random thought: you should throw out any piece of postal mail that says “open immediately. Contains time-sensitive documents.”

if you really want to get someone to read your mail, the envelop should say something like:
“do not read. this is not important enough for you. throw in the trash immediately.”
— i bet that letter would have a 90% rate of being read…

I did my first two start-ups when I was 7 and 8. One was an economic failure. The second was an ethical failure.

When I was seven, I launched a lemonade stand. Auren’s Lemonade was a big hit with the neighbors. I set up the stand in the corner of the street and it sold like hot-cakes. I was rich. At least I felt rich. I probably only made a few dollars after a long day, but I felt really wealthy.

The next week, it was really hot out … so I decided to do lemonade sequel. But this time my dad charged my for the lemonade can (the Tropicana frozen kind), the plastic cups, the ice, the poster-board for the sign, and made me rent the table and chair for the stand. Luckily he did not ask me to pay parent taxes.

Needless to say, I lost a lot of money that day and Auren’s Lemonade officially filed for bankruptcy. But it was problem the best lesson I ever learned.

The next year, my friend Blaine and I decided that we were going to become multimillionaires selling cigarettes to kids. This was the unethical business. We figured that neighborhood kids would gladly pay $0.25 for a cigarette so we only had to sell 4,000,000 of them to become the first kid business tycoons. We had already decided what car we would buy our parents. We were eight years old going on Rikers Island.

Beside for the problem of selling toxins to other kids (for some reason, this did not bother us at all), there was the big issue that we did not have access to cigarettes. And even if we could buy them, they were expensive and would really cut into our margins.

So Blaine has the brilliant idea of collecting cigarette butts on the ground (there were thousands of them in the park) and then manufacturing new cigarettes. We gathered our product, created an assembly line of white paper, scissors, shredded dried leaves, and scotch tape. Soon we had a few hundred cigarettes and were hawking our wares to all the other kids. And for the first time in my life, I was really popular. No wonder people become drug dealers.

All was peachy until one of our customer’s parents called up Blaine’s dad. We were in big trouble. We were forced to destroy our entire supply, and write apology notes and reimburse all the kids. And I think I was grounded for nine months.

I learned my lesson.

Glad it happened to me when I was eight … otherwise I might have grown up to be Andy Fastow.

I made my first $1000 in eighth grade selling baseball cards.

I seventh grade I decided I was going to start a business selling baseball cards. The problem was, I didn’t yet know anything about baseball. So I started learning everything I could. Luckily, it is a sport with a lot of statistics and perfect for a math geek like me.

In shop class I made a rubber stamp to stamp out my business cards (I used to cut up small index cards). It said:

A. Baseball
[street address]
Mamaroneck, NY 10543
914-381-xxxx

So I set about buying low and selling high. At the time (1987), baseball cards were an extremely inefficient market and there was a bit of a bubble going on.

I used to buy an eight foot table at the local baseball card show. Prices were initially $150 for the table. I split the table with my friend Alex — each taking 4 feet for $75. And sold a lot of baseball cards.

But I quickly realized that the organizer of the baseball card show was giving all the favorable floor spots to his buddies and we were stuck in the bleachers (sometimes literally — as these shows were often done on a Saturday in a high school gym). So while I might make $200, after paying for the table, price tags, card holders, and the cards themselves, I wasn’t making much money. Especially not when considering my time (though my alternative at the time was making $3.75/hour minimum wage job).

So instead of selling baseball cards, I tried to entertain people.
First, I noticed a lot of cards were mis-priced. If you got a 1984 Topps Don Mattingly Rookie card, it might list for $32 but it rarely sold for $20. and you could buy a near-mint condition card for $10. and dealers were stuck with thousands of these cards that hard a hard time selling for their full “value.” (of course, today prices have fallen by more than a third)

So I acquired a ton of these cards and created a grab bag. For the first show I created 150 grab bags with cards in them where the person who picks the bags could win the cool cards. Each grab bag (actually an envelop stuffed with cards) cost a dollar. I sold out in 45 minutes. The next show I had 300. sold out. I soon was selling over 400 a show.

Then I had copycats at the shows … so I added fortunes and other fun stuff in the grab bags. Everyone had to buy at least one.

And then I created a dice game. Cost $0.50 to roll dice and depending on what you rolled, you won something. If you rolled doubles you had the option of taking your card or rolling again. It was fun. And you never could sell out. After about a dozen shows I finally made $1000 in a show. I felt really rich. But more importantly … I felt empowered. The average age of the sellers at the show was about 40. I was 14. and they were coming to me asking for advice.

I’m a big believer that more kids should try to be entrepreneurs. It is really empowering. For me personally, I went from being a relatively shy kid to one with extreme confidence (maybe too much confidence).

for other bloggers out there (like Chris Yeh, Mark Pincus, Hunter Walk, Andy Choy, Ben Casnocha, Noah Kagan, Christine Herron, Pete Caputa, Dave McClure, Fabrice Grinda, Keith Teare, Chris Alden, Jeremy Dann, Bambi Francisco, Barney Pell, Andrew Boer, Aydin Senkut, James Hong, Jeff Clavier, Niall Kennedy, Zaw Thet, Pascal Levensohn, Angie Schiavoni, Sonia Arrison, etc.), I’d be interested in hearing your stories of how you made your first $1000.

I used to clean houses when I was in high school.

In high school, I ran a little company called H+M Services that did household chores. I’d employ my high school friends for many of the jobs (I took a 10% fee of what they made) and I took the really high paying jobs for myself. Those were often the housecleaning and lawn-mowing jobs (they pay really well).

When is was 16, I cleaned one guy’s house in Harrison NY. He had a condo and he was a really nice guy. He bought and sold Hollywood scripts and gave me a lot of business advice. He trusted me … gave me the keys to his home, and would usually leave a $20 tip — big money for a high school student.

One day I was his condo cleaning while I was tossing one of his paperweights in the air and catching it. Then … all of a sudden … I missed the paperweight and it went crashing through the dry-wall. I was shocked. There was a big hole in the wall.

Rather than leaving a note for the owner telling him what I had done (this was before the ubiquity of cell phones and email), I rearranged his furniture to cover up the hole thinking he might not notice. When he called me later that night asking for an explanation, I pretended that I did not see the hole and that it must have already been there. It was a horribly lame lie.

While I did not lose the customer, he never trusted me anymore. And I never got the tip anymore. And I never got the business advice or career help. I devolved to hired help … that was all.

This is one of the many incidents that I regret. If I had to do it all over again, I wish I had left a note, left the money from that job, and proactively calling the homeowner to see if I can help more.