The Printed Blog

I’m what you would call a serial entrepreneur, I suppose.

For me, that means I’ll work to save up some money, then I’ll spend it all trying to get a startup off the ground. Alternately, I might be what you’d call a man with a gambling problem. But let’s not split hairs.

Prior to The Printed Blog, I started two companies. One I raised money for (via angels, < $1,000,000) and it failed. The other I didn’t raise money for and it succeeded (built a product, got customers, and sold the company to our number one competitor).

The one that succeeded was not a financial windfall, but it was nice to have an idea, start a company, build a product, earn revenue, get a team, and then sell the company to our top competitor, all without a penny of outside funding.

Here are some things I learned from my experience at The Printed Blog:

1) If you have a compelling vision for the future (not necessarily for a business), you can get incredibly talented people to work for free. Post an ad on Craigslist. It’s far easier to sell a vision of the future, than the reality of the present.

2) If you have a good idea, don’t let yourself get pulled away from it: Stay focused! This was probably the biggest single lesson that I learned too late, and if I had realized it, we may not be shutting down.

I recall the day I conceived The Printed Blog. It was last year, and I was working on two other startups, both of which required online advertising to be successful. I remember thinking that it was going to be a really long, hard road to build tools for online advertisers, and then to sell the ads. I wanted to do something that I thought would generate revenue quickly.

It occurred to me that I could: 1) get blogs for free, 2) get photographs for free, 3) layout a paper in PowerPoint or Word (I’m not a designer, but I get the gist of it), 4) go into a neighborhood myself, go door to door, and sell ads for cash, 5) Xerox the whole thing at Kinkos, and 6) hand it out myself at a train station.

The fact is, if I had done that, I very well might have been able to sell enough ads to make that one issue profitable (I’m 100% certain I could have). Then, I could have added another neighborhood, and another, and so on.

Why didn’t I do that?

Well, I got distracted by all of the press we received. Once we were in The New York Times, and I was getting interview requests from radio and TV and newspapers all over the world, I started to think that I could build the newspaper for the next 100
years.

Instead of focusing on one thing – revenue – on a small enough scale to prove our model, I decided to try and publish the paper in Chicago, San Francisco, New York, and Los Angeles… I got carried away, and we spread ourselves too thin too fast.

So stay FOCUSED! Prove your model incrementally… and if you happen upon something that gets people excited, be very careful.

3) Don’t write a long business plan. Write a good summary, have a good presentation, and have a good revenue / business model. Know what you’re going to do (yourself), but don’t sweat over a great business plan. I suppose this might only be true for really early stage startups, which is what I’m familiar with. Anyone can meet with a good venture capital firm. If you’re right for them, they’ll accept your e-mail. If you’re wrong for them, you don’t want the meeting anyway. Everyone has a phone number… call and ask for them.

4) If you think you can get revenue, do it. I told everyone we should focus on having a great product, i.e. really beautiful issues of The Printed Blog, and everything else would fall in line. This was not the case. While we did get a lot of press, and a lot of people interested in our publication, at the end of the day attention is only icing on the cake.

The cake is revenue… and if I had focused on an okay-looking, black and white Xerox’ed version of The Printed Blog and made sure it was filled with advertisers, chances are I’d be in much a better place today, and probably funded.

5) If you’re looking for money from a venture capitalist, make sure you have a venture capitalist DEAL. I couldn’t convince a single VC that The Printed Blog would make them billions of dollars. I think they understand two things: 1) Virtually none of their investments will return a billion dollars, and 2) If they aren’t as totally certain as they can be, if they haven’t totally convinced themselves that it’s possible, then forget it. They need to “see it.” Your pitch needs to be fiction-less (the fewer people involved in revenue generation, the better), and scalable – you better be able to get large, and fast.

The Printed Blog could be very successful and net $25 million dollars a year. And that would make for a very good business, but is there a liquidity event for it? Is the Tribune Corp. going to buy it? We’d better put the bankruptcy judge on our Board.

Side note: I’m not entirely convinced Sam Zell really exists… I think he’s a Jim Henson puppet designed to exact revenue from a group of bankers who did bad things in their past lives.

6) Finally, the most important thing you have is time. Make sure you spend it on the right things every day. What are the right things? You’ll know soon enough if you’re not spending your time on them.