Updated 4:15 pm with new photo. Anytime you get a few hundred people in a room and add a couple of drink tickets, there are bound to be some interesting moments. And when that crowd is comprised of the techies, entrepreneurs, risk-takers and rich people from the startup scene, you’re starting from some pretty fertile ground for quirkiness.

Last night’s Seattle 2.0 awards didn’t disappoint. From organizer Marcelo Calbucci’s exasperation at the crowd noise to a friendly faceoff between a couple of mascots, these are the moments that stuck out to me. Check out the Seattle 2.0 page for the list of actual winners, along with a few other thank-yous and tidbits that Calbucci called out.

—Rand Fishkin threatens to strip: When it was time for the mingling to stop, Calbucci had to plead—and almost threaten—the crowd to detach itself from the main bar, quit chitchatting, and sit down for the show. It still hadn’t quite settled down when SEOmoz CEO Rand Fishkin—a sponsor of the event—took the stage for a few remarks, so he took matters into his own hands. “I’m about to start taking off my clothing, unless–unless!–you sit down and be quiet,” he said. “This is a threat.”

The tactic may have had the opposite effect, however, because once Fishkin tossed his dress shirt toward the crowd and stood there in a white v-neck T-shirt, someone rushed the stage and appeared to try to tuck money into his waistband.

—Soul-searching: The overall tone of the program was a mix of boosterism and self-criticism that you encounter constantly in Seattle’s tech startup community—on one hand, the town’s instigators are beating the drum about why Seattle is good and how it can be great. On the other, there’s plenty of hand-wringing about why this next-level evolution hasn’t happened yet, and what else could be done to ignite people.

Calbucci hit this sentiment early on with a heartfelt speech in which he compared his Seattle 2.0 website to a community restaurant—it doesn’t make money, and in fact can be a drain on personal resources. But the owner clearly sees that it has value to the community, and worries what would happen otherwise. “If I close it, I fear that no one is going to do what I’m doing right now,” he said.

—Mark Suster, from crowd control to inspiration: Suster, a Southern California entrepreneur-turned-VC, was the keynote speaker. He created a bit of anticipation for the speech by publishing this Seattle-themed piece about building a startup community, and the talk itself didn’t disappoint. It started with Suster over by the bar area, wearing a Tony Robbins-style headset, telling Calbucci that he was going to take another run at shutting up everyone who was still mingling and refreshing their drinks.

Then he waded into the crowd, and gave them a once-over that was broadcast over the PA system: “I was standing right next to Marcelo and it was so fucking hard to concentrate with you guys talking,” Suster said to the surprised patrons.

His speech detailed what he felt was needed to build capacity for more entrepreneurs and startups in a place like Seattle: Get “wantrepreneurs” off the sidelines, get would-be investors off the sidelines, pull the trigger on your big ideas, be cheerleaders for your community, but also don’t believe the hype of what’s hot now (complete with Public Enemy album cover shot).

“Do we need another fucking check-in application for restaurants?” Suster asked. “I like Foursquare—I’m not critical of it. But do we need another deal site?”

—Mascots: Promotional hackery, yes. But mascots do the job (I’m writing about them, aren’t I?). The team from Deal Springer—offering a kind of reverse-Groupon engine that allows local businesses to set and promote their own online discounts—hauled out a blue lycra full-body suit that some unnamed fellow rocked along with all-white sneakers. He startled at least one lady who was not expecting to encounter a shimmering, shrink-wrapped dude, but also got his picture taken plenty of times.

Not to be outdone was the group from Giant Thinkwell, which is building a way for celebrities to engage their fanbase with online and mobile games. They brought a giant squid mascot, complete with glowing orange eyes, that bobbed ominously in front of the stage as Kyle Kesterson accepted his award for best designer.

I didn’t see it happen myself, but Deal Springer’s Nick Huzar sent along the photographic evidence that the pair accepted my earlier Twitter challenge for a mascot confrontation. No word on who dominated.

Update: Giant Thinkwell’s Kesterson sends this additional photo (also shown at top), which may be showing some sort of mascot dance-off in progress.

