[00:00:27] Jay: Hi everyone. Welcome to The First Customer podcast. My name is Jay Aigner today I'm lucky enough to be joined by Jon Kinney. He's the founding partner, which we just came up with that title and CTO at Headway. Jon, thanks for joining me, buddy. How are you?
[00:00:39] Jon: Yeah, I'm great, Jay. Thanks for having me on the show. Pleasure to be here.
[00:00:42] Jay: so we've had some technical things and some timing things, but we're here. I'm excited to have you on. Tell me about Headway, just so everybody kind of has an off the top understanding what you guys do.
[00:00:54] Jon: Yeah. So Headway is a digital product studio. We are based out of green Bay, Wisconsin, but we have folks all across the U S. So we're remote first company and we build web and mobile applications for entrepreneurs. we've literally helped launch ideas from zero to one off of a napkin. we had a client who was a pastor and a race car driver and wanted to help build an app to help folks.
In their relationships become closer. And so we built that app and launched it to the market. And we've also done zero to one product delivery for larger enterprise style clients as well. bringing new products to market though, is a big part of our specialty through design development and product strategy.
[00:01:34] Jay: Did you just skim through a Christian race car dating app? Is that what you just explained to
[00:01:40] Jon: It, yes, it wasn't necessarily only a Christian dating app. Anybody could, try to better their relationship on this app, but it was founded by a pastor who happens to drive race cars.
[00:01:51] Jay: Wow. All right. Well, that's a good intro. so tell me where did you grow up and did that have an impact on you being an entrepreneur later in life?
[00:01:59] Jon: Absolutely. Yeah. So I grew up in Southwest Wisconsin, originally Madison, the capital city of Wisconsin, and I was involved in a boy choir in hockey, as I grew older, played football and baseball. But I was kind of always on the bridge of, Music and technology and sports. And my dad was a musician growing up.
he did that for 30 or so years and my mom was a graphic designer. And so we had instruments around the house and we had computers around the house. And I always was really interested in creating things and trying to figure out how I could plug stuff in and have fun. And so, over time, as my mom, Founded her own company.
I became more interested in, Hey, what, how can I help? What can I do to be a part of this? Cause it was a pretty fun company. It was called out of the box publishing. And they were a game company that was trying to launch family friendly games that you could play in 30 minutes or less. And their big hit was apples to apples.
So Mattel acquired that, back 2000. Eight or so, I want to say right before everything kind of went south in the economy. So it was a good time to sell and they were able to, exit that. But leading up, I mean, the warehouse was in our garage at our house. And my dad eventually became the warehouse and shipping and logistics manager for the company.
So I had a front row seat to. What it takes to launch from one game to 50 plus and grow that company. And that, that definitely influenced what I wanted to be when I grew up.
[00:03:24] Jay: So many surprises already. Did you tell me that your mom started the company that came up with apples to apples?
[00:03:30] Jon: Yeah. It's a bit of a funny story and it echoes in our line of work at Headway to where they had a game that was out there, they were trying to do this. New venture kind of on the side, right? Bootstrap it. And as things started to gain traction with this publishing company, originally publishing their own games, they started to draw the attention of game inventors and folks who wanted to bring their game to out of the box for publishing.
And. One gentleman came to one of the shows one day, and these were things like Gen Con and the New York Toy Fair and all kinds of places that you would go to play tabletop role playing games or card games, and he'd got a meeting with, With the CEO of the company out of the box and the CEO's name was Mark.
And so Mark and my mom, Kathy were business partners. And so they had this meeting and the gentleman said, Hey, I've got this really great game. I've been spending the last five years developing it. Everyone's going to love it. I promise if you're in software, you've heard this before. If I build it, they will come.
So. Mark got ahold of the demo of this game and he showed it to him. And he's like, yeah, I only want this one thing. There was spinners and cards and dice and like a mousetrap thing and this elaborate setup and Mark at the company was like, I think this part is it like appreciate everything you've done here.
But if we're going to publish this, like we want to kind of pick it apart and take this piece and bring it to market. And. That's what they did. And at the time, Matt Kirby was the inventor of that game, which was not titled Apples to Apples at the time. He was pretty reluctant, you know, there was a vision there and there was a process and they needed to be true to the family friendly games in 30 minutes.
And they helped bring that to market. And it was a big success.
