For my Keyhole Marketing business, I talk to entrepreneurs and explore the plot twist that led them to start their businesses.


Jeb Banner is the founder and CEO of SmallBox, an Indianapolis-based firm offering consulting, branding, marketing, and website design / development services. More importantly, he’s a humble guy with a unique, ever-evolving outlook on life. He continually challenges me to reevaluate areas of my life, while at the same time remaining open to having the mirror held up to him. Three years ago, we started a conversation over coffee that continues to this day. And so it was no surprise when we met in September that we picked up—almost mid sentence—where we’d left off before.

You can read Part I of our conversation below and Part II here, where we discuss his search for clarity, growing through marriage, the plot twist in his story that led him toward becoming an entrepreneur, and how he deals with FOMO (the fear of missing out).

On His Journey of Self-Discovery…

Jeb:  I think the reason people want to have these conversations—even though there is definitely some element of ego involved—is that they’re learning about themselves. They’re curious about themselves, and when they’re asked a question they’re now able to see themselves or understand themselves in a new way. And I think that that’s part of the value—the awareness that’s created in the interviewee, you know?

Joe:  Yeah, yeah.

Jeb:  You know, I certainly have that experience a lot in my work because people will come in and interview me for informational interviews and, a lot of times, I say, “What do you want to talk about?” Then, by the end of it, I’ve been able to think about something in a way that I hadn’t thought about before and hopefully my questions have done the same to them. I think it’s about that journey of self-discovery. I feel like I’m just beginning to get to know myself.

Joe:  I was thinking of your journey of self-discovery during your recent sabbatical from screens. You said you took that because you feared you were sharing too much. Here’s a fear I wonder about. When you go dark on technology, you have to be really honest with your current state of relationships. You have that regular dialogue with people in the social media world, but then going dark from that means you have to only converse in the real world. There’s a bit of a fear like, do I even have real relationships? If I can’t go to that social media door, what’s over here in the real world? Anything? Did you have any of those fears when going dark?

Jeb:  Maybe, but I didn’t really think of it that way. I wasn’t worried too much about losing touch with friends. There are lots of ways to keep in touch. I haven’t really gone back to Facebook but, if I continue a social sabbatical, if you will, indefinitely, I think at a certain point I’d be more concerned. But my close friends, family, and I communicate through phone and text, which I’m still doing. I cannot disengage at that level. I need to be available. But, when I was in Michigan for a week, I almost had no human contact besides going to a store, and that was really an intense experience that I don’t think I’ve really ever had in my life, you know? Of being that much on an island.

Joe:  You went up there by yourself?

Jeb:  Yeah, for a week.

Joe:  Personal retreat?

Jeb:  Yeah. I mean, I wanted to see what would happen when I didn’t have anything else to do. I was curious to see what boredom might look like and what it might produce. It’s been so long. I wanted to see what my natural state was. My natural state of being, you know? I kind of went into it thinking I was lazy. I know that sounds weird because, if you look at my life objectively, it probably doesn’t look like I’m lazy. But, in my mind, I still work from this default of “I’m a lazy person” and that I kind of drag myself into things with the initial excitement. Then I have to force myself to finish. I’m not a good finisher and so, I kind of think to myself, “Oh, I must just be a lazy person who gets ideas and then has no choice but to keep going.” I drag myself to the finish line a lot of times. I have to surround myself with finishers, or nothing gets done.

Joe:  Yeah, yeah, yeah.

Jeb:  What I found was a little bit different, kinda surprising. I was actually really productive. From 8:00 a.m. until 9:00 p.m., I was going, going, going, and I fell into this rhythm that was very different from my current work rhythm. I’d get up, make breakfast, make coffee, and read. Then, I’d start writing and recording music. I took a bike ride before going back and working some more on something. Then around 3:00 p.m., I’d go into a nearby town and find a place to eat lunch, which is a totally different cadence than my current schedule. My body really liked it. Then I’d usually ride my bike or whatever in the afternoon again and write and record more music. In the end, I wrote and recorded 16 songs over six days.

Joe:  Wow!

Jeb:  I’ve probably written and recorded that many songs in the last 10 years, so it’s not like I’ve been that productive previously. But I just couldn’t stop it. I was listening to lectures by Alan Watts. I was reading a book on Tesla, and I was writing and recording. I was writing some about people-centered work. I was exploring nearby spaces and stuff like that. By around 9:00 p.m., I’d have dinner, and then I’d read and go to bed around 11:00 p.m. After a while, I recognized that was my natural state. I’ve struggled since returning with this — how I can live like that all the time.

Joe:  That’s so interesting. Did you have goals you were trying to accomplish? A vision of what you wanted to come out of the week? Or did you just go and say, “I want to be guided in the moment?”

