What actually gets in the way of delivering good software in government?
In this honest and insightful conversation, David Blackburn (CEO of OrangeSlices AI) sits down with Bryon Kroger (CEO of Rise8) to talk about the real-world challenges behind federal software delivery — and what needs to change.
They cover everything from outdated contracting models to the disconnect between acquisitions and operations, and why focusing on outcomes instead of outputs makes all the difference. If you work in government, contracting, or software delivery, you’ll walk away with ideas you can actually use to push things forward.
Transcript: David Blackburn and Bryon Kroger
David Blackburn:
This is David Blackburn, CEO of Orange Slices, and I am excited to be here today with Brian Kruger, the founder and CEO of Rise8, who is one of the most exciting and relevant companies in the market today. A former U.S. Air Force targeter, Brian saw firsthand the devastating impact that bad software can have on mission success. That experience drove him to co-found Kessel Run, the DOD's first software factory, where he helped pioneer the first continuous authority to operate and redefined how the government delivers software. Today, through Rise8, Brian is leading a movement that's transforming how the defense and federal community think about technology, speed, and culture. From hacking bureaucracy to delivering mission critical software at 25 times the pace of traditional methods, Brian and his team are showing what's possible when innovation meets purpose. Look, let's get into it. Welcome, Brian. Excited to have you here.
Bryon Kroger:
Thanks for having me.
David Blackburn:
So look, you, you founded Rise8 after co-founding Kessel Run, which of course gave you really an opportunity to see firsthand what worked and, and what didn't. So what gap did you see in the defense industry that made you want to start Rise8, and how did that shape your vision on what government and industry partnerships really should look like?
Bryon Kroger:
Yeah. When we started Kessel Run, you know, there's famously the OTA, it was actually the Air Force's first production OT, that we awarded, out of lifecycle management center to a company called Pivotal. Look, they were a great partner. I owe, everything that, that happened at Kessel Run to them. It wouldn't have happened without them, but it wasn't enough, right? I ended up having to let, 12 more contracts in the first year to stand up the IT tool chain, the production environments. It was a lot more that had to be done, and then there wasn't really anybody to wrangle all of that, right? There was no system integrator, we were the integrator, and that experience really drove me to, look across the market and say, why, why is this so difficult? I've got this problem that needs to be solved and I have to go to 12 different places to get it solved, and then I have to be the one to, integrate everything. And we're not just talking about integrating technologies, but we're really talking about, you know, dealing with cross-vendor disputes, all kinds of things. Things I should not have been focused on in my, my role. I should've been just focused on the product and the outcomes for war fighters. So, I wanted to be able to provide one place where the government could go to get that end-to-end, digital transformation, and to be able to, to integrate all of those digital services.
David Blackburn:
Great. Thanks. So, I guess one follow-up question is, I've noticed that, I guess it's the tagline of yours is, "We ship outcomes." So where does that come from? Is the efficiency and that focus based on your time in the military, or has that been just the way you've always operated? Love to hear more.
Bryon Kroger:
I mean, during my time in the military, the big thing for me was this huge disconnect between acquisitions and operations. And you know, it was like, the goal over in acquisitions was to complete this requirement spec sheet, but nobody ever actually checked in to say, "Well, did that actually meet the war fighting need? Did it fill the, the critical gap that was identified in the Jasons process?" Right? We skipped that part. We're like, "Oh," pat ourselves on the back, we, completed the contract, checked all the boxes. And so that was always really frustrating to me, and I saw missions fail and people die because of that disconnect. And so, I wanted to see mission impact, and over on the contractor side of the equation, people are incredibly focused on outputs. And there was this great work by, Josh Seiden, he wrote the book, Outcomes Over Outputs, and he actually has a little graphic of this, that we've, co-opted here at Rise8, which shows that the missing focus area is outcomes. And he defines outcome specifically as changes in human or user behavior that produce impact, business results, or in our case, mission results. And so that's the part that we as software developers can control. I don't actually get to go operate defense missions, right? But I can ship them outputs, software features, and then I have to care about the actual changes in user behavior and does that impact the mission or not? And if not, I need to go back and iterate, and that's the piece that's always been missing. And so, that's why we have this relentless focus on outcomes.