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A few friends have asked me how my life has changed since I moved from Boston to San Francisco to open Xconomy’s Bay Area bureau. Do you want to know the real answer? I drink more.

A lot more.

In the Silicon Valley technology startup world that I cover, there’s at least one cocktail party, private dinner, coder beerfest, pre-conference gathering, post-conference gathering, movie screening, gallery opening, or other excuse for the alcohol to flow every freaking night of the week. Usually more than one. (If you don’t believe me, just subscribe to the Silicon Valley edition of StartupDigest, a guide to startup events curated by a cool guy here named Chris McCann.)

It’s like living in an infinite Mad Men episode. Raymond Carver, the American short story writer and poet, once wrote that wine is the worst drink to get drunk on—”hangovers you don’t forget”—and I’m learning that he’s right. I should probably switch to beer. San Francisco, after all, is home to at least 11 breweries and innumerable brewpubs. But when you live so close to Napa…

All kidding aside, I think there’s a real lesson here about the differences between Silicon Valley and other major hubs of technology innovation. In a column a few weeks ago headlined The Real City of Innovation is Everywhere, I argued that the Internet and the outsourcing revolution make it possible to build a startup just about anywhere these days. And it’s true. But when you look at where the startup founders really congregate, and where the angel and venture dollars are flowing to, Northern California still dominates. There’s obviously something in the water here. And I think that something is alcohol—or, more to the point, the schmoozing that alcohol facilitates.

Laura Fitton, aka @pistachio, the founder of the Cambridge, MA-based Twitter app store Oneforty, sent me an interesting note recently. She’d just visited the Bay Area, where several of Oneforty’s investors and advisors are based, and I had commented to her that I was overwhelmed by the number of startup stories that are begging to be written here (as this peek inside my story pipeline illustrates).

“I struggle so hard with how to bring that ‘steeped in startups’ feeling back home with me every time I fly back from SF,” Fitton commented from Cambridge. “We’re just too siloed here as startup teams—makes it even lonelier and prevents a hell of a lot of product innovation…We HAVE to overcome that isolation and siloing if we’re going to be inspired and energetic and passionate, not just in our founders but our entire teams.”

I’ve heard the same lament from other Boston-area entrepreneurs. I don’t have as much data from Xconomy’s other home cities of San Diego and Detroit, but I’m guessing that the siloing feels just as bad, if not worse.

Well, here in Silicon Valley and San Francisco they have this cool invention for overcoming isolation. It’s called getting together for drinks after work. From what I hear, this invention has spread to some circles in New York City, especially the Wall Street crowd. But it has yet to catch on in Boston’s startup community, where it seems that every weeknight is still a school night.

The thing is, you don’t necessarily have to leave work to drink. The beer flows freely at Google’s TGIF, the Friday afternoon gathering where … Next Page »

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Here’s an interesting snapshot of a lean, consumer-oriented Internet startup that has survived the recession so far—and is looking to take its business to a new level.

Framingham, MA-based Punchbowl Software, an online party-planning company, said today it has surpassed one million registered users as of a few weeks ago. That number includes senders and receivers of the company’s party invitations and e-cards, and it is a significant step for the business, says Punchbowl founder and CEO Matt Douglas.

After a tough 2009, the company’s “growth has been outstanding,” Douglas says. He declined to give specific numbers, but emphasized that “traffic and growth is accelerated.”

The startup also has acquired the domain name Punchbowl.com (it previously used MyPunchbowl.com). The company bought it from Rick Schwartz, the domain name pioneer who previously sold such venerable assets as Candy.com and Men.com for millions. Douglas wouldn’t say how much he paid, but said it was between one dollar and $5 million. There is strategic value, he says, in having a two-syllable brand named after an object—see Kayak.com or Facebook.com (which used to be TheFacebook.com back in 2004).

My colleague Wade first profiled Punchbowl back in October 2007. The company’s software helps party hosts do things like pick dates that work for the majority of people on their invite list, design invitations, track RSVPs, buy supplies, and share photos and videos after the event.

