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In Episode 13 of Content with Teeth's The Come Up, meet SWFL Career Coach Jason Teeters

A Career Coach for the Jet Set

The Come Up Episode 13 Video Transcript

Scrappy:

What up, what up, what up? I’m Scrappy. Welcome to The Come Up, a video podcast featuring Southwest Florida entrepreneurs, business leaders. We’re sponsored by Content With Teeth, a creative content agency with over 20 years of experience right here in southwest Florida. And as you can see with this fathead, they do it big, really big specializing in copywriting, video production. They got content, that’s for sure. And if you’d like to sponsor, come up, or be a guest, hit me up @heyscrappynig or text Mike at 21,000. Today’s guest is Jason Teeters. He’s a fascinating dude. He’s a nurturing lead at Collaboratory, a non-profit organization where he helps people overcome emotional, psychological, and technical problems in collaboration. He’s also owner of JetSetState, where he is a lifestyle designer for creative entrepreneurs. Welcome, Jason.

Jason Teeters:

Wow. Thank you so much, Scrappy. So happy to be in this space with you, my friend. So happy to be a part of this conversation today.

Scrappy:

Yeah, I’ve seen a couple of your videos. You’re an outgoing dude.

Jason Teeters:

My blood type is B positive. I was once told.

Scrappy:

Well, definitely positive, that’s for sure. Collaboratory, and then you have the JetSetState is kind of like two different worlds of technical, psychological communication, emotional consultation, if you will. Can you break it on down for us?

Jason Teeters:

Yeah, yeah. It’s really simple. Now, it’s probably been almost close to 19 years ago, I started, JetSetState, was really focused on creative entrepreneurs. My wife is a wedding planner, and so I found myself in a lot of spaces with content creators, photographers, videographers, hair, makeup, and a lot of them really had this… Most entrepreneurs were able to create something out of nothing almost, right? They had this passion and people wanted to pay them for it. And oftentimes for creative entrepreneurs, they shy away from the business side. And so for my background, one of the things that I started to recognize is, how can I support creative entrepreneurs to keep turning their side hustle into their main hustle, allowing them to keep moving in this space and create a life for them. And so that really got me in this space of helping design a organization or a business that works for them, which along the way really got me involved in helping larger organizations and communities figure out, how do you design a system that allows you to compete or to participate at all levels?

Scrappy:

So, that’s a pretty cool niche. Creative entrepreneurs, helping them out. What’s been the biggest struggle other than financial for them?

Jason Teeters:

I think for a lot of creative entrepreneurs it’s really that motivation, right? ‘Cause oftentimes, it takes a lot to move forward and say you’re going to be a creative entrepreneur. But once you take that first step, you hope that it’s… You’re going to land in this really beautiful space where you’re traveling and you’re just getting business all the time. And I think you know it as well as anybody that often it doesn’t just happen that way. And so really helping take their big ideas and focus them so they can really design a life that works for them, whether it be the timing, whether it be the financial, and so they’re not overworked and overwhelmed, but really focus on moving forward. And so a lot of times clarity and motivation is the biggest piece that then allows for the rest of everything else the true business work to happen.

Scrappy:

Sure, sure, sure. So the creative disposition, what’s the baseline for them?

Jason Teeters:

That’s a really good question. I think oftentimes, we’ve been sold that most creative entrepreneurs are this hustle, 24/7, grind, grind, grind, and they’re just ready to take over the world. But one of the things that I find is they’re really big problem solvers. A lot of times the disposition’s that, “I don’t like the way this is working, I think I could do it better.” And in that process of doing it better, they start to find all these other constraints around either the industry or the environment or the clients or the product or service that really gets them off track. And so they start into problem solving and coming up with ideas. But you know and I know too many ideas makes it really difficult to actually progress anywhere.

Scrappy:

For sure. And you give tips all the time, every day, all day. What’s the best tip you ever gave?

Jason Teeters:

I think the best tip that I ever gave was to get out of your head and get in your heart.

Scrappy:

Interesting.

