The long way home

The line I come from

I was born in Jacksonville in 1995, while my father was at Bible college there. My parents had a baby, no money, and a long way between them and home.

Home was Columbia, Maryland. They both grew up there and went to the same high school. My father went to the Naval Academy, but he left before he finished it.

Further back on my mother’s side there’s a man the family called Daddy Jim. He joined the Washington Evening Star in 1895 and became the first reporter to cover the White House full time.

His method was to stand outside in the weather and talk to people on their way out. The story the family tells is that Roosevelt saw him out there in the rain and had a desk put inside for him. I don’t know if that part’s true.

On my father’s side there’s plenty of service to the country and good old fashioned country living. My Gigi is without a doubt the matriarch, and she had her own career in PR working with the likes of 20/20. Her stories about how the industry really works have paid dividends to my father, to me, and to others.

There’s also a fascinating story about how we got the Conway name. As it’s told, a white Irishman living in New York who was a proud abolitionist met a formerly enslaved Black woman and they fell in love. He went on to write something like thirty books in his time. I’m not completely certain on all the facts, but it’s a nice thought to be an American with Black and white in your DNA and a genesis story full of romance.

Jacksonville, Florida

Our little slice of heaven

There was a sister before me. Victoria. She was born in May 1993 and she lived ten days. I was born twenty-one months later, in the same city.

All four of the brothers have been to her grave together. She’s in this family. She was just never in it at the same time as any of us.

My parents’ house was on the riverside of town. Somebody else lives in it now, but my parents say it looks pretty much the same.

My father graduated from Bible college in Jacksonville in 1997, in the school’s first accredited class. He’d been planning on a chaplaincy, but what he got was a church, four boys and a long run of towns.

I was three when we left. He took a job on the Mississippi coast, and that’s the only move we did as a family that I don’t remember.

Jacksonville, Florida · the second time

Home again home again

I came back to Jacksonville at twenty-seven, on my own, for a job. I’d left it at three, so I had no memory of the place to go on.

I was doing marketing by then. A company called Givebutter hired me to run their video, their audio and their paid media.

Before I left to go back to Wilmington, I transitioned to a marketing agency based in Austin. Opening Blue Roll taught me what I know about running a creative agency, but much of what I know about running a marketing team I learned in a room there, with people who thought entrepreneurial spirit was normal.

An aunt of mine had a place on a rough side of the neighborhood, and the dogs next door weren’t being looked after. We took in the mother and the whole litter, ran them through a rescue, and every one of them got a home.

I kept the one who almost didn’t make it - Panda. Her siblings kept pushing her off her mother, so she was small and underfed. But she followed me to Wilmington and then to California. That’s my girl.

By the riverside

We moved to the Mississippi coast in 1998, when I was three. Gulfport and Biloxi. My father had a job there and then a better one.

Timothy was born in 1998, Jeremiah in 2000, Noah in 2001. That’s four of us inside six years, and I was the oldest.

My father preached. He also conducted, back when he was younger, which is the person out front waving their hands while everybody else sings. My mother sang, and she ran the singers and picked the songs. That was most of our week.

I catch myself talking like a preacher these days. The way my father showed a room that something mattered. The voice was never limited to the pulpit and I picked it up without anybody teaching it to me. I think it’s incredibly lame and I do it anyway - for the plot, you know?

As a kid I was in the gifted program at Woolmarket Elementary. I trained at a Taekwondo school on Three Rivers Road with Timothy and my father, and I think I got to black belt before I was ten. Then I had to pick between that and baseball, and I picked baseball.

Every year my Gigi took the four of us to J.C. Penney and bought us matching outfits for the Christmas card. If we were home we mailed it up to her. But if we were with her in Maryland, she walked us in there herself.

That happened for most of my grade school. It was just her ritual and she never once skipped a year.

Mississippi

Talk about homegrown

When we got to Mississippi we had no money at all. Maybe my father wanted to chase the preaching, and maybe he thought it would be provided. I’m not sure which. We found a church with enough space upstairs, and that’s where we lived.

