Augusto Digital Insights: Founders Series, featuring Joel Ross pt. 1


Joel Ross, co-founder of Augusto, shares the history behind Augusto and the many entrepreneurial efforts he and Brian Anderson have led.

In this episode, Brian Anderson converses with Joel Ross, Augusto Digital’s co-founder and CFO and Integrator. Joel has a 20-year career focused on consulting, computer science, product development, team leadership, and financial management. This is one part of a series focused on the people and relationships that guide Augusto’s vision for the future.

Brian and Joel start by sharing how they met—right out of college at Crowe. They laugh about their first experiences in the development world, writing programs on a TI-85 calculator. The two worked together on several projects at Crowe, before Brian left for Sagestone—and eventually recruited Joel to join him there.

At Sagestone, the two thrived in the more technical business. And that’s when they built their first business together: a March madness tool that eventually morphed into TourneyTopia. This tool has served many large customers, including Microsoft, Time Warner Cable, Aerosmith, and the Tennis Channel.

Over the next several years, the two continued doing development and consulting work by day, and squeezing in various entrepreneurial efforts whenever they had free time. PayIt2 is one lasting product that Brian and Joel created as a way to collect money.

One day, Brian invited Joel and Jim Becher to his cottage on Little Whitefish Lake. He took the guys for a boat ride, dropped the anchor, and wouldn’t let them go back to shore until they formed a deal to start their own company.

As of late 2016, Augusto was formed—with Brian, Marty Balkema, and one or two contractors. By 2018, Joel joined on full-time, and Jim joined in early 2019. From there, Augusto quickly began to grow, adding marketing and sales staff and a real business plan.

Listen to the podcast to discover where Augusto is heading now.

We thank Joel for his time on the Augusto Digital Podcast, as he helped us uncover the beginnings and growth of our company!

To listen to the other podcasts in the Founders Series, follow the links below:

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Brian: This is the Augusto Digital Insights Podcast, and I’m your host, Brian Anderson. Here we talk to industry leaders about how they’re using digital technology to transform their businesses. There’s a lot to cover here, so let’s get started. This episode is part of a series focused on the people behind Augusto. I want to highlight our shared history, which is the foundation of how Augusto has grown and operates. These relationships guide our vision for the future. Joel Ross is a co-founder of Augusto. He has a 20-year career focused on consulting, computer science, product development, team leadership, and financial management. Joel is currently the Augusto CFO and Integrator, a term from the popular EOS methodology. Welcome to the podcast, Joel.

Joel: Thanks, Brian. Thanks for having me. I’m looking forward to this. It should be fun.

Brian: Cool. Well, Joel, you and I have been together for a long time working on different ventures. Probably my longest business partner in my life is you, and known you before we even had kids and first job right out of college and stuff, right?

Joel: Yeah. I think you were the first person at Crowe, when they were interviewing on campus at Michigan State, you were the greeter, basically the person who made sure that everybody was comfortable before they went into the interview. You were the greeter at my interviews there.

Brian: And that was way back when we, when I worked at Crowe Chizek and we were recruiting. We used to do campus recruiting. We’d go to all the different campuses and we’d set up booths and we’d have a whole process for how we’d recruit college talent. And so you were someone we were attracted to and yeah, I vaguely remember that. It’s so funny because I did so many of those, but it goes back to show how far back it was that we actually met. And that was … When did you graduate?

Joel: It was ’99. So spring of ’99 would have been when that was.

Brian: Over 20 years ago, right?

Joel: Yeah.

Brian: Over 20 years ago. So I’m a little curious though, what was the history that led you into computer science and consulting?

Joel: Yeah, that’s a good question. I was thinking about that. I think I started writing my first software program on a TI-85 when I was in high school. That was my first experience writing code. I’m like, “That’s a lot of fun.”

Brian: Hey, that was mine too, by the way. My parents bought me a computer. I remember it plugged into a TV. And we didn’t have a color TV for it, so it plugged into a black and white TV, and I think the computer was actually a color computer.

Joel: The TI-85 is a calculator. So I wrote programs on a calculator.

Brian: I’m thinking of the TI-99. I programmed that TI-85 calculator too. I do remember that being foundational.

