THE TWIST: Inside the Transforming Mind of Jeb Banner

The plot twist…that moment in a story when an event or experience dramatically shifts the future direction of the storyline and all the characters involved. I’ve always found these moments fascinating in real life, and so I started this series—called “The Twist”—where 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 next month, 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).

See all our entrepreneurial interviews.

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.

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

On His Search for Clarity…

Joe:  Back to your personal retreat, I took one myself in July to Yosemite. A week completely off the grid. I came back from it and hit the wall hard, scrambling to get on top of the to-do list and stressing myself out. It was a horrible transition from doing nothing to doing everything. I remember even journaling about being scared about coming back because I just didn’t know how I was going to take this newfound silence back with me and put it back into the world. I didn’t do a good job at all.

Jeb Banner: Yeah, I’m pretty committed to doing this sabbatical thing every year—doing a month off every year with a week alone.

Joe:  The week in Michigan was part of the month off?

Jeb Banner: That was kind of the middle of it. I spent a week with my family, a week working on my house, a week alone, and then a week recording with friends primarily. Then I came back and I had a week in the office where I was kind of shell shocked, and then we had a factory week, which was great. People were like, “Did you come out of your sabbatical with clarity?” I’m like, “No, I came out really fuzzy. I came out just … everywhere.” My mind was not focused. It was interesting. I felt my senses were different. I don’t know how else to explain it. It’s starting to get back to normal, but I found that I was more attuned to flavors. I would lie in bed at night and the smallest noise would reverberate through my body. It’s really interesting. Now I’m getting back to where I’m desensitized a little bit. It’s kind of welcomed to be honest. It’s a little bit taxing to have a heightened sensory awareness.

Joe:  I got that question a lot: “Did you get clarity?” It’s always interesting what we think clarity’s going to look like on the other end. I mean maybe you found it, but it just wasn’t wrapped in a box with a bow on top.

Jeb Banner: Yeah, it wasn’t sitting there in a tidy way.

Joe:  I remember before I left for Yosemite, it was thinking about all the things I wanted to focus on, like some relationships I’ve been struggling with lately. But I really didn’t get any of those resolved while I was there. They’re still a mess. But I also know I put in some deep thought on each one of those things, and I probably went to deeper levels than I’m even aware of. I just didn’t come back and go, “Good, now I’ll just go ahead and close that box and finish that thing up.”

Jeb Banner: Me too. That’s what I was thinking. I’m going to write a book, and I’m going to know the next 10 years of my company and my life. I came back with a better ability to catch the scent. I feel like I came back with my antenna better attuned to what I should do, but I came back kind of a scrambled mess. My wife will tell you this. I was kind of hard to relate to for a little while.

Joe:  After Michigan?

Jeb Banner: Yeah, after Michigan in particular. I found too much stimuli. Imagine if I’d been there two weeks? I came back in this sort of shell-shocked state of mind where I’d gotten so far into my head and into all those things that go on in your mind that … I don’t know…it was hard. It still is. It’s hard to talk about that experience because what are you talking about? To talk about it is to quantify it and to box it up.

Joe:  Was it hard to get in that introspective state in Michigan or did you go there quickly?

Jeb Banner: Yeah, I think the Alan Watts lectures helped a lot. I mean, there was times where I was a little bit, “What do I do?” The first song I wrote was called, “I’m confused.” The lyric was like, “There’s a million things, okay, a hundred things I could do.” Kind of like, okay, there’s not a million things. I wanted to wait on “the other,” if you will. I wanted to not make this about me, and I wanted to connect more deeply with “the other,” which, to me, is the self and nature. I wanted it not to be an experience primarily of the ego.

One of the things that I came out with was an acceptance of the ego. As an important part of who I am as an individual iteration of the larger self, if that makes sense. My ego needs certain things. I should honor its needs. I should also not let it run the show. That balance is to be found somewhere in the middle of honoring the needs of the ego and the fact that it needs to feel valued in some way, but also it has a tendency to dominate. And that domination becomes an unhealthy experience for the larger self.

Who is Jeb? Who am I? How do I go back into this world and talk about me? How do I serve others? That kind of stuff was just in my head the whole time, and I was processing it through all these things. I don’t say I got it figured out at all.

