Jeb Banner, CEO, Boardable

Jeb Banner, CEO, Boardable

Jeb Banner knows a thing or two about turning ideas into companies. Over the past 20-something years, he’s founded, owned and/or advised a number of businesses ranging from ecommerce to web marketing to software. In 2006, he co-founded SmallBox, an Indianapolis creative agency, where he spent 12 years as CEO.

Fast forward to today, and Jeb has exited client services altogether. He now leads Boardable, a nonprofit board management software company he co-founded in 2016. Jeb joins us to talk about his decision to move from SmallBox to Boardable full-time, and the mindset shift needed to do so. Tune in for insights on making the service-to-product transition, and the trouble with trying to juggle two different companies at once. If you’re a services company attempting to evolve into a product company, or you’re considering a big leap of your own, Jeb has some advice.


Carl Smith: Hey everyone. Welcome back to the Bureau Briefing. Swinging by the Bureau studios today, we have the former CEO of SmallBox, which is a creative shop in Indianapolis, and the current CEO of Boardable, which is board management software, is Mr. Jeb Banner. How are you doing Jeb?

Jeb Banner: Great. Thanks for having me, Carl.

Carl Smith: I appreciate you being here. When we met years ago at one of the Bureau events, and I remember listening to you talk about SmallBox, and you had a bunch of other side projects at the same time. And I was like, this is a guy who is just going to keep experimenting and keep doing things, and then one day he's going to fall in love with something he's doing. Now, I could be wrong. But what I was hoping we could do today is talk about that decision to move on from SmallBox, and go full-time with Boardable. Does that sound good?

Jeb Banner: Yeah. Let's talk.

Carl Smith: How long has SmallBox been around? Talk about starting it and your passion for it, and what led you to this point?

Jeb Banner: Yeah, SmallBox was founded in 2006. I've been running as a number two to an option business before that, we're using web marketing and web design to grow that business. I decided that that was more what I was interested in than selling stuff. We grew from beings, mostly a dev shop, building custom content management systems into more full marketing agency SEO, SEM, all that stuff. Then into brand as we continued to evolve, while dabbling in a lot of different things along the way, which is what you alluded to. With a couple of nonprofits spun out of the business, musical family tree, and the speakeasy. A number of other businesses spun out of their record label, another agency, they were a creative shop, a couple other businesses.

Jeb Banner: I was always experimenting with different ways to productize what we were doing and never really finding something I could land on. We built a content management tool for wrangling content as you build a website. We built an employee engagement platform that we use internally and started to launch with some customers. As I fished about for that product, I increasingly fatigued my team who were just wanting to do, as you can imagine, we just wanted to do great creative work, which is what they've been hired to do, and they had a CEO that was restless and wanting to find the product.

Jeb Banner: Over the last couple of years, we had an opportunity with one of our customers here in town, United Way of Central Indiana, where they came to us asking for a board portal. We've built a number of products through the years for customers. It had been a little bit hard to watch those businesses take off with the tools we've given them. We saw an opportunity to do something different this time, and we took a risk and spun off a little incubator if you will, with my partner Joe. He and another partner in Boardable, Jason Ward, the two of them really concepted this. I have to give them credit, Jason really saw this opportunity and said, let's go ahead and build a beta version on our own dim and then bring it back to them instead of just building the portal which would have cost a lot more money.

Jeb Banner: Then not been evergreen and updated et cetera. That was really the genesis of where Boardable came from.

Carl Smith: Boardable came into being a couple of years ago. Is that right?

Jeb Banner: Yep. Early 2016. The conversations may have even started in 2015. But by the end of 2016, we had a pretty good 1.0. We had some early adopters on the platform, and we were beginning to raise money. So, over the course of that year, we began to see that we are moving towards a business.

Carl Smith: Okay, so you began to raise money. Did you have any experience with that going into this or was that something that was fresh for you?

Jeb Banner: I had zero experience. Well, not zero, but very little. We brought ... This is something that we could dig into further if you're interested. But I really think the alchemy of the founders is super critical for a product company, any business, but product company because there's just all these areas you need to be thinking about and fundraising is definitely a big piece of that. We brought in Andy Clark who is an early guide ExactTarget, which is a company here in India that-

Carl Smith: I know that company. We used ExactTarget back in the day.

Jeb Banner: Sure. Yeah. They went public and then sold to Salesforce. He had a lot of experience. He was the guy that did a lot of their acquisitions. He was one of my partners in doing the Speakeasy. So, we brought him in early as a co-founder, right after we had the beta built. He said, "Oh, I see this. I see the need.' He was chairing the Speakeasy board at the time.

