Curious by Default

Tyler
Graham

I like learning how things work — businesses, systems, people. Most of my best conversations start with "tell me about what you're building."

Tyler Graham
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It started with a question. How do small businesses actually work? I found out in the desert — at a vineyard in Arizona where every day was different and nothing went according to plan.

Since then, I've been collecting stories. Business owners, entrepreneurs, people building something from nothing. I've learned more from listening than I ever did from textbooks.

The common thread? I like understanding how people think. What they're trying to build. What gets in the way. That curiosity has taken me to some interesting places.

The Story So Far

Four chapters, a few lessons

Chapter One

The Foundation

Colorado · 2008–2014

Before the business world, there were fairways and park trails. I spent years keeping golf courses pristine and managing county park crews — work that started before sunrise and taught me more than any classroom could.

Managing grounds crews, coordinating with county officials, solving problems on the fly. It wasn't glamorous, but it was foundational. Some lessons only come from showing up every day, regardless of the weather.

What I learned: Hard work compounds. Show up, do the work, and the rest follows.

Chapter Two

The Desert Years

Arizona · 2014–2018

A vineyard in Arizona sounds romantic until you're in the tasting room at 6am prepping for the day. But that's where I met my first small business owners — people who'd bet everything on an idea.

I worked in winery and marketing operations — running events, managing social media, figuring out how to tell the vineyard's story. But mostly I listened. To customers. To the owners. To the guys who'd been farming that land for decades.

What I learned: Every business has a story. The best ones know how to tell it.

Chapter Three

The Systems Era

Colorado · 2018–2024

Colorado was about going deeper. I helped businesses adopt technology — CRMs, automation, digital tools. But the tech was never the point.

The point was understanding what people were actually trying to do. A restaurant owner who wanted to spend less time on paperwork. A startup founder drowning in spreadsheets. Their problems were my puzzles.

I also spent time in classrooms. Teaching kids reminded me that the best way to learn is to explain things to someone else.

What I learned: People don't want technology. They want their problems solved.

Chapter Four

The Return

Connecticut · 2024–Now

We moved East to explore something new — a fresh start in a new area for our family. Started Mainstreet Origin. Got back to basics.

Now I spend most of my time meeting people. Local business owners, entrepreneurs, anyone building something interesting. We grab coffee. They tell me what's going on. Sometimes I can help. Sometimes I just listen.

What I learned: The best networking doesn't feel like networking.

"I've learned more from listening than from any business book."

Beyond Work

What I'm curious about lately

🏃

Running

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On the Trail

Clears my head like nothing else. Some of my best ideas show up around mile three — no phone, no distractions, just thinking.

👨‍👩‍👧

Family

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The Main Thing

Being a husband and father. Everything else is secondary. This is the work that matters most.

🍳

Cooking

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Work in Progress

Learning to make meals for my family. Still figuring it out, but that's the fun part. Every dish is an experiment.

🏘️

Community

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Local Impact

Creating things that make my neighborhood better. Small efforts add up. Big change starts small.

Now

Greater Hartford, Connecticut

I'm based here now. Running Mainstreet Origin, meeting local business owners, and always looking for interesting conversations.

If you're building something — a business, a project, an idea — I'd love to hear about it. No agenda. I just enjoy learning what people are working on.

Coffee's on me.

💬

Start a conversation

No agenda. Just curious.

Get in touch

Thanks for scrolling this far

Now it's your turn — tell me what you're building

I'm always up for a good conversation.