Jason Teeters:

And I think oftentimes we get so caught up in this perception of what we’re doing and how we’re doing and how we compare to other people, that we have to recognize that this is a long game. This is an infinite game. The idea of building a business, the idea of living life is 80, 90 for a lot of us. I don’t want to be a hundred years old still doing this work. And for me to do that, I think oftentimes I need to just quit getting that in my head and start focusing on and moving towards the things that matter to me, the things that I care about. Because all this stuff is going to be hard, at least find joy in it. Sure. Every step of the way.

Scrappy:

So you’re a big believer in intuition.

Jason Teeters:

Yeah. I am. I think that oftentimes we’ve been told that the only way to know things is between our ears. And I think for a lot of us, we’ve had opportunities and moments throughout our life where we’ve either felt something, intuitively known, had that gut feeling that we ignore because that’s obviously not correct. But oftentimes we find that it is. And I think the more we tap into that, the easier it will be for us to navigate a lot of these spaces.

Scrappy:

JetSetState, you’re an entrepreneur, you’re helping creative entrepreneurs doing that, but you’re also the nurturing lead at The Collaboratory. What the hell does that mean?

Jason Teeters:

Yeah. Collaboratory has this bold vision of bringing the community together to solve every social problem in Southwest Florida in the next 18 years. Every single one of them.

Scrappy:

What are the problems? What are the biggest problems?

Jason Teeters:

I mean, if we just talk about housing, we talk about education, we talk about workforce development. These are really clear. But one of the things that we recognize is that at Collaboratory, we’re not the solver of those problems, we’re the coordinator. And so our idea is, how do we bring people together from all aspects, from a right brain, left brain, from a creative industry to a structural financial industry. We all need us to be able to solve some of these really pressing problems. And my role is how do we bring people into a space to be able to have those conversations, to be able to not only listen, but be heard and operate in a way that we often say we move at the speed of trust. And so how can we start to build that together to be able to make change in our community?

Scrappy:

Are they buying into what you have to say?

Jason Teeters:

I think it’s interesting. I think it’s hard to believe that this is a new way to thin, oftentimes for so many of us, even for myself as an entrepreneur. “I’m going to be the best,” and, “Nobody’s ever going to be better than me.” And we move in that space that we often try to take on more than we really need to. Or we often compete in areas that we don’t need to be competing in. And so I think as a community, we’re having really good conversations about, “Why am I doing this many things when there’s other organizations that are doing this? Why don’t I focus on the thing that I care about and let them focus on the thing they care about?”

And being in a space where you start to hear individuals come together in ways to say, “Oh man, this is a real struggle for me. Oh, we love doing that.” You start to build these bridges that allow people to collaborate. And so long story short, this is 18 years, so we believe by 2040 we want to solve all these challenges. So we’re on the long road. And so we have individuals that have raised their hand. But I imagine along this route, we’re going to start picking up individuals along the way.

Scrappy:

So you have a little Elon Musk in you?

Jason Teeters:

Yeah, I try. I try.

Scrappy:

Okay. We’re talking with Jason Teeters, fascinating guy. Really enjoying this conversation. And we’re sponsored by Content With Teeth, a creative content agency with over 20 years of experience right here in Southwest Florida. As you can see, when we talk about the fat head behind me, they do it really big specializing in copywriting, video production. They got content. And if you want to sponsor, to come up, or be my guest, hit me up @heyscrappynig or text Mike at 21,000. Now Jason, why 18 years? It sounds kind of arbitrary.

Jason Teeters:

Well, I think for us, one of the things that we think about is, what does Southwest Florida look like in 2040? What does the school system look like? What does our water quality look like? What is our workforce development, our housing? It really helps us start to think about who are we speaking for and who are we speaking to, right? Because we know very well that a lot of the youth in this community in 18 years are going to be the parents, they’re going to be the CEOs, they’re going to be the entrepreneurs in this community. And the goal is, how do we carry forward a community that supports and works with everybody to create an environment that attracts the people to come down here, that helps businesses grow, that educates our youth and helps us build something sustainable.

Scrappy:

I think that’s awesome. You’re great facilitators. Is this going on in other communities throughout the United States?

Jason Teeters:

Well, as of right now, we are the first to try this. We call this, we often say, “Welcome to the greatest community problem solving initiative in American history,” because we want to make really clear that across the country, no foundation as of right now has really leaned into this idea of bringing the whole community together to try to solve some of their biggest social challenges.