[00:05:15] Jay: That's a really cool story. I mean, it's just like a, we make, we live in the world of digital products and making them. it's always, I always find it interesting when like you get reminded that the rest of the world kind of works the same way, like building stuff, meeting customers, you know, you're, we talk about ICP and all like the very, you know, Tech focus, like, you know, products and stuff we build, but it's cool to hear, like you said, he built it one way.
And I mean, I'm sure you've seen, entrepreneurs that, you know, kind of want to swing for the moon and, you know, think they know what the next big thing is going to be to build. And do you guys have to get in the position where you tell them. This isn't feasible. This is not a great idea. This is like, how do you guys deal with things that people bring to you?
That maybe aren't, don't have enough research to know that they're a good product or you guys just like, you know, kind of build it and let the market decide.
[00:06:05] Jon: It's Transcribed by https: otter. ai Very tricky as a service provider to walk that line. And it's something over the last years, since founding Headway, we've had to grapple with because we want to go and test the market. We want to say, is this idea viable? do you have competition? What are they doing?
What's the price point? What's your target user? how are we going to acquire them? And sometimes they'll let us run with it. And. Validate the market and we'll find that there isn't one right and then what, you know, they just paid however many weeks worth of effort to find out that we think is how kind of folks will frame it.
Oh, well, you didn't find the market, right? It's still there, but you guys didn't do it right or whatever. And then, you know, they'll pick a different team and launch and fail, unfortunately. So we've seen that story happen. the other side of it is you can pivot your idea. So we can find what the market, what you think it is.
And then you talk to customers and they say, well, yeah, but you know, 80 percent or 50%. And. Then we'll build that, but we think the best path forward is to launch the smallest thing you can that still serves your vision and then iterate along the way, but it's difficult sometimes to get people to trust you to, to launch a smaller version than their grandiose vision.
And so, yeah, we don't have a hundred percent answer for that. Other than recently in our, statements of work and things, we came up with this product team model that. It says, here's what you're bringing to the table. Here's what we're bringing to the table. And we highlight certain areas of risk and responsibility.
And one of the things that now we have to say is like, we're assuming that, you know, you've verified the market, you know, we aren't going to reinvent the wheel here. We're going to build essentially what you tell us to. and we'd love to be a part of the entrepreneurial journey. When we can more than that, but we also have to earn a living.
And so when folks want something built their way, you know, we can also do that with the most risk mitigation possible based on our experience by building in the right tools for them to analyze things along the way after launch.
[00:08:13] Jay: By the way, that's a great answer to what I was trying to say. I think is a ridiculous question. I mean, for me to throw that at you, it was a great answer. but you know, it, the apples to apples thing like applies. I mean, you have to have that moment where they're like, this is not exactly what you thought it was going to be.
It could be really popular and great if you trim the fat and like, you know, make it just the cards and not the mousetrap thing. I think it's a great analogy for, you know, a lot of young entrepreneurs. so you grew up in a crazy, having a crazy backstage pass to business and entrepreneurship. what was the first business you started?
[00:08:47] Jon: Oh, the first business I started was selling things on eBay and it's actually how I got into programming as well. So kind of a funny intersection of, talents and interests there too. I really wanted a power book, Pismo G3 back in 2001. And. I had a crappy old 133 megahertz Apple something. And I'm like, I just got to get this thing.
And so I would sell some of the stuff that I had gotten for Christmas or bought over the years. And my parents are like, you're selling all this stuff for like a third of what we paid for it for you. I'm like, I know, but I got to hustle to get this laptop that I need. And my mom's like, all right, well, you know, we'll help support you.
It's fine. You can do it. So. I figured out early on in the days of eBay that the things that sold more effectively had bold text, as simple as that sounds, and italics and larger fonts as the headers and images and things. And so I figured out a way to dress up my listings with HTML. I don't think they had CSS capabilities at that time.
I can't recall exactly how it all played in, but I'm pretty sure I was putting bold tags and italic tags and H one tags and things, you know, you couldn't really style it too much more than that. But that was as simplistic as that sounds today. When we have things like, you know, react and rails and Phoenix and whatnot to build really complex products with learning HTML was still programming for me at the time.
And, yeah, that's how I started to sell. Everything I owned to get something else that I certainly needed.
