Augusto Digital Insights: Founder Series, featuring Joel Ross pt. 2


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. In part two, we’re going to focus on our learnings as engineers and as product developers and the things that we’re excited about in the future for Augusto. Let’s jump in. Well, let’s talk a little bit about the Augusto story, because that’s all that … Now we’ve made it to Augusto, right?

Joel: Right.

Brian: I worked at OST. I was growing an app dev team there, and doing a lot of business development work for OST. And then I was also head of this pay at square thing that was a product inside of OST. And so I had a lot going on there and I ended up fizzling out there, got fired, which is a different interview, but that is one of the reasons that I started Augusto. It was the best thing that ever happened to me because I realized, “Okay, I have enough knowledge now. I’m an entrepreneur at heart. I need to go do my own thing.” And that’s when I called you and Jim and I invited you up to the cottage, because I had a cottage up on Little Whitefish Lake, North of Grand Rapids, which was a great spot. And we had our boat in the water. I think I took you for a boat ride and I dropped the anchor and wouldn’t let you guys get off. I think that’s how the story goes.

Joel: That’s right. Pretty much you said, “You’re either swimming to shore or we’re leaving this boat with a deal to start a new company.” And you’ve been talking to me about it before and I’d been interested. Like, “Yeah, this is something.” TrackAbout, my time there, I loved what I was doing there, but I was ready to try something new because I wasn’t feeling necessarily as pushed as I’d like to be. Doing something new, that was one of the draws, like I said, of consulting, is doing something new. And so this coming into Augusto, it was completely brand new. Everything. Sometimes I still feel like every day I’m doing something I’ve never done before.

Brian: Yeah.

Joel: That was one of the big appealing things about that. Plus, just getting back to work with you, and Jim, and then eventually Marty, I’ve had this company described to me as, “It feels like it’s four guys who said, ‘if I ever start my own business, this is how I’m going to do it.’” And that’s what we’ve done.

Brian: Right? Yeah. Because it’s based off of so many lessons learned. And seeing so many different scenarios through consulting and through doing it ourselves, that we were able to see above it and say, “If we’re going to do this, how would we want to do it?” And, there’s still tons to learn every day. I actually love to learn. So it’s like, I’m constantly soaking up my knowledge and growing my wisdom every day. And it’s fun. It’s fun. I enjoy the challenge every day.

Joel: Yeah.

Brian: What do you remember about sitting out on the boat? Is there anything that stood out to you in that conversation?

Joel: That was very fuzzy. I remember we were trying to hammer out the deals of ownership, and how’s it going to work, how are we going to get clients, who’s going to do what? And we worked through some of that stuff. And then we talked a little bit about what type of projects we wanted to do. How do we want to do this? And I think that’s kind of where we discussed some of the, like let’s use contractors, and full-time employees, and a mixture of those things, and what types of roles we would take. I think that’s probably where I got stuck in the CFO role.

Brian: How did you become the CFO of Augusto? Because, you’re coming from an engineering background. How did you become the CFO?

Joel: I think it is the default. I always describe it as they say, “Who wants to be CFO?” And everybody else stepped back and I wasn’t paying attention.

Brian: That’s not it.

Joel: I guess I’d done the finances for Tourneytopia and then Pay It 2 early in those days. So I had a little bit, but not nearly the experiences I’ve got now that I’ve been doing it for Augusto. It just sort of defaulted to me, I’m probably the most, of the original founders, I’m probably the most detail oriented person. That’s sort of important when you’re talking about numbers. I think that’s probably how.

Brian: Yeah, I saw it in you. Because, you were handling all the … I always saw details in you and you always could do analysis work really, really well. And I remember sitting at the patio table looking over the lake and I was like, “Joel, listen, I’ve already thought all of this through. I think that you’ve got to be our initial CFO. You’ve got to manage all the books, and the accounting, and finance stuff because you’re so detailed oriented.” You’ve got to grow because you weren’t trained in any of these things. You have to train yourself. And you had learned a lot through your experiences working with accountants and stuff through these business ventures we did. And legal stuff, you were in a good position, I think, to understand all that stuff. But you were still an engineer at heart and probably still are. Right?

Joel: Yeah.

Brian: Although, it’s probably changing some days with how much work you’re doing in the finance world these days.

Joel: Yes. I definitely spend more time in spreadsheets than in inner IDE.

