553 Ryan Hogan

[00:00:00]

Founders And Talent Stakes

Jeffrey Feldberg: Most founders eventually discover that the company they built is only as strong as the people they trusted to build it with them. Ryan Hogan learned that lesson from both sides of the table. He's a navy reservist, serial entrepreneur and co-founder of Talent Harbor. A recruiting company built to challenge, the traditional commission driven headhunter model with embedded flat fee recruiting for growth focused businesses.

Before Talent Harbor, Ryan helped build Hunt a killer into a major consumer brand to nearly $50 million in revenue recognition on the Inc. 5,000 and Fast Company naming Hunt a killer, one of the world's most innovative companies. But Ryan's story is not just about scaling companies.

It's about what happens when the wrong people are in the wrong seats. When hiring becomes reactive instead of strategic. And when a founder realizes that talent is not an HR [00:01:00] issue. It's an enterprise value issue. Ryan has lived the pressure of building, failing, rebuilding, leading under uncertainty, and turning hard lessons into a new model for helping companies find the people who actually move the business forward.

His work sits at the intersection of entrepreneurship, leadership, recruiting, culture, and execution. For any founder who's ever said, why is hiring still so hard? Ryan brings a kind of practical wisdom that only comes from the trenches.

And before we start the episode, a quick word from our sponsor, Deep Wealth and the Deep Wealth Mastery Program. Here's Sanjay, a graduate of Deep Wealth Mastery, and he says, the investment I made in the Deep Wealth Mastery Program, it's a rounding error compared to the value created today and the future value I'll receive.

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Now speaking of growth and adding value, check out what Leon says. He says that the Deep Wealth Mastery Program changed how and who we hire. We've now begun to hire talent today that we never would have hired if it weren't for the program. The talent we're hiring today is helping both increase our growth and profits and our future enterprise value. 

Man, I love that kind of feedback because it's that kind of feedback that's what gets me out of bed every day.

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Podcast Welcome And Guest Intro

Jeffrey Feldberg: Deep Wealth Nation welcome to another episode of the Deep Wealth Podcast. Well, deport Nation, we have a very special guest in the house of Deep Wealth. We have a fellow founder, but not just a founder, a post exit founder who has been there, done that, and is gonna be some really interesting questions.

Maybe some questions that are too real and [00:04:00] upfront for you, but you both nation, you got the thick skin. We're gonna cover anything and everything, Ryan. I'm really excited. To have you with us today, and firstly, welcome to the Deep Podcast, man. You have quite the journey. You have quite the story, so what's your story behind the story?

Share with Deep Wealth Nation what got you from where you were to where you are today.

Ryan Origin Story

Ryan Hogan: Yeah, sure. First foremost, thanks so much for having me. Appreciate it. and I'm sure like most entrepreneurs out there, like there isn't a straight line in my story. It's interesting 'cause I could draw. Probably a, line from selling creepy crawlers in third grade to now being in the talent acquisition space.

And it's really been just kind of all over the place. But my story is really about two different kind of professional trajectories. Number one is the United States Navy. So I was active duty for 15 years. Now I've been in the Reserves for the last nine years. For me that's really a way to give back. Because the Navy and the military just gave me so much I was very much a lost soul. I was searching, I had the grit, the tenacity, I [00:05:00] had the drive, I had all of those things, but I didn't have the discipline. I didn't have the focus. And that's really some of the biggest lessons learned that I had from the military service.

And then on the entrepreneurial side. For me the first company that really achieved some semblance of scale was a company called Run for Your Lives. It was a zombie infested five kilometer obstacle course race. So if you remember the tough Mutters and the Warrior Dash and the Spartan races they wound up getting all the press.

But we had this little event that had grown very rapidly. We did 23 events across the country one in Canada in 2013. But that ended in a disaster. And that was really my first experience With entrepreneurship and making sure you have the right people on the team, making the right decisions, the right focus because we had none of that.

Fast Forward took about three years off that company, unfortunately, bankrupted, it also took me down because I didn't know what personal guarantees were. I was signing everything. So when the company failed, I also landed on my [00:06:00] face. Took about three years off his relative. I was active duty at the time, had that going was still launching different concepts, different ideas. But the next one that took off was called Hunt a Killer. And that is an immersive murder mystery experience. We started off as a live event. We transformed a 200 acre campground into a living crime scene and what we found was that we found product market fit, but we didn't have a business model that could scale.

So two weeks after the first event, we iterated or pivoted into the subscription box business model. And we wound up taking this immersive murder mystery experience directly to people's doorsteps. And it was clues, items, correspondence, police reports, case files, things like that. We scaled that from zero to 48 million in about three years.

And then we added retail, got to 55 and then wound up selling it two years ago. And then of all things got into talent acquisition, tried to take a break, took six months off, was also activated as a reservist in [00:07:00] the military at that point. Didn't waste any time and, jumped right back in.

Jeffrey Feldberg: Yeah, my goodness. So much going on there and absolutely love whatsoever. And by the way, GPO Nation watching Orion is being very modest with some of the things that he's done. They had all kinds of awards and accolades on the Inc. 5,000 list and fast company and being named one of the world's most innovative companies.

So he's been there, done that. 

Navy Service Lessons

Jeffrey Feldberg: Before we talk the business side, let's go back to the Navy and again, offline, I was sharing. Big thank you on behalf of Deep Wealth Nation, the sacrifice and the service that you did for the country to allow us to do what we do. When you were doing what you were doing. Not that this is a political podcast, it isn't, and we're gonna say it to the geopolitics.

Lots of that that's going on today. Talk to us though about life when you're in the Navy now as a Navy reservist of what that meant for you, because it seems that politics is skewing what that's about, and these brave men and women that are defending our country and our [00:08:00] values and our way of life, and really making a difference out there because it's not unfortunately, not necessarily the nicest world out there once we leave our borders. So what was that like for you back then? Has it changed much? What's it like today as you look at it from today's landscape?

Ryan Hogan: Yeah, there's definitely been an evolution. When I joined in 2002 this was post nine 11 era. And you think back to the Vietnam era and soldiers that were being spit on and there was this, big riff between civilians and military personnel when I joined.

