Action and Ambition

By Rise8

The two ingredients required to spearhead digital transformation.

By Rise8


Rise8 founder and CEO Bryon Kroger was on Entrepreneur’s podcast Action and Ambition in Nov 2021. At just 27 minutes, it’s an easy and engaging listen.


Phillip Llanos [00:00:10] Thank you for tuning into the Action Ambition podcast. I am Phillip Llanos, and today we are joined by Bryon Kroger. He was a captain in the Air Force and saw a need for advanced tech in the military. So he created Kessel Run, the precursor to Rise8, which represented the first systematic attempt to develop a technological driver within the Air Force. Now Kessel Run was an official U.S. Air Force program office, as it is, and he was COO responsible for spearheading digital transformation, adoption of tech, and finding faster solutions to problems from inside the Air Force. But Bryon was still faced with hurdles, so the day he separated from the Air Force, Bryon opened the doors of Rise8, which is a digital services company that goes beyond consulting. Bryon, welcome to the show. How are you doing, man?

Bryon Kroger [00:01:05] Great thanks for having me.

Phillip Llanos [00:01:06] Absolutely, absolutely excited. It’s rare I get to talk to somebody who was originally in the military doing things and at an executive level, but also in tech doing things at an executive level. So I think there are some parallels and lessons that I’m going to try and pull out what the listener can walk away from this going, “oh you know what? I’ve got to have more of a military mindset for things and more of a tech exec mindset.”So that being said, why don’t we start where I think it makes sense. Do you come from a family of people in tech or the military?

Bryon Kroger [00:01:52] Definitely in the military. So my brother, who is somebody that I always looked up to, he was in the Air Force. He was actually a finance troop. So, you know, not doing combat stuff there, a lot of support stuff. But yeah, I’ve always really looked up to him. He actually got out. He was a master sergeant, retired from the Air Force and then went back to work for the Air Force as a government civilian. And then I have other folks in my family that were in the military so I was familiar with it, but I didn’t have anybody like driving me to go to the military, per se.

Phillip Llanos [00:02:23] Right, OK. And then so does tech come into the picture just because you’ve always had an interest in it. Or was it like you saw the need for that in the industry you were in and said, Well, somebody’s got to step up to the plate and that’s somebody I guess is going to be me. Was that sort of the way that happened?

Bryon Kroger [00:02:41] It is, yes. So I was I was in the Air Force for 10 years. For the first seven years, I was an intelligence officer. I did it primarily targeting a lot of counterterrorism targeting. And we have some of the most advanced technology on the planet. But at the same time, I was back in the operations center using some of the oldest and most atrocious tech on the planet. I mean, it’s like walking back in time when you walk into your office. So we tend to spend a lot of money on the forward-facing things the planes, the tanks, the ships, but not as much on software. And so with that, you know, I saw some pretty crazy things during my time, you know, young Captain Lieutenant Kroger was on the Operation Center floor using Excel spreadsheets, a downloaded copy of Google Earth and a stopwatch to calculate the ground speed of moving targets and make life or death decisions. And, you know, time-sensitive calculations. And so for me, I think, you know, it’s a story that we have on our website, but the turning point for me was not that thankfully, I wasn’t a part of, which was the Kunduz Hospital incident in which we struck a Doctors Without Borders outpost and killed several international doctors and other innocent lives were lost that day. So for me, you know, the tech side of that was kind of a footnote in the report, and I can’t say that better software would have made anything different that day, but I certainly felt like it could have made a difference. And for me, that was the turning point where I hung up my intelligence badge and went over into the tech side of things where we traditionally procure software in the Air Force and instead of buying software, I came up with this idea that, you know, we really need to transform the DoD into a software company in the war industry. And and how do we make a capability where we can continuously deliver war-winning software that airmen, soldiers, sailors, marines actually love to use? You know that joyful experience when you pick up your phone? How do we have that same concept of super valuable software that’s continuously delivered and people love using it? And so that’s the mission I set out on with Kessel Run.