Brian: Yeah. Yep. Let’s tell a little bit of the Augusto story. So Augusto has grown fairly significantly over the last four years. From day one we’ve been growing, right?

Joel: Yeah. So day one was what? You and Marty full-time and one or two contractors to help with some of the development that was late 2016.

Brian: Todd Portiere was our first contractor.

Joel: He was, we always say, he’s been a contractor before Augusto was Augusto.

Brian: Yep. And Todd and Marty go way back.

Joel: Yep.

Brian: And Todd’s awesome. We love working with Todd. It was me, and Marty, and Todd, and a couple of others. And then we did a deal with Brightly. We thought that they could help accelerate our go to market, which they did, but it … We made smart decisions there, because both sides went in eyes wide open, knowing that this might not be like a marriage made in heaven, but we helped each other progress our businesses. And then we split. But that took like a year and a half, and it did help us get traction, but it slowed our development of our own brand, and thinking positioning, and stuff like that

Joel: Right. I think we made that official, still a good relationship there, but that split of “Let’s become Augusto” in early 2018, is when we started doing some of that stuff.

Brian: Yeah.

Joel: And then mid 2018, we’d grown a little bit. We kind of established ourself. We were still working with Brightly on a few things, and that’s when I made the jump to become full-time. September 1st, 2018 is when I started full-time at, at Augusto. And I think by then, we’d grown to probably 10 to 15 contractors at that time. The full-time employees of Augusto were still just the three of us. We were waiting for Jim to be ready, which I think happened in early 2019.

Brian: It’s crazy. It’s happened so fast, but it seems like so long ago.

Joel: Yeah. Yep. And it’s hard to believe that I’ve been doing this full-time for two years now.

Brian: Yeah, and the transformation of our business in that time and the volume of work we handle these days is just exponential it feels like, compared to where we were at.

Joel: Yeah. So I think we’ll end 2020, we’ve got nine full-time employees, and I think we’ve used 30 contractors throughout this year.

Brian: Yeah. Yeah. That’s interesting. It’s pretty good. And I think it’s going to continue to grow. It’s been interesting. Let’s tell a few more of the entrepreneurial stories of Augusto. Then we can go into some of these other topics. Having Augusto, a growing services consulting business wasn’t enough, so we had to split it into multiple other businesses. So we started with one, did we start with CrewPay first?

Joel: I’m trying to remember if CrewPay or Loft. I think Loft came first.

Brian: Loft came first. So through relationships, through Marty’s relationships, he had a group of entrepreneurs down in the North Carolina, Greensboro area that we’re good friends with. T hey had some interest in starting some … They wanted to try a SaaS business and they also had an idea for really, a name, Loft, and they turned it into a business concept that was around application support. And then that vision, those two companies, Marty and David talked a lot about and they were really hot about doing these things, so we came along and we became partners with them and helped them accelerate these ideas. What’s your recollection of that stuff and what’s some of the background of Crew Pay and Loft?

Joel: Yeah. Loft really came to … I recognize this when I was at TrackAbout, there’s a difference in developers. I see there’s two different types of developers that I call them makers and menders. Makers are the type that you put them in front of a blank ID and they’re thrilled, right? Give them a blank canvas and they will go to town and build you whatever you want. Whereas, a mender is somebody who, they get lost. They don’t know what to do with the blank. But, give them a problem, say, “Hey, this is what’s wrong. And here’s the full stack of any place that it could be.” And they will dig in and find the issue. And Augusto is definitely makers. We start fresh, we build something. And makers don’t tend to want to maintain it once it’s done,.they’ll keep adding new features, but they’re not going to be the people who maintain it.

Joel: So Loft is much more of the menders of the people who will go in and fix issues, and support it, optimize the application to make them run smoothly. And we quickly recognize that those are two different types of people. And so Loft sort of formed off of, let’s find menders that can support these applications. And then CrewPay, it was the same group of people, but a completely different reason for it to exist. And that was, we needed to pay our contractors. That was something that I’d struggled with from day one, is finding a good tool to pay our contractors. Because they weren’t on payroll so it wasn’t quite the same. There weren’t a lot of great tools out there at the time. And we found one,, and they were bought by Stripe and then shut down. And so we sort of came together like, well, there’s three or four different companies that are all paying contractors, our tool that we’ve all been using just shut down, or it’s going to shut down soon, so let’s build something to replace it and do it ourselves. That’s kind of where CrewPay came from.

