Josh Kopelman on ‘the democratization of entrepreneurship’ [video]

Hundreds of entrepreneurs gathered at The Hub Cira Centre for the final Startup Grind Philadelphia of 2014.

Derek Andersen, the founder of Startup Grind flew out from Silicon Valley to attend. First Round Capital Managing Partner Josh Kopelman was the main event. He spoke about his investment philosophy, companies he’s invested in, what he thinks about the Philly tech ecosystem and how it feels to be the richest UberX driver.

“Our investment decision was really simple and similar to a lot of other investment decisions: the founding team,” Kopelman said of the decision to invest in Uber. “Garrett Camp was the cofounder of StumbleUpon, [which] we invested in and was sold to eBay. So we had gotten to know him really well.”

Watch the full video of Kopelman’s presentation below:

Host and Benjamin’s Desk founder Mike Maher dug up some information about the time Kopelman carried a large server to venture capital firm Kleiner Perkins to give his pitch for Infonautics.

“We had to ask to get there an hour early to carry this 80-pound machine because back then there were no data centers,” he said. Just goes to show you how much has changed in the past decade, and how the barriers to entry for building software companies has been drastically lowered with cloud server technology, rapid prototyping software and open source code.

“We are witnessing the democratization of entrepreneurship,” Kopelman said. “Before we touched the customer we had to raise $5 million for Infonautics. Now when someone wants to start a new tech company they pull out their Visa card and their first server bill is only $75.”

At one point Kopelman spoke about how he missed certain opportunities with Twitter, and other now-large companies.

“Venture’s a humbling business, because we’re wrong far more than we’re right,” he said.

Kopelman had worked with Twitter cofounder Ev Williams on one of Williams’ earlier startups, Odeo, but decided to pass on Twitter.

“I have that email hung up over my desk now,” Kopelman said ruefully, mentioning an “anti-portfolio” of near misses that also includes Dropbox and Zynga.

Having been in touch with, and impressed by, Williams and Twitter cofounder Jack Dorsey, Kopelman didn’t miss the chance to be an early investor in Dorsey’s Square.

“Some redeeming quality of having missed the Twitter investment was that we were the second-largest seed investor in Square, which I think is going to disrupt a pretty large industry,” he said.

It’s no secret that Philadelphia entrepreneurs often face a difficult fundraising path. (You can get a sense for that in our recent story on “Github for things” startup Squareknot.)

Kopelman and other investors feel that the biggest risk is fundraising, not technology or marketing. “When we give a startup $500,000 we know that there’s a big gap between that half-a-million and the tens of millions you’ll need before your IPO.”

The ability to tell a compelling narrative, and get your foot in the door to VCs is the first step to getting your product out there. If you can convince a VC to give you money, you can convince customers to use your product.

The crowd at Startup Grind Philadelphia. (Photo by Jason Sherman)