Does life become a 90s rap video? Cham’ bustin’ 24/7?

I basically had no money in my twenties.

I was luckier than most, my parents helped with the rent and I had spending cash via the Web design firm I started in 1995, Mischief New Media. My clients were “major” record labels and I designed Web sites for their artists. I wasn’t that great and as soon as the Web started taking off they brought those things in-house. But I had a knack for product development and saw an opening for better uber-music destinations in a landscape that had few good ones. So on the side, I started building music sites I would use. RockOnTV, MusicNewsWire and MusicStation, just to name a few.

I got lucky and five years later sold my company to MTV Networks. All those sites were rolled into SonicNet.com, the biggest music site around at the time. Now all defunct!

All of a sudden, I had some money.

What did I do first?

While in my lawyer’s office I made a copy of the check. Then I found what I thought to be the mailing address of the principal that kicked me out of school before my senior year. I wrote “F*CK YOU” on the check and mailed it. I don’t know if she ever got it. But 11 years after high school graduation, I finally had some closure. Yes, I held a grudge, but now I was over it. It’s a long story of trust, betrayal, power gone mad, evils of authority and not for this post. :-) She represented all the people that didn’t believe in me. Deep breath and now back to the story …

The money. What did I do with the money?

Two things I remember vividly.

First, I called my mom up and said something like this:

Me: It’s done. I just sold the company to MTV.

Mom: Oh, my god! Oh, my god! I’m so proud of you!

Me: Bring every bill, everything you owe over to my place tonight. We’re gonna write some checks.

Mom: Are you serious? (SCREAMING)

Me: Yes, see you later.

So, Mom did just that. And for about an hour that night we wrote checks for credit card bills, rent, school, personal loans … you name it.

Buying things is certainly a lot of fun. Travel, cars, all that big pimpin’ stuff. But at the end of the day, if you can help or give back to those that did the same for you … well, that rocks. It’s a great feeling. More importantly, my mom was directly responsible for my product chops. When I was about 3 years old, she bought me a huge box of building blocks. Simple, made of wood, lots of shapes. There is no doubt in my mind that playing with those blocks shaped my creativity. They made me think about structure, balance, systems and more. She always made sure we had what we needed; she went without and worked hard to provide for us.

To this day, it’s the proudest moment of my life.

The second thing? Well, let me step back here …

When you’re an entrepreneur putting it all on the line, as least with me, I worked constantly. For five years. Eighteen-hour days. Getting out very little. Always thinking about work. Work, work, work. When you have one of these events, like selling, you can go a little crazy for a second. It’s not over, there is more to do to realize the dream. But it’s a moment where you get dizzy for a second. And I sort of reverted back to childhood for a few weeks. How so? I went on eBay and bought what I remember to be thousands of Matchbox cars. Why? Who the f*ck knows. I liked them when I was five years old. My mom used to buy me one a week. It was a good memory from simpler times. Now? I was a man-child with cash and clearly no idea what to do with it.

So, I’m sitting in my apartment and these boxes start coming in. I mean tons of them. Unopened collections of f*cking Matchbox cars. I opened one, took a deep breath and just started laughing. What the hell was I thinking? There was no way I was able to return these. My small apartment was filled with toy cars. What now?

I went out to get something to eat a few days later and I noticed the lobby of my building had these huge bins for a children’s toy drive. I turned around, got the wheely pushcart in the lobby and went back to my apartment. I loaded the boxes of cars up and within a few trips had given all of them away. Mostly unopened. In these digital times, needy kids probably thought … what moron is giving me a miniature car? I want Nintendo DS!

And so goes my few weeks of reverting to childhood nuttiness.

Yes, I ended up getting the car and the home. I’ve bought hundreds of pairs of sneakers that put Quincy Smith’s collection to shame. I’ve traveled to all sorts of great places. I love buying stuff for my nieces and nephew. I’ve pretended to be an angel investor. … And yes, of course, I’ve donated to causes (I’m not totally selfish), mostly having to do with education (see www.cfy.org). But these are the two things I remember most.

So what did you do? Tell your stories …

-JH

Jason Hirschhorn is an entrepreneur most comfortable at the intersection between entertainment and technology. He was formerly CEO of his first venture, Mischief New Media, Chief Digital Officer of MTV Networks, President of Sling Media and most recently Co-President of Myspace. Jason is also an investor in Howcast, Buzz Media, 5 to 1 and other startups. You can follow him on Twitter @JasonHirschhorn or via his widely read Media ReDEFined newsletter (@MediaReDEF or http://feedburner.google.com/fb/a/mailverify?uri=mediaredef)

Other luminaries on the guest list:

• Twitter and Square founder Jack Dorsey
• Howcast CEO and co-founder Jason Liebman
• Clay Shirky, author and New York University professor
• Jared Cohen, Member of Secretary Clinton’s Policy Planning staff
• Andrew Rasiej, founder of Personal Democracy Forum
• Shervin Pishevar, founder of Social Gaming Network
• Tiffany Shlain, founder of the Webby Awards
• Luis Ubiñas, President of the Ford Foundation
• James Eberhard, pioneer of mobile content and services

What’s on the agenda? Dunno. But I imagine we’ll hear a lot of chatter about it during and after the fact. Here’s Dorsey’s self-portrait, taken en route to the event today:

Mr. Keane, 38, was most recently chief marketing officer of CBS Corp.’s (CBS) CBS Interactive, a role he had been transitioning out of since earlier this year. Prior to that, he was a sales-strategy executive at Google Inc. (GOOG) who spearheaded the company’s planning with large advertisers and agencies.

His appointment signals some fresh momentum for the three-year-old Associated Content, which is one of several, including Demand Media and Howcast, that is trying to develop cheaper models for creating and distributing content online.

The company allows users to submit text, video and audio on topics it selects. The submissions tend towards how-to’s and subjects like whether to buy a hybrid car or how to get the best financial advice. The company indexes and distributes the media to other publishers and funnels traffic to it by optimizing it for search engines. It shows ads against the media and gives users and publishers a cut.

In an interview, Mr. Keane said the company’s math-based model appealed to him. “I really do believe that same math and science that has been applied to advertising can be applied to content,” he said. He added that after his stint at CBS, which included the company’s acquisition and integration of CNet, he was looking to get closer to the operations of a business.

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That, at least, is the theme of the grandly named “Alliance of Youth Movements Summit,” which kicks off today at Columbia Law School. The two-day event, organized by video start-up Howcast, is supposed help activists brainstorm ways to use Facebook and other social media to organize themselves and garner attention.

This is heady stuff, but there is some real-world grounding there: Organizers of a protest against FARC, the Columbian terrorists, credit Facebook with helping them rally millions of people against the group in February.

The man who organized that movement, Oscar Morales, will appear at the summit, and so will Facebook co-founder Dustin Moskovitz. I’m also interested to hear from members of the Obama campaign’s Internet team, who will appear Friday. And, um, so will I: I’m moderating a panel of media worthies, including MSNBC’s Luke Russert.

A full schedule is here, and if you can’t make the event in person, you should be able to tune in via Webcast at Howcast’s page.

[Image Credit: equinoXio]