It’s Lonely at the Top: The Real Life of C-Suite Executives With Robert Gilbreath

Robert Gilbreath

Robert Gilbreath is a strategic advisor and the previous Vice President and General Manager of ShipStation, a web-based order management and shipping software designed to increase efficiency for e-commerce companies. In his role, he managed a nine-figure P&L statement and an eight-figure marketing budget, led a team of 175 employees, and directed shared resources. Robert’s background as an entrepreneur and strategic advisor includes SaaS advising, brand building, business development, user experience, marketing, and recruiting.

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Here’s a glimpse of what you’ll learn: 

  • Robert Gilbreath shares how he was introduced to the e-commerce industry — and how his past roles led to his current endeavors
  • Why the role of a CEO is lonely
  • Signs and symptoms of stress — and practical ways to manage your stress levels
  • How to make decisions when you’re experiencing burnout
  • The value of staying connected through peer groups — and the benefits of face-to-face interaction
  • What’s on the horizon for virtual meetings?
  • Robert shares why he encourages executives to initiate fun in the workplace 
  • The importance of identifying your why

In this episode…

CEOs are often isolated from others. Even when standing at the center of your own company, it can feel like you’re floating on an island by yourself without anyone guiding you. Being without support for too long can hinder your productivity and cause burnout. How can you stay connected and manage stress in your personal and professional life?

You must maintain a level of professionalism when leading an organization — but that doesn’t mean you can’t make it fun. Robert Gilbreath, an experienced CEO, understands the pressure C-suite executives face in their roles. When feeling lonely in his position, he identifies practical ways to alleviate stress. Whether you feel most supported talking with a psychologist, joining a peer group, or incorporating fun activities into your work environment, it’s critical to your health and the company’s well-being to take care of yourself first.

In this episode of the Up Arrow Podcast, William Harris welcomes Robert Gilbreath, a strategic advisor and the previous Vice President and General Manager of ShipStation, to discuss the reality of being a CEO. Robert shares practical tips for managing stress levels, the value of staying connected to your peers, and his philosophy on incorporating fun in the workplace.

Resources Mentioned in this episode

Sponsor for this episode...

This episode is brought to you by Elumynt. Eluymnt is a performance driven e-commerce marketing agency focused on finding the best opportunities for you to grow and scale your business.

Our paid search, social, and programmatic services have proven to increase traffic and ROAS, allowing you to make more money efficiently.

To learn more, visit www.elumynt.com

Episode Transcript

Intro 0:03

Welcome to the Up Arrow Podcast with William Harris, featuring top business leaders sharing strategies and resources to get to the next level. Now, let's get started with the show.

William Harris 0:15

Hey, everybody, it's William Harris here. I'm the founder and CEO of Elumynt. And I'm the host of this podcast where I will be featuring experts in the DTC industry, sharing strategies on how to scale your business and achieve your goals. Today on the show, I would like to introduce to you Robert Gilbreath. Here he was the GM of ShipStation and was originally the CMO. He's been in e-ccommerce SaaS for over a decade. And before that he was on the other side of the tradeshow aisle. Robert, I'm excited to have you here today.

Robert Gilbreath 0:44

Thanks for having me. I'm really excited as well.

William Harris 0:47

Cool. We're gonna dig into some fun questions here. There's some fun, there's some seriousness. But before we do that, I do want to at least announce our sponsorship here. This episode is brought to you by Elumynt. Elumynt is a performance driven e-commerce marketing agency, we focus on finding the best opportunities for you to grow and scale your business. We've actually helped over 13 customers now get acquired the largest sold for 800 million sold one to GoDaddy, we focus on optimizing your ads around EBITA or on profit. And I think that's a really interesting way to approach growth, something that we're excited about, about how we do things a little bit differently there. But now getting into the good stuff. Robert, give me a little bit of the backstory here. You you came into this, you were the CMO of ShipStation. GM most recently shipped Jason went through being publicly traded went back to private. There's a lot of fun and injury stuff there. How did you get to where you are?

Robert Gilbreath 1:39

Tell me about this? Yeah, well, you said it earlier the trade show I'll it's something that I share with people and they think I'm trying to do some metaphor for something else, but it's very literal. I was an early adopter of of online marketing and selling online. Really kind of thanks to my dad he had his first eBay store was in 96 or 97. And I was sort of his gofer helper box guy picking parts, it was auto parts. And so that got my spirit got my you know, what, what did my whistle if you will into selling online, and it was amazing to see what we could do. You know, if I tweaked a title, or if we offered international shipping, and I just got I got the bug, right. I didn't know I was learning SEO or I was learning copywriting by doing that I was still in college at the time about to finish. And that just sort of implanted this love of doing business online for me. And, you know, over time, I didn't go into marketing or online retail right out of college I had used since the financial service industries. And but then I had an opportunity to join a retailer. And it's really funny, I actually got hired originally the interview with Bohr to run their private label credit card, it was a brick and mortar retailer, a regional retailer here in Texas in the surrounding states. And that was the original job, my financial service background like set me up well, for that. My boss really smart, really smart lady. They also had an opening for a webmaster, right, the term these companies used to have, and she saw on my resume that I had some of this experience, it was like, Hey, how would you like both jobs? And a little bit of the bartering there was that people asked me did you get two salaries like of course not. But we talked about what it meant to be a webmaster there. And they already had a fairly robust internal website between the headquarters and the stores, they didn't have anything beyond like a three page brochure site for the actual public facing side of the business. And so through interviewing, and later of joining the team, I got to build my first e-commerce site, I'd say build, it's very, very archaic. I use outside web developers who had also done some cool things for our marketing team. And like the corporate in store marketing functions. And these guys, we built this very archaic, it was one product line, it was one product line originally, because that manufacturer would drop ship for us. And it was a manufacturer that had hundreds of SKUs. But we couldn't carry all 100 SKUs. We couldn't give them that much shelf space, brick and mortar retail. So they loved it right. And so super archaic. But then I'm like next level of being into this, like I have to keep doing this. And that, that turned into what became my online retail career where I was, I was either early on in marketing and merchandising and online retailers, or getting hired by larger retail who was closer to going through replac forming. And I another thing I joke about that, again, is somewhat very literal, as I come from a time before SAS. So you know, that thing we built at that original retailer that was all, like self hosted very archaic. There was some agents and manual processes that had to happen to actually complete the request for the dropship. So I have this background where I was forced to build all these tools for myself, you know, by myself or with a team. And that that continued for a while. And then I made this transition to a much larger retailer who had built all their own things in the beginning, but those things just weren't scaling It just didn't make sense for them to have, you know, a multimillion dollar online business running on a server in a closet in Austin, Texas. Does it make sense, right. And so when I talked about the trade show piece, where I'm being literal about that is like, it used to be internet retailer magazine was the trade, the trade rag that we all geeked out over. And they launched and I want to say this was 2004 2005, the first internet retailer Conference and Expo, and it was in the basement of a hotel in Chicago, I always joke because eBay was there every it was a tabletop show, right. So it's all three by eight tables with with these, you know, pretty archaic backdrops. And I went to every IRC for over 10 years. And there was a year where the year before I went as the retailer, and literally the next year, I was setting up a 10 by 10 booth in the early days of ShipStation. And so you know, and I'll just to fast forward, I just went to Las Vegas for Shop Talk, maybe a month or so ago. And there were people there in their own booth, there were at that first show, there was one custom web dev guy who's still around. And so like, for me, I've been across this whole, this whole piece. And it's it's a it's an industry that I I love, the people are great, we're all trying to do really good things. And if it's at the core of where I am today, it's like, even though I'm on the other side of trade show, while I'm getting a chance to help all these, these former versions of myself, if you will, right, to give them and help them. You know, I love that,