Everybody was all about the military because of the events that had transpired. And that stuff has certainly evolved over the years. And the big thing with. the military is we're apolitical, meaning what we do is we follow orders. we are an instrument. We are a tool in the tool belt for civilians.

And that's really it. As things escalate and they come down, they go up it's not even really our position to get involved. It's really just about, serving each other, [00:09:00] serving the country and, doing the things that need to get done.

And for me, what needs to get done is we need to take care of our sailors, our soldiers. And that's why I stay in when I joined. Back in 2002, I was lost. I got into trouble almost less than a year. I was an E one twice. And so for anybody's listening that means I went to Captain's mast maybe two got knocked down to E one.

And that's where things really started to change for me. And it's because people. Poured into me. People saw something at that point in my life that I didn't see, and something just clicked. And so one of the biggest reasons that I continue to serve today is to give that back. If I can have an impact in one junior sailor's lives, if I can inspire or change or help in any capacity, I feel like it's my duty to do because of the people that have done it for me.

Yeah, it's something that's very deep and meaningful for me.

Military Skills In Business

Jeffrey Feldberg: And as you look back so that you can look forward when you founded your company and you're coming off of [00:10:00] now doing the service. How did your time in the Navy, did it affect how you started the company, ran the company, grew the company because you're successful even though the first one may have blown up and you learn some things along the way.

Show me one person that hasn't made a mistake and I don't think that exists. So when. You've got your success, and at least in my books, success is not an accident. It's very deliberate and it just doesn't happen. You don't wake up one day and, oh my goodness, look, I have a successful company. So what contributed to that success that you can look back to your time in the Navy and say, yeah, you know what, this ritual here or that discipline there, or this experience over there that really helped make a difference?

What would you say to that?

Ryan Hogan: Yeah there's two big things and one was a byproduct of being in the military and the other was more intentional. That comes through training and, things like that. So number one, I think what every entrepreneur. Needs is resilience. there is not a successful entrepreneur out there that doesn't have high resilience.

And how do you build resilience? [00:11:00] You face adversity and you continue to go through and every time you, hit a wall, you get back up. Every time you get punched, you get back up. that's really entrepreneurship and in a nutshell. And so I think for me it was really about.

Everybody looks at the military as like this perfect force, like flawless execution. And it's not that, accidents don't happen and things like that, when people think about the military, they think about the best of the best. And. the way that we become the best of the best is through training.

And what is training? Training is an opportunity for us to fail. So what the military is actually doing before they ever go and actually execute a mission is they are failing and they are failing day in and day out. They're making mistakes and they're doing that in a controlled environment to be able to go down range and execute flawlessly.

And so what's interesting is like the perception of the military as this. Almost perfect force. Perfect force in the execution. Not necessarily perfect in, things that are happening, but what that is a lot of failure leading up to that. And what [00:12:00] that does is it builds resiliency because if day in and day out you're training, your training, you're learning, you're improving, that builds the resiliency.

I think the resiliency was a direct result of the military. The byproduct, which only came to me recently was just the idea or the circumstances of the military. When I started companies, I was always active duty. Every company that I've started, even Talent Harbor, I was activated on as a reservist.

I was on active duty orders when I launched Talent Harbor. Every company that I've started, I have been active duty and. What that does is it forces you to delegate. There is not enough time to do what you need to do to be successful in the military and also micromanage a business. And so what the military did as a byproduct of being in is it forced me to delegate and almost become removed.

most founders. I have too much trouble holding on. And what I get coached on from my business coaches is this idea of [00:13:00] abdication. They're like, Hey you've, let go too much of these areas. You need to go pull 'em back. I would argue that, that's how we've been able to scale as fast as we have in all of my companies, is because I get outta the way and let the right people make the right decisions.

Jeffrey Feldberg: So much there to what you're saying and so much that we can unpack and you're absolutely right. For most founders, and I'm guilty as charged, I was the company. The company was me. By the time I realized, Hey Jeffrey, it can't be like that anymore. I had. Paid a price, emotionally, physically, mentally. By the time I put a leadership team in place, Ryan, we were already heading into market and the team was in place.

Amazing team, by the way, world class team. I was dealing though with world class buyers. They do this all day, every day and they all pulled me aside and said, Jeffrey, we love your story. Love your company your team's. Amazing. But come on, what do you think? We're born yesterday. As good as they are, they've been in place for a little over a year.

And as great as your company is, we're [00:14:00] gonna have to penalize you for that because, well, because they could even though we had an auction and we had hundreds of companies that were all chomping at the bid, if we didn't have that, by the way, Ryan, it would've been a whole lot worse. But they were right on what they were saying.

I gotta own it. Of we don't really know what these guys can do under pressure. Sure, a year is fine, but we would love to see. Three years in the seat or five years in the seat to really get a, a test of what they and, and the company can do. And I'm wondering, I could be off base with this. I don't think it's.

Coincidence, or you just happen to start Talent Harbor just for the sake of starting a talent company. I know often I said, Jeffrey, I don't really wanna talk about Talent Harbor. I wanna talk about my journey. You're a very, again, modest kind of fellow, but let's talk about the talent side because I agree and I've made this mistake myself.

I, as I like to say, and we say here at Deep Wealth, when you go through Deep Wealth Mastery, either delegate, automate or eliminate. Now, what's not a fourth option that I've done all too many times and so many founders do [00:15:00] is abdicate. And that's where, Hey Ryan, nice to meet you. Here's the area. Here are the goals.

Good luck with it. I'll check in with you this time next year. Lemme know how it goes. And that's probably just as worse as being a micromanager because you have the two extremes. So let's talk about talent firstly before we go into Talent Harbor and what's there, even though you don't wanna talk about that.

Right People On The Bus

Jeffrey Feldberg: Being in the Navy and then scaling incredibly quickly. These companies while you're active duty, what did you learn about talent and what did you have to unlearn about talent when it comes to running a company, I.

