Scaling With People
Tired of spinning your startup wheels but never gaining traction? Buckle up, founders and CEOs, because this podcast is your rocket fuel to profitability! Every week, we ignite explosive conversations with bold-faced founders, brainy experts, and even a few out-of-this-world vendors. Get ready to crack the code on growth, master employee engagement, and blast through your scaling goals. We’re talking real-world strategies, actionable tips, and perspectives that’ll make your business do a cosmic dance. So, strap in and prepare for lift-off!
Scaling With People
Scaling Without Breaking Culture with Ryan Hogan
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What if the difference between stalling at $8M and exiting at $55M wasn’t luck, but a set of repeatable choices about people, process, and stage-fit hiring? That’s the jump Ryan Hogan made, and we unpack exactly how he did it—from the hard lessons of a viral zombie race that crashed to the systems and recruiting moves that helped Hunt A Killer scale fast without losing its soul.
We start with the foundation most founders skip: vision, mission, and values that actually drive decisions. Ryan explains why talent sits on top of that foundation—and why mis-hires rarely come from bad resumes, but from poorly defined problems and vague expectations. We dig into the mistake of hiring a leader from a $100M company to run a $25M org, and how to find operators who have done the exact jump you need right now. You’ll hear how to set roles by outcomes, not titles, run a blank-slate org chart to reveal gaps, and reset expectations with early hires as the company evolves.
Then we get tactical on recruiting. Real recruiting isn’t posting and praying; it’s outbound sourcing, targeted outreach, and selling a meaningful mission to candidates who aren’t looking. Ryan shares why small and midsize companies need expert, stage-aware recruiting to win, how structured interviews and reference loops beat gut feel, and how EOS and peer groups like Vistage create the cadence and accountability to keep teams aligned as complexity grows. The result is a blueprint for building teams that scale, stay aligned, and deliver measurable outcomes under real-world constraints.
If you’re a founder, operator, or hiring manager who wants compounding growth without the cultural hangover, this conversation gives you the playbook: hire for the stage you’re in, design the org you actually need, and treat recruiting like the competitive advantage it is. If this resonated, subscribe, share it with a builder who needs it, and leave a quick review—tell us the one hiring move you’ll change this quarter.
Welcome to Scaling with People, your weekly playbook for turning chaos into compounding growth. Each week we go under the hood with battle test experts in all areas of business, from marketing to sales, operation, finance, and people, plus product and leadership to unpack the plays, numbers, and systems that turn chaos into compounding growth. Learn straight from founders and experts who've done it and continue to do it successfully. There's zero fluff, just moves that you can still immediately. This podcast is brought to you by Guide to HR, human expertise, AI-powered impact. Welcome everyone to today's Scaling with People Podcast. I'm Gwynavier Cuery, your host and founder and CEO to Guide to HR. What do a Navy veteran, a game company, and a hiring philosophy have in common? Well, it's one relentless founder who's obsessed with decoding what makes teams tick. On this episode, we sit down with serial entrepreneur Ryan Hogan to talk about scaling startups without wrecking your culture, recruiting like your business depends on it. Because let's be honest, it totally does. And why building badass teams is more science than luck. So get ready to rethink how you grow without those growing pains. Welcome, Ryan. I'm excited to have you on the call today and get started. But before we do, tell the audience a little bit about yourself.
