The F Word with Jacob Johnson, Gitwit Creative

He built one of Tulsa’s top creative agencies. He led multiple tech startups and raised millions in seed funding. He’s the reason Tulsa has a new city flag. To the outside observer, Jacob Johnson’s journey has been one success story after another. But behind the curtain, he’s like all entrepreneurs. He’s experienced failures like dropping the ball on the creative process, missing the mark on communication and hiring the wrong people. Listen as Jacob talks about the key lessons he’s learned as he’s dealt with his mistakes and evolved as a leader over time.


Jacob: The goal isn't to make the pain and the failures go away. The goal is to get better at dealing with them when they do come.

Lauren: This week on The F Word.

Jacob: Yeah, I've learned a lot over the last couple of years, and everywhere I turn there's more blind spots.

Lauren: Jacob Johnson, the cofounder and owner of Gitwit Creative.

Jacob: I had somebody send me that Ted Talk that that showed horrible city flags, and there was Tulsa's flag. And so I'm sitting here going, "I think I have the team to do this entire thing, and I think I have to do this."

Lauren: Welcome to season two of The F Word podcast. We are excited to be back. Today's guest is a true leader in Tulsa's entrepreneurial community. Jacob Johnson is the cofounder and owner of Gitwit Creative. Gitwit is a digital product and marketing company known for finding really innovative ways to take brands and products to the next level. In addition to leading Gitwit, Jacob has been the cofounder of multiple tech startups, and through that, he's raised over $30 million in seed funding. If his name sounds a little familiar, it's probably because Jacob's also been in the news a lot this past year. He was one of the main leaders in the campaign for a new Tulsa flag. But of course, Jacob didn't just stumble into success and land at the top. Some of his startups have failed, and he's experienced anyone's fair share of criticism. I’m excited to dive into that today. Thanks for coming, Jacob.

Jacob: Thank you.

Lauren: Let's start at the beginning. You founded Gitwit in 2008, a couple years after graduating college, and you actually started it with one of your professors from the University of Tulsa.

Jacob: That's right. Yeah, I knew I wanted to do something creative. When I was in school, creativity was relegated, at least in my mind, just to the advertising and design side. I took some of those classes, and I really enjoyed it, but I really just liked the fundamentals of business too. Dan Fisher, my cofounder, Dr. Fischer at that time to me, was the first one who had introduced me to this idea of: there are people out there who are using creativity as a weapon for building products and building companies and introducing innovation further upstream. That was the seed of like, "Yes, that's what I want to do."

Lauren: How did you get it off the ground?

Jacob: We started working together because I had helped put together a plan for how TU could teach creativity because at that time I was like, "Man." I started reading books by Tom Kelly, David Kelley. They started the D School at Stanford. They run an agency called IDEO, which is a design firm. They invented everything from the Swiffer to the Apple mouse, and that's where I was like, "This is the type of stuff I want to be doing. Why aren't we teaching this?" Like teaching people how to ask questions or how to dig deep and go do ethnographic research, watch people, build empathy. I wrote this little bit of a manifesto for TU, and then they said, "Yes, let's put together this program." That was my first intro into it. Quickly into that, I realized I needed to be working not in an academic environment, but in a much faster pace. I looked around. I talked to a few different companies. Didn't find what I wanted, so I just went out and pitched some ideas to some companies I knew and was lucky enough to have a couple of them say yes right out the gate, and that was the birth of Gitwit.

Lauren: I love that. For people who don't know, what services do you offer?

Jacob: The chain of what we do starts upstream with the research and discovery. That's stakeholder workshops, helping build business models, into then customer and user discovery. If it's a product, that's user discovery. Who are these people? What products do they need? Then we get into the design prototyping side of things. We have a strategy team who then helps formulate either messaging or product strategies. And then we have a product team that helps design and build digital products. And then we have the full content and go-to-market team on the marketing side. That's everything from building the web properties, building everything from videos to digital ads. And then a campaign team that gets those out into the world in the various different channels.

Lauren: You have developers, you have business people, you have creative artists, video people. You just have a huge team.

Jacob: We have a random amalgamation people. We have everything from an economist, to somebody who went to Cambridge for screen media, somebody who studied astrophysics at Princeton, who's much more of a quant. Yeah, it's a random mix of people, who then plug in different ways.

