Starting a business is hard

Starting a business of your own is hard.

I'm on my second business now: Purely Political Consulting. Despite the fact that it's just me, it is a business.  I have real clients, and I have real deliverables.  And the important part: I have to make enough money to pay the mortgage.

My first business attempt was more ambitious. A buddy of mine and I put together an investment group to purchase alternative newspapers in 2002.  Amazingly, we put together the money pretty easily.  The hard part was finding a property that wanted to sell.  Only six years ago most alts still had 25% margins.  Now it seems everyone wants to sell. (My buddy later started another business of his own too.)

I've had the "newspaper" bug since I was in high school. But when I got to college and became editor of my school's small student weekly, I found that I was more interested in making the paper financially viable than I was in rooting out the hidden stories on campus.  That was fine, since we increased readership to other campuses and cleaned up the paper's books.

After my first business attempt came to a close, I did some business consulting for a small group of suburban and ex-urban dailies. There, I came face-to-face with the entrenched business conservatism of the newspaper industry: If some other newspaper isn't doing it, then we don't want to do it. And this was in 2003. And their classified revenue was already falling through the floor. You'd think it was time to change some things up, right?

It drove me nuts, and I ended up heading back to Chicago and back into politics.

The bug stayed with me.  I wrote a bit for Chicagoist.com and developed a new business plan for a publication. I've been tweaking it and shopping it around for the right investor.

And then I went to Ken Davis' Chicago Journalism Town Hall. Listening to the conversation, everyone knew changes were coming to news media, but they weren't sure how to find it. It seemed to me that this would be the perfect opportunity for an aspiring entrepreneur.

And this would be hard.

So when Scott Smith, Barbara Iverson and I talked about a follow up conference, we all agreed that it had to be centered on how to make money selling the news.  Not necessarily "rich", but well enough to pay the mortgage.

And starting a business of your own is hard.  So we're going to have people who've done that to talk about it.

If you're thinking about taking the leap, please come out to the Chicago Media Future Conference on Saturday, June 13.  You'll be in good company.