SPEAKER_00:Yeah, sure. Thank you so much for having me. Appreciate it. Um, I a little bit about me. I'll give you like the 30-second kind of wave tops, uh, really two professional kind of tracks that I've had or trajectories that I've had over the last um 20 some years. But one has been entrepreneurship and the other's been the Navy. And and really what's been interesting is like, I don't know, the dichotomy, the the whatever it is. Like these are two completely different things. One is very process-oriented, structured, hierarchy, and the other is just living in a land of the unknown. Um, on the Navy side, enlisted when I was 17, mom side, my permission slip. I was a lost kid, a lot of energy, did not do well in high school. Um, not because I was dumb, but just because it didn't interest me. And um joined the Navy, was a helicopter crewman, flew on 53s and then 60 Sierras for a while, got a commissioning, um, and then headed to San Diego to drive ships. Um, that was the first 15-ish years, and then um eight years in the reserves. I'm the commanding officer of a unit out of Spokane, Washington. And then on the entrepreneurial side, just like lifelong entrepreneur, third grade selling creepy crawlers, washing cars, shoveling snow, mowing grass, like you name it. Um, and uh eventually I had a company that took off and learned a lot of lessons. And this one was called Run for Your Lives, which was the first ever zombie-infested 5K obstacle course race. Um fun. It it was wild. Like it was, it's one of those things, and this happens in entrepreneurship, or at least where I play all the time, which is like that'll never work, or that's a dumb idea. And when I start getting that feedback, it's like I know I'm on to something because those are people that are close to me and cautious. Um, but generally, like weird stuff just starts to fly, and and you're just super differentiated. Um, so anyhow, that was Run for Your Lives. Unfortunately, learned every lesson in the book on that one. Hired all my best friends, couldn't spell P L, didn't have any system or framework. Um, and so it was just uh it ended in a ball of flames, unfortunately.
SPEAKER_01:The zombies got a got a hold of it, huh?
SPEAKER_00:It was like so anti on brand for that one. Like the zombies actually died, um, unfortunately. Um played in some other things for a while, uh, eventually um launched something kind of similar, some sort of immersive experience, started as event, hunt a killer. Um, we pivoted into subscription boxes. We sent clues items, correspondence, police reports, case files monthly episodically. Um, grew and scaled that zero to 55 million bucks in six years, sold it last year.
SPEAKER_01:And then congratulations.
SPEAKER_00:Thanks. Um, and then of all things got into talent acquisition. And so that's that's what I'm working on today at Talent Harbor.
SPEAKER_01:That's crazy. Okay, so everyone that's listened to my podcast knows when I have a founder on the call, I put them in the hot seat. I would love for you to share a lesson learned, maybe one from the zombies or maybe a different one, but a lesson learned that if you could go back to your younger self, you would tell yourself, don't fall for this, or make sure you do XYZ so you can actually grow the business and not crash and burn.
SPEAKER_00:Yeah, it's um it's a great question. And and I think, you know, the two things that have changed my life number one is uh something called the entrepreneurial operating system. I know you're you're familiar with that, EOS. Um it's based upon a book called Traction by Geno Wickman. Um and the second thing that changed my professional trajectory was Vistage, which is a peer-to-peer CEO group. Um the problem is I didn't discover them until later in life. And so it was when Run for Your Lives bankrupted, I said, if I am ever fortunate enough to find product market fit again, because that's founders out there, like the hardest thing to do is find product market fit. Once you do, cash can solve a lot of problems, it can hide a lot of things, but it gives you time to solve those problems. You have very little time to solve product market fit um because you only have so much runway um uh to get there. So, you know, for me, I said, if I ever find lightning in a bottle again, the first thing I'm gonna do is find a group of peers that have already been there, done that, that can guide me along the way. Um, and then when I joined Vistage, I had an EOS implementer, you know, this might have been nine years ago now, 10 years ago, came through our our Vistage group, gave his presentation, his his half day workshop, and I was like, this is it. And so with EOS and Vistage, it's like it was the difference between zero to eight million in bankrupting and zero to fifty-five million uh with an exit.
SPEAKER_01:Yeah, yeah. I I I I know Vistage, I was a part of them as well. So it is a great, a great community for sure. Well, I appreciate that. Yeah, I think that is one of the things uh, you know, I always work with founders who's like, yeah, I hired all my friends. So, you know, there's some pros and cons to that for certain. But uh yeah, that's uh that's a hard lesson to learn if uh if they're not a the good fit for your growth and where you're taking the business.
SPEAKER_00:Yep, 100%. So yeah. I was gonna say we did this, we did the same exact thing, like hired all my best friends. That was probably that that was one of the early mistakes. And and it's not because they're not good people, like if they're your friend, you trust them, and there's a there's like they already fit the culture because generally who's in your circle is like, you know, probably shares the same values and belief structure that that you have. The problem is that doesn't make them qualify to to exceed or excel in the roles that you have. Um, and so yeah, that's that's bit me in the butt quite a few times.
