Ep #19 | Homeless to Hyper-Growth

Kit Headshot 1.jpg

Kit Hughes is a typical technology entrepreneur. He dropped out of college to start a company (it failed), spent a period of time homeless (by choice), and became an overnight success (slowly).

Eventually, Kit returned to school as a two-time research fellow at the University of Georgia leading experimental technology research projects exploring mobile computing and connected devices. He credits his business smarts to his studies in strategy and innovation at MIT.

In his agency career, Kit has worked with a variety of B2B and B2C brands across multiple touchpoints: AnheuserBusch, BP, Char-Broil, Coca-Cola, Flextronics, GE, NCR, Philips, and Steve Harvey.

He co-founded Look Listen with his collaborator in punk bands, Paul Sternberg. Under Kit’s leadership as CEO, Look Listen was recognized as one of the fastest growing privately held companies in the US by hitting #408 on the Inc 500 in 2015—staying on the list three years in a row—and has been in the top 100 fastest growing companies in Atlanta three years in a row, according to the Atlanta Business Chronicle Pacesetter Awards.



Shantel: Hey, Kit. Welcome to the show.

Kit: Thanks for having me.

Shantel: Yeah. We are excited to learn more about you and your journey. Let's just kick things off and start by telling the listeners a little bit more about you and how you founded Look Listen.


Kit: Yeah, so gosh, it's actually been about 10 years now since I started the company with my co-founder, Paul. We were childhood friends, and we grew up playing in bands together in high school and college, and then I hired him to help me out with my first company I dropped out of college to start. Then after it failed, of course, a few years later I called him back up and said, "Hey, I think that we should make a run at it again, and I want for you to help start it with me." That was on the eve on the financial crisis. I was working at a big company that was Global Enterprise, and I had mortgage and family that I needed to take care of at the time of starting a company, and he didn't have any of those things. I used to call it overhead, but I found out that a spouse and children don't like to be referred to as overhead. I don't think of them that way. It was just a word I had used for so many years. He didn't have any of those things. He was living in a ... Had roommates in New York and Brooklyn. We lived those first several years ... Our founding story was kind of in a way we were kind of getting the band back together and starting the creative collaboration, kick starting that from what we had had earlier in our lives and putting it into a company. Then financial crisis hit as we started the company. It took us several years to get to a place before it felt like anything more than a glorified freelancing operation and I could leave my full-time job to focus on it completely and make it my single focal point.

Shantel: That's great. Well, what instrument did you play in the band?

Kit: Yeah. I played guitar. I never played lead. I played rhythm, and I was the front man. Actually I kind of joked a lot too that in our early days when we would pitch work because ... Sorry, I didn't even say what we actually do as a company. In the first part of our existence, we just self-identified ourselves as a studio. We were designers and developers. We had a real maker culture. We were making apps, sites. We were even doing motion graphics and video. We thought of ourselves as a studio. In those early days, we would even talk to people about how that early collaboration, the creative collaboration that Paul and I had had together, and talked about how I, in the company, played this role of front man and everything, and then Paul would be the guy, he played all these different instruments. It was just really cool. He's tremendously talented. We joked also about behind the scenes of the company too, that he was designing this thing, cutting this video, putting it together, shooting photos, and that kind of stuff. Our creative dynamic continued, which was really, really cool, which is the right way to do a business partner collaboration as I found out later. I'm, looking back on it all, glad that I played guitar and sang for the bands and glad that he did all that he did because then that made our own collaboration stronger.

Shantel: Yeah, absolutely. Did you guys go into the business having very clear roles or very scrappy in the sense of well, I'll try this this month and you'll try this and then we'll see how that shakes out?

Kit: It's a good question. In those early days, kind of as I was alluding to, we would show the clients that we would pitch. We would present ourselves as Kit as this business guy, and he's going to be the person that actually runs the business, manages the money and all that kind of stuff. They could look at me, and I would wear a sports coat, and I would kind of dress up for these meetings. Paul, who's tattooed, would wear flannels and roll up his sleeves and all that kind of stuff. It was really cool because we played these characters almost, but then behind the scenes, when we would actually do the work, I would do a lot of concepting and ideation for initial design. He would also do the same. We would divvy up the work between the two of us. In our operating arena, we had, of course, me as the tax matters partner and me as the person that held these specific responsibilities versus him and his responsibilities. Some of that stuff is really ... I hate to make core analogies but I think that this is probably the best one that I can think of is that like when you're up in the tent, the sort of general tent off the battlefield and you're strategizing and you're making a plan, that's like one frame of mind. Then when you're down in the battlefield, all rules are out the window. It was very much that dynamic of externally we looked like we played these roles, but when we were actually in the work, doing the work back in the office or studio, whatever, we were actually doing a lot of the same stuff. He never touched the money side, which I guess is what was the clear difference between the two of us.