Ryan Hogan: Yeah, it, so Talend has been the key and there's a lot of components to the business. There's what the business does, there's the strategy, there's the task, there's the goals, there are so many different components to the business. My biggest lesson learned and this was through Run for Your Lives, is you need the right people.

If you have the right people on the bus. And there's a, a great book, good to Great and this is where I first explored this entire concept, but it's like you get the right people on the bus, you get the wrong [00:16:00] people off the bus if you have the right people on the bus. Everything else takes care of itself.

And you don't have to micromanage. You should never abdicate. That's something that like a huge mistake and lesson learned on my end. But there's a way to look at the right things, whether that is metrics or tasks or whatever it may be. You can look at that stuff on some sort of frequency, a weekly, a quarterly, an annual basis, and understand what the performance is.

But if you have the right people, then everything else is taking care of itself. If you have the right people. Then from a strategy standpoint, we actually just had this lesson learned at Talent Harbor where we've been solving all the big problems and we've started to hire, 'cause we're growing at Talent Harbor and we're like, wait a minute.

Like we didn't even have to solve, we used to solve. A hundred problems, and now we're solving 60 problems and they're being solved because we have the right people with the right expertise. Number one, they're being solved at a more elite level because these people are more experienced in their competencies or in their domains than we [00:17:00] are.

And they're happening without our intervention. And so the biggest epiphany, was like, it's all about talent. The problem that I think most companies have is that finding and vetting talent is the hardest thing an organization can do. And I didn't understand that until I hired.

Many wrong people. And, then we were able to afford, eventually, I think we were maybe 10, 15 million and we could afford to go out and get an expert recruiting firm. And I was like, who are these humans? They're bringing through the door. Like, you know, I used to look at a hundred resumes and I was like, oh gosh.

Like I, I don't know. And they look okay. And then I would get these resumes from expert recruiters. And I was like, holy crap. And it was based upon. Where are they looking? How are they vetting? how are they getting 'em through the door? And it's just something that I always underestimated, which is why I am in the talent business today, is because I think most business owners think a recruiter or recruiting is the manager's job. It's the sales manager, [00:18:00] it's the operations manager. Well, there are recruiters that have spent just as much time learning the craft, the art, the process of recruiting that an operations manager has learned, operating a warehouse or making the supply chain more efficient.

And it shouldn't be taken for granted that they are also expert recruiters. I think that's where I got it wrong in the past, that's one of the reasons we launched Talent Harbor.

Jeffrey Feldberg: And at the risk of asking a deceptively simple question on the surface, not to confuse simple with simplicity, and you can go in any which way. And you'd be perfectly right to say, well, Jeffrey, my goodness, every company is different. Some of my biggest mistakes, I hired people who did the best sales job if it was a sales.

Position. They did the best sales job in the interview and that was it. It was downhill after that. But I got so impressed and if I'm gonna be honest, I was a founder. I am a founder. Busy, don't have a lot of time for this. Yeah, they look good. They have a great smile. They made me laugh a few times. Ah, I'm sure they're good.

Let's give 'em a [00:19:00] shot. And off we went. With that is like rolling the dice. Or you could have put a whole bunch of names on a dart board and just throw the dart. Probably would've done better than how I did. What would be, let's take the opposite of the glass half full glass, half empty. What are some telltale signs when it comes to talent?

When you look back at your companies, for the ones that worked, for the ones that didn't work with the talent and what you're doing right now with Talent Harbor, what are some of the telltale signs that, Hey, you know what, something isn't right here. Run. Run as fast as you can, the opposite direction. You don't wanna bring this person on board with a team.

Ryan Hogan: Yeah. 

Culture Fit Red Flags

Ryan Hogan: There are a ton of things and I'll say. When I thought I was good at recruiting, I thought recruiting was just looking at resumes, being able to identify and then, asking a few questions and, really just getting a feel for the person. And that's not a good recruiting process.

Number one, anybody can read a resume and decide okay, this person has industry experience. They accomplish the things, or at least they said they accomplish the things that we need. Of course, they're gonna be a great fit. Every time that I've gotten hiring wrong, it's been based upon the culture fit.

[00:20:00] I've brought the wrong human into the organization. And it doesn't mean that they're evil. It's ev, they're, every company has a different culture. And that culture is what are the actions or the behaviors inside of that organization that drives success And generally speaking. It's not right or wrong. Not many people are malicious with creating whatever their culture is.

It's just the culture. It's how they think, it's how they behave. And every time I've gotten it wrong, it's because I've brought the wrong human through. And so one of the things that has to be of. Like center focus is who is this human being and what makes them tick. You brought up a great point about people being able to sell themselves.

We focus on sales recruiting, which is the absolute hardest because I would say almost a hundred percent of salespeople can sell themselves. That doesn't translate in them being able to sell your product or your service. And so there's a lot of tactics you can use. One of the ones that we use is we get [00:21:00] that human outside of their element.

When you show up to a Zoom interview where you show up to in person, like you are going to see as the hiring manager, you're going to see the face that they want you to see. And so being able to get them out of their element, whether that's. They come in for an interview, they think they're gonna sit down, they put their note sheet, they've got their folder with their resume, and you say.

Hey, it's a beautiful day outside. We're gonna go for a walk and you go for a 45 minute walk. Being able to get them outside of their element so that the mask comes down and you're really connecting at a deeper level is incredibly important. And then also like really starting to stress test some of the things that they're saying.

And so if you're going down the path of. Of, for us, our number one core value is go givers, which means we've got this belief that we just give with zero expectation of reciprocation. And that's in everything that we do across the team, across clients, across prospects, anything we do, it's all about go givers.

And so being able to ask questions [00:22:00] around that topic of Hey, what are some times in your professional career. Where you've given and then when you get the answer, it's all about three stages. It's all about three layers. And what you're trying to do is go as deep as possible because you're looking for does their face light up?

Can they give like very specific detail about that example that they're giving? These are all the tips and tricks that, that come with recruiters that have been doing this 15, 20 years.

