From Bureaucracy to Breakthroughs: Changing the Face of Government Technology | The Pair Program Ep31

Tim Winkler: 00:00:05

Welcome to the Pair Program from hatchpad, the podcast that gives you a front row seat to candid conversations with tech leaders from the startup world. I'm your host, Tim Winkler, the creator of hatchpad, and I'm your

Mike Gruen: 00:00:15

other host, Mike

Tim Winkler: 00:00:16

Gruen. Join us each episode as we bring together two guests to dissect topics at the intersection of technology, startups, and career growth. Hello everyone, and welcome back for another episode of the pair program. I'm your host, Tim Winkler, accompanied by my cohost, Mike Gruen. Um, Mike, I gave you a sneak peek into my, my question for the, uh, guests here. We always ask Mike, uh, a brain buster here to, to kick things off. But are they, are you, um, are you a condiments guy? I mean, yes. Do you have like a go to, a go to condiment?

Mike Gruen: 00:00:58

I mean, honey mustard is pretty solid. Uh, I mean, I'm not, I'm not a fan of ranch. I'm not a fan of blue cheese. I'm one of those people who doesn't like either of them. So,

Tim Winkler: 00:01:07

so I just heard about this this morning and, um, maybe folks have heard it before, but, uh, you know, there's kind of like freestyle soda fountain machines, like Coca Cola has them in certain restaurants. Um, so Heinz just created a condiment mixing machine where they'll let restaurant customers kind of create their own pre mixed custom dipping sauces. So you start with like a base, like ketchup, ranch, barbecue, like Heinz 57, and then you can bake in like jalapeno, chipotle, buffalo, mango, and then spice it up or down. So I was thinking of like, what kind of, kind of mix would you, would you go with, uh, if you could. You know, get a little freestyle condiment going. Hmm. That's

Mike Gruen: 00:01:51

interesting because I feel like my, the first thing I would try to recreate would be like the McDonald's secret sauce, which is ketchup, mayo, some probably relish. The Big Mac, the Big Mac sauce. Yeah, yeah. Then after that, yeah, I don't know. I'd have to play with that. I like spicy. It depends on what I'm getting, putting it on. Burger. It's different than

Tim Winkler: 00:02:08

hot dog. Hot dogs, mustard. They can mango, ranch, ketchup. Oh, interesting. Mango.

Mike Gruen: 00:02:16

See, I like mango, mango rant, like, I don't know. I'm

Tim Winkler: 00:02:19

yeah. Anyway. Okay. All right. Good stuff. Um, I have to change my pairing. Good. Good to know. Oh, fun fact too on that. So I was doing like research on this for way too long. Uh, but, uh, the, the, the guy that invented that Coca Cola freestyle dispenser Segway. Oh, not, not the best, not the best track record, but, uh, yeah,

Mike Gruen: 00:02:44

very eclectic inventor. Yeah.

Tim Winkler: 00:02:52

Um, cool. All right. Well, enough sauce, uh, sauce talk. Let's, let's give our listeners a preview of today's episode. So. This is going to be another episode, uh, in line with a recent mini series that we've been promoting around augmenting innovation from commercial tech into different areas of the government, like Department of Defense and different federal civilian agencies. And so today we want to discuss. You know, the talent transition from commercial products, uh, into maybe government services or government contracting or, uh, a consultancy that's supporting the government. So we'll explore what commercial technologists should know when they consider opportunities supporting, you know, like federal software projects. Uh, and then we'll also kind of like dissect some of the digital landscape across the federal software ecosystem, highlight what skill sets are trending maybe in 2023 and, uh, the government agencies that are kind of embracing this, this type of innovation. So, um, to unravel the subject, we've invited two guests with firsthand experience navigating the world of tech from modern GovTech environments. Uh, so we're joined by Alyssa Bookwalter, who's. departments for government agencies like the United States Digital Service, which is an agency launched almost 10 years ago to modernize government services and user experience. Uh, most recently has been helping scale out innovation labs and accelerators that are impacting, uh, the Department of Defense. And then alongside Alyssa, we have Brian Kroger. Brian, uh, I think it was like a, like a visionary in the defense tech industry, um, served as a captain in the United States Air Force. Um, Brian, you know, I've, I've read up on your, on your background as well. And you know, you saw this need for advanced tech in the military created Kessel Run, uh, as a precursor to your current venture rise eight. We'll touch on the Kessel Run story in our episode. I think it's got a lot of relevance to the topic. But RiseAid is a digital services company that helps customers in high compliance organizations like the government build and deploy software more efficiently. Alyssa and Brian, thank you both for joining us today. Thanks for having us.

Alissa Bookwalter: 00:05:01

Yeah, thank you. Excited to be here.

Tim Winkler: 00:05:03

Yeah, good stuff. Well, let's dive into two, um, I'm sorry, before we dive into the discussion. We can't, uh, skip over one of our favorite segments, which is pair me up. We'll all go around the room and shout out a complimentary pairing. Mike, you always start us off. So what, what do you got for us today? And I hope it doesn't suck because you already know, but

Mike Gruen: 00:05:24

now I have ketchup and mayo on my mind, but now I'm going to stick with my guns and I go with a change in optimism. I think they go pretty well together. I think there's a lot of people who look at change and get very like wound up about it and like, sort of see it as. Bad, um, and especially in engineering. I've seen that. So like, sort of just embracing that change happens. Change is good and being optimistic about it and trying to figure out what good can come from this change. So that's that's my pairing

Tim Winkler: 00:05:50

this time. Hey, that doesn't suck. I thought you were I thought you were prepping me for something really. I mean, I guess

Mike Gruen: 00:05:56

you're right. Expectations low and then surprise. That's that's Maybe that'll be, yeah,

Tim Winkler: 00:06:04

I like it, man. I like that. Everybody could use a, that type of outlook, uh, in today's world. So, um, good, good, good call. Um, all right, I'll, I'll go. Um, so this past weekend, my wife and I, uh, in our five month old baby now, and in our dog, we went for a, A Mother's Day getaway and, uh, went out into the mountains out near Charlottesville, uh, went on, uh, Alice's first hike, and something that my wife and I would always do when we go on hikes is touch, touch trees, uh, every so often. And for us, it was just something that, uh, kind of brings us into the moment. So something about being present, you know, being, being out there. Um, and, uh, uh, touching the tree while you're going for a hike. So mine is going hiking and touching trees. Uh, and, uh, that's, uh, we actually had, uh, the five month old, we put her hand on, on the tree and videotaped it. It was pretty, pretty adorable little moment. Um, but, um, yeah, big, big, big fan of being outdoors. So that one was, uh, uh, my pairing for today. Um, but let's go ahead and pass it along to our guests. Um, Alyssa, we'll actually start with you if you want to give us a quick intro and tell us your pairing.