William Harris 6:37

you know, being able to help people out in, you know, the path that they're on now. And I just even love the idea of the history there with IRC. IRC happens to be one of my favorite trade shows as well. And I thought I was pretty early at IRC, but you've got me beat them by a little bit. But I can remember, when I transitioned website at the time, I want to say we had about 70,000 skews, and we were transitioning from Magento this would have been maybe 2014 to those 15 transition from agenda over to Shopify Plus. And at the time, Shopify Plus Shopify didn't even have a 10 by 10 booth at IRC E. That's how early even getting into Shopify Plus was. And I remember people saying it's like, You're nuts. Why would you transition a Shopify? That's for little websites, it's not for you know, big websites. And you know, fast forward though, a couple years later, I ended up speaking at IRC e there, which was a really fun and I try to think we've got Tommy Walker was there then eventually shot five plus had really nice, you know, set up there Tommy Walker was the editor in chief there went out to dinner with him, you know, in heard him wrap it in the nice, real fast, rapid everything, just like fun times that IRC. So

Robert Gilbreath 7:50

definitely, you know that that show has, you know, has changed over the years. But still, it's, I think the same was what you're saying it's got a warm place in my heart. And I'm looking forward to going again this year, I think I've missed out to go back and see I think I've missed, they went to San Diego for two years. Didn't do Chicago, and I didn't go to those not because I have anything against San Diego, I was in a different industry, I was in between a boomerang when it comes to the whole ShipStation world. I missed those. And maybe I missed one other in Chicago. So I don't know what year they're on now. But you know, it's a, it's almost the kind of thing like, they can keep morphing it and making it somewhat different. But it sort of has to be, has to be it's that it's that summer, it's that summer event in my mind that we all get the meat out that I agree.

William Harris 8:39

You know, there was a lot of transition back and forth, like you said, and you ended up at ShipStation, cmo there and they went public, correct me if I'm wrong when public eventually took that back private. And that's when you came back on as the GM. It you know, through all of this, you've done a lot of significant leadership just at the C suite level and other places here too. And one of the things you and I have talked about is how hard it is to be in the C suite to be the CEO cmo something along those lines. And there was a tick tock I remember seeing Elon Musk said something to the effect of every one of the worst if you're the CEO, it's literally your job for every one of the worst problems to bubble up to you. If it gets solved before it gets to you. That's a good thing. But the ones that can't get solved or or need to get to you it's you know, that is your job is to solve the absolute worst problems. And that's that's true how it can feel sometimes being the CEO of any kind of a company. Tell me more about it. Like why have you said that? It was the hardest job in the world?

Robert Gilbreath 9:42

Yeah, you know, it's I guess it's easy for me to say that I've been you know, I've been in the room or these things happen for years. And I have to say I think I've been lucky even before I moved across into into the south side of things where I've been at companies and with groups of staff that I was able to, you know, be a person initially, you know, when I wasn't a sea level person, but be a person that that group could come to. Right. And I could be a confidant with them if you trusted. And then I just I became the person that was known that like, so since you're talking about that the rest of the team is not knocking out or Yes, it is a sea level thing, but the sea level person is too busy. It's not going to he's one off projects. All right, I have typically taken on that role. Right? It's a little bit of Put me in coach is the way that I've been lucky to be to places and even early days of ShipStation, very small team, I was number 10 or 11. There. Yeah, we were bootstrapped. When I got there, really scrappy, the marketing team was one person, it was a writer, wonderful content person. She's very early adopter of social media as a means of getting community out there like that, that clicked really quick. Also, to think that the culture of station and the way that we function together as the staff, I joke, like people hear this, they think it was bad that a lot of stuff there was sort of by committee of staff people, right. And so, you know, a lot of those were very heated debates, and, you know, some yelling and some hugging and crying and all those things. But like, that led to, it almost didn't Yeah, it didn't matter really matter who see what in the room, it doesn't matter. It was we like to say we do. And so, you know, part of part of the difficulty with the C step was, you know, it's not just the problems that go there. It's also sort of a lack of who do you talk about these things with, so like, you know, a CEO shouldn't be venting overtly, to the whole company about their own stress, or the problems they're having, like, they have to be able to keep a brave face, what I'm finding now, and I think you're alluded to this, I've recently left, the whole octane, ShipStation family and sort of refining my way and doing some consulting and taking on gigs, partly because the more sort of SaaS providers and e-comm, I can help the more merchants I can help, right. And what I'm finding is, you know, used to hear like the CEOs, the loneliest job, like we're at a whole new level of that. Now, it part of it, I think I'm sort of framing this. And so you can, we could debate this a little bit, a lot of the CEOs that have gone through COVID, the whole COVID times, and what that's meant to their business good and bad. And what it's meant to hiring remote and culture is being changed at companies. I'm finding a lot of CEOs that when I have these sort of confident discussions with them, they're sort of at the end of their rope. Right. And they're sort of like, you know, if you, if you're like me, like if I have a bunch of projects, and I'm like running, going, going, going going. And then what's what's my I know that I'm done, sometimes you sort of just crash, right. And what I'm what I'm hearing and some of my, my consultative calls is that these folks are to kind of feel like they're crashing. And if they don't, if they don't have the right dynamic with the rest of their C suite, which I think I'm lucky, like I said, I feel like I've had a good dynamic in the past. They kept us sane together, right. And if one person was feeling down, it would sort of be this, this mutual pickup could happen. And so I'm running into that now. So it ends up being a little bit different than just, you know, team members think that, Oh, you're the you're the boss, that's the place to be they don't understand what you know, what that limit, there's a limit when you have that over your shoulder.

