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Rick Tossavainen & Steve Bailey
Episode 919th April 2023 • Beyond Strategy • Andy McEnroe and Jenn Wappaus
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Part two of our three-part series on building a business in the government contracting market. In this episode, we dive into the second way businesses are formed - the spin-out of an operating business - and speak with Rick Tossavainen, CEO, and Steve Bailey, COO of Dark Wolf Solutions.

Dark Wolf Solutions is an innovative company that spun out from Wolf Den Associates in 2018. They provide cutting-edge cybersecurity solutions to the federal government, helping agencies safeguard their critical systems and data from cyber threats. With their unique approach to cybersecurity and a team of top-tier experts, Dark Wolf Solutions is quickly making a name in the GovCon space.

In this episode, Rick and Steve share their experiences of starting and growing a spin-out company, including the challenges they faced and the lessons they learned along the way. They discuss the unique advantages and disadvantages of the spin-out model and how it differs from other approaches to starting a business.

Whether you're interested in cybersecurity, entrepreneurship, or simply want to learn from successful business leaders, this episode is not to be missed. Tune in now to hear from Rick Tossavainen and Steve Bailey of Dark Wolf Solutions in Episode #9 of our series on building a business in the government contracting market.

Transcripts

Andy McEnroe (:

Hi, hello, and welcome to another episode of Beyond Strategy, an ACG National Capital Region podcast focused on the leaders that drive innovation, enhance understanding, and achieve market clearing outcomes in the National Capital Region.

Andy McEnroe (:

I am Andy McEnroe of Raymond James's Defense and Government Investment Banking team.

Jenn Wappaus (:

And I am Jenn Wappaus of the Infinity Wealth Management Group at RBC.

Andy McEnroe (:

Episode 9 marks the second part of our three-part series on the formation of companies in the government contracting market. Today, we focus on Dark Wolf Solutions, an innovative company that came into existence via a spin-out from Wolf Den Associates in 2018.

Andy McEnroe (:

On the hot seat in the world-renowned Beyond Strategy studios are Rick Tossavainen, CEO, and Steve Bailey, COO. Dark Wolf Solutions combines the most bleeding-edge technologies with deep federal domain expertise through cutting-edge intelligence services, DevSecOps, Agile software development, information operations, penetration testing, and incident response, among other capabilities.

Andy McEnroe (:

Rick and Steve are both innovative business leaders that bring both experience and creativity to the job. In my opinion, what separates the Dark Wolf team from the pack is the culture that they've established as well as the mission-focused work that they pursue.

Andy McEnroe (:

In addition, Rick, Steve, and the other team members that I have met are genuinely good people and know how to balance hard work for their core customers with an enjoyable working atmosphere. Now, here is our discussion with Rick Tossavainen and Steve Bailey of Dark Wolf Solutions.

Andy McEnroe (:

We are excited to be joined today on Beyond Strategy by Rick Tossavainen, CEO, and Steve Bailey, COO of Dark Wolf Solutions. Gentlemen, thank you for being here.

Rick Tossavainen (:

Thank you. It's a pleasure to be here.

Steve Bailey (:

Thanks for having us.

Andy McEnroe (:

Let's start from the beginning. Did either of you envision when you joined Wolf Den in 2013 and 2016, respectively, that you would be running a rapidly growing government contracting firm?

Rick Tossavainen (:

Well, that was always the hope, Andy. I'm glad that you call it that. It certainly feels like that on some days. Some days it's a little bit more challenging and it doesn't feel like we're going in the right direction, but overall, it has been a great ride getting here and the firm continues to grow.

Rick Tossavainen (:

We've got several things in our pipeline we're still pursuing and we've always positioned ourselves as a growth organization. We'll touch up on this because I read ahead, as you said, I read ahead in some of the questions, so I know we'll be touching upon this more in the future.

Andy McEnroe (:

Well prepared for the interview. That's a check plus, A plus for the day, Rick. Steve, you got to catch up here. Our mini-series is focused on the creation of companies. Your story is fairly unique in the marketplace in that you were spun out of a privately held government contracting advisory firm, Wolf Den, that we referenced earlier. Can you walk our audience through the creation of the technical solutions team inside of Wolf Den and then through the conversations that led to the carve-out?