Alissa Bookwalter: 00:07:18

Yeah. Hi, everyone. Um, I'm Alyssa. I spent, oh my gosh, about 10 years, um, first part of my career supporting military health. Um, did a lot of stuff with wounded, ill and injured, uh, military service members, veterans and their families, which is really cool. Um, and then I made the pivot into kind of civic tech and all things tech. Um, spend some time working as a federal civilian, like you said, at the digital service and then actually at Kessel Run. Um, and now I'm at a small nonprofit. I'm a chief talent officer, um, called the Griffith Institute. Um, fun stuff. I have three cats and two dogs and I live in Washington DC. Um, and this week my pairing is, um, Doggy Daycare and Usher. Um, that's a little bit probably off the wall, but, uh, my dog Leo goes to daycare and he absolutely loves it. And I get the pleasure of dropping them off most mornings. Um, One particular, I think it, I don't remember what day it was this week, but I was just kind of in my head. There was a lot of, you know, stress going on and I, I drop him off and I'm walking back to my car. And all of a sudden I hear, um, one of my favorite usher songs from back in the day, start blaring on the music. And I look back and I see my dog just jumping around and having fun. And I'm like, this is the most bizarre, surreal moment, but I like it. And it took me back and I'm going to have a damn good day. Um, so that's my pairing.

Tim Winkler: 00:08:46

Nice. Oh man, that's great. Um, that is a throwback as well. Is, do you have a favorite Usher song?

Alissa Bookwalter: 00:08:55

Um, I just, he's a good artist, but the song that was playing was, I don't know if you remember, it was, I think it was called Yeah. Um, it has little John or something, and I don't, I hadn't heard it in a hot minute, but here we go. Here we are.

Tim Winkler: 00:09:07

How did our producer know that our producer is sitting in chats over here saying, yeah, in all caps. I was like, that's, that's a scary, but he knew it somehow it is a, it is a popular song. So, all right, that might be the most random pairing we've ever had on the show. So that is a good. Nice. I like it. Love it. Awesome. Awesome background too. We're excited to, uh, dive deeper into that. So, um, cool. Well, Brian, how about yourself? Quick intro and, and your parent.

Bryon Kroger: 00:09:34

Yeah. So I'm Brian Kroger, CEO and founder of RISE 8. Prior to this, I spent 10 years active duty Air Force for seven years. I was a targeting intelligence officer on the last three years I founded a Kessel Run and served as a chief operations officer before getting out and starting RISE 8. My pairing, I've been traveling a ton, I've been on the road, conferences here in Tampa where I'm located, so it's just been hectic. Um, but I live on the water. Our office is on the water here. Uh, and we have, uh, uh, have a boat club membership. So whenever people come to town, I like to take them out on the boat. Since it's been so hectic, my pairing lately has been boat lunch. So we've been doing a lot of boat lunches. I just had some employees that were in town yesterday for some recording, took them on boat lunch. I think I've done like. I don't know, probably like six or seven boat launches this month. So, uh, boat launch, I will say though, um, I really liked Mike's, uh, one of my favorites, uh, things to pair is optimism and skepticism, skepticism. So I always refer to myself as an optimistic skeptic. And I feel like, uh, that's like part of the leadership OS to be a really good leader. You have to have optimism and skepticism. So cool. Love that one. Mike. Thank

Mike Gruen: 00:10:45

you. I like yours as well. That

Tim Winkler: 00:10:46

was pretty good. So I've, my buddy's on a, one of these boat subscriptions. Is it carefree boats? Is that freedom boat club, freedom boat club. Cool. And what kind of boat was a pontoon or you go on party barge for lunch or what's the, What's the boat of choice that you take these. Take these folks out on lunch. Tampa, Tampa's got a good setup.

Bryon Kroger: 00:11:08

There's actually like 16 locations you can rent from and they have like, you know, anywhere from like five to 20 boats each location here by our office though, has a lot of center consoles, um, deck boats. I've taken my kids tubing out here, uh, for this location. Um, yeah. And they had, they have pontoons too, if we've got a big crowd, but I usually grab like a center console with a, like two 50 on the back so we can just really all up the river and go get

Tim Winkler: 00:11:33

some lunch. Wow. So convenient too. You don't have to worry about trailer trailing it or anything like that. Good stuff. All right. Good round. I like that. Um, well let's, uh, let's, uh, transition and, and get into, uh, the meat of our discussion. So, um, again, we're going to be talking about transitioning from, you know, commercial into, into some of these government environments as a technologist. And just to clarify here, because a lot of our audience, you know, they don't have any understanding of a lot of, you know, government or defense or a lot of that lingo. Um, so I wanted to kind of, you know, start with by saying that there's differences between pursuing a role directly with a government agency and pursuing an opportunity with a company that supports the government, like a systems integrator or a tech consulting company or a pure product company. Um, and oftentimes these companies, if they're providing technical services to the government, then they, they might be referred to as a government contracting company, just some of the lingo. Um, and if we're spitting around acronyms throughout this, just kind of like spell it out, uh, cause I think that's always helpful and the government loves acronyms. Uh, so that, that will be helpful for the guests, but, um, let's start with, with you, Alyssa, um, you know, you've, you know, you've kind of run these talent, uh, teams and multiple environments. But you know, let's maybe start when you're recruiting talent at like the U. S. Digital service. Um, you know, what were some of the characteristics or traits that you were looking for? Um, when technologists, you know, we're joining and then we can jump to you, Brian and look at this from some other environments like a castle and rise eight such. But let's, let's kick that, kick it off with that.

