Broker of the Year


Meet the broker of the year

Here is a blast from the past … I was so excited and honored to be recognized as Broker of the Year early in my career! These are some thoughts I shared upon receiving this honor.
Wow… Broker of the Year! Can’t say I ever thought I would win such a prestigious honor in our real estate community! It is awarded to someone who has displayed great dedication to education and service; but has also exemplified an extraordinary professional standard. For some people I’m a little too outspoken… for others I’m a little too strong… but I guess like in the story of the three bears… there are some who think I’m just right! But how did I get to this place? I grew up the oldest of three preacher’s kids living in a dozen places, including Hong Kong, before graduating from high school. That made all of us able to talk to complete strangers… he is a professional entertainer… she has her law degree… and I sell real estate. Turns out this is the first piece I needed on the path to where I am today. Then after kicking around the country and trying college for a few years, I was the first person hired by the then-Baltimore Colts that fateful night when they moved to Indianapolis. I met the owner’s son, Jimmy Irsay, in a restaurant and he asked me to come to work for them the next day. That first month in public relations had a steep learning curve, with the move making national headlines and the NFL draft all in the mix. That gave me a huge insight into how the media works … piece number two. The next great job was when I took a transfer to the NFL office in California to work as an editorial assistant on the NFL’s game day magazine. NFL Properties was responsible for all the photos, logos, memorabilia contracts, etc. for all of the teams. I spent many hours typing in the edits that my boss had written in the margins of the stories penned by our staff writers and in the process learned the importance of the written art of storytelling… piece number three. As my time with the NFL ends… I fall in love with a guy from Hawaii! Unfortunately, that 20-year marriage recently ended but it was what brought me to my favorite place for the very first time. We move to Kona in ‘90 and as Kona would have it, I make a new friend who works on a new project that hasn’t started and is out in the middle of a huge lava field… called Hualalai Resort. Now in those earlier years as I was kicking around I had worked in some construction offices and had learned accounting so when they asked me to learn how to implement contracts, pay the bills, and help with construction schedules I was up for it! My boss was a Japanese national, and he taught me not just the construction piece but also the multi-cultural part as I learned to navigate what were unchartered waters for an American woman to be an integral part of this very Japanese and male-dominated project. Pieces number four and five… meet lots of great people and learn the local customs. Then in ’95 the unthinkable happens… my twenty year old step-son is killed in an accident shattering our lives. To mourn privately in Kona is not possible, so we moved to North Carolina to work through our grief. There, I answered an ad in the paper and ended up working for the number one salesman in Amway, Dexter Yager. For the year we were there I managed his jets, pilots, and multiple residences along with his schedule and assisted his son with running his company… wow, now that was something to be around lots of top sales guys making millions a year. Piece number six… rich guys put on their pants the same way I do. Back in Kona things are slow and work is tough to come by in ‘97… we are offered an opportunity in Bosnia where I will be the accounting manager for a UN project run by an American team… we say yes! Off to the frozen tundra of Drvar just before Christmas. Wow, good thing I was used to different cultures since this was what you would call immersion… no one but the team and the UN peace-keeping forces speak English, I’m not allowed outside alone, and I’m not allowed to drive a car, and there are no phones to speak of… that was an interesting few months! Oh, did I mention doing the accounting in three different currencies, no checks or credit cards, everything is done in cash and everyone has guns except us? We had some hilarious hair-raising times driving across the country to Sarajevo to pick up thousands of dollars in cash for payroll and equipment and racing back home before anyone could intercept us. Needless to say, it grew old after a while and this Kona girl longed to come home. Piece number seven… I don’t want to live anywhere in the world but Kona! Back in Kona, a friend from the Hualalai project calls about a new huge subdivision just starting in South Kona called Hokulia. I jumped at the chance to go back to work with this friend and into construction. This time I actually started doing some of the management of subcontractors, writing the contracts and approving the payments. As Hokulia began to struggle with what turned into years of lawsuits, the edge and feel of the project began to change so I left. With tears in my eyes, I packed up my office not knowing where the next part of this journey would lead. Piece number eight… no job is worth your peace of mind, no matter how much you love the place. But where God closes a door, He opens a window… and what a window it was! Hualalai Village in 2000 was just getting started and I’m hired by a friend to assist in being the conduit between the developer / buyers / sales agents and the construction company as well as to build and run the design center for the interior finishes on the condos. The construction part I get, but the rest is Greek to me. With the help of a fabulous interior designer I started to get the hang of how to make all of the options work for the clients. Now someone suggests I get a real estate license since I’m working directly with the buyers assisting them to pick out not just their finishes but the right condo in the project, so off to real estate school I go… I had no idea what would come next! One of the financial backers in the project wanted to buy a house in Kona and wanted me to work with them to do it. Well a baptism by fire is about as close as I can explain it… and almost $2 million later they are moved in and settled in their new place. Now comes the crazy part… the commission check. Mind you I’m a rookie and our splits aren’t very good… but it was enough for me to rethink the idea of selling real estate full-time and give up my corporate paycheck that I so dearly loved. Pieces number nine, ten, and eleven… I have a good eye for finishes, the buyers like working with me and it’s at least partially about the money! I put the check in the bank, quit my job and give myself six months to make my first sale. That was in August of 2003… and the rest as they say is history!
Gretchen Osgood, REALTOR®
Principal Broker/ Owner

My Real Estate History in West Hawaii

Clark Realty, Inc.

• 2003 Clark Realty Rookie of the Year
• 2004 Sold 30 properties totaling $12M

Hawaiian Isle Real Estate, LLC

• 2006 Opened new office as Principal Broker and Owner
• 2006 Sold 31 properties totaling $17M #2 Residential Resale Transactions Keauhou to Hawi
• 2007 Sold 26 properties totaling $12.6M
#1 Residential Resale Transactions
Keauhou to Hawi
• 2008 Sold 26 properties totaling $11.6M
#1 Residential Resale Transactions
Keauhou to Hawi
• 2009 Sold 17 properties totaling $6.7M
#4 Residential Resale Transactions
Keauhou to Hawi
• 2010 To date 24 properties totaling $8M
#6 Residential Resale Transactions
Keauhou to Hawi


Prince Properties, Inc.

• 2005 Prince Properties Agent of the Year
• 2005 Sold 40 properties totaling $21M


Career Sales:

Sellers: 111  Buyers: 83  Total Sales: 194
Total Sales Volume: $92M

Professional Associations:

West Hawaii Association of Realtors
• Treasurer 2011
• Broker of the Year 2010
• Distinguished Service Award 2010

Hawaii Association of Realtors
Finance Committee Member
National Association of Realtors
Certified Luxury Home Marketing Specialist
Council of Certified Residential Specialists