The Journey To Success One Stepping Stone At A Time With Jason Teeters

Updated: Jan 4


DP 7 | Journey To Success

The journey to success never happens overnight. We’ve heard of successful people having a clear picture of what they wanted their lives to look like from a young age, but what if you don’t have a vision of how you want it to be? In this episode, Kate Hixson talks with Jason Teeters, a man with many different chapters and paths in his life. Growing up from a humble background, Jason eventually worked with the United Nations. Don’t miss some amazing life lessons from Jason as he shares how you can live a life by design that is not dictated by where you come from.

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The Journey To Success One Stepping Stone At A Time With Jason Teeters


We talk a lot about the journey to success. We know without a shadow of a doubt that it never happens overnight. On past episodes, we heard from a supermodel, a highly successful commercial photographer, a world champion kayaker amongst others. In each of these cases, these people, these high performers had a clear picture of what they wanted their lives to look like from a young age. What if you don't know what you want your life to look like? What if you don't have some big end goal that you can relentlessly pursue? On this episode, we're talking with Jason Teeters, a man with many different chapters and paths in his life. Jason grew up in a small town in Indiana, Muncie. A place only known because it's home to a university, Ball State.


It's the type of place you only get to if you're looking for it. Jason's parents were hardworking and humble and kind, but they had a simple life in the sense that neither of them received educations past high school. His mother worked in finance, eventually rising to a VP position. His father started working for Shell as a truck driver. He eventually retired as a terminal operator with huge accolades under his belt, including one of the longest safety records. How does a kid from such a humble background grow up to eventually work with the United Nations or with The Rockefeller Foundation? It's hard to imagine the steppingstones that would take you from point A to point B, especially without a clear path. Find out on this episode. We're exploring life lessons from the world's preeminent overachievers and learning how to crush.


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Jason Teeters, welcome. I am excited to have you on the show and to be able to pick your brain and hear about all the awesome things that you're up to.

It's such a pleasure, Kate. I'm excited to be here and have this conversation with you.

Tell me, what are you working on? What are you up to?

I'm working with a company called SecondMuse. We're a global innovation company that's been working to try to create equitable ecosystems all over the world. My projects have been ranging with Rockefeller with their Food System Vision Prize, reimagining what the food system will look like in 2050. I've been facilitating ten of the finalists as they work through that project there. I'm working with a gentleman, Tyrance Billingsley, over in Tulsa, Oklahoma as he tries to reimagine Black Wall Street, but Black Tech Street where he's trying to entice large BIPOC owners and founders of tech companies to come to Tulsa and build their dreams there.

What an incredible and inspiring projects, and important work. I seem to recall there was something with the United Nations. What was that all about?

It was fortunate that I've had the opportunity to work with our CEO of SecondMuse. We did a business summit for the UN this 2020. We talked about the state of entrepreneurship, the state of businesses, and the state of the economy as it relates to everything going on with the pandemic and how businesses are responding.

How did you get there? I'm thinking of all these different projects that you've described. It's exciting, important and global work, but it's also local work too. How does someone get to that stage, to that career? How did you start? Where did you grow up? Tell us about you, Jason Teeters.

To answer your bigger question, you have to walk your own path and find the nuggets along the way. I started in Indiana, a small little town outside of Indianapolis called Muncie. I grew up there.

I’m quite familiar with Muncie because I'm an Ohio girl. It’s the same neck of the woods.

We have Ball State there in good old Muncie, Indiana. I grew up there and had a hometown experience. Everybody that I was friends with, I went to middle school and I went to high school, and then a lot of us went to college together. Along the way, there were some cool things that I learned. Being an athlete taught me how to persevere in times of challenges. I've taken that with me everywhere I go. That propelled me into my future.


In which sport are you an athlete?

I played high school football, ran track, and then I went on and played Division-1 football at Ball State University.


What position?

Running back.


You're quick.

If you ever see me, I'm a small guy. I used my speed to get away from those brawlers. I try to outrun them.

What did post-college look like for you?