Alissa Bookwalter: 00:13:18

Yeah, so I think, I think the foremost thing that, that I look for it, it, it's a personal thing, but it was also really based at the organizations that I worked for. Um, and whether that was on the government side or whether it was like a duty contracting side, um, you really want folks who are mission driven. Um, so you really want folks who are not in it for, you know, a paycheck or aren't necessarily in it to do the, the latest and greatest because. As we'll probably get into technology, the state of technology in the government is a lot different than in the private sector and moves a lot slower, right? Um, and so you have to have people that have grit, that have tenacity, that are willing to take on a challenge, um, and that, again, when days get hard, because they'll get really, really, really hard, you know, they're willing to kind of keep moving the needle, and maybe they thought the needle move was two miles, but it's a quarter of an inch, but that quarter of an inch will impact millions of people, or that quarter of an inch will like, you know, do something to save the warfighter, um, and that's pretty, You can't get that in the private sector. Um, and so I, I'd really start with that and that's, that's hard to find. That's, that's pretty hard to find.

Tim Winkler: 00:14:35

Yeah. Having somebody, especially, you know, if you're trying to recruit someone from the commercial space, um, and talk about compensations and today's market have just been crazy inflated in the last couple of years. And so when you, when you ask someone to trade off comp for the, for the mission, um, you really got to have a passion for that mission, uh, because you get used to a certain quality of life, you know, with a certain, you know, paycheck, um, and, uh, it might not always be that competitive in those types of environments. So, um, I think that's a great, a great, um, call out is, you know, really making sure that you're prioritizing the mission, um, if you're pursuing that opportunity. Brian, uh, let's jump, let's jump over to you real quick. And, uh, I'd love to hear angle on, on this side of it. Um, maybe from like rise eight, um, and, and Kessel run. But if you're open to it too, you know, um, I'd love for you to share your story with our audience on how Kessel run came to be. I think it's a, I think it's a powerful message, uh, on why there's. Such a need to push innovation forward in parts of the government specifically in defense. Um, so yeah, I'll pass it to you. Yeah, I love that, uh,

Bryon Kroger: 00:15:44

Alyssa hit on two really important things to me and my story. And I think the Kessel Run story, which are, um, you know, mission or I'll call it impact and then grit, um, grit's a really good word. And actually fun fact, uh, rise eight comes from the Japanese proverb, all seven times stand up eight or rise eight. Um, which is, uh, a quote that I stole from, uh, Angela Duckworth's book, uh, called Grit. So she said in there that if she were ever to get a tattoo, she would get a tattoo that said Fall 7, Rise 8. Uh, in honor of that Japanese proverb, which is, uh, a story of transformation, right? So if you fall seven times, you would stand up seven times. So fall seven, rise eight is about standing up greater than when you fell. So, um, grit is what it takes to do that. And especially in the government space. Um, that's, uh, you know, going to, to my story, I said, I started as an intelligence officer seven years doing primarily targeting operations. And, um, I, I didn't know much about the air force, especially intelligence when I joined. So, you know, when you hear you're going to be an intelligence officer, you're coming out of college. Like I didn't do ROTC or anything, so I had no insight. I just applied and I got selected to be an intelligence officer. And I thought I was going to go do some Bourne stuff, right? Like, oh, Jason Bourne. I didn't actually think that, but you like have these expectations that like, Hey man, you're going to have this great technology. There's going to be like. You know, you minority report, whatever, pick your favorite movie of like holograms and cool technology. And I show up and it like takes me two hours to log into my email. Right. And so, um, I spent seven years using really bad software to conduct the most critical missions on the planet. Um, and, uh, you know, the, the, whether you're talking about the battlefield or, you know, providing veterans care at a VA hospital or all the crazy, awesome missions that you can do inside of the federal government. Um, the world around us is operating at digital speed, right? Machine speed and in the D. O. D. We have the most advanced hardware on the planet. Uh, but oftentimes we're conducting those missions with software that doesn't work or is forcing us to operate at human speed when we need to be operating at machine speed. So I just saw really terrible things happen. Um, you know, everything from. You know, whether it's civilian casualties, troops in contact that we can't support soldiers, you know, getting hurt or bad guys getting away. Like, I've seen it all and, uh, like, software is a big differentiator there from my point of view. And, um, after seeing a particularly bad incident, I actually requested to transfer from targeting to acquisitions, which nobody does. I'd like the coolest job. And then went to like, sorry to say it, people might take issue, but like didn't want to go be a procurement person. Let's just put it that way. The day that I showed up, uh, I called D. I. U. defense innovation unit. It was actually X at that time. Experimental, um, got put in touch with Colonel Enrique and we started, uh, what would then become Kessel run? Um, and, uh, later joined by our 3rd co founder, uh, Lieutenant Colonel Jeremiah Sanders or Colonel Sanders. Uh, yeah. And, um, and then, yeah, Kessel Run became, I would say, inarguably the, the largest and most successful digital transformation in federal government. Um, we pioneered a lot of different things, like being able to continuously deliver your software to a production environment, which I think in commercial we take it, uh, for granted. But, um, Kessel Run was one of the first organizations to establish that and in doing so was able to continuously deploy software to end users out in the field, um, iterate based on their user feedback, uh, which, you know, contributed not only to really great mission outcomes, but going to what we're here to talk about today, the talent at Kessel Run, we're able to attract unbelievable talent because not only did we have that mission, but you actually got to see the impacts of your work in real time, which is pretty rare in government. Thank you.

