Stepping Into the Unknown: Ross O’Rourke’s Rise to CEO

Ross O’Rourke didn’t set out to run a company. Like many in national security, he followed the openings in front of him and said yes to things he wasn’t sure he could pull off. The technical work came first. The leadership came later, once he could see where both the mission and the market were going.

On this episode of “Rookies to Rockstars,” hosts Amanda Ziadeh and Camille Tuutti talk with O’Rourke about building Crimson Phoenix, what it actually takes to scale a mission-driven company and how he leads in today’s national security environment.

He shares lessons from pivotal career moments, the importance of surrounding yourself with the right people, and how he approaches risk, innovation and culture. O’Rourke also reflects on the mentors and experiences that shaped his leadership style, and why staying grounded in purpose continues to guide his decisions.

From early-career uncertainty to leading a growing organization, O’Rourke’s story is a reminder that success isn’t always linear, but it is intentional.

Transcript

SPEAKER_00 0:00

There's a couple of mistakes I've made that really stuck with me. One is I misplaced a rocket when I was in Iraq. And uh that uh we were we were just sleep deprived and moving from house to house, and we had a minute to take our gear off, and like I left that thing in a house. And who knows if a bad guy made a bomb with that in the future.

SPEAKER_02 0:25

GovCon has a language of its own. Acronyms, compliance, acquisition. And when you're new, it can feel a little bit like alphabet soup.

SPEAKER_01 0:32

And let's be honest, no one hands you the codering. We are your host, Mill Toodie and Amanda Zed. And we are here to get real about how people actually break in, level up, and leave.

SPEAKER_02 0:42

Because not everyone grows up dreaming about GovCon. Some people just need a way out of a small Ohio town and end up in the industry by way of Fallujah.

SPEAKER_01 0:50

Today's guest enlisted in the Marines at 18 shipped out during the Iraq War. And his unit ended up as the main effort of the assault on Fallujah. GovCon came thereafter, and it turned out to be the right fit.

SPEAKER_02 1:04

Yeah, and along the way, he packed 21 books into his marine bag, worked 40 out of 52 weekends for two straight years, and built the skills to eventually buy a company.

SPEAKER_01 1:14

Now he's the CEO of Crimson Phoenix, and he has a lot to say about work ethic, what it really takes to climb, and why your leader's ceiling might just become yours. All right, let's get into it. Hi everyone, and welcome back to Rookies to Rockstars, the series where we ask bold, smart people one thing what do you know now that you wish someone had told you on day one?

SPEAKER_02 1:39

We're your hosts, Amanda Zieda and Camille Tootie. And today we're talking with Ross Orwick, CEO at Crimson Phoenix. Welcome, Ross. We're really glad that you're here with us today.

SPEAKER_00 1:48

Thank you. Happy to be here, ladies.

SPEAKER_01 1:51

Ross, we met recently when I interviewed you for a profile. So I already know a little bit about your origin story. Always, always. So that's right. You grew up in Ohio, one town over from JD Vance. That's the town's claim to fame. What was life actually like there?

SPEAKER_00 2:09

Okay, so yeah, I have a bit of a humble beginnings background in story. And I think just like many like rural and suburban places all over America, we just grew up what we thought was just a normal life. But getting out into bigger cities and the real world, you just realize how simple and really uneducated in some ways and underdeveloped, and you know how how really really simple things are back there. But yeah, it was it was poor. It's in the rust belt of Ohio, Indiana, Michigan, kind of Kentucky, Tennessee, Appalachian Rust Belt, I think it's referred to. And yeah, you know, there's not a whole lot of economic drivers in the area. So there's factory jobs and um a little bit of industry, but not a bunch going on. So things were tight in my family, and at times we were on welfare and food stamps, not for long, but you know, there were periods where we struggled. And uh where we grew up, common to see meth attics at gas stations that would not be unheard of. So so yeah, that's kind of an origin story, but there's also Midwestern charm here and there and just wonderful, loving, God-loving people that would give you the shirt off their back. So it's not all doom and gloom, but you know, there certainly wasn't a whole lot of privilege growing up. And yeah, JD Vance's book, Hillbilly Elegy, was an awesome account of what it's like to grow up in that area. And I could have copied and pasted quite a few things from his story to mine.