[00:10:22] Jay: I have to tell you that, in around 2001, that was my first job was this guy would go to the auction houses and buy pallets of random stuff, bring it back. And then he needed a guy to make the ads on eBay for all those things that he bought, and that's what I did. So I was also in 2001, maybe a little bit earlier or later, whatever.
But, Yeah. Building ads in HTML. There was no CSS. it was such a wild west.and it was cool. Like you said, you kind of picked up, you had to do your own research, you know, figure out what these things were, what, how to sell them. Other people were selling them successfully. So, that's a really, that's a cool, first gig.
How long did you do that before you kind of got tired of it or ran out of stuff that your grandma had given you for Christmas?
[00:11:04] Jon: Yeah, I was pretty big into eBay for probably two or three years. and yeah, then after that, I got some more menial jobs like packing boxes at Land's End in Dodgeville, Wisconsin. I don't know if folks are familiar with the Land's End clothing catalog, but they were a great place to work and it was after school hours, they were flexible time and, I learned, you know, I had already had some experience packing games into boxes and things.
And so I figured, Hey, this is. Something I can do. It's independent. My buddy and I would drive there after school, work for six hours or so, drive home and get a couple hundred bucks every few weeks and, learned how to kind of do the real work, right? Pay your dues, like just have an actual job and, progressed from that into.
Actually customer support, like help desk stuff at, at college. So I worked all the way part time through college and I'm not going to say it, I supported myself, you know, my parents helped me out with college, but that was my spending money and that was my kind of fun, opportunities to, you know, buy recording gear or whatever.
and so that was always a big part of Providing for what I wanted is figuring out how to go do something I was good at and be able to then have the flexibility in my life to make that what I wanted it. And I knew that ultimately deep down somewhere. I was going to do that at a larger scale for myself over time.
I just didn't really have necessarily the footing. At the time we graduated, Apples to Apples hadn't sold yet, right? We're still kind of grinding as a family monetarily. My two sisters both needed, you know, to go to college and things. So I didn't have like this. This golden parachute to just start my own company with, you know, a bunch of money from the folks.
So I went to work as a developer, as a programmer and really developed a passion for that. And, eventually, you know, was able to get Headway going, but that's a bit of a longer story.
[00:12:51] Jay: do you think it's possible to be a successful entrepreneur if you had never done the work, if you'd never been packing boxes or doing like some like hands on? And maybe that's equates to digital work today. But do you think it's possible to appreciate that leadership role without having kind of been doing the grind before?
[00:13:15] Jon: I think so, but it would depend on what you're, who you're selling to, right? If you're selling to other folks, maybe that have had a similar life experience and you can relate, you know, I think you could probably find a way to make that work. If you've never held a job like that, but you're trying to come up with an app to optimize the efficiency of the way that folks are packing custom orders from an online catalog, they're probably gonna laugh you out of the room, right?
Or your co founder better have done that. cause you definitely need some on the ground experience to be successful. If you're trying to disrupt the market like that, if you're just trying to do some consultative work, you know, like at Headway, we haven't done the job of everybody we come in to help build something for.
We ask them all the right questions, we shadow and we learn what it takes to actually do that before prescribing the solution.
Makes sense. Okay, so let's jump ahead. very entrepreneurial focused, kinda upbringing. did you carry that? When did you get to kick that off? I mean, past the eBay stuff, past, you know, being a programmer for yourself. how did you start to tie it all together and is that where, how do I kind of kind in Yeah, I wasn't 100 percent sure what I wanted it to look like. My wife and I wanted to start a family, we wanted to buy a house and she was, she's much more conservative financially and risk taking wise than me. And so she wasn't super excited about the notion of, Starting something that, you know, very likely could fail.
And where would that leave us? But I knew that what I did was enough in demand that if we started something and it failed, we could always go get another job. Right. And there's, I gained a lot of value and a lot of worth from the work I did for other folks and from learning from them and seeing what it takes to deliver successful digital products and what it meant to truly go above and beyond for a customer.
And so I, I also felt like I needed to live it. Before I could do it myself. I didn't want to have this, you know, grandiose vision of my capabilities having not been there done that and Over time, having had many different job experiences, it started to feel like, okay, I kind of get this. I kind of understand what it means to deliver digital products.