Brian: Right. That one was coming at it a little bit … There was a business problem there, but it wasn’t … Those a lot of lessons learned, some repeat lessons learned in CrewPay, which were good reinforcements of stuff that we may not do again in the future. But we learned a lot. Through that group, we raised some money from a new fund out of North Carolina that’s part of their economic development programs down there, and learned a lot about working with investors through that process, and the legalities and all the deals and stuff, how they come together. And then Loft is still growing. Still in existence. Augusto hires Loft or refers customers to Loft sometimes. And then Augusto also has learned some lessons from Loft. I mean, we were definitely working more on some managed service concepts,and support concepts and trying to level up that difference between maker and menders and support kind of personalities or system administrators. We’re trying to create a holistic offering that can cover the wide gamut of things that you need in IT and for digital product development. I’ve always said in the beginning, we want Augusto to be the team that we hired to build our digital products. Right?

Joel: Yep.

Brian: Tons of lessons learned there, going through that. And then we did another one, we were in another one called Digital Growth Partners, and that one was all about growth. It was trying to figure out how to use growth marketing and growth hacking. It’s continuous. That’s going on, we’ve done a ton of more work around how to raise funds for clients and all these different things that are leading us into conversations with Michigan State, and The Right Place, and the state, and the city. And then also some other investors and then learning how to potentially raise a fund. And it’s like learning accelerated. Right?

Joel: Right, yep. Again, doing all types of things that we’ve just never done before.

Brian: Yeah. And then at the same time, Augusto continues to grow. We built out a pretty amazing team. All this stuff has happened on top of Augusto, but it also is feeding back into the growth of where we’re going with the Augusto digital business model.

Joel: Right. Yep. All these businesses that we’re working to help get funds through DGP, they’re using them to work with our partner companies, like do their development through Augusto, and all those types of things.

Brian: Yeah. And also it’s given us a better perspective and bigger knowledge base to understand how to grow the business, and what do we really need, and what do people need when they hire us for things? It’s just been a great journey, man. And it’s been fun to like, be on it with you for this long and how much it’s changed and evolved, but it’s still really going. It seems to me like we’re still going in the direction of having a portfolio of digital products and having businesses that support that for our clients and for ourselves.

Joel: Yeah.

Brian: What do you think some of the lessons learned are, coming from an engineer’s perspective? Joel: Yeah. I’ll say one of the biggest lessons is the way we do our projects. I’ll describe, I remember a specific project early where we built something. Like I said, we had these huge, technical documents that described everything. We built it exactly to spec. It took us six months to build it. We delivered it, the customer, the client that we were building it for was super happy when we delivered it. And I remember talking to somebody who was still on the project six months later, “Hey, how’d that work out? How’s that being used?” Like, “Oh yeah, they never released it once they talked to some of the users, it wasn’t what they wanted. So they didn’t use it.” At that time, my thought process was, “Man, they really screwed up. How could they not use something?” And it took me a long time to realize that, it’s not just them that screwed up. We screwed up because we didn’t put it in front of users. We didn’t insist that they look at the progress the whole way through, make sure it’s exactly what they wanted, start using it early. And I think at Augusto, we do that … We try to release early, release often. Every single thing we do, we’re putting it in front of the client. We push the client to make sure that they’re putting it in front of their users who are going to use it, to make sure we’re building the right thing. Because, we don’t want to … As I get older and I value my time more, I don’t want to spend too much time building something that nobody is going to use if that’s a waste of my time. Yeah, I may still get paid and we may still get paid for that. But it’s a drain to know that something you’ve been working on for so long, just isn’t going to be used and it’s a waste of your time. Getting it out in front of them and making sure that it’s what they use, and a lot of times that’s … When we do projects, we don’t necessarily tie the customer to scope and then go, “Oh, do you want to change your scope? You need to do change requests.” We lay out, “Here’s a general idea of what we want to do, but you’re going to direct us through this project to get exactly what you want.”

Brian: Yeah.

Joel: And to me, that’s probably one of the biggest lessons of the way that I think we do software differently than a lot of other companies is through that process.

Brian: Yeah. I think that a lot of times you think of that person as your product owner or your product manager, it’s the person that hired you. But the reality is, they definitely have a big voice in it, but their job should be to be getting information from the customer, the ultimate user, and even bringing those users to the table, to use the system in the earliest stages of development.