Shantel: Okay, and how has that shifted now? Is Paul still with you and part of the company?

Kit: Yeah, and he would actually laugh if he heard you say is he still with us? We actually had a client very early on ask us what would we do if we died or something to that effect.

Shantel: Geez.


Kit: Yeah. I know. I won't mention who it was because it was actually a pretty well-known group that that question ... It just came from somebody shooting off the cuff, like, "What are you guys going to do if one of you dies?" Something like what happens to our work, which is a really super weird question to be asked. Yes, he's still with us on this planet, but last year I bought him out. We just had a really great conversation last June in which we talked about the direction of the business and the direction I wanted to take it and how I felt like we could work out a deal in which we both still kind of get what we want and in a very way that we're both extremely proud. We probably had the most civil and mutually beneficial partnership buyouts in history because we were told left and right that it could get totally ugly, and it didn't, which was great. It just shows also how non-ego centered our conversations were together and the fact that we were friends and that we were good partners together. He continues to be involved in a limited capacity with us, working on some special strategic projects for us as an agency, and that was part of our agreement. I shifted a year ago into the sole owner role of the company, which has also been an interesting dynamic and one that I didn't have a lot of experience with because I always had business partners leading up to now.

Shantel: Well, I'm glad to hear that went so well. I have also heard that sometimes those equations don't end very well, so glad to hear it. You brought up that point about what if something happens to either of you. I think that as a business owner it's hard sometimes not to get stuck in the weeds of things and to realize you should be working on the business instead of in it, which makes me think you guys have really great ... Well, you are one of the fastest growing companies, so you definitely have wonderful process and systems in place. After a conversation like that, did you guys pow-wow and say, "Shit, what will we do, and how can we make sure the team's set up for success if, God forbid, anything ever happened?"

Kit: I'm glad you just broke the seal on cursing, so I can do that now. Thank you.

Shantel: You're welcome. I don't know if it's allowed with Apple podcasting, but we're still learning, so feel free.

Kit: Let's test the boundaries in this conversation. First off, I would say something I even remind some of our employees of and people on my management team and remind other entrepreneurs is nobody has it figured out. I guess one of the biggest things is that I think that we get in our heads a lot, and we think about how back when I had a job at a certain company, there was this level of stability, or if I could only make my company like that company, it would be all great because they've got it figured out, but the truth is that nobody does. It's a charade. For people that don't admit it, I'm a really very transparent person and have no problems talking about failure. My LinkedIn profile shows that I look at the highlights and the lowlights of different years. I just wanted to put that out there. I know that wasn't answering the question you asked, but we may have won these awards for being a company that's in hyper-growth and broken the Inc. 500 and all of that. I will say that as an entrepreneur and then as you end up building a company around you and should you choose to cross the chasm of entrepreneur to CEO or another C-suite position in which you're going to have day-to-day responsibilities instead of just being a serial entrepreneur and going and starting other companies, should you decide to stay on, you have to move into a different mode, and you have to think about processes and people very differently, and also maybe even to some extent the purpose of the company because you change as you grow. It's never perfect, and nobody has it figured out. Now you can be better at it, and maybe even be more in-tune to where you are at a specific point in your own history or dealing with external circumstances, but there is no perfect company that has it all right. If you get a fellow entrepreneur to really level with you, they will probably say, "Yeah, at that point in time when I achieved that great success, I also had this other thing that was in shambles or counterbalancing it." It's a myth to think that somebody reaches a pinnacle of having all the processes done because you're constantly in flux. I just wasted all my time deviating there away from the question, but I just felt the need to call that out. Yeah, so what question should I really be answering right now?

Shantel: No. I think that there's such a level of vulnerability of being that honest and frank with the team to say, "Hey, I don't have all the answers, but we're going to figure it out, and I'm going to work hard to make it work." That's super honorable. You talked about highs and lows and how you reflect on them and your LinkedIn. Is that something you've been doing forever? Is this a recent practice? I'd love to dive into that because I think that's really interesting.


