Photo: Eric Fettner

It’s a warm summer night in Lincoln Park and Chicago is holding the first Moxie Awards.

mox·ie /ˈmäksē/
noun: Force of character, determinations or nerve.

In recognition and celebration of the tech scene, hundreds of the biggest names in the business are here at Park West. It’s sold out and I have no ticket, but a friend somehow gets my name onto the (iPad-powered) guest list.

Here are my observations and a nod to a few of the winners:

  • Big, yet casual
  • 800 people, some in tuxes, some in flip-flops.
  • The place is packed. It’s standing room only.
  • The bars are crowded (open bars always are, right?) and entrepreneurs and VCs edge past each other, bumping elbows and shoulders. It’s a combination of a big night club and a mini-Oscars.

Presenters and winners are candid in true Chicago form. Mayor Rahm sets the tone and Matt Moog (Built In Chicago) and J.B. Pritzker (New World Ventures) play hosts. Remarks are short, direct and punctuated with the occasional f-bomb. This is, after all, the start-up crowd. These are busy, intelligent, no-nonsense people. But they do occasionally take time out to vote on facial hair: the “Best Beard” award went to Dylan Richard.

Then and now: Investor Attitudes and Boy/Girl Ratios

If this is the new tech bubble, it’s smarter and more gender-neutral. I haven’t seen a Chicago tech party this big since the glory days of 2000, when First Tuesday hosted huge events in giant venues with overflowing swag bags. Investors were eager and inexperienced, looking for any way to get into the game. But tonight, the caliber of money and mentorship is top-shelf. These are experienced pros who make sure things make sense. Times have changed.

  • Mentor of the Year: Troy Henikoff
  • VC of the Year: Paul Lee
  • Best Angel or Seed Investor: Kevin Willer (award accepted by Una Pipic doing a lovely impersonation of Kevin Willer)

Back in 2000 the guy/girl ratio at events was probably 90/10. But tonight it looks more like 70/30. Good news for single male geeks. But there is plenty of evidence, women are still underrepresented.

What you didn’t see

Remember that daily deal site? I think it starts with a G…

You don’t hear much mention of Groupon or its founders. No Andrew, no Eric, no Brad. There’s a slight nod to the royalty of daily deals by Paul Lee (also of LightBank) and also a brief mention by the Mayor, but other than that, the IPO’ed mega-star of the tech scene is conspicuously absent.

You also don’t hear much recognition for the little guys. There are hundreds of lesser-known tech business who form the foundation of the community, but they’re not what the Moxies are about. If they were, the trophy might be shaped like a different chess piece: a pawn.

You can’t please everyone

Ron May wasn’t the only grumpy attendee. When you get 800 people together, you’re going to get a few cynics. Some moan that the entire event is self-congratulatory, favoring the “cool kids” with the largest social followings. Indeed four companies won half of the 20 awards: GiveForward (2), BrightTag (3), CodeAcademy (3), and GrubHub (2).

  • Best Consumer Web Startup: GiveForward
  • Tech Woman of the Year: Desiree Vargas Wrigley, GiveForward
  • Best Bootstrapped Startup: CodeAcademy
  • Best Educational or Recruitment Startup: Code Academy
  • Best Startup Founder / Co-Founders: Neal Sales-Griffin & Mike McGee, Code Academy
  • Startup of the Year: BrightTag
  • Best B2B Startup: BrightTag
  • CTO of the Year: Eric Lunt, BrightTag
  • Breakthrough Digital Company of the Year: GrubHub
  • CEO of the Year: Matt Maloney, GrubHub

But it’s all in how you look at it. Just like the Park West itself, you could say it’s cramped or consider it cozy. Some complain that it’s all just mutual back-slapping by a tight-knit group of insiders. But most people appreciate it as a first-class celebration of some truly great Chicago stories. It takes guts to do what these people have done. The name “Moxie” fits.

Thank you Matt, Maria, J.B. and everyone else at BIC and New World on a job well done. And thanks to Brian and Donna Sue for getting me in.