Joel: And then I went to college to be an electrical engineer and took a few classes in computer science because those were required, and I think there was a QuickBASIC class that I really liked. And then I got to an electromagnetic fields and waves class and went, “This isn’t for me,” and switched more towards the computer side for the computer engineering degree. So that’s how I got into computer science. And then coming out of college, obviously I interviewed with Crowe, partly because I like what Crowe offered, partly because Crowe was located where my girlfriend at the time lived. So it was a good fit. And then I met you and started at Crowe and I think you were the first project I was on, I was with you there too. So that’s how I got into computer science and the consulting gigs.

Brian: That’s interesting. Yeah. What do you remember about the first project we worked on together?

Joel: C2 Manager. This was way back before Agile had really taken off, and I remember working on a probably like 120 page design document of all the different classes that it was going to be in, in the C2 Manager, which is a way for banks to take online applications way before online applications was really a thing. We were trying to build a little product inside of Crowe.

Brian: Yeah, we were basically trying to build like a little SaaS business. And it actually got off the ground. We sold it to multiple banks and they implemented it and they used it for 15 years, probably. And then Becker, who will be a future interview here on the podcast, he supported it and continued to enhance it after we were gone. And there were banks using it for 15 years. And Crowe I think was selling contracts to run it.

Joel: Yeah. I remember going on several sales calls with you to do that. Sales, at that time, was way out of my interest and my comfort zone. But I remember going on several of those as the techie to sell them on the technology we were using.

Brian: Yeah. So we did that, and then we did other consulting things with Crowe, but we were working in our group that was very entrepreneurial inside of Crowe. I mean, a lot of people there are consultants with an entrepreneurial mindset. We were working for one of them, his name was Kim, and he was a visionary. He could sell anything and he could help people understand big picture stuff, and then he would just sell it and then everyone else had to figure it out.

Joel: That’s right. Yep. That was our job, to distill down what he sold, figure out how to turn that into something so that we could implement it for somebody.

Brian: It was a great experience. Learned tons from him. And then I got burnt out because that world just wasn’t going where I wanted to go with my life and career. And then I went back into the consulting group and then I got this gig at Domino’s, and it was like an opportunity to go work on their point of sale system. And I had done some point of sales system work for McDonald’s in Oak Brook, so I had relevant experience, and they wanted me to handle the payment process. So taking credit cards to the new POS and how did that work all the way back to the payment processor. And that was an interesting domain, but I was traveling over to Ann Arbor from Grand Rapids all the time and living in a corporate apartment with three other guys. And I eventually just said, “This is it. I can’t do it.” And I left for Sagestone. And I left you. And then what happened?

Joel: They put me on that project. I think there was one other person who was there for a couple months, and then they put me on that project and I was doing the same thing you were doing for nine months. And for whatever that worked out, that was while my wife was pregnant with our first kid and I quit as the same type of thing where it was too much travel, too much doing this stuff. I’m like, “I can convince my wife why I’m traveling. I can’t tell the kid, ‘Hey, I’m going to be gone for weeks.'” But I quit that job two weeks before my first daughter was born.

Brian: And that’s when I recruited you to come work at Sagestone, right?

Joel: Yep. So I came over to Sagestone.

Brian: And Sagestone at the time I think it was a .NET Gold partner, like back in the day, earliest days of .NET. I think when I started working with them, .NET was still in beta. And they were already building .NET apps, which I thought was pretty cutting edge. And at that time I was very Microsoft-centric in my skill set, and so that was an interesting opportunity and it was a consulting business, but it was way different than working at Crowe. What do you remember?

Joel: It was way more technical. At Crowe, I don’t want to say I was at the top of the technical heap there, but I was up near the top of technical skills. Crowe was much more business consulting focused, whereas at Sagestone, I wasn’t anywhere near the top of the technical prowess that was there. It was very, very much technical. I learned a lot about how to properly write code and not just solve business problems in the fastest way possible. I learned quite a bit about that.

Brian: Yeah. Yeah. I do remember it being a lot more technical. I really thrived in that for a long time. I enjoyed it. And then that’s when we started our first business together, wasn’t it?

