Discover:

• How the pandemic sparked Montana's desire for change and led her to the Tulsa Remote program
• The role Tulsa's history, including Black Wall Street, played in her decision to move
• Montana's experience with Tulsa Remote and how the program supported her transition
• The vibrant community Montana found in Tulsa and the power of saying "yes" to new opportunities
• How the move to Tulsa gave Montana the courage to bet on herself and start her own business

Whether you're a seasoned remote worker or considering taking the plunge, Montana's story will inspire you to embrace change and chase your dreams. She shares valuable insights on building a network in a new city, tapping into local resources, and making the most of programs like Tulsa Remote. Tune in to learn how one bold move can transform your life, both personally and professionally.

Transcript 

Justin Harlan:
I'm Justin Harlan, Managing Director of Tulsa Remote. And in today's Remote With series, I have the pleasure of sitting down with Dr. Montana Cain to talk about her journey to Tulsa and some of the inspiring ways that she's gotten involved in the community. Dr. Cain, thanks for being here.

Montana Cain:
Thank you.

Justin Harlan:
All right. So tell us, who is Montana Cain?

Montana Cain:
OK, so Montana Cain is a lover of life. She is someone who is on a very exciting journey to really understand who she is and how she wants to make a difference in this world.

Justin Harlan:
I love that. So many correlations between that, I would guess, and then your journey to Tulsa. And I want to get there. But let's first just talk a little bit about what was your life like before you moved here? Talk us through, who were you before you came to Tulsa?

Montana Cain:
Oh my goodness. I think I was a very just kind of settled person. And I think that's what caused me to want to shift. So right before I moved to Tulsa, I was living in South Carolina. I had a very stable job that I've been at for three years at that time. I bought a home. But I just felt very settled. And I was also in the middle of a pandemic, too. So that pandemic also caused this itch of, you know, you need to rethink life. Like, is this really what you want to do and where you want to be? And then I got a remote job and that opened up opportunities for me.

Justin Harlan:
What was it about the pandemic that shifted that perspective for you, do you think?

Montana Cain:
I think it was just how sudden it was. And I think you learn to appreciate life and all the things that you took for granted at that time. Like going to the grocery store, talking to friends. And it just made me think about how do I really want to live and experience this world? And I think that allowed me to even take the, I mean, we'll get to the Tulsa Remote story, but I think that even allowed me to take the leap of, you're going to Oklahoma. You know what I mean? So I think just knowing how precious life is and how things can change so quickly. I just, I wanted to take advantage of every opportunity and not, I just didn't want to leave this earth with any regrets. So I think the pandemic caused that.

Justin Harlan:
That's amazing. So how did you find out about Tulsa Remote?

Montana Cain:
Google, right? Like how you find out all things, you know, I'm a master Googler. So I got my first remote job. And normally I'm used to moving for a job. Wherever the job is, I will move. But I was like, okay, let's look for young professional, places for young professionals. And so I came upon all these remote programs. One was in Vermont. One was in West Virginia. None of those places I would ever go. Or I could imagine myself there. And then Tulsa was one of those. And I had lived in Durham previously, so I knew about Black Wall Street. And so I knew about the history of Tulsa. And so I was like, okay, I can kind of see myself there. The application was free and so I did the application and got in and it was a really quick turnaround. I got my job in December, applied in December and visited in January and moved here in March. So it was a very quick, like three to four month turnaround.

Justin Harlan:
So you, I think you kind of touched on it, but when you describe some of these other places that you looked into, it was almost like there was a, an association of that place with like, nope, that place isn't for me. So you mentioned Black Wall Street, maybe that's the answer here, but maybe dig a little bit deeper in there. Like, what was it about Tulsa that didn't give you that initial like, that place isn't for me mentality? Like what what about this place made you feel like that's somewhere that I could live and thrive?

Montana Cain:
Well, I didn't know that was a place I could live and thrive. Right. Like I think even my first year, I took the time to explore that. But what made it a possibility for me was the fact that I knew that there was a Black Wall Street and I had just finished learning about that. And then living in Durham, which was one of my other favorite cities, but I wanted something new at the time. I was like, I need a new change. But that connection to, you know, I'm obviously a black woman. And so my black identity is very important to me. And so I needed a place. And when I thought about some of the other locations, there were places that typically did not have a large black population. But Tulsa had a very strong black history. And I think what kind of sold me on it was when I came to visit. So I think the process and meeting, I had my interview. And I remember they were like, OK, you can come and do a visit. And so I was like, OK, I need to see the place before I come. And I think coming here was like, was what made it reality for me. Because I think at the time it was still kind of like, I don't know if I can actually do this. But coming here, everyone was extremely friendly. And I know that we had to come and visit 36. So everywhere I went, there was always someone from Tulsa Remote. I went to go visit an apartment. And when I was sitting in the, you know, in the room talking to the people, they were like, oh, yeah, so-and-so just walked in. She's from Tulsa Remote. So I remember talking to her and her telling me about the program. And she moved here from L.A. And having connections here. So even me using the word Tulsa Remote when I first moved here just opened doors and had other connections for me. And I was like, OK, I can… I can see myself doing it. And it wasn't what I thought. And I think that was the main thing. I knew it was Oklahoma. But coming here, I was like, oh, his feels like a city. This feels like a place where there are things for me to do. So me laying eyes made it possible for me to actually make the move.