On Growing Through Marriage…

Joe:  When you talk about your personal discovery process, where does Jenny [your wife] stand on that? Is she interested in it?

Jeb Banner: She is. She’s going through her own. She went through this coaching program, iPEC, and a lot of it was about different kinds of awareness—awareness of your perception, other people’s perceptions, being able to identify biases that influence decision making, and to get to a higher level of awareness. So she’s been going down that path, going to these retreats around that.

She’s an extrovert and I’m an introvert. The interesting thing is I felt a real desire to communicate with her around my experience. She did not as much around hers. I think she’s processing it maybe. We have some really great conversations, but it took a while. Like almost a week after I got back, where I was like, “Look, I kind of need to sit down and talk to you about what’s going on with me. If I don’t sit here and try to tell you what’s happening right now, then things are just going to get weirder and weirder.” And she was like, “Well, these are things I’m thinking about going through.” There actually is a lot of connectivity between those two experiences.

When you marry somebody—and you know this—you’re marrying who that person is then, and you’re marrying also the potential of who that person will become. And you’re going to influence that outcome, and they’re going to influence your outcome, right? You’re kind of growing together and apart at the same time. It’s not a simple process. There are times of great convergence and alignment, and there are times of asymmetry and divergence. We have a great relationship, so I knew it could withstand some twisting and turning.

On the Plot Twist Toward Entrepreneurship…

Joe:  So fascinating. So I guess we should talk a little about your business and being an entrepreneur. You had a couple plot twists in your story that led you to starting SmallBox. I know you were doing music for a long time.

Jeb Banner: And antiques.

Joe:  Was it music then antiques or was it both at the same time?

Jeb Banner: They overlapped a lot. I moved here for music, to play music with some friends, and then got into the antiques world. That turned into the auction world. That was basically 1998 to 2005 I lived in that antiques auction world.

Joe:  Was that sort a side gig of sort to support the music?

Jeb Banner: I guess. I wasn’t playing professionally. I’m not good enough to go out there and tour. I kind of figured out through a backwards way that I was good at business.

Joe:  How was that?

Jeb Banner: It was eBay. I discovered eBay in 1998 and started selling on eBay. That really changed my life. I was like, okay, I can do this. I stumbled through that business and started an auction business with my partner Dan Ripley.

Joe:  What happened on eBay where you were like, “I’m good at this business thing?”

Jeb Banner: My dad owned an automotive remanufacturing business. He set up these really intentional production lines where you bring in a barrel, you sort it, you test it, you clean it, repair it, package it—all this stuff for all these different parts. It’s all about creating as much efficiency at your workstation so that you touch things as few times as possible. I think he was really ahead of the curve. He did performance-based pay, so you weigh the amount of work that you did on a sheet. At the end of the day, you’d know how much money you made. Of course, there’s a minimum wage that you would always make, but you could make more money based on how fast you work. Then he did profit share, and he did wellness programs to incentivize people to quit smoking.

I grew up working in that business and watching him create these really efficient assembly lines basically. I took that to eBay. I said, “all right, this is how we’ll inventory things, photograph it, describe it, ship it.” And we created all these efficiencies to take steps out of the process. We were able to move large collections at pretty high rates. I would train a lot of my musician friends to work there. A lot of people I was playing music with, I would hire for $10 an hour to work in the basement of this house on 49th and College. Then I took that approach and paired it with the live auction business that Dan Ripley was starting and that became Antique Helper.

It was just taking that stuff and putting it together. Then we ended up hiring a lot of musicians. Musicians are very industrious…if they show up. They’re very entrepreneurial. They’re creative problem solvers. They’re used to failing. You cannot be in a band and not fail constantly. Learning from mistakes is just part of being a musician. That led to doing stuff on the web, and that led to SmallBox.

On Being a Drug Dealer…

Joe:  Yeah, the web…and screens. I’ve been really fascinated with your distaste for screens that you talk about a lot. How do you weigh that against the reality that your business creates websites that live on screen?

