The Ten-Year Journey: an Interview with Omowale Casselle, CEO and Founder of Digital Adventures

Omowale Casselle, Founder and CEO of Digital Adventures

Omowale Casselle is the Founder and CEO of Digital Adventures and before starting his company he was the founder and director of SAMPLEit, a subsidiary of Redbox, and a product leader at Ford Motor Company. Omowale shares his experience in building companies and teams for the long-haul, how he makes his core values and company vision real for his employees, and more on this episode of The Best Team Wins Podcast.


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Adam Robinson: Welcome to The Best Team Wins Podcast, where we feature entrepreneurs whose exceptional approach to the people side of their business has led to incredible results. My name is Adam Robinson, and for the next 25 minutes I’ll be your host as we explore how to build your business through better hiring. Today on the show, Omowale Casselle is the co-founder of Digital Adventures, with locations in Willamette, Illinois and the Lincoln Park neighborhood of Chicago, with big plans to expand to additional locations. Digital Adventures was founded in 2015 and is a profitable bootstrap business.


Prior to Digital Adventures, Omowale was building and managing teams as co-founder and director of SAMPLEit, a subsidiary of Redbox. Omowale, we are so happy to have you on the program today.


Omowale Casselle: It’s good to be here, Adam. Thanks for having me on.


Adam Robinson: We’re here to talk about the people side of your business, but before we do that, let’s set the stage. Give us 30 seconds on Digital Adventures.


Omowale Casselle: Sure. Sure. Digital Adventures, essentially we’re an early stage education technology company that’s focused on unlocking the creative problem solver within kids through a series of coding classes and tech camps. We’ve got state of the art learning studios where we prioritize learning by doing. We’ve got a great group of instructors that teaches kids how to construct robots, model structures in 3D, build mobile applications and websites, create virtual reality worlds, design video games, [inaudible 00:01:39], and make movies. Essentially, how do we get the next generation of kids to have the skills they need to make an impact in our digitally-driven world?


Adam Robinson: Very cool. If listeners want to learn more, what’s the best way they can do that?


Omowale Casselle: Well, the easiest thing would be they can either come by and visit us at one of our learning studios. We’ve got one, like you mentioned, in Lincoln Park, at 701 West Armitage. We’ve also got one up on the North Shore, at 406 Linden Avenue in Willamette. They can also check us out online at, or they can take a look at our reviews on either Facebook or Yelp.


Adam Robinson: Okay. Let’s talk about the people side of Digital Adventures. You’ve got a couple of locations now. I can imagine your experience working for a fast-growing subsidiary of Redbox, that’s the DVD kiosks, informed your approach to team building. When you started the business, philosophically, what did you expect as far as building the early organization, based on what you had done previously?


Omowale Casselle: Well, I think I’ve been very fortunate in my career that I got some early experiences hiring both at Ford and Redbox, so going out on my own and being separate from a larger corporate entity, I think that’s something that I was really interested in kind of understanding or hiring for, is people who could be creative about developing solutions from the ground up without a ton of guidance or understanding on what the entire box, or what the endpoint looked like. Something that we tried to really get to is that, “Is there creativity when someone is developing a solution?” And, “Do they have any experience in maybe jumping into a more ambiguous situation?” Those are some of the things that we initially thought through when we tried to identify that first few employees.


Adam Robinson: Tell us the story. How did you hire your first full-time official employee?


Omowale Casselle: Essentially, we opened our first studio in April of ’15, and so we actually incorporated the company in July of 2014. Between that period in July and starting the first studio in the spring of ’15, we basically had to find someone who understood education, understood technology, understood kids, and so what we did is we looked out at a lot of different things. We did a lot of searches on several social media sites. LinkedIn, and some job boards and things like that. What we were really looking for is someone who had done it before, but hadn’t been so far along the path where they felt like they knew it all or they felt like they really couldn’t do anything additional.


The first one we found was a fellow named Jim, who had worked at another camp, a coding camp that was primarily delivered their programming during the summer. What he really demonstrated to us is that he could take kind of the loose idea, he bought into the vision of what we were trying to do, and we just had him essentially develop a series of lessons that said, “Hey, we’re trying to teach kids how to code. We want it to be fun. We want it to be educational. We want to make sure they enjoy it. Take those kind of very loose and vague guideposts, and develop a couple lessons based on how you think we would accomplish that.” We were just blown away by the quality of the lessons that he developed, and then I did some beta testing on my kids with him. Had him kind of go through and take them through it, and they just loved it. We were very, very fortunate to find Jim, and he’s still with us today, leading the North Shore studio.