Justin Harlan:
So even in the midst of Black Wall Street being a terrible part of our history, and I think oftentimes people, that I know that have considered Tulsa say, that can't be a place for me because of the history for black people in that city. But to you, it was almost like a representation of success and then feeling the connection of feeling the community in your visits. And I think there's something powerful in that of like, it's not a door that's closed. You actually saw it as an opportunity to build and grow.

Montana Cain:
Oh, yeah, because Black Wall Street isn't the massacre, right? I think about the thriving Black communities that existed before the massacre and how we as the community rebuilt after that.

Montana Cain:
And then I didn't even know until I moved here that Tulsa or Oklahoma had 50 Black towns and it was supposed to be a Black state. So for me, that resilience and that power and energy is still here.

Justin Harlan:
I love it. I love it. What was the remote job that you were doing at the time? Because I know now you're an entrepreneur. We're going to get into that. But what was the job that you were doing when you applied?

Montana Cain:
I worked with the Forum for Youth Investment, and I was with their out-of-school time program. And actually, one of my clients was Oklahoma State Department of Education. So it was interesting how, if I look back now, how there were kind of pebbles along the way of, like, Oklahoma might be in your future, which I would have never thought if you asked me. But that was my job there, and I loved it. But it wasn't quite the best fit, so I kind of transitioned to other positions along there before finally saying, all right, let's go do this thing on your own and see how it goes.

Justin Harlan:
And in that moment where you're like, this is what I'm going to go do. I'm going to disrupt my life and go to a new place with open arms and just see what happens. Like, what were you hoping to get out of this?

Montana Cain:
Well, I think I needed to shake things up. You know what I mean? Like, I owned a house in South Carolina. Like, I just had like what you would think of the ideal life. Like, I had a great state job. I had, you know, I owned a home, but I just felt too settled. And I was like, there's like, I need to shake it up. I need something else. And so sometimes you have to get uncomfortable in order to get comfortable. And so I was like, let's just go. And in my mind, I have to like, what's the worst thing that can happen? The worst thing that can happen is I don't like it and I move back. And I was like, okay, can I live with that? Yeah, I can. And so that's what made it possible. But I wouldn't say it was open arms. My arms are still a little folded, you know, because it took a little while for me to like, okay, you know, to accept that this is home.

Justin Harlan:
So talk to me a little bit about your experience with Tulsa Remote. So, you know, how did Tulsa Remote support you in your coming to town? And I know you're a shining example of somebody who's really placed a lot of roots in the city outside of Tulsa Remote. And I want to get there too, but maybe just talk a little bit about how we supported you at Tulsa Remote to get here and kind of build some of those community connections.

Montana Cain:
Yeah, I think for one, I would say the one thing was allow me to visit before making the move. And then there were intentional things when I was here. So again,  at my job where I was working, I told my former boss about Tulsa Remote. She's like, oh, my friend did Tulsa Remote and he's there. So when I moved, when I came to visit, he was like the person who showed me around. And then I have a friend where we went to college together. She's like, oh, I have a friend. So I didn't realize how many people knew about Tulsa. So I think that Tulsa Remote connection helped because he was a part of the program and he showed me around. And then when I came to visit Camp 2, I met Tara, who then connected me to other people. So again, it was kind of, I think for me, Tulsa Remote laid the foundation, right? Like it was a comfortable home base for me because there were always activities to do. We had to come to camp 2. There were two locations. So if I wanted to rely solely on Tulsa Remote for my social needs, I could have. But it allowed me to meet people. So it also connected me to Type Roles, which then allowed me to meet someone else. I was like, oh, I know someone in your sorority. So I'm like, OK, let's connect. So I think for me, it was a great landing point that allowed me to make other connections outside of Tulsa Remote.

Justin Harlan:
And we often use a quote of yours on our website and different things like that, that your ability to kind of find your people.

Montana Cain:
Oh, yeah.

Justin Harlan:
And it sounds like we played a little role in that. But ultimately, it's also people in Tulsa having those open arms where maybe yours were folded and they're helping you kind of open those up.

Montana Cain:
And that's what happened.