And I'm finding a few things here and there that I think I could do better than the opportunities that I've had so far. As grateful as I was for those at some point, people get that itch and they want to try and do it on their own. And I was co working with a couple of folks above a wine bar in De Pere, Wisconsin.
We were all working remotely for other companies. And we have this opportunity, this kind of answers your first customer question too. I hope that's okay.
[00:15:54] Jay: Please do. I love it when it ties in with the story.
[00:15:56] Jon: So we were all co working for, together, just paying rent basically for what really should have been a one person office. But we had four of us in there and it was, there was also a haircut place right next door.
So when the AC turned on, the hair would kind of fall from the ceiling, but that's where we started. So we decided. You know, Hey, we've all been doing this development thing, this design thing for a while. Are you kind of feeling the answer? You feel it? You feel it? and there was sort of this idea around Headway coming to be, and I wasn't at the extremely initial vision part of it.
That was more Andrew and Eric, who are my two current business partners, but I got brought in before we really kind of founded things. And I became a part of that founding group, as the discussions matured really. Okay. And. We were in, we decided we were going to do it, but we needed a customer, right? We needed somebody to be able to allow us to go two feet into this thing called Headway and offer our services under the same banner.
And so it took a while, it took a few months, but we finally. I had an opportunity where one of our friends worked at a company out in San Francisco called Handshake and their join handshake. com really successful, huge marketplace for young, college folks to find their first job. And so everybody in the adult working world is on.
LinkedIn to network and find their next thing, but more and more handshake is that first entry point for younger folks looking for their first job and they would facilitate, job fairs ticketing, for those events on campus. And they, their CEO Garrett explained it to us once as. They use the Career Center at the college as this forcing function to have the businesses come to the Career Center, the students come to the Career Center, and Handshake really is the digital tool that the Career Center can now leverage to help connect the right people to the right opportunities.
And so we were approached by a friend of ours who we all knew who worked there and said, It actually individually to us at first, Hey, could your company help? Hey, could your company, Hey, could your company help? And we're like, did he talk to you? Did he tell you, maybe this might be the thing. And so we decided that was going to be a good enough opportunity.
We were able to sell, I think, six months worth of, three or four of us. I forget exactly who all was on that first contract, but enough that we could jump in and make the leap. And we were That's the point at which Headway was born. And we were able to go full time and take that first opportunity on.
And we didn't know who customer number two was going to be. but we were able to figure it out along the way.
[00:18:37] Jay: I mean, that's a great story and that kind of leads to who, how did you figure out who was supposed to be number two at the time? And then how did that evolve to how you identify and go after prospects today?
[00:18:52] Jon: So all of us had experienced the founding team at Headway building and or working for very early stage startups. So Eric and Andrew founded several. I worked as a CTO for a FinTech startup for a number of years in between consulting opportunities that I had. And I was. Employee number one, person number three at that company, there were two co founders and I actually was working for them at one of my, one of my companies at the time called Entritia.
They got acquired by a different group, but eventually they said, Hey, Jon, you've done such an awesome job helping lead this project. The other engineers,have delivered under your guidance. We'd love to bring you on as our CTO. And I said, that's great. We can't do that. cause that's against, you know, the employment contract that I have, but they were able to work it out and I was able to go on and be a CTO for them.
And so having had that sort of, again, zero to one experience building their product at the consultancy that I was at, and then helping mature it through the market to ultimately them leading to an exit as well, I had a, I had that startup experience, Andrew and Eric had it, and we said, why don't we serve startups?
Like nobody's really doing that. Certainly not in Northeast Wisconsin.
[00:20:06] Jay: Right.
[00:20:07] Jon: and so that became our target market. It was folks who needed to bring a brand new idea to market. We tried to build things as scrappy as we could. And. And it worked because several folks started to find out about us. We had,some initiatives in the community to help entrepreneurs find their footing with one another.
We essentially, it was called digital fertilizer and Andrew founded that. And it, it helped people connect and it helped us. Kind of get our name out there as a digital partner to the entrepreneurial community in Northeast Wisconsin. So having established that foothold and having had several successes in that area, we started to be able to reach out beyond Northeast Wisconsin and the one opportunity in California, and kind of bridge those gaps and build a network across the U S.
[00:20:55] Jay: I love that so much, though, because. I have kind of come back to appreciating starting where you're at. Right. There's like, there's definitely a, I keep calling it the hometown discount. Right? Like, like people will at least talk to you because you're from the same place. there's a immediate.