Jeb Banner: He was really a super important add to the team, because the three of us knew how to get that far. But we didn't necessarily know how to get to the next stage. He helped us work with attorneys, and learn how to talk, the pitch deck and everything else, and became critical on our fundraising.

Carl Smith: Earlier this year, at the beginning of this year, I think you said, is when you went full-time with Boardable, is that right?

Jeb Banner: Correct.

Carl Smith: So, what was the trigger that made you say, okay, beginning of the year, I'm going Boardable full-time?

Jeb Banner: Well, when you're raising money, the investors are understandably asking who's running this business. At the time, I was running both businesses. I think I was running both of them pretty poorly. In the sense that I was a pretty distracted CEO on both sides. I was fortunate to have really good people on both sides. And as also during that time, my wife had joined SmallBox, initially part-time just to help us build out our educational offerings, training, et cetera.

Jeb Banner: But over the course of that summer, it was becoming clear that Boardable was ramping up, we ended up raising 1.35 million in-

Carl Smith: Oh, congrats.

Jeb Banner: Thanks. When you start raising that kind of money people start understandably saying, "Hey, we need to make a call here." I was feeling called towards it. I had been doing SmallBox for 12 years, I was feeling a little burned out, to be honest on the service world. I was really excited about this opportunity, and I really have a passion to help nonprofits. They need better tools. I think they've been neglected by a lot of the tech industry, but that's another story.

Jeb Banner: So, I did my annual week in the woods in July, where I go off by myself for a week and think about stuff. When I came back, it was just really clear that I had to start moving things more quickly. Then, I went to my wife and said, "Hey, are you up for this?" She was, but she also said, "This was not my plan. I was not planning to a CEO of the business. I don't know if this is what I want to do, but I'm going to give it a try."

Jeb Banner: That was, to be honest, it was a very stressful time for us as a couple in terms of our marriage.

Carl Smith: I know Jenny from hanging out more than a few times, and she seems amazing.

Jeb Banner: She is.

Carl Smith: She is a truth teller, boy. She's not going to hold back. I think that probably makes for a great CEO, but also makes for a great partner in life as well as business. So, I can imagine the way that she told you, "This was not my plan." You said it very calmly.

Jeb Banner: She was very graceful about it, and we had many many conversations, and honestly, we had some professional help. We needed it. I think when you go through a life change like this you really do need to do whatever you can to protect the marriage. I think we've come out the other side much closer, and much healthier. But Q4 and Q1 were pretty tough to be honest.

Carl Smith: Right?

Jeb Banner: Because SmallBox was not in great shape, I had been neglecting that business because my heart really wasn't in it as much as it had been. When you have a CEO that's off doing something new, it has impacts and sales and everything else. She has completely turned that around and revitalize that business, and it's the healthiest its been in quite a while. It's all making sense now. But getting there was really hard, and there was a lot of days where I had to just drag myself through the day.

Carl Smith: Well, 12 years is a long time. 12 years, I know for me that was when I fell out of love with running my company. I think for you to have that opportunity, and then see that money get raised, which is ... That's validation that other people think the idea is great as well. And then you've got all this trust in Jenny to kick SmallBox in the ass and get it going again. And she obviously does, because she's able to focus on it. Probably, I would imagine when she first looks at it, it's like, "Okay, I just got to figure this out."

Carl Smith: But she's got us a consultant on the side a little bit. So, one of the one of the things that's amazing to me in this whole transition is, I remember talking with more than a few people who've been funded. And they say, the one thing you don't realize at first is that people want you to spend this money, and they want you to spend it quickly, right? They don't want you to ... When you come out of the service side, you're used to being a good steward of the budget, and you have to do the same thing on the product side. But that doesn't mean don't spend it now and get the damn thing done. So, how has that transitioned for you mentally to come into an environment where you don't necessarily have clients anymore, but now you've got investors, people that you've got to show things to. What was that transition like for you?

Jeb Banner: I think it's a transition I'm still going through, to be honest. It's a mindset shift going from a service to a product mentality. This affects all the kinds of different areas of my role as a CEO. For instance, being in the service world, I feel like that's a very talent centric culture by nature, because you're selling the talents of the people that work there.

Jeb Banner: You really do cater to talent and you cater to the needs of your employees, and I think that's good. That's what the business model is. It's a little different in the product world. You're very customer centric. But you're customer centric in an interesting way. If one customer says they have to have something or they're not going to buy the product, you don't bend over backwards. You say, "Well, that's not where we're going with the product, can you move on to the next customer." While still listening to the chorus very closely.

