Derek Okahashi: Aloha Ambassador

Derek Okahashi has found his calling. All the qualities that he believed were personal flaws of his and had been criticized for – being obsessive, disruptive, curious, “the kid who was incredibly smart, but couldn’t shut up and listen,” or “the worker or Coastie with potential, but was insubordinate and wouldn’t take orders” – turned out to be incredibly valuable when starting his real estate business. 
In just the last four years, Derek has started his business, hit top producer status, established Core Team Hawaii, and created a culture with his team members and clients that is helping to disrupt the industry and people’s perceptions of real estate agents.
“Our clients say we are refreshingly authentic, that they don’t feel like they are dealing with a salesperson,” Derek said. “I think that’s what makes us unique – we are unapologetically us: local, Hawaiian, not-Hawaiian, super experienced, inexperienced and learning, nuanced, ambassadors of aloha.”
Derek has always marched to the beat of his own drum. Born in Pensacola, Florida, he started visiting his father in Hawaii at the age of 10, spending summers having fun and working with his stepmom, who was a nurse. At the age of 12, he called his mom in Florida and told her he was not coming home. He traded all-star travel baseball for a surfboard and never looked back. 
Surfing and beach culture became an obsession for Derek. He read books about the golden era of the beachboys in the early 1900s and studied surf culture of the 50s and 60s (his dad’s era) and wanted to be a beach boy. 
“I was going to make boards or do something that kept me in that world,” he said. “My dad hated it. He left Hawaii because he was essentially homeless and living on Waikiki beach working as a beachboy to get by.”
Derek always looked up to his father and wanted to be like him or make him proud. 
His stepmom had a big impact on him as well, having introduced him to a different kind of lifestyle and influenced him to enter the healthcare industry later in life. He also credits his mother, who passed away in 2013, for instilling in him her sense of compassion. 
Seeking more positive influences and structure in his early 20s, Derek decided to join the Coast Guard in 2006. “In the Coast Guard, I found a ton of difficulty and what not to do, but it elevated my growth mindset and I essentially got paid to grow up. I also found leaders to model,” he said.
Another person Derek found to model was his wife, Michele, whom he married in 2007. “I was lucky to have met someone like my wife who showed me the pursuit of goals and education,” Derek said. “I couldn’t understand how she could work so hard pursuing her dreams, because I hadn’t defined any for myself. Michele had, and she even took 24 credits in one semester to play catch up because the Coast Guard delayed her schooling.”
Derek served six years of active duty in the Coast Guard as a Marine Science Technician, doing foreign vessel inspections. During that time, he also started a Brazilian Jiu-Jitsu lifestyle brand that he eventually sold to his #1 competitor after graduating from x-ray school to pursue a career in health care. With the sale of his business and the birth of his second son at the same time, Derek became obsessed with finances and growing savings for his family’s future. He listened to hundreds of podcasts about real estate and studied books like Rich Dad Poor Dad while commuting over an hour each way to Stanford, where he worked as an x-ray technician with world-renowned physicians, residents, and fellows at Lucile Packard Children’s Hospital. 
“I was the guy that people would bounce investment ideas off and I even became knowledgeable in life insurance products because a coworker was selling them. In the year leading up to moving back to Hawaii– because I was always going to come home to raise my family – I remember a coworker in the x-ray department saying ‘Why don’t you become a REALTOR® or sell life insurance or something? That’s all you talk about.’ I told her that I was going to when I moved home.”
Derek moved back home to Hawaii in 2019 with Michele and their two kids, Duke and Dane. Within a week or two of getting off the plane, he started his real estate licensing class. He also lined up a job at Queens Medical Center, where he turned down a management position and even asked to be demoted to be on-call so that he would have enough time to pursue real estate. After fumbling around for a year and depleting his savings, however, he decided to get serious about real estate.
With his full focus and obsession centered on building his business, Derek found quick success. He first started to form Core Team Hawaii after getting connected with Mahe Kahale, who is the team’s main agent today, along with agents Kenji Lee and Aiden Martin, and Michele, who runs the back office.
“I wouldn’t be here without Mahe. She is a rock – committed, coachable, and consistent. She has a rare mix of being obsessive and coachable that you don’t find every day,” said Derek. 
Derek recently moved his team to eXp Realty, where he plans to build and grow partners around the world. He is currently passionate about coaching and mentoring, “creating more opportunities, a greater mindset, a wiser approach and more abundance” for his team members and extended team.
“I want to make sure my team members have a better life and are more prosperous while having the ability to be better parents and better versions of themselves. As a team, we will play our small part in making real estate more skilled and authentic. We know that what we have is special, so we will protect it while also mentoring and building other individuals and teams at varying proximity,” Derek said. 
While all of Derek’s time these days goes either to his team or his family, his hobbies, in theory, include surfing, jiu-jitsu and basketball. Evenings and weekends are devoted to his kids’ sports. Duke is a basketball player with a knack for engineering and solving problems. Dane loves football and can’t get enough of Zippy’s chili.
“My family is the most important thing in my life,” Derek said. “I wouldn’t be here without them or the support of my team. And I wouldn’t want to achieve the heights we are aiming for without them. We have more to go, more people to bring along with us, and more Aloha to spread.