Entrepreneurship, mental health and Transistor, with Transistor.fm co-founder Justin Jackson

Justin Jackson dreamt of launching a product in a market big and hungry enough that, if he could swim out and catch that wave, it would be bigger than any wave he’d caught before … then his friend told him about the podcast hosting software he was working on. In 2017, the two partnered to become co-founders and co-CEOs of Transistor.fm, the same host used to upload this episode! On this episode, Jason and Cee Cee talk industry with Justin and hear the stories that started it all.

Jason Gillikin: Welcome to the Earfluence podcast, which is a podcast about podcasting from a podcast production company.

I’m Jason Gillikin, CEO of Earfluence, your host for today. And with me as always is Cee Cee Huffman, pretty much the doer of all things at Earfluence. She does social media, she does content creation, she does editing, and she is the cohost of this podcast. What’s good, Cee Cee?

Cee Cee Huffman: Hello! I’m great. I’m actually at the beach. So I found the quietest place I could at the beach, to record this podcast. And I’ve been working all week, but it’s been really nice to just look at the water while I do it.

Jason Gillikin: Nice. So what’s been the highlight of the week while you’re at the beach?

Cee Cee Huffman: Well, I won two games of pool last night, and I’m really bad at pool, and I’ve never won before.

And so, I’d say that was definitely the highlight.

Jason Gillikin: Wow. Very cool. All right. Well, we are joined by Justin Jackson, who is the CEO of Transistor, the CEO and co-founder of Transistor.

Cee Cee Huffman: Yeah, something we use all the time.

Jason Gillikin: All the time. And talking offline with him, I don’t know if he’s a pool player, but he is a skier, based in British Columbia and lives very close to mountains where you can ski, where he can snowboard.

Justin Jackson, welcome to the show.

Justin Jackson: Hey, it’s great to be here. I’m excited to dig into these two pool games at Cee Cee win. I think that should be the focus of the show. Let’s dig into all the strategy, how it happened.

Jason Gillikin: How did it happen?

Cee Cee Huffman: Hit it and hope for the best, hit it and hope for the best. That’s pretty much it. I’m really good at it on iMessage games, because it tells you the direction that it’s going to go once you hit it.

And so, I was trying to pretend that I was playing iMessage, and that worked for me.

Justin Jackson: I like this. So the key is you got to practice on iMessage, and then you take that game to the real game.

Cee Cee Huffman: Yes. Yes.

Jason Gillikin: Nice strategy. That is smart, Cee Cee. Nice work.

Cee Cee Huffman: Thank you. Thank you.

Justin Jackson: Perfect.

Jason Gillikin: Well, Justin, I’m excited to dig in to learn more about Transistor because we, we use it as a company at Earfluence, we use it. We have about 10 podcasts right now that are on Transistor. We’ve used other podcasts hosts before, and just so everybody knows Transistor is a podcast host platform, we’ve used others. You might’ve heard of Libsyn, you might’ve heard of Anchor. You, might’ve heard of, you know, some of these other ones, and we’ve used Libsyn in the past and, that’s, that’s fine.

I like some of the things that Transistor offers better though, so. You know, Justin, I’m excited to hear your story and why you started it and, you know, what it’s been like to challenge some of these bigger names in a, in the podcast hosting space.

Justin Jackson: Sure. Yeah. I’m happy to get into all of that. One correction, though, technically I’m, I’m not the CEO, technically John and I are both co-CEOs and co-founders.

So we, we are basically equal partners in everything, so we’ve been hesitant to even take on any of the normal – I guess for tax purposes, maybe one day we’re going to have to do it, but right now we just introduce ourselves as co – founders, and that’s worked out well for us.

It’s essentially still the two of us. We have a few contractors that help us with customer support, and we have someone that helps us with podcast editing. But,  other than that, it’s just, it’s still just John and I. And, yeah, it’s been a great journey. I’m happy to get into it.

Jason Gillikin: Well, that that’s super interesting right away because you said co-CEO, so my mind is wondering, ‘OK, well, how do you even do that?’

Like, how do you, like when, when it comes to making a decision? Yes, you want to talk to that person about it, but ultimately somebody is going to have to be the decision maker. Hold that for a second and rewind to, you know, why did you, or why did you and John decide to start Transistor?

Justin Jackson: I mean, there’s kind of, there is a long string of events on both sides that I think culminate in us starting the company.