Joel: Right. Before development, when you’ve got wireframes. To say, “Hey, would this even be, or you got user experience, is this what’s going to be working for you? Because the earlier on in the process that you make changes, the cheaper it is.”

Brian: Yeah, yeah. And the more dialed in it is when it gets launched, and then the better feedback you get, so you can just keep iterating on it. Because, software is never really done. It can always be improved. It’s just a cost benefit analysis most times. If you want to reduce your costs, you should talk to your users more because it’ll reduce your costs and it’ll create more revenue for you.

Joel: Right. I think a lot of people look at … If I talk to my users, they’re going to give me tons of feedback and I’m going to have a ton of stuff to do. But the reason they’re giving that feedback is because they want it to work a different way. And so you don’t take that. Yeah, it might cost more upfront to do some of this stuff, but the long-term benefits of more users that are using the software the way they want to, you’re going to get a higher revenue.

Brian: Yes. Agreed. Hey, what are the lessons learned coming at this Augusto thing as a product developer, as a business owner?

Joel: Yeah. I think it’s sort of similar, right? You need to make sure that you’re building something that people want. If you’re going to work with us, make sure that we’re building what you want. Don’t let a project go on, steer the ship. Make sure we’re doing what you want us to do and you’re getting what you want out of it. When we build our products, don’t gold plate it. Build just the piece that you need to make it functional, get it out there, and then give people using it, get feedback, and then enhance it over time.

Brian: Yeah. We’ve really oriented our processes to facilitate that. The roles, the way we assign people to teams, it’s really led by an engagement lead, and a technical lead, and the client who’s our product manager. We really try to status like crazy and demo like crazy. A really rhythmic process to try to facilitate what you just described.

Joel: Yep. Yeah. And I think we expect that our clients are going to be involved. That product owner is going to be dedicated to work on this project and review it fairly regularly. It’s not full-time dedication, but it’s going to take some time. It’s not a, “Hey, I threw over some specs and six months later, I’m going to come back and have a finished product.”

Brian: Yeah. Yeah, totally. And we love people who want to go through that journey with us. It’s fun to be … It’s the people that try to throw the ideas off the wall and they get too busy in their day job where it’s more of a struggle. Whereas, the people that just weave it into their life and it’s part of what they’re developing along with the work that they’re doing, those are the people that are the longest standing clients and their businesses are growing like crazy, because they’re optimizing all of these processes for either revenue creation or cost reduction. And time reduction of tasks.

Brian: Okay. Well, hey man, I got two more questions for you. The first one is, how many businesses do we own together? Do you even know?

Joel: I think at one point I added up, and we have nine different LLCs.

Brian: That’s a lot. I guess the last one is, what are you excited about? You’re on the leadership team, you’re seeing vision, and seeing all the numbers add up, and seeing what’s going on in sales, what excites you about what’s going on at Augusto?

Joel: Yeah. I think that the main thing that excites me is I love being able to create jobs. Whether it’s bringing in new contractors or hiring new people, but just that feeling of, there’s 20 people right now that are working because of the stuff that we’ve been doing. And I look forward to a day when I can say, there are a hundred people that are working right now because of what we’re doing, or there’s 500. I think you had one point laid out a big, hairy, audacious goal of a thousand jobs that we would create from Augusto, whether that’s in Augusto, or at our clients, or however that comes to be, but a thousand jobs that are a result of the work we’re doing. And that’s what to me is motivational to keep going. Because there’s obviously things that I don’t like doing sometimes, but having that goal out there and knowing that that’s happening, keeps you going.

Brian: Yeah, purpose, man. It’s hard to find, but when you do find it, it kind of sets everything else up. It gives you reason to work and make work not as hard. Make it something you actually wake up in the morning and enjoy doing. I tell you what, I wake up in the morning every morning and I’m looking forward to the day, most days. And I like being on the journey with people I care about. And I like working with really smart people. I love having really smart, aspirational people to work with.

Joel: Yes. It definitely makes the day easier when everybody you’re talking to is highly motivated, and at the same level, and higher than you. Pulls you up and makes you want to be better.

Brian: Yeah. Hey, one of the things that we talked about recently was this EOS process we’ve been implementing. And I said, I’m not crazy about the fact that a process or we follow a process, and stuff like that, but I really do feel like we just, through that process of discovering a process to use, to organize our business, it really has framed a lot of things for us and frame people’s roles. And it’s created some amazing outcomes that I feel like. What do you think of that?