I've had this conversation with my dad quite a few times, it's this idea that in life a lot of us are all playing musical chairs. Sometimes depending on your environment for women and minorities, there's less musical chairs available. Whenever you get an opportunity, my dad has always taught me like, “Give it 365 days, do the best you can be and try to prove yourself.” I've taken that with me everywhere. Right after college, I had this tremendous opportunity to come down to Southwest Florida being an educator, high school teacher, as well as a football coach. If anybody knows me, being a teacher was not what I had in store graduating college, but I took advantage of the opportunity. I learned so much as an educator about how to connect and be somebody who can support others as they move through their life.


What was your favorite moment about being a teacher or maybe even a hilarious moment? Paint a picture for us.

The thing that I always come back to about those times as being a teacher is now I still live in the same community. My wife, I and my kids will be out to dinner. I'll see old students who come up and they'll remember the words that I said to them or the encouragement, or the idea that sometimes I told them, what it was all about, what life was going to be, and how you had to prepare for it. Having those conversations makes me feel during those times I was able to share something that time with those students.


What I'm hearing from you is it allowed you to learn how to connect with people, to build those lasting relationships. That's an important skill that a lot of people don't think about. That idea of connecting, cultivating relationships, staying in touch with people, that's a special thing. I love that. What’s next? You said you weren't meant for teaching. When did you leave? What did you do?

I had this great opportunity with a friend of mine to open up a cigar and wine bar. I used to say the kids were driving me to drink, I might as well be profitable from it. A partner of mine, we worked together to open up a 6,200 square foot cigar and wine bar, front entry and open to the public. We had a private cigar and wine club where individuals could pay yearly to be a part of that group in the back. It was a unique experience, to say the least.


I would think there would be a certain degree of rowdiness inherently by the bar scene. At the same time, it sounds like it's a little bit upscale. As you said, it's a cigar and wine bar. It’s an interesting clientele I'm sure. What did you enjoy the most about that chapter in your life? What were your big takeaways then?

One of the things that has been important in my childhood, as well as leading up to the rest of my career is this idea of relationships over transactions. We can go far, but we can go farther when we go together. A lot of the things that happen at the cigar and wine bar was built around relationships. I learned how businesses and individuals succeeded. I listened to challenges. I had this epiphany that in these spaces, I can do some quick learning. Why reinvent the wheel if I have a gentleman next to me that's a millionaire and he tells me how he did it or how he lost it? I should take advantage of that and use that to create my path as I move forward. This idea of relationship hit home in this time of my life.


How long were you at the cigar and wine bar?


I was there for five years. We've been talking about this with a couple of groups I'm in. This idea of biomimicry. It's using nature and animals and species to design solutions. I feel a lot with my life has been this evolution of who I was meant to become, and a lot of that has been with all these interactions. This constant learning played a role. After the bar, I am wanting to get back into education. I started working for for-profit college which was right around the time that for-profit colleges were getting in trouble. I got to learn a lot during that time about connecting once again, and then they allowed me, and they paid for my Master’s degree. I got a Master's in Industrial Organization Psychology.

When you're growing up in this small town in Indiana playing football, did you ever think that you would go on to get a Master's degree?


I didn't. The only way I got into college was because I knew I was getting a scholarship. I worked hard in my senior year, which made my mom mad because I could have been doing this all four years. Once I got to college, in my first practice, I got hit harder than I've ever been hit before. I knew that I wasn't going to the NFL. Education became a big part. It was natural after teaching and after the bar, there were so many things that I still wanted to learn. The education sector hit home for me to better understand how I can learn as an individual, but also find other individuals like me. I consider myself a curved day. My outlook in school was I wanted to be hands-on. I wanted to be around the things that matter most to me. For the longest time, that wasn't something traditional schooling was about. I use those things to move and progress throughout my life.