Punchbowl currently has eight employees plus a half-dozen contractors. It raised its most recent financing round in 2008—$2.1 million from Contour Venture Partners, Intel Capital, and eCoast Angels. The company also said today that Michael Waxman-Lenz, former senior vice president and general manager at American Greetings, has joined its board. American Greetings, Hallmark, and Evite (owned by IAC) are some of the big players in Punchbowl’s sector.

The startup makes money through a combination of licensing deals (to customers including 1-800Flowers and Oriental Trading), memberships, local advertising, and some e-commerce. Punchbowl’s party business is pretty seasonal—and with Halloween and the holidays coming up, its about to be high season, Douglas says.

“Revenue has been very strong,” he says. “We’re right on our plan, and it looks like the pipeline is opening up more.”

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We have a lot of events here in Seattle that are so quintessentially representative of Northwest culture—Bumbershoot, Folklife, Bite of Seattle, SeaFair. And then there are all of the gaming conferences—like Casual Connect, and the Penny Arcade Expo—and way too many tech-themed meetups to count. Each and every event, no matter how different, is blogged, Tweeted, and talked about. I think it’s safe to say we’re a pretty diverse—and technologically inclined—bunch.

But I’d never heard anyone be so absolutely upfront about the nerdy nature of Seattle’s tech culture—that is until word got out of the first annual Seattle Geek Week.

The inaugural Geek Week—ten (not seven) days of tech-oriented “geeky” events, kicking off today—is the brain child of Seattle-area entrepreneur, technology consultant, author, blogger, podcaster, enthusiast, and self proclaimed geek, Chris Pirillo.

Pirillo, who founded content publishing network Lockergnome in the early ’90s and has been the man behind the Gnomedex tech conference for the last ten years, says Geek Week is an opportunity for Seattleites to wear their “geek” badges with pride. He says he’d witnessed other cities “rally around their own communities,” so why not do the same for techies, nerd, and “geeks” right here in Seattle?

“Geek Week is there to get people amped up and to raise general awareness for what I believe is a geekiness inside of Seattle,” Pirillo says. “I see all these art festivals, and that’s great because you see art geeks there. I see these food festivals, and that’s great because you see food geeks there. This is for technology geeks.”

At Geek Week, Seattle techies will have a chance to come out of the woodwork and commiserate on all things geeky on the Seattle tech scene. The next ten days will be filled with panels, conferences, meet-ups, and parties on a variety of techie topics—from software and hardware to entrepreneurship, cleantech, social media, startups, and demos. Seattle tech organizations sponsoring events during Geek Week include BarCamp, Social Media Club, TechKaraoke, Innovate100, TechCafe, and more. Some events are free, while others require registration. Check out the full lineup here.

They’ll be a little something for everyone, according to Pirillo.

“People like getting out, they like getting together with friends, they like meeting new people,” he says. “My hope with this is to get out to communities around town small and large, and cross pollinate—I hope to have the Medici effect.”

I asked Chris what he thinks are the events to watch for out of the 10-day lineup, and he listed off a handful of what he thinks will be the popular picks, including the two major conferences … Next Page »

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By now most Xconomy fans know that we’re in the middle of a big game of musical chairs inside the company. Well, next Tuesday night will be your chance to join the fun. We’re throwing an open party at the Cambridge Brewing Company, at One Kendall Square in Cambridge, to welcome Greg Huang, who’s leaving our Seattle office to become the new Editor of Xconomy Boston, and to give a sendoff to Wade Roush, who’s leaving Boston to become Editor of Xconomy San Francisco.

The festivities begin at 5:00 p.m. The first few towers of beer are on us, so show up early!

For the whole back story about the developments at Xconomy, see Bob’s story about the opening of Xconomy San Francisco, his subsequent story about the staffing changes, Luke and Wade’s manifesto for the San Francisco bureau, Greg’s ode to innovators in Seattle, and Wade’s goodbye to Boston.

