"When I started half.com, our three biggest competitors were Borders, Tower Records and Blockbuster Video," he told me the other day in an interview at his University City office. "All three are out of business today. It's amazing. They were all billion-dollar chains, worldwide brands, and all three of them got disrupted by technology."
The knockout punches eventually were delivered by others.
Today, the venture capitalist, who dubs himself "Redeye VC," travels from University City - where First Round moved its headquarters last summer - to New York and San Francisco to get early looks at next-generation Web startups.
First Round is invested in 144 startups (an additional 22 have exited), according to its website, but few are in Philly. In the last five years, companies now worth $1 billion that started here have moved on.
"When they left, all that market value left with them," Kopelman said. Invite Media, in which First Round invested, was started here in 2007 but now calls New York home. (It was sold to Google for $100 million in 2010.)
"The founders have gone on to angel-invest in 40 startups, but they're doing it in New York," Kopelman said. "So I don't think Philadelphia's challenge is in coming up with great ideas or having great founders. I think the real challenge is keeping them here."
It's good that Kopelman is thinking about this. Forbes ranked him sixth on its 2012 "Midas List" of Top 100 tech entrepreneurs, the VCs who Forbes believes are creating the most-innovative tech companies.
On Tuesday, Kopelman joined Mayor Nutter at City Hall to announce that First Round would manage, for no fee, a city-sponsored, startup-seed fund and would invest $3 million - matching $3 million invested by the city - over the next three years. Funded companies agree to stay for 18 to 24 months.
In Menlo Park, Calif., he said, one can find more than 250 venture-capital firms on one street managing more than $50 billion.
"And it's not an accident that they're all together," he said. "If you're an entrepreneur and you have a choice to go to a place where there are 250 VC firms or somewhere else where there might be one or two, you're gonna go where all the money is.
"It creates this network effect: The more venture firms, the more entrepreneurs, and vice versa."
On Twitter: @MHinkelman