Jeffrey Feldberg: Yeah, my goodness, there's so much there. It's really part art, part science, as we're looking for certain things, and I would imagine today in the offsite, in the virtual world, is even that much more difficult. And we've heard these horror stories of these companies hiring these people, wasn't even the people that they were hiring.

It was a fake picture and a fake resume, and now you add artificial intelligence into the mix. My goodness, that's a whole other topic, a whole episode in and of itself. Let me ask you this though, and we'll go back to your company experience and also what you're doing at [00:23:00] Talent Harbor when it comes to some of the things that I should be looking for that I'm probably not doing as a founder.

Hiring Mistakes And Gut

Jeffrey Feldberg: Ryan is a good old Les Law. It's a fancy loss. 80 20 principle. Yeah, Jeffrey, you know what? 80% of your hiring mistakes where you're failing are coming from 20% of these areas over here. So Ryan, are there some patterns? What are these areas over here? The 20% that most founders are making the same mistakes that are creating, and it may not be 80 20, it could be 90 10, 95, 5.

We'll go with 80 20 for now. Yeah, Jeffrey, 80% of the mistakes are coming from these one, two, or three that comprises 20% of these issues that were just not getting it right As founders when we're hiring.

Ryan Hogan: This one's a bit controversial 'cause people don't want to hear this. 80% of the mistakes are coming from their gut. And what I mean by that is when they sit across from somebody, when I sit across from somebody. We're looking for the way that somebody makes us feel. Does this person make me feel [00:24:00] good?

Is there chemistry here? And what that does is it reinforces the gut that this person's it, and you'll start to overlook everything else. If this person makes you feel a certain way and your gut's I need to hire this person. When you see some red flags or you ask some questions, you'll convince yourself of.

you'll justify why that might be true. And what's interesting here is like when a mistakes like that is made, generally it ends in some sort of separation and. What I have found over the years is that at a point of separation, all of your gut is now or, or your, the red flags that you saw, that you justified are all confirmed based upon that moment.

If someone is professional and they get up and, hey, I know this wasn't working out. You were giving me great feedback. I just couldn't meet those expectations. Great people that get up, start throwing stuff, cussing, go on Glassdoor and start writing stuff, you're like.

Every time that's happened to me, I'm like, I saw that on day one, but they made me feel a [00:25:00] certain way. I went with my gut and I justified some of those red flags that I was seeing in the moment.

Jeffrey Feldberg: Yeah, it's a good old God, and hey, I'm all about intuition and things like that. At the same time, I know the human condition. We're wired that we want to trust, we wanna take things at face value, and. It reminds me, Ronald Reagan, sure, trust, but also verify. And being busy or not really knowing what to look for, it doesn't always work out or we just have our own narrative.

We want it to work out. I'll remember this one particular hiring, I'll never forget I was speaking to the reference. You know, We all know when you get a reference, of course they're gonna be saying good things. It's the reference you wanna speak to that you're not being provided. But I went along with a game plan and I found it odd or peculiar the way this particular reference was talking about things very slow, very deliberate, was asking me questions to make sure.

They understood exactly what I was being asked. It was just a weird kind of conversation. [00:26:00] Anyways, it was the absolute wrong hire. And looking back, I said, yeah, all the red flags were there, and I should have known what the reference. They were too careful in what they're saying, and they were emphasizing and reemphasizing things that in a normal conversation you just wouldn't hear.

But I didn't want to hear it. I didn't want to see it. I already made up my mind I was gonna hire this person and I. Cherry picking what I wanted to see. 

Talent Harbor Model

Jeffrey Feldberg: So take us behind the scenes for just a moment now in terms of some of the magic with what you're doing at Talend Harbor. There's so many choices out there today.

Why Talent Harbor, by the way, love Harbor and the tie back into the Navy theme with you about what's going on at Talent Harbor. That's different that, hey, Jeffrey, as a founder or even as an established company, you got a gazillion people talent harbor. We're different. Here's why you wanna be speaking with us.

What's going on there?

Ryan Hogan: Yeah I think first and foremost what I found about the recruiting industry. There's a significant lack of trust and transparency, and there's this correlation between the recruiting industry and the used car sales industry. [00:27:00] And what I saw was an opportunity in a pretty substantial market to bring trust and transparency back.

So if you think about the used car sales process, the reason that CarMax and some of these other used car wholesalers exist is because. It's no haggle, it's trust, it's transparency. You can see everything. And that's why they exist and that's what we saw when we started Talent Harbor, is how do we bring trust and transparency into an industry that's really been lacking it over the last 50 to 60 years?

The first thing that we did is we looked at the business model. And so every time that I made a hire, I was cutting a 40 to $60,000 check and I was like, that's pretty dang expensive. And what we found is that. The business model, this whole quote-unquote contingent business model makes a sales cycle that doesn't stop until the client hires.

And what that means is even if they've got your contract your signature on a contract, they are still selling you until you hire somebody. [00:28:00] So every time they put a candidate in front of you, they're trying to sell you. Why is that? Because they don't get paid unless you hire the candidate. The business model itself is misaligned in the incentives.

And so what we do is we've got this trust and transparent, and we call it recruiting as a service, but it's a flat monthly fee. There's no contracts, there's no success fees, and there's nothing hidden. And when you need us, we're there. And when we're not, you put us on pause and our whole philosophy is, if we're doing good work, you're gonna stay longer.

You're gonna come back. We're gonna be the first person you think of when you say, Hey, I need to find a new a new human. 

Sales Recruiting Differentiators

Ryan Hogan: Number two is we focus on sales roles. And so we were talking a little bit earlier about sales roles, but sales roles are the hardest to hire for like. everybody brings a certain face to an interview.

Salespeople can sell themselves. And so being able to hunt salespeople, which is this idea of the best salespeople are generally hired and not hang around job boards, so we've gotta go find them, and then we've gotta [00:29:00] run our own sales process to convince them that your opportunity is better than the one that they're currently in.

And. That's a big way that we stand out is we are actively going after passive candidates that aren't necessarily on the job market. And then we've got a 60 day, guarantee. So, there's a lot of things that we do different process, business model, but ultimately it's about making expert recruiting accessible for small, medium sized businesses.

