What inspired you to become a hairstylist?

I went to a summer camp as a child from the time I was 8-17. The year I was a counselor in training, there was a counselor who I looked up to a lot. He was From Spanish Harlem and his name was Dakibu. He would give himself and a few others haircuts over that summer. It was the nineties and the cut of that time and now, the fade. By the end of the summer, he agreed to show me how to cut my own hair. I went home and couldn't wait to try it out with the clippers I had insisted my Mom buy for me. I went into the bathroom and 40 minutes later came out with no hair at all. I did eventually get the hang of it and would continue to cut my own hair and anyone else's who'd let me. A couple years later, 1993, I was at college in Washington state at The Evergreen State College. I was getting my haircut at a place called Rudy's in Seattle when I was in the city. It was this funky walk-in unisex shop with tattooing out back. At the time Portland only had higher end salons or old fashion barber shops. I immediately knew that's the kind of shop I'd like to have one day if college didn't pan out. And. It didn't. Thanks, Doc. Thanks, Rudy.

At what point did you realize your passion would become a career path?

My passion in life isn't my career. It's how I live day to day. My career, which I love, allows me the freedom to do what I want with my time. Being creative and interacting with people are the two things I love most about my job, but I need change and plans and activities to make me happy. I'm definitely a seasonal person. Snowboard in the winter, beach and lakeside chillaxing/camping in the summer, cycling and walking/hiking during the spring and fall. Traveling at least a couple times a year. The flexibility that I've created with my work schedule allows me the time for these activities. And that's where I find my passion.

You have been a resident Dj in Portland for over a decade, can you talk about your experiences as a DJ, some of your favorite gigs, how you first got involved in the scene and how music has affected your life?

I’ve been a resident DJ at Flask Lounge for 7 years. Previously I hosted a night at the White Heart in Portland for a couple years as well.

I’ve been in love with music since I was a child and have experienced many of the music scenes around Portland since the 80’s. At first, it was break dancing on the corner in front of the 7 Eleven. Later as a teen discovering Zootz and The Warehouse. Two different clubs that Chris Clark owned in the 80’s and 90’s. 1991 was the year I attended my first Rave and from that point, it was on. Many parties up and down the east coast with some out west. Then I discovered the NYC nightclub scene in my mid 20’s while dating Jack MF. Getting schooled in the classics and house culture.

Music has meant SO much to me over the years. It gives me guidance, inspiration, hope and so much joy! I love dancing more than most things in my life. Moving through time and space to sounds makes me feel connected to the universe and divinity itself. I DJ as a passion and hobby. The love of music and DJ culture has taken me all over this country and created a community that spans the globe. I’ll continue to seek out new experiences through my love of music. As long as I live.

Listen to Jaime O'Sullivan On Mixcloud

What are one challenge and one lesson you’ve learned from your experiences of entrepreneurship?

Extra money doesn't exist. There is an ebb and flow to my business. It comes seasonally and over time. I've learned to not go crazy with spending money when there seems to be an abundance, but then again, I've never been someone to save. So mostly I try and put back into the business to keep it fresh.

What do you do outside of work that directly impacts your career?

I've always been a social person. When I'm friendly and talk up my business, I can draw new clients in. How I interact with people outside of work directly affects my business.

Do you have a favorite haircut memory?

I've been told many times, "that's the best haircut I think I've ever had!" Or, "People have been telling me that this is the best cut I've ever had!" Those are the Best Compliments I could ever ask for!