Joel: Yeah. A client came to us in the building. They came to us, what? Like a month or two weeks before March Madness started and said, “Hey, we want to run a March Madness contest.” And you’d done something at Crowe that did most of what they wanted for an internal tool. And then we took that, stood it up for them, made it a little public-facing, added a few…

Brian: What was the tool?

Joel: I don’t even remember what it was called, but it was basically a way for you to take brackets, like take entries for March Madness so you could fill out your brackets online instead of doing it through pieces of paper in a spreadsheet and all that, and it would score everything for you. And I remember afterwards, you’re like, “We should turn this into a business.” And so we started spending nights and weekends and early mornings and just all kinds of time putting into this to just build this thing out.

Brian: Yeah. I think I remember one time coming over to your house and I was writing code and your baby … was it Ally?

Joel: It was Maddie. I think it was.

Brian: Maddie.

Joel: Maddie was on your lap, just all over you.

Brian: She was sitting on my lap. Yeah. I was writing code with your baby on my lap.

Joel: Yeah. I think that might’ve been the last time we did it at my house.

Brian: Okay, so we started working on Tourney Logic, which was actually the bracket control. Remember the web controls and it was like kind of an encapsulation of the bracket concept, which was super highly technical. We way geeked out on that thing. And then we didn’t really sell that, but it turned into Tourneytopia, which was the actual SaaS-focused business that you could do white labeled Bracketology, so March Madness pools. You could set up your own pool and run it. And we learned a ton through that. I remember our first customer was

Joel: You called me at like eight or nine o’clock at night like, “Dude, you have to hear this voicemail.” And they were doing…

Brian: What do you remember about that voicemail?

Joel: They wanted to do a Playmate Pick ‘Em, where you could make picks against playmates and see how you performed against them.

Brian: Oh my gosh. And we ended up implementing that. We had a thing called the tourney pool manager, which was like you could download a web-based application, install it on your intranet. I mean, come on. We were still engineers at that point. But I remember Google was running it internally on their servers for their internal Bracketology contests. Remember that?

Joel: I do. Yep. And it was such a pain to maintain. Probably one of the biggest lessons early on was, “Hey, if we stand this up on our own servers and host it versus making it downloadable, we can update it whenever we want to fix bugs all throughout the tournament without having to publish a new piece of software that people have to go download and install.” So much easier to maintain.

Brian: Yes. And that turned into Tourneytopia, which still is in existence today. And it runs some pretty huge bracket contests for companies that use it for marketing contests. I mean, the tennis channel’s been a customer for over a decade. They run all the major tennis contests through it. And we’ve had Microsoft, Time Warner Cable, we’ve had Aerosmith run a custom bracket on the system. All kinds of stuff. But it was interesting because we were doing that at the same time we were doing consulting work. We were developing code and systems for all kinds of different clients too, right?

Joel: Yeah.

Brian: So we had this going on in nights and weekends and mornings and stuff and whenever it would fit in, and then we had full-time jobs and families too, right?

Joel: Right. Yeah. I still look back and go, “I don’t know how we did that.”

Brian: Yeah. I don’t either.

Joel: Lack of sleep.

Brian: It was good. I just wish that we would have had a little bit more wisdom at that stage to pull ourselves up a little higher. We were still trying to figure out all the code and all the problems in the code and it would’ve been nice if we could’ve thought about it a little bit more business-minded.

Joel: Did zero marketing. I think we ran Google ads one time. We’re like, “Well, we didn’t really do anything. We didn’t know what we were doing. It didn’t work out for us, so let’s never try that again.” We just never really marketed the site.

Brian: Yeah. And yeah, we never did. And really that was a huge takeaway from that. And it still exists and it’s actually produced a pretty decent return for us, but I feel like we could have made it much, much bigger than what it has become if we knew then what we know now. But that learning took us into another business venture together, and I think it was … Sagestone got bought by NuSoft and at that time we were working on a big system for National City Mortgage, and they turned into PNC. They got bought during the financial crisis of 2008. But we had built basically a huge mortgage system that was a virtual loan officer. It even handled HELOC loans, as well as purchase and refi, advanced scenarios with the whole online application integration to a backend CRM system. And I don’t know.

Joel: I remember I got a mortgage during that time and I felt sorry for the mortgage guy, because I knew so much more about how the mortgage process worked than he did. He was trying to tell me stuff, I’m like, “No, I think that’s wrong.”