Team Success Reflection

Jeffrey Feldberg: And an unfair question, I'll ask it anyways. Let's go back to your successes with your own companies. Generally speaking, not well. Yeah. Jeffrey, in the sales role, it was this or that, or in the operations? Generally speaking, when you look back, well, the company was successful. I had this terrific team. Okay.

Winning Team Traits

Jeffrey Feldberg: What does terrific team mean? So in terms of the talent that was on that team, what were some of the attributes that looking back made a difference for you? Or I can even frame it in a different way, if you didn't have those people, those attributes. We probably wouldn't be talking today. It would [00:30:00] not have been a success.

It would've gone in the other direction. So what's really worked for you from a talent side of things?

Ryan Hogan: Yeah, what's worked is, has really come down to two things. One, people that wanna win and they don't wanna win at the expense. It's not as. Zero sum win, meaning that they win or the company wins at the expense of something else. They wanna win and they wanna win in a collaborative environment.

They're humble. they've got humility and they're just looking to grow. one core behavior. A core value that I've had throughout all my companies and admittedly it's my favorite is growth mindset. And growth mindset. Is this idea or notion that. We're all on this journey together, and we're all learning, and we have a certain tolerance for failure because we believe that if we're gonna accomplish the big goals that we have set forth, that there's gonna be some bumpy times.

And so number one, it comes down to culture fit for the organization. And again, that's different for most for me, it's always been humble, hungry, eager to win and eager to do that in a [00:31:00] collaborative environment. 

Culture Fit vs Expertise

Ryan Hogan: And then on the other side, it's expertise. 'Cause when you just asked me, you were like, about some bad hires or some poor hiring decisions. my team at my first company, they were all in. They were all into the mission. They were all into, let's go win, let's go dominate this industry. Let's change the world. But they didn't have the experience or expertise. And so both things are needed. And that's mostly 'cause I hired all my best friends from high school.

I was in my. Early to mid twenties. And so they had that attitude that we needed. They didn't have the experience or expertise, so the decisions that we were making as an organization weren't the best. Yeah I would say it's 50 50 on that.

Jeffrey Feldberg: Yeah, it's interesting you're talking about culture and again. As I look to the nine step roadmap, when we have founders go through the Deep Wealth Mastery program of the nine steps Ryan, step number two is X-Factors. What's an X-Factor? And X-Factors is what it sounds like. It's something that is world class and unique to a particular company.

So your competition with all their money, even though they may be so [00:32:00] many times bigger than you, all their successes, as great as they may be, they fail in comparison in this one area. One of those areas is culture and culture. At least for us at Deep Wealth, it's like our fingerprint. It's unique. Each company is different.

And all the money in the world that the competition has, they cannot replicate your culture. So back to what you said, culture's important, having the people with that, right? Mindset's important, but then you finish a sentence where we usually stop, for most founders, it's okay, yeah, they have the right mindset, but do they have the ability?

Do they have the experience? And so talk to us about that. That's some hard lessons learned on your side, being in the trenches. Talk to us about that. Of what you want other founders to know, who they may be going down that path that Ryan 1.0 was going down. You didn't know any better at the time. It wasn't your fault.

It was really, I just didn't know. I didn't have the experience. Well, now I'm wiser, smarter. I've lived through that. What would you tell founders as they begin their journey early [00:33:00] on?

Hard Hiring Lessons

Ryan Hogan: there's actually Two big lessons learned, and there's like a 1.0 and a 2.0. The 1.0 I, I think, in retrospect was pretty obvious, which like there needs to be some sort of expertise or some sort of experience or background, successful background in order for someone to lead a team, lead a department make the right decisions.

And so. You know, my first company, again, hired a lot of people that were motivated and inspired and hard charging, but we just weren't going down the right path because we didn't have the experience, the know-how. They didn't have the capability or the ability at that point, and we just didn't have time to train people up.

that was a mistake that I mitigated for my second company. However, I made another mistake for my second company, and this came as a huge surprise. I've always been driven and ambitious. And so like when we're doing something like, it's about like how can we be the best and how can we be the biggest?

And a big part of that is making sure that you find the talent that's been there, done that. 

Corporate vs Startup Mindset

Ryan Hogan: And so when we were, [00:34:00] operating Hunt to killer. We were probably maybe 25, 30 million at the time, and we needed to hire our first COO. And when I was thinking like, Hey, we're an entertainment company, we're intellectual property, there's a lot of different places that we can take this intellectual property.

What am I thinking? I'm thinking I'm gonna go find that person that is at a billion dollar company and I'm gonna bring them into my organization and they're gonna help us go from 50 million to a billion. I could not have been more wrong about that. What I discovered and, I'm sure I'm not alone in this, is that.

There's a very big difference between a $50 million company and a billion dollar company. It could be the resources, the strategy, the data, like you name it. There are huge differences. One of those differences is they make the decisions, but they don't necessarily do the work. And a $50 million company, everybody's doing the work and everybody's pitching, everybody's rolling up their sleeves.

while the people may have the know-how, the know-how that they had wasn't the journey from 50 to a hundred million. Which is actually, if I could go back, what I would do is I would find that person [00:35:00] that took a company from there to here you know, then you find somebody from a hundred to 500 million, then 500 million.

But you're looking for the people that have actually been there, done that, not the ones that are already there, because the corporate mindset is much different than the startup mindset. And gosh, that was unexpected. And I learned a very painful lesson on that.

Jeffrey Feldberg: Oh my goodness. You're taking me down memory lane Ryan, on that. I have a quick story for you. In Deep Nation, a very close friend won't name names. He said, Jeffrey, let me tell you about my cup of coffee and how I knew I hired the wrong guy for president of my company. And I said, yeah, sure, but what is coffee?

Have to do with hiring the wrong guy to be president. and I'm making up some of these numbers, Ryan, I forget the exact amount. I'm not gonna be far off. Jeffrey. When I was running the company, a cup of coffee was around 25 cents. You know, You just walked up and we had these pods and you made your own coffee, and that was it.