Jeb:  Initially, I had this crazy idea of writing a book. It was going to be called “Brand Gravity.” It’s all about modern brands having to build gravity, and the gravity is formed by the values and the purpose of the organization. They draw people in, and it acts as this gravitational force. The employees are on the surface of the planet, the customers are in the atmosphere, and the fans are out there in orbit. I had all these graphics by the Brain Twins to go with it, and this whole thing worked out. But, when I got there, I just couldn’t stop writing songs and it was sparked by processing all this stuff from Alan Watts — basically get my head around Buddhism, if you’re familiar with him.

Joe:  No, sorry.

Jeb:  Alan Watts was a fascinating guy. He was an Anglican priest for a while, but also a Zen Buddhist. He was kind of like an apologist for Buddhism, meaning like he wanted to explain it to western audiences. Not in a preaching sort of way, but more of just like, “this is what it is, this is what people do, and this is the idea of the Self. The capital “S” Self. He called himself a “philosophical entertainer.” A buddy of mine, that I ran into right before I left for Michigan, had just done his own retreat and asked, “Are you familiar with Alan Watts?,” I said, “No,” and he said, “I’ll send you some lectures that he gave back in the ’60s and ’70s.” He sent me 58 hours of lectures.

Joe:  Oh my gosh.

Jeb:  Just like an insane amount of stuff, and so I started listening to these on the drive to Michigan. And things started clicking. You know, I was raised Christian…very Christian. It never clicked with me, and it was a sort of mildly traumatic experience—being raised in a faith that didn’t align with my personal experiences. Here, it was something that’s not really a religion but a way of seeing existence as one organism. That we all like the flowers popping out of the same ground, if you will, and so many things that he said in these lectures were…I felt like I was waking up, or maybe starting to wake up.

On Riding the Songwriting Waves…

Jeb:  I started processing this experience with the songs. So, I went in thinking I was going to write a book, but that didn’t happen. Instead, I wrote an album but I’m glad that happened and I feel like it was one of the most transformative and important experiences of my life. But, it’s clearly not a book. So I failed in that regard.

Joe:  I’m so intrigued by songwriting. I’ve got some friends who are musicians, and I’m always asking them questions of what drives them to put the words out there. What’s that songwriting process for you? Does it just get to the point where you can’t not write it or do you have to initiate it sometimes?

Jeb:  Yeah. I mean, there have been times in my life where it’s like, “I’m going to go play guitar,” and hey a song happens! This experience in Michigan was a little different. It was more intentional songwriting, you know? I’d be doing dishes, and the words and melody would come in my head – “Everything is a clue…” And I couldn’t stop it. I had to go write and record that song. I’d ride a bike and the song would be in my head. I had to go write that song, etc. They were coming at me so fast, and I was just trying to catch them.

Joe:  Yeah, yeah.

Jeb:  I wasn’t judging them in any way.

Joe:  Free writing.

Jeb:  Yeah. Yeah, it was almost automatic. Yeah. Whether they’re good or bad or whatever, I can’t say entirely. It doesn’t matter to me at this point. It was an expression of the experience I was going through, you know? Then I made little videos to go with every song so, a lot of what I thought about was sort of—not to get too out there but I guess we are kind of out there already—how underlying all of our existence is rhythm. A wave. A wiggle, if you will. There is nothing that actually can be pointed at and said, “That is it.” It’s always moving. It’s always coming in and out of some dimension, right? To think about something as existing in this sort of like framed, static way is only an illusion that we experience because of our perspective, and our perspective is a very limited one. It’s not flawed. It’s just limited. There is no capital “P” perspective.

jeb-banner-holding-things-close-upSo I went and shot myself holding different objects. The camera is moving, my hand is moving, the background is moving. It was just sort of different objects that represented different ideas that the songs were about. It was a way to sort of visualize the thing.

Joe:  In songwriting, do you get one word or one visual and then build out from that?

Jeb:  It’s kind of like when you’re in the ocean and you see waves coming. You see a big wave coming, right? You see that it’s a wave that you can ride. Then you prepare yourself and you ride the wave. You see that it’s coming, and you start to feel it. The water starts to pull underneath you, and then you just have to make yourself available to ride it, or write it, in this case. It’s about positioning yourself to be ready. Once it’s gone past, it’s gone past. There’s no going back to that wave. It’s about being available for the wave, if that makes any sense.

Joe:  Wow. Yeah, it definitely does.

Jeb:  In a lot of ways, I think I had finally made myself present enough to ride the waves that had been there, that had simply been passing me by because my attention was tuned somewhere else. I needed to be present for the waves.

Joe:  Do you hear the music as you’re writing the words or does that come later?

Jeb:  It depends. Usually, I hear melody and lyrics at the same time. They often arrive at the same time in my head.

On the Flaws in Education…

Joe:  That’s fascinating. I took piano when I was a kid and learned some of the fundamentals. I don’t have the skill to create new music, but I do appreciate it.

Jeb:  I think it’s a real shame the way most people are taught music.

Joe:  Yeah?

