I started a business because I wanted more freedom. We raised about $20 million for the company, grew fast, and I ended up blocking out my calendar just to get away from the thing I'd built.

After we sold, I talked to a sales trainer who'd deliberately kept his business small. He wanted time for motorcycle trips, and he'd built his work around that. It made me question how much of the success I'd been chasing I actually wanted to live with.The actor-income and business-failure percentages mentioned in this episode are unverified.

00:00 What I actually want from success

01:08 Chasing the wrong version of success

01:38 Taking $20 million and losing freedom

02:32 When the funding stopped

03:04 What a sales trainer taught me after the sale

03:55 Thinking about what matters to you

05:01 The ordinary things I enjoy

05:51 Choosing the size of life you want

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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 thought I was backing up a year's work on my first business. I erased it instead. I was broke, living in my parents' basement, and trying to decide whether I could face starting again.

What got me back to work was a bit of arithmetic I kept doing about the people who stopped along the way. The '10% rule' in this story was how I talked myself into continuing; those percentages aren't measured odds of success.

00:00 The math I used to keep going

00:49 Erasing a year's work

01:48 The campus job that gave me the idea

02:34 Taking the first step

02:59 Sticking with the work

03:57 The setback and another decision

04:29 Sitting down to rebuild

05:09 Why I kept showing up

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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 first startup pitch was at Y Combinator. I didn't get in. I did get a $700 travel-reimbursement check, and the battered photocopy is still one of my favorite things I own.

I'd applied almost on a whim and managed to treat Paul Graham like tech support. But I chose the first interview slot for a reason. There was something I wanted from that day that didn't depend on getting a yes.

00:00 The $700 check I kept

00:42 Applying without knowing much about YC

01:31 Treating Paul Graham like tech support

02:15 Travel money and my first pitch

02:59 Getting more out of the trip

03:19 Choosing the first interview slot

04:08 The people I stayed in touch with

04:56 Looking beyond the person who can say yes

05:52 What that check reminds me to do

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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 asking ChatGPT, Claude and Gemini whether my business ideas were good. If an answer wasn't enthusiastic enough, I'd rephrase the question. Then I'd take the answer to another AI and ask it to check.

I've built companies, made pitches and taken plenty of risks. I still fall into that reassurance loop when my confidence is low. It's made me look at the difference between getting advice and needing permission to trust my own judgment.

00:00 Confidence and a career of trying things

00:40 Trying to press the call button

01:17 What confidence means to me

01:51 Asking AI whether my idea is good

02:32 Why reassurance does not build my confidence

03:21 Looking for small wins

03:50 Still being scared before I start

04:40 The phone-battery comparison

05:27 Building enough confidence to try

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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 family has a story about my dad, Aretha Franklin and Son of a Preacher Man. I've heard it all my life, and I like it enough that I've never wanted to settle whether it's true.

It's given me a little extra confidence at times when I needed it. What interests me is how quickly I'll question a good thing I believe about myself, while letting the doubts pass without much of an argument.

00:00 The story I don't want to fact-check

00:54 Three generations of Arthur Harrison

01:26 The family connection to Aretha Franklin

02:02 The song my dad heard on the radio

02:36 What the story does for me

03:00 The facts that kept creeping in

04:15 Why I question the good stories first

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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

We'd spent the whole night planning a road trip. At sixteen, I packed my suitcase, took $100 out of the bank and waited on the front steps. Nobody came, and nobody called to say the plan was off.

I still think about that morning when a conversation about a business idea gets exciting. It's easy to enjoy the plan together. I've spent a lot of my life trying to be the person who actually shows up, even when it turns out to be a bad idea.

00:00 Waiting on the front steps

00:37 Planning the Myrtle Beach trip

01:49 Packing my bag and waiting

02:20 Was talking about it enough?

02:54 Why I keep trying things

03:25 What buying a lottery ticket feels like

04:38 Being the person who shows up

05:22 I've still never been to Myrtle Beach

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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 cousin tried to copy something he'd seen me do with my pet fish. By morning, the fish was dead and I was on the floor looking for evidence. He admitted he was responsible, but I still don't know exactly what happened.

That memory comes back when I see someone following a successful person's advice and wondering why it isn't working for them. I've told plenty of stories about things that worked for me. I wouldn't want anyone to copy every part of them.00:00 Finding Redhead in the bowl

00:35 Why I'm calling my cousin Dave

01:32 Looking for evidence in the carpet

02:23 What he'd seen me do

03:10 Why copying doesn't always work

03:53 What I hope you take from my stories

04:32 Using the skills that make you different

05:14 Dave stopped trying to be like me

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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 could stand up and talk about our business for hours. Ask me what I enjoyed outside work, and suddenly I had nothing to say. At a team-building session, I kept checking the time, hoping we wouldn't get around to me.

Everyone seemed to have hobbies, trips and stories I couldn't compete with. I spent a long time wondering whether I was just boring. Eventually, I started questioning what I'd been counting as an interesting life in the first place.

00:00 Waiting for my turn in the circle

00:34 The cofounder with nothing to say

01:04 Giving an answer I cannot remember

01:59 Was it the wrong question?

02:46 What a small story can do

03:47 Remember the moments that stayed with you

04:20 Why I share these stories

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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