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Nathan Barry

by Josh Pigford. Last updated on February 07, 2024

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This week I talk with Nathan Barry of ConvertKit! Nathan and I talk about being a maker as a kid, graduating high school at 15, being inspired by working in fast food, deciding when to pack it up or buckle down and much more! Enjoy!

Josh Pigford: All right. Well, thanks for hopping on the call Nathan.

Nathan Barry: Yeah. Thanks for having me on.

Josh Pigford: One thing I talk to a lot of founders about here is, like them as a kid. I think that’s fascinating. It’s like what were you like as a kid. What were you into?

Nathan Barry: All right. Let’s see. I was super shy as a kid. I didn’t like talking to other people, but I was always into making stuff. My dad had a woodworking shop, he built the house that we grew up in. He didn’t have fancy tools, but he always had plenty of tools. He built … I grew up building swords and crossbows, and all the important things that you should build as a child. Then I probably had my first entrepreneurial experience with woodworking and doing things like that, probably when I was like 10 or 11. I’d make like these different wood crafts on a scroll saw, and then sell them around the neighborhood. I was always into always making stuff, and I had that modeled for me a lot.

I guess it’s probably the two biggest things I had modeled for me from my parents were, just always build stuff, like even if you have no idea what you’re doing, like you can figure it out. Then also the second one would be from my mom, and that was just like always learning things. Because she would just be like, “You know what? Actually I decided I wanted to learn Greek, and so I’m going to spend all this time learning Greek, because why not?”

Josh Pigford: Do you think the … I mean did entrepreneurial stuff come from your parents at all?

Nathan Barry: Somewhat. They never did no stuff in like the traditional sense, but my dad ran a Christian bookstore, for 20-some years or so, and so that was never designed to be like a money-making venture, but it has a lot of the characteristics of the typical entrepreneur path. I’m sure it has the same emotional rollercoaster of being an entrepreneur as well.

Josh Pigford: I worked at a Christian bookstore for a couple years.

Nathan Barry: Nice.

Josh Pigford: It’s interesting. I only thought I was getting robbed a couple of times, so it was fun.

Nathan Barry: Actually robbed at all?

Josh Pigford: No. Never actually robbed. Just people … shady characters walking in and then me not being able to understand what they were saying, and me just assuming that they were trying to rob me. This is like as a high school kid. I mean the store was in a bad part of town, where gunshots were not uncommon, and we’d had people like break windows and stuff and steal Jesus statues as one does.

Nathan Barry: Yeah. That and Bibles. It’s pretty common.

Josh Pigford: Right. You know? I mean, what else? There’s not anything else to steal in there other than that.

Nathan Barry: Yeah.

Josh Pigford: It’s interesting that you mentioned you making things like swords and stuff out of wood, and then like wanting to sell them. The typical kid entrepreneur thing I would say is more … tends to be almost like more service-based stuff, like I cut grass for years and years and years, but do you … for you was it more you making a thing and then trying to sell that, or were you also into the like, “Let me do some service for someone.”

Nathan Barry: It was usually making things, and it’d be like these … you know I grew up in the mountains outside of Boise, and so like using a scroll saw and make these like … I don’t even know how to describe it but like kind of this animal carving of sorts, but like a two-dimensional animal carving. Like a relief carving of sorts, and sell those around. They were relatively easy to make, and because it was like up in the mountains and like all these mountain animal themed things would sell really well. Everyone was like, “Oh yeah. Of course, I want to buy this thing that this 12 year old made.” That was actually pretty decent, you know?

I think we did this only services thing, other than like a neighbor saying, “Hey can I hire you to stack all this firewood,” or something like that. We had some friends who lived maybe a mile away from us or so, and then when they moved away they had this pet sitting business of like, “Hey. You’re going out of town. We’ll check on your pets once or twice a day.” They gave that to us. To me and one of my siblings, and that made good money. Because it was just like, ride your bike over to the neighbor’s house, take care of the pets, and the rate was like 10 bucks a day. I just remember being like, “Wow. This is good money,” so I did that for a while.

Josh Pigford: Growing up in the making stuff, kind of selling some of that stuff, I mean was it something where you kept doing that all through … I don’t know. Even through high school or did it sort of like die off as you got a little bit older?

Nathan Barry: It probably started to die off as I needed to earn a bit more money. All my friends were a couple years older than me, and they were starting to go to college, or they’re starting like senior year of high school, and started thinking about going to college, and so I wanted to go to college as well. But like didn’t have the money to afford it, and I worked out this whole thing with my parents where I let the … they would list out the exact work that I needed to do. Like, “Okay. You have to go this far in math. You have to like … as long as you complete precalculus,” and all these things, in all these different areas, then you can consider yourself graduated. Because I was home-schooled, and so instead of spending four years in high school I just got this giant checklist of everything had to be done, and like went through all of that.

We would take these eight-hour drives to visit family in Seattle, and I remember thinking like, “Well I’m really bored doing algebra, and I’m really bored on these eight-hour drives, so I don’t want to just combine the two.” I would do like a month or a month and a half worth of math lessons on the drive to Seattle.

Josh Pigford: In the car.

Nathan Barry: My older siblings would be there in the car with me, and so like I could ask them questions, and you know, they had nothing better to do than answer and like explain [inaudible 00:07:18] to me.

Josh Pigford: You’ve trapped them in the car. They can’t go anywhere.

Nathan Barry: Yeah. I was able to get really far ahead, and so I graduated high school not long after turning 15.

Josh Pigford: Wow.

Nathan Barry: The whole point was, so I could go to college where my friends were going, which is Boise State, but I needed a way to pay for it. Because there were scholarships that I could get, but then oddly enough a bunch of them I couldn’t get because I was too young, and that was frustrating, but I remember picking up the phone book and like going through to all of like the fast food places, and just calling them asking them, “Hey. What age do you hire at?” They’d all be like 16. I’m like, “Dammit,” and then move on. Then Wendy’s was the first one that that said, “Hey. We’ll hire at 15,” and so that kind of ended the … I guess the selling things around the neighborhood.

Josh Pigford: Was fast food.

Nathan Barry: To fast food. I mean it was more consistent money, and then that’s how I paid for like the first year of college tuition.

Josh Pigford: Was working at the fast food? Oh man. That’s fantastic. How long did you work at Wendy’s?

Nathan Barry: A year and a half, two years. I think year-and-a-half. I got an internship-

Josh Pigford: Did you like it?