I have a flashback of the stairs that went up to where we slept. And one of waking up with a man standing over us, watching us sleep. He’d wandered in looking for help, which is what you go to a church for. Nothing happened. But it was still a notable event for a childhood.

I’ve never met another person who lived in a church because their family was that poor.

The younger two were born once we were in a house, with some stability around us. That’s the line between me and my brothers.

Timothy got kidney cancer when he was maybe two or three. I was maybe five or six. I remember him in a hospital bed with everything hooked up to him. My parents say I went into older brother mode. Then he got better, and I think I just put the whole thing down for years.

That’s what stayed. Any time we were roughhousing, somebody would say Tim’s only got one kidney. Everybody knew it and everybody said it.

My father was chasing the ministry. Timothy was sick. The bills came anyway. So my parents opened a cleaning company and took docks, warehouses, apartment complexes, car dealerships, whatever would pay. I did what I had to do and worked as a janitor as a child.

My parents got by with what they had.

Mississippi

Two dollars an hour

Two dollars an hour. Nobody in that house called it a job, including me. I think I was about seven when all four of us were in on it.

Trash cans were the big one. Every can in the building. Pull the bag, empty it into the big bag, tie it off. New liner in the can, and a spare liner folded into the bottom for next time. Eventually we got a smell-good spray for the inside, which was a fun addition to the whole routine, because I would try to spray the bottle like a squirt gun and make a game out of finishing a can.

Then scuff marks. You take a long pole with a tennis ball cut and jammed on the end, and you lean on it over every skid mark a shoe or a machine left, all the way around the building. Car dealerships especially. Where the pole wouldn’t do it, I used my own shoe.

Mopping and vacuuming came later, when I got bigger.

If Timothy was old enough to sit with the younger two, I went in and worked, then came back out and sat in the car. We didn’t talk much there. We were working, and that was it. The only real time I went and talked to my parents was when the job was done.

I don’t know that I ever worked out as a child that other kids weren’t doing this. That came later, sitting with friends as an adult while people talked about their childhoods and nobody was working.

I’m proud of those years. They taught me work ethic, and they taught me that sometimes you just take the job nobody wants.

I can tell you’re a good person if you treat the janitor with as much respect as the CEO.

I’ve been in rooms where I watched that difference get handed out.

Mississippi

August 2005

Katrina came in August 2005. My father was away for work, so my mother boarded up the house, put four boys and the dog in one car, and drove us out.

We went up Highway 90 through Gulfport and Biloxi with the sun out, and we kept going until we got to Maryland.

Woolmarket Elementary didn’t survive it. Neither did a lot of the houses belonging to the people I went there with.

My father went back before the rest of us did. There was a hospital on that coast that had to keep running and then had to close, and he was the one running the part of it that gets cleaned.

The house everybody grew up in

We went to my grandparents in Columbia, Maryland, and stayed maybe four months. My mother and my uncle grew up in that house, and the elementary school was close enough to walk to.

So we went to Thunder Hill Elementary, which is the school my mother and my uncle went to as kids. That happened because of a hurricane. There’s no version of our lives where it happens any other way.

My granddad kept a garden out back, maybe eight hundred square feet of it, maybe a thousand, with corn, peppers, lettuce and birdhouses galore. Behind the garden was an open field fifty yards deep. We threw frisbees in it. We threw boomerangs in it. We played tag until it got dark. Then we’d watch for deer, lightning bugs, foxes and all the critters of the night.

Columbia is threaded with walking paths, and you could take one to a lake or a park or to school. When it snowed we went sledding. I got bullied there the way I got bullied everywhere, but I loved that place anyway.

Home is where the heart is.

I played RuneScape for years by then and I still play it now. The friends I’d just left in Mississippi were logging on, so I could still talk to them at night. That came with me and almost nothing else did. Looking back, it’s this level of connection with technology that I’ve grown to love and work to bring to people.