Jeb Banner: So, that's a big big shift. In terms of spending, it's weird to run a company that's in deficit month after month, and the thing that is encouraging to the investors is well, that deficit is getting smaller every month. Yours, you are supposed to run in the red and you often are asking yourself are we under investing? Are we not being aggressive enough? So much of this business is about building a foundation to then layer on, so, a marketing foundation, a product foundation. Then you have to ask yourself, is the foundation ready to be 2 Xed, or 3 Xed? In other words, have we figured out how to put $1 in and get three out? Can we put in another $1000 here? Another $1000 there?

Jeb Banner: The measurement and metrics and data becomes extremely important in the product business in a way that the service business could perhaps become more so, but just doesn't have the same need to constantly measure, to inform spend.

Carl Smith: You had an on ramp time period while you're running both companies. And then you start at the beginning of this year. I'm just curious, what is your education curve look like? How did you get yourself smart?

Jeb Banner: Again, I think I'm getting myself smart. Okay, well, I'll give you a little bit more practical response. But I'm learning it's a firehose experience. It wasn't like I had no product knowledge because we built product for customers, but building product and actually running a product company are very different, because there's just the mechanics of a product business are so radically different than a service business.

Jeb Banner: So, I built an advisory board. This is something that again, Andy Clark was fundamental in. We brought in some very seasoned people like Jay Love, who built a number of companies and sold them in the nonprofit tech space to people on the marketing side, the governance side. We set up quarterly meetings and then worked with them one on one. We have a board that meets monthly. I meet with my investors regularly, I seek out people that are smarter than me. I am constantly buying people lunch and breakfast that run product companies and saying, "How did you do this? What happened when you were at this stage? What should I be doing now?" It's very much being in a constant beginners mindset, which is easy to do for me right now because I am-

Jeb Banner: If I was starting another agency, I'd probably be like cockier and think like, "I've got this." But I don't. I need help, and I don't know the answers, and I'm learning really fast, which is exciting. I'm learning every day. That's something that I missed a little bit running SmallBox, is I felt like I didn't have as many new places to explore in terms of my own talent set.

Carl Smith: Right. So, personally, you were kind of stifled.

Jeb Banner: Mm-hmm (affirmative) I got particularly loved working with great talented people, and working with great clients, but it felt like a treadmill. I felt like that whole hours for dollars thing was just wearing me out.

Carl Smith: Being in Indianapolis, how many of the people that you're working with, and the people on your board are local, and how much of it is a travel situation?

Jeb Banner: Well, our customers are global. That's been of course, it's a product, so it can go wherever it wants to go. But in terms of the advisory board, the board and the investors, the vast majority are within driving distance, local. We have a fractional CFO that lives in Naperville. We have a board member that lives in Warsaw, Indiana. But otherwise they're all pretty much in this area.

Jeb Banner: It's one of the nice things about Central Indiana because of ExactTarget, and these other companies that have been built and sold, there's a wealth of talent. We just brought on a Chief Product Officer that was number two at ExactTarget, and just exited as Chief Product Officer of Emma. He's coming on fractionally with us. Again, somebody much smarter than me, knows product inside and out. There's so much talent here right now. It's rich with talent. So, it's a good place to be.

Carl Smith: What does the team look like right now at Boardable?

Jeb Banner: Sure. We've got five full-time employees, and four fractional, or part-time employees, and we're about to make our sixth full-time hire, which will be a Content Marketing Manager. So, you have myself, you have another person in sales, Brittany. You have Joe who does product. You have Ashley who's director of operations and oversees marketing, customer success and Ops. Then you have Krista Martin, who's our director of product. Then we have fractional for marketing, for customer success, for CFO, CPO. And then we also have a bookkeeper, fractional.

Carl Smith: What does your day look like? Do you have a typical day?

Jeb Banner: Less than I did in the agency world. One thing that's been interesting is I'm not in back to back meetings as much. I was this week, which was crazy, but my days are a little bit more open because I'm in the more of a sales role. So, I'm doing a lot of follow up and engagement because after we stopped fundraising, I immediately switched my time to sales.

Jeb Banner: It's usually, get going around 8:00 AM. Sometimes do a breakfast with somebody. I usually I have a morning meeting, most likely internal. Then I usually have a demo at some point in the morning or the afternoon, maybe two demos done remotely, screen share. Often, I have a lunch meeting. Generally, two to three meetings a day. My day is focused often on moving deals forward and closing. Then the bigger strategic pieces, we had a three hour board meeting yesterday, and advisory board meeting earlier this week.