David Blackburn:
Yeah, that's great. So, so you are so outcome-focused. I guess, why do you think other companies struggle with this so much? Or why is it that the, the government in general struggles with this? That's true. Because it doesn't seem like everyone's following the You're, you're on your own path, but I don't see a lot of folks trying to do what you're doing. Maybe you do.
Bryon Kroger:
Yeah. It's, it's primarily, as much as I'm hard on contractors sometimes in the defense industrial base, this is one that's a reflection of the government, and so if, if you write contracts that are based on outputs, deliverables, you're gonna get outputs. Simple as that. And it's not just that the contract is asking for them. The entire incentive structure is built around that. And in fact, there are many contractors that want to do what we do, and they're actually disincentivized. They would be penalized for going off and talking to a user and saying, "Oh, actually these 4 things in the spec sheet, they're not right. We need to do something else." If they went and delivered that thing, even though the war fighter loves it and the mission is better for it, the contracting officer's gonna come back and be like, "You didn't do items three, four, five, and six." I'm gonna give you a bad CPARS and maybe cancel your contract. Right? And so, it's, it's, really a contracting problem, and behind that, a philosophical problem, this huge divide between acquisitions and operations in, in the military and in, in the larger federal ecosystem.
David Blackburn:
Yeah. So, so, you know, given the, your approach to the market is so different, do you find that How important is culture, right? I've s- you guys have clearly had a lot of growth. You've had a lot of success, right? You've had a lot of wins. I've, we've certainly, I think we've talked about several of them, and I know you guys are consistently rated as one of those best places to work by a number of different places, but how has that, how important is that culture and how important is that in helping you guys have success to date?
Bryon Kroger:
It's number one. When you, when you set out to achieve outcomes, you're not being told what to do, right? And so, like if your, deliverables-focused or outputs-focused, contracting organization, your employees know exactly what they need to do. You literally hand them the, the SOW or whatever, right? Work breakdown structure, go do these things, ship it. That's a very different type of employee than the one that I have, which says, "Hey, we're going to work backwards from this mission impact." They wanna reduce the amount of time it takes to generate space support requests by 25%. Or even better, they don't actually know what impact they need to achieve yet. We actually go have to help them We have to help them go do that first. Define the current state of the value stream, identify the target state, where can we improve the mission? And now go build the software. And now I'm having them work backwards from impact, and so you need people that are, 1, masters of their craft, and then also pair that with being very entrepreneurial. So I want them to have agency, ambition, and then there's, 2 behaviors that are really important, which is, tactical urgency paired with strategic patience, and I think in the innovation crowd and a lot of these new starts, they've got a lot of that tactical urgency. They actually really suck at some things. In fact, they maybe even criticize things about, planning. There's a lot of people in the agilist community that are, anti-planning, and, plans are still important. Strategies are still important. Military guy, so I gotta quote Sun Tzu, right? "Tactics without strategy is the noise before defeat." And so instilling that culture of, being able to be strategically patient while, violently executing at the, at the code level, and then having the agency and ambition to carry that out yourself, if I don't have those employees, there's no way I can scale the company the way that we are. The amount of overhead would just be massive, to be able to continue to ship outcomes. And so, we, we are very, dogmatic about our culture in a way. I like to say, we have very strong opinions at Rise8. You see them come out on social media, maybe in this podcast. And, I like to say we ha- we have strong opinions loosely held, and that's not quite accurate. It's strong opinions loosely held about implementation, but we should have strong opinions probably mediumly held about our processes, and we should have strong opinions strongly held about our culture.
Bryon Kroger (continued):
So, like I, there are different philosophies on, you know, "Oh, you should have a very open culture that invites everybody," and it's like, cool. I understand that's your culture, but you're probably not a good fit here. And so I actually believe in a bit of a monoculture if we're talking about values and principles and practices. And, and then less so, being a l- less opinionated when it comes to implementation.
David Blackburn:
Yeah, I get it, right? With what you guys are trying to do, you're definitely looking for somebody who is a specific breed and, makes sense, right? You're trying to get to where you're going. So, I did notice you guys, eh, some announcement earlier, I think it was today actually, that you guys were talking about an event you're doing, that you're bringing some developers together for some type of a camp, and I don't know if you wanna talk a little bit about that, but I'm assuming that's clearly an opportunity to Uh, is that a recruiting, thing, or is it a learning, or all of the above and everything in between?