William Harris 13:23

I and I can relate to that. There's a drawing that I've drawn before, in my own personal feelings with this sometimes where it's, it's almost like this, like circle of people holding hands. And then there's you in the center of the circle as if, as if to say center of attention, right, potentially, where it's like, hey, the eyes are focused there. And, and it's, the reality is that it's, there's nobody holding your hand, you know, you're you're the center of attention. You're you're in this position, but there's nobody that's, you know, in your corner, sometimes it can feel that way. And so, how this a lot of people who are listening to this podcast are likely the owners, CEOs, founders of stores, SaaS companies, what are some ways that you practically help CEOs deal with this? Or what it is some things that you know, we can do if we're starting to feel that well, what are the some of the signs and symptoms first of all, and then how do we practically deal with that?

Robert Gilbreath 14:18

Yeah, I mean, everybody handled stress differently. So you know, if, if we can go that's maybe a whole nother podcast to talk about, like, you know, people's bodies react and our mentality reacts differently to different different for a

while sometimes people do self care, as part of as part of how they handle handle such things, it's amazing. Oh, what was that? I remember what the question was, humor is good. Humor can be a really good way to alleviate some of the stress.

William Harris 14:55

Yeah. We're talking for those who are just listening. I just put my toenails on video. So, signs and symptoms, though of some of that stress that you're feeling as a CEO? And how do you practically deal with that? Yeah, like you said, we can't necessarily talk to the whole team, but there is there is a push to try to bring team members in there and be vulnerable as a CEO. But there's a limit to that as well.

Robert Gilbreath 15:18

Once I know, you know, and we've all we've all been through different coaching sessions and stuff, and I'd say for me personally, having now in my, in my more mature age, like I've been through, so many of these, the ones that I've been through that have the most impact are the ones where there is a group that's being vulnerable, or together actually just, I did a session recently with one of my clients, where the CEO and and their see staff all in the same room, and it was a little bit of mediation, and ended up like some of the words they were using, or, you know, they were, they were, they felt like they were misaligned. But it's like they were using different words, right, and they were all running off, they're probably the right goals, but it's almost like they didn't, they didn't do the kumbaya in the beginning to stack hands, they just went off. And so walk them through that process. I mean, there's got to be we we as leaders, you know, we, we want our we want our, our teams to have work life balance, and we want our teams should be stress free. And we have to, you know, give that to ourselves as well. Right. And it's, it's, it's different for different people, you and I have had conversations in the past about this, like, I have to get up fairly early and go work out. And I do it, and I'm back home before anyone in my home is awake. And so like, well, so what you say I say, well, because then I don't feel only any guilt that I took anything away from my morning time with my children and my wife, right? If I did it, while the time that they're going to school, I would miss them waking up, I would miss you know, a little bit of coffee breakfast time with them. And so for me, if I started my day like that, I feel I'm already starting it, like I'm somewhat fulfilled, I did something for myself, that feels awesome and working out great. And, but then I also can still come home and be a parent and do those things. Right. You know, I also my other thing is just taking walks, whether it's by yourself or with someone else. And, you know, I, I, ex co worker, one of the startups I was at sort of in between my boomerang period, Gary, we, he had this thing that he called a walk and talk, you know, and it's like it all it really was was a one on one, but you're out talking, right? And you're out in nature. And this is not like going hiking down a trail. Funny, funny, not funny is that startup, that startup was across the street from a really old cemetery here in Austin. And the best loop around the neighborhood was you would end up looping through the cemetery. So it's like kind of weird, right? That you're in this cemetery. But, you know, every once in awhile, that would actually lead to some other interesting conversations, you know, or you might go look at a few tombstones and look at names or something. So, you know, it's, it's To each their own. You know, I think also like, back to like, the lonely, the lonely CEO, or the hard part, you know, back to that, like, you can't, you can't go home and complain to your partner about your job, like it's not healthy. And we've all done it some degrees, but like, yeah, it's not healthy. Like, you know, even if your significant other is also a CEO of a company, that's probably not the right person to do it. So I do personally have always had some version of a coach, psychologist, someone that I can talk to you. For me personally, if if they don't push back on what you're saying, that's not the right coach or or helper. If it's someone who's just there to coddle you, that's not helpful either. And so, you know, be able to talk to someone who is impartial, but is trying to help you be better feel better do better. I think is, is also there's also been a finding with my some of these conversations happening with CEOs right now. Frankly, they're not open to go to like a psychologist, but they're very open to talk to a coach. Right. And that's a whole other discussion, too. Like, there's still a little bit of stigma there. But you know,

William Harris 18:55

there shouldn't be though, you know, I know like what you're talking about, there's both. So I have a mentor, that I really appreciate talking to, and he is the type of person who will absolutely call out, you know, any BS that I've got going on. And I appreciate that. And I also go to see a psychologist not as often as I maybe should, but I do and, you know, for different reasons, one of those, they are experts in the way the brain thinks. And sometimes there are just errors in in the brain. And I do like to think about it like a computer where it's a you can get into these negative feedback loops that feel impossible to get yourself back out. And you know that it's wrong, you know that you're thinking incorrectly but you can't figure out how to get that brain back on the right track. And so I do appreciate going to see a psychologist and I remember actually, my psychologist asking me it was like, Well, why don't you talk to your wife about these problems. And I remember just saying this is like I actually I used to but the reality is like, it's not it's not for her to necessarily have to carry some of that weight because I'm not necessarily looking to talk to about the problem as much as it is. How do I get my brain back on the right eight track of thinking. And so that's something that I feel like, you know, sure I can tell her about the problem that solves nothing, though. What I really need is like, Get me off this, you know, Crazy Cycle?