SPEAKER_01:I will, and hopefully they're still your best friends and friends in your personal life. So that's always the challenge, too, right? Yeah, yeah, yeah, for sure. Uh, okay, so let's talk about recruiting in people. So what's the uh, you know, you've built multiple companies from the ground up. What's the first people decision you think founders get wrong? And you know, maybe this is hiring your best friends, but what is it that you think founders get wrong as they start to grow their business and bring on people?
SPEAKER_00:I I think it it really there's there's there's so many things. And and like it really depends upon the stage and the size. So in the early days, especially if you're not a funded company, because you don't you don't have access to capital, so you're really relying on like goodwill that you have with with people that are in your network and um and relationships that you've built over long periods of time. Um, but like I I promise, like it is certainly if expectations aren't set out of the gate, hiring your friends, generally speaking, always goes south. Um, because inevitably, depending upon the stage and size, and this happens with anybody, right? Like it doesn't matter what human you bring into the business. If you bring someone in at a million dollars and you go to$10 million in a year or a year and a half, that person that was fully qualified and capable at a million may not be the right person at that 10 million. And so, regardless of who it is inside of the organization, you're gonna run into those issues. Personally, I would rather have colleagues and teammates and people that I had hired based upon culture fit and other things to have those tough conversations with versus best friends who there's a lot tied up into the relationship and emotions there. Yeah. Um, so like that's certainly one another one is, and we started to get this when we scaled. So typically people like you and I, big visionaries, like like we're like the company's going in this direction. And when you see it and you know where you're going, you want to hire people that are already there. And I made that mistake so many times. So we were we were probably around a$25 million company um at the time at um at Hunter Killer. And I was like, we're gonna be 100 million in 18 months. Whether that's true or not, you know, that's that's what we've made ourselves to believe. And so I went out and found somebody at a hundred million dollar company that was already running it. The issue with that is that those people, generally speaking, are not the ones that took that organization from 25 to 100 million. They're generally the people that came in because they came in when the organization had the issues and the problems that only they could resolve. And they've got a team, they've got infrastructure, they've got capital, they've got resources available. Yes. And so many times I've hired that person, they come in and they just flail. Were they the right culture fit? Would they have been perfect? Yes. The problem is like what you need or what we needed then and there was someone that like had a lot of experience at a$25 million consumer company and went with another consumer company, say 25 to 50 million. So they knew all of the landmines of like there. Instead, and I've made this mistake more than one time. Instead, we went and found the one that was already where the vision was, and they just didn't know what to do.
SPEAKER_01:Yeah. And I think too, like the key there is maybe finding someone who has been at a 25 and grown it already to 100. And maybe, maybe they're staying on because they're learning and growing and what it means to go from 100 to 500. But ultimately it's that sweet spot of someone who's been there and done that and and may have a roadmap, you know, playbook that they can tweak for what your business is. Uh yeah, we've I've seen it so many times. Uh I've had a client who hired a CMO and uh, you know, the CMO thought, oh, this is great. I'll learn a little bit, you know, be able to grow my own expertise. This the CEO thought, oh, this is great. Someone that's been there, you know, has uh does 100 million and exactly what happened, what you said happened. And the individual, the CMO just was like, Well, I don't have the resources, I don't have, I don't, you know, I don't have people, don't have money, and I'm not really sure how to like make this work because his experience was he had all that in his past life and you know, mutual decision, and they ended up, you know, parting ways. But I was talking to the CMO and he's like, I will never apply for a company that isn't at 100 million or higher because they just aren't gonna set, I'm not gonna be able to help them and they're not gonna set me up to be successful.
SPEAKER_00:Yeah. I, you know, to and thinking about that even further, like maybe maybe the person you're going for at that hundred million dollar company was like on the early team of that organization, but doesn't carry the title anymore. So at Hunt a Killer, we brought in this amazing human. And his first title, I think he was our third hire, and his title was VP of operations. We were three to five million at that point, and like somewhere between 10 and 15 million, operations started to fall apart. And it's not because this guy was not smart, he's one of the smartest people I know. It's not because he wasn't motivated, it's because he didn't know what to do. And so we had to have very tough conversations because he was a culture fit, he could handle those tough conversations. We had those conversations and we moved him into different roles in the organizations. And so he went from a generalist for a smaller company and he started to get into these specialist roles all day long. Like if I were, if I had a consumer company at 25 million, he didn't carry the VP of operations title at that point, but he saw everything and he would be invaluable to an organization to bring in ones that are scaling.