Brian: Yeah. We had a pricing engine that we developed off of the guidelines from Freddie Mac, I think.

Joel: And what we did there was based off of our learnings from Tourneytopia. I like to tell people that’s one of the most successful projects we’ve ever done and it probably took six months longer than we initially laid out and cost twice as much. And the client was thrilled, because we were constantly getting feedback. I think that’s one of the first consulting projects that I’ve done where we really put it in front of the client all the time and let them see it the whole step of the way. And they were fully defining like, “Oh, okay. Based on this, let’s work on X next instead of what we were going to do.” And we really pushed them to control the software’s destiny. And as a result, they decided they wanted to do way more than they originally thought they did and take a little longer to do it right.

Brian: Yeah. And what’s interesting is, you know who the first customer for Augusto … I’m fast forwarding a little bit. Our first customer was Jeff Lee, who’s now the CEO of a mortgage company, and he was one of our product managers at National City Mortgage.

Joel: Right. Yep. And he’s been a customer of Augusto, or a client of Augusto, for this whole time. Basically every year he’s got work he wants to do with us.

Brian: Yeah. And his business is exploding right now. It’s so fun to watch him and be part of what he’s doing.

Brian: Okay. So, Tourneytopia, we built Tourneytopia, we sold it, we grew it, we learned a ton. And then we both hit the end of the road when NuSoft sold to RCM Technologies, a publicly-traded company, and just didn’t like where the culture was going, didn’t like their vision of where they were going. And so I decided to leave first, and then you decided to leave next.

Joel: Our last day was the same day. I think you gave two weeks, and when I gave my two weeks, they said, “How about one?” And we ended up leaving on the same day.

Brian: Wow. And I don’t think we were really even talking that much about leaving or anything because it was just such a high sensitivity time. There was lots of pressure on all of us and stuff. We were not talking about leaving.

Joel: Yeah. I remember calling you from an airport and talking to you and I’m like, “Hey, I got something I need to tell you.” And you’re like, “Oh, I’ve got something I need to tell you.”

Brian: Yeah. Crazy, right?

Joel: Yep.

Brian: And we knew it was all coming, but we weren’t talking about it. And then we both left. So you went to TrackAbout, and I went to OST. And we can go into that history later, but what did you learn at TrackAbout? Because TrackAbout wasn’t a consulting gig.

Joel: Right. I’ve been in consulting and working on multiple different things, which is kind of why I went into consulting, because I wanted the chance to work on a ton of different things in a bunch of different areas. And I got to a point where I’m like, “I don’t even know if my code is maintainable. The code that I write, I never see it after six months. So let’s see if I can write maintainable code.” And I went to TrackAbout. I actually found that job off of Twitter, from someone I followed on Twitter, and learned a ton of programming skills about test-driven development. And we would very much follow a lot of what we did with National City, where we would put new pieces of functionality, long before it was even ready to be released, in front of our clients to see what they thought of it, adjust it. Building a product versus a piece of software that we just hand off was a big change for me. And so it was fun for 10 years or so to get into that world and learned a ton about how to do product development. And as part of that, I worked up and I managed the development team. So I learned a lot about how to manage a team and that company was … so basically in 2008 is when I started working remotely. So I learned a lot about how to manage remote teams and work with remote teams. I did some remote at NuSoft and RCM at the end, but the team wasn’t remote, I was. I just didn’t want to drive into the office. So that’s a completely different type of culture than a fully remote team. So I learned a lot about that in that time too.

Brian: Yeah. And yeah, we see tons of benefits in having a remote-first culture, which I think spawns out of all that stuff. I remember even the story about traveling to Ann Arbor, we didn’t have an option to work remotely. None of these tools existed. The video technology, the screen sharing, the virtual whiteboards, all that stuff didn’t exist. Slack didn’t exist or Teams or whatever collaboration tools…

Joel: What’s funny is a lot of that stuff did exist. It was just painful. I remember when I started at TrackAbout, the CTO there was like, “Well, I had the option of going through the pain of building a remote team,” because he started in 2000, “or I could move to Pittsburgh.” And he’s like, “I didn’t want to move to Pittsburgh.” So he took the pain of doing that. And it was painful at first. I remember the early days when I was at TrackAbout, we probably went through seven or eight different video softwares of trying to share screens and things like that that would either be really good and then just fall off the market … Microsoft had a great one that they just killed off for no reason, it seemed. Or ones that were just awful, that you’d try. “Yeah, this is really bad and painful.” They were there, they just weren’t nearly as easy as they are now.