Bryon Kroger:
Yeah, primarily learning, similar to our Prodacity event. I'll tell you, I this space doesn't have a lot of good learning opportunities. Al- almost all the conferences, even when they're billed as learning opportunities or networking opportunities, they're just, slimy BD. You know, the sponsors buy in, most of the talks are paid for, and everybody's just trying to sell something and it's super disingenuous. And so I created Prodacity, which, I make no money. I lose a massive amount of money. It's, it's like a it's my giving back to the community, as I call it, as a place for government leaders, and I say leaders at all levels, to learn about transformation. And after the first year, people were like, "Hey, that was great, but I'd love to see more, practitioner content." "How do you actually code differently? How do you think about products differently? How do you think about user interaction differently?" And so we started building that into the Prodacity agenda, but it was just, too much to fit into one agenda. And so this year, we're breaking it out into Prodacity is gonna continue on, but it's gonna be focused on leadership and digital transformation, and Ship Summit is the new one that's launching. That's gonna be for practitioners, by practitioners. There's, one day of learning and content of, what's the latest bleeding edge? This year, there's obviously a big focus on AI, but not in the, flowery sense and, all the hype, but, what are things that you can take for the next 2 days? And we're gonna do a hackathon or a build. We're actually gonna build something and solve a real problem in gov tech together, with broken out into balanced teams from all of the members. And so, going back to my earlier thing too on culture is, it's one thing to attract the right people into the door, get them into the door, but then we wanna continue to invest in them, not just in skills, but also in practices and values, attitudes, beliefs, the cultural aspect. And one of the ways we've done that at Rise8 is we- we do an offsite every year, but unlike most company offsites or retreats, ours is focused on- on professional development. And so this is kind of the next iteration of that, where we actually invite people into our culture. So, I basically have transformed our internal training program into something we're offering up to government practitioners and even our partners and frenemies, to come in, and we're gonna teach them all of our secrets, but the goal is- is learning and growth.
David Blackburn:
Yeah, I love it. I think it's a very- very smart and, yeah, I mean, a great way for people to see your culture and see if it matches, whether it's a partner or- or a customer or potential employee. I love it. So, look, I mean, I like I said, I've been told you several times. I'm like, I'm very impressed with how you guys are going to market. I think it's refreshing, as a taxpayer, as a citizen, as a, you know, just someone that enjoys disruption, right? So, and- and I think a lot of companies want to do what you're doing, right? But they A- and- and they clearly see the need right now in the market to go out of there and- and be bold and bring big ideas, so what advice do you have for those who are trying to drive this type of change in government, especially those who are trying to hack bureaucracy, as you put it?
Bryon Kroger:
Yeah. You- you have to be who you are, you know? I think that, everybody A- a lot of people, to your point, a lot of people say they want to make a- these changes and, lead a- a- a change in the ecosystem, but you've got to put your money where your mouth is. As soon as they start losing bids because they're, too expensive because they hire great talent or, you know I had, I had a contract get shut off after a panel I did once. Literally, 20 minutes after the panel, Carlo calls me. He's like, "I don't know what you just said on that panel, but we just lost the deal." And I think people expected me, I told a couple of people there and they're like, "Oh, you regret it?" "Do you wish you were less spicy? You're always spouting off." I'm like, "No, I don't." If I were being egregious or doing things But, the stuff I'm saying is just truth, candor. I care about war fighters, veterans, clinicians. I want to see a world where fewer bad things happen because of bad software. Some of the things I experienced directly, including death. We're talking about people die because of bad software. That's crazy. And so, yeah, I'm pretty unapologetic about that. And- and what happens then, to your qu- question is, what do you do? Well, your customers self-select in and out. So I would just say, own who you are and what your purpose is, and you'll find your niche. And even if your goal I really don't care about making the money, I want to make the difference, and so I know the only way to make a difference is if I work with other people who want to. So it's just, there's no other alternative for me. But some people are in a hybrid scenario, and that's okay. If you have purpose-driven mission goals for gov tech and you want to make money, I'm- I'm okay with that. It's just that you have to know there's still plenty of money to be made. You can grow a really big company, even though many mentors in this space will tell you, "You can't do what Bryan's doing in scale." We're doing all right. And, time will tell. I don't care if I become, a billion dollar exit company. That's just not a goal of mine. But, I think you could. I think you could do what we're doing and be unapologetic about outcomes and- and excellence and quality and high rates, all the things, and still do really well financially. But it takes courage. And, the second you- you lose courage, you lose everything.