SPEAKER_01:Yeah, exactly. And I think, you know, talking about that first point, uh, when you're if you need to bring on your friends or you think they would be a good fit, and even some of the earlier hires that maybe just through networking and ultimate like open job brecks, it's always good to talk about where you're taking the company, what your vision is, and that, you know, you hope that as the company grows, this individual grows, but there may come a time when, you know, the company outgrows them. And so if you if you set that foundation, I think it also helps not to scare them away, right? But just say, hey, look, your skill set is perfect and you're gonna help me grow this business. And I hope that through that you will grow and we'll continue to grow together. But there might be a time in which I'm gonna need to bring on someone, maybe light layer you, or maybe there's a different direction that we need to go and kind of setting that tone a little bit, especially with the friends, I think helps in that end result because I have yet to see, in my experience, and sounds like from you as well, a time where the person that you had, maybe pre seed or series A is gonna be the same, is gonna still be with you at series D IPO land.
SPEAKER_00:Yeah, it's I I would almost argue it's impossible. Usually the CEOs um are still in those places because they're putting the right team. Like when I think about like what my job is inside of any organization, and like to be clear here, I am not a recruiter, I am not a game designer, I'm not an obstacle race designer or executioner of those. Like my role and my superpower is like identifying opportunities or white space, blue oceans, and pooling together incredible humans to go solve those problems. Um, and so like as a part of that, like I can scale with an organization because what I am, I'm like the the um, oh gosh, it's like the the guy in front of the orchestra. But like I'm bringing the right there, it is conductor. Like I'm bringing the right people in at the right stages, not always getting it right. I'll I'll tell you just like full transparency there. But usually I've got the right team around me to solve the problems. And so like CEOs and founders can sometimes get away with that if they're bringing the right person in, um, you know, to help kind of cover their blind spots. And the CEOs and founders are generally learning the whole way up.
SPEAKER_01:Yeah.
SPEAKER_00:The organization just can't, they can't have, you know, an entire senior leadership team that are all learning together because you're just gonna screw up a whole bunch of stuff.
SPEAKER_01:Yeah, it's so true. Yeah, for sure. So you said before that great teams don't just happen, right? You kind of just said it right there. They're built. What's your blueprint for building a team that can scale and stay aligned?
SPEAKER_00:Yeah. I so it it really starts. You said this earlier of this idea of like uh vision, mission values. Um, in in EOS worlds, um, you know, we call it the the niche, we call it the 10-year target, we call it core values. People have different names for it, but it's all the same thing, which is like, where are we going? How are we gonna get there? And what are the the core beliefs or core behaviors that this organization is going to um set as a gold standard in order to accomplish those goals? There's a lot of people that say that the talent is kind of the foundation to the business. I would actually argue that the vision, mission, and values is the foundation of any business, and the humans are standing on top of that foundation. And the the goal there is to have the right humans. And I guess what I mean by that is like when I've gotten hiring wrong in the past, it generally is not because I can't read a resume. It's it's not that I can't look at a resume and say, oh, this person has the right qualities, the or you know, has served in the right position, has accomplished the right things. And then I can make three or four phone calls of of references and validate the information on on the on the resume. So very rarely do organizations get it wrong because of the resume. They get it wrong, either A, they really haven't clearly defined what is the problem that is being solved by this human. And so taking the time to really understand what we are hiring for, why are we hiring for this, and what are the skill sets that we need in order to accomplish whatever it is that we need to accomplish. Like I can't, I can't like stress this enough. The pre-work that goes into that is critically important. The problem is that most of the time the hiring managers in organizations are the leaders, and the leaders in the organization or managers are already at 110 or 120%. And so it's like no organization ever says, like, oh, you're only at 60% capacity, go hire three more people.