Adam Robinson: Oh, that’s fantastic. What’s it like getting the kids involved in testing the product? In a way, they’re part-time QA testers for you. How does that work?


Omowale Casselle: I think it’s really cool. I mean, they’re kind of one of the big reasons why Digital Adventures was started. I studied engineering at the undergraduate and graduate level, and what I was finding is that my kids, as they were coming home, they were getting iPads from schools. They were playing on mommy and daddy’s iPhone at home, but what I was just struggling with is it didn’t feel like they really knew the background, or had an understanding of how you actually build stuff using technology.


The very, very first lesson was actually done by me at the dining room table toward the holiday period in 2014, where I just took them through something really basic to see how they might take to it, and as it’s continued to evolve and grow, Digital Adventures is one of the favorite places that the kids like to go, either for classes or camps. It’s kind of cool. Based on the evolution, we’ve hired additional instructors. Since then, we’ve brought on new platforms, whether it be robotics or virtual reality headsets, and just seeing how they are able to take through things that I think that at older ages, and people who are a little more set in their ways, might struggle with. They’re able to pick things up so quickly, and that’s something that makes me very, very proud as a company owner.


Adam Robinson: Yeah. I can imagine. Talk about your leadership team. Who’s around the table with you as you grow and scale the business?


Omowale Casselle: Yeah. Essentially it’s two folks. It’s Jim, like I mentioned. He’s in charge of the curriculum and instruction, and then my other partner is Arjun, who really heads up the technology and the product portion of things. What he does is, basically Arjun tries to make things that are a lot easier online. One of the guideposts that we have is that as a company that’s focused on technology, and specifically the education of technology, we want to make sure that our website actually looks like people who know what they’re doing from a coding standpoint. I give him a very hard time in terms of the feature set and the functionality of the website, and then the backend processes that really make things more sticky for our customer base.


It’s been a great, great mix of folks. From my side, I focus more on the business aspects of things. We’ve got Arjun focused on the technology and product, and then Jim focused on the curriculum and instruction. With those three, kind of that trifecta, or the Three Stooges, whatever you want to call us, I think that we’ve been able to make some great, great progress in trying to develop a great solution for the marketplace, for both the parents and the students.


Adam Robinson: Sounds like the team is really working well together, and I’m sure that has everything to do with the success that you’ve had. What quality do you think is the most important quality when a founder is looking for a leader? Where a founder is looking to bring someone on to help lead the organization? Both from your experience at Digital Adventures, as well as prior experience. What’s the one most important thing you would say you look for?


Omowale Casselle: I’d say probably the thing I try to understand or dive into most is empathy. I think that when you’re developing a solution, whether it be at Ford Motor Company or at Redbox, or now at Digital Adventures, you really have to be able to understand customers at a deep level, and then use that knowledge and insight to develop a solution that exceeds their expectations. What I really try to get at during the interview process, or during the discussions that we have when we’re discussing bringing on new team members is, “How good are they at understanding others? How good are they at understanding someone else’s perspective?” Because it’s very easy to say, “Oh, I know how I think about things, and I know how I would approach it.” But can you take on how someone else thinks about it? Then can you kind of massage that and develop that into a solution that the customer is going to be very, very excited about? I’d say empathy is number one in my mind.


Adam Robinson: Is there a particular approach you take to ensuring your screening for empathy in the hiring process?


Omowale Casselle: Yeah. I think it’s a lot that goes into the questions, right? There are things that you can dive into when you’re having discussions around people’s resumes, and kind of their stories. One of the things that I like to focus in on from an empathy perspective is that if someone’s ever failed at something in their career, whether it be a startup that went south, or maybe they didn’t accomplish as much as they thought they were going to accomplish at a larger corporation, what I really try to get into is, “Yes, failure. Sometimes that’s unavoidable, but what did you actually learn from it? What are the things that you were able to take away?” Because that to me suggests that you’re able to kind of get outside of yourself and find something that was at a level that maybe you didn’t understand when you were going through it in the trenches, but now that you’ve come out on the other side, you’re able to say, “Hey, you know what? We didn’t quite get that right, and here’s what I would have done differently.”