Robert Gilbreath 20:11

Yeah, no, I'm with you there and I got my current coach, mentor, psychologist is an example of like, there's no BS there, you know, resets, how I'm thinking about things, you know, pushes back enough, and doesn't necessarily tell me the answer, which my personal experience like coming home and telling my wife that I had this issue. She's a problem solver and a planner by trade. So she's like, go hear it, and hurt or like, instinct, our professional instinct is to tell me how to fix it. But that she doesn't have all the context. I'm just venting. So you know, this could turn into like a relationship thing. It happens the other way you come home, and you know, they've had a rough day or something's going on. It's in that case, it's about listening. At some point, there's other stuff that couples and people should be talking to each other about that aren't those kind of like, outside of the home problems? Right? Yeah.

William Harris 21:07

And is the right time, the right things that need to be brought up as well. But I agree that, you know, there's just some other things that are good to talk to professionals that certain things a mentor who's been down that specific road and has shoes, that you can, you know, walked in your shoes a little bit, or a psychologist who understands the way the brain is thinking in the loops that it can get triggered into. And, you know, they have those nice little tricks to it, I can remember there was one time where I was I was just really feeling kind of frustrated about a few things and, and there wasn't a good reason to I could logically look at it and say, you know, we're doing better. And it's like I pulled, pulled back and looked at, you know, year over year over a year. And it's like, we're still up really good. And I don't remember what the exact situation was. But let's see, they were up 200%. But I had planned on being up 300%. So you know, only being up 20% is a disappointment, right? We have these big goals sometimes as entrepreneurs. And so yeah, being disappointed about it is a silly thing to be disappointed about. I don't remember the exact situation. But I can remember one of the things of feeling like, how do you feel like you're winning again, and one of the simple ways to feel like you're winning again, in a situation like that, that I had heard, actually, psychologist recommended was from a book called 12 rules for life by Jordan Peterson, make your bed. When you get up in the morning, make your bed. It's a really small thing that you can do that just like you make your bed and you're like why I did that I successfully accomplish this. And sometimes it is just those little things. It's like, well, have you stopped working out? Okay, well go workout and you'll just trust it off your list that you've worked out. You might not necessarily have hit the weight goal that you want it or whatever, but you like, Hey, I made my bed. I worked out and so I have this. I have this planner where it's like I even have my, you know, my handwritten stuff. I love Asana. Sometimes I'll take things in this handwritten stuff. And it's got little checkboxes for like Monday, Tuesday, Wednesday. Did you do this thing? Yeah.

Robert Gilbreath 22:49

Yeah, yeah. A version of that. I'll go off on a little tangent. But I think it's still it's still relevant. Like you, I believe that your brain can only fire so many decisions in a day. Right? At some point, it either gets lazy or it doesn't want to do it anymore. So far that also, it's a little bit of Paquette procrastination determined, but it's like, make a list use. There's a book by one of the founders of Keller Williams, real estate, he actually lives here in Austin. It's called the one thing and it talks about basically, like, what's the thing you're working on, and depending on how like, like any book, it can be, you know, the one the one big project, it could be setting up these frameworks. I don't remember if it was in there, or another book that was talking about like decision, procrastination kind of thing. But it was using sort of the situation of, let's say, you get home from work, you know, it's date night, with your wife, or your significant other or whatever. And but you haven't really planned out where you're gonna go, okay? Now, one thing you know, that you're doing is that you're not going to go out in your own home, right? So the checkbook version errs, get in the car, and at least pick left or right out of your neighborhood. And so, so many times, like you, you could be fighting there, but you could also be in the car and head somewhere. Right? And so yeah, it's a similar thing to make your bed like, accomplish something. Right? And then the next thing will come. The next checkbox gets to be checked in and we all know how good that how good that feels.

William Harris 24:26

Well, there's two things you said that I want to touch on one is about the so many decisions and then the other one is about you know, let's say date night. I want to come back to that. So, so many decisions in a day, and I think that that's why Steve Jobs had his you know, his uniform if you would, or you didn't have to think about it one of my favorite inventors Dean Kaman invented the Segway scooter. That's what he's known for. But before that, he invented the insulin pump. Serial inventor had his own island actually got a fake bill of independence signed and everything and had an phibian really fun guy but he had his it was a you know, like a Canadian tuxedo basically, that he wore and it's like That was his thing he said that was so he doesn't have to think about it. And I've reached that point at times in my career as well, where, you know, I've made so many decisions I, I'm burnt out. And I will say that I think that that is a sign of burnout. And if you do get to the point where you feel like you can't make any more decisions, you really do need to really consider whether or not you're getting to a burn up stage, because I felt that before. And it's it's a very frustrating feeling where you really just feel like you're like, I don't know, I can't make another decision. I don't want to make another decision. And one of the ways that I at least helped myself through some of that, too, is I try not to make decisions that just don't matter anymore. And an example of that is sometimes I like to go to a restaurant, and I don't even want to look at the menu. I want you as the waiter or waitress, what do you recommend? What's your favorite thing? And what's the most great, sounds good, bring that out to me. I love exploring new things. And it's just I don't have to now you know, mull over this menu and figure out great, bring me that sounds great.

Robert Gilbreath 25:53

You're taking it to a new level. I feel like I'm adventurous. But I don't think I've done that ever been and now I need to try it. That's a good challenge. Yeah, challenge for me to.