We were back in Mississippi before Christmas. Leaving Columbia was bittersweet. Gulfport and Biloxi hadn’t fully healed. But we’d grown closer as a family.

Sixth grade with eighteen-year-olds

We lived in Hammond because my father’s job was eight miles away in Ponchatoula. Twenty months. Two schools inside them, and I was the new kid at both.

Nobody outside Louisiana knows where Hammond is. So we didn’t say Hammond. When the four of us talked about those years later, we said New Orleans.

Hammond Junior High for sixth grade, then Ponchatoula Junior High for seventh. There were metal detectors at the door in Hammond. Both schools put us in uniforms, so I got dressed the same way two years running.

I was eleven. Some of my classmates were eighteen. They’d failed enough years to be waiting on a birthday, because at eighteen the school system lets you go. What was waiting after that was the gang. Some of them sat at the desks around mine.

I got jumped more than once. I wasn’t fighting to fight. I was bullied, but what I had instead of size was a loud mouth and a rebellious spirit. I would find ways to make fun of them, and they did not like that.

There’s very little to look back on from this time of my life. But there are a few glimpses of hope, and a few great people who had an impact on me.

Miss Ellie had science and homeroom. She took me under her wing. She’s also the one who told me when I was clowning too much, or when I was letting the wrong people get to me. That was most of the year.

Mr. Perry had English. We read the classics. We read Black writers. He knew what was in our houses and what was in the street outside them, and he said the same thing to us all year.

We can and should be more in life. The current situation is not the outcome.

Louisiana

The train tracks

There was enough violence at Hammond that my mother petitioned the school board to get me out. She won. It cost me the bus. So she drove me. Ponchatoula in the morning, Hammond in the afternoon, the whole seventh grade year.

Hammond was almost all Black. Ponchatoula was almost all white. Between them runs a set of train tracks. It’s the thing people say about the South without meaning it literally. But there it was literal, and I crossed it twice a day in my mother’s car.

Two things can be true at the same time.

I went out for football at Ponchatoula on the first day of tryouts. I wore glasses. Regular ones, not sports glasses, and the helmet had to come down over them. They got bent. We ran drills in that helmet all afternoon and I hated every minute of it.

I went to the coach after that one practice and told him it wasn’t for me. Then somebody came to get me and I cried the whole way home. I had to tell my father I’d quit. It bothered me for a long time that I didn’t just stick it out.

I kept playing baseball the whole time we were there. Community leagues, all the way through, the same as Mississippi. But quitting football would create a chip on my shoulder I didn’t see coming.

Settle down

We got to Wilmington in December 2007. I was twelve. That was the fifth school system I’d been put into.

I didn’t arrive expecting to stay. I arrived expecting to leave, because that’s what had happened every other time, and by then I was good at it.

It’s almost like being a military kid. You learn to get in where you fit in, fast. You show people all of yourself quickly, because there might not be time to do it slowly. I think that’s most of why I’m as open as I am.

Knowing something about a person and knowing the person are different levels of depth.

This upbringing has provided the opportunity to have very few actual friends. The ones I have are five, ten, fifteen years deep, but everybody else is a colleague, an acquaintance, or someone I know.

I graduated from Hoggard High School. Met my best friend Austen Bertrand. I went out for football again, and this time I made the team and got play time. I even started my entire senior year as a defensive back. The contact lenses I eventually got helped a lot. I did four years of ROTC. Head of the sword team and squad leader. Happy as can be about a stack of ribbons and medals, the way only a kid in high school can be.

North Carolina

A storyteller’s dilemma

I went to UNC Wilmington for Communication and Media Studies. There was a film half and a behavior half of the school, and I took the behavior half.

For four years I was one of the UNCW Storytellers. You memorize stories, you drive to an elementary school, and you tell them all day. Pre-K up to fifth grade, two stories and sometimes three, dozens of schools.

A loud story with a lot of acting out lands in kindergarten. The same faces in a fourth grade classroom get you nothing. The little ones believe the bear is walking through the woods. The fourth graders know you’re telling them a story about a bear walking through the woods.