So, we met in 2014 at this festival called XOXO in Portland. And he, at the time, had built the first version of Simple Cast, and I had a few podcasts that I was running at the time. And he said, “Hey man, you should just, you should just come and, you know, try out Simple Cast.” So I did, and we would then just see each other every year at XOXO. Hangout, talk about podcasting, talk about life. And, over time, we even started doing a few projects together and worked on a few things that, you know, never, never really launched or, you know, never really got any traction.

Jason Gillikin: So what were you doing in 2014 then? When, when you two met at XOXO, what was, what was your job?

Justin Jackson: At the time, I was a product manager for Sprintly.

Jason Gillikin: OK.

Justin Jackson: Project management software. So yeah, I was like working full time as a product manager and doing podcasts on the side.

Jason Gillikin: That’s, that’s really early, 2014. You were, you were early in the game then.

Justin Jackson: I mean, at the time, I felt like I was late.

It’s so funny to think about it now, but I mean. I, even back then, I remember feeling like – I had this show called “Product People,” and I was, you know, I just felt like I was late. Like the, the best kind of interview shows at the time that we’re interviewing other product people, were, you know, had been going for, some of them had been going for five years by that point.

But, the nice thing about podcasting is it’s, it’s a wave that has kind of culminated slowly. I think podcasting has been growing about 10% a year, forever. And, we just flipped over, you know, like 51% of Americans have listened to a podcast at some point. But it’s not like video that was like, you know, it just accelerated a lot faster, right?

So, yeah. Yeah, I was doing it back then. And then, fast forward to end of 2017, John’s working for Cards Against Humanity, and they wanted to launch a new show, and they were looking at all the tools, and John’s like looking at them and he’s like, “I, I could build something better than this,” and so he just asked if he could, you know, if you built a tool, would they use it? And they said, “Yes.” And he was, I think, just thinking, ‘Well, I’ll just do this for cards and, you know, we’ll see what happens.’ But I was like, noticing all of these touch points over the years. Like in the past, I would say, “Ah, it’s not a great time to start a podcast company” It was very DIY, really price conscious customer, mostly still hobbyists in their basements.

Jason Gillikin: Definitely.

Justin Jackson: But then, I just noticed, for example, companies starting to build podcast studios at the company, hiring podcast talent, multiple companies starting a podcast. Plus, you know, in the, you know, it used to be just, you know, me and a few of my friends that had a podcast, but increasingly more and more of the people I knew on the internet had started one or wanted to start one. And then we also had the Zeit Geist of Serial and Gimlet-

Jason Gillikin: Right.

Justin Jackson: The New York Times is doing a piece on podcasting every week, it seemed like. And so, it’s very much kind of, in the public sphere. People are thinking about it, companies are actually putting real dollars behind it, and it just felt like the right time. I was also just ready for a new project. And so, you know, in the – I’d like to say, like, John was like, “Hey Justin, we should work on this together,” but I begged him.

And I just, I just knew – this hasn’t always been the case with other partnerships and other projects, even projects that John and I had worked on in the past together – but I just knew this one like, I just knew if – I was like, like an animal just ready to get out of the cage.

Like I was ready. I was, I was – as fast as John would let me run, I was going to run. And so, I was just geared up. We were both, kind of, uniquely poised for the opportunity, and it just felt like things were all really aligning. And so, I was ready. Like, as soon as he told me that he was working on it, I was like, “We’ve got to do this together.” He took a little bit more convincing.

Jason Gillikin: And so, were you working on it like, on the side for a little while? While, while John is at Cards and, and you’re, you’re a project manager?

Justin Jackson: At this point, I went – I’d gone independent in 2016. So I had this community for bootstrappers called MegaMaker that was earning, you know, enough revenue for me to live on, and I was speaking at conferences and doing other things. So, I was, I had already cut the cord, and had been running my own business for a while. He was still working full time and – I mean, the nice thing is we, we started a podcast called Build Your SaaS almost as soon as we signed the partnership agreements.

So, I could spin a good tail right here, but the reality is all in that podcast, it’s like a journal of what we’ve done so far. And, yeah, so at the beginning it was part time, and we had a working version almost right away, ’cause John had been working on it for Cards. And we were able to, I think even as soon as February or March of that year, 2018, we were able to start getting early access users in, paying us and, you know, it didn’t, it didn’t grow as – you always want it to grow faster, but in retrospect, it grew really fast. Like we officially launched August 1st, 2018 and by August 2019, one year later, we were both full time on it. But, at the time, during the grind, it was like, “God, this is taking – if you listen to some of those episodes, we both start flailing in different ways.

