How 4 Savvy Locals Who Weren’t Born Into Money Manage Their Finances in Hawai‘i

How they’ve made it, saved it and are passing it on.
Photo: Aaron K. Yoshino



It’s an eternal question, one expounded upon—after making allowances for local language differences—by sages from Aesop to Confucius to Warren Buffett. What makes one person a money honey hive and another a financial sinkhole is an issue of special relevance in Hawai‘i these days.


This isn’t an abstract question for us at HONOLULU, because we live here, too. And so we asked about, then interviewed, a cross-section of akamai folks who seem to have found a path. Read on for their journeys—and their tips (because, let’s face it, we’re all about the tips).


Oh, and one more thing.


Although they certainly have assets, own or have owned homes and exude prosperity, none of our subjects are “crazy rich” in the current pop sense. What they have is a mindset that is itself a form of wealth. In our opinion, that makes them among the “really” rich—not least because they can live in our beloved Hawai‘i nei.


SEE ALSO: #LuckyWeLiveHonolulu: 33 Money-Saving Tips, Life Hacks and Savvy Shopper Steals 


“Growing up, money was a big secret. No strategy whatever in the family. It’s really a shame. We’ve got to make sure our son, when he gets older, makes sure to plan, especially if he’s planning on staying in Hawai‘i.”—Keoni Vaughn




What Keoni Vaughn remembers about his Waimānalo childhood is the elephant. “My grandfather worked for the state as a Section 8 housing inspector, but he always had his hand in different things: politics, business. He leased an elephant and rented it out. It was the mascot for Pepsi. Can you imagine?”


Vaughn, 46, also recalls snorkeling around in the fishpond at the swank John Dominis restaurant while that grandfather, Bill Young, a part-owner, joined the staff for lunch. “He wasn’t your typical guy who does his 9 to 5 and then goes home.”


Vaughn’s grandparents helped raise him while his parents worked long hours at Amfac and Empire Tours. What he doesn’t remember from this time is any discussion of finances, or life strategies, at home. Today he knows he paid a price for it. “I’ve been working since I was 15. Through high school I gave my family my paycheck to help out. They gave me a stipend. When I went to college, I was kind of left to figure it out on my own. I was paying my own way and had a hard time keeping up with the payments. I stopped after six months.”


He has felt the lack of a college degree his whole life. “I always started at the bottom of the ladder.” A tour driver, he applied five years in a row to be a manager. “This was at a major tour company and they said, ‘You’ll never be a manager.’” He would rise to assistant director of operations.


But disaster struck in 2001. “I had a 401(k) and then after 9/11 the stock market crashed and I watched the money I put in there disappear. I freaked out. I had no financial education, so all my buddies and I cashed out. We paid the penalty, like 40 percent, and the next thing you know we blew it all. I had no retirement left.”


He’d also lost his job in the economic downturn. By 2003, he’d gone from assistant director of operations to picking up stray cats for the Hawaiian Humane Society. “It was a very humbling experience. Very. But I found a mentor—Pamela Burns,” the late, and beloved, leader of the Humane Society. As he worked his way back up the ladder, he says, “I knew I had to plan to have something to retire on. So I enrolled in a 403(b), a plan for nonprofit employees. Every time I got a raise I would increase my contribution instead of spending that money.”


He was back on his feet, on the rise to vice president, when his family blew up into full conflict after his 104-year-old great-grandmother died. But by then he’d married a woman whose family’s radically transparent approach to finances showed how he could grow his money, while sorting out the mess left by generations of secrecy.


SEE ALSO: Thrifty Rich Locals: The Best Money Advice for Each Decade of Your Life


“Our adoptive parents did not want us to be orphaned again by their death. They made sure we were exposed to all walks of life, that we were well-traveled and we would learn to manage money.”—Jacque Vaughn


As a child born in war-torn Vietnam, Jacque Vaughn has gone from orphanage to poster child for success, American-style. She’s worked hard for it, but also inherited a scrimp-and-save mentality, she says, from the white U.S. military couple who adopted her. “They lived frugally. When we went out to eat, like at a McDonald’s, we weren’t allowed a beverage. We didn’t have designer anything.”


But her parents did design their lives. “Coming from small towns,” Jacque says, “they entered the military life and that opened their eyes.” They gave Jacque and her brother, an adoptee from Germany, education and experiences instead of things—and, from an early age, required them to give back in the form of service.


Jacquelyn and Stephen Smith also opened the family books to them when they were small: “We call it the Full Monty approach,” Jacque says. Early on, they talked about what would happen when they died. “Our adoptive parents did not want us to be orphaned again by their death.”


