My Story - Devin Tryan | From 1 Sale to 7-Figure Entrepreneur

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Something real and personal
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Where It Started

One Sale. Two Years. Zero Quit.

I got my real estate license at 19 years old. And for the next two years, I sold exactly one home.

One. In 24 months. Let that sink in.

I was studying civil engineering at the University of Hawaii at Manoa. My friends were getting "real" jobs with real paychecks. My family probably thought I was crazy. And honestly? Some mornings I woke up wondering if they were right.

But I didn't quit. Something inside me (stubbornness, maybe, or just a refusal to accept average) kept me going. I didn't come from money. I didn't have a network. I didn't have a mentor handing me leads on a silver platter.

All I had was work ethic and a belief that I could figure it out if I just kept showing up.

"The version of me that was eating ramen and barely making rent would never believe where I am today. And that's exactly why I do what I do: because I remember what it feels like to be stuck."

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The Turning Point

Then Everything Changed.

I went all in. I attended a Keller Williams sales training that rewired how I thought about prospecting. I started chasing expired listings and FSBOs: the leads nobody else wanted because they were "too hard."

Within 36 months, I went from 1 sale to 37+ transactions a year. My first expired listing? A $1.55 million home. I was 25 and earning seven figures.

But here's what I realized: it wasn't luck. It wasn't talent. It was frameworks. It was systems. It was the right mindset and the right habits executed with relentless consistency.

And if I could learn it, anyone could learn it. I just needed to share it.

What I've Built

I Didn't Stop at One Business.

Once I cracked the code on scaling, I couldn't help myself. I had to build more: across completely different industries.

📈

Talk Realty & Pineapple Homes

What started as a solo hustle became my own brokerage and one of Oahu's top real estate teams. Talk Realty is the brokerage I wished I'd had when starting out: world-class training, elite culture, and a team that's top 1% in Hawaii with hundreds of 5-star reviews and record sales.

🧗

HI Climb

In the middle of a global pandemic (when most people were pulling back), I went all in on a dream. HI Climb is a 17,350 sq ft climbing facility in Kaka'ako. Top rope, bouldering, lead climbing. Because real entrepreneurs take 100% action, even when the timing feels wrong.

💻

CMA Everyday

I saw agents wasting hours on manual outreach, so I built a software product to fix it. CMA Everyday automates direct mail for real estate agents | sending personalized letters with real-time property valuations and market insights. Listings on autopilot.

🎯

Elite Coaching

Entrepreneurs kept asking me how I did it. So I built a coaching program around the exact frameworks, systems, and mindsets that built everything above. Now I help other founders scale without burning out.

The Journey

How It All Happened

2014

Got My Real Estate License at 19

Jumped into real estate while studying civil engineering at UH Manoa. Sold one home in two years. Refused to quit.

2017

The Breakthrough

Went all-in on prospecting. Mastered expired and FSBO strategies. Transactions exploded from 1 to 37+ per year.

2018

7 Figures at 25

Listed a $1.55M home on my first expired presentation. Hit seven-figure income. Earned 5-Star Zillow Premier Agent status.

2019

Built Talk Realty & Pineapple Homes

Grew from solo agent to founding my own brokerage and building a full team. Became top 1% in Hawaii with record sales and hundreds of glowing reviews.

2020

Launched HI Climb | During a Pandemic

Co-founded a 17,350 sq ft climbing gym in Kaka'ako while the world was shutting down. Because entrepreneurs don't wait.

2023

Built CMA Everyday

Saw agents wasting hours on manual outreach and built a SaaS product to automate direct mail with real-time property valuations. From real estate to software founder.

Today

Coaching Entrepreneurs to Scale

Running three businesses and sharing everything I've learned with ambitious entrepreneurs ready to go to the next level.

The Results

By the Numbers

Top 1%

Real Estate in Hawaii

By volume and transactions across all of Oahu.

7 Figures

Income by 25

Through focus, systems, and relentless execution.

3

Businesses Built

Real estate, fitness, and SaaS | across multiple industries.

37+

Deals Per Year

From 1 sale in 2 years to 37+ annually.

5 ★

Zillow Premier Agent

Hundreds of 5-star reviews from satisfied clients.

🎫

Featured In

Hawaii Business Magazine, Vulcan7 Roadmap, and more.

Beyond Business

What I Actually Care About

Success without fulfillment is the ultimate failure.

I didn't build three businesses to be chained to a desk 80 hours a week. I built them to have freedom: to surf, to climb, to travel, to be present for the people I love.

I believe entrepreneurs are the engine of the world. We create jobs, we solve problems, we push everything forward. But too many of us sacrifice our health, our relationships, and our happiness in the process.

My mission is to show you that you can have the business, the freedom, and the impact, without grinding yourself into the ground.

Born and raised in Hawaii. Living on Oahu. Building a life I never want to retire from.

Ready to Scale? Let's Talk

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I didn't come from money.I came from obsession.