The second annual Seattle 2.0 Awards were held last night at the Bell Harbor Conference Center on the beautiful downtown Seattle waterfront, and just like last year, the event was a big success.  I was there representing Seattle 2.0 in my capacity as a contributing blogger, and I heard I was one of over 400+ attendees.

What I liked:

Smiles. Does anyone have a better smile in the startup community than Glenn Kelman of Redfin?  He accepted two awards: one personally, for Best Entrepreneur Blog, and one on behalf of Redfin, which won Best Startup.  Glenn gave the keynote last year at the inaugural Seattle 2.0 Awards and although I’ve never met him personally, he appears to be the happiest guy on the planet.  Also: he’s shorter than he looks.

George Bernard Shaw. Speaking of keynotes, Jonathan Sposato of Picnik/Google gave the keynote this year and knocked my socks off.  He’s a really great speaker.  No notes!  He quoted George Bernard Shaw, who [paraphrasing] said that “90% of success is casting”, in keeping with a recurring theme of the night – award recipients making a big deal out of the quality of their supporting team.  I like to think Seattleites are especially nice that way.  Also: Cary Grant is cool.

Poker. My friend Bob Crimmins of iMedExchange hustled everybody by winning the inaugural Poker 2.0 tournament at the S2A awards.  I hope it’s continued next year.  I also hope Bob wins again next year, because everybody loves a champion.  Plus, reading the bitchy tweets of the losers will be hilarious.

Diversity. Unlike last year, when it seemed like Picnik ran away with everything, there was a broad set of winners and nobody could be considered to have swept the field.   I think that’s a good thing.  On the other hand, maybe last year’s Picnik win was prescient, what with Picnik getting acquired by Google for a billion dollars or whatever it was.

Leadership. It’s obvious that Seattle 2.0 is in great hands with the addition of Jennifer Cabala as CEO.  She managed the proceedings very well and obviously put a lot of effort into making the night a success.

What could be improved:

Audio. Multiple complaints of poor audio in the back, and the acoustics in Bell Harbor were a little weird.  The gabfest on the demo floor, which was immediately adjacent to the seating for the awards ceremony, didn’t help.

Demo Partners. Was it just me, or did the lineup of demo providers seem a little thin?  I stay fairly close to the community and I don’t think any of the top 100 companies on the Seattle Startup Index were demoing.

Retrospectives. It would be nice to have a little PowerPoint presentation (did I just write that? Gah!) showing key events in the Seattle startup scene from the past year – major acquisitions, funding announcements, new companies, IPOs (what’s that?), etc.  Also, the “Best Startup” category is sort of like “Best Picture” at the Academy Awards, so it would have been nice to have a slide per company describing what they do.  Maybe video!  Just think how many more awards Redfin might have won had Glenn Kelman delivered a video clip to all the voters extolling the smiley-ness of the Redfin corporate culture.

Loved the night.  Loved reconnecting with friends new and old, and I love the Seattle startup community.  See you at the next event!

Glenn Kelman of Redfin gave a great keynote address at last week’s Seattle 2.0 awards. It started slowly, but built up momentum as it went on and by the end I was thinking that this was one of the better keynotes I’d seen at similar events.

Glenn is obviously a very experienced speaker; over and above that he brings a sense of calm authenticity that really allows him to connect with the audience.

View it here: http://www.seattle20.com/blog/Glenn-Kelman-Opening-Talk-Seattle-2-0-Awards.aspx