Phillip Llanos [00:04:50] That’s really cool to think of creating a UX and UI that sort of favors the mindset and sort of where the disposition of someone flying an aircraft or someone manning any kind of equipment that needs software and that it isn’t like Windows 98, right? You know, like that it has this sort of intuitive because we have the opportunity and the potential and the technology to do that right. So I love that you decided to step up yet again. There’s this theme again. You stepped up and said, OK, I’m going to go here and I’m going to be the one that leads the charge in this tech support intelligence. Right. So all you did was go a level deeper. And so you did that internally before founding Rise8?

Bryon Kroger [00:05:37] Yeah, yeah, and luckily, there were a bunch of people that stepped up with me, otherwise I never could have done it. It was a pretty awesome team that we created that Kessel Run and we scaled up to an organization of about 500 folks doing DevOps first. When I say true DevOps implementation in the DoD, where we’re actually continuously delivering software to warfighters in the field, including on secret and top-secret networks. So really pushing through, you know, some of the big barriers you run into in large enterprises that have large bureaucracies like the DoD does is, you know, getting through security and testing and all of the gates and controls that they have in place before you can actually get in front of a user. That’s why small tech companies are, you know, beating out the Fortune 500s. And so we figured out how to automate a lot of those controls in that compliance and testing in a way that allowed us to push out quickly to the end-user.

Phillip Llanos [00:06:30] Absolutely. Because I imagine there’s also a set of users that you had. There were beta users, right, so that you could work out some of the bugs because that’s going to be a thing with any software. And if you have to go through eighty two pages of approvals before you finally issue out the beta and then, oh man, forget about it lives are on the line here. Is that sort of what sort of inspired you to be like oK, I’ve been able to automate this here, but I really want that full flexibility and freedom, so I might have to go as an external partner. Is that sort of where it came in?

Bryon Kroger [00:07:01] Yeah, to a degree. You know, I say, like I left targeting because I hit a software ceiling. I kind of left Kessel Run because I felt like I hit a leadership ceiling. You know, there was a scaling this idea of a software company inside of the Air Force at the time. You know, I was always going to be limited to where I was stationed. Which isn’t to say you can’t have an outsized impact. I mean, we certainly did at Kessel Run. And you know, I could have gone on and done that from there. But with Rise8, you know, I could really spread horizontally. And in digital, you’re not looking for vertical scale anymore. You want horizontal scale. So it’s a very hierarchical organization, and most of your limit is vertically scaling. With Rise8, I can go wide. I can hit the army, the Air Force, the Navy, the Marines, the Guardians, and I can hit four or five different programs within each of those and spread some of the knowledge and skills that I gained at the Air Force through Kessel Run with a lot wider reach. And also, you know, frankly, one of the things that we run into is, you know, it’s going to take time before the Department of Defense can build up a cadre of tech like true software developers, UX designers, UI designers, you know, product managers instead of program or project managers. And so building that up over time. You know, in the meantime, they’re going to have to really leverage the industry. And that’s what we had to do at Kessel Run, right? We contracted with industry partners to build out our senior software developer ranks and our senior UX ranks, and I started running out of companies to go to when I was at Kessel Run. And so I recognize there’s this gap of people that could provide defense savvy with Silicon Valley savvy. And so bringing those two things together with Rise8 was another thing that I thought could really make a difference, besides being able to work horizontally scale, I’m going to provide a lot better talent. The DoD just wasn’t getting at the time.

Phillip Llanos [00:08:50] That makes so much sense. And also, why should we wait for someone to go through the same set of experiences you did before they update the tech in other verticals that are that are part of the DoD? I think it makes so much sense what you’re doing again, you’re just going levels deeper. It’s starting to make logical sense how you see all those things happening and now I noticed that there was this idea of like consulting and going beyond it. Do you find that there is a current status quo in general consulting that maybe leaves things to be lacking. And in and your words, what is that and how is it that Rise8 is decided to step in to fill that?

