Celebrating Over 22 Years of Being “Unemployed” on Maui
It was March of 2003. I got my real estate license when I turned 18. No salary. No guaranteed paycheck. Just me, a license, and the decision every morning to go find work. I was poor, hungry, and determined…
Some call that having a PHD!
Since then, for the last 22 years, I’ve technically been unemployed. That’s the reality of this business. What have you done for me lately?!? Every day starts at scratch. Your future (and your family’s future) depends on whether you create opportunities each and every day.
The Challenge of Maui
Maui is an absolute paradise. Arguably the best place in the world to retire. Truth be told, it’s also one of the hardest places to make a living. Doctors, lawyers, and even engineers struggle to cover housing, cars, insurance, and in many cases multiple children with private tuition. Many families need two incomes to make it work. So how can a Realtor survive in a place where even high-earning professionals struggle? 3 words…
You gotta grind!
The Market is always shifting
When I started real estate in 2003, the market was in one of its boom cycles! You might remember.. Stated income loans. No supporting documentation lending environment.
It was wild.
I just finished 7 years at Seabury Hall and had big dreams to follow in my father’s footsteps…You could make really good money. If you worked hard and stayed focused at one of our new home subdivisions there was no ceiling on my income potential. But those years didn’t last forever. The Great Recession hit in 2008.
It was brutal.
Lots of short sales and bank owned properties in 2009 and 2010. Lending really dried up. It felt like the sky was falling. I had just graduated from the University of San Diego.
But then…recovery!
We sold a bunch of properties at Hoolei to our friendly neighbors from the great white north when their Canadian and US dollar was at par. Then another wave of growth. Through it all, one truth remained: if you didn’t plan ahead, the down years would friggin break you. You must save at least 10% of every dollar you earn (at a minimum) and invest.
Today the business looks completely different. Buyers don’t wander into open houses the same way. They find their agents and their future homes online. Some find their agents through Google, others through ChatGPT. They show up with MLS numbers in hand from Redfin or Zillow. The glossy magazine ads and billboard benches just don’t see the same ROI as they once did.
What Changed (and What Didn’t)
When I first started in the business, we were still using fax machines, in-person signatures, and tons of paper files. Now? Purchase contracts are 14+ pages, signed electronically, and delivered in seconds. Buyers expect instant answers with an ApplePay or Amazon click and ship mentality.
If you don’t pick up the phone or respond in 5 minutes, potential clients will move onto another agent. Technology has reshaped how we work. But here’s the bold truth: real estate has always been, and will always be, about people.
Properties follow rules.
People don’t.
Some people want data, other people want stories. Some want everything right now, others just want to feel heard. Success comes from learning to meet people where they are at that specific moment.
Lessons Over 22 Years
It hasn’t been a straight line. I’ve worked on roofs. I’ve sold off parts of my cherished bourbon collection and other assets when times got tough. I’ve done whatever it takes to keep moving forward with my family.
The best agents don’t slow down when the market gets hard. They double down.
Some clients take months. Some clients take years. One buyer worked with me for 13 years before finding their dream home in Wailea. We recently closed a listing that was 10 years in the making. Some deals feel like pennies per hour while others feel like hitting it out of the park. That’s simply the reality of real estate.
Still “Unemployed”
Now, over 22 years after getting my license, I’m still proudly unemployed. I wake up every day with no guaranteed income… but with the opportunity to build something bigger. My father Dano works alongside me as my business partner. Both of my children Gavin and Sienna were born and being raised on Maui. My wife Shannon has been the constant rock through it all. And with Coldwell Banker Island Properties, the Sayles Team and I have had record years, armed with the best tools and technology to serve our clients at the highest level.
So yes. I’ve been unemployed since March 2003. And I wouldn’t have it any other way!
Contact a Maui Real Estate Specialist
Yes we will always be your trusted advisor in the real estate market. But it’s so much more than that! A REALTOR should be that professional who recognizes their role in supporting your wealth building and preservation. Helping to magnify wealth is one of the core values of The Sayles Team; a set of guiding principles for how we serve our clients at the highest level.
As experts in the field, we are constantly learning. This is all about providing guidance, making the wisest choices for the future. If someone you care about needs such guidance or recommendations, please share our contact information. We would be honored to help them! As ever, we are here to provide resources. Reach out today for your up to date, in-depth market analysis or an evaluation of your property’s value.
Aloha,
Anthony Sayles R(S)
808-280-6532