SPEAKER_01:Yeah, exactly.
SPEAKER_00:What happens is you've got people that are overburdened, and then you just throw something else on them, which by the way, like recruiting is a core competency. Someone that's a great operator or a great marketer, that doesn't necessarily mean that they've got much experience kind of building that muscle of recruiting. And so, like, that's often a big problem. And then the second problem is bringing people into the organization that truly don't have the core values that you're looking for doesn't make them a bad person. A person that that could thrive, survive at Apple or Amazon or Tesla is probably not the same person at Zappos or like think about like more fun cultures. Yeah, it some people would look at that and be like, oh, well, that one's bad. Well, that's probably because that person would fit the other culture. Someone else would be like, that culture is lazy. But they're both successful in their own right. They just have different principles that drive it forward.
SPEAKER_01:Yeah, exactly. Yeah. And I'd say, like, too, I think uh sometimes I see uh hiring managers and all levels, right? But hiring managers, like you said, they're so overloaded, they just need to bring someone in that's going to help them be able to get catch their breath. So either they wait too long, right? They're they drag their feet because they are so overloaded, it's hard for them to even put five more minutes on their calendar to take the step needed, which actually just you know compounds their issue. Or they're like, yeah, let's get someone in. And it's like, you know, I've seen I've seen hiring managers just hire the first person they interviewed. I've seen hiring managers rush through the interview process because they just want to get some a button seat, as they say, right? So uh, which does no good thing, does not give you good service at all on both directions, right? Both the individual you're bringing in and yourself. The other thing I see is that a lot of times you kind of called it out a little bit, is that you're not a hundred percent clear on what you need. And you don't spend the time to think about, okay, what do I need today? But what do I also need tomorrow? And that tomorrow could be, I want to grow my revenue five more million, not I want to grow it 50 more million, right? It's like, what do you need tomorrow that may be a little bit different than what you need today? And let's find what that looks like, not necessarily what you need in six months or a year from now. Um, and really understanding that I like to work through the org structure and look at like from an org chart perspective, right? And being very clear and thoughtful about the skills and the structure of the org, not who's in those boxes, right? Like don't put names in and really think about what should your org look like that's gonna help you move the needle and then start putting the names in, see where your gaps are, and maybe who didn't get put on the in a box, right? And and that could help you also with your recruiting efforts.
SPEAKER_00:And I like a lot of this probably depends upon how fast an organization is growing. At Hunt a Killer, I think it was probably every six months we would look at the org chart and we would like you just said, I think starting with a blank, with a blank org chart and just Like the titles and a few key responsibilities is like is is truly incredible. But like we would almost we would white paper this and like okay, where are we at today? Like let's rebuild it. Let's see if we would tweak things. It's it's such a powerful exercise. Maybe it's yearly for organizations that aren't growing, um, that aren't growing as fast. But um, yeah, the the needs of the organization are constantly changing. And if you're not doing that work, that exercise, you probably have a lot of wrong, wrong, uh, wrong people, wrong seed issues.
SPEAKER_01:Yeah, exactly. Especially if you're pivoting your company, you're rebranding, like that. If you're doing any of those, like that is a warning sign. You should be also including the this exercise. Uh, because you know, uh, I've seen a lot of companies who like I had one company who started as one thing, and three years later they're a completely different company. Uh, and so the skill sets needed obviously evolve through that evolution of what they were doing as a business.
unknown:Yep.
SPEAKER_01:Yeah. So uh, you know, most founders either obsessed over product or pipeline, but we've been talking a lot about recruiting. What uh why is recruiting a competitive edge from your perspective?