Tim Winkler: 00:19:33

Yeah, I love the story. Um, I, I, I love how it kind of comes full circle for you. And, uh, you know, as an entrepreneur, um, you know, was this kind of like your Your step into it, you know, um, you know, did, did you have anything prior to military that you started anything on your own or was, was this kind of like your foundation for, you know, pursuing your own thing at rise eight? Yeah. I mean,

Bryon Kroger: 00:19:58

I think I probably stepped out on my own a lot, uh, throughout my career. But nothing ever really like entrepreneurial, maybe like an entrepreneur inside the military. But, um, I think for me, I wanted to continue achieving that, like, same level of impact in the military kind of makes it hard from a talent management perspective as a uniformed military member. Like, I was a captain, so I was fairly junior. Kessel room grew very quickly to the point that it was now like the size of an organization that would be taken on by a colonel, right? Several ranks where I was. So, um, for me, getting out seemed like a natural choice of being able to continue to achieve the same level of impact and also. In technical terms, we talk a lot about scaling horizontally versus, uh, vertically. Um, I could keep going and doing like, uh, vertical scaling, like go to the next program and do something cool and go to the next one, but at rise eight, I get to go all across the federal government and help everyone. So that's been kind of, that's what drove me, not necessarily anything entrepreneurial, but just wanting to continue to grow the

Tim Winkler: 00:20:59

impact. Got it. Yeah, that's cool. And I want to dive deeper into that, um, those skill sets at rise eight and how you kind of evaluate talent and how to kind of prep that, but before we do, and I think it's just kind of a little bit of an ironic coincidence, but, um, Alyssa, you also, you know, had a, uh, a role at Kessel run. Um, you know, uh, can you maybe explain on what that looked like? And then, you know, just maybe speaking to from a talent perspective, you know, piggybacking on what Brian was alluding to.

Alissa Bookwalter: 00:21:30

Yeah, um, so I was a chief of staff at Kessler Run for the all domain common platform. Um, it's one of the product lines and, you know, one of a big component of my job was finding, finding our talent. Right? So who is going to sit in the product line? Where are we going to get the technologists? Um, you know, and we had a phenomenal, they still do a phenomenal chief people officer. Um, but it's really thinking outside of the box because not only do you have this phenomenal mission driven organization that really is, was, is the first of its kind in the DoD and has been replicated, I think, like 25 more times now or something, right? Um, but you have a very competitive market with salaries. Um, so Kessel Run really led the way on things like remote work, right? Like, we can have distributed teams and we can make you feel part of our culture. Um, Kessel Run had a phenomenal, like a two week boot camp to its culture, right? And you heard from every single part of the organization and, you know, how you were part of a mission and how you fit and where Kessel Run fit into the larger scheme and the impact that you were making. Um, seeing it in live time is... Is absolutely real. Um, and then one of the things that I did, um, just because I love collaboration and I love partnerships. What? And I had a phenomenal, um. Boss that let me, you know, like go for it, run with it is I, I brought in a lot of partnerships. Um, so we brought over a detail from the U S digital service and he actually, um, decided to stay on at Kessel Run, which is really, really cool. He loved the mission so much. Um, we worked with the national security innovation network for, um, specific talent needs that, you know, we could go out and recruit for, but maybe we're having some trouble. They had a huge, you know, newsletter and they had a reach. Um, so we worked with them a little bit. Kessel Run does engagement days. I think they actually have one coming up for any listener that's interested. And it just talks about what they do in the culture. Um, and again, you have to make an effort with talent, right? A lot of government organizations and, and DoD contractors to an extent don't. And you really have to tie the impact and the effort. And this is what you're going to be doing in real time results. Um, and it's just, it's a, it's refreshing and it's a breath of fresh air. And I, I really loved what I did there.

Mike Gruen: 00:23:54

It's cool. Yeah. I just want to jump in on the whole mission thing. Cause I, one of the things that in my background, I've done a lot of things, government contracting off and on and private, when people ask me like what, what projects I worked on that like really still stand out to me, the one that almost always comes top of mind is, uh, I worked on a software product that was supporting, um, HSTC, which is human smuggling and trafficking. And like, just working with those guys and seeing their mission and knowing that, like, what I'm working on is having a real impact in the world and stuff like that. That's the type of stuff. And, uh, you know, that was, uh, over 10 years ago that I worked on that and it's still top of mind in terms of one of the best projects I've worked on and knowing that I had that impact, even whatever small middle skill part I played in that. Um, and I do agree with like, everything you guys are saying about like mission and the trade offs of technology. But I also think 1 of the things that I'm curious, you know, Alyssa, um, and Brian. You're solving really hard technical problems. You might not have the best software or the best whatever, but in the end, at least I found that some of the most challenging projects I was working on were actually government, the ones where I was doing government contracting. Um, some of those, especially in the Intel community and in DoD, where some of the most challenging sort of intellectual projects, um, and very rewarding from that perspective as well. I'm curious if you guys, if that's sort of been your experience as well. Brian, maybe start with you.

Bryon Kroger: 00:25:17

Yeah, I mean, that's uh, I'm biased. It's like all I want on it. You're exactly that. So, yeah, um, I find it extraordinarily meaningful. I mean, where else can you achieve? Like these, these levels of impact, I know, um, I'll use the first application at Kessel Run. And by the way, we actually got to use the coolest latest technology, which isn't always going to be the case in government. So I want to caveat that. If you're looking to get into government, you might be in more difficult spaces.