The company was getting too big. I knew I had to bring on a president. This guy had all the accolades in this big company at Fortune 100 and [00:36:00] was looking to make a difference. I thought my company would be perfect for him. He's been there, done that. He'll show us what to do. Jeffrey. I almost lost my company.

Well, what happened with was the coffee have to do with that. Well, I began going through our expenses because we went from being hugely profitable and we started losing money and one thing jumped off the page for me. It was. The coffee expense. And I said, okay, continue. We went from 25 cents per coffee to over $3 and 25 cents per cup of coffee.

And I said to myself, speaking as my friend, if it's that much over here, a gazillion percent increase over here. What else is going on? Is this why we're losing all this money? And it wasn't the coffee that put them near outta business, but it was that corporate mindset. Exactly. To your point, Ryan, and I've made that same mistake.

I found as talented as the corporate people are, and I can't do what they do, not any day of the week, including Sunday, but as talented as they are, they need an organization that has layers and has the infrastructure and the people. [00:37:00] You put them into that scrappy startup mode. It may work out, it probably isn't going to work out more times than not.

So I'm absolutely with you on that in terms of what you're sharing with us of, of what to look for and what not to do. And so when we're looking to scale the company and get to the next level, how far above from where we are do we look to when we're bringing other people in? So as an example, let's just use round numbers.

If I am at a million dollars and I eventually I want to get this over a hundred million dollars and then beyond. Am I going from 1 million to 50 million? Is that too big? Is it the 10 million to 5 million? What are some of the increments where, okay, it's right on the cusp of where it might be a little bit too small for that person.

It's certainly not too big, but it's enough there that I'm gonna get some terrific traction here with whoever I'm bringing in. Thoughts about that?

Scaling Inflection Points

Ryan Hogan: Yeah. There's these weird inflection points in companies and there's different problems at all of those inflection points. And like what I can speak directly to is the consumer product space. [00:38:00] We were primarily direct to consumer via a website. We got into retail, target, Barnes, Nobles, Walmart.

Then there's different complexities across the spectrum. But what I have found true across three or four different startups is like. one to five is kind of a phase. Then you've got five to 10 is kind of a different phase. Then you've got 10 to 20, 25, got 25 to 50, 50 to a hundred. I haven't been over a hundred yet I won't speak too much to the inflection points past that.

Here's the thing though, is. The philosophy that I adopted was I will take a manager. So somebody, let's say it was an email marketing manager. I will take an email marketing manager. That went on a journey with a company, let's say we're going through that 10 to $25 million inflection point.

I'll take an email marketing manager that was at another company from that 10 to 25, and I will put them in a significant position inside of my organization because like they've [00:39:00] seen it. they know where the landmines are, they know the challenges that we're gonna have and the contributions that human can make based upon the experiences that they lived through those inflection points at their last company.

And I've done this in the past of I've taken a, an email marketing manager and I've made them a marketing manager I've put them over maybe three or four different focus areas in the organization. I've taken a, a marketing manager in. And made them a senior? Actually no, we made them a director.

So I took a marketing manager that, went from 25 to 50 and I made them a director of marketing at Hunt. A killer. So like the one thing I don't wanna get lost in here is just because they went through that journey doesn't mean you need their chief operating officer that went through that journey because everybody experienced it on that small team, and there's so much opportunity with the people that might have been a little bit below and now the value that they can contribute to your organization at a higher level.

Promote Within or Hire Out

Jeffrey Feldberg: And it's an unfair question as you're talking about this. I'm gonna ask it anyways. It's that push and [00:40:00] pull of, okay, do I hire from within? So do I take someone who's maybe a number two or a number three, and now put them into the number one position and I have the advantage. They know the culture. I know them.

They have the track record. They don't necessarily have the experience, but they have all the other things going for them. Or do I go outside? They certainly have the experience, but it's an unknown in terms of the culture and how they're gonna fit, and I don't know what I'm getting. I don't know their skeletons in the closet just yet until they come on board.

Thoughts about how we look between the two and figure out the best way?

Ryan Hogan: Yeah. For us, it's always look internal first. If they share the mindset, you can develop those capabilities. this has definitely been a philosophical shift for me over the last probably 10 years, which is if you've got somebody that's hungry and you've got somebody that's willing to learn, willing to grow, you can pour into them.

So they may not have the ability at that point, but if they get it and they want it, being able to [00:41:00] place them in a role like that where you can now bring in an outside consultant and bolt someone up because the reality is. Is that anytime you bring a new human into your organization, it's like bringing a foreign body into your body.

And it may be helpful or hurtful, meaning like it may be penicillin and it's gonna, eradicate everything, but at the end of the day, it's not gonna be exact. And so the cultures, the values, the belief structures of any new human that you're bringing into your organization, it may align pretty good, but it's never going to be a hundred percent.

So there's always going to be a change. A slight change in the culture. Your hope is that you brought them through this vetting process. And so the hope is that you're improving your culture, but that's not always the case. And so whenever you're bringing a foreign body, there's a certain amount of risk.

So what we tell even our clients is like, Hey, before you bring us on, see if there's anybody inside the organization, you can. And then build them up. It may be leadership and management skills. Great. There's amazing programs out [00:42:00] there to build people up into leadership and management. Maybe it's actual competency.

So maybe like they've had the purview of social media marketing but they don't necessarily know paid advertising. So is there an agency or a subject matter expert that you can bolt on a fractional basis to bring this person up to speed? There's a lot of different ways to do it, but that's always the.

Our first advice there is can you grow the people internally?

Jeffrey Feldberg: It's some great advice and it's the human condition. We need to get past your never profit in your hometown. We know the person, we know what they're all about, and we can. Perhaps diminish what their capabilities really are. Oh, yeah. I've known Mary, she's been here for seven years now, and we go back perhaps to the early days.

We don't really see who Mary has become and the value that she brings to the organization as opposed to a complete stranger, oh my goodness, look at what they bring. And then, oh, well, maybe the grass isn't as green on the other side like I thought it was. So it's some great insights there. 