For me, I was starting to focus all my time on Transistor. Like, I would just wake up every day, answer customer support requests. I was marketing it. I was building the marketing site. I was just spending so much time on it and not really making any money. And John was – his money problems were fine, ’cause he was working full time, but time-wise he was in a real crunch because he’d come home exhausted from looking at a screen all day, and then you would have to look at a screen evenings and weekends.

So there’s definitely – you’ll, you’ll notice there’s like a pulling apart when we’re, as we’re, building this. It’s like we’re getting stretched to like an elastic band. And there is, you know, elastic bands only stretch so far. I think we were fortunate in that eventually ,  we just – we had it had traction, but the traction just started – it was just, you know, there were months where we were growing 30%, 40% every month. And so, that helped to get us to this baseline where we could both, you know, focus on it full time.

Jason Gillikin: Wow. Yeah, that’s really great, Justin. So, you know, when, when you’re first starting out, did you know, like, “OK, we can take share. We can take market share away from Libsyn. We can take market share away from SoundCloud. From, I don’t know – I don’t know if Anchor was super active then, but was that the goal?

Justin Jackson: Yeah. I mean – so, there’s a few things I had met this guy named Adam Wathan. And, he had introduced me to the other guy named Taylor. And these two guys, kind of blew apart my understanding of what was possible in business and what, what made some businesses, kind of, just catch fire. So Taylor Otwell, do you know who that is by the way?

Jason Gillikin: No, I recognize the name, but no.

Justin Jackson: Most people don’t. He’s – I think he’s one of the most successful, independent bootstrapped entrepreneurs on the planet, but he doesn’t even consider himself an entrepreneur really, or a good marketer, or anything.

He’s a programmer. He started a framework for PHP, which is a programming language, and he did – he started this, I don’t know, 10 years ago ? Something like that. Since he launched Laravel, I think he’s made about $10 million from Laravel related products. And really for most of that, he’s been a solo person. He has – now he has a few staff people as well.  And I just remember, like, in my sphere, you know, I was friends with folks like Nathan Barry, and I’d seen like, you know, what they were able to do. For example, I had a course called marketing for developers, and I thought I had done pretty well. It was doing about $200,000 a year or something.

And, you know, in my sphere that was pretty normal. And, Adam came along and he’s like, “Oh, hey. I, you know, I’m writing a book for Laravel – this thing that Taylor designed – and I’m wondering if you could give me some tips on marketing and on launching it. And I said, “OK, sure.” And so I’m giving them the tips, I’m giving them the same launch plan that I did for my book. And then in one week, he made more than I had in all a year.

Cee Cee Huffman: Wow.

Justin Jackson: And I said, what, what is, what is going on here? And he’s like, “Is this pretty good?” I’m like, “Yeah. I’ve, I’ve never, I’ve never seen this before.’ So his floor was my ceiling, you know what I mean?

And that’s just a weird place to be in to, to feel like, no, like a good, independent business for a solo founder is, you know, $200,000 a year. Like that’s, that’s, you’re doing good then, and he showed me that there was a whole other ceiling. And I think the key piece I realized is that it’s all about the market.

It’s all about the market you choose. So, PHP has millions of developers that use it all around the world. It’s not the coolest language, it’s kind of old and crusty, but these developers have to use it for work, and they’re desperate for good tools. And so, when Taylor came along and introduced Laravel, they were hungry for it, and these millions of developers that had never been given anything cool suddenly had some cool stuff to work with. And then Adam came along, saw the traction Taylor was getting in that market and he wrote a, a book on, basically refactoring for Laravel and, in the same way, that took off as well.

So, as I was observing this, the note I was taking mentally was: the next product I launch is going to be in a market that’s big enough and hungry enough that, you know, if I can swim out and catch that wave, it’ll be bigger than waves I’ve caught before. As I’m having that realization, John comes to me, he says he’s working on this thing. Everything starts to click into place.

I knew it wasn’t a massive market – it’s not as big as PHP developers worldwide – it’s still fairly small, actually. I mean, we’re, I think we’re at maybe over a million podcasts on Apple Podcasts, still small. There’s like, I dunno, 50 million YouTube channels or something like that, 550 million blogs. But, it was big enough and the market was hungry enough, I think, for something new, there was some kind of old crusty players, like – well, I won’t name names, but. There’s some old crusty players. And so, I realized there was potential there, but the key was this market has to have enough of the, the shape and characteristics of this market matter a lot.