That’s something that I really try to get to is, A, “Did you understand the problem, or did you understand where you fell short?” And then, “What would you have done differently? And tell me why you think that would have led to a different outcome.”


Adam Robinson: Learning from prior mistakes is, you think, something … At least for your hiring process, failures in the past are desirable experiences for folks to have in your estimation, if they’ve learned from them.


Omowale Casselle: Absolutely. I think success is one of the poorest teachers out there, right? If you’ve gone through … There can be so many things that could be reasons why people have been successful, right? If someone happened to join the right company at the right time, or if someone had a great manager that happened to find favor with them. There’s so many reasons why you could have been successful that was outside of your control. Similarly, not to say that failure is always the ultimate responsibility. I think moreso it’s, “Do you actually understand that whole situation and all those externalities that were included?” And then, “What would you have done differently?”


I think that that’s the key to it, because I think that failure is somewhat unavoidable, but within that process, if you can kind of get a good sense of what went on and what you would do differently, I think that those are people that are showing a level of intellectual maturity and empathy that I think is very valuable, given the rollercoaster ride of most startups.


Adam Robinson: Let’s talk, then, about how you provide coaching and critical feedback to the people in your organization. When someone’s not getting the job done to expectation, or perhaps they’ve missed the mark due to a misunderstanding, how do you approach those situations?


Omowale Casselle: I think the first thing is that philosophically, we have in our mind that if someone’s not meeting expectations, and it initially goes back to the leadership team, right? My thought is that whatever you thought was true about someone in the interview, and in that overall hiring process, is still true. What did you initially do to maybe not onboard correctly, or was there some misunderstanding of expectations? Or things like that. Once we’ve taken that internal hard look at ourselves and really understood if there was some deficiency that we might have enabled or allowed for that poor performance, then I think it’s being very honest and direct to say, “Hey, you know what? These are certain expectations that we have around performance. You’re currently not meeting them. Here’s a couple suggestions that we would love you to take on.” Right?


Because when you think about our environment, we basically function on a monthly subscription, so people come to classes or they come to camps, and if they’re not happy, they can basically stop in a subsequent month. Without the retention and the growing of the customer base by keeping the customers happy, that’s something that can be very, very harmful to the business. What we’ll usually do is we’ll give people the opportunity to listen to that coaching, listen to that feedback, and then see if they improve upon it, and then if there’s continued degradation or lack of improvement, at that point you make that difficult decision to say, “We can’t move forward with you.” Those are some of the hardest things that you can ever make as a leadership team or as a company overall, is to say, “Hey, you know what? This just isn’t going to work out. The fit’s not quite there.” We don’t take those decisions lightly. Like I said, we try to start with, “Is there something that we did wrong?” And then we try to provide that coaching and feedback, and still if that gap continues to be maintained, then we end up parting ways.


Adam Robinson: Other side of the coin, then. How do you reward folks for great performance?


Omowale Casselle: I think that there’s many things, right? The team is, overall, they’re incentivized primarily through both a base, a bonus, and an equity component for their compensation, so in the short-term, there’s the base, which kind of pays the bills, keeps the light on. Then there’s bonuses that are associated with how the company grows and how the company performs from a monthly active user standpoint. It’s something that’s very important to us, is, “How many kids are coming to the studio on a monthly basis? How many kids are being retained?” And then kind of the longer pull is the equity piece of the thing, right? What I’ve told people is that we’re going to go on a 10-year journey here. “If you give me 10 years, I promise you that we’re going to build something pretty meaningful by the end of this.”


People are incentivized in those three ways. In the near-term, needs are met. Over the medium term, you get that bonus component that incentivizes you to make sure the company is doing well with those medium-term goals, and then the long-term goal is that if we build a company that has lots of customers that are very happy, then we’re all rewarded by that. From a compensation standpoint, that’s how we think about it, but I think that in-between those times is where I think that you can make a lot of difference as well, is just reaching out to people and telling them, “Hey, you know what? I think you’re doing a great job. I think that the lessons that you’re creating, or the way you’re able to connect with some of the difficult students is really impressive. I want to see more of that.”


Or if we’re going through a website design and we’ve got a pretty tight timeline, and we’re able to make the coding magic happen and get something very impressive out, I think that having those conversations and really letting people know that they’re appreciated and they’re making an impact on the company I think is very, very important, because sometimes those conversations can be almost absent of or independent of the other compensation pieces.