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Framingham, MA-based Punchbowl Software, the company behind party planning site MyPunchbowl.com, said today that it has acquired the assets of I’m In, a group vacation website formerly owned by Waltham, MA-based GroupGo. Punchbowl’s founder and CEO Matt Douglas says the local search tools created by I’m In have enabled MyPunchbowl to launch a new local vendor portal where party planners can connect with small businesses.

“I had known the guys at I’m In from the local startup scene,” says Douglas. “They were building a group travel and local search product for the trip and travel world, and what impressed me most was their local vendor portal. They were doing a great job, and we kept an eye on them. Over time, the opportunity came to us to acquire the property, and long story short, I decided to pull the trigger. It’s not every day that a startup acquires another startup, but my investors and our board got together and said, ‘You know what, this is something that could really accelerate the company.’”

Punchbowl has acquired I’m In’s software code, designs, trademarks, and domain names, but hasn’t brought in any of its former employees. Douglas isn’t saying how much Punchbowl paid in the deal, but he says Punchbowl didn’t have to raise any new venture funding to make the purchase. The company’s most recent venture round of $2.1 million, supplied by Contour Ventures, Intel Capital, and eCoast Angels, came in September 2008.

Punchbowl earns revenue largely by generating sales leads for party vendors, so the new directory could be a big asset. “I can’t overemphasize how big of a project it is to launch a local vendor portal for 50 states and 30,000 cities—there are over 1 million vendors” in the new portal, says Douglas. “The technology we acquired will give us a huge head start, and we’re excited that we can finally talk about the acquisition and our new portal.”

Don Dodge—the former Microsoft emerging business team director who announced this week that he has accepted a position at Google—is on the board at Punchbowl. We profiled the startup shortly after its launch in October 2007.

GroupGo, meanwhile, was founded in 2005 by entrepreneurs and hotel-industry veterans Brian Harrington and Josh Lesnick and had backing from Annex Ventures. The company was known for helping groups of young adults plan so-called “girlcations” and “mancursions” to locations such as Napa Valley or Las Vegas. Boston.com profiled the company in 2007.

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Want to find out where the best election parties will be on Tuesday night? Check out CultureMob’s top 10 list for Seattle here. The list includes a big drinkfest, the Stranger’s Election Party at Showbox at the Market downtown, as well as the more serious Election Night Special at Town Hall Seattle, complete with political consultants and reporters. My personal preference would probably be for Neumos or the Nickerson Street Saloon. (Any place that calls itself a saloon is OK by me.)

No word yet on where the founders of CultureMob—or rather, Green Couch Conspiracy, the site’s holding company—will be partying themselves. (Wait, I have a green couch, and so do two good friends of mine…) The Seattle startup, which launched a local site in December 2007, helps people discover, promote, and share local events in art, music, sports, and the like. CultureMob expanded to the Portland, OR, and Denver, CO, metro areas in May, and then to the top 25 U.S. markets in the past month. The company is largely self-funded, with some support from Benaroya Capital and angel investors, and has about a dozen employees. Its founders, including entrepreneurs Steve McCracken and Chris Pierard, previously co-founded Serials Solutions, a Seattle company that built digital information management tools for libraries. In 2004, Serials Solutions was acquired by ProQuest; its co-founders exited in 2006 for about $18 million.

There’s more expansion to come in CultureMob’s future, so watch this space. In the meantime, be sure to get out and vote…

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Everyone has a neighbor or a relative who loves to throw parties—you know, the people who make their Halloween or Christmas extravaganza bigger every year, with more lights, lawn ornaments, costumes, and food. The folks at Punchbowl Software are a lot like that: they keep overhauling their Web 2.0 party-planning website MyPunchbowl, making it fancier and more useful.

Today Punchbowl took the lid off the site’s biggest redesign yet. “Many of our features have gotten a facelift,” says CEO Matt Douglas, “and our home page has been redesigned for conversion”—that is, to entice more people to sign up as members and to use MyPunchbowl’s main features, which include a utility for negotiating a party’s date, a save-the-date notifier, party-supply checklists, and photo albums for after-party sharing. The user interfaces for all of these features have also been revamped, Douglas says.

