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GrubHub.com Walks Home with Briefcase Full of Greens at Freshwater Live

by Brad Spirrison
Staff Writer

As a rainstorm pounded on the University of Chicago Gleacher Center Thursday night, a veritable who's who of regional entrepreneurs and venture capital investors reunited at Freshwater Live. GrubHub.com, a Chicago-based search engine, walked away with the prize for best elevator pitch.

In another indication that the Chicago area Internet economy is experiencing a second wind, approximately 200 better known entrepreneurs and venture capitalists convened at Freshwater Live Thursday evening to share war stories and talk about things to come. The gathering, which included two hours of cocktail-oriented networking with one hour of structured content in between, was organized by Freshwater Venture. Founded earlier this year by Chicago area entrepreneurs Eric Antonow and Keith Schacht, Freshwater is an online directory that tracks the past, present and future of entrepreneurship in Chicago.

Among those in attendance were local dot-com poster children Dick Costolo of Feedburner and Jason Fried of 37Signals. Representing the VC crowd were Bob Geras (LaSalle Investments), Adam Koopersmith (New World Ventures), Steve Miller (Origin Ventures), Mark Glennon (Leo Capital Holdings), Jason Heltzer (Oca Ventures), Connie Capone (JK&B Capital), Tim Landon (Tribune Interactive), Jim Pavlik (Baird Venture Partners) and Bill Elmore (Foundation Capital, which is based in Menlo Park, Calif.)

Of course, Matt McCall of Portage Ventures was there as well. Portage seems to have invested in a cloning company as of late because McCall is everywhere these days.

Other well known entrepreneurs present at Freshwater Live who made hay in the first wave of the Internet boom were Bill Lederer (Art.com), Josh Metnick (AIS, disclosure: Metnick is chairman of Midwest Business Inc., publisher of MidwestBusiness), and Tom Parkinson. For those who pay attention to the local dot-community, it was dizzying to see all the faces of innovators and influencers present.

The program featured flashback business plan presentations from Parkinson, Landon, Howard Tullman (CCC Information Systems, Tullman's presentation was taped previously) and Kevin Malover (Orbitz). A panel comprised of Geras, Miller, McCall and Fried were on hand to the judge the merits of the plans. While the tension of a venture capital presentation was hardly replicated, a few good nuggets of wisdom for aspiring entrepreneurs came out during the presentation.

Says Fried: "Put your money into your product and not into all the fancy business cards."

Says Geras: "Be creative, and constantly evolve to new information as it comes to you."

Landon, who spent much of the eighties and nineties making investments on behalf of the Tribune Company, displayed a business plan he reviewed and eventually funded from a struggling Steve Case. America Online in the early nineties was in a world of hurt, and Case was seeking funding from Tribune Ventures to help keep the company afloat.

"Our $5 million turned into $1.6 billion," Landon said. "Unfortunately they didn't all turn out that way or we (Tribune Company) would be in a different position today."

After the presentations, Freshwater Live fast forwarded to showcase a few of today's most notable emerging entrepreneurs in Chicago. Elevator pitches of no longer than 62 seconds " the amount of time it takes to ride the elevator from the Metropolitan Club to the top of the Sears Tower, were made from Matt Maloney of GrubHub.com, Adam Siegel of Inkling and Karan Goel of PrepMe.

GrubHub.com is a restaurant search engine that just inked a deal with Google Local. The company won the University of Chicago New Venture Challenge in May. Inkling is an online service to create prediction markets. The company has worked with Abbot and O?Reilly Media. PrepMe is a test preparation company that uses a proprietary technology and tutors from Stanford and the University of Chicago to help teenagers with their SATs and standardized tests.

Voting for the elevator pitch was done via text-messaging powered by Vibes Media. GrubHub.com ran way with the prize, which was, allegedly, a suitcase filled with 1000 $1 bills.

It all adds up.