Art Harrison: Work, Life and Starting Over

Getting something started has always excited me more than keeping it running. I can trace that back to being sixteen, when my parents went away with the car keys and I decided that wasn't going to stop me.

The same pattern followed me into bands and businesses. I loved figuring out how to make something happen; I was much less excited when it became routine. It took me a while to understand what that meant for the kind of work I should be doing.

00:00 Excited to start, quick to lose interest

00:57 My parents took the keys

01:48 The copy didn't work

02:27 Driving the car and losing the thrill

02:48 Selling the band was more fun than practice

03:12 Starting a business and then running it

03:42 Different people for different stages

04:48 Why I chose a business of one

05:18 Finding the work that fits

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

Running a social network meant spending my evenings removing porn from other people's uploads. I built tools to get through the work faster, then went back to what I thought was my real business.

I was looking for a good business idea while spending hours on a problem I already understood. This is the content moderation opportunity I missed, and the question I now ask when a task makes me wish I could pay someone to take it away.

00:00 Three years of reviewing uploaded images

00:40 Moderating the social network

00:59 Building tools to get through the work

01:32 What I didn't see

02:17 The work we keep putting off

02:49 Would someone else pay to solve it?

03:49 What do you wish would go away?

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

I knew exactly what kind of boss and father I was going to be: patient, generous with my time, always there when someone needed me. Then there was another deadline, another sales call, another payroll to make.

A lot of those decisions were necessary. That didn't stop them from adding up. This is about the gap between the person I meant to be and the person people actually got, and the few promises I still try to keep when everything needs my attention.

00:00 The father and boss I planned to be

00:36 Having the chance and falling short

01:10 The fifth task that paid the bills

01:48 Just give me ten minutes

02:35 The people I thought I would do better than

03:00 Choose one or two principles

03:48 Being honest with my team and family

04:24 What I want to protect in these videos

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

I'd imagined how it would feel to land a huge business deal. In 2019, I signed a contract worth $500,000 a year to our company while eating alone in a Burger King parking lot. The celebration was smaller than I'd pictured.

I'm still proud of that deal. But by the time it happened, the company had grown and so had everything we needed from it. I think about that lunch whenever a goal finally happens and doesn't feel the way I expected.

00:00 Picking the pickles off my burger

00:22 A $500,000-a-year contract

01:10 The celebration I'd imagined

01:35 Signing it alone in the car

02:06 The goalposts had already moved

02:36 What the money meant to the company

03:16 Enjoying the smaller moments

04:08 When the win doesn't feel how you expected

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

My childhood friend Mike had a better-stocked pantry and better Christmas presents than I did. He was never trying to make me feel bad. I still managed to turn it into a competition he knew nothing about.

Years later, that feeling was still there when I started businesses and took risks. I could say I wanted freedom or a better life for my family, and I did. But some of my ambition was coming from a much younger version of me.

00:00 Who am I still trying to impress?

00:47 My best friend Mike

01:23 The pantry I still remember

01:57 Lying about my Christmas presents

02:45 The younger version of me

03:15 Working with Mike years later

03:46 What I still do with that feeling

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

I have one tattoo and several stories about why I got it. The story I usually tell makes me sound spontaneous. The real one is less flattering.

Between that tattoo and an attempt at stand-up comedy, I've had plenty of chances to learn from failure. I'm not sure I learned what I was supposed to. But I did get very good at telling the stories, and those stories have a lot to do with how I see myself.

00:00 When failure doesn't teach you anything

00:15 The tattoo story I like to tell

01:16 Why I actually got the tattoo

02:13 What our stories make people remember

03:46 The childhood stories I choose

04:22 My first attempt at stand-up

05:20 Finding a story in the failure

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

I kept putting off seeing my friends until I had better news about my life. One of my oldest friends lived ten minutes away, and I still missed four of his annual holiday parties. When I finally went, I was three hours late.

I'd always been willing to bet on myself and start another business. Showing up while I was still figuring things out was harder. That night made me look at what I'd been asking my friendships to wait for.

00:00 Finally walking into Tom's party

00:49 The fifth party and my first appearance

01:08 The friend who kept getting me out the door

02:06 What I put aside when I bet on myself

03:08 Waiting for a better story to tell

04:10 What being there gave me

04:59 The life I actually wanted to build

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

At 22, I lied to get a bank loan and credit cards for my first business. Before long, I was borrowing more just to keep up with the payments.

I don't want to turn that into an inspiring story about being resourceful. I did something I shouldn't have, and I got lucky. The uncomfortable part is how much I still recognize the way I thought back then, even though I've never done it again.

00:00 A story I'm not proud of

01:08 Starting a business at 22

02:15 Getting deeper into debt

03:28 A story I later heard from Kevin Smith

04:02 How lucky I was

04:32 Using those instincts in later work

05:25 What I mean by a different approach

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

I had a box of a thousand business cards and a business that hadn't made any money. Founder and CEO was the title I'd picked for myself.

The box arrived earlier than expected, just before a weekend out with a friend. I still remember handing over the very first card. Looking at it now, I can see why that small piece of paper mattered so much to me.

00:00 The business cards I've kept

00:41 Making up my own title

00:58 The first card I gave away

01:50 The picture we have of an entrepreneur

02:43 Wanting a different way to work

03:20 Finding out whether anyone will pay

03:45 Getting off the sidelines

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison

At fourteen, I tried being a quiet, mysterious bad boy. Years later, I paid sales coaches who wanted me to change the way I'd been winning customers.

The sales advice sounded sensible. It was also almost the opposite of what had got our company far enough to pay for it. I wanted to get better, but I wasn't sure that meant becoming the person they had in mind.

00:00 Trying to become the bad boy

00:52 How long the new personality lasted

01:32 Paying coaches to change our sales approach

02:15 What had already been working for us

02:50 Coming back to my natural way of doing things03:13 Being myself in new situations

03:49 Trying to change how I make videos

04:52 Changing for the better or pretending?

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I'm Art Harrison. I tell stories about work, money, starting businesses, and starting over, usually because something didn't go the way I thought it would.

YouTube: https://www.youtube.com/@TheArtHarrison