When Technically Philly pops into his office, the normally cheery venture capitalist is busy trying to figure out why First Round Capital’s email service is down.

“They say six minutes of downtime,” he says. “but they’re way over that.”

After a brief phone conversation (he would later blog about the downtime) he immediately returns to his normal upbeat demeanor and for good reason: Kopelman is one of four founding partners of one of the most active early-stage investment companies in the country. The firm has become as much of a brand as the companies it invests in, boasting the most-visited VC site on the web.

Located in a small, nondescript office building in West Conshohocken, the firm has expanded to San Francisco and will open its New York City offices next week, giving it a headquarters in two of the largest technology communities. The firm is setting a new standard in investment by making a high number of smaller, early stage investments while nurturing companies from the ground up.

First Round, however, is just the latest chapter in the Wharton grad’s career. Kopelman, a New York native, started Internet information company Infonautics while still in college and almost didn’t stay in Philadelphia.

“Once you have 17 people in the company with mortgages and me without, that pressured me to stay,” he says, “Then I grew attached to the area, built networks and planted some roots here and started Half.com.”

Since then, Philly has treated him well: Kopelman and his partners sold Half.com to eBay for $350 million in 2000, giving Philadelphia one its biggest tech “wins” in the Web 1.0 times. After starting and selling Turntide to Symantec in less than a year, Kopelman switched from entrepreneur to investor, making Philadelphia home to one of the most influential Internet investment firms in the world.

We sat down with Kopelman to talk about his take on Philadelphia, what kinds of companies he looks for and why Philly (and every other city) has no comparison.

As always edited for length and clarity. To read the complete interview transcript which includes three times as many questions, follow this link.

What would it take to have First Round located in Philadelphia as opposed to West Conshohocken?

My sense is that I don’t think we’ve lost any deals in the city because we weren’t willing to travel there or the entrepreneur wasn’t willing to travel here. So for me its just about quality of life in terms of ability to get home for dinner, get back to the office and go back and forth. You know we work on two time zones: the east coast and the west coast. If [the office] was further away I might not be as productive.

Is that the struggle for First Round? Because now there’s a Philadelphia, San Francisco and New York office and there’s four of you?

I might actually argue that while I have a strong network in Philly, my network is Silicon Valley is just as strong if not stronger. So when I’m trying to help an entrepreneur on the West Coast I feel like I can be extremely helpful in terms of recruiting and strategy.

And I’m out west enough that the proximity challenge isn’t insurmountable. So we’ve had to invest to do that. We’ve had to build an office in New York, we’ve had to build an office in the valley and we’ve had to build a team in all of those areas and build a footprint. We view ourselves as four partners that just happen to be working out of whatever office they are at right now.

You are almost the ideal Wharton grad for Philadelphia. You come from out of the area, you go to Wharton, you contribute jobs to the local economy. So I wonder many Wharton grads don’t decide to stick around.

My path was more of the exception.

Why do you think that is?

Had I not started a company right out of school and not had any employees, I don’t know if I would have stayed here.

Let’s try to take a different metaphor. I’ve come to see Philadelphia as a place that has a lot great theaters. And there are 70 schools in this area one of the highest densities of schools out there. There are a lot of people at these schools that want to be actors or actresses. And what I’ve seen though is that if you are a graduating student and are an actor or actress not one of them says “I want to be king of the Forrest Theater.”

They move to Broadway. And that’s where the ecosystem that they play in is [established]. I’d say that Philadelphia, as a tech hub, there are definitely bright spots and it is getting brighter. The fact that Technically Philly exists and it didn’t 18 months ago is telling. You have Philly Startup Leaders and Indy Hall. There’s a lot of groups. I think that’s wonderful and I think that’s improving the Philadelphia start-up scene… but I think it’s still hard to compete with Hollywood.

Maybe its an uphill battle, or maybe its misguided? Or maybe we should just try and play to our strengths of pharma?

I’m a big believer in Philly. I’ve started several companies here that have been successful, I’ve invested in companies that have been successful and I’ve met lots of quality of entrepreneurs here. I would not want to discourage anyone from trying to improve on Philly’s tech scene. But I also don’t know if you even need to compare.

New York has a great Chinatown, Philly has a strong Chinatown and they’re good Chinatowns. But stop trying to compete with China.

