I first heard of Justin Jackson about six years ago. Back then, he was consulting full-time for a company with the dream of going independent. Fast forward to 2018, and after building a successful business, he’s now embarking on a new adventure. Justin talks about his parents, dealing with depression, and a new business he’s co-founded.
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For me, Justin Jackson is a special person. We met back in 2012, I wanna say, when he invited me on a now-defunct podcast to coincidentally talk about an also now-defunct podcast that I used to host. Justin has been a great friend to me, and in many ways has lived the dream of making a living by building a business that helps people create things and launch them into the world.
As with many of us, I don’t think Justin understood just how much his early life would influence who he is today.
My mom was a teacher most of my life and my dad was the headmaster of an all-boys boarding school. [laughs] And so my mom is just wildly creative, very funny, very much like me; I’m very much her son. When we get together at family reunions, it is her and I just laughing and making up jokes about things that no one else thinks is funny.
I have this one memory… There’s this radio show that I loved, and the main character of the radio show had this building that they turned into a center for kids, and it had a train set in it, and a computer room… And every room of this house in this center was for kids, and I thought “I wanna build something like that.” I said “Mom, I wanna do this! I wanna build this thing! I think it’s gonna cost about a million dollars”, and she said “Well, we’re gonna have to go buy a lottery ticket then.” [laughter] And she took me out and bought me – we went and bought this lottery ticket… And you know, some folks have asked me if she was trying to teach me that gambling doesn’t work, because – spoiler alert! We didn’t win… But I actually think she was really excited about the idea, and she was like “How are we gonna get a million dollars? Well, we’re gonna have to buy a lottery ticket!” So she’s always been a big believer and supporter in what I do… And dad the same way, but dad is in a very different way. He’s very pragmatic. He’s the person that I would practice my pitch on.
In college I had a job as a bellboy in a hotel, and about maybe six months into that job or a year into that job I said “I’ve gotta quit this and start my own business”, so I knew that to do it I would have to convince dad.
The first thing he would always say was “Are you sure this is a good idea?” My mom was just like, “Oh, Justin, yeah, you can do anything!”, but my dad was always like “Have you thought this through? Are you sure this is a good idea?” and he was not nearly as susceptible to my charm as maybe mom or other people were. He had some good questions. So even just mom and dad - that influenced me quite a bit.
Justin also gives credit to an English teacher he had in high school. Her name was Dr. Nyberg. Dr. Nyberg had a Ph.D. in English Literature, and apparently assigned an essay every week. Now, I’ll give you a second to go back in time and remember how much your 15-year-old self would have complained about that…
She was not a very kind marker. We would write these things, and then she would just tear them apart. I was confused by it. It just seemed repetitive and boring… And she was a really charismatic teacher, but she kept giving us these really dull assignments, and I didn’t understand it until I got to college and it came to our first writing assignment, and it was a piece of cake for me. Everybody else in the class struggled. I nailed almost every single writing assignment because I’d been taught how to write well.
I find it fascinating when I look at my own life and realize that a lot of the things that I didn’t like in the moment were just amazing life lessons for later.
Yeah, I’ve actually been thinking about this a lot, because a lot of my life I have tried to avoid discomfort. I would try to go the easy route. If I needed to accomplish something, I would see “What are the hacks I can use to get around this?” or “How can I use my charisma and my charm to maybe do this faster, or cheat a little bit?” This is not just even in assignments or work, but also in personal things. When I had personal problems, I would sweep them under the carpet and just try to forget about them… And I got really depressed last year. I had a real struggle with just some personal issues in my life, and the reason it was so hard is because basically everything kind of culminated at once. All these things I’d been avoiding, all these things I’d swept under the rug - they all kind of came out at once, and I had to deal with them all at once.
And what it taught me is that you can’t run from discomfort. It’s better to face those hard realities now than later. It’s better to do the hard work now than have to deal with the repercussions later.
I think it’s interesting that you bring up these difficulties that you went through last year, and the depression that you went through last year… If I recall correctly, you wrote a blog post about it, and one of the things that stuck out to me was the fact that you said that it was a learning experience in balance, as well.