Nathan Barry: Yes I did actually. Because they had every … Okay. This is me nerding out in business now. They had everything down to a perfect system, like just flawless. Where you could take like any person who had no idea what they’re doing, only kind of wanted to be there, and get them to fill their role in this perfect system. There was like three or four of us there that kind of became obsessed with streamlining it even more, and we started this rivalry with this other … with two other local Wendy’s locations, as to how fast we could serve everyone through the drive-through, during the lunch rush.

Because there was this timer, and it would keep track of every car from when you pulled up to the speaker, to when you left with your food. We would call him off to me like you know, “I don’t know about you, but we’re going to pull off 82 seconds today. What are you going to get? They’d be like, you know … We would get this rivalry going, and we would pick or be like, “I don’t know. Joe can’t. He’s not going to be making sandwiches or working the grill for us today. We need somebody better.” We were like who was …

Josh Pigford: That’s super cool.

Nathan Barry: … super efficient. We’d actually have a really good time, because at one point we set the … I can’t remember the numbers from it, but people from like Wendy’s corporate showed up, and they were like, “Hey. By the way, I don’t know if you guys know this, but you guys are consistently setting like the national record.” They’re like, “How fast you’re serving everyone through the drive-through.” We were like, “Cool. Because we’re having fun doing it.”

Josh Pigford: That was the goal.

Nathan Barry: Yeah. I didn’t realize they kept track of it on like a national store scale, but yeah. We had a lot of fun, and I just loved … I loved working really, really quickly because all throughout high school, college, I mean yeah all throughout everything, there had been this idea and granted me by my parents that, “Hey. Don’t do anything for a set amount of time, just do it until it’s done, get it done as fast as possible.” I remember sometimes … being homeschooled sometimes school for a day might take five hours say, but if it was snowing outside, and we wanted to go sledding, it’s amazing how like it wasn’t … my mom never said, “Okay. You need to sit here for five hours and do all the stuff.” She was like, “Yeah. There’s all the homework. There’s all that stuff that you have to get done, and when it’s done you can go sledding.” You can get five hours of work done in an hour and a half, if you’re motivated enough to go sledding.

Like Wendy’s fed into that of like, “Oh no, we’re just going to …” Obviously we still got paid by the hour, but we were able to make it fun of like. “Okay. How can we perfect this system,” and whatever everyone else is like slogging through we’re just like, “No. No. No.”

Josh Pigford: You were like screaming at other people, “Faster. Faster.”

Nathan Barry: Yeah. We were probably. I was like a 15 or 16 year old who’s like-

Josh Pigford: Everyone hates you.

Nathan Barry: We was like five of us, so we had the most fun.

Josh Pigford: That’s so good.

Nathan Barry: I always applied that to everything like … when I started doing freelance web design, which I guess I got into that because I dated this girl in high school who was like making websites on GeoCities, back when the animated gifts were not like jokes, but like … I mean for herself.

Josh Pigford: That’s like how you design stuff. It was an animated sparkly under construction gif.

Nathan Barry: Yeah. Exactly. So it was a lot of that stuff, and I remember when she showed me like, “Hey. Look at this thing that I made,” and I like typed this hex code into notepad, and then like the background color changed. I thought that was super cool. Once I learned web design and started to get clients, then I had that same approach of like, “Oh no. No. I’m not going to bill by the hour, because that doesn’t reward me for the one thing that I’m super good at, which is being really, really … like getting results really quickly.” I would always billed by the project.

Josh Pigford: Okay. So you’re working at Wendy’s to pay for college, did you … I mean did you finish college?

Nathan Barry: No. My claim to fame when it comes to college is that I dropped out at 17, so after two years, and before most people have the chance to drop out of high school.

Josh Pigford: Right. Right. Right.

Nathan Barry: I did two years at Boise State first for a graphic design, and then I decided I hated the art department. Because when I said graphic design I meant like all the stuff that I was doing in Photoshop and then starting to do on the web. When they said graphic design they meant art, and I was like, “You and I don’t see eye to eye on this.”

Josh Pigford: When like-

Nathan Barry: So I switched to marketing.

Josh Pigford: Did you enjoy the marketing stuff?

Nathan Barry: No. Because I never got into the marketing classes. I got so stuck in intro business that I don’t know … another year and I would have gotten into like the actual … I don’t know, 300 level marketing classes. I might have liked that but.

Josh Pigford: Did you drop out because you were bored or because just like paying for was tough or?

Nathan Barry: I dropped out because I was in school to learn how to make money, and to get … so like for a career to earn more money, because I really like to earn money. I was starting to … like my freelance web design stuff was really taking off, and so I realized like, “Wait. I’m probably making as much money now as I would expect to make out of school, but I’m also still paying for school and I like making money more than spending it,” and so-

Josh Pigford: I’ll just keep the money.

Nathan Barry: I’ll just not. Boise State’s not an expensive school. I don’t know what it was, like 6,000–7,000 a year. It was probably more than that, but somewhere right in there, but I was like, “You know what would be better is if I just worked.”

Josh Pigford: Than spend.

Nathan Barry: Yeah. I got like a $5,000 web design gig, and then like a $10,000 full apps offer design gig, where I had to like contract out some of the development. Then I was like, “Okay. I think I can make this work.”

Josh Pigford: Did you immediately go from dropping out of college to doing the freelance stuff, or did you go work somewhere?

Nathan Barry: No. Immediately into the freelance stuff. I was freelancing through college. Basically, as it took more and more of my time and had less time for school I was like, “Maybe I just won’t go back this semester.”

Josh Pigford: Okay.

Nathan Barry: Yeah. Then I freelanced for about a year, and had a really good year of freelancing, and that put us in early 2008 or … let’s see. The end of that year was end of 2008 and early 2009, and I went on a five-week trip to South Africa. I didn’t make any money during that time, and then when I came back like beginning of 2009, it was solidly the recession. I heard from a bunch of people, like I went to pick up all these conversations that I’m having I’m like, “Hey. Let’s start a project,” and everyone was like, “Look. We’re not spending money till our clients spend money.”

Josh Pigford: Yep.

Nathan Barry: Then I had one client who was like, “We have freelance work, but we’d really prefer you join full-time.” I ended up joining them to lead their software design interface stuff, and I was there for three years.

Josh Pigford: Cool. What kind of software were you guys designing?

Nathan Barry: We did a bunch of stuff, but it was a lot of things around video delivery on the web, so particularly for like hospitals and patient education and stuff like that. It was a very small company when I joined. Of like 14 people and like-

Josh Pigford: Were you guys an agency technically or were you guys actually building software?

