Transaparency, Markets, and The Internet (continued)

In the venture business, you invest in companies, work closely with them, and at some point move on either because they were sold (or went bust) or they went public and you sold the stock. But you always keep a piece of the company in you. My former partner Milton always liked to hold on to a small portion of his public holdings just for that reason. I don’t do that, but maybe I should.

The reason for that little peek into the emotional makeup of this VC, is that I read with interest about a deal that TheStreet.com did with Stockpickr the other day. I was Chairman of TheStreet.com for a number of years in the late 90s and early part of this decade. And although I’ve been off the board for years and don’t own any stock, I still have an affinity for the Company. I learned a lot from that investment, much of which colors the investments we make now.

And my approach to blogging is very much a reflection of what I learned from watching Jim Cramer do it. He was the first blogger I ever met. He had a code name for his wife and I copied that. He posted regularly and always with an opinion. I try to do that. He wrote like he was talking directly to you. And I try to do that too.

I wrote a long post in the middle of last year about Transparency, Markets, and The Internet where I laid out my history investing in the intersection of the web and finacial markets. And I continue to think there are fantastic opportunities in this sector. We have one company in our portfolio that is utilizing "web 2.0" technologies to deliver investing insights to stock market investors. That company is Instant Information and they focus on the professional investor sector of the market.

We’ve also looked at a number of companies focused on the "DIY" sector of the market – the stock trading enthusiasts. My friend Howard has started Wallstrip to entertain and educate investors on stocks that are on interesting trend lines (mostly all time highs). I’ve been helping him with that startup and have a small personal stake in Wallstrip. Here’s yesterday’s show where Lindsay went out to the streets to get trends for 2007.

But back to Stockpickr, I had not seen the service until I saw the story about TheStreet.com and Stockpickr getting together on TechCrunch the other day. So I spent some time on Stockpickr this morning and I’ve set up a profile page and a fake portfolio. I’ve been waiting for someone to marry social networking and stock picking. It’s a natural. I want to find people who have similar investing interests to mine. I want to see what other people own. I really like that Stockpickr is tracking hedge fund and big name investor’s portfolios as well as the do it yourself crowd. But the one thing that bothers me is that these portfolios may not be real. How do we know that I really own these stocks? In fact I don’t.

So I am not yet sold on Stockpickr. But I am going to play around some more. Someone is going to do last.fm for stocks right and when they do, it’s going to be big.