Kit: Yeah. I rewrote my LinkedIn profile at least five years ago, if not longer. I think it was probably about five years ago, when I looked to actually focus on Look Listen full time versus handling a full-time job at the same time of doing Look Listen on the side. What I was faced with was I think what a lot of people are faced with right now is that a standard linear resume format doesn't accommodate the way professional lives exist anymore. Whether it's like the notion of a side hustle or the fact that people are doing much more in a volunteer capacity so they should get credit, and I use credit with air quotes here, for those types of things. What I did was I just looked at how LinkedIn forced people into this very linear approach to documenting their work history or their professional history or whatever. I was like not only does that not work for me, but I've got a feeling that it doesn't work for a lot of people and it's extremely outdated. I just sat down to figure out how to actually hack the way that LinkedIn presented information, how to actually also do in a really authentic way and how I felt like it needed to be reflected. Like the bullshit of saying I did all these awesome things at this role, the fact that no one would have been disappointed or you ever failed or that you were even disappointed in yourself or the situation or whatever, I just took real issue with that. I felt like I'm so easy to admit my own mistakes and temper, some of my own perceptions. I'm here for me to really live on this earth and to bring some contribution and try to make this world a healthy, happier place, take care of my family, and all those kind of things. I felt like presenting yourself as this mythical creature or statue on a place like LinkedIn, it just wasn't for me. I held a critical eye to it. I also went to art school. In art school, you're perpetually criticizing everything, so call it also a casualty of that kind of training. I specifically saw a problem with how to present my experience working for a global company as well as the experience of starting a company, and then also how far back do I go and showing that I worked at Burger King when I was 16, which is really funny now to hear that I'm vegan, and I was serving burgers as a teenager as my first real job. What I did was I just looked at how LinkedIn presented info and said, "I'm going to write my history into this format and do it in a way that's authentic to me." I went back until I think I was 20. I went that far back and talked about some of the first experiences I had when I first started freelancing and choosing this sort of more of an entrepreneurial life that it took me a while to come back to. I put it in the LinkedIn format and made sure that every year had lowlights that I communicated as well as highlights, and I feel like that was the best format to do. While the year is in progress, I'll put stuff in, kind of like a so far, and then at the end of the year, I'll really go back and look at and try to limit myself anywhere to three to five highlights and three to five lowlights to communicate out. I'll be honest with you, it's been a little bit more difficult recently over the past couple years. I'm by no means, I dare say the F word, famous. I'm by no means that. I'm not saying that, but I'm on more people's radars. I speak at conferences. I get random emails from people. I'm more public than I ever had been in my life. That's a better word, the P word, public. I'm more public. The past couple years have actually been a little more difficult because the question is how much of the lowlights or the nuances of the lowlights do I actually communicate out. Last year I decided to just write one that was tied to the fact that I've essentially given up on trying to change people's perceptions. They're going to think what they think about the information they have, and I need to move on from that. That was a hard lesson for me to learn as I interface with more people, whether it be clients or employees and former employees or strategic partners or people sitting in an audience at some conference or whatever. I just am blanket not going to worry about what people think and that would be a surprise to some people to think that I was ever hung up on that. I can't control what people perceive. Last year, that was a huge thing that I had to get over.

Shantel: I think that that certainly, I imagine, would help ... You sounded super self-aware, and the time that you take to do that and reflect on that and learn and grow, but I'm also curious because it's such a public thing if people have responded to that and been inspired or when you're talking to accounts and maybe they're seeing that, what has the response been from the public?