And just like a surfer sits in the water and waits for the right wave, I was sitting in the water, waiting for the right wave, and I didn’t want to swim out for anything that wasn’t worth surfing. And so I’m sitting in the water and this podcasting wave comes along and I’m like, “OK, this one, it looks good. The size and shape of this wave looks like it has potential.”

Jason Gillikin: Wow.

Cee Cee Huffman: That’s awesome. I love the metaphor, too. And you said you had a book, is that right?

Justin Jackson: Yeah. Yeah, “Marketing for Developers” was the book that, that I launched. And yeah, it was fine. It was fine, but it was just, I mean, in retrospect it makes sense. If you take the worldwide, like worldwide, there’s tons of software developers.

It’s actually a good market. They’re very – it’s a unique market because these folks are economically incentivized to improve their skills and to get better tools. And so, they buy lots of courses, they buy lots of books, they buy lots of tools to make their lives better. But, if you take a whole pie of software developers worldwide, and then you go, “How many of them want to learn marketing?” It becomes very small. And then it’s like, how many of them want to learn marketing from a jackass like me, it’s even tinier.

I think the other thing I realized during that time is, you know, I had always started these businesses that were just enough. It was like, “OK, if I can get like,” again, I have four kids. So like, you know, to some people, $200,000 is a lot of money, but once you, you know, pay off your business expenses, and once you pay your payroll taxes, and once you do all that other stuff, even as a solo founder, it’s just not that much, especially in the Pacific Northwest. So, I was always like, building these businesses that were just enough that there wasn’t like a bunch of margin there.

And the other problem is, I was building these businesses that didn’t build on top of each other. Like, I would launch something, and it would have a good launch, but then I would have to start all over again the next quarter, and it was just exhausting. But then I saw Adam launch his book and it was like – I think he’s been public about this – I think it’s made about $2 million or something.

Jason Gillikin: Wow.

Justin Jackson: And just him having all of that margin in the bank account, he didn’t have any desperation, right? It was like, he wasn’t just building for the next quarter. He built something, launched it for a big enough market that was hungry for what he wanted. Eh, did I say that right? A big enough market that was hungry for what he was creating, and then he was able to – he had leverage, right? And so, yeah, I think that was part of it was me thinking it’s just like, like –

Like, you’re at the beach right now, Cee Cee. Some waves that – a good wave just lasts a lot longer and you can see someone, if they try to ride a small wave, they’re just like, you can maneuver your board however you want, you can be the best – the example I always give is like, you can be the best product person, marketer, CEO, whatever.

But if you’re writing a little dinky wave, it doesn’t matter how much skill you have. It doesn’t it doesn’t, you’re not the, wave’s not going to get any bigger, the key – yes, your skills matter. Yes, your connections matter. Yes, you know, everything you bring to bear matters, but no wave, no business. Right?

Like that’s just how works. But for the right wave, like again with podcasting, I saw that wave and I’m like, I can go head to head with those guys. Like, I can compete with Libsyn. I just knew it. And John’s an incredible product person, credible builder.

He’d already built Simple Cast before, I was like, “We can do this,” right?

Jason Gillikin: That’s, that’s awesome, Justin. That, that wave that you’re on and continues to build right now. And like you said, with over a million podcasts out there on Apple podcasts and, you mentioned some old and crusty players in the industry, my first podcast, 2017 and I used SoundCloud, so yeah. That’ll tell you something –

Cee Cee Huffman: My first podcast was in March and I used SoundCloud!

Jason Gillikin: That’s

Cee Cee Huffman: a, that’s a no, Cee Cee.

Justin Jackson: I mean, it’s, it’s good. What’s nice about it is tha – I recommend SoundCloud and Anchor to people all the time because, for some folks, it’s a great place to start and, we’re not a good fit for somebody who’s just figuring things out. But, we have a lot of people who import shows from SoundCloud and Anchor . And so, there’s a natural, kind of, stair-step process that people go through. And once they, you know, once they get there bearings and there’s this kind of natural, like, “OK, now I’m gonna upgrade my microphone and now I’m gonna, you know, upgrade my podcast hosting and analytics” and you just kinda keep going and going.

So, yeah, I liked that part of it. There’s still some substantial threats, I think, in the industry, but overall it’s been really good to us so far.

Jason Gillikin: Well, yeah, I mean, of course there’s, there’s some  threats. You look at – like, Spotify owns Anchor now, right? So –

Justin Jackson: Yeah, Spotify is the biggest threat.

Jason Gillikin: And so like you, you started to see some success from, from search and you had mentioned before that there were some months where you would grow a little bit and then some months that you would grow 30, 40%.

Was there a “Mama, I made it” moment for you?