Yeah, there’s a few things there. One is balancing chaos and order in my life. I just thrive on chaos. I love it. I’m gonna make 100 projects, I get an idea at one in the morning, I’m going to work all night and do it; I have a dream and I just wanna start working on it right now… I just love the creativity and the energy that comes from chaos.
But there needs to be balance in our lives. You can’t just have chaos. If all you have is chaos, then you just have a chaotic life. I think I’ve learned that I can’t just keep pushing myself forever. You can sprint for a while, but you can’t do that forever. I think also there’s this balance of caring for others and caring for yourself, and I had thoughts about going to a therapist a lot in the previous years, like “Huh, I wonder if I should do that…? Nah… Why do I need that? I don’t need that” or “Nah, it’s too expensive” or “It takes too much time”, “It’d be too awkward to go and find somebody…”
I treated emotions suspiciously, and it took me hitting rock bottom… I mean, first I tried one of those chat therapy apps. I think even that was me kind of running from discomfort, like “Ugh, I don’t want the discomfort of going and finding a real-life human therapist. I’m just gonna use this. It’s easier.” I did that for a bit, and it was somewhat helpful, but things got worse. And when things got worse, that’s what pushed me onto the web, and like, okay, “therapists near me”, and looking at 4-5 websites. And then I eventually settled on one that I felt was a good fit for me, and that was a game-changer.
Finally, I was taking care of myself. I never went to the doctor. Something would be bugging me, and my wife would be like “Go to the doctor, for goodness sakes!” and I’d be like “I don’t have the time.” It was better for me to just keep my head down and keep helping these other folks, keep helping the family… But you can’t help other people if you’re not doing great.
I think balancing those things too, between saying “Okay, well I’m helping other people…” – you’ve gotta care for yourself, too. You’ve gotta take care of your emotional well-being, your mental health, your physical health… All those things. You’ve gotta be grounded, you can’t just be chaotic. There’s a lot of balance in there.
One of my favorite questions to ask business owners is what the scariest thing was about going out on their own. Justin’s response, I think, is one of the most relatable I’ve heard.
The scariest thing for me has always been – you know, I’ve got this family to support, and there’s four kids… My wife works now, but she didn’t work back then… And saying “Man, I hope I can do this.” I’m going from something consistent, I know I’m gonna have this every month, to not consistent. That was one thing.
There’s other things, too… To be honest, my ego was a huge thing. By this time, I had a little bit of a following online, and I really wanted to maintain this appearance that I was in control, that I knew what I was doing, that I was confident, that I was someone worth following. And the fear of losing that was one of the things that kept me from acknowledging that I had problems, because I just wanted to appear – you know, “I’ve got it all under control. I know what I’m doing.” Who wants to follow someone who’s insecure? Who wants to follow someone who maybe doesn’t have it all together?
I’ve realized that ego really is the enemy. Every mistake I’ve made since I went independent and worked for myself has been ego-driven, as opposed to just “Okay, Justin, let’s get grounded here. Let’s look at reality. Let’s be honest with ourselves… And quit focusing on yourself so much, Justin. Focus on who you’re trying to help, and how are you actually helping them.”
The question my wife would always ask me (and it’s a good question), “Do you really wanna help people, or do you just wanna be famous?”
Yeah. Because a big part of me just wants to be famous. Now, I don’t actually think there’s anything wrong with that, because I think it’s better for me to be honest with myself and actually articulate what I want, as opposed to articulating one thing, which is “Oh no, I just wanna help people and just be a great entrepreneur…”
Right, articulating the lie you’re telling yourself. [laughs]
Exactly. I can articulate the lie I’m telling myself… But when you actually articulate what you truly want, what is your actual desire(s)… I could say, okay, do I wanna be famous? And the truth is, well, I want some of that, but I don’t want to be too famous. I’ve seen what that can do to people. But do I like to be publicly recognized? Do I like folks following my work? Do I like to have an audience? Yes. Would I like to have a bigger audience? Yeah.
