Waikiki was good to me.
I was part-owner in a luau and island tour company.
Selling experiences.
Promoting.
Making good money.
But I knew there was another level.
A lot of the people I’d met who built real wealth didn’t do it through jobs.
They built it through business.
Through ownership.
Through real estate.
And I wanted in.
Not because I was struggling.
Not because I doubted myself.
I just wanted to operate at a higher level.
At the time, I was building Key to Waikiki. I had sold my shares in the tour company trying to step into something bigger.
Then my business partner passed away unexpectedly.
That chapter closed fast.
Not long after, my girlfriend at the time was looking to buy a condo. She asked me to go with her because I knew Waikiki inside and out.
That’s how I met Alesia Barnes.
She was sharp.
Funny.
Driven.
Building her real estate business aggressively.
Leads were coming in.
Advertising was working.
Momentum was there.
But I could see the strain.
We’d be driving to showings, me in the back of her Range Rover, and she’d be juggling everything.
Phone missing.
Low on gas.
Appointments stacking.
Trying to scale in real time.
I had just won the state championship in Toastmasters. I was leaning into public speaking. Thinking about business coaching. Looking for entrepreneurs I could help.
And sitting in that Range Rover, I saw it.
I could help her.
And I could finally enter the world I’d always wanted to understand.
So I told her.
“I can close. And I’ve always wanted to get my real estate license. If you pay for me to get my license, I’ll come work for you and help you close your leads.”
She agreed.
About a week later, her assistant mailed me a check to cover the course.
I remember holding that check and thinking:
This is real.
Before I was licensed, she invited me to sit in on a Wednesday at her home office in Lanikai.
It was a different universe.
Structured.
High-end.
Every Zillow click tracked.
Every inquiry logged.
CRM organized.
Data everywhere.
They let me try one call.
First call ever.
I followed the script.
Built rapport.
Booked the appointment.
When I hung up, the entire room exploded.
They had all been silently listening.
Then clapping.
Cheering.
Looking at me like, “Who is this guy?”
It felt straight out of Wolf of Wall Street.
That was the moment.
I was supposed to go back to Waikiki the next day.
Walk the streets.
Sell tours.
Wait until I finished the course.
There was no chance.
Instead of driving into Waikiki that morning, I drove back to Lanikai.
I wasn’t scheduled.
I wasn’t expected.
I just showed up.
I walked in and pitched her a bigger plan.
“Let me work with you full-time while I get licensed. I’ll help organize the leads, tighten follow-up, help build the machine.”
I asked for $4,000 a month.
She laughed.
She said she couldn’t afford it.
And I just sat there.
I had played that conversation out in my head.
I was sure she was going to say yes.
Instead, I looked around her office, trying to figure out my next move.
That’s when I saw the box of designer shoes in the corner.
“What are those?”
“They’ve been sitting there.”
“Can I sell them?”
She said yes — I could sell them to help get by until I got my real estate license.
The trade-off was simple:
I’d work as her assistant while I studied and learned the business from the inside.
She brought out boxes of shoes, purses, dresses. Some still with tags.
One Chanel bag sold for $1,600.
That became my bridge.
I sold designer items on eBay.
Organized systems.
Helped structure her business.
Studied at night.
And I made another decision.
I traded in my old Tahoe that didn’t even have working AC and bought a white Range Rover — my dream car.
The payment was about $400 a month.
I told myself I’d drive Uber in the mornings before real estate just to cover the payment.
Three weeks.
That’s how long I drove Uber.
Then I got a deal in escrow that was big enough to let me stop.
May 2016, I got my real estate license.
Driving over the Pali from Waikiki into Lanikai felt like crossing into another dimension.
Waikiki wasn’t wrong.
But it had a ceiling.
I didn’t slowly loosen the golden handcuffs.
I broke free of them.
That real estate license wasn’t just about money.
It was the moment I escaped selling on the streets of Waikiki…
and stepped into selling the suites above them.
Streets to Suites.
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