Brian: Yeah. Yep. I hear what you’re saying. And I do agree that they existed. I mean, there were chat technologies, there was screen-sharing technology, they just weren’t as integrated. And they weren’t packaged up and thought through the way they are these days. And I think they’re just going to continue to get better. But what’s interesting about that whole journey is, when we split off and went these different ways, we launched another business together.

Joel: Yeah. That was PayItSquare, PayIt2 now.

Brian: Yeah. We were starting to think more like business people instead of engineers, but we were still engineers at heart, but we were seeing business problems now. “Oh, hey look, it’s hard for people to pay each other when they are collecting money for a sports team or they’re going on a trip together or something like that.” So we started with this group payments concept and used our payments knowledge from what we were doing at McDonald’s and Domino’s and stuff, and we built a place where you could create pages and collect money from people. And just you publish a simple page and then you list people that owe you money and they come and pay. And we integrated with PayPal and Square and WePay and there was a whole journey there. And that took years. If I remember correctly, we paid some of our profits for me to go out to San Francisco because we were invited by PayPal to go to their innovation conference. And I think we won our category that year. What do you recall, any of that?

Joel: I remember. So we used the profits from Tourneytopia to pay for you to go out there. And I think we won like a $10,000 prize. And I don’t even remember what it was for, but it was something from PayPal because you went to a PayPal conference. And I remember you calling like, “There’s lots of traction out here. Lots of people are really interested in what we’re doing.” And you won this innovation prize of some sort.

Brian: Yeah, I had known about them and maybe interacted with them through email and then, because I was there, they were down in Palo Alto so I made arrangements to go down and see them in person. And I remember going in their office, and they knew I was coming in so they were kind of hyper-aware of PayPal and they knew I was coming in. A big conference was there. So they actually got this huge ice block made and they put this plaque inside the ice block and it said, “PayPal freezes accounts.” I remember watching because I’m walking through the conference and there’s all these people and this huge ice block and they set it up in front of the conference door. Then they just laughed and they were just cracking up and laughing and stuff. And then there was this whole big thing at the conference because they had done this stunt to put this thing on that said, “PayPal freezes accounts.”

Joel: Yeah, that was big. PayPal used to freeze accounts. If you used anything … We ran into that when we were looking at doing stuff like collecting payments or something like that for Tourneytopia. They would freeze accounts.

Brian: Yeah. So I just remembered. We worked on that for a long time and then we came back and I think we were in those stages still of young families, and so I didn’t really understand the fundraising process that well. And I ended up doing a deal with OST and Dan could see the vision of where we were going. And so he decided to invest and they bought the majority interest to PayItSquare, right?

Joel: Yeah.

Brian: And then we worked on that hard for a while and it ran its course, but at one point I think it was making almost $20,000 a month. So that was a bigger success and it was happening every month, and every day people were paying, we were getting revenue. PayItSquare was like a square peg in a round hole at OST. It just never got what it needed or we didn’t have the knowledge or the time to do what we needed to do on it. And it ultimately has declined, but it’s still in business, still helping people collect money. And if you search for “collect money” on the web, it’s still one of the top search results you’ll get for thousands of collecting money scenarios.

Joel: Right. Yeah. It’s still out there. The long tail of some of these things is interesting, to see how long they last when you’re not really even putting anything into it anymore.

Brian: Hey, Joel, I just want to cut in for a second and bring part one to an end, and we’ll tee up part two, which is coming after the break. And that is to focus on what are the things that we’ve learned from the engineering perspective, the product development perspective, and how do we run products, development projects, and what are we excited about in the future. So talk to you after the break. Hey, thanks for listening to the Augusto Digital Insights Podcast. Augusto is a custom software design and development company. If we can help you on your next project or you just want to say hello, contact me today by calling (616) 427-1914 or visit Remember, you can always find this podcast on iTunes, Spotify, Google, and YouTube.

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