Lauren: Through that team, over the past 10 years, you've grown a ton, and you now have huge clients around the world. One of your clients is a technology company that does predictive analytics for oil companies. You have a Japanese company that makes autonomous bulldozers. (Which is awesome. I have to ride one of those someday.) You have a company in Ada, Oklahoma that makes one of the nation's best selling pregnancy pillows. Really you're all over the map. You've grown a ton. But with growth comes growing pains. What are some of the growing pains that Gitwit what has gone through?

Jacob: I think the easiest one to point to is hiring, is people. The unique thing about a service-based business like Gitwit is your product is your people. Some of the biggest challenges have come from, "How do you hire for what you need today and tomorrow?” Because you come across these big opportunities, and it's easy to then just focus on skills. "I need this skill, and if we get it in.” That can maybe help you for a few months, but then you look back and like, "This is now not what I needed." I think that's been the toughest part. Have you hired for people not positions? Have you hired for mindset not a skill? Everyone talks about “you have to hire for culture.” It's easy to say those things. Actually building a process to repeatedly do that is so tough.

Lauren: How you do that? What have you learned through that?

Jacob: The first thing I've learned is Jacob can't lead the process. Jacob falls in love with people. When I sit across the table from somebody, and they tell me what they're excited about and what they're good at and how awesome they are, I believe everything. In fact, I don't just believe. I then build my own picture of how good they can be. That was the first lesson is Jacob doesn't take first meetings. Because then I come back and I'm all excited. I'm like, "Hey, I just met this person." Then everyone else is like, "Oh, well, the boss is in love with them, so I bet they're awesome."

Lauren: Yeah, "We have no choice" kind of thing.

Jacob: Yeah, so that was the first lesson is, don't just randomly go grab lunch with people, get excited and come back and tell everyone. Have a process that puts you behind.

Lauren: What are some of other lessons?

Jacob: Be methodical. Have a process, and trust that process. Have that process be a combination of testing for core values as well as the core skills of critical thinking and ability to understand deeply but explain simply. That is one thing that I've learned, that no matter what position, whether it's a writer, whether it's a developer, they have to be able to go very deep in what they do. But then they have to be able to come out of that and explain very crisply what it is that they learned and what they've done. I used to think that that was a skill that was relegated to the storyteller. I now understand that, if you can't explain it simply, then you just don't understand it well enough. So doing that objectively through a test. We give out an assignment now. I probably shouldn't spill this because it's a timed assignment. People don't know what it is. I'm going to anyway. This is nothing innovative, but we send out an assignment that says, "Explain Instagram to somebody who's never heard of Instagram." It's a seemingly innocuous assignment that most people just can't do. Most people can't just simply explain what is Instagram. They lose all the context of this as somebody who's never heard of it, and they start talking about features and hashtags. If you truly read that as somebody who'd never heard of it, it would make no sense. That's one of the tests that we use.

Lauren: Have you ever made a poor hire?

Jacob: Oh man, yes. We've made a lot of bad decisions in hiring, and most of them are not like, "Man, that person sucks." It's usually just was not a fit for what we needed. Most of the time, that's a cultural thing. I think we have a culture that is incredibly high expectations, with really low direction, and that can be really challenging. So A. We have to learn to support people better. But B. Some people just ... They can't thrive in that environment.

Lauren: What do you do? Do you just wait until they burn out or do you let them go early rather than extending out the process?

Jacob: I think some of the failures were then not being clear with people of, "Here's where you are ,and here's where we need you to be." I think people can feel when it's not working, and so to sidestep it, and to wait for somebody to burn out doesn't do you or them a favor. I've learned having those hard conversations opens the door for people to push back as well. I think that's one of the failures, is just letting things lag or talking about it with my cofounder Dan, rather than directly to that person. Then also not realizing that you can part ways with people with grace. You can still really care about people and let them know this isn't working and try to help make sure that they land on their feet both financially and give them smooth transition. I think that was the other part of it, is I've made some mistakes of not doing that as well as I could've in the past.

Lauren: I think, in creative companies like yours, the rock stars, the ones who are just killing it, the employees that, if you had an employee of the month, they would win every month, can get burnt out really, really easily and quickly. Especially as you take on new business, if you don't hire enough people. Have you had employees, stellar employees, get burnt out. How do you adjust that and help restore the health of your organization?