Bryon Kroger [00:09:33] You know, I empathize with strict consultants because and I run into it as well, even with Rise8 is you lack control ultimately. And so you don’t want to have accountability for something that you have not only no authority over, but really like very limited ability to impact. It’s a risk. And so that risk that outsized risk causes most consultants to stay in the lane of advising and only, you know, owning that from a performance perspective, whereas I put myself squarely in that risk category, I take on a lot of risk of, you know, the government could just say no to everything that I’m advising. We’re delivery consultants. So we come in alongside them and actually build software. You know, our ideal engagement would be building software alongside US soldiers, sailors, airmen, marine, upskilling them. So they’re getting a really cool product, but they’re also getting an upscaled airman that’s going to go on to be that next tech leader. But, you know, as soon as we step into that realm again, we incur a lot of risk. And so I think a lot of vendors don’t want to step in and have that kind of model where they take on that amount of risk. But for me, it’s about purpose and mission and purpose over profits. And so with that, you know, it’s it’s a risk I’m willing to take. I think the other aspect of it that’s really difficult in defense, you know I mentioned I want to turn defense into a software company and bring in Silicon Valley savvy, but like, how do you actually get people from the valley or, you know, that generally touch Big Tech to come and work in defense has been a really interesting challenge. And you know, something that you know, I would tell your listeners is a lot of people are turned off by defense and I get it right. Like, I sat at the crux of kind of where the ethics comes to a head. And my thing would be, look, you know let’s all make the military that we want it to be. You know, the military is going to go on no matter what we do, right? And that’s political. We have that conversation at the ballot box. But whatever the military is going to be, do I want to make sure that they have all of the data that they need to avoid a future Kunduz Hospital incident or this recent strike in Kabul, right? Like those are impacts that you can have you might not agree with overall with what the military is doing, but you can make tomorrow better by being a part of the story. And it’s those voices, those exact voices that are trying to walk away like, I don’t want to be a part of this are the exact voices we need in the conversation and the folks that we need leading tech development in the DoD. So, you know, that’s been a big focus of ours, of bringing those people in. They don’t want to be consultants, either. So giving them really cool projects that they can sink their teeth in to make a difference. And then, you know, my job often is going and selling that not just to customers, but selling that to the talent out there that we really want to bring in to defense. And so that’s been a really big focus of having this delivery mindset, even though we consult, delivery is what’s really important to us.

Phillip Llanos [00:12:31] 100 percent, 100 percent. And I’m so glad that you went deeper than I think the question even warranted because people can sit there and complain about the way a situation is going, the way it’s developing, or they can step up and be part of it as well and then control or have their own influence on where things go in the future of defense. And why not have the brightest minds? I understand there’s the ballot box situation, but there’s also the real-life you get to be a part of saying how this might go if all things align. And while it is a risk because then you know you’re tangled in that, at the same time, it’s even more of a risk to leave the entire country at risk because you don’t want to be a part of it. So there’s just a really interesting conversation going on. At the same time, I can see how that plays a role. And then being able to attract talent, knowing that they would rather do almost anything else that’s flashy. But really, these projects are the ones that have deep roots and can span…I mean, this again, purpose over profits, really, but the profit will be there. You know, people will get compensation. That’s that goes without saying. Now, as a previous captain, do you find that there are any experiences in that leadership role that sort of carry over into business?

Bryon Kroger [00:13:50] Yeah, definitely. I think one of my favorite parallels here is Google’s Project Aristotle, where they studied the performance factors for high performing teams, and I think it was a surprise to everybody. Originally, when they did it, what actually came out of that study, there are five main factors and four of them really align with military culture, and I would say not only that, but leaders -both enlisted and officer ranks- coming out of the military really are awesome at these. They are dependability, team members get things done on time and meet the high bar for excellence, structure, and clarity. Right? Having clear goals, plans, clear roles meaning that the work is personally important to team members and then impact. Team members think their work matters and creates meaningful change outside of the team. Those are all things that are just like…you can say that they’re also tech, but they’re very military when you think of them. I think the one area that the military does struggle and was something we had to do differently at Kessel Run and was a personal transformation for me, is the number one trait that the Aristotle project found, which is psychological safety and in fact, a lot of times in the military with the kind of command and control hierarchy and things that, you know, arguably do need to do on the battlefield are not things that you need to do back stateside when you’re developing software. And this is about making team members feel safe to take risks, be vulnerable in front of each other. And so one of the things that we did at Kessel Run in and I’ve continued as just a general principle that I think it’s hard for some military people. In fact, some former military people introduce themselves, I’m former captain so-and-so. Or they’ll even put it in their LinkedIn…is, you know, putting ideas over title and ideas over rank. So at Kessel Run, we actually didn’t wear uniforms. We had an office in downtown Boston, one Beacon Street. In fact, they’re still down there, you know, like right down there near the Boston Commons. And they all come in without uniforms, except for, you know, sometimes we do warrior Wednesdays. But for the most part, the idea is you have that rankless environment and really putting ideas at the forefront, not titles, not highest paid person’s opinion and making that the focus. So I would say, yeah, the military, I think, really trained me really well, except for in that one area, I had a lot of unlearning to do and relearning, and I’m thankful that I had that opportunity.