What I'm hearing is a series of stepping stones. You're almost hopscotching around. You played D-1 football, that's a big deal. That's a high degree of athletics to be able to excel in that arena. You went on to be a teacher, then you're at the cigar and wine bar, you’re at the for-profit college. It's this disjointed path but I love how you're pulling out the patterns, the themes, and the key takeaways. I love what you were saying about being a lifelong learner because that is so important. We can never stop gaining skills and knowledge. That's what life is all about, gaining experiences.


I do a lot of consulting work with the company called WeLearn Learning Services. They're an incredible group of people. They're so smart, creative, quirky and fun. Why I've been attracted to them is because they have that same mentality of always taking it up a notch, going to the next step, taking on a new training course, a learning course, professional development curriculum. They're so focused on human performance and helping people to become better versions of themselves. I'm hearing the same thing from you. It's cool to have such an intersection. Going back to your story, after the for-profit college, what was your path? What was your next chapter? The many chapters of Jason Teeters.


DP 7 | Journey To Success

This is where my life came at this juncture. I got my Master’s and expecting to make more and move up in the company. During those times, there wasn't a lot of forward momentum as it relates to organizations across the country.


That's important because you said you got this Master's, you have these new skills, this new knowledge, this credential behind your name. Naturally, you think, “I'm going to get a raise. I'm going to get a promotion.” It doesn't happen. What was going through your head in those moments when you realize that you were a bit stuck?


This is a pattern that happens over and over again throughout my life. For a lot of people and a lot of your readers, it is the same thing. You push to reach a certain level and this expectation of what the outcome is going to be sometimes doesn't show up. How do you respond? For me during that time, most things is self-doubt, “Did I make the right decisions? What was I thinking? Could I have done it differently?” I respond, “What next? How can I be of service?” During the time, I did something that I've always wanted to do, and I traveled. I quit my job. My wife and I backpacked to Thailand for about 2.5 weeks.

You were feeling stuck. You said maybe there's some doubt, “Did I do the right thing? I had this investment of time and I was following this path and it's not working out.” Instead of wallowing or putting your head down in the sand, you're like, “I'm going to start over. I'm going to hit pause. I'm going to quit my job. I'm going to travel.” It is important to have those hard stops. “I'm going to pull the plug. I'm going to walk away. I'm going to do something different.” To take that time for yourself. It's a luxury to be able to have that time, have the resources to be able to travel, but I'm sure it was important. I would think perhaps it got your head on straight a bit.


Whether you travel or you sit at home and unplug for 6 hours or 12 hours, what I noticed in that trip was, there were few times where I stopped to be able to think about the journey I've been through. We think about it in terms of like, “What came next and what did we do?” We never get to sit back and take an assessment of, “What did I learn during this time? What do I not want to repeat? How do I make sure this won't happen again?” From that trip, it set my life on a whole new trajectory. I spent a wonderful time in Thailand. I spent the first couple of days worried about like, “What was I doing? Why would I quit my job? Why would I be traveling to Thailand? I need to be sending out resumes.”


Somewhere along the way, I started to recognize my voice, what mattered for me, what was important to me, and what I wanted for my life. That helped me set my North Star, knowing a lot of the challenges I was facing. For a lot of young people around that time is in debt, overwhelmed, overworked, living paycheck to paycheck. Coming back from Thailand, I realized that the most important thing to me was my time. I started figuring out what do I need to do to have the life that I wanted. That got me clear on eliminating my debt, focusing time on the people that I wanted to be around, and making sure that I was intentional about what I'm trying to accomplish day to day.


I love that, being intentional. You said finding your North Star, committing to it, being intentional towards it. What is your North Star? What was this vision that you were working towards?


For me, it's about helping others. As cheesy as that sounds to some extent, that has been the basis of everything that I've been trying to do. I've been falling into opportunities that allow me to use my natural talent. We all find times where we're in that meeting, and they call on us to do something and we have our intellectual talent like, “Give me some time. I'll whittle some stuff together. I think hard and I'll come up with a solution.” That natural talent allows me to show up as me and be me in every situation. Since then, I've been on this constant journey to make sure that I'm closer to being me in every interaction, but I'm also doing what I love to do, which is helping. That looks like to me, helping, coaching, working with entrepreneurs, business owners, and founders who often get trapped in their expensive side hustle. They sometimes never get to make it an actual career. I've been blessed to be in this space for the last 4 or 5 plus years.