David Blackburn:
Yeah. GovCon's interesting. I was thinking about this. Actually, after, you were on that panel earlier today we had, right? And, I think a lot about GovCon is full of founders and operators. And I'm sure there's And I haven't thought about this tremendously, but this is a town where you can be a great operator and have a lot of success because you understand how to get your rep rate low and how do you- you know, bid something that you get the right partner and, and you can do very well. And I obviously see you more in that kind of founder pushing forward, mission focused. And- and clearly it's ideal to be both, right? To be a good operator and- and a mission-driven kind of founder. But Yeah, I don't know how we get more mission-driven founders, and I think a lot of it's, meaning folks that really do care about delivering outcomes, delivering results, and that, that's a challenge, right? I mean, I don't know. Do you have any thoughts on how the government Is it acquisition? Or some of these changes that have happened in the last year, will they impact this? Do you see some of the things you're doing, is that gonna impact it? What's gonna be that thing that gets the government to understand, we need more of people like you and less on, "My wrap rate's low and I-" Yeah. "won the deal because of that?"
Bryon Kroger:
Yeah. I actually don't care what people's motivations are. I may be, unique in this I always remember when I joined the military, they always asked people, why they joined. You'd sit around in a circle and people would talk about it. And I feel like there's always this, pressure to say something profound and, really purposeful. And I and, and so it's interesting because I've become really enamored with this mission and I care a ton about it. But I'll tell you, when I joined the military, it was because, I graduated from college a semester early and I had become disillusioned with I had planned to go into medical school and I just became really disillusioned with it. I didn't know what to do, and it was in the '08 crisis, and so I joined the military. That was my story, and I would always tell people that, and people would cringe sometimes, because it's like you were expected to have some post-9/11 or my parents or, my buddy or whatever it was story, and I just didn't have that. But I still did really great things for the mission over the course of the next 7 years, and then my last 3 years was just huge. So why do we care why people joined? We should just care what the outcomes are. And so similarly, I think, do we need more mission-driven founders? I think they'll tend to perform better. But if you just make performance the thing, and performance in this case, the government holding people accountable to outcomes that produce mission impact, why do I care if they're driven by the mission like me or if they're driven by profit motives or whatever? As long as the job gets done, that's all we should care about, and so I view this as a the industry is a reflection of government problem, and if we want the industry to change, the government just has to change how they do business. And, I think we are seeing more of that, and, to, to your point, right now I have, I have optimism and I have a bit of pessimism. My optimism is that, the, the sense of urgency is really great right now and the stakes are very high. And I realize some people, that's very real in terms of their livelihoods are at stake, and, and I empathize with that. But I think that will drive a lot of meaningful change. I do have a worry that there's a focus on efficiency right now, and, we aren't addressing efficacy first in some cases, and so efficacy has to come before efficiency. Peter Drucker said, "There's nothing as useless as doing something with great efficiency that shouldn't be done at all," and I see some of that happening. And, the government is famous for building bridges to nowhere. Those are things I don't want to be involved in at all. There's also plenty of really cool missions that just there's no accountability, and so you can be a great operator and do nothing at all for the mission, and that just If, if we get rid of those 2 things, industry will follow suit. And, I don't care what motivates them any more than I don't care at Rise8 if somebody has a master's degree or a PhD. It's like, I'm just measuring your outcomes. If the PhD gets you better outcomes, great, but I'm still not gonna measure the PhD as a proxy, I'm just gonna measure the outcomes.
David Blackburn:
And I love it. Well, look, Brian, I feel like I could talk to you about this forever, and, and I get to see you a lot. You're out there. You're I love that you're very vocal. Please keep being spicy, right? Spicy is what it's about. We need more people out there being spicy and, because yeah, I mean, I think Like I said, I think you bring a fresh message. I think it's one that, if it's not resonating everywhere yet, it should. And I, and I think companies right now are trying to figure out, cheese has moved. How do they, how do they adjust? And I hope you're the model that they're running after. So thank you for the time. Appreciate you sharing your insight, your vision, and look forward to seeing you out there continuing to drive good conversation.
Bryon Kroger:
Thanks. I love what you're doing too, for what it's worth. Orange Slices is the way.