Phillip Llanos [00:16:16] I’m so glad I asked that question, because that’s such a key pivotal trait in business is the ability to create an environment where ideas people aren’t afraid to share their ideas right? And even if it’s a bad idea. And it’s not like, how dare you even think that you could be the one to even you like…and that that leads to innovation. Right? And so psychological safety is innovation, and innovation leads to further success in business. Yeah, super cool that you brought that up. And I’m so glad that I was able to ask a question like that. So in a world driven sort of by tech and software, have you found any traps aside from the red tape that you’ve experienced in your operations and your whole career, that sort of people in business may want to become aware of or cognizant of as they move things forward because some people are still brick and mortar saying “I don’t want to get on Google my business”. And so maybe anyone in business can learn a thing or two from someone who has been on both sides of something that’s very, let’s say, been around for a long time and maybe a little hesitant to change and adopt new norms. And then the other that is all about new norms and maybe never really adopting anything at all. Right, so you’re at the crux of those two extremes. Is there anything that you’ve fallen into the trap that you found yourself when you said I will now know for next time that maybe you can pass on to the listener?

Bryon Kroger [00:17:36] Yeah, the big one that always comes to mind is the the alignment trap, which is a well-studied problem. But I think it broadly applies to business in general, which is this idea that, you know, you can get so caught up in planning the value that you’re going to create versus establishing the feedback loops first. So, you know, this is a classic Zappos story of, hey, do people even want to buy shoes online? There was a famous grocery store chain in the Dot-Com era blanking on their name right now. But you know, at the time it was a question like will people buy groceries online? Instead of validating that first they went out and bought all of the logistics they got like factories, they got trucks, they got all the infrastructure, multimillion dollar investment, as you would expect in the era, and then nobody wanted to buy groceries online. Zappos founder was like, I’m going to walk into Foot Locker, snapped some pictures of shoes, put them online. And then when people bought them, he would go into Foot Locker, buy them, ship them to the customer, right? A Wizard of Oz to validate that people would even buy shoes online. And then obviously, once he validated that, you know, got going. And so the lesson there is establish the feedback loops first. And, you know, don’t get carried away with planning and I’m guilty of it. You know, I live in this lean, agile, you know, like Fast Tech, let’s deliver every single day, we’re going to deliver new software. But even I can find myself on the business side of things getting trapped in like planning, planning, planning. And you still gotta have plans don’t get me wrong, but you got to make sure whatever plan you’re putting in place, you have a means to validate or invalidate that plan and that comes from feedback loops, whatever those might be for you. So that’s always number one for me. Any new thing I’m doing, I figure out what’s the what do I need to learn and I’m going to set up that feedback loop first?

Phillip Llanos [00:19:29] No, it’s so key, especially when we relate it back to your experience. You talked about earlier where there’s all this red tape that you had to go through just to get a beta out before you could even get the feedback so that’s just another example of not being able to get feedback as soon as possible to iterate at the speed that people are looking for. It’s ironic that we think if we have a plan, well, then we’ll be able to speed through that right? That a dollar saved some penny earned something like that. But now, especially in a world like today, you got to put the pedal to the metal, crash the car first and see how fast you can go before it crashes, right? That’s what you’re saying. Without actually crashing cars, nobody crash cars.

Bryon Kroger [00:20:12] Don’t crash cars. Yeah, yeah, yeah.

Phillip Llanos [00:20:17] Yeah, lots of dollars there. No, I mean, I really appreciate you being able to indulge all the strange questions I’m asking and open up about your career and your journey so far. I want to invite you to go ahead and tell the listener, like, what do you have planned for the future with Rise8? Is there a new specific branch that you’re looking to go into for a vertical and also how can they connect with you, with you online, that kind of thing?

