My name is Sean “Wailin” O’Phelan: 

I am a 20-year Big Island, Hawaii resident with a long history of community building and problem-solving through my entrepreneurial ventures. I'm a musician (Harmonica Sean), event organizer, and handyman with clients across the island.

 

In 2025, I bought a truck and quickly realized that the lack of reliable transportation on the Big Island affects the entire 'ohana (family) in many ways. With my broad experience, determination, and a “get it done” attitude, I founded Cruise With Me Rideshare. We currently offer the community a comfortable, safe, honest, reliable, and affordable solution to transportation challenges. My goal is to expand Cruise With Me across the islands and provide cost-effective options for everyone!

​

My team is my ‘ohana. My drivers have shown me that when you lead with care for people and invest in growing from within, you can build a business that strengthens the whole community — one that gives hardworking local families real opportunities to make ends meet and get where they need to go.

​

I'm always open to feedback, and I'm driven to keep doing this right. So "come cruise with me, Hawaii" — follow along, and help spread the word as the journey unfolds.