Guest Post: Josh Kopelman advises DreamIt companies to fail early and often

Editor’s Note: Technically Phily is often unable to make it to local events, so we’ve begun reaching out to readers who would like to write a guest post about an event they attended to ensure that, despite our schedules, more events can receive the coverage they deserve. This the first of such posts. If you’d like to write about an event you are attending, drop us a line.
This is a guest event post by Chris DiFonzo.  Chris is actively involved with multiple startups, as CRO of newly formed VidaView Technology Group and Co-Founder and CEO of OpenDesks.com. He is friendly with the folks at First Round.
Tuesday night’s DreamIt 2010 Speaker Series event at the University City Science Center featured an engaging, Powerpoint-free conversation with Josh Kopelman of First Round Capital.
The 90-minute discussion revolved around gathering feedback, making adjustments, and approaching startup challenges deliberately. Kopelman set the tone early: “One thing I know about all of your business plans, is they’re all wrong.”

By way of example, Kopelman pointed to Invite Media – another Philly startup success story, acquired by Google on June 3rd – who started as an algorithms company and through decisive, timely “pivots” evolved into an ad-buying dashboard. As an entrepreneur, he asked, do you pivot and adjust, or do you aim and stay steadfast on target?
“One of the things we look for when interviewing entrepreneurs is an ability to collect and analyze data,” said Kopelman.
Discussion around these disciplines consumed a good portion of the evening – looking at seed stage businesses as a series of experiments designed to validate, de-risk, and disprove assumptions and hypotheses; identifying the two or three inflection points that produce massive enterprise value or decrease risk disproportionately; and surfacing and understanding unknowns.
Kopelman gave straight, candid advice: “Not all risks are created equal. You’re only here for the summer – you can’t validate 30 assumptions. What are the risks, variables, and unknowns that matter? What can you do cheaply to figure this out?”
Kopelman also shared some thoughts about making deliberate decisions around company culture, particularly tolerance for risk. Using a basketball metaphor, he talked about “the importance of getting your fouls” – fouling out early is bad, but not fouling at all is equally bad.
Kopelman entertained with insider stories about edgy marketing initiatives conducted by Half.com, some fouls, but all homeruns. Some of the conversation was intimate and off the record – “no tweeting!”
Speaking directly to the DreamIt program participants, Kopelman closed with, “You guys are in the perfect spot, go crazy, as long as it’s ethical.” The talk was the Philly startup ecosystem at its finest – gritty, open, and intimate.
Disclosure: Chris is active in the Philly startup community and friendly with First Round Capital and multiple alumni of the DreamIt program.