It runs the other way too. Give the little ones something you can act out that’s too complicated to follow and they light up, then interrupt, start playing and lose it. They can get involved with your animated faces, but they can’t get involved with the story.

The same story could work in one fifth grade class and die in another one across town. Some schools had money and some didn’t, and I think that was most of it. Some of those kids were going home to work, and I knew, because I’d been one of them.

You tailor the story to the room you actually walked into, not the one you thought was there.

North Carolina

Iconic

I got into music through a public speaking class. I performed a Frank Ocean song and Kendrick Lamar’s Mortal Man, merged together, in front of everybody, and afterwards I thought I’d give this a good old college try.

Timothy had been doing music for years already. We started a group with three friends and called it Iconic. Hoodies, apparel, logos, hats. House parties and shows all over Wilmington.

We even grew to the point where an agency signed me and put on a show in Washington, DC. Me and Timothy went up together and performed, stayed at my Gigi’s, and came back. That was maybe three years of it. Nonstop creativity and motion.

Doing what you love, with who you love, requires sacrifice.

North Carolina

Just keep pushin’

I got a job pushing patients through New Hanover Regional. I was the youngest on the crew, so I got the large patients and the complicated beds.

Ten thousand steps a shift, easily. I was strong and I was a hard worker, but it was a lot.

People told me their regrets whether I asked or not, I think because I was visibly young. Rooms full of people who love somebody. Rooms with nobody in them at all.

One woman stays with me. She and her husband had sold everything, moved onto a boat, and gone around the world. She was dying when I met her, but she was grateful.

Death can be a visitor, not an intruder.

Her advice was to roll my clothes. Life is short, life is fast, things don’t mean as much as you do, so roll them, stuff them in a bag and go have some fun. I already knew how from a sea bag in ROTC. I still roll clothes every time I pack.

People say everybody should do a stint in the military or in customer service. If you can get inside healthcare young, I believe it goes further and shows you more about life than the alternatives.

North Carolina

Well that’s convenient

My grandparents handed me a point-and-shoot five years before I did anything serious with it. When Timothy stayed in music and I wanted something of my own, it was already sitting there.

I shot a video for the hospital from a barber’s chair. No crew and no budget. It ran for a free community health day, blood pressure checks and flu shots that cost nobody anything. That one video started a company.

Then they made me choose. Come on staff or be our vendor, not both. I picked the camera. That meant putting down music and a full-time job, and what I actually put down was predictability. Weeks later I was back in their buildings with a camera and an invoice.

I called it Blue Roll. Four years, maybe twenty public events a year, and for most of the time at the beginning the whole crew was just me.

Noah shot the stills and owned leading photography. Austen shot with me too, as a friend rather than crew. Eventually we went on to have at least half a dozen creatives on every job.

Working with creative people is about feeling more than process.

We started a podcast as well, to have more opportunities to capture content. Business owners, the people throwing the events, nonprofit leaders, local politicians. And the best part? People wanted to share their stories.

North Carolina

Community work

Not all of it was for a brand. A swim program in Northside gave lessons away, because the color of a person’s skin should never stand between them and learning to swim.

A hospital campaign I made was about interpreters, for patients who needed translation and didn’t know they were allowed to ask for one. In 2018, after Florence, I spent a day handing out hot meals in neighborhoods the trucks couldn’t reach.

In 2020 there was no work left in my own business, so I filmed a food drive instead. Out of everything from those years, that’s the one I’d keep. Giving my time isn’t what I do when the work runs out. It’s what I do.

Emmanuel, a former mentor of mine, invited me back to UNCW to speak at the Upperman Center, on the same bill as Big B. I was on the bill and behind the camera at the same time.

I helped found the Northside Food Co-Op with Cedric Harrison, who runs Support The Port. That one I wasn’t filming. I was in the room that started it.

In October 2019 I was in the inaugural 40 Under 40 class in Wilmington. A rising stars list the year after, and a Coastal Entrepreneur Award in film in 2021.