William Harris 26:02

And then coming back to the date night though, the thing that I like about that is it reminds me of Eos traction, Gino Wickman. And they talk a lot about the the your, the rocks, I don't know if you're familiar with this metaphor, but it's the idea of like there's a, a vase, right, and you can put rocks in it. And you can put pebbles and sand and water, if you put it in the wrong order. If you put the sand into the pebbles in the rocks, there's not enough room for a towel fit in here. But if you put the rocks in, then the pebbles in the sand in the water it all fits in it's the same amount of content in it is that idea of what are the things that are most important to you. And these need to be values of the most important for the business, but also to you personally. What are the things that you value? And what are those rocks in date night absolutely should be up there. If it's not your your marriage isn't gonna last very long. And so you got to figure out, Okay, if that's if that's a rock, how do you make sure that you start scheduling that and planning that ahead of time and making sure that that's important. And I think that that does help alleviate a lot of the other frustrations that we can feel because there is a point where you say, Great, I had a bad day at work, that's fine, but I'm still doing good here. But if you say I had a bad day at work, and well, I haven't done a date night in a couple of months. And so I'm failing at that too. And you know, and I didn't put the girls to bed last night. So I'm failing at that. And that's where that that cycle loop can start catching up to you really quickly if you haven't finalized those things.

Robert Gilbreath 27:16

Yeah, and I said to me, I'd translate that currently into some of the work that I'm doing. And so like, you start getting really, almost you lose your connections. Yeah, and like that, that word being connected means all kinds of things. Like if it's the CEO that feels like they're making too much time making unimportant decisions, but if they're starting to feel not connected, right? If they, if they're, if they're frustrated, at work, and they're frustrated, then they come home, and they take out that frustration on the family, whatever, then they lose that connection as well. And so there's a piece of, you know, if you look at my LinkedIn profile, and I've done this for years, my bio line is very blatant of who and what I am, I am a, I'm a husband, first, I'm a father second. And then I have some of my other you know, marketing and staff or whatever kinds of things. I think it's important for folks, I think back to we talked about earlier, like this, post COVID CEOs feeling kind of burnt out kind of wondering what to do, you know, the some of the rhythms and the patterns that we might have used as professionals before COVID. They change like in what you guys do, like, some of the algorithms in the math around doing online advertising, it just, it's different. So you know, that some of the things we used to do, don't continue to work, but it's got to figure out how to stay stay connected to others stay connected to like, the your why the Simon SIAC kind of the why and what you're doing. And then I get challenge for CEOs today is like if they're feeling their employees are feeling, you know, potentially burnt out and disconnected or whatever. So it's like, the CEO has to really feel connected back to the mission of the company and what they're trying to accomplish. You know, whether or not it's the same line on the chart as before, COVID are right after COVID or whatever they need to be feel confident about that themselves. That's the only way they're going to make their teams feel confident. Right. I do though, the thing about connections that I've always pushed and I'm sort of, I have an uncle here in Austin, who is part of one of the oldest in-person Still continuously going networking group, and this is all fashion network. And they meet at a sec, a separate club place for lunch once a week. He is the only lawyer in the group. There's it's very old school, there's a plumber, there's a guy who owns a pest control company, you name it, they're all there. I could never join with him because there's already a marker on there, which is funny, because it's an old direct marketing guy, but he's the marketer, you know. So my modern version of that is, you know, obviously, we have LinkedIn and we have other kinds of meetups and whatnot. And it does for me, it does blow my mind the number of C level folks and not so much with the marketers and the sales guys gonna think we're just naturally outgoing and we want to do those things. But it boggles my mind the amount of CEOs that don't have their own outside of the office network that's not you know, the home life right Do you see people to get into EO and these different groups, and you can see for a lot of time, that is one of their ways to connect, right? And they'll use those other connections as an outlet to be able to talk about these things and get advice and whatnot. So I'm still surprised. To me, though, the lack of that going on. Yeah,

William Harris 30:18

that's a good shout out for EO in other organizations like that as well. Shane Erickson, I'm gonna give a shout out to him, he has bugged me about getting into EO for a few years. Now, I do need to make that happen. I think that's a smart thing. It's one of those things where, you know, I need to prioritize it. But there's something about where, you know, getting together with a group of people that are in similar situations, and you can feel like, well, they're not in the exact situation, maybe maybe, like you said, it's like, well, they're not a marketer, like I am, or they're not a, you know, or they don't run an agency, they run these others. But the reality is, it comes down to the same core concept. It's like, we either have a people problem, or you have a, you know, profit problem, or you have a production problem. That's about the three main ones I think I've heard. And so it's like, they've been through those same situations. And so there's, you know, ways that they can at least commiserate or relate to what's going on with, you know, what you're going through and how that's affecting your job and your psychosocial and your family and all those things.

Robert Gilbreath 31:14

Yeah, yeah, there's a yeah, there's, there's something that you said that interact with folks who have maybe seen similar patterns or been through similar patterns that can pattern match, if you will, to what, what you and or your businesses is going through, that's what's been fun about what I'm doing right now, I'd be able to talk talk to, like examples, or like partner companies of ShipStation. And some of these, I was the person who developed the partnership to begin with, and so being able to chat with these folks, you know, having having sort of some insider information on what they're going through, is been interesting. It's, for me, it's been, it's been an interesting way, my own connection, right, like for me to connect with these folks. And I know I'm coming from a place of trying to help and trying to move them through some of these issues that they're experiencing.

William Harris 32:03

Yeah, so we're gonna give people you know, actionable advice here, it would be, you know, get involved in some type of a, a, you know, peer group, basically, right, like, not not just online, it's fine. You can meet online, but you need to get together in real life with a few people that are in some kind of a similar situation to you.

Robert Gilbreath 32:24

Yeah, what up percent? Yeah. And I'm one of my New Year's resolutions. I know, we're doing this virtually Europe, Europe, where you are, and I'm down in Austin. One of my New Year's resolutions is if I, if I see someone, if somebody wants to connect in me, if they're in Austin, we're meeting in person. And that means that we're not meeting for a month, that's fine. I've made one exception, because it's someone who actually lives here, but she's doing sort of around the world long trip, I'll meet with her over zoom, she's not going to be back anytime soon. But other than that, it's been interesting. There's been a few people that are like, taken aback. And they, you know, I joke and say, I'm not asking you to come to the office every day of the week, I'm just asking you to meet me at the coffee shop that's literally halfway between our homes. And, you know, let's, let's get out. So I got that's another that's another piece as well. You know, whether you whether you have an extreme bias to asking employees to come into the office or not, I mean, it just to me, it just makes sense that being out, you know, face to face, handshake, the handshake like that can't be replaced with 100% virtual stuff all the time. Yeah, and even even folks that I know, that are remote, like, they need to get out as well.