Joel: Yeah. I think the process is good. It’s given us a lot of structure, like you said, it’s defined roles for different people, and what they need to be doing, and give them a framework of where they can stretch. I would say, as a company, we don’t dictate how things are done. We stress, “here’s the outcome.” We’re definitely a value based. I don’t expect butts in seats from eight to five.

We are more like, “What is the value that you’ve produced? And is that what we want?” And we define, “This is what we want you to do, but within that, we want you to define it.” And I think EOS has given us a structure around to say, “This is your domain. As whatever spot you are in the accountability chart, this is your domain. These are your responsibilities. And you do it that way.”

And it’s really given a structure for meetings too.

Brian: I feel like that’s huge. The different meeting templates have been super helpful. And they were tough to get into those rhythms, but now that we’re in them, they’re so natural. And they’re so much better, I feel like.

Joel: Right. And a lot of that is just … The beginning of a lot of the meetings are like, “Let’s get a pulse on either the business as a whole, or this particular operation. What is the pulse? What is the scorecard essentially that tells us, are we in the right frame of mind?” That then sets the tone for the rest of the meeting, as you say, “Hey, we’re on the right track. We don’t have hard issues to solve this week or this particular thing is off, so let’s do something about that.” It really does help frame some of that.

Brian: Yeah. And then what’s your perspective on the things that are happening around sales and marketing? Because that’s been a lot of learning and journey there to get even where we’re at. And I do believe there’s a big future ahead of us there, but what’s been your perspective from your seat?

Joel: It’s been exciting to watch. We’ve got our first sales person, full-time sales person in the role. We’re finally getting to a point. Our goal was always, Hey … We need to get to a point where we’re getting sales that are coming from the founding team. And we’re finally, we’re getting to that point this year. And it’s exciting to see. All along, like up until recently, I’ve sort of been of the mind, “Well sales and marketing isn’t really my responsibility. I’m no good at it, so I’m going to ignore it.” But this year I’ve gotten a lot more involved and it’s good to see the work that Michael has been doing with the team, and organizing team, and the positioning that we’ve done. It’s been a lot of hard work and a struggle to get here, but I’m really excited to see where we’re going, because I’m starting to see all the pieces start to fall in place.

Brian: Yeah. Yeah, I’m really excited about that to you, man. I’m really thankful for the people that we have on that side of our business. It’s been interesting though, because it’s so much bigger than I realized. I feel like all of these domains, if you go into sales and marketing, or you go into operations and engineering, or you go into finance and administration, it’s so much bigger than you realize. So many specialties.

Joel: Right. There’s always more depth to it. Yeah. I still remember, and I’m going to pick on you a little bit here, I still remember way back in the crow days, you’re like “Let’s make a change. It’s just a small change in the database. It’s a five second change.” That was like your favorite line, “it’s a five second change.” And then two days later we were done with it. I feel like a lot of these things are like that. From the outside, it feels like it’s just a little, little thing you have to take care of. You just have to enter some numbers into QuickBooks and you’ll be done, but it’s a lot bigger than that when you start to peel away the layers of the onion.

Brian: And just the thinking and the concepts that grow out of all that foundational stuff, it’s just vast. I just look at sales and marketing, it always seemed like, “Oh, well we just need a sales and marketing person.” Well, the reality is now we have a sales and marketing director, and we have a business development director, and we have business development reps, and we have a marketing coordinator, and we have marketing specialties like design, and copywriting, and digital, and it just goes on and on. Then we have strategic partnerships and Jim’s been taken on that role and got us to our first … We’re now an AWS Select Partner, which took a lot of work. But also a lot of learning, and I think there’s a big future there for us. It’s just fun, man. I love being on the journey with this team, and I really am enjoying it. Enjoying growing with you all these years and watching both of us grow has been really rewarding in my life. So, I just wanted to say thanks.

Joel: Thank you. I appreciate you bringing me along with you. It’s been a great time. It’s hard to imagine going back and working for someone else at this point.

Brian: Yeah, I agree, man. I feel like we’re on this path for life.

Joel: Yep.

Brian: Well, Joel, thanks very much for being on the Augusto Digital Insights show and I look forward to working with you for many years in the future.

Joel: Thanks for having me, it was a lot of fun.

Brian: 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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