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What Maui taught a tech entrepreneur about family, loyalty, and leadership

What Maui taught a tech entrepreneur about family, loyalty, and leadership
Rowers take off from the island of Maui Photo courtesy of Go Hawaii
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How a stint in a tropical paradise changed an IT expert’s life forever.

It was love, the early internet and a particularly harsh winter that led Frank Bradshaw to Maui.

Today, he’s the founder and CEO of Ho’ike Technologies, an information security firm whose name borrows a Hawaiian term meaning ‘to guide,’ an homage to the generous spirit of Hawaiian culture. But in 1994, he was just a recent grad trying to figure out what life after college looked like.

While at the University of New Mexico, Bradshaw had become interested in computers and networks after sustaining a football injury. “I had all this idle time, and I began to read up on new technologies,” he recalls. His curiosity led him to the student computer lab, where he got hands-on experience, leading to a few contract jobs. Upon graduation, he agreed to help a friend with a project, and in doing so relocated to Minnesota.

While in Minnesota, Bradshaw spent some of his downtime in a chatroom facilitated by a supercomputer at Rutgers University, where he met his now wife, Kate Twelker. “This was before people met people online,” Bradshaw said. He explained that this time was well before the era of AOL Instant Messenger, Yahoo Messenger or anything comparable. A handful of entrepreneurial computer science students at Rutgers had set up a MUD, or multi-user dimension, which allowed people from all over the world to login as text characters and chat.

That MUD is where Bradshaw began chatting with Twelker, then a New York University student befuddled by her new laptop and directed to the MUD by an employee of the school’s computer center. That person assured her that it was full of “a whole bunch of nerdy folks,” and that they could probably answer any questions about her new machine.

Bradshaw happened to be online when she logged in and after he answered her computer and technology questions, the conversation then turned to music. Both liked house music and, as it turned out, they both had friends who were co-partners in running a house club in New York City. They began talking frequently, with Bradshaw making trips to New York City to visit her. Upon graduation, Twelker was burnt-out and tired of New York, which was on the precipice of an especially harsh winter. Ready for a clean break, she was craving something more like home — and for her, this happened to be Hawaii. “I’m in Minnesota, it’s cold and I get a chance to go to Hawaii,” Bradshaw said. It was a no-brainer: “I’m going to Hawaii.”

The coastline off of Maui
The coastline off of Maui Photo courtesy of Go Hawaii

Upon arriving, Bradshaw was quickly introduced to the concept of ohana, a term for family that is inclusive not only of blood relatives but also those who are adopted or intentionally integrated into the family. ”[In] this concept of ohana, you make people a part of your family,” he said. “From the moment I got on the island, my mother-in-law introduced me to her friends, [and] those friends all invite you in and make you part of their family. That is very much the culture of the place: As soon as you arrive, it’s almost like [it’s] everybody’s duty to make sure that you relax and become part of the group.” Through word-of-mouth and personal referrals, he was able to find work on the island, growing his skill set and his reputation in the process.

“When you live on an island, networking is key,” says Hawaiian native Archie Kalepa, a rescue swimmer and accomplished waterman. Due to the small population and subsequently small social scene on the island, there is an increased expectation for integrity. “Word gets around very quickly if you don’t do things right or you have the wrong values toward business,” Kalepa said. “When you live on an island, you’ve got to make sure you’re conscious about [doing] the right thing. The core values of being a good person [equate] to having a good business — not only for profit but maybe for the environment, maybe for the betterment of mankind. Those kinds of things are important to the people of Hawaii when you think about business.”

This awareness of interpersonal behavior is fostered by an awareness of nature innate to Hawaiian life. “When you live on an island, you’re more aware of what’s happening around you, because everything that we do on an island is dictated by weather,” Kalepa said. “You develop a sense or an awareness for your surroundings. Everything is so compounded that you’re really aware of what’s going on around you, and I think that’s the beauty of living in Hawaii.”

Views from the beaches of Maui
Views from the beaches of Maui Photo courtesy of Go Hawaii

The essence of connectedness — echoing from nature to people — wasn’t lost on Bradshaw. The welcoming spirit and attitude of generosity he felt from the people of Maui made an impact on him immediately, personally and professionally, and led Bradshaw to found Ho’ike Technologies with the spirit of ohana in mind. “I make my clients part of the family,” he said. “Ho’ike means to guide. I adopted that name because so many times you get a consultant to come in and they just run through [the job] and say, ‘Here, I did it.’ I don’t simply do the job for them, I help them understand what we did. That may seem like it takes a little bit longer, but you understand the process.”

“When we talk about managed services, you’ll see this phrase: ‘MSSP,’ [or] managed security service provider,” Bradshaw said. “I take a different approach: I’m not your ‘provider,’ I’m not going to give you something and then walk away — I’m your partner. I’m in this with you. Where you go, we go. If you fail, we fail. If you succeed, then we helped you succeed.”