Steve Bailey (:

Yes. Let me start by saying, Kevin Robbins and Barry Landew, the founders of Wolf Den, certainly a lot of credit to them on not only having the vision of this being potentially a really interesting platform for a services spin-out but also being willing to take a risk on potential OCI, perceived OCI with some of their customers, given the fact that we all knew going into it that the more successful we were as technical solutions, the more we were going to raise up on other companies' radars that we were potentially going after services work.

Steve Bailey (:

Starting from the beginning and letting them or having them fully support this and be receptive to us building a team, building capacity, and then using the resources of Wolf Den, not only on the basics of capture and proposal in that piece, but also just the networking, the introductions, the ability to potentially get introduced to partners who helped us early on with slots on contracts that we may not have otherwise had any business meeting with.

Steve Bailey (:

Fast forward to 2018, we really started to have some altitude and airspeed, and we knew there were some things we wanted to go after as a prime. Ultimately, the perceived OCI issue that we talked about early on started to rear its head a little bit. Admittedly for Rick and I, that was a great catalyst to start the conversations around, "Now might be the right time." We had essentially matched them in headcount. Of course, our folks were far more technical from the computer science, computer engineering disciplines, and just different motivations, different interests, and what kind of benefits that we're speaking to our folks.

Steve Bailey (:

Certainly had its moments and bumps along the way, but we remained four good friends. Of course, Barry and Kevin remained part of our board and are extremely valuable as folks who continue to help us connect in the market and give us the access to both partners and just where we can look to find that sage guidance that you'd expect from a great board.

Jenn Wappaus (:

As you went through the split with Wolf Den in 2018, what was the hardest part of emerging on the other side as an independent company? Then did you have the necessary infrastructure to effectively grow the business?

Steve Bailey (:

Yes. We knew going into early in '18 that we felt like this could be the year that we set everything up to be ready to spin out. So a lot of work in 2018 went towards establishing separate back offices, if you will, setting up and identifying those key growth, overhead folks that were going to be on the ground day one with Rick and others doing the early capture proposal. I mean, right at that point, everyone's wearing multiple hats.

Steve Bailey (:

But long story short, certainly the early days were rough in the sense of we were just learning as we went, building the plane as we flew it—to use a consulting reference. But it was great. I look back on those first few months and it was just a whirlwind. Before we knew it, we had a couple of prime contracts that really helped pour gasoline on the fire.

Steve Bailey (:

Everyone knows we're all chasing that next wind, I think, in this industry and certainly you get a rush off of that. Having some of those winds out of the gate really helped propel us, I think, as we looked to where we wanted to go and where we wanted the firm to head.

Jenn Wappaus (:

Sure. We like to focus back on leadership in a growing organization. In order to be an effective leader, you need to invest in the people around you. It's clearly evident that you have built a great brand out of Dark Wolf.

Andy McEnroe (:

You have a wolf head. There's a rumor.

Steve Bailey (:

Rumor.

Jenn Wappaus (:

There's a rumor. There's a rumor. So how do you establish that culture?

Rick Tossavainen (:

Yeah so…

Steve Bailey (:

She's asking about leadership. Do you want me to take that one?

Rick Tossavainen (:

Yeah, take this one then. Let me take a sip of my Mai Tai here first. Said by people far more knowledgeable than us in this industry who said just always be replacing yourself. Be challenging the people who are below you to take on your role and continue to build your own career.

Rick Tossavainen (:

I think that's something that we have done pretty well. We've been very fortunate. We've surrounded ourselves with really strong, what we call, practice area leads. They lead the capability centers for us. We have a strong growth team. And we've really let them run what are—effectively in the practice area lead case—mini Dark Wolves.

Rick Tossavainen (:

The practice areas now are the size of Dark Wolf just a few years ago, and they've got P&L responsibility. They work with the growth team to determine what we're going to pursue. Then they not only assist with writing those winning proposals, but then of executing those things.

Rick Tossavainen (:

So in some ways, they've become their own CEOs of what was Dark Wolf. And it's refreshing to see that. They also push Steve and me to go out and work on the business instead of in the business. So figure out what's next, what are we going after from a strategic perspective, in my case, or for Steve, how to position the company so that we can go after those bigger pursuits. And really, our focus now going forward is full and open into next year. So how do we position for that?