Mike Gruen: 00:25:43

People would be surprised to find out that that's still like, I think people have this idea that they're not going to be able to do that. But I was, and I was surprised at how often I got to play with like some cutting edge stuff. So I'm sorry,

Bryon Kroger: 00:25:54

I'm like, really cool missions. The 1st application that, um, it actually was like the precursor to Kessel Run. Uh, we ended up adopting the app. It was called jigsaws, a tanker planner application to do air to air refueling. So like when we're planning, uh, missions overseas in particular, um, we're conducting air operations, we refuel planes in midair. And, uh, it's a combinatorial data problem. Like it's a huge, massive number of combinatorial options because you've got not just American aircraft, but you've got coalition aircraft. They have different attachment points, different types of fuel, they're flying different caps. So like, and there's all sorts of rules like this coalition partner won't refuel from this coalition partner. They like us, but they don't like each other. And so it's a really cool data science, uh, data engineering problem. Um, but the initial application, we actually didn't even have to do any of that. Like it was pretty, you know, like standard linear algebra to get to the first MVP where. Uh, we, uh, made that tanker planning process so much more efficient. They were able to say on save on average 1 tanker per day, which equates to about 214, 000 dollars a day in fuel savings. So, the application paid for itself in a week. We had spent like 1 and a half million to get to MVP. Um, but if you multiply that out for say five years, um, I have to check my mouth. It's been a while since I've quoted this stat, but I think it's 391 million in fuel savings. Where can you have that level of impact? Like this, this was a team of like a product manager, a product designer, and four software developers. And they built in 120 days and shipped to production and application that over the course of 5 years will save the DOD 391 million in fuel savings. That's just the initial iteration. They went on to actually save 2 tankers per day, started to implement algorithms that make the planning process more efficient so that we need less planners, so there's troops that don't have to deploy overseas. I mean, just like crazy impacts. Uh, that you can have, like, where else can you do that? I always joke, like you walk down the street in San Francisco and there's an ad for a job to go work on a, you know, app that helps you optimize your dog walking routes. So you can find places for your dog to pee. It's like, it's

Mike Gruen: 00:28:11

San Francisco. Uh, it doesn't really

Bryon Kroger: 00:28:14

matter.

Tim Winkler: 00:28:17

But the, the reality here though, is that there is some, some pretty big misconceptions, I'd say, uh, some common misconceptions about, uh, a lack of innovation or, you know, just so much red tape and, uh, it's, it's really tough to, to innovate or, or ship, you know, quickly, um, you know, what, what are some of the ones that, uh, are there any others that you've heard of, or, or, you know, what, how would you. Combat those, some of those misconceptions or, or how would you say that, you know, that could be true, but, you know, maybe navigating these types of opportunities or with these types of, on these types of projects.

Alissa Bookwalter: 00:28:56

Yeah, so from my end, I think we like to call it bureaucracy hacking and I think that's a pretty, a pretty standard term these days. What I would say one of the misconceptions is what you alluded to it's that there's so much red tape and there's so much bureaucracy and there's people standing in the way that aren't willing to change or, you know, clinging on to antiquated processes or policies or regs and they don't want to move and that's actually a lot of the times not the case. Um, it could be education. It could be misinformation. It could be someone quoting some regular policy that like they've been told and guess what regular policy doesn't actually have that or maybe it actually hasn't had a legal interpretation and you can actually do something really cool and move fast. It's building relationships. I mean, whether you're on the government side or the government contracting side, right? Having stakeholders trust you and work with you and valuing. Their input and their expertise, and they're probably most oftentimes decades of federal service is really important. Um, and then potentially pivoting and showing them a better approach, right? I don't think a lot of us are here to kind of come in and make a buck and leave, right? And kind of go out and then IG gets involved and it's millions of dollars in a system that doesn't work, right? Um, but it's, it's changing that. And there's a lot of innovative people and processes in the government. And it's actually a really exciting time to be either in it or supporting it, because I think we're on a, like a huge change and it's really cool. It's been a great thing to be a part of.

Bryon Kroger: 00:30:40

Yeah, I agree with that. Uh, finding an organization that's hacked the bureaucracy already is like a really powerful thing to look out for. Fact, actually. bookshelf, hack your bureaucracy by Nick Sinai has great stories of people hacking bureaucracy and GovTech. Um, uh, Marina, uh, was the other coauthor there. Um, but, uh, the other thing is if you're going to come into a space, uh, you know, we get a lot of people that come even out of the Silicon Valley, like presidential innovation fellows, us digital service, and they come in with these like high hopes. They're going to bring their technical talents. Like your technical talent is irrelevant until you hack the bureaucracy. And so like, first and foremost, you have to be a bureaucracy hacker and you can't hack systems. You don't understand. So, like, if you want to take this leap, you know, 1 option is to join an organization like Kessel Run or similar that's already hacked the bureaucracy, or you can go into a new space that you're passionate about. Maybe it's like the VA. Actually, they're very innovative too, but. Maybe you go in there, you have to now become the bureaucracy actor. You've got to go study the policies and the regs and figure out how to work around them. I can guarantee you that there are ways to do all of this. We didn't break any rules to start Kessel Run, believe it or not, or to do anything that we did. We never had to violate a policy or even ask for an exception to one. Um, My, my friend, uh, Dan Ward, uh, he was prior Air Force, but, uh, now does a lot of government consulting. He says that, uh, ignorance of the FAR, that's the Federal Acquisition Regulation, or I'll just say rules. Ignorance of the rules is a far greater barrier to innovation than the rules themselves. And I think that, like, stands to reason that if you're going to come into an organization, even if it's not government, a large enterprise that has bureaucracy, Like figuring out that bureaucracy and then hacking it is the first step.