Adam Robinson: You talk about the equity component in this 10-year journey, and I love that framing when you’re recruiting people for the long run. What are you expecting of them on a daily basis that helps focus them on that 10-year journey? I know you’ve got to get done today what needs to get done today, then there’s this vision for the future. Talk about how you manage expectations from all the things that need to get done today, through to maintaining focus on what’s out there to keep people motivated.


Omowale Casselle: I think first and foremost, it starts with the customer journey, and that development of, “Are we really developing a solution that the customer is really interested in?” I think that beyond the customer journey, 10 years is a very long time, right? But I think that it’s a short period of time when you think about how companies have evolved over prior decades and generations. When you think about a Marshall Fields or a Sears-Roebuck, people used to put their names on buildings because they knew they were going to be around for the long haul. If now you look at the dynamic within corporations and companies in general, companies used to exist for, call it 60 years, and a recent study came out that says we’re not at 20 years. Even 10 years in my mind is a pretty short period of time, but I think that something that we try to do is we say that the 10 years allows us to not take shortcuts when we’re trying to figure out the model.


I think that sometimes if you’re looking for an early liquidity event, call it one, three, five years, you’re looking for an exit. There’s some things that you can do to kind of generate exponential growth and do things that might not be the long-term best thing for the company, and so I think that by having that focus further out, and saying, “Are we always looking through this from the lens of ‘Is this the right thing for the customer? Is this something that we’re going to be proud of if we put this into the marketplace? Is this something that we’re taking a short-term benefit versus a long-term gain?'” Those are all lenses that we are constantly looking at and looking through.


I think that that’s where the initial longer term framing came from, is that you can get people who say they want to do a startup and say they want to get involved in the early stage building, but there’s very few people who when you say 10 years, that the roller coaster … And we try to be very, very clear on what a startup is like. “It’s the hardest job you’re ever going to do, and there’s going to be ways that you push and you challenge yourselves that you didn’t even think was possible.” That longer-term framing, and then collapsing it back to the daily decisions through the lens of the customer, I think has been most helpful for helping us work through that.


Adam Robinson: Have you developed core values for Digital Adventures?


Omowale Casselle: Absolutely. Absolutely.


Adam Robinson: Take us through those, if you would.


Omowale Casselle: There’s a couple things, right? What our number one goal is, is that we’re trying to exceed the expectations of our clients. We think about those as both the students and the parents, and we think that there’s a couple ways that we actually accomplish that. It’s through innovation, right? The education technology landscape is ever-changing, and so it’s never acceptable for us to sit back and think that our solution is going to continue to meet the needs of our students. What we try to focus on from an innovation standpoint is constantly investing in developing new solutions that we can incorporate into the platform to meet the changing needs of the industry.


The second one is creativity, right? There’s many ways to solve problems, and our goal is for our coding classes and technology camps to be creative while also developing the problem solving skills all students need for tomorrow. In our mind, our students are unique, and we plan to always utilize creative approaches when we think about, “How do we differentiate instruction?” And, “How do we maximize our individual potential?”


Third thing is ownership. The success of our students is directly connected to the ongoing success of our company, right? We’re just as committed to helping our students be successful in life as we are to helping them through overall coding projects, so we basically task our instructors with working closely with students to figure out what type of projects they’re going to enjoy working on, what areas they continue to strengthen and develop their expertise, so that over the long-term these are going to be students that are able to really make their mark on the world.


Results. We think a lot, a lot about results. We think that if our students aren’t developing their computational skills, their engineering logic, and their ability to solve problems, then we’ve failed. What we do is, we focus a lot on keeping track of progress. Not necessarily through a traditional grading progress process, like a school, but really through capability assessments, and really saying, “Can you work within a set of boundary conditions to accomplish a given outcome?”


Then the final thing is really accountability. In a relationship, there’s always this opportunity or potential for misunderstanding, miscommunication, or disappointment. Anytime a customer feels like we’ve let them down, we always ask them, “Is there anything that we can do to make it right?” In our mind, there’s literally nothing worse than a customer who is unsatisfied, and so oftentimes they give us a chance to make it right, and we basically say their success is our success, and if you look at our reviews, we’ve got fantastic reviews across Facebook, Yelp, and at the five-star level, which is something that we’re very, very proud of, given the number of kids that have walked through our doors over the past two-and-a-half, three years.