Jacob: Yeah, so I think one of the things that I've learned about getting burnt out is, it rarely comes from doing things that you love. It usually comes from... If you were to draw quadrant in the top left hand corner is “things I love and things I'm great at.” Things in the top right are “things I love but I'm not that good at.” Then in the bottom right hand corner would be "I don't love them. I'm not good at them." Those are the things that can be a huge drag, that even if you don't have many of those things on your plate, they can absolutely crush you. I think having those conversations with people has been key, and then also realizing that... Professional athletes clearly understand what they can do with their body. How hard they can push it, and then what those recovery times look like. They understand that in both intervals of daily recoveries, weekly recoveries or even gearing up for these big races and then needing these huge recovery cycles. I feel we don't do that to ourselves in business, and we should. We should look at ourselves and say, "Look, this isn't a yes or no, a linear, I have to quit or I have to." You have to pace yourself and be intentional. I think having those conversations definitely helps.

Lauren: Your company gives unlimited vacation to your employees. I think a lot of business owners would see that as risky. Could think that their employees would take advantage of that. How have you seen that play out for you?

Jacob: Yeah. The opposite is actually the risk. The risk is not that people will take advantage. That's easy. If you sit back and you think about risk as the likelihood of something happening, combining the impact of it does happen. You have to break risks into those two different things. The likelihood of that happening is probably pretty low, and then the impact of it happening, is also low because you can curb that really quick if somebody is taking advantage of it. The more likely scenario is that people don't take enough vacation and that the impact on that is that they don't get those times to reset. When you look at it through that lens, it actually becomes more important to then let people know that this is unrestricted vacation, so you can manage this. You have to have those conversations. It's not something that I would advise people do to just to sound good, or to have a-

Lauren: A recruiting device.

Jacob: Yeah. No, it doesn't work. It's tougher to manage than just having a system where people can log their time and they know and you know. Yeah, it can be dangerous.

Lauren: One of your biggest clients is Hilti, which is a power tool company. Hilti recently moved their headquarters from Tulsa to Dallas. I think this happens with entrepreneurs more often than we may think, where a big change happens with a client that's totally out of your control, and it leads to a lot of uncertainty. Can you talk a little bit about Hilti’s transition and how that affected your business?

Jacob: Yeah. Luckily, we had maybe two years before we started doing a lot of work for their global team. They're all based in Liechtenstein, so we know we can work very well with a company remotely. That made us a little bit less scared about the move. It was still scary. It was like, "This is a huge client.” It's a big company for Tulsa to lose them regardless. There was that backdrop of, had it happened two years earlier, it would have been much scarier because they would have made a larger portion of our revenue.

Lauren: Because they were what? Like over half of your revenue for a little bit?

Jacob: Yeah, for sure. Well, especially when you first start a company, a lot of times you've got one big customer that's a huge portion of your revenue. It takes time to then grow and build A. reputation and B. enough capacity to then diversify from that. It's pretty standard, especially in this industry, for that's how you kick off. Yeah, but there for awhile in the first year, I would say probably 80% of revenue. A huge chunk of it. By that point, they were still large. I would say maybe 25% of revenue, so that's still a huge chunk. Yeah, for sure. It was scary, but that makes you take an honest look at you, at your financials, at your team, at your plan for how you're going to be a good partner. I think, at the end of the day, it was scary, but when that fear sets in, what you do with it is completely up to you. We're definitely the type of people who jump into action. Ultimately, it's been really good. I think we're now relied upon for really important projects, and some of the stuff that we've lost are the more transactional day to day stuff that is probably more repeatable by a lot of agencies. Like, "Knock out this quick campaign or brochure." But we still are engaged with the C-Suite on some really critical stuff. It's been really good for us for sure.

Lauren: Was your staff really worried about that? Did you have to do some calming of the team?

Jacob: I don't think so. No, we're pretty open with what's going on. I guess I'd have to be honest with myself that maybe I don't have the most empathy for concern or fear, just because that's not my natural worrying. It's not my natural state. Maybe there was more than than I would see. But that being said, I think people fear the unknown more than anything. We've tried to always just be super open, so as soon as we found out, we let everyone know. I let them know, "Yeah, so this is a little scary, but here's what we're doing." I'm sure there was some type of angst, but not having a shroud around it, probably helps.

Lauren: As you've grown- and grown exponentially- have you ever found yourself dropping the ball on some clients while trying to take care of others?

