
Jay Shaw walks through his early hustles: selling wallet photos as a kid, flipping penny candy from Costco, burning and selling mixtape CDs, fixing computers, teaching piano, then starting a repair shop and cleaning company before moving into coaching.
Chapters
So I want to know about y'all's childhood entrepreneurial escapades. At what age did you realize that you can exchange products and services for money, and what did you do with that information when you discovered that? I'm gonna tell you mine, just stick around a little bit, but I do want to know yours. All right, so watch mine, but when you're done watching mine, tell me about yours. So I can remember being about maybe 4 or 5 years old. My mom was a beautician, she did hair at the crib, and she had an Easter picture of me hanging up in the living room, and people would always come in how handsome I was and how much they liked the picture. One day I was in my mama room going through her shit and I found the wallet sizes of the pictures in her room. I got those chopped up and I just always kept them in reach. And every time somebody commented on how cute that picture was, how adorable I was, how handsome I was, I go get them wallet sizes. Like, yo, you, you can have one for $3. That— and they were women. I was a kid. They were nice. They would sometimes, they would give me $10. One lady gave me $20 and that woke up something in me like, wait a minute. Wait a minute, I can— people will give me money in exchange for stuff. Okay, so that continued probably around 4th grade, 5th grade. I started selling candy at school. I would go— it was a candy store right by the bus stop. Every morning I run that candy store with like $5 or $10, so if I can get my hand on— by the time we got to the playground, you had to know that $5 was gonna flip to about $20 because we— I was buying penny candy. from the candy lady. Then I would take the penny candy to school, sell it. But then my grandma started like, um, restocking the stuff at our church, so she started going to Sam's. Then I found out about Sam's Club and Costco, and it was game over for them, boy. I started taking that $5 and $10 I was taking to the candy store, spending that at Sam's. Now I'm getting it at cost, boy. We ran it up a bag there. I started selling string. Y'all remember the string? Like you go over, over, under, under, make them keychains, and you pull them over, over, under, under. I used to sell that. Um, around 6th grade, MP3 players started coming out. Now, before the MP3 players, I used to make CDs for people. All the dudes who used to rap, I used to put the hottest instrumentals— I'll put those on the CD, sell the CDs with the instrumentals. A little bit after that, MP3 players, iPods started getting popular. So I charged people $15, I come home with a whole bunch of MP3 players, iPods loaded up with whatever. I wouldn't even ask them what they want. You was getting what I was listening to, but Everybody didn't have a computer, everybody didn't have access, everybody knew how to get the music, so they was cool with that. But messing around with line wire and frost wire, I broke our computer. This is back in the day when the whole house had one computer. I broke our computer and my mom was about to beat my ass. I had to figure out how to fix it, so I learned how to remove viruses, then I learned how to repair screens. So by the time I'm in junior high, I got a whole little computer repair little hustle going. Then I forgot to mention, I started playing piano when I was like in the 2nd grade. So by the time I'm junior high freshman year, I'm starting to get— I'm starting to get cold with these. Got me 3 or 4 churches in rotation. I'm playing at weddings. I got my music like little hustle going on. Um, it's just always been some type of hustle. I'm missing something. So we did the CDs, we talked about the MP3 players, then we started doing the computer repair. Then I started playing piano and doing that, started teaching lessons. And then, yeah, I guess around that time I was coming out of high school and really starting to start businesses. So my first, like, official business was a computer repair business, but then computers started getting so cheap that it was hard to charge what I wanted to charge to really make it. Then the cleaning company, and then I Coach Bosses and everything I do today. Yeah, that was my childhood entrepreneurial adventure. I want to know yours.