SPEAKER_01 4:02

I have met the best people from Ohio, they are usually the nicest, most solid people. So I I know quite a few of them. So you joined the or you enlisted in the Marines as a way out. Did you have any idea what you were signing up for?

SPEAKER_00 4:20

Yeah, to your uh last point, in Ohio, there's not much going on, so it's more about who you're with rather than you know what you have. So there are awesome people there. So yeah, uh enlisted in the Marines to kind of have a way out, frankly. And it was in 2003 after the 9-11 incidents, and we were pretty much at war in Iraq, and there's a sense of patriotism and pride and adventure. So that was my path to getting out of my hometown, was quickly swept away into uh offensive combat as an infantry marine, where my unit was the main effort of the assault on Fallujah, where we liaised with special forces, air and ground intelligence, tanks, fixed and rotor wing aircraft, and assaulted a city from north to south. It was incredible. I'm lucky to be alive, and it really was just an epic experience. And then after that, as a young Marine, went on a Marine expeditionary unit, which is a naval vessel, and traveled the world and saw half a dozen different countries as just a 19 or 20-year-old kid. And that was kind of the first time I, coming from Ohio, saw the rest of the world. First time I had sushi, things like that. Like my daughter is four years old and she eats sushi. I'm like, didn't know what that was until I was 19. And then after the Marines, I got right into government contracting. I was hired as an internal employee doing recruiting and resource management, and that was an awesome opportunity. I think it's just this like honeybee hive of worker bees who just kind of get in line and follow the rules and don't question anything. And, you know, I don't like much about it, but I will say it provides awesome opportunity. And it is the central hub for not only the politics, which I despise, but also for national security and you know, things that make America great. And so from that perspective, I lucked out getting into government contracting. It provided an awesome career for me and with a limitless cap and so much to grow and learn. So yeah, it's been a great experience.

SPEAKER_02 6:57

So I know you came from humble beginnings as well, but you know, the Marines, I'm sure, have a way of humbling you quickly, as you just alluded to. But what's an early mistake that you made that you still think about?

SPEAKER_00 7:08

There's a couple of mistakes I've made that really stuck with me. One is I misplaced a rocket when I was in Iraq. And uh that that uh we were we were just sleep deprived, moving from house to house, and we had a minute to take our gear off, and like I left that thing in a house. And who knows if a bad guy made a bomb with that in the future. So that always stuck with me as kind of a professional regret. One of the biggest mistakes I made as a young professional in the workforce was I sent what is called a gross profit calculator. It calculated how much money a government contracting firm would make off of an employee. It took in their bill rate and their pay rate, and it showed you the margin. And I'd have access to those, and I accidentally attached it and sent it to the candidate that I was going to hire. Oh so I sent him the gross profit calculator for him. Needless to say, he didn't take the job, but you know, that always stuck with me as a double and triple check your emails, what you're attaching and who you're sending it to. So it was a good lesson learned. I'm glad I didn't get fired.

SPEAKER_01 8:22

Yeah. When you look at the generation coming up now or entering the workforce now, what do you think that they're getting wrong? And what are they actually getting right that they are not uh getting credit for?

SPEAKER_00 8:37

Hmm. Well, the the new generation is just by default totally capable with technology. You know, the up-and-coming generation probably is going to be just by default familiar with AI tools and things like that. One thing that they're not getting right is the importance of communication and relationship building.

SPEAKER_02 9:00

Yeah.