Jacob: Yeah, for sure. It's dropping the ball on process because a business like ours exist because it's very hard to create a culture of creativity and innovation inside a successful company who's generating $20 million to a few billion dollars a year in revenue. Their systems are built to protect that revenue, as they should be. Now innovating becomes tougher because your culture is now set to protect that thing, and so to innovate you have to have this culture where people are constantly trying new things, people are constantly have the ability to fail. Ultimately, that's why people come to a company like Gitwit, is because “we need somebody who can help do that for us.” When we fail for a client, we've rarely failed in terms of not delivering or blowing a budget. We've got a lot of integrity in our team to where that rarely happens. Where the failures have happened are when we didn't push hard enough and we didn't design process, and ultimately they could have gone other places. When I look at the failures, if somebody could have gone to a lot of other places and got exactly what we did, that's a failure because we do charge more than others, and people then expect more. They could have just gone to a freelancer and gotten the same thing. Those are the failures that scare me.

Lauren: On top of Gitwit, you've also founded four other different startups, which have all gone through different phases of growth and have gone through some type of failure. Some don't exist anymore. Some sold but not for as much as you wanted. Can you talk about what you experienced with those tech startups and any common thread you learned throughout those?

Jacob: Yeah. Tech startups are a unique beast because we live in this fantasized world of how quick and easy it is to get a product up, has created this just rapid and massive amount of innovation. That's something that we've proven to be really good at is helping get products off the ground, getting them to market. It just seem it should be pretty easy then. We're in a better position from a team standpoint, from a financial standpoint to be able to make a run at this. The common thread between the challenges that we've seen is how hard it is to build an organization. To build a product is one thing. To get the first few sales is one thing, and we've done that really fast, quicker than almost any startups that we've seen. Get a product ramped up, get it out there and get your first few paying customers, and then have just assumed, well, say I've just assumed different stages of it. The first one I just assumed that “now it'll just take care of itself. Now people will just love it, and then it will go,” and that’s just not how it works. There's this quote, and I don't know who to attribute it to, "People don't build companies. People build organizations and organizations built companies." That was probably my biggest blind spot for a solid five years, of just this not understanding. I would try to point at other people and blame it on them, and I didn't realize that a founder's job is to put together an organization. Is to get everything pointed in the right direction, get the right team on board, get everyone incentivized properly, make sure that they understand their roles, make sure that they've got good goal set and they understand how that's affecting the overall vision. I had no concept of that. Our first couple of products, one of them just had some market-fit challenges that we weren't able to get through because of organizational issues, because we weren't committed to the type of iteration and innovation it takes to then learn what users want. The second one hit it on the nose, had quite a bit of recurring revenue. But we failed to put together a sales team and support team and everything you need to truly engage people. That's then what drives further product innovation is that voice of the customer. There's a couple that I look back now and both of them could and should have sold for $10 to $100 million. Neither of them were going to be monster unicorns. But both of them had solid understanding of the market and revenue. But yeah, the common thread is that focus on organization.

Lauren: At what point did you have this aha moment of, "Wait, I'm supposed to be building an organization not a company.” How did that click and how did that propel you forward?

Jacob: I wish I would have had an aha moment. I still am struggling with that. I think it's a nature of... Yeah, I've learned it slowly over time. I think I can just now synthesize it into an overall thought over the last maybe two years. But I've learned bits and pieces of it because part of that is hiring. Part of that is then the structure of the company. Part of that is then the structure and processes rather for how that company works together. Part of that is, “how do you do good goal setting?” Revisionist goal setting, where you're constantly changing that. There's a lot of different pieces to it that once you learn, once you know what you don't know, you then realize, "There's so much more I don't know." That's the hard part about learning. It is the more you learn, the more you realize how little you actually know. I definitely feel like that when it comes to organizational strategy, organizational design. Yeah, I've learned a lot over the last couple of years and everywhere I turned there's more blind spots.

Lauren: What do you do to grow in that area? To learn, is it reading? Is it a mentor? Is it bringing in consultants?

Jacob: I pick up the phone, and I call people all the time. I have my all of, I shouldn't say all of my growth, most of my growth has been seeded by one guy. He works at Hilti. He's their head of People and Culture Globally. Lives in Switzerland. He travels all time. When he is in the US, I figured out where he is, and I jump on a plane and and I take him to dinner. He's the guy who seeded all the corporate athlete stuff that I was talking about earlier. He's really into that right now. He is plugged in at a very high level in those conversations. I got to meet the Chief People Officer, Chief Culture Officer of HubSpot and have kept her contact information. And then you just find other people about town. There's a girl, Samantha Macpheter at eLynx's, is one of our clients too. She's just another brilliant when it comes to people. I just pick up the phone, and I call people. Every time I'm challenged with something, I just chat somebody up for 20, 30 minutes, because you need somebody to ask you a lot of questions and people who've seen these things before. That's probably been the biggest one. And then, of course, I read a ton. Pick up every single book I can get my hands on.