Bryon Kroger [00:20:44] Yeah, absolutely. So you can find us at and then we’re here on all the socials as Rise8. LinkedIn is where we’re most active and we post a lot of memes, so it’s a fun follow. And as far as future plans, I’m focused on scaling. Like I said, I need horizontal impact. So, you know, we’re scaling horizontally not only across the DoD, but I think it’s really important, you know, the DoD is always going to be my focus, my first love. But there’s a lot of impact to have across the whole of government. And so, you know, this year, one of our goals was to branch into federal and larger federal space. We have a really cool project with the Department of Veterans Affairs still kind of close to our, you know, DoD roots. But we want to expand beyond that, maybe into CMS, Medicare or Medicaid, those types of projects. And then I do want to have a small portfolio of commercial projects, too. It’s a great way to keep people fresh, you know, rotate people between commercial and government. So, yeah, right now it’s about scaling our current service offerings around cloud platform and continuously delivering apps that people love. One one other thing that I would say is my my big goal and my big, hairy, audacious goal out there in the future is I’m really serious about transforming the Department of Defense into a software company. I don’t want to quit until I can look and say, wow, the DoD has gone digital. They’re a digitally native organization, and they can sense and respond to threats in any domain, anytime, anywhere with software. And so that’s that’s my goal. That’s what you see from me in the next 20 years.

Phillip Llanos [00:22:21] I can’t wait to be honest. I remember watching a documentary in Estonia, which I think is like a fully digital internet-based country. And then they did get hacked. And instead of like trying to hide it or whatever, they actually owned up to it and put a message out to the world and said, hey, we’re calling on all programmers who want to be a part of developing a country that’s fully digital. And in doing so, they truly, I mean, it’s a way smaller country than, you know, the United States or whatever. But like can’t wait for that day so that I don’t have to wait in line for a thing that could have been done online. “This could have been an email” could be said about a lot of things in government, and so I can’t wait to see what you end up influencing in that sphere of things. So Bryon, thank you so much, man. I have one last question as I close things out and I hope you’ll indulge me, but you’re also welcome to pass, and that is if we could have invited anybody today to join us dead or alive, to sort of chat with us and visit what your career has been so far and where it’s going, who would it be? Dead or alive and why?

Bryon Kroger [00:23:27] Have to go with Alexander Hamilton. Yeah. Maybe we could sub in Lin-Manuel.

Phillip Llanos [00:23:36] Yo yo yo!

Bryon Kroger [00:23:38] No, it’s so funny. You know, like my journey at Kessel Run was a pretty tough one. We often likened it to a revolution of sorts, and so Hamilton was often just a rallying cry, the soundtrack and kind of the whole story there of Hamilton and, you know, even embodying a little bit of Hamilton. At Rise8, we have a Layfayette award because we consider him the first Riser. We talked about defense and the ethics and everything, but it’s a really great experiment, you know? And like there’s there’s a lot of things that were wrong with our country when it was founded and still are today there is a ton of room for improvement. But I think the idea that we keep improving and that we’ve stayed true to those ideals, even though some of the founders’ underlying premises were wrong and needed improving, I think it would be really interesting to have them here today and get their reaction. I think we’d be surprised to find that, you know, even when we’ve gone against some of the things they maybe had in mind or some of the underlying premises they had, I think they’d be really excited to see what we’re doing. And also that, you know, again, I’m out here trying to to defend freedom in a digital age, which can look very different than traditional war and all these ugly things that even I don’t care for. And so I would say, you know, having somebody like that here would be really cool, and I might ask him if he would be a part of the revolution.

Phillip Llanos [00:25:07] I’m 100 percent sure that includes Benjamin Franklin for sure, right? What I love about this entire thing throughout the entire conversation is this idea of like the notion to say, “it’s always been done this way” is no longer something we should have as relevant because anything that isn’t broken can still be improved. And that’s where we should look at things, is that the constant in life is change and really embracing that as digital continues to move forward. Augmented reality, virtual reality, don’t even get me started. There’s so many avenues that are going to open up and yeah, thank you for the work that you’re doing, getting the government and Department of Defense to really come into where they’re supposed to be technologically even in terms of a framework and mindset. So again, Bryon, it’s been an absolute pleasure. I hope it isn’t the last time I’ll be connecting with you. Post this and see what else I can do to help, but thank you for everything that you’re doing. Thank you.