Matthew Tregoning

Last week of our 4-week stay on Oahu and being back here has me reflecting on how much life can change in a few years….

When me and Genevie met and lived on Oahu from 2017-2021 I wasn’t building the life I have today. I was building the foundation for it.

Reading hundreds of books on investing, business, and personal development.

In the gym everyday.

Saving and investing every dollar I could.

Living way below my means.

No fancy apartment.
No expensive dinners.
No unnecessary spending.

Most people saw paradise.

I saw an opportunity.

An opportunity to learn, grow, and buy back my freedom.

There were plenty of times I questioned if it would ever pay off.

But I kept showing up.

Day after day.
Year after year.

Now I’m back on the same island with my family, staying for a month without asking permission from a boss, without worrying about vacation days, and without rushing back to a job.

The freedom wasn’t built overnight.

It was built through thousands of small decisions that nobody saw.

Every workout.
Every book.
Every dollar invested.
Every sacrifice.

Looking back, it was worth every bit of it.

Grateful for the journey, grateful for the freedom, and grateful to experience it all with my family.

Great experience learning and training with the legend in Oahu, and huge thank you to and the other coaches I got to learn from while training there throughout May.

Jiu Jitsu has taught me more about life, discipline, humility, and business than my business degree ever did.

Every round exposes what you need to work on.

No excuses. No shortcuts. Just reps, pressure, adjustments, and growth.

Grateful for the opportunity. Oss 🤙

Crazy to bring our son back to the island where our story really started. We lived here for 4 years while I was in the Air Force, and so many of our best memories were made here.

The surf sessions, BJJ training, late night drives around the island… there’s just something special about this place that’s hard to explain unless you’ve experienced it.

Feeling really blessed to spend a month here with my family and show Levi all of our favorite spots. Grateful for this season of life. 🤙

Year 1: I panicked in February when bookings dropped. 
Year 2: I figured out the pattern. 
Now: I use February strategically. 
 
I lower prices slightly. Stack reviews and fill my calendar. 
Then I raise prices 40-60% in March when spring break hits. 
 
February isn’t a problem. It’s a setup month. 
Play chess, not checkers 
 
Comment ‘earn’ ang get the step-by-step February game plan

Save this if you’re playing the long game and win the game 
 
 
(Airbnb,airbnbhost,AirbnbTips,shorttermrental,vacationrental,airbnbsuperhost ,airbnbstrategy,revenuemanagement,vacationrentals,airbnbbusiness,february 2026)

When I started in 2021, I thought I needed to impress to get booked. 
 
Turns out, I just needed to take care. 
 
Guests don’t book Airbnbs for luxury. 
They book them to feel comfortable. 
 
 
Save this if you’re planning your 
Airbnb🤍 
 
If you don’t want to figure everything out the hard way, I have built a guidebook on starting Airbnb from scratch.Just Comment “”27”” 
 
Answer most of them! 
[Airbnb, Airbnb tips, Short-term rental, small business, passive income, Airbnb checklist, Airbnb setup, Airbnb profitability tips, increase Airbnb occupancy, rental income, Airbnb business ideas, how to start Airbnb in usa, Airbnb management service usa] 
 

When I started, my occupancy was inconsistent. 
Some months were great. Others were slow. 
 
I was leaving thousands on the table because my listings were just… average. 
 
Then I made 5 strategic additions that completely changed the game. 
 
The result? 
78-100% occupancy year-round. 
Premium pricing. Consistent bookings. Better reviews. 
 
These weren’t expensive upgrades. 
They were strategic upgrades that paid for themselves in the first month. 
 
If your occupancy is inconsistent, it’s not the market. 
It’s the setup. 
 
Want my full Airbnb setup guide with the exact products, links, and checklists I use?  
Comment ‘SETUP,’ and I’ll send it straight to your DMs. 
 
(Airbnb setup, airbnb )”