I'm thinking about what you said about helping people and how perhaps that is a natural talent of yours. It sounds like it is. You're generous with your time, with the interactions that you have with people. All the length of time that I've known you, that has been the case. You are the first person to say, “What do you need? How can I help? Who can I put you in touch with?” You are a dot connector. I love that about you. It goes back to being generous. Half the time, there's nothing in it for you. You're making a contact, making a connection, showing up, doing a thing, picking up a shovel. You're the first person to lend a hand. I think about gratitude in general, and that idea of giving back. I love how you said that these opportunities have opened up for you over the years. Do you think that there's any aspect of karma involved in that?


Karma has a lot to do with it. I subscribe to the karma and energy. My mom and dad had a great opportunity to move a community which was predominantly white. For me, I had to learn to fit in. Not standing out is something that we all try to avoid as a child. In that process, I was able to learn a lot about people in general. That shift happened again when I went to college and played sports. It happened again throughout my life. I've always been hypersensitive to the idea that often we think people are good and they have everything they need, but it's usually years later, we find out that either they needed help, they struggled, they’re in pain and didn't know how to communicate that.


Knowing what that felt like for me, I've always erred on the side of trying to make sure that I connect with people and let them know that at least someone cares about them. I don't do it in a way of like, “I care about you.” I do it in the way of conversation, “What's going on in your life? Where do you work?” It’s meeting friends a lot of times. That's always helped out because most times we were in gatherings, it's like, “What do you do? That's great. This is what I do.” It goes from there. Few times do we hear somebody say, “That's where you were born? You have two kids? That's your last trip you went on?” I enjoy those conversations. It helps me get to know people. For a lot of us, it shows that some people do want to have conversations and connect with others.


I heard someone said that their favorite question to ask anyone, instead of the small talk or, “Where did you grow up?” You can learn so much about someone from that, but they say, “What are you most excited about right now?” When they're at networking meetings or out at dinner, “What are you most excited about right now?” I love that. That's powerful. It's such a great way to build that deeper human connection, which seems to be a theme of your life, building the connections and the relationships. If you had to think about a theme for you. I ascribed one to you. What would you say is your theme?


DP 7 | Journey To Success

I would say authenticity. It's challenging. Personality by definition is a mask. That’s how I define it. My personality is the mask that I put on when I meet you. In reality, a lot of times, it’s being brave. Not safe spaces, but brave spaces where you could come in and connect with somebody without the ego and all of these other things weighing on you, and just be a human. Authenticity is something that has carried on. I don't know why I've been able to do that in most of my interactions, but it is the thing that I push on the most whenever I engage with someone.


You talked about the idea of being brave or going into situation where you are feeling fearful, uncomfortable. Could you tell us a story about a time where that was the case for you?


It could be like the UN conversation. We've seen what has been going on across the country. There's been a hyper intention to know when a person is in the room of a marginalized group. Instead of me being under the radar, I'm front and center in these conversations around equity and equality. That's new for most individuals in a marginalized group. Being in that UN conversation, there's this natural fear of anyone, “Am I going to look dumb?” in talking to all these individuals. The second part of that was, I wasn't the brightest student in high school even though I have all these degrees. I tend to have this fear that I'm not the smartest tool in the shed in these conversations.


Being black, as well as leading that conversation with our CEO, I wanted to give it the best I could, and being nervous about that. The night before, I was nervous. Somewhere along the way between the four hours from waking up until I had to do it, I realized that I can only be me. I moved into that space with this idea that this is all they're expecting me to come as. It is me, nothing more, nothing less. When I did that, I feel that I was able to create space in that room for honest and open conversations about the state of business in 2020 in organizations and pull that out of a lot of people.