SPEAKER_00 9:01

And the CEO of NVIDIA talks about this, and he says, like, uh this computer skills, engineering skills, things that young people think make them elite and make them an invaluable asset, those are the things that AI will replace. But leadership, command presence, vision, teamability, people skills, communication, those are the skills that I think have degraded a bit with the younger generation that are just so important. The highest paid engineers in our community aren't just the most brilliant, they're the brilliant ones who can also present the engineering concepts to non-technical people and have them understand why it's important. Those are the ones that make the big bucks. And you see that like all over as well. You know, that the communication, presentation, public speaking, debate, critical thinking skills, team ability, teamwork, you know, positive communication, those are things that I think separate great performers and professionals from everybody else.

SPEAKER_01 10:16

Do you have a skill that you've had to work on? Is there one that you feel like, yeah, you know what, that's something I want to improve, or something that you actually worked on throughout your career?

SPEAKER_00 10:26

Sure. For me, it comes down to patience, actually. I am naturally a driven person. I came out of the wound that way. You can't stop running forward fast. I'm not missing motivation, follow-through, things like that. So things that I've had to work on are being less sharp, being more patient, being more understanding and sympathetic. And those are just things that I've had to actively work on. But as a young man, 18, 19, 20 years old, when all my buddies were playing Xbox and playing, you know, PlayStation, I mean, I had probably read 40 different personal development, business, investment books. I packed in my marine bag for the Marine Expeditionary Unit, I packed a bag with 21 books in it. And I read I'll read them all. Rich Dad, Poor Dad, Think and Grow Rich, 21 Ways to Win with People, Seven Habits of Highly Effective People, you name it. So, you know, I did learn skills through those books, such as you know, remembering people's names. And if you schedule the dinner and you're the first to arrive, sit in the seat with the worst view. You know, give the better view to your guests, like investing in the experience of other people. So I think like how to win with people is like a lost art. I don't mean like win, like you win, they lose. I mean like win-win, how to create winning relationships. That's like a lost art. And I did early career really pay attention to that.

SPEAKER_01 12:14

That's rare. I mean, for a young person to bring that many books and actually read them at that age, like professional development books.

SPEAKER_00 12:24

Yep. Again, it dawned on me in my late teens that realized that I come from a not a very successful background, and I didn't accept that narrative for my life. And so I just went on a mission to just go do it.

SPEAKER_02 12:42

Awesome. Well, you mentioned, you know, how you landed in GovCon almost by accident. So, what did you get wrong before you figured out how the business actually worked?

SPEAKER_00 12:51

I don't think I really got anything wrong. I just looked at it as an opportunity. Anyone that I could learn from, I just made sure they knew who I was. If I recognized that there's people in the company that are more successful and that they outrank me, I would make sure they knew who I was. I'd do them favors, I would work for them, I'd volunteer for projects. And pretty soon they knew that I could be dependent upon. And that's how I got promoted among my peers. I also frankly outworked my peers when I was coming up in the ranks. There was a solid year to two years between 2009 and 2011, where I worked, I would if there's 52 weekends in a year, I worked less than 40 weekends. Wow. You know, and like for me, that's not a big deal, but I couldn't understand why my peers wouldn't go in and put three or four hours in on a Saturday to just make more money, get promoted, be more successful. Like instead, you're out doing Sunday fun day or brunching and boozing, and it's like, where are your priorities? So I don't know what it is. I feel like so many people are like content with what I would define as like a normal life. Normal life is fine, but nowadays, like a normal life isn't what it used to be. I mean, families back in the 50s, like you could be a janitor and make a living for your family, you know. I mean, here you have to just do so much to like have space and freedom. I just can't understand why people wouldn't want to just put in a little more if that could lead to something.

SPEAKER_01 14:48

I'm gonna sound like my dad now, but there really is no substitute for hard work. And I think that certain people just either are born with some sort of like work ethic or they learn from somebody, right? My dad was an entrepreneur, and I don't think he was ever sick. He wouldn't go to the office, he would get up early, he would make his coffee, he would not eat breakfast, straight to work, right? And he would come home very late. And we barely saw him, but it is what sets people apart. You know, if you have work ethic, you can truly achieve so much more. And Ross, you said you didn't understand how your peers didn't put in those extra hours. I mean, they just didn't see the value of hard work and where that could take them.