Jeb Banner: I’m a drug dealer. Seriously, I think about it sometimes. I’m a drug dealer in the sense of, if screens are our national addiction, I am creating screen experiences. At least, that’s a big part of what we do. How do we balance that and make screen experiences as humane as possible? How do you make them as close to feeling organic as possible? How do you let the people shine through the screen? Then how get to this outcome, through the creative process, in a way that is as organic and analog as possible? So increasingly, a lot of the work we do with clients with clients is very analog and organic. It’s face to face. It’s sticky notes, butcher block, white boards and human beings talking to human beings. To me, my goal is to bring as much humanity to this completely flat, inhumane thing called a screen. We’ve swapped very rich experiences for very thin ones.

Joe:  Yeah, you sort of want the web experience to be user friendly. In some ways, we want people to stay there as long as possible, right? You’re always looking at their interactions—clicks, views, opens.

Jeb Banner: There are two things I reject about that statement.

Joe:  Reject away!

Jeb Banner: It’s people friendly, not user friendly. I think we’ve got to stop thinking about these people as “users.” Again, that gets back to the drug thing. The addiction, how long they stay, that’s addiction. I know it’s a little radical to say this, but it’s something I’ve really come to believe. We need to think about people-friendly websites—not user-friendly or user-testing. We need to lose the “user” from our vocabulary. We need to stop thinking about how long we can trap and capture them and think about, instead, how much meaning can we create for them?

Joe:  Yep. That does seem to be what people expect, though right? A good web experience gets defined in analytics.

Jeb Banner: That’s stuff that we talk about to our clients all the time. I get it. It matters to them. The next conversation we’re trying to have is to say: these are people, not users. This is not about trapping or tricking them. This is about creating meaning in their lives. If you create meaning in their lives, guess what? Your business will be positively impacted by that. Let’s not focus on tricks. Let’s not focus on captures. Let’s focus on meaning. Let’s not optimize for the trap. Let’s optimize for the meaning. Sure, set up tracking and analytics and pay attention to it, but don’t make that the focus.

Joe:  Is it a tough process to get your clients to believe in that?

Jeb Banner: It’s a tough process to get me to believe in it! I’m still wired for it. Part of our challenge is to sit down with a client and just say this is a moving target. We’re going to be your partner on the journey, and we’re learning as we go. We’re going to learn from you, too. You’re going to teach us. We’re going to learn together. There’s going to be an open exchange of ideas and knowledge. Right now, we’re beginning to think this way. Our message has to be, in essence, here’s where things stand now, but I can guarantee you a month from now it will be different in some way. That’s really hard to sell. To sell the journey.

Part of what we’re challenged with is how do you build systems and processes and sales collateral and case studies around moving targets, right? I don’t know the answer. My job as the company CEO is to constantly pull us towards what’s next. To me, what’s next is to be thinking about the web in a different way, to be thinking about screens in a different way, to be thinking about metrics in a different way. How can we think about this as people, not users? How can we think about this as experiences and meaning, not traffic and hits?

Joe:  And if you swing toward being people focused—not user focused—and it doesn’t pick up in the industry, are you okay with that? As long as it aligns with your core beliefs?

Jeb Banner: Yes, I am okay with it. To be honest, I think that we have been hurt, in terms of our bottom line, by not being more focused and easy to buy, in terms of having very discrete offerings. What we’re selling is kind of fuzzy. We’re selling this thing where we’re like, “Hey, we’ll be that partner on the journey.” And then they’re like, “Hey, I need a website.” And we’re like, “Ok, we’ll get to it.” And, yeah, we often start with something more tangible like a website, to build trust and get things done, but our goal is always to go deeper.

Joe:  Exactly.

Jeb Banner: On one side you have a commodity—it’s $20 for this thing—and on the other side we have a new idea we haven’t even thought of yet that could change everything. And we have no idea what it will cost until we get there. You have to live in this middle range where you have the ability to talk numbers and specifics and meet the checklist of the organization, while still providing this additional value that they didn’t even really sign up for but they need desperately, which is to think differently about all this stuff.

If all we did was crank out very awesome custom websites and stay in our box—our small box, heh heh—and just do what we did when we started, we could be doing all kinds of business all over the world. But it’s boring to just do that. I refuse to run a boring business. It may be interesting to someone else, and I’m glad it is, but it isn’t to me, so I can’t do it. So we have walked away from opportunities that would have been available to us if we had stuck to our knitting and just done one thing really, really, really well. Just build custom websites, for instance.

On His Definition of Success…

Joe:  What’s success look like to you?