You were saying that you had these fears and these nerves surrounding this huge presentation. We're talking about the United Nations. It's hard to get bigger than that. How did you get past it? How did you truly move away from those fears to then set yourself up, to excel and perform in that moment? Tell me what that looked like to you.


I'm a 4:30 in the morning riser every morning. I try to invest in myself right at the beginning. That morning, I did what I do on Tuesdays and Thursdays. I went for a drive. Nobody is on the road at 4:30 in the morning. I hop in my car, turn on my tunes, roll down the window and allow for this mundane driving all across Fort Myers early in the morning and letting the music and the wind flow through me. I think of all the things I want to say, all the proper things to say, and all the terrible things I could say. I let them come and I let them go. I got back home and around that time, I typically make breakfast for my kids and have these good conversations with children.


For those that have children out there, you know what it's like when you think that you’ve got to be this and that for everybody in the world. Your daughter is happy that you can make toast. It brings you home to this reality of like, “I can only be me in this moment.” The children went. They left and went with their nanny. My wife and I were having this conversation and she was stoked. She's like, “This is huge. You’ve got to be excited.” She could tell I was getting nervous. That made me take a step back as I started to get too hyper about this opportunity. I started thinking, “What is the conversation that needs to happen during this call that can only happen with a group of individuals on that call?”


It's this repetitive thing that happens for a lot of the people you interviewed before, as well as myself. You get in that flow of words and it starts to click. For me, the clicking was this idea that it's all about building relationships. We move at the speed of trust. If anybody on that call does not trust what I'm saying or doesn't believe in me as the individual, then no matter what I said is lost. I wanted to make sure that I showed up, I was present, and I was aware of the space and the time we were in, and understanding that as you move into that space, my job is not to teach anybody, but my job is to hold a brave space so we can have conversations about things that matter.


Given this hopscotching that you've done throughout your life, all these different paths and different chapters, what advice would you give to your former self? Imagine a young black kid in Indiana, what advice would you give?

I have these ideas that I would give some wisdom. You think of Back to the Future, Michael J. Fox has that. He wants to take back so your world will be better. In reality, when we look at the path of our life, we're a combination of all of our actions, opportunities, conversations, and our friendships. I would tell myself to be more open to friendships and conversations, to explore more opportunities, connect with other people. When it's all said and done, we're learning. Whether we believe it or not, every single day, every activity leads to something that helps us solve another challenge or another problem. Those combinations of conversations, discussions and relationships add on top of each other. I would say to just be open.


I love that advice that you were saying about being more open, building more relationships, more friendships, taking more opportunities, saying yes to the world. I think back to what you were saying earlier about the idea of building resiliency, grit, strength, and you combine all this together. This idea of being more open, but also being strong, having resiliency, having some grit and like, “It’s 2020.” It's not easy to be more open, to have resiliency and to have strength. We all want to, we're trying to, but it's not always there. Given your wide variety of experiences and your background, the people that you're working with, those that you've worked with in the past, what would you say about 2020? What is your perspective on it and how do we move past it and forward?

For me, the short answer is we have to be ready to lean into those sharp edges. What I've started to learn, I've taken this opportunity to get better myself. I participated in a program called SoFA Facilitation, where I learned to lead with my heart and with my soul in conversations and in spaces. I'm also taking a program, Design for Systems Innovation and Leadership, where I'm learning how to think about those spaces. The biggest thing that I've taken away from 2020 is that collectively as a society, we're all in pain to some extent. We didn't expect this pandemic to happen. If we run a business, it’s tough, if we lost our job, if we lost our family. There are many things that are happening.

The biggest thing that I've been leaning into 2020 and 2021 is how can I build the necessary resources and tools in myself, and the courage to be able to hold those spaces so individuals can grow themselves. That's been my focus. For a lot of us, being brave and learning from this is one of the things that we have to make sure we take away. That means having a thoughtful conversation with a colleague or someone outside of your industry or learning the best way to support. I've said this to a friend before, some people don't believe in the investment of mental health. For all of us in 2020, now had a real up close and personal with some of the struggles of mental health when it comes to finding jobs, the pandemic and things that we can't control. In this time, it's a good opportunity to get clear about what matters most to you and how can you wake up every day doing that in some form or some way.