And even me articulating these things right now is difficult, because I’m thinking “Oh man, all these people are gonna think I’m a scummy fame-seeker…” But it’s better for me to just be honest with myself and say “Okay, is this what I want?” I think rationally my fear was “How am I gonna provide for my family?” but then emotionally, my fear was “Am I going to be able to keep looking like I’ve got it all together and I’m a famous person?” [laughs]
Now I’m just more honest with myself. Yes, I wanna build an audience, but I wanna do it sustainably; I’m okay with recognizing that I do like being the center of attention, but I’m also gonna be careful about it, because there’s some potential pitfalls there, too.
I love that response, because I think that that is the realization I came to in 2014… Which was that I finally came to the realization that I was doing nothing but trying to be famous, and that that didn’t actually make me happy. And I think ever since I’ve acknowledged the fact that I don’t want to be famous, I just want that whatever I create for some people to care about it. That’s it. That’s all I’d want.
After I’ve acknowledged that and said it out loud to myself, I felt so much happier… You know?
Yes, yes. That’s the power of articulating what you want, and being actually honest about it. Because once it comes out of your mouth, once all of these things that have been floating around your subconscious actually come out as words, you can see it for what it is. So when my wife said “Do you really wanna help people or do you just wanna be famous?”, I had to wrestle with that… And it’s okay, by the way, to just sometimes articulate things and see if they fit. So because I’d never actually spoken the words “I want to be famous” – whoa, they’re out of my mouth, and now I have to wrestle with it, right? I have to be like, “Okay, does this fit who I wanna be? Does this fit who I am?”
Well, you see, I feel like – you know what, lie to the world, but don’t lie to yourself… You know what I mean? [laughs] If that makes any sense… You can tell anybody else whatever you want, but at least be honest with who you are and what you want to yourself, even if what comes out isn’t all that great.
Yeah, exactly. But the beauty of it is when it does come out, then you can compare that thing that just came out of your mouth to your values. It’s good to not be afraid to just try some things on.
It’s kind of a drastic change in topic, but we’re in 2018… Why build a SaaS like Transistor right now?
You know, there’s the public relations version of this, Tim, and then there’s the real version.
Give me the real version.
So the real version is I had a really hard 2017; I was making most of my living off online courses, and I think 2017 was kind of a watermark year for online courses, because it had been up to that point a really good way to make a living, and then certain segments of that market dropped out completely. Business completely like I was doing - those really got hit hard… And I think it was because people had been buying these courses, and then in 2017 they kind of woke up and said “Well, wait a second… I’ve got like 20 courses in my Dropbox folder called Books and Courses, and I haven’t done any of them. They’re not actually making my life better.”
So I was thinking, man, it’s getting harder to do this… I think it’s still worth doing and I think it’s still worth doing well, I think there’s still opportunities, but it definitely got more challenging.
Another challenge for me was Intercom, which is a big startup… It started releasing these incredible guides, that were right in my wheelhouse, and for free… So I had this competition that was now offering these for free. Udemy was lowering their prices, and it was just getting really hard.
In 2017 there was a first draft NBA player named Justin Jackson. I didn’t think it would affect me, I laughed about it at first…
Oh, boy… [laughs]
…and then all of a sudden I’m getting way less traffic and way less inbound leads than I used to. Sure enough, I google my name, and before, Justin Jackson - I was number one, and now I’m on like page five… Kids reach out to me on Snapchat thinking that I am the basketball player, who’s like black and seven feet tall… Which I think is hilarious.
So all of these things kind of culminated, and I had this hard year emotionally… And so my friend John - he was one of those people that I just reached out to when things were tough, and we kind of commiserated together… He had said, “You know, I built this little projects for Cards Against Humanity…” And again, in the PR version of this, John asks me to be his co-founder, but in reality, I begged him to let me be his co-founder…
So part of it was I needed something new… I was emotionally spent, and I just needed something new. I needed a new project, a new focus to pour my energy into. I think there was a lot of good evidence that now was a good time to invest in podcasting. Previously, I’d always said “I think podcasting is a bad market, because it’s a lot of DIY folks, a lot of hobbyists, and they don’t like spending money”, but what had changed is that there were a lot of companies investing in branded content… So there’s just a lot more activity, and a lot more activity on the professional end of the spectrum.
