In 2010 I had been recruited by a hui of investors on Oahu, and we were flipping houses at foreclosure auction, so I had been trained how to find deals and what to look for.
I've always been a good saver, so I had about $50k I'd earned from selling real estate to use as a down. The first house I bought was a duplex in 2013. I actually showed the house to a client, turned out he couldn't qualify, but then my mortgage broker pointed out I could buy the house, so I did. The downstairs tenants more than paid for the mortgage, I decided to live upstairs. Once I didn't have to pay rent ($1000/mo at least on Maui), that cut my living expenses by a third. I got a HELOC on the house and was able to tap my equity to use on other deals.
I kept saving money and reinvesting it in real estate. Living off my own cashflow happened within three years of buying my first property since I was used to $30k a year income. I was single, no dependents at the time.
I partnered with a local attorney to raise more capital to acquire high return properties. I had consulted him on an eviction, and he noticed what I was doing and wanted to get in on the action. I also had some partners on flipping projects, but I much prefer buy and hold. I own a mix of long- and short-term rentals, but I initially started out with long-term. Rents are pretty high here on Maui, so back in the day it was way easier to find cashflowing properties before values skyrocketed.
I was so focused on working that all of sudden, around 2016 I realized I'd gotten pretty rich. Then I got married had kids and started to enjoy my life. But it is different not having a 9-to-5. Most people my age don't have the amount of leisure time I do, so I just work out a lot.
Now I'm a single mom, and my daughter is my #1 priority, but I only have her half the time. So still out there making money but my new goal is finding a life partner . . . which is way harder than real estate LOL.
Bottom line, it comes down to dedication and focus. I never in a million years thought I would be living on Maui as a real estate mogul, but hey life always surprises you. Hard work is its own reward.