Tim Winkler: 00:32:29

Yeah, I think that's well said. And, you know, somebody who's kind of seen it from a couple of sides, right? So when we first started hatch, you know, we, you know, based out of the DC area, a lot of the work we were doing was, was helping, you know, government contractors, these smaller kind of. Eight a, uh, companies that were winning work. Um, and then we ended up transitioning into, you know, commercial startup land. And one of the interesting things was, um, you know, we saw this bias from a lot of the, uh, CTOs or the founders. That they didn't really want to see technologists coming from systems integrators. Um, they wanted to see technologists that came from very specific, you know, product environments that maybe we're at a certain phase in the product lifecycle versus maybe somebody who had been building, uh, you know, a larger system for DHS or something along those lines. And I think, you know, that has changed, um, you know, uh, in the last few years. But, um, the other interesting change that we're seeing and part of the reason the catalyst for, for creating some of this media. Is because there is more interest in commercial technologists pursuing opportunities in, in these industries and in the government than there ever has been before that we're seeing, which is wild. I think one of it is as a, as a result of the economy and the market, you know, it's just timing right now with, um, you know, funding being really challenging to come by for, for commercial startups in early stages. And there's much more stability, uh, when you think about, you know, going and working with, um, in the government space on maybe a project that maybe is a little, a larger transformation, but that also means maybe it's a three year or four year type of project. And, you know, you might have a little bit more job stability than you do when your runway just, you know, kick the can after six months and start up world. So it's an interesting trans transition point. And that's why I think it's important to kind of continue to build. Uh, this this type of information for those folks to to navigate, because I think you put you brought a really good point, Alyssa, about, um, um, maybe it was Brian, but the relationships that you're building, um, you know, with these stakeholders, and there's something really unique, powerful about going and attending some of these conferences, uh, where folks are, you know, really engaging and, uh, you make make great connections and good relationships. And And oftentimes it's just like standard networking, you know, but that's, that's how you can try to get your foot in the door, um, through, through some of those types of events. Brian, I wanted to ask about rise eight in terms of like, you know, some of the types of folks that you're hiring for. Um, and you know, what are those skill sets that you're, you know, that you're going to say is, you know, uh, transformative or, or really progressive right now that you're, that you're trying to tap into? Yeah, so, uh,

Bryon Kroger: 00:35:32

we do, first of all, we do elite software development for mission critical systems, right? Those are, that's our focus area. And I say elite, like, we're high end software development shop. We do custom software development. We don't do proprietary products. And I believe that the government should own their products. Um, with that, we often find ourselves environments, uh, we use this to build Kessel Run, who's pairing, love naming the podcast, but we're an XP shop, so we do 100% pair programming. We also do pair product management and product design, so sometimes the government might hire us to come in and just deliver an application, but more often than not, we're coming in and pairing with the government to build products and upscale them at the same time. I think that that's, uh, a trend that I see growing in the federal government right now. And so skills that I look for as I'm trying to hire people, um, not only like technical excellence. Uh, but to be able to pair with somebody for eight hours a day, especially somebody who's not like on your team and part of your culture, somebody that you're trying to transform or change, um, not only upskill their talents, but you're also trying to change their culture and work through their cultural inefficiencies and bureaucracies. It takes a lot of soft skills, um, which are actually the new hard skills. So honestly, like I'm looking for engineers, um, that are excellent communicators that have high empathy. Um, that are able to pair program effectively, which we have a way to assess that. Um, so I'm looking less right now, like hot skills, like, oh, yeah, I need a, you know, prompt engineer. Um, I'm looking more at how do I find those unicorn engineers who are also incredible. Uh, communicators, empathizers, upskillers, coaches, um, so that that's really our focus. I would say that's somewhat unique in the space still, but I see it as a growing trend. And if you want to be in this space, I think, uh, having those skills is really important. Even if you are going to go direct into government as a technologist. You're probably going to have four or five people on your team who are nowhere near your level. So being able to do something like pair programming or pair design, uh, with them is, is I think a really valuable skill set to create change.

Tim Winkler: 00:37:44

That's fascinating. You can't snuff that out with the coding challenge. Um, that seems like that's a little bit more of a, you know, human, human, uh, conversation right there. Alyssa, what about you? And, you know, I'm, I'm curious on, you know, the work that you're doing at the Griffiss Institute. Um, you know, what, what is it that you think is so mission driven about this and how is it transforming, you know, how technology is being built in defense? Yeah, well,

Alissa Bookwalter: 00:38:11

the fun thing about where I'm at right now, specifically what I get to do with our division is our division supports, um, Department of Defense, mostly for the Air Force, um, internship programs. So, we are really taking The next generation of technologists with an end goal of getting them real world experience, getting them to work with mentors who are federal employees or defense industrial based employees and getting them interested in it, um, getting them scholarship money. Right? And then at the end, hopefully they'll have an interest in. Joining federal service or going to the defense industrial base or becoming an entrepreneur and supporting defense, right? All of it is a win and those things that I hear Brian talk about that holistic picture of not only the technical chops, but the all around, you know, nice person, engage with stakeholders, educate people in a way the people skills. Um, Are what we're doing with the interns, right? So they, they come on and they have their projects and their mentors, but they also have classes on leadership and development and all of this really good stuff that makes a killer, well rounded employee, whatever they decide to do. And so it's just really great to see that the pipeline, especially for the DoD is headed in the right direction. Right. Um, because I do, I think that's the future of work, right. And especially in the technical space, whether you're in the government side or the government contracting side or wherever. Yeah.

Tim Winkler: 00:39:47

Yeah. Well said. Um, yeah, so we only have a couple more minutes, uh, left, uh, before we transitioned to the, the last segment here, but. Um, you know, just generally speaking, uh, other, other, um, like any agencies, um, or specific, uh, resources that you would direct folks to, uh, it could be conferences, it could be things of that nature. That maybe is a good starting point, um, for folks that are looking to, you know, learn more or, or get a little bit more entrenched and meet, meet some folks that can be beneficial as a technologist. Absolutely.

Bryon Kroger: 00:40:25

I think, um, 1 just happened code for America, uh, summit, uh, code for America is a great organization. Um, the name speaks for itself. I think, uh, really great mission, mission oriented folks. They don't play as much in the D. O. D. Space. Um, it's mostly like federal state, local agencies. Um, really great crew amazing networking. You hear the craziest stories. Um, it's hard to walk away from there and not want to go work for government. And then, you know, the illicit part of this group, but like anything that stemmed out of the U S digital service kind of, um, title wave that came through. So there was defense digital service, there's 18 F and the technology transformation services within the general services administration. Um, 18 F had some of the most incredible people from Silicon Valley that came work for it. A lot of people might know Jess Humble. He was like one of the people that really inspired me to build a continuous ATO based on the work they did at, uh, 18F building cloud. gov. Um, so there's all sorts of really cool use cases. And then the DoD software factories, they're like very vocal and active on like LinkedIn and other social media. So, um, and lots of like recorded videos and they participate in conferences, uh, like, you know, they were just at KubeCon and, uh, you know, they're just out there everywhere. You can find them. Um, so follow them on social media and, and, uh, 18 F in particular has a bunch of playbooks. So it's a really, in fact, a lot of them are used by commercial organizations. They're like taking them back out of government and like, Oh, let's use this at our commercial org. So, uh, definitely worth checking out their website and some of the things they have going on. And then plug, just because they're one of our, my favorite, like current customers, the VA, uh, just cause I'm a veteran and, uh, I think the mission is so cool. Um, but the VA is really forward leaning in. Uh, organization. I think, you know, hearing what's been on the news over the last several years, I mean, they've taken a rough, uh, beating in, in the public space just because of some of the inadequacies of veteran care. Mm-hmm. a lot of that's like policy and government. When you step inside, like V A I t, like those are mission oriented people working their butts off. They're super innovative, they're doing cool things. I'm like very impressed and humbled by what they do.