I felt like, okay, if I am gonna invest myself in something – I’d thought about acquiring an app, I tried to acquire two or three apps, and they were never quite the right fit… And then Transistor came along, and I said “John, I could help you so much. Let’s partner up, let’s do this together.”
We have a show together called “Build your SaaS”, and it shows how different John and I are. It really kind of exposes a lot of my weaknesses, which is I’m really quick-start, like “I wanna do things now. Let’s go, let’s go, let’s go!” I feel like we really balance each other out really nice. I speak a million miles a minute compared to him. You can’t listen to our show at 1.5 speed, because he will be normal speed and I will be unintelligible… Which is fine. He’s actually got the best things to say anyway. That’s why we’re doing SaaS.
I remember when I started doing online courses – I went independent the year that Nathan Barry decided to double down on ConvertKit. Books and courses were making 200k-300k/year… Why mess with that? That’s incredible. And he said, “Well, I know a lot of people that have been doing this for a while, and to really scale this business you have to invest in a lot of people, you have to invest in a lot of ads… It’s like squeezing water from a stone. It just gets harder and harder”, and I thought “You’re nuts!”
My first year I did pretty good. I made more money than I’d ever made. Then even last year, in the first half of last year, when things weren’t as bad, I made more money than I ever made. But then getting depressed and having weeks where I was like “I can’t get out of bed. I can’t go to the office.” I’d go to the office and I’d browse Reddit for an hour and then I’d go home. When you’re doing that business, you really need to show up every day, you need to be “Hey, it’s me, Justin! I’m Mr. Happy!” and you can’t do that when you’re depressed.
One thing about software as a service is it takes a lot longer to build it up, but if the business model matches what customers expect and want, it can really be revenue you can count on every month. It just felt like all of those things culminated into why it made sense right now.
We’re also okay with the fact that it might not work out, but I think John and I were both feeling like “We need this. We need to work on this.” So it’s for emotional reasons, too. We just need something to invest in, that we’re proud of.
How are you feeling now?
Like in general?
Yeah, in general.
I mean, I’m doing so much better than last year… Not working, not getting much done in the last six months of 2017 - it wiped me out emotionally, it wiped me out financially… So there’s real-life repercussions to all that, but even when things get stressful, like pragmatically, like “Oh man, it’d be nice to have more money in the bank account right now…”, I have a calm now that I didn’t have before… And I don’t wanna make it sound like I’m completely zen, because I freak out all the time; I have times where I just lose it… But I’m a lot more grounded, I’m a lot more honest about how I’m feeling.
I see my therapist about probably once a month, and if I’m struggling with something, I can feel it kind of welling up inside me… When things are rattling around in your brain, you can drive yourself nuts. So writing helps me, but the thing that helps the most is having a professional, who sees tons of folks like me, and has seen it all before, and can go “Listen to me and validate how I’m feeling, and give me good tools and tell me when I’m wrong…” [laughs]
She’ll never say what I’m feeling is wrong, but she’ll say, “Um, but that thing you were planning on doing because of those feelings is wrong. You can’t do that. That would be destructive.” That alone, just having a therapist that I can call and book an appointment with has been so big.
I’m really enjoying having a co-founder. I was trying to be this solo founder that could do it all himself… And every successful solo founder I know has tons of help. They have contractors they hire, they have systems, they have all sorts of things in their life that make it work, and I was just doing everything myself.
Getting to work with John - just having someone else that’s there is so helpful… Or even someone – we get on the phone and it’s like, “Whoa, man, this is hard, isn’t it?” He’s like, “Yeah, this is hard.” Just having someone to talk to has been so great.
Our transcripts are open source on GitHub. Improvements are welcome. 💚