Exit Ready Operations

Jeffrey Feldberg: Let me ask you this because after all the deep podcast and we talk [00:43:00] about exits, in addition to growing the business, looking back with your exits, your experience of, okay, I've grown this company, it's now time for me to move on.

In one instance, you didn't necessarily have the choice, it was is put upon you. At times, yeah, it was by choice. Looking back to your exit. Is there advice or insights that you would give to the Deep Wealth nation for them as they're thinking to either raise capital or take some chips off the table, or a full exit of either some things that really worked well for you, or, Hey, be weary of this.

Don't do this when it comes to your exit.

Ryan Hogan: it goes back to a lot of what you've been saying, which is. The value of a business should never rely upon an individual or a human inside of that business. It should rely upon the systems and the processes and the competencies of that organization as a whole. And we were very successful with this, with Hunt Killer, and we didn't know what we were doing with Run For Your Lives [00:44:00] but.

Implementing process. And, you don't have to think that you're going to sell it, but building an organization like you're going to sell it is the most important thing that a founder can do, even if you're not, because worst case scenario, the business can operate without you. And now you can go sit on an island and drink mojitos if that's what you choose.

You, buy your freedom through those systems, processes, and putting the right people in the right seats. But what I see. even recently, I've looked at a few businesses and what I realized is like there was like one or two key things where if you remove those, there is no business.

And if that's the case, you're not gonna maximize enterprise value. And yeah, everything else is pretty standard. Run a process, get as many horses in the race as possible, put together a great story, reach out to the right strategics. But you can't do any of that if you don't have a business and you don't have a business.

If you remove yourself from the business and the business collapses.

Jeffrey Feldberg: Some great advice. It all goes back to the team and the caliber of the team and how long they've been in the seat. And my favorite question, [00:45:00] anyone who's starting to go through Deep Wealth mastery, first question. Hey, Jeffrey, does the business run without you? Yes or no. It's one or the other. It's a binary answer, yes or no.

No in betweens, no stories. Rarely. Ryan, do we get the yes or no? It's usually the story, which is more times than not. No. And as founders, we really gotta get beyond that. 

AI and Recruiting Reality

Jeffrey Feldberg: My goodness, when it comes to ai. We don't have enough time for all the questions that have with ai. Very high level though. For those in Deep Nation who are thinking, well, hey, this AI thing, I'm going to use this to help me find my next hire.

Who needs a recruiter? Who needs the Talent Harbor and Ryan's team, I'm just gonna do it all with AI by myself. What would you tell that person in Deep Nation who's saying that narrative to themselves?

Ryan Hogan: Yeah, there's a funny quote. So last year, perplexity, CEO came out and he was like, the first two jobs that my AI or AI is going to solve is number one assistance and number [00:46:00] two recruiters. And that's going to happen within the first three months. And I went to Perplexities LinkedIn page at that point.

And they had I think like 120 job postings and out of those 120, there was about 20 for recruiters. And so I had a funny post and I was like, if you're eradicating recruiters from the talent acquisition process, why are you hiring 20 right now? I. The reality is, is that recruiting will never go away.

I wouldn't be in this industry if recruiting were gonna go away. And the reason for that is recruiting is a human process. You're hiring a human now when you have so many jobs available and, and maybe you're at a certain place in the market. So for instance, my son last week applied to Chipotle and he went through this AI interview process.

Chipotle is getting thousands of applications a day, and they need a way to do that. But that's not finding their manager, that's not finding their head of accounting. the people that need to be hunted. AI is not gonna replace that. And what we're seeing right now is that you've got candidates.

[00:47:00] That are plugged into ai. There's three main softwares for it. They plug their resume or their LinkedIn into it, and it goes across hundreds of different of job boards. And it just auto applies to all of them. And it slightly tweaks. And then organizations are combating this by using their own ai. So there's like another three organizations for vetting, and so they're going through thousands of resumes, the AI and trying to figure.

So now you've got ai, talking to ai that's doing a people job. So long-winded. Does it make recruiting's jobs easier, more efficient, more effective, better vetting? 100%. Are recruiters going anywhere? No. Not if you want the right people in your organization.

Jeffrey Feldberg: That's a great answer. Reminds me of, you've seen it in the movie's, not gonna name the movie. Hey, I'll have my people talk to your people. We'll talk to my people. We'll talk to your people and we'll get something set up. It's bs all the way through. But to your point, what I'm hearing you say is, yes, there is a real.

For ai, but let's be smart about this. If it's more of an entry level role, a role that's not going to [00:48:00] determine the fate of the company where we are this day and age of ai, sure that can help save some time and get to the right candidates. Maybe down the road whenever that is, perhaps higher level AI can play more of a role.

But right now I'm hearing you. It depends. It depends on the type of role and your kind of organization and duplication. The bigger takeaway on this is why even experiment with those kinds of things. Take the AI and experiment in other areas. Talent though, that's where it really counts. And if it's not just your run of the mill entry level kind of job that we're talking about here, speak to Ryan and team, especially when it's sales related.

That's been my biggest failure when I look back at my failures to bring in the right salespeople. That's where I don't have a check mark. I never got the Gold Star with that. I had some successes, but more times than not, I didn't. Ryan, perhaps, had you been around back in the day and you and I had talked, it would've been a very different story.

So Deepp Nation. Why not speak to Ryan and team and see how they can help you on the sales side of [00:49:00] things. Ryan, before I ask my last question, when we go into the wrap up mode, this is not wrap up just yet, but it's a question within a question. Is there a question, an important question that you and I have not yet covered?

Or even an insight, a theme or a message that you do wanna get out to Deep Health Nation before we do go into rapid mode?

Best Talent Not Applying

Ryan Hogan: I would've started with talent is your, like the most important thing you could do. Look, internally first here's what I would probably leave folks with.

This is controversial this has gotten me taken down before, but the best hires are not on job boards. The best hires are currently employed and killing it, and they're killing it so good that they're not wasting their time going and applying to your job posting on Indeed or LinkedIn or ZipRecruiter.