From Jacque’s adoption on—the Smiths had to fight to receive a presidential authorization to take her from Vietnam—they set an example. “When they first adopted me, my parents planned to live in Virginia near family,” she says. “But they decided not to, because being transracial would be a handicap for me. They moved to Hawai‘i in 1975.” But that raised a new concern: “One, the cost of living, and two, what the future would bring. So they made sure we were exposed to all walks of life, that we were well-traveled and we would learn to manage money.”


A Navy commander, her father walked her through her first salary negotiation for a post-college job, in public relations. “We sat down. I said, ‘There’s no way I can make a living in this field at this salary,’ so we crunched the numbers. What I needed to pay the rent, to pay car insurance. And the only way to break even and maybe go out to a movie, he said, was you gross $24,000 a year.”


Now, he added, Jacque was to take in her calculations and show it to her interviewers. “He said to ask them to come as close as they could.” She laughs. “You have to be very respectful and polite when you’re laying that on the table.”


She got the job at the number she wanted, when others at her level were making $18,000 to $20,000 a year. Her father then marched her into a bank to set up an IRA. “He said, ‘I want you to put a percentage of your income away. And when you get a raise, put more away, maybe 5 percent.’”


She followed through. And yet, in her 20s, she went through a rebellious phase. “You look at other kids wearing all the clothes you wanted, you’re in that shallow and sensitive stage,” she recalls. “I ran up credit card debt, bounced checks, as many do in that time period. So many of my peers got caught upholding the mythology of how it should be: the designer bags, the designer clothes, the expensive cars which tend to depreciate so much. It was a real struggle.”


“In New York, I stayed with friends who all had Broadway backgrounds, but they all had regular jobs. I said, ‘Guys, don’t you want to go audition?, But they’d given up their dreams.”—Cyndi Mayo




Socking away micro-percentages, keeping to a spreadsheet budget—frankly, it all can sound rather joyless.


And yet you can have your dreams and your savings and growth strategy, too.


When Cyndi Mayo was born in Oakland, California, her parents were living with relatives and trying to decide if they could afford to move back to Hawai‘i. “Dad is Hawaiian-Caucasian, Mom’s Filipino-Spanish-Chinese,” says Mayo, whose hyphens include singer-dancer-actress—and investor. “All told, 11 ethnicities.”


She grew up on O‘ahu and then Maui when her father, who had a car-detailing business, decided to get away from traffic. There, the family formed a band. “Since I was 10, we’ve had a group called Family Ties. We all took hula, Tahitian dance. I sang pretty much in Hawaiian.”


Often, work brought the family band to Waikīkī. “Since I was a young age I’ve been in shows,” she says. To tide them over the lulls, her father had a side business. “He’d have vending machines, so we’d go around town filling them.”


His industriousness rubbed off as Mayo hit adulthood. “I just decided to go to college, get a business degree and put the entertainment thing on the side.” At the University of Hawai‘i at Mānoa she earned a degree in travel industry management. Her course seemed set.


But college had whetted, not dampened, her passion for dance. “I was in a group, Maile Aloha Singers, that took us around the world.” A visit home after graduation led to a job at a show as a singer-dancer on Maui, allowing her to pursue her art while keeping other revenue streams flowing.


She’s traveled the world and risen to new challenges. “I was a magician’s assistant once, because it paid more. I didn’t get sawn in half.” She was hired by Legends in Concert to play Janet Jackson in Waikīkī. There’s been acting, commercials, movies; a long gig with the ‘Ulalena show on Maui paid her $50,000 a year, much of which she banked by staying with friends.


She knew just what to do with the money. “Because I came from pretty humble beginnings, over time I saved. A friend helped me open a 401(k) in my early 20s. From just talking to people, I got into investing, seeing what I could do.” When she saw a professional opportunity, she invested in that, too, by flying to auditions in Las Vegas and New York City.


The payoff from sticking to her passion came when she was called to New York in the 1990s to audition for her dream job—Dreamgirls. “I stayed with friends who all had Broadway backgrounds, but they all had regular jobs. I said, ‘Guys, don’t you want to go audition?’ But they’d given up their dreams.”


Mayo was hired to tour and then the original dream girl, Jennifer Holliday, decided to join them. Performing in front of tens of thousands of people, she played nearly every role—even that of a blonde with a top hat and cane. “I lived with another cast member and saved enough money to buy a one-bedroom condo in Hawai‘i and was able to sell that in two years and use the profit for my next townhouse, which was a three-bedroom, two-and-a-half-bath. Now I’m renting again, but I want to own again.”


Never forgetting her father’s example, for the past seven years Mayo has also balanced her creative schedule with a “real” job as a flight attendant for Hawaiian Airlines. “I could’ve gone into management somewhere, but flying is more fun, more flexible.” And she can keep dancing and singing.