Two different things are ringing in my head is what you said about lean into the sharp edges. It’s profound and powerful. It’s not simple, not easy, but that's when the opportunities happen. You have to keep after it. Going back to what you said, resiliency and grit. How do you become resilient? It's by leaning into sharp edges. That's how you build your strength and your mental clarity, lean into the sharp edges. What is next for Jason Teeters? You mentioned you have children, you have your wife, you have incredible work. What's around the bend for you? What are you hungry for?


There are a lot of things that we want. There are a lot of things I want for the future. I want to make an impact. I want to be bold. I've been thinking about this idea that I want to be light. I don't want to create a footprint or a ripple. I want to make sure that I'm holding space with my children and with my wife in such a way that's building deeper connections. That's one of the powers that I've learned from 2020. The more that I've leaned into the things that matter, the more opportunities have showed up. As I look into the future, I want to make sure that I'm a father that my children look up to, the same I looked up to my father. I want to make sure that I'm constantly and diligently trying to be the best husband I can be. Everything else takes care of itself. The happiness of my family relies on me. Every day I need to make sure I wake up and I do that. If I accomplish those two things, anything else that comes, I'm equipped to take care of it. That’s what the future looks like for me.


Thank you, Jason Teeters, for being so generous with your time, thoughts, and perspectives. There's a lot of great advice packed in our conversation and I'm excited to unpack it. Thank you for being on the show.


Thank you. I appreciate you having me.


Where can readers connect with you? Where can they find you online?

On Instagram, it is @JetSetState. That's my consulting business, and same in Facebook. You can find me on LinkedIn, under Jason Teeters. Reach out and say hi.

I know from personal experience that if you shoot this guy a message on any of those platforms, he will unquestionably respond, and if nothing else, he's playing fun. He's a fun, good guy. He's the type of person that you want as a friend in your life. Thank you, Teeters.


Thank you.


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We've heard many powerful things from Jason Teeters. From his concept of focusing on relationships and how to do that with people, to leaning into the sharp edges. We've heard about his multiple chapters in life, all the different things that he's accomplished along the way, and most importantly, we've learned how he's honed in on the specific skills that each experience has given him. Remember, he didn't have this defined goal when he started out, when he graduated from high school or graduated from college, or after his first job as an English teacher in Florida. Each time he moved on to a different step, a different phase in his life, it wasn't even necessarily with an end goal in mind, but yet he did have a goal of constantly bettering himself, learning new things, meeting new people and trying different things out. That in a way was his goal.


For this episode’s homework, I want you to dig in on your different experiences in life, the different places you've lived, the different relationships that you've had, all those stepping stones, all those different chapters. I want you to think about what each one taught you, what skill you gained from each of those specific instances in your life. This way, we're going to be building a skills inventory for you. I provided you with the simple, easy to use template. Go to DauntlessPodcast.com, click on episode seven and download your worksheet. You'll be able to then use the skills inventory to think about, what is your core skillset? What are you the best at? What is your value that you can give to the world? What is your message? What is your North Star? Thank you all for reading, and a huge thank you to Jason Teeters. What an incredible conversation with a truly incredible guy. For more information, go to DauntlessPodcast.com, subscribe, join the community, check us out anywhere you listen to podcast. Until the next episode, be dauntless.

Important Links:

About Jason Teeters


DP 7 | Journey To Success

I’m a Lifestyle Designer

Businesses and Entrepreneurs typically hire me to teach them how to make work not suck. I combine my Industrial Organization Psychology degree with my experience of designing educational and training programs, to help build profitable, scaleable, and sustainable businesses. The biggest thing that matters to my clients is getting results. And I help my clients take well planned, well executed, deliberate action. So they can build the capacity to overcome their fears, uncertainties, and doubts to enhance their decision making skills. Giving them a chance to build a business that rewards them intellectually, emotionally, and financially.