Tim Winkler: 00:42:48

That's awesome. Alyssa, anything you'd like to add to that?

Alissa Bookwalter: 00:42:52

You know, I think, I think Brian hit on a lot of the organizations. I mean, that, that, that covers the gamut and he's, he's spot on. Um, the, another conference is the Grace Hopper Conference. Um, that's a, that's a really great innovative one for especially, um, diversity in tech or gov civic tech, gov tech, whatever you, whatever your spiel is. Um, and I, I want a second rep for the VA. Um, so we, when I was at USPS, we, you know, we had a digital service team there and they've built out a whole huge organization. Um, from that, but really, really transformed care for veterans. And my husband's a disabled veteran and uses their services. And it's, it's like night and day from, you know, a couple of years ago. So I want to, I want to second their efforts. That's really cool.

Tim Winkler: 00:43:46

That's great. I like this is, these are different than some of the other ones that we received from previous episode, like, um, like DARPA and, uh, Johns Hopkins, uh, applied physics lab and have Ryan shake his head. Um, well, I think, um, I think this is, uh, this is a great, uh, educational piece. Um, I know it's, it's certainly going to be useful. Um, I want to spend the last 10 minutes here, uh, on a fun segment, uh, that we'll transition to called the five second scramble. Um, so this is a, a quick hit kind of Q and a, uh, I'll ask each of you a series of questions. Uh, try to give me your response within, within five seconds. Um, some, some are business, some are, are personal. Um, I'll go ahead and start with you, Brian. Um, we'll kick it off here. So what, what is your, your favorite aspect of working at rise? Eight? Uh,

Bryon Kroger: 00:44:43

pairing. I love pairing with government, um, rather than just delivering things. So I love when we get to pair and help upskill

Tim Winkler: 00:44:51

people. Oh, you'd love the pair program. I appreciate that plug. What, uh, what would you describe as your favorite piece of your culture?

Bryon Kroger: 00:45:01

Uh, Growth mindset. I think, um, this idea that everything has to revolve around learning, uh, this is a learning journey. Think, um, you know, not having the right answer up front, not having to try to plan and, you know, coming out of government. We try to predict the future, stop trying to predict the future and start trying to find the future, uh, through iterative product development, iterative learning.

Tim Winkler: 00:45:29

Nice. You might've answered this question earlier in the episode, but what, what kind of technologist thrives at, at rise eight? Hmm. Uh, let me

Bryon Kroger: 00:45:39

just, well, having a growth mindset is a big one. I think grit is another big one. Um, you know, outside of all those soft skills, like you have to have great, if you're going to work in the government tech space, uh, grit being defined as passion and perseverance.

Tim Winkler: 00:45:54

Nice. What can folks be most excited about for Rise 8 in 2023?

Bryon Kroger: 00:46:01

More mission impact, uh, we just keep growing and keep producing more outcomes in production.

Tim Winkler: 00:46:07

Do you have a favorite book or podcast on leadership? Uh,

Bryon Kroger: 00:46:14

I read a ton of books and I always rattle off a bunch, so I'll just go with my most recent. My favorite, like, most recent read, um, was Farther, uh, Faster Earth, Far Less Drama by Jason and Janice Frazier, who are actually... Two mentors of mine at Pivotal Labs when we started Kessel Run.

Tim Winkler: 00:46:32

What do you love most about yourself? It's awkward.

Bryon Kroger: 00:46:39

That I'm humble. You know, uh, I. I guess maybe like most proud of, uh, you know, being a father of four and still being able to do this whole entrepreneur thing.

Tim Winkler: 00:46:56

That's awesome. Yeah. We need to have you on it for a second episode about parenting and entrepreneurship. Uh, it's, it's something that's top of mind for me. So, um, What, uh, what's the most, um, I'm sorry. What's the worst fashion trend that you've ever followed? You

Bryon Kroger: 00:47:16

remember those like t shirts for your feet? It was like ugly Nikes. I don't remember what they were called.

Tim Winkler: 00:47:23

T shirts for your feet, though. I got to Google this now. T shirts for your feet. Wow. All right. We'll accept that. Um, what, uh, Oh, if you could have dinner with any historical figure, who would it be? And why, uh,

Bryon Kroger: 00:47:40

Marcus Aurelius? Cause I wish I was more stoic.

Tim Winkler: 00:47:43

Nice. What is a charity or corporate philanthropy that's near and dear to you?

Bryon Kroger: 00:47:50

Uh, the wounded warrior project's a big one, but like all things related to veteran, veteran care being veterans, you know, off the streets and away from suicide.

Tim Winkler: 00:48:02

What is one skill or hobby that you've always wanted to learn, but you haven't had the chance to yet?

Bryon Kroger: 00:48:17

I don't know that I have one. I do all the things I want.

Tim Winkler: 00:48:21

I love what I do. You can get back to us on that. Um, What if you could have a personal theme song that played every time you entered a room, what song would you choose? Uh,

Bryon Kroger: 00:48:34

Rise Up from

Tim Winkler: 00:48:34

the Hamilton soundtrack. Oh, cool. And then last question, what, who is the greatest superhero of all time? Uh,

Bryon Kroger: 00:48:45

I'm partial to Superman, the cliche answer, but that's it for me.