Andy McEnroe (:

Are there any guiding principles, a North Star, if you will, that you communicate with your team about that they then turn around and leverage in building their respective practice areas?

Steve Bailey (:

We, of course, have our values. Rick may have touched on this already, but "customer first" is one that we adopted from Wolf Den. We recognize our business is only viable because we have customers who see us as trusted advisors, respect our technical capability, and understand that they're getting a partner who's prepared to invest in them as much as they're investing in us.

Steve Bailey (:

So we certainly are quick to leverage that value when it comes to the big picture, how to think about solving problems both at a tactical level and then at a more strategic level when it comes to how we want teams to be executing on contract, how we want our PA leads to be representing us both in the market to partners, but also to potential new hires or to customers that we meet.

Steve Bailey (:

Certainly, we've always looked at this as a long game. We do want to build those customer relationships. We want to help make people from our customers' side successful so that they can move on into bigger and better roles and that they think of the first call being, "I need to get Dark Wolf in here with me in my new capacity."

Steve Bailey (:

To me, that's how I want our relationship to evolve with customers versus thinking about how can we position this contract type to be the most profitable for Dark Wolf, or how do we make sure that we maximize our potential bonus. I think those are very near-sighted ways of looking at how to build a brand and how to build a confidence with your broader leadership team about what's important to you as the most senior folks in the firm.

Jenn Wappaus (:

What's the dynamic between the two of you and the rest of the leadership team? What roles do you play in building culture, running the business, orchestrating growth among the day-to-day tasks that you have to do as well?

Rick Tossavainen (:

I can start. I'm sure Steve will fill in, but I get to do all the fun things.

Jenn Wappaus (:

What is that?

Steve Bailey (:

What would you say you do here?

Rick Tossavainen (:

What would you say you do here?

Steve Bailey (:

You're a people person.

Rick Tossavainen (:

I'm a people person, yeah. I take the requirements from the users and I bring them down to the developers. I am far more outward facing meeting with potential customers or meeting with customers when we first sign with them, also meeting with partners in industry, meeting with fine firms like the two that you represent here, and really trying to figure out how do we best position—and I've touched upon this earlier—but how do we best position Dark Wolf for graduation as a small business and establish those relationships are going to be necessary for us as we always say, "We got to crawl, walk, run to build the business. And we're going to have to do that again as we move into full and open here.

Rick Tossavainen (:

Meanwhile, Steve deals with all of the internal machinations of the company, all of the hard things, and he says, "Stay out of my business."

Jenn Wappaus (:

Just like that, "Stay out of my business."

Rick Tossavainen (:

Yeah, just stay out of here. Oliver is much the same. He runs growth. Again, he's 100% focused on that, especially working with partners to build teams and then actually field those teams during the proposal phase.

Rick Tossavainen (:

Then our PA leads—I touched upon them earlier—they really are running their own little businesses here, but we expect them to work very well together. We know that there's a lot of gray lines. We have cybersecurity, we got software and DevOps, we got digital transformation. Most opportunities that come out these days are focused across those. So we expect them to work with each other.

Rick Tossavainen (:

They actually just had their monthly lunch yesterday. They sent us the bill after they get together and commiserate over what it's like to work for us. Hopefully-

Andy McEnroe (:

It's got to be a big bill.

Rick Tossavainen (:

It was two and a half hours yesterday. I don't know how you spend two and a half hours-

Steve Bailey (:

I should get a stopwatch and have it go off when they leave so that they're aware that we're tracking how long they're gone.

Rick Tossavainen (:

Exactly. Especially when they ate at Taco Bell. I mean, how do you spend two and a half hours in Taco Bell? We only authorize for $30.

Steve Bailey (:

I do think it's worth noting that we see a lot of firms and friends in the market, frenemies in the market even, where the couple of folks at the top of the organization, they do tend to blend a bit more in roles. I don't know, maybe we're lucky, maybe we're not. I don't know. But certainly between Oliver, Rick, and I, there's some pretty delineated lines of what we're responsible for.

Steve Bailey (:

I would hope that helps with some of the broader leadership team in the firm as a whole because there creates some real accountability there. There's no mistaking. Like if it's operational-related, that is my problem to deal with or my success to deal with, I guess, in some cases. But I do think that that's been helpful for us is that we create a bit of a united front, but also have a clear understanding, clear messaging, if you will, to the rest of the firm about who to go to for that ultimate decision responsibility.