SPEAKER_00:Yeah. Well, this probably gets to like the foundational point, right? Like the the actual definition of business is this idea or these collection of human beings and like solving problems and and doing so, um doing so for some sort of exchange for value. And so like if business truly is the collection is probably wrong word, the organization. If business at like fundamentally is the organization of people, like that should tell you that people are are everything, right? So it's like if you don't have the right people in the organization, you your organization, you might be making the right decisions, but you are only one person inside of that organization. So let's say it's a 10-person organization, you're making all the right decisions. The next layer below is making 50% of the right direct uh decisions, and then the layer below them is like they're making 25% of the right direct right decisions. Or you might have people rowing in the same direction. It's just like when you want to accomplish something and you want to do something special, you've got to have the right people on the bus. And so I like I I would this is probably not like a hot take or anything like that, but the humans inside of an organization are everything. The reason that recruiting is a competitive advantage, and and this is what we've done, by the way. So Talon Harbor has built something that I wish existed with Hunta Killer. When we sold Hunt to Killer, my vista chair came to me and he said, Hey, he was like, Hey, kid, um, you're not going to be able to sit still. So go pick your favorite line item and go do that for a while. For me, it was people, it was the investment, development, coaching, mentoring, everything people related. We spent a million bucks on recruiting. And I was like, this is the stupidest industry to ever exist. The business model hasn't changed since the World War era. This is this is dumb. Um, and so I called the best recruiter we ever used. She had sold her shop, um, the shop she was using when she was doing our stuff. And she was working at the acquirer company at the point. She was looking for a change. And so she was like, let's do it. And so we joined forces on um on Talent Harbor because what most smaller organizations do, they can't afford 20, 30, 40,000 per hire, 30% of first year compensation.
SPEAKER_01:So expensive.
SPEAKER_00:100%. And so what they'll do is they'll they'll treat this like a oh, but there's job boards. So they'll pay 10 bucks, 50 bucks a month, they'll go to a job board, they'll get hundreds, if not thousands, of resume. They're not expert recruiters, they have no training in this, they have no proven process, and they're just like their heads spinning and they're hiring the wrong people, and now they've got a churn issue inside of the organization. And so the thing here is like what we've done is made expert recruiting accessible to small, medium-sized businesses through a a subscription program, much like Hunter Killer was a subscription. We've taken a lot of that stuff into the B2B world. Um, but the whole idea here is like finding the right people, which isn't posting the job boards, by the way. It's like having access. That's it. It's like it's having access to databases, internal databases, external databases, and then identifying like this person has the exact skill set. They're not on the job boards, by the way, because they're killing it in their current role. Right. And then it's picking up the phone and selling them to take the time to run through our three-part interview, and then our clients, whatever their interview process looks like. So that's real recruiting. Real recruiting is not just posting to job boards, letting AI tell you rank and sack them and and then having a couple calls.
SPEAKER_01:Yeah, it's relationship building for sure. Yeah. And it's uh, it's it's just think of it the same as cells, right? You got to go out and you gotta find the right people that are the right fit. You're not going out and just you know, blanketing the whole world hoping that one of them will turn into your client.
unknown:Yep.
SPEAKER_01:So why are you treating recruiting the same way?
SPEAKER_00:100%. Yeah.
SPEAKER_01:Well, Ryan, as we wrap up here, any last final thoughts or tips or tricks you'd like to share with the audience today?
SPEAKER_00:No, just uh just keep going. I I think you said like you've got a lot of like seed series, um, you know, maybe first-time founders, people that maybe be still searching for product market fit or over, like business is a journey. This is one thing. Like, my first company went bankrupt. I've probably had 30 plus companies, only one has sold out of those companies. Like, entrepreneurship is a journey, business is a vehicle for for you to be able to like accomplish whatever it is. Um, and so it's just a matter of like you just keep going and you'll achieve it. But uh yeah, you just gotta keep going.
SPEAKER_01:That's awesome. Well, thanks, Brian. I hope for those listening, you got some good tips and tricks and uh lesson learned from Ryan. Thanks so much for joining us, and we'll see you on our next podcast. That's a wrap for today's episode of Scaling with People. If you got value from this conversation, do me a favor, share it with someone building something big. And hey, I'd love to hear your take. Drop a comment, shoot me a message, or start a conversation. And don't forget to subscribe so you never miss the bold, unfiltered strategies we draw every week. I'm Gwynberry Quary, founder and CEO of Guide2HR, where we help high growth companies scale smart with people for strategies and AI powered systems that don't just keep up, they lead. If you're building fast and want your HR to move faster, head to guide2hr.com and let's talk. And remember, scale isn't just about speed, it's about people. Until next time, have a great one.
