no one's saying anything. And then all of a sudden the 14-year-old will say, ask me a question about something. And those moments are so wonderful. They're just—

Mm-hmm.

They're simple. That, and often when you have a big family, there's just a lot of noise and a lot of competition for attention. But just a car ride, just picking up one kid and being able to give them all your attention.

Right.

Enjoying being in their presence. Right. Enjoying the music they're listening to and getting any sort of, you know, a lot of times, especially our boys, they're pretty quiet, but you, you know, If you give them time, just a couple minutes of silence, their brains are going and then they'll ask you about something. And it's just so fun to have these, these humans that are almost adults that are thinking through all this stuff and exploring all sorts of things and, you know, hearing their perspective. They have perspectives, they have their own opinions.

Yeah, of course. They have personas, they have their own characters.

Oh yeah.

Or,

and also them giving me a little, um, peek into their world. Like, how does their world operate? This world where you're DMing on Snapchat and then a lot of your social life is in Discord groups. And—

Right.

It's, it's just interesting to me. How does this work these days? Yeah. You know?

Yeah.

Yeah. Um, so I, I really like that. I'll add one more. which is I was thinking back in my life, some of the most meaningful moments are when my parents introduced me to other adults that could then mentor me or answer my questions. Or maybe I was really into computers. And so, my parents introduced me to this fellow that worked at the university who gave me access to the internet before the web even existed back in '91. And I've tried to do that with my own kids too, is to introduce them to really cool adults that are doing cool things. You know, I'll go for brunch with my friend who's a data scientist and I'll invite my 14-year-old along just so he can be there in the same place. I love that. I run a meetup called Geek Beers. And we do it at a pub. You're allowed to be underage and be at a pub here in BC. And so, my 17-year-old has come and just sat with all these other nerds and geeks in the tech industry. And I've been able to engage with them and explore questions about mathematics and programming and all sorts of stuff. So, I think those two things bring me so much joy. I love that.

Yeah, for some reason, even, I don't know, I have a 15-month-old toddler. He loves car rides. He just loves— he sings.

Yes.

You know, when I pick him up from daycare, he sings, like, or he learns something at daycare and he replicates with me. Most of the time I don't understand what he's babbling, but I just go with it.

Yeah.

And he loves it because we're giving him the one-on-one, like, undivided attention. So yeah, I can kind of relate. Yeah, I can relate to what you're saying about the pastime.

Yeah, it's wonderful. Enjoy all those moments. They're so special, especially once they grow up, you realize how special they are.

Yeah. Awesome. This has been a blast, Justin. You know what? I enjoyed each one minute of your ideas, your principles, your beliefs as a founder, as a dad, and as a human being in general, right? And thanks for being so authentic, so transparent, and being you yourself, which I love about people like you who are just like themselves. No pressure, nothing. Talk from the heart. So, love this conversation, Justin, and thanks for being on the show.

Appreciate it. It was a pleasure to be here. Great. Let's do it again sometime.

Absolutely. Yeah, we should bring you back again, you know, sometime next year.

Sounds good.

All right. Cheers, guys. Thanks for listening.