Scrappy:

Interesting. Very interesting. Jason, I want to do something kind of fun. I want to do some big questions and they’re big questions, but I only want a few sentences for the answers. Okay?

Jason Teeters:

Sounds good. I’ll see what I can do.

Scrappy:

Okay. Dealing with talent, how do you collab with the diva?

Jason Teeters:

I think you let them speak and share their ideas, and then you support that.

Scrappy:

Okay. And raw talent, how do you nurture it?

Jason Teeters:

By letting it breathe.

Scrappy:

Okay. Building trust in a team.

Jason Teeters:

Authenticity.

Scrappy:

Okay. Creative entrepreneurs, not you, you’re an entrepreneur, but your clients. How do they pitch?

Jason Teeters:

They pitch around the outcome that they’re solving for.

Scrappy:

Okay. How do you tell somebody their project is wack? I know you’re not going to say that directly, but how do you break it on down?

Jason Teeters:

Is this what you really imagined for your organization?

Scrappy:

Okay. It’s of nebulous.

Jason Teeters:

Well, they’re always…

Scrappy:

Working away around it.

Jason Teeters:

Yeah. Yeah. They’re like, “Oh, we could do this and this.” And I’m like, “Well, you talked about this. Is that what you really,” “Oh well no, it’s this.” “Okay, well then maybe let’s get back over here.”

Scrappy:

Indirect approach.

Jason Teeters:

Yeah.

Scrappy:

What’s the worst advice you ever gave somebody?

Jason Teeters:

Oh, don’t worry. It’ll work out.

Scrappy:

Come on. I’m sure you gave some worst advice.

Jason Teeters:

Yeah, I think, man, probably my son when I told him, “Well, if they push you, push them back.”

Scrappy:

I think that’s good advice. I’m from New York City.

Jason Teeters:

I got called into the office for that. I got called into the office for that. Telling…

Scrappy:

Are you from Chicago or Indiana? ‘Cause I know you went to Ball State in Indiana, but are you from Chi-town?

Jason Teeters:

No, I’m from Indiana.

Scrappy:

Okay. Very cool. Very cool. And I think your degree is fascinating, industrial psychologist. Now, if one of your clients has a lot of anxiety, how do you talk them down?

Jason Teeters:

I think for me, I often try to figure out what is the fulcrum, what the thing that they’re trying to really solve for. Because oftentimes there’s a lot of things with anxiety, there’s a lot of things that are playing into that, what others think, how they think, what it looks like. But try to get really clear on what is the key thing that you’re trying to accomplish for this moment right now.

Scrappy:

Okay. My boss is a son of a b. I can’t stand him. He’s mean to me. How do I cope?

Jason Teeters:

That’s a challenging question to answer, but I think for me, one of the things that I would say is I always talk about this “me to we.” So what are you doing? Or what is the individual doing to take care of their own wellbeing so that they don’t get wrapped up in thinking that, “This company I work for is me, or this boss is me.” If I don’t have another outlet, then all of my energy goes into this organization or this business or this boss that feels like it’s the same as me. Instead of me recognizing that I have options, I have choices.

Scrappy:

That’s a great one. I appreciate that one for sure. So many of us are mired in multiple jobs, just getting by, just paying the bills, that’s about it. No discretionary income. We feel stuck. What do you tell them?

Jason Teeters:

I think often that feeling stuck is, for my own personal experience, I think the feeling of being stuck typically comes around aspirations for myself. And so oftentimes, it’s really getting back to this. Is that intuitive? Really getting back to what are the things that really move you and how are you doing those on a daily basis? If it’s meditation, if it’s yoga, if it’s reading, if it’s playing video games, whatever it is. Oftentimes when we’re stuck, it feels like the things that really bring us joy are missing from our day to day, which doesn’t allow us the opportunity to get out of our own head.

Scrappy:

I think that’s a fascinating answer, an intellectual answer. But if I’m working two jobs, just no, it’s just frustrating. It’s very frustrating to leverage your way out of that situation.