Andy McEnroe (:

Great answer. But that was more of the generic podcast answer. I want to peel that response back. Let's dig into the fact that your relationship goes beyond the four walls that comprise Dark Wolf. How does your family connection help or hurt you when you're running the business?

Steve Bailey (:

I don't think holiday dinners and get-togethers are really loved by the rest of the family because all we do is talk about Dark Wolf. It's surprising that we actually tolerate each other as much as we do. We meet at the gym every morning at 6:45, so we're together first thing in the morning. We're at work, we share a wall in an office all day. Then obviously, we oftentimes are out doing networking things in industry events at night. It's surprising that we don't get into arguments or fights anymore.

Andy McEnroe (:

Would you say that that characteristic is unique to the two of you because of your personalities, or is that an inherent family trait where you trust the other one in the pursuit of their work stream?

Steve Bailey (:

It's possible. Obviously, there's no question of the trust between the two of us. And there's also, I think, a feeling of we've never—as far as I can remember—never had any issue that's ever been unresolved in front of anyone else in the company.

Andy McEnroe (:

Because it was resolved when you were kids growing up.

Steve Bailey (:

Well, yeah. In a lot of ways, yes. But there is 100% a united front there. There's no question. Even if I have a complete disagreement with Rick or vice versa, that's never going to go beyond a private conversation in front of anyone else.

Steve Bailey (:

Then to your point, if he says we need to jump on something, it's how high, and I think vice versa there. And I do think that it's part of what makes this job extremely fun is you get to go to work with someone that you have such a high degree of confidence in, is supporting you, and of course, in turn, you want to do everything in your power to make that person successful as well.

Steve Bailey (:

I think we are probably uniquely positioned compared to some folks, maybe in that regard. But it does make the job a lot of fun to have this connection and just be able to spend 12-plus hours a day with someone you enjoy spending time with.

Rick Tossavainen (:

We still fight for our favorite son status with dad, though.

Andy McEnroe (:

Who's winning currently?

Rick Tossavainen (:

He called dad yesterday. It's been two weeks for me.

Andy McEnroe (:

Would you say it's easier to work with a sibling or a spouse? Jenn, that question is kind of for you, too.

Jenn Wappaus (:

Yeah. I've actually done all of that, so I don't think it's a big deal at all. I worked in a family business growing up, though.

Rick Tossavainen (:

Your sibling was a spouse?

Jenn Wappaus (:

That's weird. Come on. We're not in West [crosstalk 00:17:12]

Andy McEnroe (:

Put that in the blooper.

Rick Tossavainen (:

That's part of the blooper reel.

Steve Bailey (:

My wife does work with us. In fact, anything you see on social media is her. Even when it's me posting, it's usually her.

Rick Tossavainen (:

It's probably a security violation.

Steve Bailey (:

Right. Yeah. Linkedin.

Rick Tossavainen (:

Talk to the FSO.

Steve Bailey (:

So it's certainly… Early on when we were very small, she actually did our payroll and did a lot of our accounting stuff. She is a communications marketing person by academic and professional background.

Steve Bailey (:

I will tell you, you find out real quick how strong things are when you've got someone in a very critical role who has no professional background doing the work, and at 9:30 at night, she's trying to figure out how to get into a waft and submit critical invoices that we need to get paid in 30 days so we have the cash flow available. But it all worked out in the end. Now she repays it by doing things like buying wolf costumes and doing stuff like that and subject me to humiliation from the company.

Andy McEnroe (:

We've spun away from our initial conversation—pardon the pun—but let's get back to the point here at hand as we're talking about how businesses are formed in the government contracting market.

Andy McEnroe (:

For individuals that are inside of a firm currently that may think that that firm or the division of the firm, I should say, would operate better independently, is a spin-out a viable strategy? And is that something that could bring up directly with the leadership of the parent company? Or is this something that needs to be established on day one, knowing that it could be a viable outcome down the line?

Rick Tossavainen (:

We got to be careful what we say here because we have 250 people coming to us asking about spinning it out from Dark Wolf tomorrow.

Steve Bailey (:

It's a terrible idea. I think our situation was admittedly very unique. What Wolf then does in the market now, Deep Water Point, is obviously an incredibly well placed and incredibly valuable service and incredibly good at what they do.