Justin Jackson: Oh yeah. I mean, when I went full time, that was, that was amazing. I think we were paying ourselves each like five grand a month or something, and it wasn’t a lot of money, but just the feeling of like, “OK, we made X amount last month and for sure we’re going to make that amount plus something else this month,” was just really incredible, so. And, and generally like the, the, the benchmark we were going after was, you know, first we were going after $10,000 a month. And then the real kind of – what Jason Cohen told us, he’s the founder of WP Engine – he said, “You know, after a couple of years, you should be – two to three years – you should have $10,000 MRR per founder.” That’s kind of like the, the benchmark for most bootstrap SaaS. And, yeah, when we hit that, when we hit $20,000 total a month, it was like, “OK, like, this is kind of like a default alive, you know, it’s like, all right, we, we, we hit this”.

It’s still not, hasn’t proven itself to be a good business. We always said, we felt like a good business would be $50,000 a month. But, when we hit that $20,000, it was like, “All right, this feels, this feels good.”

Jason Gillikin: When did that happen?

Justin Jackson: I think that’s still public. We had our, all of our figures monthly, public for awhile. We hit $20,000 a month right before John went, John and I went full time. So July, 2019.

Jason Gillikin: Wow.

Justin Jackson: Yeah. And that was, I mean, at the beginning, it’s super fun ’cause it was just growing so much every month. It’s just, you know, I would kill for these growth numbers now. Yeah, that was really fun.

And then our next kind of, we don’t have any like hockey stick inflection points, but we got big boost,from the pandemic actually, when people were locked down. Not the whole pandemic, but April and May we had a significant increase in customers. And I know the guys Squadcast.fm, they do a like remote podcast recording software, they, they said, and I think this is public as well ’cause they did it at a conference, that last year, at this time, they were at $10,000 a month in recurring revenue. And now, they’re at a hundred thousand dollars a month in recurring revenue, and most of that growth happened during the pandemic. Wow. So, we didn’t see growth like that. Like, that is that’s incredible. That’s incredible. But, there were certainly some players in the industry who benefited massively from the quarantine, which is a weird place to be because there’s so many people are suffering. But, people locked down in their houses, you know, a lot of their first thoughts were like, “Oh, this is great time to start a show. I’ve always wanted to do that. And so, yeah, you can’t really plan on it, but, that’s, that’s definitely happened for us as an industry.

Cee Cee Huffman: I remember when the pandemic started, everybody said, “Oh, podcasting is going to die.”

You know, you listen to it on the commute, and then he listened to it on the way home, and then that’s pretty much it. And that – I mean, the complete opposite happened. So many people wanted to start them, and so many people were at home and wanted to listen.

Justin Jackson: Yeah. I was worried about that, too. We were prepared at the beginning of the pandemic to lose 50% of our revenue.

That was like, we’re like, “OK, this could, this could really hurt us,” and we were prepared for that. And by the way, that could still happen. It’s not like I’m like – the one thing about being an entrepreneur is most of my friends who are entrepreneurs do not sleep very good.

Jason Gillikin: I don’t either.

Justin Jackson: And it’s, it’s unfortunate. I mean, I think we can learn to, but you have kind of these dual problems, which is you’re either anxious about something in a, in a worried state, or you’re anxious about something in an excited state. And, there’s always something to worry about. Like you, you just end up worrying about like global politics. You end up worrying about the economy. You end up worrying about, you know, all of these things that are outside of your control.

Or, you’re like super excited about something we’re super excited to build a new feature or to, you know, make this tweak to the thing, or are you getting an idea in the middle of the night and then you can’t get back to sleep.

It’s the worst. It’s like, it’s the, it’s the curse of being a founder. And so, if you really like sleep, I think you probably shouldn’t become a founder. It’s just not it’s, it’s almost everybody I know who’s a founder doesn’t sleep that good.

I wrote a piece called “Good businesses have margin,” or something like that,  and I think that’s something that gets lost sometimes in the advice, like a lot of the advice is like, “Just work yourself to the bone, you know, a hundred hours a week, just pedal to the metal, man! Come on!”

I think, I don’t know. I think that’s BS it. Good businesses should give you a bunch of margin and I, you know, the only thing I have scheduled in my calendar are podcast interviews like this – because I enjoy them – and product demos. And I actually don’t like product demos as much, but I’m willing to do them, I choose to do them, because you know, it’s good for business, but I don’t have anything else in my calendar.