SPEAKER_00 15:35

I had a conversation with a young professional. He's 27 years old. He works in our industry, reached out to me on LinkedIn, was like, sir, I admire what you've done. I just would love to just pick your brain. Any youngster who you reach, I always give them time. I do because like that shows me like they're at least asking the right questions. Like they're seeking something, they're not just settling for what they're given, right? So if someone's on their journey, you should recognize that and probably try to support them if you can in some way. All right, so let me break it down in terms of how to go from a rookie, okay?

SPEAKER_01 16:15

Go for it.

SPEAKER_00 16:16

It's simple. You're never gonna get rich working for somebody else unless you have some crazy, crazy specialized neurosurgeon trade where you can earn millions of dollars a year in salary, okay? If that's not the case, and you don't have an inheritance that'll get you wealthy one day, then eventually you will either have to become an entrepreneur, start your own company, or the long and steady route of have a good job, save, save, save, save, save, and make really smart investments. And then you could actually do pretty well. But if you're going to be an entrepreneur that calls for somebody, you have to figure out what value you're going to provide the industry that you serve or your clients. What can you give them that's better than everybody else? You have to identify what that is, right? What is your unique offering? You got to be realistic if the market also wants your unique offering. All right. If I sell broccoli flavored granola and that's the best thing I do in life, well, the market may not want that. Okay. So you have to make sure there's a market fit for your unique offering. Then you have to be realistic. So work ethic is one thing, but self-awareness is another. You have to be realistic if you have the skills needed to actually go do it as an entrepreneur. Like seven years ago, six years ago, I had a lot of skills, but I didn't know the first thing about buying a company. I didn't know the math. I didn't know the banking. I didn't know the lending. I didn't know the structure of a deal. I had no clue. There's no way I could have started a successful private equity company. Didn't have it. Fast forward to today, I've worked with amazing private equity professionals, Godspeed Capital, Doug Lake, Nat Fogg, Cam, these guys are incredible. And I've learned so much from them to where, you know, now I could probably step into that role. So the point is, you have to be self-aware to know if you don't have the experience, then go get a job where you can learn it. And then, like after you feel like you have the confidence and the skill through years of experience, then start your own thing where you can offer your unique flavor to the world. So that is like, you know, my big advice for people who want to get into entrepreneurship. My best advice for folks who just want to like become an executive at a company. Maybe you don't want to start your own, but you want to be the COO or CEO of a big company. You know, that that has to do with, you know, make yourself known, volunteer for work before you get a promotion. Take on more and more responsibility. Make sure key players in the company and key leadership know who you are. They need to know your name, know what you can do, and know that they can count on you. Make yourself indispensable. Continuously volunteer for more work. If you do that and you are working for a good leader, then you should grow. There is a law of the lid. If you do all of those things, but you're working for a poor leader, they'll never take you anywhere. You can't go by yourself. So those are a couple of little avenues, little words of wisdom, whether you want to start your own business or you want to climb the corporate ladder.

SPEAKER_01 19:53

I'm curious when you look at maybe somebody you're looking to promote, or somebody, like what do they have to do in addition to you know being hungry and volunteering for work? What is that one thing that you're looking for them to do for you to be like really impressed?

SPEAKER_00 20:11

Aptitude and attitude are so much more important than qualifications for me. Experience can't be substituted, frankly. I mean, experience is experience, like if you're hiring senior people, but if someone's got like the attitude where they will not fail, and they're just good clay, they've got aptitude, they're have a high aptitude. I'll give them a shot. I love giving people a shot. I've given people a shot and then fired them many times. I've given them a shot and then remove them from a company because this is business, it's not charity. But giving them great feedback on the way out, I think you have to give people a shot who are begging for it and let them prove themselves if they can.