Lauren: What are you reading right now?

Jacob: Right now I'm rereading Principles by Ray Dalio, which is an unbelievable book. Ray Dalio is absolutely one of a kind. He was the CEO and founder of Bridgewater, the world's most successful hedge fund. From a culture standpoint, nobody gets it like him. Principles by Ray Dalio is one I'm reading. I finally grabbed a fiction book for the first time in awhile, when I was in Santa Fe last week.

Lauren: That's good. That's a healthy thing.

Jacob: Yeah, I read maybe one or two a year. I grabbed a nice AI fiction book. But yeah, those are the two that are on my desk right now.

Lauren: Something I think we don't talk about often enough on this show is raising capital, and you've raised $30 million dollars. What is the advice you'd give to an entrepreneur who's looking for funding right now?

Jacob: Yeah. I can't say I have raised $30 million. There's always been a team. No one person does that. A decent chunk of that, I was very much involved in but was not the person leading it. Of that $30 million, I would say $10 of that I have been the tip of the spear. The challenges that come along with that are really, “how do you simplify your story?” You raise capital on a story always, and you've typically got to get it done in 30 minutes or else it's never getting done. I think one of the challenges is learning how to really be objective about the person you're talking to and whether this is a fit or not because so many people will listen to you. I think that that was one of the biggest learnings is, you just go and once you the right fit, get the story seeded and then go from there. Again, it comes back to if you can't explain it simply, you don't understand it well enough. I think people like to talk about the business side of things and what has served us really well, let's talk about the user. Talking about the market and the need and the problem in the world and how this addresses it. That's what gets those things done. You absolutely have to have everything buttoned up, but that's the core of it. I think the second thing that I learned pretty quickly is, if you're going to go into a pitch meeting, you better be ready to cash that check and spend it that day. Otherwise you're not ready to take on money. I think, when the milestone that you have ahead of you is so large, you forget to look past it sometimes, and this is very dangerous in raising capital because getting the capital is just a stepping stone. You've actually gone backwards at that point. You've gone into the red at that point, and now you've got to climb forward. I think that is a feeling that I could describe, but you never really know that until somebody hands you that big of a check and then you realize, "Oh man, now I got to-

Lauren: Do something with it.

Jacob: Yeah, "Now I got to do all of these things." I think that's certainly a piece of it.

Lauren: Are you selective about who you take money from?

Jacob: Yeah, of course. I think you're selective as you can be, is the reality. If you go back to this organizational side of things, that's part of your organization now. Is your shareholders, and so you have to think about it through that lens. But at the end of the day, yeah, there's only so selective that you can be.

Lauren: Have you heard “no” very often?

Jacob: Oh yeah. Well, so the interesting thing about the no’s that you hear when you're raising money, very few just come out and just say “no.” You usually get sandbagged, and so you just have to learn that that is no. You then have to just address it or else you learn nothing, because if you feel this like, "Okay, well, I'll go kick this." You know that's a no, you can either pretend it's not and hope they call you back or you can address it right then and there and try to learn. Yeah, that's the funny thing in raising capital. Especially if you're doing it with Tulsa investors because people are so nice and it's a smaller city. A lot of times it's not just a definitive no, and here's why. It's typically like a-

Lauren: A passive-

Jacob: "Yeah, we'll be in touch." Then you never hear from him again until you see him at a restaurant.

Lauren: What are the questions someone should ask when they're getting this “no” vibe, that aren't aggressive but still lead to learning?

Jacob: No, be aggressive.

Lauren: Really? Okay.

Jacob: Look, you have to, I want to say, be aggressive. The fundamentals have to be there. You care about these people and their pain. If that's not there, then I can't really help you anyway. But assuming that you do actually care about what this person thinks, and that you're genuine with it, be aggressive because you're opening up the door for them to be honest with you when you do that. If you think about that, you're making their life a little bit easier, and what they're trying to do is avoid conflict. If you can initiate some conflict, you'll actually do yourself and them a favor. Then maybe what they get out onto the table in doing that is something that's easily addressed and maybe it's not. But now you both don't have to walk away with any open loops about that conversation or pretend we'll be in touch or anything like that.