Justin Harlan:
Yeah, which is great. Maybe talk a little bit more about like where you found your people and how did those connections kind of come together?

Montana Cain:
Yeah, so I think for me, like I said, I had friends who were in Tulsa Remote. And so then just doing things together. So there was also Blueprint 918. I can't remember, but there was like a black professionals group. And I found out about that from someone who was in Tulsa Remote. There were others who were doing the black towns tour. So just doing things that were member led allowed me to meet people who were outside of Tulsa Remote. And then I got involved with my sorority. So that was huge. And then I learned about Leadership Tulsa. And Tulsa is small enough where if you know at least two or three people, you know everyone. And so for me, it was just important for me to find out, like, I like to work out. So I joined a gym that was, you know, not in downtown. So it was important for me to make sure that I find things that weren't so close to Tulsa Remote or downtown so that I can at least expand and learn. But that was just kind of how I found my people through Tulsa Remote, ideally, you know, initially, and then just expanded.

Justin Harlan:
But it also, I mean, I think it's such a great example of you coming in, first of all, with intention. You had reasons that you were relocating, but then you also made really great effort to find the spots that you knew you would connect with others. And leverage those resources and aspects of your identity to bring those connections together. And I think it's such a great model of like, sure, you leverage Tulsa Remote in some ways, but you also really took the initiative yourself to get out there and find a way to call this place home, which I think is really powerful. And then now you've stayed beyond your year. And I know that in the process there, you also started your own business and kind of took that leap of faith, betting on yourself. Talk me through that decision.

Montana Cain:
Oh my gosh. That decision was a tough one, I will say. And I think prior to me even having my own business, I always kind of had side projects. Like I always had side projects, but I always called it a hustle, right? Like I never saw myself as an entrepreneur. And I think that word, I only associate with people like Damon John or those who you see on Shark Tank. So I never saw myself as an entrepreneur, right? I saw myself as a hustler. Like I have a full-time job and I have one or two projects on the side. And so being in Tulsa, right, home of Black Wall Street, where we had a community where we were self-reliant, and then being at Camp 2 really helped me to be among other entrepreneurs. Like, oh, this is regular. This is the person I was at Trader Joe's with. Or this is, you know, we just got pedicures and she's an entrepreneur. So for me, it was able to see that title on regular people. So it was just nice to see regular people doing big things.

Montana Cain:
And at the time, I was really wrestling with that decision of do I go off and do my own thing? I was in a job where I was really unhappy and I'm someone who plays it safe. And so I was like, OK, you're going to take a career break. Like, we're not going to call it your leap. We're just going to call it career break. And I did that in the midst of doing New You, which is something that I found out about, you know, from Tara connected me to Aaron. So again, like that Tulsa Remote, which is kind of being the base and then plug. And so doing New You, I was among others who were part of Tulsa Remote and not, who were also making shifts in their life. And so that helped me, had a community of people who were also making changes. And so in the midst of that program, I quit my job. And said, okay, you're going to give yourself three months to try this solopreneur, you know, self-employed life.

Montana Cain:
And I did it. But I also had resources here. So I think that's the other thing. Like I was also, after New You, I did EIR through Build in Tulsa. So they have an entrepreneurs in residence program. So I was sitting with other entrepreneurs where we're struggling through the same thing of like, because sometimes you think everyone has it all together. And you think you have to have it all together before. So it was just nice, again, to see regular people who had the title of entrepreneur who were also figuring things out, which gave me the permission to say yes, while still not having all the answers in place.

Justin Harlan:
Yeah. So, I mean, in a lot of ways, you have uprooted every aspect of your life in your move to Tulsa.

Montana Cain:
And I'm tired now. We're in eclipse, aren't we? I'm tired.

Justin Harlan:
But in others, I mean, there's so much power in the representation that you're describing where you were able to come in with clear eyes and see other people that maybe you didn't see yourself in that position. And then you see other people that you look up to or even think, oh, that person is just like me. They're kicking butt at this. And then you also kind of mentioned some of those resources and programs that you plugged into. I know you've only been here a short time. But like, what is it about Tulsa that you think kind of brings these things out? Whether that's connection or the resources or the programs, how has Tulsa created that for you?

Montana Cain:
Yeah, I think access, right? I think knowing that these things are here and that that fits me, right? I think, and like I said, being at Camp 2, I was able to see Build in Tulsa. And so able to hear from Ashley and Desiree about their programs that they have to offer. So I think for me, it's the proximity in terms of location, because it's a small enough city where you can, everything's within reach. But then I also think it's just a really nice community, right? Like I moved from New York, but we don't say hi to people. And in South Carolina, they wave. And I feel like here they ask you how you're doing and they want an answer. And that's been in everyone I've met. And I have a friend who came to visit as well. And she's an entrepreneur as well. And she noticed the difference here is that people are more collaborative. So I think anywhere else, I don't know that would have had a community… like we're not competing. Like I will share my resources with you. You'll share with me. And so I think that for me has been the community in Tulsa, whether I'm talking about my business or anything else, where just people are willing to help each other. And so I think that's what makes it unique. And then, of course, the resources that are here intentionally to build back, you know, Black Wall Street in particular about supporting other business owners.