Tim Winkler: 00:48:51

All right. All right. That's it. You, uh, you nailed it. You nailed it. We still, we're still going to need that answer from, uh, the, the skill or hobby. We'll, we'll, we'll wait for that, uh, uh, at another time, but, uh, well done, uh, Alyssa, are you, uh, are you ready? Hope you weren't taking notes. Cause none of these questions. I wasn't

Alissa Bookwalter: 00:49:09

taking notes, but those were intense. So, all right, let's see what you got.

Tim Winkler: 00:49:13

Okay. All right, let's go. Um, explain, uh, Griffis Institute to me as if I were a five year old.

Alissa Bookwalter: 00:49:20

Sure, Talent and Technology Accelerator, if you like Star Wars, like running around with forks on your shoulders, being able to use lightsabers, aka pool noodles to demonstrate really, really cool things with cybersecurity and science, you would love the Griffiss Institute.

Tim Winkler: 00:49:41

That's perfect. So I'm going to apply tomorrow. Um, what, what is your, your favorite part, uh, about the culture at Griffith Institute? I love

Alissa Bookwalter: 00:49:56

laughing and a sense of humor. Um, I have, I have a wicked sense of humor, whether People like it or not. Um, and most of my colleagues share the same. So I'm, I'm going to go with that.

Tim Winkler: 00:50:08

Nice. What would you say is a company value that is important to you?

Alissa Bookwalter: 00:50:13

Yeah. Psychological safety. Um, it's, it's really important that everybody has psychological safety to speak their mind, to disagree on things, but commit. Um, and a safe space to, you know, show up authentically for who you are. Um, and that's really important for me, wherever I go.

Tim Winkler: 00:50:35

Do you have a favorite book or podcast on technology? Oh,

Alissa Bookwalter: 00:50:42

um, you know, it's not technology specific, but the last really amazing book I read, I was a little slow with hack your, hack your bureaucracy. I mean, we just, we did hack the bureaucracy. It. It was spot on and I needed, I needed that inspiration and I hate to shout it out a second time, but that was, that was so good. And it's, it's so much more than technology, though. It has a lot of really good, um, examples for

Tim Winkler: 00:51:09

it in government. I feel like we're just running a, a promo ad here, uh, for, for the book, uh, about seeing influx in, uh, and sales. Um, what is, um, I'm sorry. Who is your biggest role model and why do they inspire you? Oh,

Alissa Bookwalter: 00:51:27

good one. Um, I have a lot of, um, amazing people, but it was a, a former coworker, um, who actually now works as a contractor at Kessel Run. Um, and she's a retired O5, um, military psych nurse. And I worked with her when I was supporting, um, wounded, ill and injured soldiers at Walter Reed. And she just really, she inspires me. She lets me be myself. She, you know, gives me some good life lessons, but she's also one of my biggest superfans. Um, so Mary, if you're listening, thank you.

Tim Winkler: 00:52:14

Nice. What is a charity or a corporate philanthropy that's near and dear to you?

Alissa Bookwalter: 00:52:20

You know, I, I hate to sound redundant, but anything veteran related. Um, I, when I was on the government side, I. Help stand up a new initiative for military spouses and families who worked or wanted to work in federal service. Um, and it's, it's life changing with employment just in general, um, for military families. Um, and I got to do a lot of cool stuff with that. I got to talk to a lot of military families firsthand and, uh, it's something that drives me and I'm always inspired by.

Tim Winkler: 00:52:53

Awesome. A lighthearted transition here. What is your favorite cereal? Um,

Alissa Bookwalter: 00:53:01

Honey Nut

Tim Winkler: 00:53:02

Cheerios. Classic. If you could live in a fictional world, from a book or a movie, which one would you choose?

Alissa Bookwalter: 00:53:11

Uh, Harry Potter. Hogwarts. Um, all the way. All the way. Huge Harry Potter super fan. Have Hogwarts legacy.

Tim Winkler: 00:53:20

Nice. Have you been, uh, to, to the, um, spot in Disney, the Harry

Alissa Bookwalter: 00:53:25

Potter? It's actually at Universal and yes, I have, um, several times. It's pretty amazing.

Tim Winkler: 00:53:32

I stand corrected. I have not been, obviously, so, um. Now you know how it feels, Tim,

Bryon Kroger: 00:53:36

when,

Tim Winkler: 00:53:40

there. Do you have a celebrity doppelganger?

Alissa Bookwalter: 00:53:44

You know, I don't think I do. Um, yeah, I, I don't, unfortunately.

Tim Winkler: 00:53:50

Okay. I don't think that's unfortunate. Do you have any phobias or irrational fears?

Alissa Bookwalter: 00:53:56

Um, I, a little bit. I generally have to like psych myself up and talk myself up off the ledge mentally when I'm going to do anything with heights, but I do it because I think life's not a journey and I do what I want to do. Um, but it's always a little bit of a struggle getting there.

Tim Winkler: 00:54:16

If you could have any superpower, what would it be? Um,

Alissa Bookwalter: 00:54:21

probably being like 90 places at one time, because there's a lot of things that I like to do and I can't hit the ball generally.

Tim Winkler: 00:54:29

Nice. And then we'll close with, uh, your favorite Disney character. Hmm. Hmm. That's hard. Um, and we're encompassing like modern Disney too. So everything, um,

Alissa Bookwalter: 00:54:56

Can I just uh, it's not Disney, but I'm just gonna go with Harry Potter and Hermione Because I think she's pretty cool. Sorry, it's not Disney specific, but we'll keep the Harry Potter theme

Tim Winkler: 00:55:10

We'll accept it. Cool. That's a wrap This has been a lot of fun. Thank you both for joining us and tackling a topic that is important It's very Uh, in our industry anyways, it's, it's very front and center. Uh, so I appreciate you all sharing some knowledge on it and, uh, joining us on, on the Pair Program. Thank you. Thanks.