Steve Bailey (:

But they also are not necessarily as competitive to say a traditional GovCon services firm and thus does provide some opportunity for them to say, we could be a platform for a company like Aspiring Dark Wolf to create the infrastructure, create the groundswell, if you will, to then basically spin out and go do your own thing.

Steve Bailey (:

I do think for other practitioners who are maybe in more traditional settings with a services firm that's providing direct support to the government. One interesting scenario would be, I think as a small to medium-sized firm, one of the pieces of advice that we've always gotten that is resonating is stay as deep and as narrow as you can for as long as you can.

Steve Bailey (:

If you're in a position where you are providing what would be maybe a more ancillary capability to a firm that's more focused strategically on X and Y and your Z, I think that could be maybe an interesting scenario where you're saying, let me do what I'm good at and let me potentially create an economic advantage for you by doing this as a separate entity. But let me do it in a way there I can eventually spread my wings and fly.

Steve Bailey (:

I think that could be interesting because I do think most of the small firms that we interact with and have a lot of respect for, tend to live by that same credo of stay deep and stay as narrow as possible.

Rick Tossavainen (:

I'd also say it takes a long time to get through this. Plan for at least six months and that is if conversations are going extremely well. It's just a lot of planning, a lot of determining what the organization is going to look like, what is the ownership structure, what's the cap table look like, that stuff takes time.

Rick Tossavainen (:

As Steve mentioned, we were fortunate because from the beginning, we thought this could happen. Although the original outline of what Dark Wolf would be was a one-page piece of paper. I think as we got closer and closer to finalization of an operating agreement, we wished that piece of paper had a lot more content and details in it. A lot open to interpretation, but it was a good starting point.

Andy McEnroe (:

Well, Rick, Steve, you're part of a new experiment here on Beyond Strategy, an ACG National Capital Region podcast. As Jenn and I try to be a lighter, funnier, but still informative version of bringing you info and intel from around the National Capital Region. Our newest experiment is to do this interview with a cocktail in hand. Jenn, let me turn it over to you to tell our audience what the cocktail is for this interview.

Jenn Wappaus (:

Yeah. We're having wonderful Mai Tais from Tiki Thai in Reston.

Andy McEnroe (:

May or may not be the favorite bar of Rick and Steve.

Jenn Wappaus (:

May or may not. I mean, that's up to you guys. But I would say if you have not been-

Andy McEnroe (:

They haven't paid for this endorsement.

Jenn Wappaus (:

No, they have not. And if you have not been, I would highly recommend it. Their Mai Tais are fantastic, right?

Steve Bailey (:

Yeah.

Rick Tossavainen (:

Spectacular. Ask for Sherry. She's the best waitress there.

Jenn Wappaus (:

We would love the audience to learn a little bit more about what makes each of you tick. We typically ask this in a different way.

Andy McEnroe (:

Back when we were serious podcasters.

Jenn Wappaus (:

When we were serious podcasters, we'd ask for you guys to describe your leadership style in one word. But since your family, Steve, if Rick were a happy hour beverage, what would he be and why? And Rick, same question for you about Steve.

Rick Tossavainen (:

You're going to use the time to think? See how I respond?

Steve Bailey (:

Yeah. I want to see where I want to go with this.

Rick Tossavainen (:

I know you're going to say malt liquor, so you might as well just say malt liquor.

Steve Bailey (:

No.

Jenn Wappaus (:

Why would he say that?

Rick Tossavainen (:

Wait, you'll hear. I got an idea. I have an idea. To me, and I'm hoping again to get some sponsorship, not just from Tiki Thai, but hopefully from Solace Brewery, Steve is like a Partly Cloudy from Solace Brewery. We happen to like Solace. We keep it on tap in the office. It is empty right now, the keg. But why was Steve a Partly Cloudy? You've got a little bit of haze in there, but it is a tasty beverage. However, it can be very bitter, though, if you cross it, you drink a little too much.

Jenn Wappaus (:

There you go.

Steve Bailey (:

That's pretty tough to beat.

Rick Tossavainen (:

I was thinking about that last night.