Nathan Barry: Actually building software, and then selling it. There would definitely be services works that came along with it in order to make the sale, but it was set up as a software product, though like more enterprise sales type of thing, rather than you know … They were like selling 100,000 to million dollar deals rather than like, “Hey. Sign up for this for 500 a month.” There’d be custom dev to go with it, and then we had a video production department eventually. It like grew … it was 14 people when I joined and grew up to like 90 people.

Josh Pigford: That’s cool.

Nathan Barry: Yeah. But they was all like VC funded and it went down the other side as well.

Josh Pigford: Was this in Boise?

Nathan Barry: Yep. In Boise.

Josh Pigford: Got you.

Nathan Barry: Yeah. They raised like 30 million in venture capital over five years or something.

Josh Pigford: This in the early two … or I guess late 2000s.

Nathan Barry: Yeah. Because I joined 2009, and then left the very end of 2011.

Josh Pigford: Okay.

Nathan Barry: It was quite the ride.

Josh Pigford: You’re there for three years, and then I guess what made you want to leave working for them to go back to doing your own thing?

Nathan Barry: Yeah. I’d wanted to go back to do my own thing for a while, but I wanted more stability in it, and so on the side I started building iPhone apps and got those … a couple iPhone apps to the point where they were making a couple grand a month pretty consistently. My idea was like, “Hey. If I go back to freelance, but I actually have this stable like baseline cash flow of like,” I don’t know. In Boise especially as a single guy, though I guess I was married at that point, but married no kids, like you can live I mean not great, but you can get by on $2,000 a month sure. I was like, “The iPhone apps can cover that,” and then like other things … then I’m actually going to freelance on top of that. But the idea that my worst month ever could be $2,000, like that makes freelancing a really great idea.

Josh Pigford: Right. Right. Right.

Nathan Barry: Like cuts the valleys out of that emotional rollercoaster of like business cash flow, but anyone who has freelanced has experienced.

Josh Pigford: Sure. Totally. You mentioned you were married at that point, so like what was your wife’s response to quitting your job to go back to being self-employed?

Nathan Barry: She knew I wanted to for a long time. She was totally in favor of it. She’s just always been ridiculously supportive. Because I actually left my job two weeks before our son was born so yeah. It was kind of a good reminder of like, “I don’t want to be doing this. Life is moving forward it’s time to …” and the other company was having layoffs. After you go through a couple rounds of layoffs and you still have your job you’re like, “That’s great, but I don’t want to be here anymore.”

Josh Pigford: Well like the stability being like one of the reasons that you even have the job in the first place, kind of becomes clear that there’s not really anything such as job stability, right or?

Nathan Barry: Right. I’d think of that as like, “Oh great. Now there’s a single point of failure. Instead of freelancing at least I have five.” Five points of failure of like you know, I’ve diversified my income slightly, so that if one client fires me, I’m not like desperately searching for income.

Josh Pigford: Right. All right. What was the plan? Were you interested in building like a company at all at that point, or was it just about being self-sufficient?

Nathan Barry: Self-sufficient, but I wanted to do products. At this point I’d done freelancing for quite a while. I guess quite a while it’s all relative, but I’d done that kind of thing, and I tried to like productize it as much as possible of like, “Hey. I’ll build this iPhone app for you for $10,000,” rather than like, “Yeah. Let’s see where the hours end up.” I really wanted to sell products. All the blogs that I read were … like if anyone was talking about hey I made this much money from an iPhone app, like you better believe that I read that article. Or like details on growing an audience, or all that stuff. Self-publishing books or courses, I read all that stuff.

That was always the goal of, “Okay. How can we get to selling products?” So the iPhone apps are the first products there, and then I ended up writing a book called The App Design Handbook, and that did you know … that was my first experience like selling to an audience, because I’d built up a pre-launch list for that, and it sold $12,000 worth in the first 24 hours. I was like, “Okay. There’s something here. Let’s stop freelancing,” and now I’m … like all of a sudden I’ve gone from like, “Let’s put this thing out here and see if it sells,” to like, “Yep. I’m a professional blogger and content creator now, and like I’m going to write another book.”

Josh Pigford: I’m curious like how you even arrived at the point where you decided … like the idea to even do products instead of consulting, or some sort of services. I mean how did it even register for you that, “Hey. Maybe I could you know do these things.” Either both the consulting as … like you’re selling a full product package deal instead of hours, or even just writing an e-book and selling that. Like how did that end up on your radar?

Nathan Barry: Yeah. That’s a good question. It probably started with like 4-hour workweek. Trying to think when I read that. It was probably 2008 or something, and that’s kind of got me thinking down that road of like opening up those doors, and then from there … from Mike Tim’s blog I ended up finding Chris Gila Beau’s blog and he talks a lot about like audience building and selling digital products. Then being in the software space, I’d always read all the stuff from the guys at Basecamp. Kind of that mix of things of like, “Okay. I’m starting to see the power of products, the power of audience,” and just getting like totally immersed in this world.

Josh Pigford: The idea of ConvertKit, was that just sort of this natural evolution of, “Hey. I’ve sold ebooks, I’ve sold apps. I’ve sold my consulting even as its own sort of little product,” was a SAS product sort of just the natural next thing to try, or I guess what was the motivation to do that?

Nathan Barry: Yeah. A couple motivations. One, at that point I’d written and sold two books on designing software, and I felt like I was talking about how to design software, but was starting to get out of experience, and like I hadn’t actually designed any software in a while. Which I remember that feeling pretty strongly, though now when I look back on it, it had been like five months that I hadn’t done any software design, and I felt like, “Man. I’m getting so rusty, like I just … I don’t know. I feel like a bit of an imposter, like telling people how to do this, and I don’t even do it at all anymore.” Now looking back it was like five months max. Maybe I didn’t need to feel that as strongly as I did. Looking back on that, that was part of it. I wanted … like my background is software design. That’s my skill set, so I wanted to actually be designing software again.

Then the other part is, I’d done these two launches. One had done 12,000 in 24 hours, the next one had done like 24,000 in 24 hours. I started to see like, “Okay. There’s these big spikes, but there’s this valley that comes after it.” Actually those two launches were so close together that I don’t even know why I was concerned about this, because it’s what I brought in quite a bit of revenue. Looking back then I was like, “Oh man. I don’t want to be stuck to this launch driven model. I want recurring revenue,” and so like those two things made it so I was like, “Okay. It’s time to start a software company.”

I didn’t know what software company to start, but I launched into it publicly, said, “Hey. I’m going to build a software company, you can follow along on my blog.” The goal was to get to 5,000 a month in revenue, and in six months, and then ConvertKit came pretty quickly because I was like, “Actually I need a better email tool. Like all of my sales are coming from email. I can do better than MailChimp, and build something just for myself.