Most of our readers have lived here since 2002, 2003, not really part of that first generation of online startups like you were. So what have you’ve seen is the biggest difference from the CDNow and Half days versus now?

We’ve invested in almost every major tech market in the country, so one of the things I’ve seen when we compare Philly is that we tend to think we have a really good start-up generation right now. But for whatever reason, the past generation isn’t as engaged.

There’s not that institutional memory from the first round?

We are seeing a lot of first-time entrepreneurs in the region, which is great. But this is the seed-planting stage. You are going to see 100 of these entrepreneurs, ten of them might have some level of success and they might have management teams of five people, so they are new entrepreneurs that will go out and plant. It’s takes some time to move.

Basically, you’re sitting here with your first generation of seed planting, whereas out west you have the redwood forest.

What are the characteristics you look for in a entrepreneur when funding them?

For a start-up, I like to fund a heat-seeking missile. It used to be that, 30 years ago you, had to aim missiles. From the moment you launched it, you press go and you have no ability to change the course of that missile one you launched it.

But the heat-seeking missiles are a modern invention that you launch and it adjusts and looks for the heat signature it looks for the target. And if the target is moving it changes. It can start off heading north and then head west or south.

What new trends and things are popping up that get you excited?

At the macro-level, I think there is a massive disruption that’s occurring.

In what way?

We are really focused on the cloud and software as a service, and we are very focused on mobile. I think geography and location-based services is [also] really important.

I think that the concept of redefining the data sets that are available online and their accessibility online is a big trend. Sort of what we have been calling the “implicit web”.

Sort of the API-azation of our lives.

Yeah. When you think about it, it used to be that all your data was offline. But as more and more started happening online you left more and more digital breadcrumbs. Like myself: you wanna know what TV shows I like? TiVo knows that. Want music i like? Apple knows that. What movies I like? Netflix knows that. Where I eat? Open Table knows that. What concerts I go to? Ticketmaster knows that.

So historically all of that data has been in silos… Now once those silos open up APIs and you connect things to them and through them, I think that is really powerful and transformative.

Every Friday, Technically Philly brings you an interview with a leader or innovator in Philadelphia s technology community. See others here.

Update: Minor copy edits. Changed logo.

As reported in this week’s Venture Capital Roundup, Steve Barsh has had a busy week.

The DreamIt Ventures managing partner got his tons of national press for his latest startup, Packlate.com, from TechCrunch, the Wall Street Journal and the Washington Post. The company, based in University City (though with plans to move to West Conshohocken) aims to be a last-minute vacation booking service and has received funding from ETF Ventures and First Round Capital.

“It’s not a rocket ship yet, but it is kind of jiggling on the launchpad,” says Barsh.

Barsh says the idea has been brewing for years as he mentored young entrepreneurs at DreamIt while maintaining vacation properties in Utah.

“You know the saying ‘Those who do, do. And those who don’t, teach? I like to do both,” he says.

Currently he says he is still dedicating ten percent of his time to DreamIt but says he wants to focus most of his efforts on his new startup. We spoke with Barsh about Packlate’s future, how DreamIt can survive with preoccupied management and when we’ll be able to book a Jersey Shore vacation with Packlate.

As always, edited for length and clarity.

How long have you been working on Packlate? This seemed to come out of nowhere.

I’ve had rental property in Park City, Utah for about ten years and I’ve had this idea for Packlate for the last five. I’ve been kind of doing it on my own for my two condos and when I was doing DreamIt this summer, talking to all these entrepreneurs about de-risking, I was working on Packlate as kind of my “20 percent time.”

A bunch of investors in the Philly area told me I cant de-risk it anymore without cash so they told me “Build it into a company and we’ll fund it.”

We started the company on September 1st. Within three months it was funded and within five months it was in the market. We went really fast… We just wanted to get it out there and see how people reacted.

Steve Barsh, CEO of Packlate

How are people reacting?

Traffic is surging because we keep getting PR. We keep bringing more servers online, so it’s a good problem to have. I said at our first board meeting this week: “If anyone was wondering, we are at revenue.”

So we are getting bookings and generating money. Not a lot, but its a great signal. We’re really pleased.

It’s only for the Rockies now?

[Advisor and StubHub.com founder] Colin Evans hounded on me this summer and said “If you launch nationwide, you’re going to be 3,000 miles wide and a quarter of an inch deep.” You won’t be a marketplace. It would be like walking into the Barnes and Noble and seeing two books in the fiction section. Which means you don’t have a fiction section.