Lauren: Okay. I want to shift a little bit, let's talk about the Tulsa flag. I love it. I have the sticker on my laptop. We incorporated it into our latest 36 Degrees North T-shirts. It's flying all over the city. It's really terrific. You did this whole project for free, and you told me you've probably invested about $40,000 into it. Why?

Jacob: Oh man, why? That's the ultimate question for everything that we do with Gitwit. I'll start with the answer that I believe but probably doesn't make the most practical sense. That is, I've always had this personal view of doing things for the community or fixing things around me or for people where, if I'm uniquely suited to solve something, then I have to jump into action. Because I'm the type of person who likes to just jump into action on everything just because... Yeah, I can be over confident in my abilities to do things. My wife will never let me fly a plane because I’d definitely be that person who suffers from the, "I can do this” mentality and crashes one. However, I had somebody send me that Ted Talk that showed the horrible city flags, and there was Tulsa's flag. Then I realized that, if anybody can do this, and to my knowledge, no citizen-led effort in the US has yet to be adopted by their city. I knew that it wasn't just design a new flag. It was run a campaign to get this thing adopted by the city. When I say the city, I do not mean the government. I mean by the people. That was 100% of the goal. I'm sitting here going, "I think I have the team to do this entire thing and I think I have to do this." It was literally that much of a, "I can't turn away from this. I've now seen this thing. I can't walk away from this thing that I've just seen." I called Joey, Joey Wignarajah. If you don't know him, you've been probably living under a rock because everyone knows him. He is just an incredible human being, who also happens to understand the inner workings of government in general, but specifically here in Tulsa. I called him, and I was like, "Maybe if we joined forces on this, we could not only gets public adoption, but maybe get city adoption, which would then increase public adoption as well." He didn't even hesitate. There was no pitch involved. He jumped in head-first on it. That was the genesis of it, was just seeing this thing that I'm like, "I think we could do this."

Lauren: So it became this huge passion project that the city has grown to love. It's everywhere. It's literally everywhere. But the city rejected it, and they're picking it up again now, but initially they rejected it. Former Mayor Dewey Bartlett had a harsh Facebook post about it. Rejection is a type of failure. How did it feel to be rejected on this passion project?

Jacob: That rejection was just fuel for the fire. Joey is a complete optimist when it comes to this, and he was like, "I see no reason why any of these people won't be completely for it." I just knew, if you're trying to introduce a new symbol, think about how all... I've done enough branding work to know, that when you change things, it automatically upsets people. If you introduce a new symbol for a city, something that everyone has ownership... We live in a democratic society where a city is just a representation of the people. This is your city. I'm going to come to you, and I'm going to show you a symbol and say, "This now represents your city." That's a really hard thing to do. There's no prior associations. It doesn't matter whether you like it or don't like it. That's just a challenge and that's a hill to get over, so I knew we had that in front of us.

Lauren: You didn't feel defeated when city council was like, "Eh?"

Jacob: Oh, not even close. If I could have written a script for how I wanted this to get adoption, this is the script. It needs to be people first and then them to follow. It gave me a whole new view of how different people see their roles as elected officials. I think maybe that was the frustrating thing because there were some people… Like the late Counselor Patrick was incredible to us, and he wasn't exactly for it. But he was very genuine in his concern, in his input on what he thought we should do, and there were no qualms about it. But yet we had other counselors who just didn't like the flag. They thought that was their role to decide whether it was a good flag or not. That, to me, was very frustrating. To sit across from people who are just like, "I just personally don't like it." That to me was just not the role-

Lauren: When they're supposed to be the voice of the people.

Jacob: Yeah. Then those people can say, "Well, I talked to a few of my constituents. They don't like it." Anyways, everyone ultimately has their justification. That part was frustrating but ultimately the way it's played out, I couldn't be happier about.

Lauren: Hopefully, the city adopts it. By the time this comes out, they might have.

Jacob: Hopefully, but I don't care. Because at the end of the day, if people adopt it as the symbol of Tulsa, that is 100% of what we're after, and the city can help that. But maybe by, I don't know, rejecting it again, it'll give people more fire to then adopt it. I don't know. It'll play out how it plays out.

Lauren: You're not worried about it?

Jacob: I'm not worried. I do hope they adopt it, but if they don't, I'll just say I don't care.