Adam Robinson: That’s fantastic. To bring this home here for our listeners, what are some ways you make those values real or reinforced in the workplace to make them authentic in the lives of the people who work for you?


Omowale Casselle: I think it’s really about the lenses, right? I think it’s really about, when we’re coming to key decision points, are we [inaudible 00:23:05], for example, from an accountability standpoint. We have a $19 trial that we offer, so that if people aren’t quite sure about our platform, they can do a $19 trial. Sometimes we’ll reach out and basically say, “How was your experience during that trial? Did it go well? Did your child enjoy it? How did we do?” Sometimes parents will come back and say, “You know what? It wasn’t right. You guys fell short for whatever reason.” We’ll instantly refund that. Those are real costs that we’ve incurred, but the much greater cost is that we haven’t done a good job at actually delivering on what we said we were going to do, which is offering an amazing experience within our studio.


Not only do we refund it, we’ll invite them back and say, “You know what? We heard your feedback. We heard your concerns. We want another chance. Give us a chance to make it right.” Oftentimes we find that we’re able to more than win back the folks that weren’t quite happy with what we initially delivered. I think that that’s the way you make it real. When people see that, from an employee standpoint, that we’re willing to refund trials and basically give a double benefit for our customers, I think it’s very hard to say that they don’t have individual accountability.


From an innovation standpoint, we have monthly brainstorming sessions where we try to go through and say, “What are the ways that we can improve on our product for the customers? What are things that we haven’t even thought of? Things that are not right in front of us, but are maybe three or five years out, that we can start to back-solve for?” I think that making it real by talking about it on a daily basis and actually putting it into play really helps make those values real for our employees.


Adam Robinson: Outstanding. Final minute here. What book is on your nightstand right now, and would you recommend it to our audience?


Omowale Casselle: Yeah. Something that I’ve recently dusted off was How to Win Friends and Influence People by Dale Carnegie. I think that I certainly recommend it. I’ve read the book many times myself. I think it’s just such an important book on figuring out how to get outside of yourself and really demonstrating empathy for others through a series of things that really shows … A series of his anecdotes and stories that shows that it’s not always about you. Sometimes it’s super, super helpful to take on someone else’s perspective and not to be so critical and judgmental. Definitely recommend it. How to Win Friends and Influence People.


Adam Robinson: Fantastic. Fantastic book. For me as well, one of those early reads in my career someone handed to me and said, “This is really most of what you need to know to be successful in business and life.” They were right, and that’s such an outstanding classic that holds to this day.


If you were to come back on this show a year from now, and report to us whether or not you successfully tackled the single biggest opportunity in front of you in the business, what will you be telling us happened?


Omowale Casselle: I think I’d be talking about that we’ve successfully figured out how to develop the next generation of student talent, as well as the next generation of instructor talent. When you think about coding, and programming, and digital solution development, a lot of this stuff people didn’t necessarily see as they were coming up, which is what we’re trying to solve for. On the one hand, we’re developing a series of projects, hardware and software projects for kids, but we’re also developing a group of instructors that’s able to deliver this next generation of education in a way that kids really enjoy, in kind of this really state-of-the-art environment in our learning studios.


It really requires, I think, a lot, a lot of both intellectual horsepower and stamina. We’re open six days a week now. We run a very, very heavy load during the summers, and winter breaks, and holidays, because at the end of the day, we’re a retail-based business. Figuring out how to take the educational aspects, incorporate the retail, and then develop that next generation of instructor that can actually deliver it, if we’re able to solve for that, I think that that’s the current limiting factor to our growth, and we’re really excited to figure out how to get on the other side of that.


Adam Robinson: That’s the final word. You’ve been learning from Omowale Casselle, co-founder at Digital Adventures, based in Chicago, Illinois. Thank you so much for being with us on the program today.


Omowale Casselle: Absolutely, Adam. Really enjoyed it. Thanks for having me.


Adam Robinson: That’s a wrap for this week’s episode of The Best Team Wins Podcast, where we’re featuring entrepreneurs whose exceptional approach to the people side of their business has led to incredible results. My name is Adam Robinson, and I wanted to thank you for joining. Check out the book The Best Team Wins,, available in all formats and through Amazon. Thanks for listening, and we’ll see you next week.