William Harris 33:33

I'm gonna get weird here, right, like, from a from a, let's say, a biophysical perspective, I think there's something about like, just being around each other, and like, the sweat that exists or whatever, where it's like, it encourages, like, you know, like, it's almost like your pheromones being around you going out accomplishing it makes me say, I'm gonna go out there and accomplish it to let's say, I want to fight alongside you. Right. And, and I think that there's something that we need, just in being around physically around other people that are doing similar things to

Robert Gilbreath 34:03

me, I get I get energy, energy from it. I mean, that even looks like I mentioned earlier, like, I don't think I would have had the same career development opportunities. Had I been, you know, in the situation where half the meetings are resumed, or, you know, whatever your your virtual meeting platform of choice, the, the impromptu things wouldn't have happened. You know, when when we were in the opposite of all time, the amount of like random meetings that would happen that I would be lucky enough to get pulled into write, those weren't gonna have those don't happen in the same way. You know, some of the tools would they have like instant huddles and stuff. They try to make that happen? But it's tough, right. It's tough and I'm hopeful I think there's still there's some new iteration of all this it's got to happen, right? Where it's, you know, are the tools for the virtual meeting is going to be martyr or they're going to, they're going to use the newest versions of AI to help improve like body language reading and whatnot or We'll see, it's gonna be interesting to see because we know it's not going away, right? No.

William Harris 35:03

And I'll tell you where I think it's gonna go. And here's where I'd like it to go. I actually talked to Justin coffin Berg at rally ventures about this man, maybe back in 2020 20, I think right before everything shut down. But I've really liked VR actually, I've invested in a really cool VR company called allegory up in Toronto, and deepfake. His technology has gotten really far along the way. I don't know if you've seen the codec avatars that Facebook has, but is you it is a video of you, it looks identical to you. And I think one of the scary parts about it and why it's not there yet is one who drives it. And so I think Zuckerberg said something to the effect of, you know, we can't even launch it until we know that there's like a way where it's like iris scanner, and it's like, it's only you that can drive your avatar. And there's also a processing component here, it takes like two weeks to process this, but let's just imagine, you know, you and I wanted to get together in person, but you know, you're in Texas, I'm in Minnesota, and there's all the body language motions and stuff like that are taking place. But if I had my VR headset on, you had yours. We're sitting around a table, and right now it's very avatars, you know, what is the horizon workspaces, which I've done, and it's, it's fun, but it's very, you know, animated, but if it was you, and it was me, and a deep fakes your face onto it, so that way, you know, it's got cameras on the inside. So it's seeing your eye movements and expressions and things like that. And I think that that feels a lot better. I still don't think it's a replacement. But I think it's significantly better than just

Robert Gilbreath 36:30

yeah, you know, what I have not, I have not seen all the all this sort of, they've all been sort of cartoonish. They remind me of like playing Wii back in the day. And like the little bobblehead looking characters and things I've done it a few trade virtual trade shows at the height of COVID. And it was, it was nice to be able to get together and like a booth was a room and those kinds of things. But yeah, there's, there's got to be the next iteration. iteration of that plus into VR, we can play golf and do other games, it's up to it's all there's some fun that could be had imagined doing a team outing where you have the meeting, and then you leave the conference room and you're, you know, you're out playing flag football, or you're doing whatever. Absolutely kind of interesting.

William Harris 37:10

Well, okay, so playing flag football, that reminds me that's a good transition into the third thing that you and I have talked about here. So if we're if we're gonna say like, you know, these three big things for CEOs who are maybe overwhelmed or feeling like they're in, you know, the, the toughest job, the loneliest job, whatever have in the world, one mentorship or psychology or something that's helping you like a business coach, somebody that's helping you along the line of those thinking, too, would be that idea of like making connections, right? And we talked about, like getting involved in peer group. But the third, you said, and there's a phrase you use for this font as approved, right? That's the phrase.

Robert Gilbreath 37:46

Yes, that's it. Yes, it is forever. And always,

William Harris 37:51

yeah, well, okay. And like, take me through this because somebody else that I really liked Sujan Patel, he's always told me what's the fly on that though? What's the font on investment? But like, fun is, why why is that a thing that you have made as a big part of what you do?

Robert Gilbreath 38:06

Look like, life in general. And like, work life is it's, it's stressful enough and hard enough? You know, and we could go down a whole tangent that says, like, if you are a little bit stressed, or having a little bit of angst, you're probably not doing it. Right. Right, you're right, maybe you're not the right choice or whatever. But, you know, we can call it icebreakers. We can call it whatever. And we see it like it's happened. It's happened with Slack. Right? Every company, you know, until they get to like maybe the annual time where they delete all the things. There are some silly fun Slack channels, right? dog lovers, beard, people, whatever, right? My version of that goes back to before set. My version to that is just like, Goofy, Goofy things. One of the close to one of the last, like team meetings I had in our office in person with the majority of the people in the room. I don't know what I was thinking. But I look over at the whiteboard. There's a bunch of whiteboard markers in a container that's like magnet to thing. I picked them all out, I handed out everyone a marker. And I was like, hey, from where you're sitting, trying to throw it into the thing? Well, the mood, you know, we were waiting for the people to show up on the Zoom or something. So I didn't you know, back to my being guilty about stuff. We didn't really burn any corporate time or anything. And people were people were being goofy about it. One person even suggested like, let's do a let's do like a tournament bracket for those. It literally took five minutes. Everyone's laughing. everyone's mood was elevated, the energy was instantly better. Then you kind of like razzing the person on Zoom. I think in that one. We actually yeah, you know, a creative guy was on it. He's based in Pasadena, California. We made him use his pencil cup. And he tried to do it, you know, this guy. Again. He's having a good time. And who knows if he was having a good day or not. So like, I got some of this I attribute back to just like, having been in companies pre all the startup crazy kind of company stuff. And being at some fairly traditional companies that had sort of this model of like They're not really goofing around. That was a one retailer where they did leading up to season because their their suit, their business was super seasonal. They did basically the version of like Office Olympics. And there was captains from different departments and you could draft teams, and the CTO, CTO of that company would go to this weird convenience store here in Austin and also sells flags. In any kind of flag or country, you can think of like cheap nylon flags, he would go every year and buy like six random flags, usually the funniest or weirdest ones he could find. And he assigned each one and we actually raise flags in like, the main double decker office area, playing the Olympics music, you know, and it's just like, hey, this is silly. It has nothing to do with our business. But like you would meet people in different departments. The the games are, like, very weird, like, almost like Vegas vacation kind of games, you know. And so it's just like, it was it was it was good. I mean, it's, it goes back to also just like smiling is good for you. Laughing is good for you. And so, you know, in this case, something like that it was it was organized by the company. So there was no no guilt and no reason why you wouldn't want to take part. Yeah, people that people that around you they know that's that's my little, that's one of my I have too many monitors. But that's one of the ones I've really tried to push.

