When Drew talks about Tulsa, it’s clear his move was more than a single choice it was a combination of love, community, and opportunity. Drawn first by a personal connection, he quickly discovered the city offered so much more: live music, entrepreneurial energy, and a welcoming community that made staying easy.
In this extended Q&A, Drew shares his journey, what surprised him about Tulsa, and how he’s built both a career and a life here as a Tulsa Remote member.
Watch Drew’s interview on Instagram
My name is Drew. I tell people it’s like “pinches.” I came to Tulsa for love. I met my now partner at a Creative Economy Summit a couple years ago. We basically did long-distance high school dating for a while, lots of phone calls and lots of travel. Indianapolis is 650 miles away, so the commute wasn’t ideal.
When I came here for that summit, I was impressed. We went to Cain’s, I caught a show at The Colony, and I saw King Cabbage Brass Band play an unreal Rage Against the Machine cover. That was a moment where I thought, “Oh, there’s something cool happening here.”
I grew up in Indianapolis and near Chicago, and I’ve always loved mid-sized Midwestern cities. I hate the flyover country narrative. I always ask people, “Well, what did you try to do while you were here?” Live music is one of my favorite ways to get to know a place. You meet people who are truly invested in their community. And the next morning, you find them at the local coffee shops.
If they give me free swag, absolutely.
I actually heard about it at that same Creative Economy Summit. Someone mentioned this incentive program that brings people here, and I thought it was interesting, especially the retention rate. That tells me people aren’t just coming for cheap rent or an easy airport. They’re staying because they’re finding a life here.
I didn’t have a negative view of Oklahoma before arriving, though I did finally watch Twister three weeks ago, so that had been my main reference point. But I think a lot of people feel that way about Midwestern places. Not negative, just blank. And once you actually explore it, you realize it’s all about the people.
Give it a shot. You’ll be pleasantly surprised.
I didn’t understand “Green Country” until I moved here. It’s beautiful, hilly, and lush. The summers are hot, but not depressing. You can still get outside.
And in a city this size, the barriers to entry are low. If you’re interested in something, whether that’s an art installation, a nonprofit, or a local project, it’s easy to get connected. People here genuinely want to bring you in. It’s inclusive rather than exclusive, and that matters.
I was running my own small business consulting company. I’m a project management dork. Most entrepreneurs don’t start businesses because they love inbox management. They love the product or service, but not the day-to-day structure.
I teach consistency over intensity. Build simple, daily habits and stick to them. That’s what keeps people from burning out. That’s my passion—helping people keep loving the thing they built.
I still do some consulting on the side, but moving here gave me the chance to blend my entrepreneurial skills with local community involvement. I also run One Million Cups Tulsa, a monthly entrepreneurial meetup through the Kauffman Foundation, which has been a fun way to connect and share experiences.
I’m not bored, that’s for sure.
I now work with Tulsa Innovation Labs as a Manager of Innovation Initiatives. We’re building out the autonomous systems industry in Tulsa and mapping the technical skills needed to grow that workforce. It blends economic development and entrepreneurship, and it’s exciting to be part of something growing from the ground up.
Through spaces that aren’t just home or work. Coffee shops are a huge community hub for me. Coffee is my only vice. I’m vegan and very sober, so I spend a lot of time in these spaces. I like asking people what they’re drinking rather than “How are you?” Those conversations open people up.
I’ve also met tons of Tulsa Remote members and alumni. If you ask fifteen people why they moved, you’ll get fifteen different answers, and I love that. It means the appeal is wide.
I also love that people here celebrate risk-taking. When someone quits their job to pursue something entrepreneurial, the response is “That’s awesome,” not “But what about your benefits?” That support system matters.
How beautiful it is. I didn’t expect it to be dumpy. I just didn’t have a picture in my mind.
My first visit was cold, rainy, and 43 degrees for three straight days. But when I came back, and especially once it warmed up, I was struck by how pretty the river is, how nice Riverside and Gathering Place are, and how easy it is to run or bike from downtown.
I’m also impressed by how much live music is available in small, intimate spaces. Big arenas stress me out. Seeing Unknown Mortal Orchestra at Guthrie Green for free, two blocks from my place, was incredible.
And there’s a genuine pride in Tulsa’s musical legacy that I didn’t know about before moving here. It’s emotional pride, not just historical pride.
Sound Pony, absolutely. I like spots with character, not pristine venues that feel like hotel ballrooms. I want a little grit and history in the walls.
Guthrie Green is another favorite. You can get close to the stage, there’s tons of space, and we can bring our dogs, which is great.
I need to dive deeper into the jazz scene. That’s next on my list. I’m a jazz nerd, and smaller shows are the best way to experience the subtlety of the music. As a drummer, I’m not listening to drums first. I’m listening to everything. Jazz really rewards that.