We’ll expand in the spring and summer for other markets.

So I can book the Jersey shore pretty soon?

I hope so. There are a lot of markets we want to open up in.

To switch gears, are you involved in this year’s DreamIt class?

I’m not focused exclusively on Packlate but I am focused extensively on Packlate. I usually teach part-time at Wharton, I’m not doing that this semester.

With DreamIt it will be a very light participation, I’ll do some mentoring, I’ll do a talk, but I won’t be full-time. I can’t do both. If I do both, I’ll do both poorly.

If Packlate takes off, do you see yourself pulling out of DreamIt?

I’ll always have ten percent of my time for DreamIt. To really do both of these things, you have to throw yourself at them.

What’s the next step for Packlate?

We’re refining in our current market and trying to get all of our metrics up and to the right. More booking, more people watching and driving more traffic. We have an idea coming out in the next week that I hope will be completely crushing to the vacation rental industry, which is fun.

Are you worried about the future of DreamIT? You have Packlate, Steve Welsh is running for congress and David Bookspan runs Monetate?

DreamIt is in great hands. They are moving at 100 miles per hour whether I’m involved or not. DreamIt is doing well and is well-backed and it will stay that way.

Every Friday, Technically Philly brings you an interview with a leader or innovator in Philadelphia’s technology community. See others here.

After announcing $1.1 million in venture capital investments, once Central Pennsylvania-based CoTweet is moving to San Francisco, according to the Wall Street Journal.

The company, which develops a web-based application for Twitter that allows businesses to assign multiple team members to control commercial accounts, received funding from West Conshohocken-based First Round Capital and a handful of other non-Philly firms. [Full Disclosure: Technically Philly uses CoTweet for forward-dated Twitter posts]

According to two job openings recently added to the company’s internal job board, the company is headed for the SoMa neighborhood of downtown San Francisco, an area well-known for its roots in the dot com boom.

CoTweet executives are in the process of packing their bags, according to tweeted:

Last week, CoTweet received attention when TechCrunch reported that the company was eyed by Twitter as an “acquisition target” in confidential leaked documents.

Details emerged after the publication acquired hundreds of corporate and personal documents of Twitter employees from a French hacker known as “Hacker Croll.”

According to the documents, Twitter was exploring commercial account opportunities and was possibly considering acquiring CoTweet. Twitter also considered other options, like partnering with or contracting the company.

The hacker who obtained the documents used a series of social engineering tactics to infiltrate a number of Twitter employees personal accounts that included Gmail, Google Apps, GoDaddy, MobileMe, AT&T, Amazon, Hotmail, PayPal and iTunes, according to an extensive and fascinating background piece written by TechCrunch.

The entrepreneur turned venture capitalist, who made his name on the back of the $355 million sale of his creation Half.com to eBay in 2000, has been a bit of a big fish in an underdeveloped Philadelphia pond for some time now. But he doesn’t always take adulation so warmly.

Kopelman was reportedly put off by the label of the wealthiest self-made person in Philadelphia, author W. Randall Jones told the Inquirer. For his new book, the Richest Man in Town, Jones traveled to 100 U.S. cities to collect business wisdom from those atop the income brackets in their towns and found Kopelman to be our pick of the litter.

“He was very upset with me,” Jones told the Inqy.

While Kopelman may have disliked the thought of being placed above a host of the city’s billionaire’s boys club, it’s not the only big call he’s gotten this week.

As tweeted:

Here’s the science behind the rankings from TC:

Vijay Dondeti, a graduate student in bioinformatics, applied the analysis in the Hochberg paper to about 2,700 investors in CrunchBase who participated in over 3,300 startup funding rounds between 2006 and 2008. He scored each investor based on how well connected they are to other investors as well as how well-connected their co-investors are to other investors. �In summary,� says Dondeti, �to get a high score, you need to co-invest often with others that also co-invest often.� [Source]

It’s hard to overstate what that means for the region. With news that Ben Franklin Technology Partners is on the state budget chopping block, early stage funding becomes vital. FirstRound certainly invests heavily outside our region, but it’s still a serious international VC firm just a regional rail ride from Center City.

And that’s some attention that Kopelman will have to tolerate.