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 II of our conversation below or go back to Part I where we discuss Jeb’s thoughts on self-discovery, songwriting, education, religion and parenthood.

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:  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:  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:  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:  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:  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:  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:  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:  And antiques.

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

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

Joe:  Reject away!

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

Joe:  My intentions?

Jeb:  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.

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