Like when you have compared to going to somebody in New York or in, you know, Atlanta or somebody have nobody, you don't know anybody, you come off as some salesperson from some other place. So, I love that. How long did you guys kind of spend in that hyper focused local kind of marketing targeting until you expanded out?
[00:21:33] Jon: would say, let's see three or four years. We probably three, we had the initial client obviously who was very much not in green Bay. then we were able to start to get more folks that were around the area, but as we would attend events and as we built more of a network across the U S I mean, Software and innovation can happen anywhere.
We had all been working remotely already before Headway. So we knew the tools and techniques to be successful there. Several of our clients needed some convincing that was going to be okay. Cause they were used to being able to go tap their developer on the shoulder in the office. But, early on before zoom was even a thing, we figured out how to do it remotely and we had to train folks and educate them on how to best bring that software to market and collaborate remotely.
But, eventually it allowed us to grow beyond what we were That smaller subset. And so I would say right around 2018, or 2019, we were growing much, very much locally. We got a bigger office in green Bay and that's when we started to take on the bigger things that, that were beyond Northeast Wisconsin, stuff like a brand new innovation project for Procter and Gamble, you know, bringing a new product to market over the course of several years for multiple millions.
That kind of thing.
[00:22:51] Jay: So going to conferences and sponsoring stuff, meeting people and networking in your local area, that's like pretty great, you know, marketing that I think everybody can benefit from. was the tactic you guys used when you made that shift from local to national or whatever you want to call it? Like, how did you get those accounts at these bigger places?
Was it still relationships? Did you go to different conferences that were outside of Wisconsin? Like, how did you start to make those relationships that maybe you Weren't even on your radar, you know, during that first three or four years, cause you guys are trying to get as much business as you can from the people around you, which makes a lot of sense.
[00:23:28] Jon: We, we were lucky in that several of the folks that we were able to connect with early on at Headway went on to connect us to other more notable brands. And so, we have, you know, close personal connections that we've done business with that are, you know, leading up Titletown Tech, which is a partnership between Microsoft and the Green Bay Packers.
You know, they just closed another loud, large round of their fund too. And. We've had folks that we've worked with, that are management partners there. And so those people can really open a lot of doors for you. But to answer your question, it's relationships. Really, we've tried, we've hired, firms to come in and say, wow, here's what's wrong with your copywriting on your website.
Here's what's wrong with your target market. We're going to run these ads here. We're going to do that. And we just expected this huge, you know, influx Of inbound leads and they never came like ever, we've tried everything we can to folks discover us and. it's only very recently starting to work where some of our YouTube content, where we try and help educate not only the entrepreneurial community, but designers and developers design systems specifically are a topic that our design team has really taken the lead on in the market.
And I can't say the name, but a very large auto manufacturer, found us on a YouTube video about design systems and came to us to say, Hey, Help us out with the, with this multi tiered design system that can be a crossing vehicle experience, our website, mobile, all the things. I
[00:24:58] Jay: beautiful. All right. Well, I'm going to have one final question for you. Non business related. if you could do anything on earth and he knew you couldn't fail, what would it be?
[00:25:10] Jon: think I would have to get music to be a bigger part of my daily life. So, I would probably turn my love of kind of recording myself and tinkering around in the studio, which is where I am right now, into a venture that, you know, I could work with other artists. I could produce records. I could mix things.
And like you said, couldn't fail,
[00:25:31] Jay: can't fail, man.
[00:25:33] Jon: that's probably where I'd want to spend my time.
[00:25:34] Jay: I love it. First. I want to be a musician answer for that. I do. I do love that. if people want to find more about you or Headway, where do they go? How do they do that?
[00:25:43] Jon: Yeah. Headway is Headway. io as an input output and pretty universally around the internet. I am Jon D Kinney, J O N D K I N N E Y.
[00:25:55] Jay: Pretty universally. So there's some places that he's not found as that, but we'll save that for another episode. Jon, it's great to meet you, brother. I think, you got a really cool relatable story. So thank you for giving us some of your time today. I'll talk again soon. All right.
[00:26:08] Jon: Yeah. I appreciate it. Jay. Take care.
[00:26:09] Jay: Thanks man. See ya.
[00:26:10] Jon: Bye.