Steve Bailey (:

Yeah, it's good. I'm glad. Maybe a Jack and Coke. If you put me on the spot, I would say you drink a Jack and Coke when you're looking to have a lot of energy into the night. Rick is definitely, I like to refer to him as a bit of a pace setter. He's first guy in type person, he's the guy who'll stay the longest and so it motivates me. I know it motivates a lot of the leadership team to obviously want to match that.

Steve Bailey (:

In that regard, that's the Coke. But then when you have too much of it, it can be a real crash and burn situation. But no, I guess I would say you can never go wrong with it. It's a good drink. You can use it at a more higher end social setting and you can go into a dive bar and order one as well. It works in all settings, basically like Rick, I guess. That would be, I guess, my off the cuff response on that.

Rick Tossavainen (:

It's the nicest thing you ever said about me.

Jenn Wappaus (:

That was nice.

Rick Tossavainen (:

I'm getting a little emotional.

Jenn Wappaus (:

That was nice. Coming full circle, what are the plans for Dark Wolf moving forward? Will you look to acquire companies? Where might you deploy capital to fuel further growth? What are you guys going to do?

Steve Bailey (:

I like to watch the bank account increase. I like to spend anything on anyone. But look, I think we make no illusions about what our objectives are. We want to grow as a firm. We think that's how we not only provide our employees with new opportunities to increase their own and meet their own career goals, but also we think we've got a capability and a set of differentiators that give us a lot of runway here.

Steve Bailey (:

I think we're obviously focused on organic growth. That's certainly the objective. But we also do recognize that as we've learned a bit more and had a chance to meet more folks in industry and understand how some of these different firms are using all of the levers available to them, I certainly think acquisitive growth is not something we're afraid to explore.

Steve Bailey (:

I think we would be very conscientious about what type of firms and what type of capabilities and things that would be interesting to us. I also think we would be looking for firms that are ready to really double down and become part of a bigger team, if you will, and really see if one plus one really can equal three.

Steve Bailey (:

But obviously, a lot of people are interested in that type of firm and so we'll have to see if we can identify someone that might be interesting in that regard. Not that we're actively looking per se, but it's more of just meeting companies in the market and assessing where they're at in their life span.

Steve Bailey (:

But our number one goal is to continue growing in not only the capabilities that we do currently, we're looking at maybe adding one or two things to the capability portfolio, but then really doubling down on some of the customers that we have today that we're very passionate about their missions, be it the SOCOMs of the world, Air Force, of course, some of the DOD at large, and then, of course, some of our Intel customers as well.

Jenn Wappaus (:

Excellent. Let's talk recruiting and how you can grow the business through strategic hires. What's the pitch for why a potential employee should join Dark Wolf over another organization operating in the federal market?

Rick Tossavainen (:

Yeah. Almost every strategic hire we've ever picked up was by accident, but that's a good thing. You directly asked this, but a lot of it is meeting with other people in the industry, having conversations about teaming and growing to know that person and they get to know you.

Rick Tossavainen (:

Fortunately, we've, over time, had people get excited about Dark Wolf. I think the things that draw them in is that while we're a small company, we believe that we punch above our weight class. That's because we do have a pretty sophisticated back office.

Rick Tossavainen (:

We have a strong capture and proposal development shop. We're not afraid to make big bets and to go after things that are really exciting to us. New customers, customer intimacy, okay, I mean, love to have it. If you don't have it, doesn't mean we're not going to go after it and try to prime something.

Rick Tossavainen (:

We've been very successful with that. It is, again, not the recipe for success, but at the end of the day, it's Steve and me who get to make the decisions. We don't have a board sitting over us that's going to say, no, you can't go after that because you haven't performed enough capture. You can't go after that swim lane because it's just too different from what you currently do.

Rick Tossavainen (:

Had we maybe listened to more of the traditional GovCon rhetoric, we wouldn't have primed anything for the longest time. But when we launched from Wolf Den, we had two prime contracts, one at STRATCOM and one at NGA, neither of which we had a lot of customer intimacy in. We knew the work, we knew how to do the work, but we didn't know that specific aspect of it and in both cases, we were successful.

Rick Tossavainen (:

We're still at STRATCOM on effectively the same program. NGA, we were there until they closed the Office of Ventures and Innovation, which wasn't our fault. That I think has been a way to draw in strategic talent, people who want to be a part of a winning team.