Jeb Banner: So, there's a lot of times I'm having these more strategic sessions, and so I'm preparing for them, creating content for them. I'm going over the numbers, I'm looking at the CFO. The typical CEO stuff of just making sure that all of the different pieces are moving in the right direction.

Carl Smith: Now, this question, I don't have any insight, nobody's contacted me and asked me to ask you this, but, do you feel lonely? Because the CEO of a service shop, it can be very lonely. I'm just wondering, on the product side, does that correlate, or do you find that you're more of the team?

Jeb Banner: I feel much less lonely than I did in the service world. Because I made the mistake. And I think if I could go back in time, I would do this differently, of not building an advisory board. I didn't have an advisory board, I certainly didn't have a board. I had a co-founder, but he wasn't involved in the business in the same way as you would have a board member.

Jeb Banner: I talked to Andy Clark, who I mentioned earlier was the chair of our board. I talked to him almost every day. When we come up with the key moments, I'm engaged with him, with Jason Ward, who's also on the board now, with Audrey Beckman is on the board as our advisors. I don't feel like I did before/ Because I'm surrounded.

Jeb Banner: Also, there's an accountability layer that's in place here that's been very healthy for me and helpful because before I didn't have anyone to answer to really. I could call the shots and make decisions that are almost weren't the right decisions. But, now I have to explain myself to a board and to investors and advisors and to employees that have ownership in the company. I think that this is a good dynamic for me, I need some accountability.

Carl Smith: I think this concept of advisory board and obviously, you're at Boardable, so, you have to have a board. You have no choice if you're really ... Exactly. But this idea of an advisory board, I could be wrong, but I think it's probably foreign to most people that are running digital shops. So, could you just talk about how you decided who to invite? What skill sets or roles or personalities you were trying to put on the board?

Jeb Banner: Yes, absolutely. We look at where the areas of the business. You have product, you have marketing, you have customer success, you've got the space itself, board governance. You've got the industry in terms of nonprofit tech. You've got different areas like finance that you want depth in. You go out and you try to find some of the best people. Obviously, technology being one of those too.

Jeb Banner: Some of the best people that are around in each of those different zones. You try to have at least one person for each of those bases, if you will. And then they get a stock stipend. They get stock, and that's a two year term, with quarterly meetings, and then we bring them in for one on one consultations as we get to different decision points in their area of expertise. That's just been super critical for us, and it remains so.

Carl Smith: That makes sense. The way you just laid it out and described it, makes sense. But I don't know that I ever would have gotten there. But then, that's part of what you're saying. You're finding people who've been there, you're finding people who've had the experience to help you along. So, that makes perfect sense.

Jeb Banner: Again, I think I should have done it with SmallBox years ago. It would have been very beneficial to have people that I had to report out to quarterly who could ask the hard questions. It's very easy for a CEO to convince their employees of the crazy idea they just came up with, right? It's different for an outside group who can look at it more objectively and say, they call bullshit.

Carl Smith: What advice would you have for digital shop owners who are thinking about taking the leap?

Jeb Banner: My number one advice and this is not really new advice, is don't try to serve two masters. Now, you may say, "Well, this isn't what you did? " Yes and no. We really separated Boardable in terms of its incubation from SmallBox. They were operationally completely separate; different founders, different DNA. So, don't try to turn your service business into a product business. I know in 37 signals, did it way back when, boy, I think that's sent a lot of people down the wrong rabbit holes. Maybe, you can pull off the hat trick. But I think the best thing to do is if you have a product opportunity, build a team around that opportunity to give it autonomy, put it outside of your ... Counting outside of your leadership team. Everything else, let it exist separately.

Jeb Banner: Even if you're sharing some back office things, it needs to have that autonomy. Don't try to just make it a project in your company. And then I think, you've got to at some point just make the leap. If you're really committed to doing that, you got to make the leap. Otherwise, it's going to starve without leadership if you're the leader that needs to be believing in.

Carl Smith: All right, Jeb, I'm happy for you. It feels like you got out and found something new, and I'm happy. I want to check back in, like maybe early next year and see what's changed and keep the story going. Does that sound-

Jeb Banner: Yeah, I'd love to. I always love talking with you, and I love the digital bureau [inaudible 00:24:36] community. I really have a heart for agencies and the work they're doing, and they're just great people. So, any chance to share my journey with them and to bring any kind of value I can, I'd be happy to do that.

Carl Smith: Well, that's great. Well thanks again for swinging by. All the best with Boardable. To everybody listening, thank you so much, and we'll be back next week.

Jeb Banner: Thanks.

Carl Smith: All the best

Photo via SmallBox