So, yes, you can still keep your dreams.


“Doing multimedia was my dream job—even though people said, ‘You’ll never make anything.’ But there are people out there who will help people become homeowners.”—Ellen


Studies show that wages grow fastest in your first 10 years of work. However, not everyone gets the memo about growing an asset base. For many in their 30s, one day they look around and realize life is a race—and they’ve missed the starting gun.


For others, it’s a job with a low salary limit that puts a crimp on any hopes of surviving in Hawai‘i, let alone buying a home. “Finance was discussed” growing up, says Ellen (who asked that her last name not be used). But she chose to be a multimedia specialist anyway—No. 28 on USA Today’s list of lowest-paying professions. After a few years working her way up from entry-level positions in a small metro area on the Mainland, she was making $29,000 a year.


Then her company was sold and she decided to move to Hawai‘i to join her grandparents and parents. It was only a couple of years after the 2009 crash. “My timing was terrible,” she says. “I was so stupid.” Plus, instead of staying with her grandparents, “I paid rent!” After seven months, her savings almost out, she finally found a job.


After a few years of living with four roommates and paying $730 a month in rent, Ellen decided to buy her own place. But to obtain even a $250,000 mortgage in a state where the average condo costs $410,000, she calculated it would take at least 10 years of saving—and by then the price could be 30 percent higher, or even more.


Ellen met with a real estate agent who specializes in putting people into their first home. “She got me to the Hawai‘i HomeOwnership Center,” a nonprofit that helps local lower-income working people to become homeowners.


“They educate you on the homebuying process,” Ellen says. “They have classes, one-on-one counseling.” With HHOC’s help, she created a monthly budget and stuck to it. As her savings grew, she enrolled in the nonprofit’s down-payment assistance program. “If you live in the state of Hawai‘i, are buying for the first time, and your income is within a certain range, you can get up to $40,000 to use toward a down payment. With zero interest,” she adds.


She smiles. “I was so surprised by this, I emailed everybody.”


Her income fit into the range—it can’t be too high or too low—and she set about gathering documents, including credit reports, W2s and tax returns for the past three years, pay stubs, checking and bank statements. But since she only qualified for the lowest-priced unit in a still-unbuilt affordable housing development, the competition was stiff.


She didn’t get a place—but she didn’t touch her savings, either. After an initial deposit, a second was due after 30 days. But before that happened, she got a phone call: Somebody had dropped out of a condo deal. She had 24 hours to accept, commit and make her down payment on a place that wouldn’t be finished for another three years, and that she wouldn’t be able to sell, or rent, or move from, for five more years.


“I said yes.”


It’s now almost three years later and Ellen has just gotten word that the deal has closed and the condo is hers. During those three years, she says, “Some of my friends have had to leave Hawai‘i. A couple of them made double of what I did. So I’d just say to you, ‘Wait—you don’t have to go live in Florida.’”


“There’s so much you can’t control. You can’t control if you get a raise, or if you can find a better job. To acquire real estate and know it’s going to appreciate is exciting.”—Jacque Vaughn




At 29, Jacque Vaughn had tamed her spending—and her debt. “I didn’t run it up so much that I couldn’t get out from under it.” And although it may have seemed as if the lessons learned from her parents hadn’t sunk in, she was ready for a change. A special incentive took the form of what she calls “a mean-spirited kick in the skirt.” When she moved on from her first job, her boss—her third in two years—said: “You’ll never do better than you did here,” financially. At the time, she was making $34,000 a year. “And I remember thinking to myself: Of course I can.”


Meanwhile, Jacque’s parents had some advice. “‘You’re giving all your money to the landlord,’ they said. ‘Buy an apartment. You don’t have to love it.’” Working with a budget of $125,000, in 2000 she found an 800-square-foot condo at Crosspointe by Aloha Stadium. It was leasehold, with 20 more years to run, meaning she could end up with nothing for her investment. “Any less time on the lease and banks wouldn’t finance it,” she recalls. Her Realtor thought she might be offered a deal on the lease down the line, however.


“I gambled on it,” she says, “thinking it would be the same as paying rent.” In the end, the landowner offered her the chance to buy after five years, for an additional $46,000. “The day I bought it was really exciting and liberating. I was owning my life.”


She also owned an investment property that is now worth $400,000. When she met a man and started a serious relationship, she says, “I said, ‘This is the way to go, this is how it can be done in Hawai‘i. If we can buy property and rent them for close to the mortgage and stay budget-neutral, we should do it.’” By the time they were married, six years later, they each had two properties—hers at Crosspointe and his in Mililani.