Josh Pigford: I love how that … like the impetus was … so you’ve got existential crisis from like not designing something for a couple of months, and then launching really successful ebooks that make you tens of thousands of dollars in a short period of time, and you’re like, “This isn’t enough. I need software.” But I mean hey, you know, so be it. So you do like this, I don’t know, self-described like web app challenge thing. You build ConvertKit, launch that, the goal was to do what? $5,000 an MOR in six months like that didn’t happen.

Nathan Barry: Right.

Josh Pigford: It was kind of like two years of ConvertKit just like sitting there more or less, right? You’re doing ebooks at the same time, or you’re still like at this point just basically living off of the prior sells of e-books?

Nathan Barry: I’m still doing ebooks. So I got to the point where pulling in about 200,000 to 250,000 consistently every year from ebooks, and so that was the primary driver of everything.

Josh Pigford: During the first couple years of ConvertKit, are you even working on ConvertKit much at all, or is it still just like the e-book thing kept working, so you were trying to do both?

Nathan Barry: I was doing both. So I put probably 20 hours a week into both, and then another 10 hours a week into all the other goofing off of like learning stuff and trying things out, and you know that kind of thing. Like that work where it’s like you do a full workday and then you hang out with your kids and family and all of that. Then like somehow at nine o’clock you find yourself back to the computer for an hour and a half.

Josh Pigford: Still doing something but not sure what?

Nathan Barry: Yeah. Exactly. I did lots of that.

Josh Pigford: Lots of that. Okay. In the first two years of ConvertKit, I mean growth for the most part declined. I mean you got up to a certain point, but it also was just less.

Nathan Barry: Yeah. 2,000 a month or I think 2,200 a month was the all-time peak. Then it kind of just tapered off from there. Like it’s a flat and then tapered off. Then I started to lose motivation. I was like, “I can’t make this thing grow.”

Josh Pigford: But why do you think growth actually declined over those two years instead of grew?

Nathan Barry: I think we weren’t mature enough as a product. I wasn’t putting in super consistent marketing efforts and it’s … like if something’s brand-new, it’s easy to get people to be like, “Cool. Check it out.” Like there’s this exciting factor of it being new. Then people will quickly realize like, “Oh. This doesn’t have everything that it needs to, like all MVPs.” But then if they see it improving fast enough, and they like you, and they like the direction of the product, then they’ll stick with it. But if it’s not improving fast enough, then they’ll just bounce. So we had a lot of that, of it just … like I was building it on such a cash constrained budget of like just trying to make it fund itself, that they’re just like … you couldn’t hire enough development time. You couldn’t. It wasn’t really making progress.

Josh Pigford: But do you feel like you had spent the prior few years on this ebook sort of sales cycle, where you build up some hype to an e-book launch, and even though you could sort of relaunch the e-book over and over again with updates and whatnot, and different pricing packages, but it was still based on these big surges of press or signups and all that. Do you feel like that hurt the initial launch of ConvertKit? Like were you focused on almost like treating it like its own … like it was an e-book?

Nathan Barry: About a year in I tried that again, of like a different model. Because yeah I really only knew how to sell ebooks, and that launch driven model, and that’s hard to do with SAS. There’s a few companies that still continue to do it, and now I kind of make fun of them. Because I’m like, “Guys, you don’t really use version 5.0 of your SAS product.” Like the moment you put a version number in your SAS, like all of us software guys start making fun of you. But I didn’t know how to drive like these consistent sales. I knew how to build up the hype and then have urgency in a launch, and do all that, and so that ended up being hard to drive consistent sales.

Josh Pigford: Yep. Yep. Then what happened? Two years in you know growth is actually lower than it was earlier at the early days of it, but then something changed. I mean like what changed for you mentally, that ultimately resulted in some change in growth?

Nathan Barry: Yeah. I was at Micro-Con in Vegas, and had a conversation with [Heaton Shaw 00:31:24] and he was like, “Hey. You should shut down ConvertKit.” I remember thinking like, “That’s not a nice thing to say dude. I’ve put a lot of work into ConvertKit like don’t just tell me to shut it down.” But then he continued and he was like, “Look. You’re going to be successful at whatever you … like you’ve proven to … like you can make money on the internet. You can build an audience. ConvertKit is not working. You should shut it down or take it seriously, and like go all-in on it, and give it the time, money, and attention it deserves and you can build it into something real. But like clearly whatever you’re doing is not working, and so shut it down or double down.”

I always joke that I did what everyone does when they hear really good advice, and that was waiting six months to take any action on it whatsoever. I went from like … he told me that in … it must have been April, and in October I was like, “Okay. I got a decide. Like I’ve got to shut it down or double down.” That’s because it wasn’t even covering like its email sending infrastructure, like basic bug support bills anymore. I basically decided, and I wrote a whole blog post on this but you know … should I shut it down or double down? I came over the simple two question framework, and the first one was, do you still want this as much today as you did when you started? So for me it was like, I can sell ebooks and courses all day long, and I don’t … like I’m not the … I’m not going to complain about only making 200,000 a year 250,000 thousand a year, like that’s a great business.

So do I actually even want to like go down the software route? Do I want to be like the CEO of a software company? And if not that’s totally fine, just like shut it down, walk away. That’s fine. No one’s going to think any less of you. And I thought about it and I’m like, “No. I still want this just as much as the day that I started.” I was like, “Okay.” So I proceeded to question number two and that’s, have you done everything possible to make this succeed? When I thought about it, like have you given this every possible chance? And so when I thought about it I was like, “Well, okay. I have only put in like $5,000 of my own money. I’m working on it part time, and like my attention as is, like going to these other things,” and so I was like, “No. If I shut it down now, I’ll always have this nagging feeling of like, “Could I have made that work?” That told me that, “Okay. I need to go in on it,” because there was this disconnect between what I say I want, and then the amount of effort that I’m putting in.

So I needed to actually give it like a real try. To me that meant actually hiring an in-house developer, so not just contractors, but hiring someone in-house who could focus on it full time. Investing a real amount of money, so all the money I had was $50,000 in savings, so I put all of that into the company. Then actually like trying new sales tactics. So instead of selling through content, I started selling through direct sales, and that really started to kick things off. We were at 1,300 a month in revenue, I guess the last thing was picking a specific niche, so changing our marketing. We went to email marketing for authors, and then eventually email marketing for bloggers. Focusing on that we went from 1,300 month in revenue to 1,600 a month mostly through those direct sales. Then 2,000 a month and 2,500 and then 3,000.