Rick Tossavainen (:

People will know that if they bring us something really interesting, we'll put the whole firm behind you, like, let's go after it. Let's try to win it. When we win it, we'll have high fives, we'll toast each other. But then it's, all right, let's get executing it. Meanwhile, move on to the next thing. What else are we going to pursue? I think that that attracts a certain type of person, and we've been successful at bringing them in.

Steve Bailey (:

I'll just add one other thing to that is, I would say in our experience, and I think we've gotten this advice as well, is that strategic hires are never going to come into your orbit when you want them to come into your orbit. They're going to come in when, in some cases, maybe the worst possible time.

Steve Bailey (:

I think it's incumbent upon you as the senior leaders to be really, one, putting your heads down and figuring out how to potentially make someone who you're convinced is going to add your business fit in and how to make them productive and in a position to be successful.

Steve Bailey (:

But also, ideally, you're hiring enough of the right leadership team around you that those other individuals don't see people as threats. I think we've been very lucky in that our leadership team is pretty bought into our moves. When we've brought in a new director, let's say, or someone at a senior level, there's been a very receptive response to that. And a lot of like, okay, we're better together than worrying about is this person coming in to potentially split the baby, if you will. I do think that's a big part of it as well.

Steve Bailey (:

Of course, having some levers available to you as you think about your org structure, how your cap table is set up, what type of organization you are for those really hard to find and hard to reach people is important too. 'Cause oftentimes salary and bonus are not going to be enough to really attract those folks that can make a difference for you in the long run.

Andy McEnroe (:

It is clear from our conversation today that Dark Wolf is a differentiated business within the government contracting market. You've also built a tremendous culture by surrounding yourself with A players. But as we pivot toward the end of our time together today on the podcast, I'd like to talk about life lessons that may be additive to our audience. What's one lesson your career has taught you that you think everyone should learn at some point?

Rick Tossavainen (:

This is the obvious one, do not have the bathrooms in your main area. This was your office. This is awful. Terrible. It's a terrible idea.

Andy McEnroe (:

There's got to be a story behind that.

Rick Tossavainen (:

Steve found really nice space down in Chantilly.

Steve Bailey (:

It was like $8 a foot. It was fantastic.

Rick Tossavainen (:

Yeah, it was not class A.

Steve Bailey (:

No.

Rick Tossavainen (:

In the back, there was this great workshop area. We actually built several drones there. You could fly the drones in there. We actually had one of our interns call up Dulles Airport and get approval to fly his drone outside the garage and flight above.

Steve Bailey (:

Which was right in the flight path. I didn't know about that until afterwards. I was very concerned someone from the FAA was going to be calling us.

Rick Tossavainen (:

But the space was great space for early launch.

Steve Bailey (:

Dogs could be in the office.

Rick Tossavainen (:

Yeah. Dogs who are well behaved aren't always well behaved either in the office. That led to a few issues. But we eventually had all the cleaning materials that you could possibly want.

Steve Bailey (:

But it did have one downside, which was as a industrial space, the restrooms were in unit versus being in a hallway. It was just it was less than ideal for some of the obvious reasons. One being that it was 98% men in the office. The restroom was right next to my office.

Rick Tossavainen (:

That meant that the women's room was often open.

Jenn Wappaus (:

Did you use it?

Rick Tossavainen (:

There may have… Then when someone's looking for you and they're like, "Where's Rick?" You're trying to move the tiles up so you can get up there and low crawl out because you can't be seen walking out of there.

Steve Bailey (:

It's probably part of the blooper reel.

Rick Tossavainen (:

Yeah, it's a blooper reel.

Steve Bailey (:

Someone is actually quoting myself back to me, so I don't know how this comes across if I'm quoting myself through someone else. But they made the point of I was… One of the guys who now is running our software DevOps practice area, obviously one of the three pillars for us in overseeing probably 75-100 people from Dark Wolf, he just got promoted recently, so we had a dinner with him and we were talking about the story of how he got to where he was.

Steve Bailey (:

Basically he said he had just gotten elevated to be a PM. He was PMing his first project. He was six months doing that. Myself and Oliver took him out to lunch. We basically said, "Sam, what do you think about stepping into the practice area leader role?" He's like, "Well, I've only been doing this for six months. I'm not sure if I'm ready to do that yet." I said, "Don't worry, I've never been a COO before, but I'm doing that too. We're going to figure this out together."