Justin Harlan:
I love it. So what advice would you have for folks that are maybe considering moving to Tulsa through Tulsa Remote?

Montana Cain:
Do it. Honestly, because you won't. I think it's a place where you can make your own adventure. So my thing is, what's the worst thing that could happen? If you don't like it, you move back or you move someplace else. But you have to give it a try because if you had asked me If I would ever be in Oklahoma, I would have said no. But I took the chance and I was just like, and I remember even driving in my car of like, because everything happened so fast. Like I said, December got the job. March, I moved here and I remember in my car, like you just packed up all your stuff and sold your house and you were driving where? You know, I remember thinking like you are doing this. And I think sometimes you just have to take that leap of faith. And again, the worst thing that could happen is you don't like it. So I just say do it.

Justin Harlan:
It's so interesting to hear your story because there's almost like a shift in your mentality where early on it was like almost like, why should I say yes to this? Where now it's like you're just saying yes to everything.

Montana Cain:
Yeah, because I mean, so many things have worked out for me since saying yes. You know, I met my partner while I'm here, like while I've been here and I said yes to the job. I now have like a group of close friends because as a grown woman, as an adult woman, sometimes it's hard to find friends. But I have a friend group where I can call them and say, hey, let's go grab drinks. Let's go to Target, you know, our favorite place. And, you know, it's just nice to have a community of people here where you can do different activities. And so, yeah, it surprised me and kind of pushed me out of my shell because I didn't have family here. And so I wasn't able to rely on my same crutches. So it's a place where you learn to swim, right? Like I could have sank if I wanted to, but I was like, no, I'm here. I'm going to swim. And I can't swim in real life. So that's not the best metaphor, but you know what I mean.

Justin Harlan:
You're like the living, breathing example of that Jim Carrey movie where he has to say yes to everything. And it's like this curse that he has. And you are it. You're saying yes and you're thriving. And it's awesome to see. I mean, you're contributing in so many ways to the community. I also would love to ask you, like, what advice would you have to local Tulsans? Because it sounds like there's this really cool part of your story that is, like, people that have been here for a while grabbing you and saying, like, come to this thing or, you know, let me introduce you to this person. What advice would you have to local Tulsans that they think about, maybe not just Tulsa Remoters, but like any new people that are coming here wanting to be a part of what's happening, that special sauce that we can kind of all feel and breathe. What advice would you have to them?

Montana Cain:
Ooh, Justin, that's a really tough question. And I'm going to be really honest with you. I think that's a hard question for me to answer because I feel like I can learn more from them about kind of their perceptions of us. But I think, because I can't speak for all of Tulsa Remoters, I can speak for myself. And I know for me, I am aware of kind of the privilege that I have as being a Tulsa Remoter and kind of how I have access to things. But I make sure that I leverage my relationships. So for me, I have friends who are local Tulsans and they don't know about some of the resources. So for me, those who are in my network who are not a part of Tulsa Remote, I bring them along the journey. Like, hey, we're going to go work at Camp 2 today. And so I'm like, hey, they have female founders pitch night. You better apply. So for me, those who are in my network who are not a part of Tulsa Remote or the ecosystem, I bring them along of like, hey, here are these resources. So I feel like and especially, you know, being a black woman here, I know that my, you know, I'm not a native black Tulsan and so I can't speak for their experiences. So I think I would be careful about what I would say to them other than like just being open to hear their stories and then sharing my own.

Justin Harlan:
Sure. Makes sense. And it sounds like you have a desire to also ensure that the same access that you receive through being in the program is also given to others. And that information is powerful. And even just having that as a baseline is important to you for the folks that are, you know, in the circles and beyond.

Montana Cain:
Absolutely. Because I know that it's a very, I'm still learning a lot about Tulsa. And so, you know, I am, so you hear both sides where people are loving Tulsa Remote and people who are like, you know, really skeptical. And I want to know more about their whys on both sides. And so that's why I'm just like, I just want to listen and take it in because I'm still, you know, even though this is home for me, I'm, there's still a lot for me to learn about here. And yeah.

Justin Harlan:
We're glad you're here.

Montana Cain:
Yeah, I'm glad I'm here too.

Justin Harlan:
I'm grateful that you gave us some time today. Thank you for talking and yeah, thanks for all that you're doing for the community.

Montana Cain:
Yeah, well, thank you all. This is a great opportunity, so I appreciate it.