My calendar, my ideal calendar state is empty. And that margin is very nice. And same as, you know, the difference between running a business that was just super close to the metal financially. Like every year I’m like, “OK, well, I really did it that last year. Like we had a good year, but ah, God, I gotta do that again next year and improve on it.”

And it was just exhausting. So, to now have a business that has margin is super helpful. I think eventually we’re going to have to hire somebody, but it’s also been nice to have just a very low head count because when we were going into the pandemic, it wasn’t like I was also stressed about having to lay off 10 people.

We just knew like, “OK, it’s just us full time, and then we’ve got some part time contractors,” and, if anything, actually, what was nice is we were able to really take care of our people and we’ve paid quite a few bonuses since the pandemic started, just because we can. We have a lots of margin to do that.

So yeah, I think margin is important and I’m hoping, hoping it will eventually let me sleep better.

Cee Cee Huffman: So we’ve talked about COVID, we’ve talked about not sleeping, and, when I was doing research for this podcast, I saw that you’d done an interview where you talked about you’d struggled with mental health when you were starting Transistor. And so what kind of advice do you have for somebody who’s like not sleeping, who’s, you know, in quarantine, who’s trying to start this company, and just is exhausted. Like, what would you tell them?

Justin Jackson: Yeah, so most of my mental health struggle happened in 2016 and 2017. And so, as I was coming out of it, that’s when I started talking to John. And, yeah, I mean, there’s a few things.

The first thing is, and this is gonna sound so counterintuitive, especially if you are working super hard to take care of your family and you feel like everything’s riding on you and you, you know, you can’t slow down. This is like, this is, a song, right? “Ain’t No Rest for the Wicked,” you know, you just can’t, you gotta, you gotta like, just keep going.

And the advice is: you must slow down and take time to take care of yourself. So, for me, that meant going to therapy for the first time. And I’m glad, actually, now, so many people are open about therapy and talking about it because, for me, I was always like – I don’t know. I just had like, this awkward embarrassment about it.

Like, I don’t want to – like, I’m going to search for a therapist on the internet, like “therapist near me,” and then I’m going to like, browse profiles and then I’m going to like, how does it work? Like it was – the process was, for whatever reason, like just uncomfortable. The idea was uncomfortable. So even when I was in pain, I didn’t seek anybody out because I was just like, ah, like it’s just too … I don’t know.

But when things got so bad, I was forced, you know, kind of out of my, you know, forced to find somebody. And I did, I just Googled “therapist near me” actually, first I tried a, that like, you know, there’s like online chat therapy and it might be, it might be

Jason Gillikin: BetterHelp

Cee Cee Huffman: Talkspace, or something like that.

Justin Jackson: Yeah, yeah. It might be good for some people, but I think for me, it was just another way for me to avoid this uncomfortable – like, Ijust didn’t want to like, have the uncomfortable thing of having to find a person and sit on a couch and talk to them, but that was the better thing for me. So that chat therapy didn’t work for me, what worked was finding a professional in my area, who – I tried a few different people. I like, went to one therapist and it wasn’t like, a good experience, which is fine, and then I just went to someone else and it was a lot better. And, yeah, I think I’ve seen her now without fail at least once a month probably since, I don’t know if it’s been two years or three years. So, that is a big one. And I pay out of pocket for it. It’s there – I understand that for a lot of people, there’s going to be all sorts of barriers to them going, financial and all that stuff.

But, it is like the one thing I think is worth investing in, at least once or twice. Because especially for men, a lot of men have nobody that they talk to. So, like my female friends, you know, they’ll, have, they’ll go to therapy, but they’ve also talked to other people, but a lot of men just like, don’t talk to anybody.

And, you know, my poor therapist that first time I got in and I just like really, like nonstop, like years and decades of, of stuff coming out. So, do that, take care of yourself first. It’s going to be counterintuitive, but it’s absolutely necessary.

And the other thing is you just need to build margin into your life. And so, this real North American attitude of just like “Go out and do it, like just come on, man. Like, you know, just get it, get in the truck and start driving,” is folly. This idea that we would just be, for example, for me, this idea that I would go independent in 2016. I mean, that was actually not too bad, but I had, you know, a bunch of dependents at home. I didn’t have a lot of savings. Like, one thing that will help a lot is just start with more margin, like start with more money in the bank account. The biggest threat for a bootstrapper is that they will get broke or broken, right? And so, ,f you’re not doing super well emotionally already, it’s probably not a good time to start a company.