Six months after that decision, we were at 5,000 a month in revenue, and then by the summer … so that was in April. By June, we were at like I think 10,000 a month and then July was a fantastic month it was 15,000 a month. We started to get some more influential customers. Then a few months later they started talking about it, like Pat Flynn and others, started saying like, “Oh yeah. We use ConvertKit.” Then that 15 turned into 18, to 25 and by the end of the year we are at 98,000 a month. So in 13 months or 14 months, we went from 1,300 a month to 98,000 thousand a month.

Josh Pigford: That’s not too bad.

Nathan Barry: A little work.

Josh Pigford: Yeah. Okay. So let’s backtrack a tiny bit here. You mentioned the $50,000 in savings, so at this point you’ve got … you were very much married, you’ve got kids. I mean spending your savings to make this thing happen, that two years prior has very much not worked. I mean like what was your wife’s response at that time? I mean obviously she was super supportive going to be self-employed, but now it’s like you’ve got … there’s a lot more at stake at this point.

Nathan Barry: Yeah. We’d been making good money but had just bought a house, and that was like a $60 or 70,000 down payment and then spent about $80,000 remodeling it. We’d gone from having like a really good nest egg in savings to like okay this 50,000 is all we’ve got left. Part of the reason for that, there’s a part of the story that I don’t tell that often, and that’s when my second son was born. So when would that have been? 2014. May 2014. He was like the easiest kid ever. Like the first two weeks I was like, “Wow. This is fantastic.”

Then both kids got sick at the same time, and we had all these other stuff going on. We were remodeling the house. I was the general contractor on the remodel, still running my blog and everything. What ended up happening is at one point I noticed this … like both kids were not sleeping, and they would do the thing that I’m sure you’ve probably experienced, where they’re like … the kids decide to alternate when they’re going to wake up. They’re like, “Don’t worry. We’ll wake up every two, two and a half hours, but we’re going to take turns.”

Josh Pigford: Then it results in you getting zero sleep.

Nathan Barry: Yeah. I remember like you know … my wife’s just given birth to this kid like two weeks earlier, so I’m going to be … I’m going to like step up and do my part, and so I tried all of that. I ended up getting no sleep, but then one day I noticed this like rash starting to develop on my leg and I was like, “That’s weird.” I was thinking like diet or laundry detergent, or like you know, something’s different. I eventually go to the doctor for it and they’re like, “Yeah. You’ve got shingles,” which I thought only old people got but-

Josh Pigford: All sleep-deprived parents also.

Nathan Barry: Yes. They’re lik, “Is there anything going on in your life that would cause you to like have an increase of stress?”

Josh Pigford: I haven’t slept in three weeks.

Nathan Barry: Yeah. They’re basically like, “That’ll do it.” I remember they were like, “Here’s some antivirals to take,” and then also like, “Here’s a prescription for painkillers.” I was like, “That’s okay. I’ve got all this business stuff that I want to get to, and I don’t like what painkillers do to my head. I want to think clearly and the pains, you know, it’s frustrating but it’s not significant.” They’re like, “You sure?” I was like, “Yes.” Then turns out they had a bet going in the office as to how long it would be before I called them back to ask that prescription. Took five hours, and they were just like … so when I called I was like, “Actually can you call in that prescription.” They are like, “We already did. We were just waiting for you.”

That kind of resulted in like five or six months of like getting over that … three months of getting over that, and then it took me six months or more before I felt like I got any level of productivity back. I don’t if you run into this, but for me like I drive a lot of my self-worth from what I accomplish, and so it ends up being kind of this downward spiral of like I don’t know, productivity, depression, like all that. It’s just like I can’t get work done, and because I can’t get work done I’m even more down, and so I am even less able to get work done. I actually had this as a conversation with Hillary, my wife, and when we were deciding to double down on ConvertKit, like kind of at the end of this period. Maybe someday I’ll use this in a podcast or something, because I have it recorded, but I’ve heard her saying like, “Yeah. I was totally supportive of going all in on a ConvertKit because I didn’t know what else you would do. Because you didn’t really do anything back then.”

Josh Pigford: You just stared at a wall.

Nathan Barry: Yeah. I’ve got that before. Like We had enough money coming in from the ebooks that like you know, the mortgage wasn’t going to fail, but like all of that had dropped off. It had gone from averaging 20K a month down to like 8K a month or something, and was not on a good path. She was just like … she was totally supportive.

Josh Pigford: Do you feel like on some level it was almost like she had seen you just being so down and not productive or anything, for nearly half a year that it almost felt like you needed something to get excited about?

Nathan Barry: Yes. She was like kind of willing to try anything at that point. She was like, “Well, he seems excited about like … he seems to at least have some direction on this, and so it seems worth trying.” She was saying like, “Look. Worst-case scenario is if all of this doesn’t work, then like we sell the house that … or default on the house that we just bought and remodeled,” and like move in with her parents or something. I was like, “No. No. No. Worst-case scenario is like I start doing some consulting again or something.”

Josh Pigford: Sure. Sure. I think like-

Nathan Barry: So her worst-case scenario was way worse, and she was totally fine with it.

Josh Pigford: She was still fine with it, right? Like I think there’s a pretty common thread from talking to a bunch of other founders about this kind of stuff too is especially … I mean founders that are married and maybe even have kids, having your spouse or partner be not only just supportive, but have like a pretty high tolerance of risk, or like being okay with the ups and downs, and being able to absorb that pretty well, it’s pretty common thread. Also I mean super helpful.

Nathan Barry: Hillary is. Yeah. Hillary has an amazing … I don’t know, and anything that she would do personally, she has a super high risk tolerance, but like she’s very tolerant of me taking on large amount of stress.

Josh Pigford: Do you think you know … you put all these changes into place, you know, spend 50,000 of your own money, really double down on doing direct sale stuff, the outreach, all that kind of stuff. Do you think you could have done the same set of changes two years prior to the same effect?

Nathan Barry: Yeah. I think so. Maybe it was also like me getting to a certain point or like an amount of dedication or something like that. But yeah, there is nothing magical about waiting. I remember actually telling [Heaton Shaw 00:43:36] … later on I was like, “Hey. I finally decided to take your advice and double down on this,” and him being like, “Cool, but it might be too late. Because like ActiveCampaign is doing a bunch of great moves, like Drip had kind of a flat period for a while, and they’re seeing a resurgence, and they’re like making a lot of traction now. Like Aweber is doing all these updates.” So he was like, “Look,” I don’t know if he told me this, because he like 100% truly believe it that we were maybe a bit too late, or he wanted to just like motivate me even more. He was like, “Look, you may have missed the opportunity. Like I gave you the advice six months ago, and you got to realize that six months is a long time in the startup world, and you might have just missed it.”