Then her husband took an overseas posting in Sicily. “We got all our moving expenses paid for by the government, we could rent out our place, let it appreciate and let someone else pay the mortgage.” While an immediate financial boon, the four-year sojourn would end, however, in divorce.


“You work so hard to learn your lessons and do well, and then you get married and divorced and it can be disastrous.”—Jacque Vaughn




Stuff happens. Things fall apart. Disaster strikes even the best-prepped.


After separating from her husband, Jacque Vaughn moved back to Hawai‘i in 2009 and into her original Crosspointe condo. “I remember being shocked—there was nobody at the mall, nobody at restaurants, For Rent signs everywhere.”


With the divorce, she says, “there was a financial reckoning.” But she was able to find her footing. “You need to have a hard times strategy,” she says. “I think you should always put yourself in a position where you’re prepared for the worst. If you have strategies in your life that are solid and good, you’re going to weather the storm, whether recession, losing your job or divorce.”


Of particular importance was keeping a level head in dealing with the end of her marriage. “Fortunately there was enough respect in the relationship that I could say, ‘Hey, you came in with two properties, I came in with two properties, let’s walk out of the marriage with what we came in.’ I don’t think we even used a lawyer. We used a paralegal.”


By working the problem, not the grievances, Jacque avoided the divorce penalty that many women pay (they typically lose 20 percent of their income in the aftermath of a divorce). She also never lost touch with her career while overseas. Among the companies Vaughn did long-distance consulting for was a former employer, the Hawaiian Humane Society. Upon her return, she says, “they welcomed me back with open arms.” And it was here that she met her future husband, Keoni.


When disaster strikes, she sums up, “the only thing I can recommend is make a thoughtful decision, not an emotional one.”




Good planning and financial transparency have a cumulative effect in the typical family’s life cycle. Learning to talk dispassionately about finances with members of the younger and older generations reduces friction and misunderstandings. Keeping everything under wraps, however, virtually guarantees a struggle, even a fight, that can inflict ruinous costs and permanent emotional damage.


For Keoni Vaughn’s family, everything fell apart when his 104-year-old part-Hawaiian great-grandmother died. “Her trust went into effect and it was a total nightmare. My grandmother came to me for help—so, in my 40s, this is the first time my family has ever talked about money. Before when I asked, it was, ‘None of your business, pal.’”


As often happens in large, complicated multigenerational families, various members had cut different kinds of backstage deals with each other and the great-grandparents. There were trusts within trusts, with cloudy wording. Different properties were involved. The main trust had been written long before, but both the great-grandfather and one of two brothers had died. Members on the Mainland were out of touch.


But at least Keoni had a different way of looking at money; watching and dealing with Jacque’s family had been a revelation. “They treat me like their son,” he says of the Smiths. “There’s no holding back. They talked to me about stocks and bonds. They started me thinking about property and real estate.”


Within his own family, on the other hand, things escalated to the point of one of the surviving brothers threatening to sue, even if the costs would sink the estate and force the sale of properties at auction. Keoni brokered a deal that diminished his own grandfather’s inheritance, but allowed a clean break. (The malcontented octogenarian moved into a family property and a month later passed away.)


Now, Keoni Vaughn says: “I’m breaking the mold when it comes to my family. I lived a life of secrets. To me that’s just so detrimental to those left behind.”


Almost four years ago, Jacque and Keoni adopted a son, Hunter. “This year my husband and I undertook the emotional process of setting up our own trust,” says Jacque. “And it was a life-changing experience to come face to face with our own mortality and scenarios that can empower or cripple your heirs. Inheritance can rob heirs of ambition and of truly claiming their own life and we are mindful of that and have seen it happen.”


Adds Keoni: “If we die, I don’t want our son to have access to the trust until he’s 30, and then only for education and medical purposes. He’s required to go to school to access any of this money.”


Today, Keoni is the executive director of the Lāna‘i Cat Sanctuary, which is also a tourist attraction enjoying national attention, including a recent CNN profile. He commutes from O‘ahu and is proud he just got 100 percent of his employees to sign up for the 403(b), the nonprofit’s 401(k). “I felt so passionate about getting them started in the right place,” he says.


“The people who are open do better. The open people learn from each other. It’s the only way to get there.”—Keoni Vaughn


A few years ago, Jacque Vaughn took a deep breath and started her own business, Transcendence Pacific LLC, a community engagement consulting company. “My parents grew up much less affluent than our upbringing,” she says. “They received nothing from their parents upon their death except for memories and mementos. And yet they have created a wonderful lifestyle and comfortable retirement. They set themselves up to ensure they will never have to depend upon their children for anything and they did it in Hawai‘i. And they expect us to do the same, by their example.”