As much as you think that might solve your problems, if you are not doing, you know, if you don’t have any money in savings, the pressure that that’s going to create, once you start your business and you’ve cut the cord, is going to be – it’s going to be too much. And so the more margin you can start with the better and, and like, so before you start your company, that’s a good time to, you know, find a therapist.

Even if it’s just like finding a therapist that you’re going to only go to when things get bad or whatever, but at least you’ve made a contact, save up some money, reduce your expenses. You know, gain the relevant skills that you’ll need, gain the relevant connections that you’ll need. There’s all sorts of stuff you can do before you start a business.

That will really help determine whether you’re going to be able to go to the distance. The same is true for podcasting, by the way, most of the work is before you start the podcast, right? It’s like your, your opportunity to promote it is best before you launch your opportunity to build up anticipation, your opportunity to, you know, have some sort of expertise that you can talk about.

It all happens before, and the podcast is just an expression of everything that you’ve done before that moment. And companies are kind of the same way, they’re just – people think like the company is the, that’s where all the development work happens. It actually happens before you break ground.

Jason Gillikin: Hmm. Yeah. That is really good advice, Justin. And the back to the therapist point, like the stigma for men is, is still there to a degree, but not as much, not nearly as much as it.

Justin Jackson: Oh, no, not, not. I mean, one thing that helped me with people talking openly about it, I can’t even remember the, The quote now who had it, it was like a comedian had said this, but something along the lines of like, you can’t just have thoughts jiggling around in your head all the time.

Like, you need to get them out and out a regular basis. And I just never – him talking openly only about it, you know, that helped me go like, “OK. Like, I guess I can’t just have these thoughts in my head all the time. They do need to get out somehow and for there to be an appropriate place to do that. So yeah, I think – I mean, now it’s almost like too cliche, but it’s a good cliche.

It’s like, everybody’s talking about therapy and, that’s a good thing. And oh, that was actually another thing I should mention because I, we have a, there’s a big drinking culture in, in entrepreneurship, too. The first time I went to my therapist and she goes, “OK, the first thing I want you to do is go to your family doctor.” I said, “Why on Earth does she want me to go my family doctor?” And I didn’t. I mean, what, what do I hate more than going to therapy? Going to my doctor. So I get sent to the doctor, and, you know, doctor says, “Why are you here?” I’m like, “My therapist told me to come, I’m depressed.” And she goes, “OK, well, you know, tell me a bit about your life. Are you, are you drinking?”

I said, “Nah, not that much. I have -” She says, “Well, what does not that much mean?” I said, “Well, every night after I put my boys to sleep, I have a shot of whiskey.” I said “Sometimes two on a bad night,” and she said, “So you’re drinking two shots of whiskey, most nights.” I said, “Yeah,” she said, “Well, that’s a lot of drinking for someone who’s depressed. Like, alcohol is a depressant. It makes you more depressed. How many, you know, what kind of drugs are you doing?” I said, “Eh, I don’t really do that many drugs. I like maybe eat like a marijuana gummy every once in a while.” She’s like, “OK, well, I want you to cut that out, too. Here’s what I want you to do, here’s your prescription for the next 30 days: I don’t want you to drink anything. I don’t want you to take any, no marijuana. And I want you to double your exercise.”

And I hated this idea, but I did it for 30 days. It did not help – like, I was like waiting for it to like kick in,  it did not help for the first two weeks – but by week three and week four, I did start to feel better. And, after we launched the company, John, and I said, John, “Let’s do this thing,” ’cause I’d started drinking again. I said, “Let’s do this thing where we don’t drink until we hit $10,000 in revenue.”

And so, I – we did that. And then I just, after we hit the milestone. I just said, “I’m just going to stop,” ’cause it just doesn’t add anything to my life. So, I think for folks to look – again, your personal situation is really going to determine whether you’re broke, or broken. And so, you need to examine these parts of your life that, you know, we just don’t talk about in polite society, but really do impact us. And we need to be able to say these things explicitly, like. You know, like, having a drink every day, just so that you can stay on top of things is, not a good way to live your life and it’s, it’s going, it’s going to have adverse effects on you.

So, you need to consider those things before, you know, as you’re doing your company and, you know, examining your life, not avoiding those things is going to help a lot.

Jason Gillikin: Yeah. I mean, it’s just so easy, right, to, to get a drink after a long day of work.

Justin Jackson: Yeah, yeah. By the way. I’m not saying that nobody should do that.

Certainly, I’m just saying for me that, that like my cofounder still drinks and, you know, people around me still drink. But I think the important piece is to look at that for yourself and to have a clear picture. Like, no one had told me that alcohol was a depressant. And so I’m feeling crappy and, you know, at the end of the day, I’m just like feeling haggard.