Jeb:  They’re taught it the same way they’re taught math. Like, there’s one way to solve this equation. They’re not taught it from a compositional perspective. Maybe it’s more like the way you memorize definitions or the states. You know, memorize the states…memorize this song.

With my kids, I try to say, “Hey, there are other ways to go about this.” My middle daughter is learning how to play piano, and I’m always pushing her to write songs. She’s written some songs. It’s been fun, you know, to see her and then the other two join in and make lyrics. She wrote one about me that’s pretty funny.

Joe:  Oh, cool.

Jeb:  I feel like education so often drains the creativity from a kid, and the idea that education should be about memorizing a bunch of stuff I think is a very dated, if not deeply flawed, idea. Not that there isn’t value in exercising that aspect of your brain, but I think it’s really limited. I also don’t think you should have to remain still at your desk. You sit still and pay attention. What kid wants to do that? So they put kids on drugs to help them sit still.

Joe:  Yeah.

Jeb:  I hate that shit. That’s not a natural human state to be in. No human being was intended to sit still at a desk all day. You know, my dream for my job is to be at my desk as little as possible and to be behind a screen as little as possible.

Joe:  Yeah, yeah.

Jeb:  I’m getting closer, but I’m not there yet.

On Religion and Parenthood…

Joe:  Shifting directions, I’ve always appreciated our conversations about religion over the years because it’s always changing. We’re always evolving in that respect. Never in the same spot as the last time we talked about it. For me, even while I have the same core beliefs, the surrounding—the way that I relate to those beliefs—is so different. The way that I act out those beliefs is so different. I think personal evolution is necessary. And I think the same is true for you.

Jeb:  Yep.

Joe:  And that’s a long setup for my question about your personal evolution in and around religion and how you share it with your kids. How much do you try to instill it in them or do you just let them find their own paths? How does that play out?

Jeb:  I encourage them to be curious. It’s to challenge what they’re being told and taught. My approach to parenting, especially when it comes to things like religion and societal norms, is to ask questions. Do you believe this? Why do you believe this? You know, why do you want to get confirmed? I try to not be prescriptive and say, “This is stupid,”—using my parental leverage to kind of come down on something. Occasionally, I slip up and do that. But I regret it when I do because I know that my opinions matter to them, if they act like they don’t care. I don’t want them to be too biased for or against something. I just want to ask questions that push them to understand. You know, why are they doing something? Why are they considering something? It’s a lot of question asking.

Joe:  And if one of your kids took on a faith that was similar to the one you grew up kicking back at, you’d be good with that as long as they ask questions?

Jeb:  Yeah.

Joe:  Yeah? Interesting. I ask because I don’t know that I’m in a place where I’d be good if Quinn found the same religious experience I was raised on. I’m still trying to figure that process out because I see the dangers in that and I feel like, as a parent, I want to protect him in some ways. But he’s also only two.

Jeb:  You’ve got some time. I think, you know, at some point every kid’s going to do something that you find completely abominable. That’s how they define themselves. You should celebrate the fact that they’re leaving the nest, even if it’s like painful or whatever it might be.

Joe:  Yeah, I’m with you.

Jeb:  If my kid decides to join a cult, then…not to say that’s what you’re saying but, you know…

Joe:  Yeah, right.

Jeb:  I’d want to talk about why is this the right thing for you and, in general. I’d want to try to lead with questions, not with the answers. For my family and for my work, creating awareness is far more powerful than asserting my authority. You know, I think a lot of leaders lead with fear and favors. I want to lead with vision and values, you know? I want to lead with, “here’s where we’re going. Here’s the big idea. Here’s what we care about.” Inspire people, not scare the shit out of them. Which unfortunately is too much what parents and business leaders do.

Joe:  Yeah, I hear you. I’ve worked in those environments.

Jeb:  Yeah, it’s terrible. It’s awful.

Joe:  It’s interesting to hear you talk like that because I wonder, do your kids sometimes see you as dad—the business owner—talking to them as employees or do you feel like it’s still a parent/child relationship?

Jeb:  I would say my wife has to remind me, “You’re not at work,” because I can be somewhat directive. Like “you do this, I do this, we’ll do this.” I can sometimes give marching orders at home because that’s what is sometimes required of me at work.

Joe:  I don’t picture you like that in the workplace. I see you as more of a delegator and letting everybody own their own piece.

Jeb:  Yeah but, there comes a time…this is something I think about a lot with leadership…you have to flow between the servant and the superhero mode. You have to flow between being that servant and saying, “How can I create clarity for you? How can I help you do the best in your job? How can I clear the path for the greatness you have in you?” and, “All right. We’ve got to take care of this now, guys. You’re doing this, you’re doing this, you’re doing this.” Then signaling when you’re switching hats, right? That’s hard.

Joe:  Definitely.

Jeb:  Super hard. I’m not very good at it, but I identify that the need exists for both roles.

Comments are closed.