The reality is, and the value that recruiters bring is they have access, they have information, access that it's either in their database or they're paying very expensive licenses to go out and actually communicate with those people who are gainfully employed, just [00:50:00] killing it. And that's really the value.

And a great recruiter is the access to talent that they can bring. So, Long-winded, look internally first, and then when you're ready to look into external whether it's us or somebody else it's the way you can find the best talent.

Jeffrey Feldberg: Yeah, it's a great insight. Deep Wealth Nation, who's the best sales candidate that you can hire. It's the one who's not looking for the job. They're happily employed. They're great at what they do. And I know in speaking to so many founders who are friends of mine who are in the Deep Wealth community.

When they're bringing people onto the team. Oftentimes if it's a high level position, more times than not, it's not even out there. It's just networking and speaking to certain people. And so Ryan, I'm hearing you say for those really important roles. Find someone like yourself, your team, where the people that you're gonna be speaking with aren't even in the market.

You're gonna be the ones to find them, show them that hey, the grass might actually be green around the other side. Why don't you take a look and here's the opportunity, as opposed to doing what everyone else does. We get the same results that everyone else gets. [00:51:00] So that's some great advice. 

Back to the Future Advice

Jeffrey Feldberg: And speaking of advice, let's go into wrap up mode.

It's our tradition here in the Deepal podcast is my privilege and honor where I ask the same question to every guest. It's a fun question. Lemme set it up for you. When you think of the movie Back to the Future, you have that magical DeLorean car. It will take you to any point in time. So Ryan, the fun part is it's tomorrow morning.

You look outside your window. Not only is the DeLorean car curbside, the door is open and it's waiting for you to hop on in which you do, you're now gonna go to any point in your life. Perhaps it's Ryan. As a young child, a teenager, whatever point in time it would be. What would you tell your younger self in terms of life lessons or life wisdom or, Hey Ryan, do this, but don't do that.

What would it sound like?

Ryan Hogan: For me it's, really about, by the way, I love Back to the Future. It's my favorite movie ever. And for me it's just reinforcing not to give up, the whole idea of knowing the path Things changed so much. There's this whole thing of like, oh, if I could, not me personally, but people are like, gosh, if I could have just went back and started [00:52:00] Microsoft before Bill Gates, or if I could have just done this I hear people talk about like, if I could have just started Amazon, there were thousands of Amazons and there's only one Amazon today.

The whole.com era. the thing is, is that, some people have the right strategy, they've got the right people, they've got the right timing, and they're just executing. And so being able to recreate someone's success is very hard. So I think about, for me it's number one, it's probably getting started a little sooner.

Like I was always experimenting or exploring, but I wasn't really taking entrepreneurship seriously. And I think if I would've started earlier. And had those painful lessons learned a little bit earlier, I would be in a different place. And then two, just a reminder that you're gonna fail.

And like the only difference between success and failure is, the resilience and keep moving forward. And it's the journey. It's not about a billion bucks or the jet or this or that. It's about having fun on the journey and leaving a legacy.

Jeffrey Feldberg: Absolutely love that. Never give up. Don't give up. Have fun along the way. Enjoy the journey. Some of the most popular themes here [00:53:00] on the podcast, and Ryan, let me ask you this. 

Where to Connect

Jeffrey Feldberg: Someone in Deep PO Nation, they want to speak to founder of the founder. They have a question may. Be even as Talent Harbor. Hey Ryan, here's what we're doing.

How can you and the Talent Harbor team help us? Where's the best place online to reach you?

Ryan Hogan: Yeah, best place find me on LinkedIn. I'm always in there. I'm always posting sometimes getting into trouble posting, but find me on LinkedIn. It's just Ryan Hogan. It's got this weird mustache. It says we run on eos and I think it's forward slash Ryan E. Hogan, if you're looking for the direct site.

But I'm always on there and, I just love. Talking to folks and hearing about their journeys and brainstorming. So doesn't have to be talent related, doesn't have to be talent harbor. Reach out and let's just have a great conversation.

Jeffrey Feldberg: Nation great news for you. It doesn't get any easier. It's a point and click. Go to the show notes. It's all there for you. And Ryan, that said, congratulations, it's official. This is a wrap as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. Thank you so much.

Ryan Hogan: Thanks for having me, Jeffrey.

Final Subscribe Message

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. 

What [00:54:00] did you think? 

So with all that said and as we wrap it up, I have another question for you.

Actually, it's more of a personal favor. 

Did you find this episode helpful? 

Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? 

And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

Are you ready for it? 

The dramatic pause. I'll just wait a moment. Drumroll, please. Subscribe. Please subscribe to the Deep Wealth podcast on your favorite podcast channel. When you subscribe to the Deep Wealth Podcast, you're saving yourself time. Every episode automatically comes to you, and I want you to know that we meticulously craft Every one of our episodes to have impactful strategies, stories, expert insights that are designed to help you grow your profits, increase the value of your business, and yes, even optimize your post exit life and your life right now, whatever you want that to look like.

And every time you subscribe and a fellow entrepreneur subscribe, it's a testament to how together, Yes, we [00:55:00] are. We are changing the social fabric of society. One business owner at a time, one liquidity event at a time. So don't let the momentum stop here. Subscribe now on your favorite podcast channel.

You'll never miss an episode. You'll be the first to hear from the top industry leaders, the innovators, the disruptors that are really changing and shaping the business world, and maybe you're commuting, maybe you're at the gym, maybe you're taking a well deserved break that we spoke all about on this episode.

The Deep Wealth Podcast, it's your reliable source for the next big idea that could literally revolutionize your business. So once again, please hit that subscribe button, stay connected, inspired, and ahead of the curve. And again, your next big breakthrough moment, it might just be one episode away. Maybe it was even this episode.

So all that said. Thank you so much for listening. And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's continue this journey together. And from the bottom of my heart, thank you so much for listening to this episode.

And as we love to say here at Deep Wealth, may you continue to [00:56:00] thrive and prosper while you remain healthy and safe. 

Thank you so much. 

God bless.