Jeb Banner: It’s tied to what makes you healthy. I’ve thought about this a lot. I have a lot of friends that have been much more financially successful than me. They have bigger bank accounts. There’s a time in my life—I’m not saying I’m totally passed it—where I measure myself by that yardstick. It’s still a relevant yardstick. It still has some value as some form of measurement. Certainly, a business should be profitable. It should be healthy and be able to pay its people, pay its bills, and have some money left to grow with, right? That’s just a healthy business.

But increasingly, I define success around how I build up others, how I’m able to create opportunities for others, how others have been able to do the things that they love because of some door that I was able to open, and then from there I see the doors they open for others. It’s a huge pyramid scheme of success and happiness.

Joe:  Yeah and I’m a block in that pyramid scheme of happiness, if you will. You and I first met for coffee in like 2012, and I remember the very first question you asked: “what can I do for you?” It stood out to me. I don’t recall the other things we talked about—just those six words. You initiated the discussion but in a way of “how can I serve you” versus “let me tell you more about me.” And I do link my success from that moment of time. You probably didn’t even notice it, but for me it helped launched me into better knowing who I am.

Jeb Banner: Thanks Joe, I really appreciate that. I think that’s something that somebody else taught me—to ask that question. This gets back to the ego, right? The ego needs to be fed. I accept the ego has to have a certain diet to be healthy. That’s part of who I am as a person. I do have one and it’s not going away any time soon. I’m not trying to live an ego-less life. But other people have egos that they need to create meaning in this world, and they need to do something that they can look back on with satisfaction. They need to feel like they’ve accomplished things. The more that they build up others, the more meaning they’re going to find.

If I can behave in such a way that maybe gives them a template, because I’ve seen others behave that way to me. They’ve treated me that way, people that were “above me” or whatever the perception might be, say to me – “How can I help you?” They went out of their way to make time for me, and they were intentional about investing in me. I felt important and valued. We should all feel that way, because we are.

Joe:  Yeah, it could have been assumed you were interested in helping me—just by making the time—but you actually said the words.

Jeb Banner: Thanks, but I’m certainly not great at it. I don’t do it consistently. This is a good reminder to be more consistent in asking that question.

On FOMO (Fear Of Missing Out)…

Joe:  I feel like you’ve got so many connections all over the place. How are you careful not spread yourself too thin? Do you have to pick and choose at times?

Jeb Banner: There are times when I have to say no for sure. I’ve been able to delegate operationally so much of the business to a really great team at SmallBox. The other organizations I’m involved with have really great themes and great leadership. If I was showing you my calendar, at least since I got back from sabbatical, you might be surprised how open it is.

I want to have more wide-open spaces. I want to have opportunities for serendipity. I want to have last-minute coffees. I want to be able to walk around the building and just talk to people. I came back from my sabbatical with a decreased sense of urgency. There are things I’m missing out on and things happening without me. I know it for sure. It’s definitely happening. Things I would love to be a part of or books I should have read or articles I should have seen or Facebook posts I should have liked…they’re all happening right now without me. I came back with a “Let it go” attitude. Not to say I truly don’t care at all, but I just don’t care as much. And I’m okay with it.

That’s part of this whole thing. I don’t feel like I need to have a packed schedule. If it happens it happens. I don’t want it to happen. I’m a happier person in the morning when I wake up, and I see that I’ve got large blocks of time to write, reflect and have conversations with people. I’m unhappy when I see that I have no space between meetings. By the end of the day I come home drained, absolutely drained. That’s no good for my family.

Joe:  Yeah, that’s a personal struggle I’ve had. I think about taking breaks from social media and then I push back on myself. Not posting things will hurt my business, my branding, marketing. I’m not saying it’s right. It’s just my reasoning sometimes.

Jeb Banner: I think the number one thing you need to focus on is your intentions.

Joe:  My intentions?

Jeb Banner:  Yeah, what do you want to happen? What is the work that you want to do? What gets you truly excited? Setting your intentions. If you’re not making the time in your life to set your intentions, it doesn’t matter what your activity is because you’ll catch all kinds of flies. Setting your intentions and being able to spend every day living as intentionally as possible. I am not there yet, but I feel closer to it than I was before. It’s like peeling the onion. I would say worry less about always being on and worry more about why you’re on and what you want.