But the most prominent new feature is the online “Design Studio,” where hosts planning parties can create customized electronic invitations by choosing from a variety of clip-art options such as colorful backgrounds and ribbons. The company says the studio provides a “green” and “stylish” alternative to sending out paper invitations. And actually, the phrase “clip art” doesn’t do justice to the elegant designs Punchbowl has created as starting templates (click on the thumbnail at left for a closer look).

It’s been a busy fall at Punchbowl—the company announced just three weeks ago that it had raised $2.1 million in a venture round by New York-based Contour Venture Partners and existing investors Intel Capital and eCoast Angels.

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A basketball hoop in the Museum of Science lobby, teams of entrepreneurs playing 3 on 3. Boston Celtics cheerleaders rooting them on. A rockin’ band. Shots of blueberry martinis doled out in test tubes. A contortionist—yes, a female contortionist in a skin-tight body suit.

Did I just go through a time warp, I wondered? This was 2008, not 1998, wasn’t it? Bill Bulkeley of the Wall Street Journal was standing next to me and put it best: “A pre-bubble party in a post-bubble economic environment.”

Welcome to Highland Capital Partners’ 20th anniversary bash. It was held last night—pre-debate—and it truly would have impressed even Silicon Valley firms. Scores of representatives from Highland’s past and present portfolio companies were on hand—some taking part in the 3 on 3 tourney (owater edged City Sports in the championship). To inspire them perhaps, Highland venture partner Wyc Grousbeck, who’s also managing partner, governor (yes, governor), and CEO of the Celtics, even brought over the C’s championship trophy and put it on display next to the court.

But whether you like hoops or not, it was a wild, impressive, crazy, head-shaking affair. And the crowd clearly loved it. “I heard this is the greatest concentration of Boston entrepreneurs ever,” one person told me. There was no way, of course, to verify this. But hats off to Highland for shaking us, at least for an evening, out of our economic doldrums.
The only pall over the bash might have been the fact the vice presidential debate was closing fast, causing me, for one, to forego the blueberry martini shots and head home early. But I spoke to a lot of great people, including Highland general partner Paul Maeder and Tom Stemberg, founder of Staples and managing general partner of Highland’s consumer fund. Another great new face for me was Sallie Shuping Russell, now of BlackRock in Durham, NC, and previously the superstar head of the private investment portfolio for Duke University, which invested in one of Highland’s funds. She said she could get me tickets to a Duke or North Carolina basketball game—but that might have been after I mentioned Xconomy might some day open in Research Triangle Park (in any case, I think I’ll have to go down and evaluate our expansion soon). [Editor's note: Bob is of course joking here, and would never accept an extravagant freebie from a source or potential source. Right Bob?]

Here are notes from some of my conversations, most of them having to do with the current financial muck:

—From John Landry, CEO of Lead Dog Ventures, an Xconomist, and former CTO of Lotus Development: “The venture business is potentially turning into not that great a business, because there aren’t that many places to sell their businesses.” (Well, that was the amended version … Next Page »

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Punchbowl Software, the Framingham, MA, startup that runs the Web 2.0 party planning service MyPunchbowl (profiled here last October), has obtained its first major round of venture financing. The company raised $2.1 million from a group of investors including New York-based Contour Venture Partners and seed-round participants Intel Capital and eCoast Angels.

MyPunchbowl is designed to help event organizers and participants settle on a date, issue save-the-date notices and formal invitations, make party-supply checklists, and share after-party photos and videos. Its user base has grown more than 20 percent each month for the past year, according to a press release about the financing round.

The new funding will enable the company to hire more software developers and pursue new strategic and marketing opportunities, the company said. “In this tough economic climate, we’re really excited to have closed such a significant round of funding,” Punchbowl CEO Matt Douglas tells Xconomy. “This illustrates that a fundamentally sound business model combined with explosive user growth will still attract the best investors.”

Bob Greene, a co-managing partner at Contour, said in a statement that the firm was impressed by MyPunchbowl’s viral growth. “We see great opportunity for MyPunchbowl to continue to grow its leadership position in the party and event planning market,” he said.

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