Jason Teeters:

It really is. And it is a vanilla answer, right? So much of our stuckness has to do with so much of our, has to do with so much of our history. ‘Cause it could be the stuckness around the work, it could be the stuckness around what I like to say, “organizational trauma.” You work in a company, you’re like, “Oh man, I’m just going to try to ride this out.” And then we stay in that space for far too long. And some of it is just a natural fear of breaking the mode. And I think that’s tough for a lot of people to figure out which one of those is making them feel that way, and which one of those do they want to work on first? ‘Cause you can’t do them all at the same time.

Scrappy:

Got you. Collaboratory, it’s a real challenge. You get a bunch of business leaders together, different races and ages and religions, personalities, opinions. How do you get them all on the same page?

Jason Teeters:

I think we focus on the things that we do have in common. I think all of us love living here in Southwest Florida. All of us want clean water, all of us know that every student in every high school across the region will eventually be working in our companies, our organizations, at our grocery stores, at our movie theaters, our gas stations. And so it’s really focusing first and foremost on the individuals that live here and how can we make their life better in some sort of way that allows to give them the agency to quit being stuck, start a business, be involved after school in an education program. And so we try to start with what we have in common.

Scrappy:

Okay. I think that’s awesome. That’s an awesome answer. I really appreciate that. I think too, that in business sometimes, there’s different agendas that are really hard to arbitrate, but for sure, I totally agree with that. How about haters, back stabbers, and gossip queens? How do you deal with them?

Jason Teeters:

It’s so interesting. If you go to the website Collaboratory and you look up nurturing department, that’s what it says right at the beginning, right?

Scrappy:

Okay. Okay.

Jason Teeters:

And that’s where that idea of moving at the speed of trust, because oftentimes you and I both know that to develop a relationship takes time. And we always say, “I don’t want you to leave your ego at the door. I want it in the room because [inaudible 00:18:13] flipped experience can shed light on a way that I’ve never been thinking because I’m only in my silo.” And so creating space for that to happen with respect and with care that isn’t focused around individual or a single topic, but it’s really focused around the betterment of what we’re all collectively coming together for.

Scrappy:

Okay. I’m a big fan of the Buddhist philosophy, living in the moment. How do you get people there?

Jason Teeters:

Scrap, I think that’s one of the challenges, and I think even for myself. And I would often say it feels like something that you would be better at answering oftentimes, because I think when people hear you and they listen to you, they’re like, “Man, Scrappy’s got it all figured out. He’s just himself.” I think for a lot of people, we box ourself up during the week and we have our representatives show up at places we go to. And so really getting people just to be themselves in the messiness and the history of goofiness of all of us, sometimes that’s what’s needed in a space and that takes time for people to just sort of allow that to come out. Because like I said, oftentimes with Instagrams, and Facebooks, and social media, I’m giving you the best that I have to offer. Not knowing that it took probably 30 minutes to take this one shot because the music and the video and all these.

Scrappy:

Absolutely.

Jason Teeters:

Which is why they need Content With Teeth, so they don’t have to worry about that and they can just be themselves.

Scrappy:

Jason, you’re awesome, man. I appreciate your energy and I think that you’re… I’m sure you’re doing big things with JetSetState as an entrepreneur with creative entrepreneurs, and also with Collaboratory as a nurturing lead. We’re brought to you by Content With Teeth doing really big things, content agency. If you want to be part of it, hit up Mike, 21,000 texts or me @igheyscrappy. Jason, awesome man. Awesome, awesome, awesome. Thank you so much. I really appreciate your time, bro.

Jason Teeters:

Thank you so much. It’s such a pleasure to be a part of this, such a pleasure to be able to see you and connect with you again after so long. And I love what you’re doing because this needs to be out there for individuals that are going through that process to know it’s okay to stumble and you have somebody to lean on to learn from and to hear sources of information.

Scrappy:

You want to bust out your socials, maybe get a client out of this.

Jason Teeters:

Yeah, I love it. So you can follow me ig@JetSetStateSetState, Instagram, uh, Teeters Jason is my personal, and then JetSetStatesetstate.com. And then if you’re in the community trying to really make change happen, follow collaboratory.org. You could jump on there and see what we’re doing in the community and be a part of helping us solve some of the largest social challenges in our community in the next 18 years.

Scrappy:

My man, Jason Teeters, thanks for your time, man. I really, really appreciate it and I learned a few things and I… That’s awesome. Really awesome.

Jason Teeters:

Thank you my brother. Thank you so much.

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