North Carolina · leaving, and coming back

The silence before the storm

An in-person video business during a pandemic stops being a business. The work stopped and I was holding a degree I’d never really used.

Closing Blue Roll was slow.

There was never an announcement. I shut it down in the quietest way possible, and it just faded out.

It felt like I failed. I’d built something that looked successful and collected the awards for it, but then nobody would hire me for the things I’d done. Four years of running your own company reads to a hiring manager as a flight risk.

The hardest part wasn’t the company. It was not getting to spend that time with the friends and family who were in it, and not being in rooms I’d given four years to. It was hard to let it go.

I eventually joined a non-profit organization focused on DEI. I’ve gone on to serve startups, marketing agencies and enterprise organizations, while still holding it down for the underground.

North Carolina

A place to think

Wilmington is the first place that ever stayed. I left it twice and came back twice, and the second time nobody moved me. I came back for my family.

There’s a lift bridge over the Cape Fear that I went to for years, and a beach down at Fort Fisher. Not to solve anything. I went for the quiet, and I think it’s the only part of those years where I wasn’t making something.

That’s quite a long drive

I moved to Oakland in June 2025. I’d looked at North Carolina, Tennessee and Texas. I’d always wanted California, but I’d never once thought about the Bay.

I knew nobody in this city.

On my second day I went to Off the Grid at the Oakland Museum. Not an office and not an apartment viewing. I’d spent a childhood sitting outside buildings I wasn’t going into, and the first thing I did here was walk into one to look at things.

Oakland

Believe in magic

I chose this city for what people had made in it. Not for the job, which I already had, and not for the weather. I think I had a sneaking suspicion about the Bay before I had a reason.

There’s a place in Oakland called Fairyland, and it’s what gave Walt Disney the idea for Disneyland. You could see it from the office and you can walk to it. That was the linchpin of the week I was having.

I have a lot of respect for a person who builds the thing he imagined, and being in walking distance of the one that started it was the sign I needed.

Pixar is over in Emeryville. The cranes in the shipyards here are where Lucasfilm got the walkers. Tupac came out of this place. The Black Panther Party was founded here, which was a big thing for me. And Lake Merritt was just fantastic.

What I do now is help people use AI at work. Executives, VPs, individual contributors, rev ops, sales, accountants, lawyers. Everybody arrives with the same shape of question. Here’s a problem I have, and I wish it were better.

There isn’t one moment in it. There are thousands, and I think what they taught me is that this is habit, behavior, change management, and getting people to adopt a new way of working even when the old way isn’t wrong.

AI adoption is much more of a human issue than a technology issue.

I was raised by my father to leave things better than I found them. If somebody reaches out for help I’m going to help them, even at my own expense. I’ve had to get better at boundaries as I’ve gotten older.

Nobody asked me to step up and serve an entire company for AI enablement. I did it myself. Eventually there was enough work on top of the job Great Place To Work hired me for, paid media and marketing operations, that I took a proposal to the executive team and it became the job.

I spent four years being paid to make content, take photographs and create videos. Thinking about lighting, sets, backgrounds, lens choice, color theory. All so an algorithm could make a picture for a fraction of the price and the energy. What a life we’ve come to live.

Oakland

Six hours and a layover

There’s no direct flight from here to Wilmington. Charlotte, or New York, or Colorado, and it’s five hundred dollars before you’ve thought about the dog. Probably more by now.

I can’t get up and go the way I once could. Nobody in this family can. That just took some getting used to.

So we call instead. We FaceTime, we text more than we used to, and everybody picks up. My grandparents came out and we drove up to the redwoods, and stood at the foot of a tree that was older than every town I’ve ever lived in.

Panda made the whole trip with me. Jacksonville, then Wilmington, and now three thousand miles from the neighborhood she was born in. She’s got just as much energy and love as the day I met her.

Distance makes the heart grow fonder.

Oakland

The long way home

Turns out my family got to the town a long time before I did.

Life certainly has a sense of poetry - if you’re willing to listen.