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