[laujen]

I'm in Portland, Oregon, and think this is actually the biggest problem with our start-up culture. There just aren't enough people who have been there/done that before that are investing in the next generation. There are investors around and the government has stepped in to fund some investment groups to bridge the gap, but until we have a round of winners really supporting the next round of companies I think our community will struggle.

[colinyoung]

In Chicago, where I'm located, this is our core problem too. It's all about that first round of winners. I think startup scenes really launch after the employees from the first big win sell _their_ companies.

[laujen]

We actually had some winners in the 90s but many of them either lost their winnings in the dot bomb or never invested in other companies. A few of those winners are guiding their second or third start-ups, too.

[colinyoung]

Definitely. The main reason they didn't reinvest was timing -- everyone was burnt out on startups even if they had won after the dot.com burst.

But now, FB or Google employees are like, wow, that was awesome, let's do it again. I think the startup scene is more mature now and that reinvestment is more likely to happen outside of SV now -- the key difference is that startups are more stable, wiser, far leaner, and more `cool' now, so it's seen as an actually "safe" bet to re-invest. I know if I ever had a win that's exactly what I would do, in fact being able to re-invest is a lot of my motivation for being a founder.

[asanwal]

The data for Illinois is already looking up based on VC activity. The Halo Effect that Groupon will enable should be a good thing for Chicago. Look at page 15 of this report which shows an uptick for Illinois - http://bit.ly/hdL5Yz. Of course, 2 quarters doesn't make a long-term trend but it's a start so hopefully lots of good things will emerge from Chicago and the virtuous cycle will start.

[luminary]

This is quite true. My Portland State advisor (ex-Bay Areaite) and his friends and angle investing everywhere but Portland.

On a side note: any Bay Area Portlanders on HN?

[laujen]

That's a shame because there is some really interesting stuff happening around town.