Ideally if we’d come out with the … like I think in the first six months of ConvertKit, I wouldn’t change much about what I did there, but from six months on, like if I could have maintained that momentum and started the direct sales, and like I think it would have changed the trajectory of the company for sure. We easily could have shaved two years off of the growth plan and everything else.

Josh Pigford: Which you know, if six months is a long time, I mean two years? That’s pretty significant.

Nathan Barry: Yeah. But I mean at the same time I learned a lot. I certainly don’t have any regrets from the process, but it’s like, “Yeah, if I would have started like the direct sales and get out there and hustle a lot sooner, like ConvertKit would be a bigger company.”

Josh Pigford: All right. Okay. So the past two years, you guys have had a lot of growth, so you went from making a couple thousand dollars a month to like today you guys are doing almost 10 million a year. What’s been the hardest part of that, like either, I don’t know, mentally …not so much from a product standpoint, but like what’s for you been like this really hard part about managing basically nothing to 10 million?

Nathan Barry: Yeah. Well, the first thing is like growing and staying profitable is super hard, and so it ends up being really stressful to like not have cash in the bank. There were times when we’re doing like 100K a month in revenue, and had like 97,000 a month in expenses and 30,000 in cash in the bank. We realize like, “Hey. Our cash balance is growing every month,” but our cash balance as a function of days worth of expenses is like … you know last week we had two weeks of expenses in the bank, and now we have slightly more money but it’s really only 11 days of expenses now. That was definitely hard and definitely stressful. Then I was like, “Okay. Now I get why people raise money.” Then like later on, you know, the next year we did … so in 2016 we did a million dollars in profit on $4.1 million in revenue, because we like shifted so far to be like, “Okay. Let’s get as profitable as possible.”

Then what really sucks is like paying out so much of that in taxes. Like 450,000 of that goes to taxes. It’s like, “Wait, we just built up this like nest egg,” and then it’s like you have to pay taxes on, so that’s like another advantage of … I don’t know why I’m giving all these advantages to raising money, but it’s coming to mind right now. Even though I’m glad that I didn’t raise money. If you get this cash in you’re not having … like you get this nest egg that you can count on, and you get it right away, rather than having to like … like it’s just so much work to save up that cash on hand.

Josh Pigford: Well, I think a lot of people also … the other alternative there is to spend some of that. Like to operate, not necessarily like right at breakeven but I mean if you spend some of that, then you’re not having to pay as much on taxes, which I think a lot of companies do, but like that’s a fine line too. That kind of like … the stress that you mentioned about profitability, you know, it kind of maintains the stress, because you have to keep up the stress operating at near breakeven.

Nathan Barry: Yeah. I think so. You just have to like … we weren’t disciplined with our books and finances until you know, as we got into 2016 we started getting all of that together. At some point you’re just watching the bank balance. You’re seeing the stripe deposits come in every day and you’re like, “Hey. Watch that. That’s great. That’s growing.” Then you’re like, “Oh shoot. We ran up 40,000 on the credit card and like … Like earlier on you’re watching the cash flow from that perspective, and maybe not from an accounting perspective, and you need both really. Because I’ve seen people get so caught up in accounting and they’re like, “Based on our accrual accounting methods we’re,” and you’re like, “Yeah. Like you’re accruing that expense over the next 12 months, but you had to pay for it today. So, here’s the deal, you don’t actually have that money that …

Josh Pigford: You think you have.

Nathan Barry: … that your book said. Yeah and so I don’t know, that was definitely a stressful time. I’m trying to think about other things that have been particularly rough. Like management-

Josh Pigford: The growing the team. Has that been an enjoyable thing for you?

Nathan Barry: For the most part. There are some early learnings. I had to make a pretty key fire. Maybe about that time that we were like 110, 120,000 a month in revenue. That was painful because the … probably half the team, or a quarter of the team for sure, thought that that was … like letting this person go was totally the wrong move. It ended up being totally the right move, but it took a lot of convincing as they’re like … and I just made the call.

Josh Pigford: There’s just a huge psychological, right? I think that’s the hardest part. Like building a team is like … you’re a CEO and resident psychologist that’s having to like balance the needs and human emotions of a whole group of people.

Nathan Barry: Right. That was rough. Also just like scaling the product, like from an infrastructure side of like … we now send hundreds of millions of emails every month, and then, “Oh you know what would be fun today? Like a denial of service stack. Let’s do that. That sounds great.” Stuff like that. Like our first team retreat, we’d finally … which was a big deal and it’s funny to look back on now, because I can remind some of the early people like, “Hey. Remember when we were just trying to save up enough money so we can have a team retreat?” When we were like, “Let’s do a team retreat. Oh wait. We can’t afford it.”

When we finally went on our first team retreat, which was last summer, so August 2016, we got like this denial service stack that the day that we’re all supposed to start doing things. It was like paddle board trip. We were all going to go paddle boarding down this river, and then all the engineers are like, “Actually, we’re going to sit in this coffee shop and like do whatever we can to fix this, because who knows what’s going on.” That was painful. Like customers were upset, as like we had all kinds of trouble scaling, and obviously we got through it but it’s still a pain.

Josh Pigford: I mean the … anything other than the infrastructure sort of scaling, the things that come with that. Besides that is there any other part of the fast growth that you have not enjoyed?

Nathan Barry: I don’t think so. I mean fast growth is generally a good thing. Because it brings … like it’s stressful and I definitely felt like for a year or more, I was just on all the time, and like … and so my wife likes to point out that she’s like …Well, I’m going to get my hair cut. This is like, I don’t know, four months ago or something, and the person cutting my hair was like, “Oh yeah. You got more gray hairs coming in here.” I was like, “More gray hairs? I didn’t know I had any.” I went home and told Hillary then she’s like, “Oh yeah. You’ve had it for a long time, I just didn’t want to tell you.” We were joking like you know, that comes from the rapid growth.

Josh Pigford: Right. I mean it’s like they show pictures of like before-and-after of presidents. It’s the same for people who run a business.

Nathan Barry: Yeah. Friends don’t let friends become presidents.

Josh Pigford: Yeah. Exactly. Okay, so the inverse of that, obviously there’s some downsides and struggles as you’re scaling soon that fast, but I mean for you what’s been what are your favorite parts of being able to have this thing that’s taking off?