Steve Bailey (:

What I'll say from that is just I do think there can be this perception of there's some schooling or there's something these people that are running these companies have had access to that you as a practitioner, maybe that are sitting in a seniorish level role, haven't had or feel like you're missing from your portfolio, if you will, of skill sets and experiences.

Steve Bailey (:

I would tell you that it's almost like having kids, waiting for you to be in that perfect position of having them is a fool's errand. It's like there's some level of you got to rip the Band-Aid off and trust in yourself and then trust that you can put the people around you, if you will, to basically make you successful.

Steve Bailey (:

It doesn't always work out, but I think that's to me an important lesson here because I don't think there's a Dark Wolf if Rick and I don't make a couple of big leaps throughout the early years of 2014, 2015, 2016.

Jenn Wappaus (:

We end all of our interviews with maybe the most imperative question that we ask, what is the most important thing that we should know about Rick Tossavainen and Steve Bailey?

Rick Tossavainen (:

I would say, well, hopefully when people think about me, they think about me as being… Steve mentioned this a little bit earlier, but energetic, really enthusiastic, really… We said this earlier, too, we're really there for the win. We love to beat others. We love to go up against the bigs in a full and open. We love to walk away with the win. It is it's what energizes us. It's what feeds us. It's what makes us want to come to work every single day.

Rick Tossavainen (:

I love coming to work. I'm in an office person. I know that's not always super popular these days. I love seeing people on camera. I feed off all of that energy. I love meeting with customers. I love meeting with industry.

Rick Tossavainen (:

We said this too before, although not in this interview, this is our time. We feel like, what a great time to be in the government industry. We've got this whole DevSecOps revolution, continuous ATO, AI/ML. Things are moving fast and it's really wonderful to be a part of it.

Rick Tossavainen (:

We've got great leaders throughout the government. One of them in particular that we love very much is leaving her post, but she's left in a good spot. It's really exciting. That's why I want to be here. That's why I'm going to continue to be here. I'll continue to do it till it's no longer fun.

Steve Bailey (:

I can imagine some things that people do say about me at Dark Wolf. But I think for me, I would hope that people see, especially given my role in the company, me as being fair. Despite a little bit of the fluff, if you will, about me being cheap or hard on making decisions, I think the reality is that I try to be really transparent with our leadership team. I feel like I want them to be part of decisions. I want them to feel like they have not only the accountability, but the authority to make decisions.

Steve Bailey (:

To me, I've always said this, it almost feels like a dream to me that we actually own Dark Wolf. In a lot of respects, I feel like sometimes I'm the cat that caught the canary in terms of the way I run it. I don't feel like it's mine. I feel like I'm running someone else's company and I'm going to manage it in a way where it's like, I just want to make the company successful.

Steve Bailey (:

That's the approach I've taken. I would hope that people see me in that respect. I think the leadership team does, by and large at least, that they have my full support to execute the work, to go after the work that they think is right, and on personnel decisions that they have my full backing on good and bad in terms of promotion readiness, moving into bigger roles, and then where we have performance issues.

Steve Bailey (:

Rick said it as well. I do feel a lot like, we say this quite a bit around the office, it feels like this is our time. We have something special here and we need to capitalize on it because we're only going to have one real shot to do this right.

Steve Bailey (:

It's really important to me that we look back on this for however long the ride is and are able to say, we did it the right way. We took care of the people that mattered to us and helped us achieve those goals and we're proud of it. That to me would be the best possible outcome.

Jenn Wappaus (:

Rick Tossavainen, CEO and Steve Bailey, COO of Dark Wolf Solutions, thank you for joining us today.

Steve Bailey (:

Thank you for having us.

Rick Tossavainen (:

Thank you for having us and thank you for the drink.

Andy McEnroe (:

Well, special thanks again to Rick Tossavainen and Steve Bailey of Dark Wolf Solutions for joining us here on Episode 9 of Beyond Strategy, an ACG National Capital Region podcast.

Andy McEnroe (:

We also want to thank you, the listener, for joining us today and remind you, if this is your first time listening, to subscribe wherever you get your podcasts from. For Jenn Wappaus, I am Andy McEnroe. Robert Miller and the Silver Edge story is up next. We hope you will join us on the next episode of Beyond Strategy.

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