William Harris 41:18

That's a good one. And I think that there's a lot of research around even increased productivity and people that are enjoying their job. And I've I've witnessed it firsthand, where one of the guys on my team had put something together. And then he had a meeting with me. And on this meeting. We were planning, basically what I was planning out what I wanted to do to my business partner. And there's a story that I'll tell you about in a second with that. But, you know, it was a really fun meeting. And it was he just, he laughed so much and had so much fun. He said, I undid he messaged me right after our meeting, he was like, Hey, by the way, here's a new video of what I just put together. Like, you inspired me so much. I just I lifted my spirits in such a way that like, I was able to just think clearer and do significantly better work. And I think that that's something that we undervalue. Sometimes it can feel like maybe as a CEO, or, you know, if you're just counting, you know, the peanuts or something, then you're you're not focused on how much that can really increase the productivity of the people on your team. Yeah, so So the story though, because this was good, because I told you, I was going to do this. In the last meeting that we had, it was the day that you and I met the last time. There was a speaking of connection, there was a an e-commerce meetup that we were hosting. And it happened to be five minutes from my business partners house. Now, we became business partners, during COVID. I've actually never been to his house. So that's an important part of the story. And I said, All right, well, he can't come to the, to this meetup because of something that was going on with his kids school, but it's five minutes from his house. So after this, I told the team I was like, alright, well, I'm gonna go TP Jeff's house. And so I did, I went over to his house, and tpds house, showed the video to the team. That was not his house. It beat his neighbor's house. So I have a good video of that on tick tock. I'm happy to share with everybody but that actually is more fun.

Robert Gilbreath 43:13

Oh, yeah. Okay, you get kind of got him in trouble, because it's his fault. Right. You were you were trying to get him? Yeah. Well, that's it. Yeah, that's

William Harris 43:23

having fun. A great. Yes. Fun is approved.

Robert Gilbreath 43:28

Yeah, one 100%. Yeah. Yeah. For another for another podcast where you can we can go, we could talk about raising children in the new world? And how do you expose them to fun as approved, you know, in a way that that doesn't get them in trouble, that's not going to, you know, have some other damaging effects. And, you know, that's safe and in a friendly kind of thing. And that's a whole different, that will be a different topic for us to cover Sunday.

William Harris 43:55

It'd be a good topic, though. I think I'd love to dig into that sometime. I will say that, you know, there's a lot of ways if you're looking for other ideas, you know, maybe there's a way that we can start a thread or something of just fun ideas. You could do over zoom meetings or in person, you know, you had mentioned like football. In VR, it was kind of the idea. That reminds me of something I've wanted to do with the team here and I need to pull the trigger on it. But have you ever seen binocular soccer? Have you ever heard of it? There's a video it's in Japan. I don't know if it's a big sport. But I've at least seen this this video where you basically have binoculars on and then you try to play soccer so you can't tell how far you are from the ball at all. One of the funniest videos I've ever seen, and I want to do something like that with our team where we've got a few people on the team that absolutely love soccer. I've never played soccer but you something like that. Just be silly and goofy and have a good time.

Robert Gilbreath 44:46

Yeah, so you said binoculars the correct way or backwards because you can imagine if they're the correct way, the ball is right there. But if they're backwards, that's when it's like how far out is this thing or how close are these people to me now I've got to go after this. There's 1000s of videos It was on YouTube.

William Harris 45:01

What? Yeah, why don't I link to it in the youth in the in the comments here too, or something? But yeah, I think it was, I think it was the correct way. But yeah, the depth perception is all off. So you couldn't tell quite how far you are from the ball.

Robert Gilbreath 45:15

That's amazing. Along the lines

William Harris 45:17

and of having fun. I talk to you about wanting to do this. So I try to have a little bit of fun on the show here as well. So I've put together a silly ad libs script. So you we're going to pretend here's the here's the scene. So this is an interns first day on the job at an e-commerce growth agency. You're gonna play the part of the intern, but for right now, I probably even shouldn't have said that. Right now. I'm just gonna ask you some some answers and you're gonna answer this just like a typical Mad Libs would be and then we're going to act it out here. Okay. Okay, so I want you to give me an animal any animal Aardvark tipo que Hippo? Hippo and a fruit. What's a fruit? Banana. Okay, and let's give an adjective to describe a body part.

Robert Gilbreath 46:10

Here Oh, yeah, yeah, they will not want to take yours Yeah, let's do we'll say say muscular. muscular.

William Harris 46:21

Okay, I need a past tense of a verb so verb doing something past tense.

Robert Gilbreath 46:28

Well, okay.

William Harris 46:31

I need an interjection lets you know like, you know, a holy or something. Some kind of an interjection

Robert Gilbreath 46:39

Oh, no, I gotta figure out something. That's easy. I know. You're gonna stump me.

William Harris 46:43

harder when you're on the spot, right? Like, on the lay?

Robert Gilbreath 46:46

Yeah. How about how about? How about a nice WAMC I know you're gonna get me. Um, do a do a rock on a rock on?