Nathan Barry: Yeah. I enjoy all the opportunities that come from it, of like actually being able to go to an event and say like … someone’s like, “Oh, what are you doing?” I’m like, “I work at ConvertKit.” They’re like, “Wow. Really? I use ConvertKit.” Like I was at a conference and there was this bus ride back from one of the evening activities. It’s this bus ride at night. It’s dark. I’m sitting next to this guy named Josh we’re talking, and not yet. We were talking for a while, and talking about like places we visited in Thailand while traveling and all the stuff and then like 15 minutes in he’s like, “What do you do?” and I was like, “I work at ConvertKit.” He’s like, “Oh, we’ve used ConvertKit for years.” It was just that fun experience of like, we’re so far into a conversation and I’d actually was really familiar with his blog and all this stuff, and didn’t realize who he was either. But like that kind of thing for me is really fun.

Probably the other thing is we’ve put such an emphasis in being profitable, and then investing not exclusively in things that we think will get us a return, of like, “Hey. We have to grow at this rate so like spend all this money on Facebook ads or whatever,” but instead on like projects that we want to see in the world. We shot this documentary on how bloggers earn a living, and like traveled the 10 different cities and hired a film crew. This whole project I don’t know probably cost like $85,000 and it’s something that we don’t expect to make a return from, but it’s something that we wanted to exist, and we wanted to get out there in the world, and so we get to just spend money on it.

Same thing like we decided to host a conference because as arrogant as we are, we’re like, “We can do better than that bajillion other conferences that are out there.” We ended up creating this amazing experience and it was truthfully like one of the greatest conferences I’ve ever been to, and people were like, “Wow. This is a first year event? Like it’s so polished and the talks are so good,” and like we had Seth Godin keynote the event and we you know … it was this amazing experience and we lost a ton of money on it, but it was like … it was half a month of profit that we lost on this event. It was like, oh like on one hand we only brought in half of the expense … only half of the expense of the event were covered with revenue, and we’re like, “Oh, this is so much money,” but then it was like, “You know what? We get to do these projects because we’ve built a profitable SAS copy.”

Josh Pigford: Stuff like that to some extent is a branding play, right? I mean like you’re making yourself known. But you won’t see the return … you might not see returns on that for months or years, but you probably will see some kind of return on it.

Nathan Barry: Yeah. We tend to not flush money that way.

Josh Pigford: Right.

Nathan Barry: We have some idea of what we’re doing there but-

Josh Pigford: You guys also do … I mean you mentioned spending or investing profits in other things than just like growth. You guys also do profit sharing, right? Or release bonuses that are actually attached to that?

Nathan Barry: Yeah.

Josh Pigford: Tell me about that.

Nathan Barry: We do. We’ve tried it a few different ways but we’ve kind of come to a little bit of a system on it, and that’s, where we do add … at each of our team retreats, so we do two team retreats a year. One in the summer, one in the winter, and you know we just look back at the goals that we’ve hit, what the profitability from the time period is and then pay out a portion of those profits to the team. This last time it was $200,000 or I guess $225,000 split between … we have 28 people now. The average check size was something like $8,000 for the previous six months, so it ended up being pretty significant. We distribute that based on two things. So 25% of it is distributed just based on time with the company. So out of all the days worked at ConvertKit. You’ve been here for you know 400 of them, and so this is like the portion that you get based on that.

Then the other thing is we have this internal kind of rating system, of how we determine performance. The other 75% of your profit sharing bonus is determined based on your performance in the last six months. That’s just a zero to four scale that we tried out, and it seemed to work well, so we’re going to refine it a little bit. But it’s basically like, zero is, “Hey. We should have fired you actually. I don’t know why we haven’t fired you, and so let’s tale care of that now.” We haven’t ever used the zero. A one would be like, “Hey. You’re doing good work and we believe in you, but you’re not hitting your KPIs.” Then a two would be, “You’re hitting … like we set high expectations and you’re hitting your KPIs. You’re doing great work that we expect.” Then three would be, “You’re going above and beyond in some really remarkable way.” Then a four is like going above and beyond at some remarkable way, that like truly move the business forward.

We’ve never given out of four but … so kind of rating people on that, and then you come to like for every one of those performance points that you get it has a dollar amount tied to it. That’s the balance for whoever is doing great work. Then we have another part of the formula to like cut down the amount if just joined. Someone who was only there for like two months of the six month profit-sharing period, you know only gets that smaller percentage. But yeah, it resulted in like people who had just joined getting like $500–800, and then all the way up to the top performers who had been there the longest, who were getting … I think the biggest check was 13 and a half thousand.

Josh Pigford: What was the team’s response to that? Like when you guys started doing the profit sharing.

Nathan Barry: Oh they love it. Especially because the first time we did it, it was an absolute total surprise. We did it at our first team retreat, and this was really fun because we … another thing that we’ve done a couple times, and we don’t do it every time, we try to keep it as a total surprise. We’ve done like the first team retreat it was the first time most people had met each other. Ashley who’s our director of operations, she and I had picked out individual personalized gifts for every person on the team. We’d set kind of a budget of about a 100 bucks per person, and it was just like, “Okay. What do we know about this person? Okay. They like hiking. The outdoors,” you know this kind of stuff, and we try to come up with something that fits them. We’d like stalk their Pinterest pages to see what they’d pinned, to get an idea for the kinds of things they would want.

As a surprise on the first night, we like bring out all these giant boxes and like pass out gifts, and everyone absolutely loves it. Because it’s like the pair of running shoes that someone really, really wanted but hasn’t bought that or … like all the stuff, because we really researched it. People loved it, and the whole group kind of devolved as everyone’s like showing each other what gifts they got, and then one of our team members had … we always do our retreats in like these big houses, and one of our team members had baked a bunch of chocolate chip cookies and so everyone’s like eating dessert, and I’m like, “Hey guys. Okay. We have another thing that we need to do.” We’re like you know like wrangle this chaos back together, and get everyone’s attention again, and then surprised them with the profit-sharing checks. It was like … people loved it, and they still just talk about to this day.

Josh Pigford: How do you I mean you know … I imagine you like sitting or standing or whatever up front and then just like taking it all in. Like all these people you know-

Nathan Barry: Oh yeah. Anyone on my team-

Josh Pigford: That’s a pretty feeling.

