Art Harrison: Work, Life and Starting Over

Art Harrison
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I'm Art Harrison. I've started businesses, sold one, made some expensive mistakes, and found plenty of ways to get in my own way. These are short, true stories about work, money, ambition, relationships, and starting over. I talk about what happened, what I thought I was doing, and what I make of it now. Sometimes there's something useful in the gap. For anyone building something, changing direction, or trying to work out what they actually want from the life they're working so hard to build.

  1. 21h ago

    I Accidentally Erased a Year's Work on My First Business

    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 --- 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

  2. 2d ago

    The Best Thing I Got From My First Startup Pitch Wasn't a Yes

    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 --- 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

  3. 4d ago

    I've Built Companies and I Still Ask AI If My Ideas Are Good

    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 --- 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

  4. 6d ago

    A Famous Song Might Be About My Dad and I Refuse to Find Out

    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 --- 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

  5. Oct 20

    Find Out Who's All Talk Before It Costs You Ten Years

    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 --- 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

  6. Oct 18

    Copying The People You Admire Is What's Between You And It Finally Working

    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 --- 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

  7. Oct 16

    Why I Dread Being Asked What I Do Outside Work

    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 --- 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

  8. Oct 14

    I Created a Hate Group as a Joke Then Harvard Called

    At seventeen, I turned a joke about my mixed-race family into a website for a fake hate group. It was satire, but not everybody got the joke. Then I got an invitation I thought must be fake too. I didn't have a business plan. I had a ridiculous idea I wanted to keep going with. That took me to a conference at Harvard and, eventually, into building an online community. I want to tell you how that happened, because it wasn't the last time I started something this way. 00:00 Standing on a chair at Harvard 01:01 A joke with my sister 01:33 The satirical website I made at seventeen 02:14 Hate mail and an unexpected invitation 03:11 Taking the idea further at the conference 04:00 The community became a business 04:48 Committing to an idea 05:30 What if you did something with that joke? --- 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

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About

I'm Art Harrison. I've started businesses, sold one, made some expensive mistakes, and found plenty of ways to get in my own way. These are short, true stories about work, money, ambition, relationships, and starting over. I talk about what happened, what I thought I was doing, and what I make of it now. Sometimes there's something useful in the gap. For anyone building something, changing direction, or trying to work out what they actually want from the life they're working so hard to build.

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