I get my boys into bed, you know, I’ve got all this financial stress and everything. It’s like, “OK, you know what I need? I just like need that release.” And it was having the adverse, the opposite effect. It was making me more depressed, right? And then I wake up the next morning. And the, the biggest thing I realized is how crappy I feel like two to three days after drinking.

It’s like, I just didn’t realize I was living my whole life in just like this, like I wake up the next day and I would just feel like garbage, but that was like, it was so normal. I didn’t see it so that – the, I think the point is you just need to look at your own life and bring it up with your doctor, bring it up with your, you know, just, “Hey, I think I should tell you how much I’m drinking,” just to check in like this and to have a third party go, “Hmm. Wow. That’s a lot of whiskey, you know.”

Cee Cee Huffman: I think that’s really great advice for everyone. Whether or not you’re starting a business, but I want to kind of wrap things up on a positive note. So I want to know in these last couple of years, like, what are you most proud of? What is something that you could say to somebody like, “Look what I made, look what I did, I’m so proud of this?”

Justin Jackson: Hm. I mean, I am, I think I’m really proud of the work I’ve been doing on myself. I think that has been just foundational to realize that I am not my work, I am not the success of this business, that I have value and I can like myself outside of those things. Aand I’m still like, I’m still at the beginning of that journey.

So I’m, I am proud of that though. I feel like there’s been some good work there. I’m really proud of the work John, and I’ve done together. I just think, for a long time, I was trying to do everything by myself and having a good partner? Yeah, there’s kind of nothing like it. It’s, it’s, it’s just every day, you know, we wake up and we’re like, “Can you believe we get to do this? Like, this is just amazing, you know?” So yeah, it’s, it’s been, it’s been so nice to work with him. I know some partnerships don’t work out, but I think for a lot of us, like there are times, like Voltron, where the sum of the parts is better than the individual parts, and that’s true for John and I, and I just love working with him. Like if, if I could be guaranteed that I could just work with John and make stuff the rest of my life, I would, I would do that in a heartbeat. Right? What a quote?

Jason Gillikin: What a quote.

Cee Cee Huffman: Yeah, take that clip and play it for him on his birthday.

Jason Gillikin: Well, yeah, Justin, that’s awesome. And we want to be respectful of your time. can you give the audience a podcast recommendation?

Like what do you, what do you listen to? That’s not say, work-related, that you just have, you just listened to for enjoyment?

Justin Jackson: Oh man. There’s so many things. I think “The Jungle Prince” fell under a lot of people’s radars. It was a New York Times podcast. It is just a fascinating story from beginning to end. Yeah, I, I found myself like bingeing. It, it was really, really great. Also “The Missing Crypto Queen” is excellent if you haven’t heard it yet, it again, it just, it hooks you right away, the storytelling is incredible, and you’ll find yourself bingeing every episode. It’s a, it’s a great kind of, escape when you need one.

Jason Gillikin: That’s awesome. And so for our listeners, how can they, find Transistor? Like what’s, what’s the website and why should you know, who’s the right, who’s the right market for you?

Justin Jackson: I think anybody who wants to start a podcast and is pretty serious about it. So whether that’s for yourself, or your company, or your organization, we’re a great fit for all those folks.

And yeah, it’s Transistor.fm. If you’re interested in how to get started, go to Transistor.fm and at the top, I have a “How to Start a Podcast” guide, and I’ve just put a lot of work into that. Helping you find the right microphones and things like that to get started. There’s a, there’s a budget option. And then a more advanced option there.

Jason Gillikin: That is awesome because we’ll do a “How to Start a Podcast” webinar every now and then. So, you know, the, the next one we’ll have to have you on.

Justin Jackson: Oh, that’d be great. Yeah. I would love that.

Jason Gillikin: Yeah. Yeah, for sure. Well, Justin Jackson, co-CEO of Transistor and co-founder of, of Transistor and Cee Cee Huffman, thank you so much for joining us on the Earfluence podcast. It’s been a, it’s been a real pleasure, Justin.

Justin Jackson: Yeah, this was really fun. Thanks for having me on.

Jason Gillikin: Awesome. All right, everybody. Thank you for listening. And if you’re looking for full service podcast production, make sure you visit earfluence.com.

And then if you’re looking for a podcast host, use what we use: transistor.fm.

Full Episode Transcript

The Earfluence Podcast is a production of Earfluence Media and hosted by Jason Gillikin and Cee Cee Huffman.