Nathan Barry: Oh it is, and anyone on my team will tell you that I cry pretty easily in front of big groups, and so yeah. It was funny. There’s a few other people on the team who like get really surprised. This next time everyone expected profit sharing, we told them, “Hey. This is the formula,” but the checks ended up … even though we’d given them the formula, and even a spreadsheet where you … because we always like people to know … to like feel control over their jobs and their earning and all of that, but I’d put $100,000 in this formula or in the spreadsheet as like the example profit sharing amount, and everyone thought that would be the actual profit sharing amount. Even though they knew they were getting checks and then you know the size still totally surprised them. I have that on video of people like … I’ve got this video of like just one person on the team that is just like so surprised and happy, because the check is about double what she expected. There’s stuff like that’s fun. It’s harder and harder to do surprises, so we mix it up.

One other thing that we did this last time that we’re going to keep doing at more team retreats, or try to come up with other things is … like we’ve done all this to reward the team, and we talked a lot about ConvertKit existing as a company to help like bloggers and creators earn a living from their work, and so that’s why we do the conferences. That’s why we do the documentary and all of that, but then we decided to do something else new and that was … what we did was at the retreat we talked about how, “Okay. All of this is great. That we can help someone like start an audience, and then make their first $10,000 online or their first $1,000 or whatever. But like let’s try to think beyond that to everyone who doesn’t have even those opportunities, and let’s give in to some more basic needs of like clean water, and housing, and education and stuff like that.”

What we did is what we called charity night, and that’s where we took $10,000 and we pre divided everyone up into groups, because at this point the team is 28 people. People don’t spend as much time with each other as you might expect. They tend to spend more time within their teams, and so we divided everyone up based on who we thought didn’t know each other very well, into these groups are four or five people and then said like, “Okay. You have 30 minutes. Go away, and come up with … basically what we’re going to do is we’re going to give away this $10,000 in $100 increments, and you have 30 minutes to figure out which organizations you’re going to give to.” So like each group of four people has to come up with like 16 organizations.

What ended up happening that was super cool is, everyone did that, that was a great experience to have that feeling of giving back, but then also as we came back together, people shared some of their favorite organizations that they gave to and why. What that did is you learned stories about people that you probably never would have heard otherwise. Like the charities that people support ends up being a really personal thing, like a lot of the reasons behind it. You’d find like someone gave to this you know … I’m trying to think like this organization for like Hodgkin’s lymphoma, because one of their parents had died from that. Other people were like, I don’t know, much in the lighter note like oh they really wanted to support this pet rescue organization, or like all these different organizations, and people would share the stories behind the why.

Someone else was like, “I wanted to support this organization that helps underprivileged kids go to college, and helps facilitate that process,” because she was the first in her family to go to college. You learn all these stories that you never would have heard otherwise, and it just brings the team so much closer together. That was one thing that we did this last time that was really, really fun.

Josh Pigford: That’s good stuff. Kind of wrapping all this up, so two more questions. One, what for you has been a key part for of the success for ConvertKit?

Nathan Barry: Oh man. I mean probably the perseverance is a big thing, because like obviously we wouldn’t be here today if I decided to shut it down instead of doubling down. Then that wasn’t even an immediate change, and so … I don’t know. I guess I feel like people are looking so much for like that one weird trick to accelerate growth or something like that, and often you’re just going to have to put in way more time than you think. That’s what I did with the direct sales. It’s not scalable, it’s not … I don’t know. It’s not sexy, but like it seriously works.

Josh Pigford: How do you know when to persevere or like throw in the towel?

Nathan Barry: I mean, if it’s on a project overall I would go back to that, in the show notes we can link to that blog post on when to shut down or double down, because those questions I think actually work pretty well. I’ve heard from a bunch of people that they’ve used that same framework, and it’s helped. Because there’s absolutely times where you should be like, “Look, this isn’t working. I’m not the right person for this. The timing is wrong.” Something like … there’s a lot of projects that should be shut down. It’s definitely not as easy as like you know, “Just stay at it for four years and …”

Josh Pigford: Eventually it’ll turn around.

Nathan Barry: It will all work out.

Josh Pigford: Because I mean I would say the ConvertKit story is extremely a typical where you know something all of a sudden, two years in when things have not been doing much of anything, and then all of a sudden really, really took off. I mean like, I don’t know, I can’t off the top my head think of any other stories like that. It’s pretty rare, but I think like the danger is like, it’s easy to get stuck doing something and holding out hope for way too long. There’s a fine line.

Nathan Barry: Mm-hmm (affirmative). It is. There really is.

Josh Pigford: The last question here, what’s the next year look like for you ConvertKit? Like what’s you know … you’ve had a super busy couple of years here, what’s the next year look like? Is it just a repeat of the past two years, or what sort of on the horizon?

Nathan Barry: Yeah. This year we did something really big, and like reimagine the product from the ground up, and that resulted in us building out these amazing new visual automations. It’s just like … the product is now an absolute joy to use, so we’ve got to finish building out some of that functionality, and rollout to I think like 600 or 700 customers right now, and so we need to get it to the other 14,000 or so. That’s a giant project, but then it’s really like, “Okay. Now that we have this new user experience, and this new functionality, like what does that enable from a growth perspective?” So what new accounts can we get, how can we push things bigger?

We’re like starting to spend more on acquisition, like trying to do these bigger … whether it’s big podcast sponsorships or getting even bigger names using the product, or like just trying to think, “Okay. Like how can we have another inflection point in the growth?” Then with that, we’re really good at like, I think I’d call it like hustle driven growth, and that would be the kind of things I’m talking about. Like the direct sales, or then use direct sales to get a webinar and that drives … like that one webinar drives $1,000 of MOR. You’re like stacking these things on top of each other, and it’s just done through pure hustle, and we’re great at that.

At some point you need better systems to drive growth, of like, “Yeah. We have our Facebook Ads dialed in and our conversion rates, and our content marketing. Oh by the way we get a lot from search,” and all that kind of stuff, and we’ve always been really bad at that kind of thing. Probably the last three, four months have been trying to get a lot more of those systems in place, and analytics, so like now we can finally … like I can point back to any promotion we’ve ever done, and find the exact … the current MOR, the total customers, the total net revenue and the exact churn for each of those promotions exactly. But that took a ton of work to be able to get to that level. Now it’s really like scaling up and sustainable systems for growth in the next couple of years.

Josh Pigford: You’re basically like 15 years later, getting to like realize your love of systems from Wendy’s, and putting it into place in software.

Nathan Barry: That’s right.

Josh Pigford: You’re giving back to like your roots here in fast food.

Nathan Barry: Yes. Exactly. Totally.

Josh Pigford: Well, cool man. Well, that’s all I’ve got. Thanks for hopping on the call, it’s been great catching up, and I appreciate you doing this.

Nathan Barry: Oh yeah. Yeah. Thanks for having me.

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.