William Harris 47:01

How about an adjective to describe Halloween? That's something that describes Halloween. Scary, but something else

Robert Gilbreath 47:08

scary. Scary. So scary. Scary. Spooky.

William Harris 47:12

Spooky. Alright, let's do spooky. Um, how about okay, we need a body part. Now.

Robert Gilbreath 47:18

We need a body part. foot, foot.

William Harris 47:22

And we need okay, that one's the same one here from above. We need a brand name pick any any brand name.

Robert Gilbreath 47:34

Now to get our foot I would love to give you a shoe say Levi's. Levi's.

William Harris 47:40

We need an adjective to describe a zombie

Robert Gilbreath 47:47

drippy 50.

William Harris 47:49

That's funny, because that's actually like, that's actually like a word that you're supposed to use now according to Gen Z. And then a, I just need a noun and I couldn't think of anything creative for it. But just a noun, any Noun. Person, place thing, watch.

Robert Gilbreath 48:03

A watch.

William Harris 48:07

And then I need a plural noun for a group of people. Idiots winners, pirates. Something like that.

Robert Gilbreath 48:18

Classmates, classmates.

William Harris 48:21

And last one. No, not last one. I think there's a couple more here. I need a problem. What's a problem that somebody might have?

How about about bad breath? Bad breath. Okay. I've got the brand name from above. And I think we're just about done here. I need one more noun, person. Place thing? Absolutely anything. Let's go with a tree. Okay. And let's see. Last one is a number. Any number

Robert Gilbreath 49:03

of set number seven?

William Harris 49:07

Let's pick a bigger number. I mean, let's say let me say pick a number that is bigger than 1000. Okay, it's gonna be 12 134 1200 34. Okay, I'm going to share my screen here. You'll be able to see this. You're going to act out person number two. I'm going to act out person number one. We got to get in character. Okay, remember? You did you are the intern. This is your first day on the job.

Speaker 3 49:37

This is the scene. Are you ready? Okay. Oh, let me make it a little bit big. Absolutely. Go ahead and go a little more. Yeah, there we go. Okay, I'm person to your person to

William Harris 49:49

Hello, welcome to your first day at hippo banana, the muscular growth agency in the world. First things first, we need to get you a have spelled into our HR system.

Robert Gilbreath 50:04

Rock on. That sounds spooky,

William Harris 50:07

huh? Something seems to be wrong with the scanner. I'll have to use my foot instead.

Robert Gilbreath 50:15

So can you say that? Am I? My last job, my last job and never let us use our foot. Okay,

William Harris 50:26

well, now that that's all done we can finally have you log in and start working on some new ads for Levi's. This ad is currently performing the best for them.

Robert Gilbreath 50:34

What do you think of it? Well, at first glance, glance is drippy. It reminds me of the of my great grandmother's watch. That's a

William Harris 50:43

little harsh, don't you think? Okay, fine. Well, what would you suggest for new ad copy, then?

Robert Gilbreath 50:50

What if it said something instead, like, afternoon classmates? If you're looking for the perfect solution for your bad breath, then look no further than Levi's. Levi's tree? And, and hold on. And best of all, it's super easy to do. And it only it only takes 1234 steps. Okay, sorry. Well, sorry.

William Harris 51:25

This is just your first day. I'm sure you'll get better at this. That's our that's our

Robert Gilbreath 51:33

that's cute. That's awesome. Man. Bringing it back home. Yeah, yeah, go ahead, go ahead. Again, this is a perfect example of, you know, fun is approved, it doesn't have to be some kind of super, you know, super serious thought out thing. It could just be a goofy, you know, just a goofy thing where there's, there's no right or wrong answers. And there's no. You know, I feel that I was already having such a great time talking to you, like I do that. It's like, kind of silly, goofy didn't matter? How it turned out. It just, it's another fun moment? Absolutely.

William Harris 52:08

I want to wrap it up, though, with something serious, then, you know, two things, the first thing I'm going to ask you is, if people want to reach out to you, they want to get ahold of you follow you? What's the best place for them to stay in touch with you?

Robert Gilbreath 52:21

Yeah, I mean, just to make it easy, RobertGilbreath.com is my is my website, it'll get you right to my LinkedIn profile. I'm very open on LinkedIn, if I can, if anyone wants to connect, I'm going to say yes. If if we're once we're connected, and if I can be of any help with introductions, and I'm very close, I'm over. I'm overly honest with those if someone asked for an introduction, and I don't think like, if I don't believe I'm the right person to make the introduction, I say so. But if I feel like there's any way I can help, again, one of my other mantras is I'm here to help. And I do believe that like, just doing that way with no expectation, anything in return is the way that we can all be better together. Yeah, just RobertGilbreath.com, we'll take you to my LinkedIn and, and, you know, connect and message me and we can, we can we could talk about what you're up to. And, again, see if there's anything I can do to help.

William Harris 53:11

Yeah, last thing, if there was one more piece of advice that you would give to somebody, you're you know, we've obviously gone through a lot. But if there was one more thing that you would want to say, and it could be about absolutely anything about work about family about life about whatever, what would you want to say?

Robert Gilbreath 53:24

Yeah, I just say like, back to what we talked about connection, just take a deep breath when you're having a tough time and try to try to think back to why you're doing this things, right. And it can be as can be as simple of like, why am I doing this task, right. And just always try to get back to that no matter whether it's a task or a big thing. And then be honest with yourself, if you can't back into the lie, that there's an issue, that probably means you need some kind of help that necessarily mean that you need to see a psychologist or that you need to coach but it might mean that you need to go to your boss and clarify something remind you to go to your other and get some clarification. But you know, try to that connection, like I said, comes in different ways. And when you're feeling, feeling stress or feeling out of place a little bit, try to get back to that y piece. And then you're likely to be able to get right back on track. Thanks. Well,

William Harris 54:13

Robert, I really appreciate you coming out here joining us sharing a lot of really good insights for how to you know deal with the stress and problems of being the CEO. And thank you everybody for coming out and listening in.

Robert Gilbreath 54:26

Thanks. Thanks for having me. We really enjoyed it.

Outro 54:29

Thanks for listening to the Up Arrow Podcast with William Harris. We'll see you again next time and be sure to click Subscribe to get future episodes.

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