What Prison and Addiction Taught Him About Money and Life
Addiction, bad decisions, and quiet consequences eventually force a reckoning
Most people don’t hit pause on their life by choice.
Sometimes it’s addiction. Sometimes it’s bad decisions stacking on top of each other. Sometimes it’s the moment you finally run out of room to keep lying to yourself.
For Kolaiah, that pause came in the form of prison.
Not the dramatic kind you see in movies. Just long, quiet hours where there’s nowhere to go and nothing to distract you from the truth. The kind of place where excuses don’t hold up very well.
The Cost of Avoiding Responsibility
It’s easy to talk about “rock bottom” in hindsight. It sounds cleaner than it feels.
Before prison, Kolaiah’s life was shaped by addiction, denial, and the slow erosion of trust.
He stole from his own mother to support his habit. Addiction narrows your world until consequences feel distant and everyone else feels optional.
That’s how avoidance works. You don’t wake up one day and ruin your life. You inch toward it, one rationalization at a time.
Most of us never get forced to stop long enough to see that pattern clearly. Kolaiah did.
Stillness in a Jail Cell
Prison has a way of stripping things down.
No noise. No status. No pretending you’re just “going through a phase.”
What surprised Kolaiah was the people he learned from.
Inside, he crossed paths with men who’d built real businesses, handled real money, and made real mistakes. Not the caricature of criminals, but flawed humans who understood systems, discipline, and long-term thinking.
It wasn’t formal education. It was real-world perspective.
And it planted a simple but dangerous idea.
Maybe his life wasn’t over.
Maybe it just needed to be rebuilt.
Starting Over With Nothing
When Kolaiah got out, there wasn’t a victory lap waiting.
No savings. No shortcuts. No one handing him a blueprint.
He worked multiple jobs. He showed up. He stayed clean. And instead of chasing fast money, he invested in learning. Even when it scared him. Even when he had to borrow to do it.
That decision mattered.
Because starting with nothing forces clarity. There’s no room for ego. No room for pretending. Just a quiet question you have to answer honestly.
Am I willing to do this the long way?
Real Estate as a Tool, Not the Goal
For Kolaiah, real estate wasn’t about flashy deals or social media wins.
It was a way to create stability. A way to build something that didn’t depend on constant hustle.
Over time, that system grew.
Fix-and-flips turned into rentals. Rentals turned into development. Development turned into building homes for local families in Hawaii, one of the hardest places in the country to do it.
The point wasn’t just income. It was freedom. And eventually, responsibility.
Real wealth, it turns out, isn’t about how much you make. It’s about how much you can sustain.
A Final Thought
Your past doesn’t disappear.
But it also doesn’t get to make your decisions for you.
Sometimes the lowest point in your life isn’t a dead end. It’s the place where the noise finally stops long enough for you to hear the truth.
And from there, you get to choose what happens next.
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