Kit: Yeah. I have gotten countless emails from people, even some people from LinkedIn, directly about how I built my profile and saying that it was the most unique profile. I got even some pretty heartfelt notes from people saying that they felt like they knew me more than people they had actually hired and work with because of my level of honesty. Also, by the way, I'll say the flip side of this is I get really upset when some people, I'm not saying this happens a lot, but the shadow side of being so open, honest, and transparent is that when you get accused by a few people about holding something back from them or hiding something from them, it just strikes at the core as to who I am, so I've had that kind of struggle of man, being a transparent person, an honest person, has been such a strong part of my identity. It doesn't mean that I tell everybody everything, but sometimes it's misperceived that I may be holding back sometimes, and I'm really not. It's like really that's all there is. I realize I'm starting to speak in the abstract a little bit. I don't want to veer off course, but I will say that I wanted to, even in that case, present the flip side of it. The great side of it is by being so honest and transparent, if you ever come to hear me speak at a conference or ask me a question that I'm on a panel, you can bet that I'm going to give you a straight candid answer and not in a way that is mean and spiteful, but it like, "Hey, based on my experience, this is how I feel. I'm not going to disregard anybody else's, but here's radical candor in effect." Then the shadow side of all of this too is that I've struggled when people have said that, "I feel like you're holding back," or, "You said it this way or that way." That's been a little bit of a struggle of mine, but certainly glad that I made that move five or so years ago to start making that part of who I am publicly.

Shantel: Well, I can't wait to take a look, and I apologize that I haven't already and will be sure to look at it definitely on this show. Speaking of candor and honest, you sent over your bio, and you mentioned homeless for a little while. I think that we'd leaving the crowd hanging if we didn't touch on it slightly after the Burger King comment. Can you tell us what happened there?


Kit: It has nothing to do with Burger King. I'm sure Burger King's a fine company. Actually, I'll reserve that. I'll reserve my comments on Burger King. I just worked there. I just know they paid me for a couple years in minimum wage before I went to college. Yeah, so there's a talk that I get invited to do occasionally that's entitled Homeless to Hyper-Growth. What I do is I actually tell the story from 1996 to 2016, so essentially a 20 year history of my life from self-selecting into being sort of homeless to be an entrepreneur and to do whatever it took to get into that mindset and operation of going out on my own. Then, of course, it ends with running a company that has broken the Inc. 500 and has been in hyper-growth and exponential growth mode. That talk, the homeless part is actually at the very beginning. I address it pretty head-on, and I say that my mother would actually appreciate me letting everybody know that it was not like I didn't have a room to go back to to sleep in or whatever. Their home was always open for me to come back. However, I selectively chose to go without a place to live in order to stay. I was living in Nashville at the time. I grew up two hours or so away from Nashville in Kentucky, and there really wasn't anything back home for me to go back and do over my summers in college, and I couldn't afford to live in the dorm. I could afford to sign a lease. I didn't have any money. I opted to essentially go a homeless route. Luckily, I will say, I only had to sleep in my car a couple of nights or my studio a couple nights. I always had somebody's floor that I could sleep on or a room that I could maybe give a little bit of money for maybe a month or so. I stress the fact that I selected that as being very extreme to say if I'm going to be an entrepreneur and if I'm going to go out on my own, I have to do whatever it takes, and so I'm doing this. I'm going without a place to live so I can figure this shit out. I basically give that point, but then I also talk about very super briefly ... I should have actually led into this description this way with you, that there's a Lifetime movie called Homeless to Harvard, and I basically tee it up to say there's two reasons why my life is nothing like the wonderful Lifetime movie depiction of Homeless to Harvard. One is that my mother and father had a place for me to stay if I ever wanted to go home, and then the other reason it's not like that movie is I didn't get into Harvard. I got rejected actually. I like to pull up a rejection letter from Harvard on my slides whenever I talk about that point. I was not destitute, but I chose a life of not having shelter in order to be in a city that essentially was a big city that I could strike out in and try to start a company in.

Shantel: That's neat. I think that it shows you've had to sacrifice something to accomplish that dream because that dream was more important to you than something else. I think that when you have a business, there are some of those things that you have to weigh. Do I get to spend every weekend with family or friends, or are there going to be times ... There's a lot of things that you constantly have to weigh, I think, and that's a great lesson. I have a couple more questions for you, Kit. One would be what's the best piece of advice or the thing that you would advise people running a business in those early growth phases.

Kit: I often repeat a piece of advice that was given to me by another entrepreneur, which is to never lose momentum. Of course, if anybody knows their physics, it's harder to build it back up if you lose momentum, so essentially to build that speed back up. The idea too in a business is whether your momentum is gaining market share or whether it's the growth of your revenue, whatever momentum means to you, product or services company. Focus on not losing it because building it back up is extremely difficult. For me, that has actually been something that momentum meant something different from one stage of our growth to the next. At one point, we had to hire a lot of people at once and part of the momentum since we're a services business was that we actually ... When we transitioned from being a studio into an agency, we were actually creating ad campaigns and managing and optimizing ad campaigns. We actually had to hire a whole new team to scale that part of the business. The idea around momentum there was okay, we got to build, we got to hire those people. It was extremely sort of focused. Now, that's more of a mature business for us a few years later and so momentum means something a bit more like client fit for us and the direction that we're going now here at 10 years in to us being a company because we figured out a lot of stuff. There's still a lot of stuff to figure out, but for us, that definition of what momentum is is a little bit different. I stand behind that advice that a fellow entrepreneur gave to me as being something that you just don't want to ... I mean, I could think of more, but to me, that's something that stood out that really influenced me.