SPEAKER_02 21:01

Yeah, it seems like you had that drive and you can sense it in others. It feels like when people show that they have that drive and they want to better themselves, they're able to apply that to their role because they care.

SPEAKER_00 21:14

There's a quote I love never underestimate someone who overestimates themselves.

SPEAKER_02 21:22

Cool. Yeah, that's nice. I like it. Um, so we always love to end on kind of a lighter uh note. Before we let you go, we have to ask, what's the one habit from the Marines that you can't shake? And does it drive your team crazy?

SPEAKER_00 21:39

Yeah, probably so. I have sometimes impossibly high standards.

SPEAKER_02 21:44

Yeah.

SPEAKER_00 21:44

I've learned to kind of manage that, but I feel like we can sense that from this conversation. Yeah, it's tough. It's a gift in the curse, honestly. But sometimes the standards are pretty tough and um that can be hard to live up to no matter who you are. So I've learned to try to balance that very fine line between pushing people too hard and the other end is pushing people hard enough that you turn coal into a diamond. And I have seen people that have worked for me just take the pressure and grow. And I know how cool that is to see people rise to the occasion and just transform. So I love doing that. And I'll probably, you know, I'll keep finding my balance, but high standards are probably always going to be there.

SPEAKER_01 22:38

I'm assuming that you are the kind of person who kind of likes that kind of drill sergeant environment. Like if I go to the gym, I have a personal trainer. I train with him three times a week. And I don't like somebody yelling at me. That's not how I thrive, even in the gym or in my professional world. But what is it that you need to be the best Ross that you can be? Like, how do you feel? Like, yes, I'm becoming a better leader person, whatever.

SPEAKER_00 23:11

I think like the only people that challenge me right now are my board, my board at Godspeed. They challenge me. I love it. I'm I'm finally getting someone to put higher standards on me than I have for myself. And it's amazing to surround yourself with people who will do that for you, but then also support you, right? If someone sets a super, super high bar for you, but then they also put their arm around you and help you get there. That's like the best feeling. That's how I respond the best. I love big challenges, but I also love positivity. So when I think about the best leaders I've ever worked with, they're people who will take you to places that you couldn't have got to on your own by setting high standards, but they'll also encourage you and coach you up to get there. That's just such a great powerful combination.

SPEAKER_01 24:05

So no yelling involved or needed.

SPEAKER_00 24:08

No, no, no. It's never like that. It's never like that. As bad as it gets, it's usually just direct. Like, hey, you realize this is no good, right? You know, like, you know, you realize like this is an example of something that looks good. And here's what you provided me. Why'd you do that? You know?

SPEAKER_01 24:29

Well, that's corporate speech for like, you know, hey, you know, dummy, like yeah, per my email.

SPEAKER_02 24:38

Yeah, exactly. Yeah, yeah. It's tough in this industry, like to have leaders that see your potential and actually help you act on it. You know, that there's so many companies that are so big and it's hard to get that approach. So I think anyone coming up industry would be lucky to have a leader who takes the time.

SPEAKER_00 24:55

If you're a rookie coming up trying to be a rock star, when you accept your next job, interview your leadership as much as they're interviewing you, you don't want to get behind a poor leader. It's the law of the lid. You can never be an eight on the 10 scale of leadership if you're working for a seven. You can never be a nine if you're working for an eight. You will never surpass their leadership level. So if you can get under a great leader, they'll take you somewhere if you let them.

SPEAKER_01 25:25

Well, that's great insight to end on. Ross, thank you for being a guest. We appreciate your candor and your insight.

SPEAKER_00 25:33

My pleasure. Great to see you both.

SPEAKER_02 25:40

Thanks for listening to Rookies to Rockstars. GovCon doesn't come with a playbook, but these stories might be the next best thing. Follow the show, share it with someone still figuring it out, and connect with us on LinkedIn. We'd love to hear from you.