Lauren: You really love Tulsa, and earlier I was listening to another podcast that you were in. You were talking about Tulsa, and you said, “it's easy to be fearless here.” What did you mean by that?

Jacob: Fear is this, “what happens if I don't succeed?” I think you're living in a place where, as long as you don't care about the political side of it, financially you can go after whatever you want and you always have something to fall back on. It's easy to get a job, the low cost of living. It's easy to meet people, to get introductions to people who can help you. I always said this about TU, it's the ultimate padded room because it's this small university, in a smaller city, and you don't have the world watching you. It doesn't feel like so… I think just some of maybe the trappings of some of the larger, more successful tech cities you don't have here, which I hope breeds more fearlessness.

Lauren: Looking forward, what are some projects you're working on right now that you're really excited about?

Jacob: This predictive analytics product that we're working on with eLynx it's one of a kind. It really is. They have assembled an unbelievable team. They brought over the head of analytics from Price Waterhouse Cooper. They ran a 500-person analytics team. They have brought in some of the most insane talent I've ever seen on a team, and most of it's here in Tulsa. A lot of them are working remote or traveling in. But everyone right now is talking about machine learning and artificial intelligence. I have gotten to peek under the covers of enough of these initiatives to know, most of it is smoke and mirrors. Most of it people don't really know what they can do with this data, or how they can actually... They know that there's this promise of this thing, and so they're hiring these data scientists and quants and people, and most of it, there's not much being yielded. This is a team who has built some unbelievable predictive models. Have operationalize them, have proved them, and we're getting be at the heart of the product strategy and with the end user designing all the interface layer, understanding how that impacts and teaches these predictive analytics models. How we can then use that to influence these users and these entire companies, and we're getting to see, in realtime, this change full companies and create massive economic value. That one is just a crazy, exciting time to be a part of a team that is just absolutely reinventing themselves. They have thrown every shred of what they thought they were in the trash and a very profitable company who's just said, "Screw it. We're taking a left turn." It's just rare to see companies do that, and even more rare to have them bring you on as a partner that isn't just like a vendor. Who's being in the middle of it. That's probably one of the most exciting things that we're working on.

Lauren: I would love to keep a close eye on that. The name of that company again?

Jacob: eLynx, E-L-Y-N-X.

Lauren: The last question that we always end with is: how would you encourage an entrepreneur who's in the midst of some failure, whether that's internal or external? How would you encourage them moving forward?

Jacob: We do an exercise at Gitwit, where somebody's first day, we all sit around a table and we write down on a card, "What is it that you wish you would've known on your first day at Gitwit that you now know?” Everyone writes a personal note to this person. We give it to him. Mine always has some variation of what I'm about to say and that is, "I wish I would've known that these challenges and these failures are always going to continue.” Because I used to think that, "Oh, at some point I'll be good at this, and I won't have to be dealing with this stuff." I think about it like running. There's no marathon runner who's just now they run a marathon just doesn't hurt anymore. It always is going to hurt, and there's always going to be pain. You can just get good at dealing with that pain and overcoming that pain. The goal isn't to make the pain and the failures go away. The goal is to get better at dealing with them when they do come up. I think that's probably the advice I would pass on is, don't look at your situation as being like, "I'm in this rough spot and once I get through this." No, you'll always be in that. Get your head wrapped around that. That it's always. If you want to be an entrepreneur and you want to grow something and you want to be ambitious, anything in life, you want to be ambitious, you're going to have that pain, and you can either be like, "Yeah, that's a part of this,” and face it with a smile. This mentality of like, "Okay, this is the next challenge. Let's go.” You'll get through it, but if you fool yourself into thinking, "Once I get through with this." You just say that a lot, "Once we hired this person, or once we get to that level of revenue." Once you get there, there's going to be another challenge.

Lauren: Such great insight, Jacob. We're excited to see where Giwit goes next. Thank you so much for coming into share with us today.

Jacob: Thank you for doing this. This is awesome.

Lauren: On the next episode of The F-word…

Libby Billings: I didn't take a salary for the first year. It was not making money. I took a second mortgage out on my house.

Lauren: Libby Billings talks about flirting with failure as she worked to build her restaurant, Elote, and revitalize Downtown Tulsa’s Deco District.

Dustin Curzon: The F Word is brought to you by 36 Degrees North, Tulsa’s basecamp for entrepreneurs. To learn more about our workspace, community and resources, visit The F Word Season Two is recorded in the KOSU studio and produced by Lauren King.