Shantel: I think that's great. For a personal moment, I mean, with traveling quite a bit and speaking engagements and being more public, how do you recharge, if and ever you feel drained personally to maintain that momentum?


Kit: Gosh, this is like an Oprah moment in a way. I'm doing really poorly at this right now. I've always been really proud of my own attention to a level of mental self care because it's very, very, very difficult. I approach this in a couple of different ways. One is I for years have had a meditation practice that this year has really eroded. I'm not proud of that, but it's been something that is extremely centering, and we all need. Everybody is talking about meditation now, so awesome, I'm totally on that bandwagon. Physical self care, I've really fallen off that. I used to run. I would try to do five miles every morning. Most of the time it would be like three, and I wish I could have done five, but I didn't have the time. With travel, it's quite difficult. Failure, failure, strike one, strike two on those two things. I would say I know that I'm falling short, but those have been really strong things that anchor me in the past. The third thing is mental health. I'm extremely vocal about entrepreneurs making sure they have good relationship with a therapist, especially if you're in a committed relationship where you have a significant other or a spouse that didn't sign up to be an entrepreneur, you did, so to bring all of the rollercoaster home with you is the absolute wrong thing and can wreck relationships. For a few years now, I've had a regular relationship with a therapist in which I cycle through the challenges that I feel as an entrepreneur, as a business owner, and honestly that ends up being most of what I process through. When we hit the Inc. 500, the Kauffman Foundation reached out and wanted to understand ... The Kauffman Foundation, of course, is just a huge resource out of Kansas City for entrepreneurs and is one that I kind of long had heard about and was a fan of, but when they reached out to get some sense of what's missing currently that an institution like the Kauffman Foundation could give to entrepreneurs, I thought back to when I started my first company and dropped out of college to do so. It was very difficult to figure out how you could even register online a new company. Now people don't even have to drop out of college to start new companies. There's entrepreneurship programs, and it's much more endorsed by universities to go through a program like that as opposed to dropping out and striking on your own. There's also many funding sources now. It's a different world than it was when I first started my first company. What is missing is the psychological attention that entrepreneurs need because this is a different type of individual that has chosen to break apart from the security of a tribe often to start their own tribe or to go out there and to try things that haven't been done before. It can be lonely. It can be challenging. There's only so much that you can do on your own. Having somebody that's trained to actually help you process through those emotions and those feelings in good times and bad is something that has been extremely valuable to me. That's one thing that I haven't waned on, even though maybe my meditation practice has waned and some of my own sort of physical exercise has waned, I make sure that from a therapy perspective that I'm in there and working with somebody that can help me process through things. Your significant other is not your therapist. You need somebody else to help you out, and if you're an entrepreneur, you know that you're facing things that a loved one can't help you out with, they will accidentally give you the worst advice ever, and to have somebody that just helps you process feelings so much is what I'm talking about there has been really valuable to me.

Shantel: Well, I appreciate and thank you, Kit, for being so honest and vulnerable and sharing some tips and a little bit more about your life. How can people get in touch with you if they want to learn more about you or Look Listen?

Kit: Yeah, so my email address is Kit, K-I-T, @looklisten.com. I always say that even if I don't respond to an email immediately, I eventually get to it. I have a pretty good track record of eventually responding. I'm on LinkedIn as we had mentioned, and then, of course, through our company social Look Listen. If you have show notes, I'll give you all that info. I hope that any of this has been helpful. I don't know. I should have probably maybe cursed more to make it more interesting or told fantastical stories, but hopefully some of this has been helpful to anybody. I'm very giving of advice or experience share more often than advice. I'm happy to actually talk to anybody that might reach out.

Shantel: Thank you again, Kit. Really appreciate it.

Kit: Yeah. Thank you.

Shantel: That was great.