So You Sold Your First Company — Now What Should You Buy First?

Matchbox carsMatchbox cars seemed like a good purchase at one point…

Having some money all of a sudden is a weird thing. I’ve always wondered what entrepreneurs do when they hit it. What do they buy, If at all? How do they react to new found ducats? 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 websites for their aritsts. I wasn’t that great and 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, MusicStation just to name a few. 

I got lucky and 5 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 the sudden I had some money.

What did I do first?

While in my lawyer’s office I made a copy of the check. Then 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 had some closure. Yes, I held a grudge but now I was over it. It’s a longer 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…

And the money… what did I do with the money?

2 things I remember vividly.

First, I called my mum up and said something like this…

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

mum: 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.

mum: Are you serious? (SCREAMING)

Me: Yes, see you later.

So, mum 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 mum 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 5 years. 18 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 realise 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 5-years-old. My mum 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 2 things I remember most.

So what did you do? Tell your stories…

-JH

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