MyPunchblog

Since I started MyPunchbowl.com a few years ago, I’ve noticed a few times where I’ve felt “in over my head.” Sometimes it’s when I have a million things coming at me at once (like this week) and I have to brutally prioritize my list of to-do’s. Other times it’s when I’m in a high-level meeting with an investor or potential partner and I feel overwhelmed by the importance of presenting MyPunchbowl well. Other days I can feel overwhelmed by the reality that our employees and contractors have put their faith and livelihood into Punchbowl Software.

Jeff Bussgang (Flybridge Capital Partners) wrote about this phenomenon today, and specific passages really struck a chord with me.  I remember in the early days of Punchbowl a lot of nights as Jeff describes in his blog post: “I would come home at night, shake my head as I recounted to my wife the decisions I was responsible for making, and reflect that I really had no idea what I was doing.”

Jeff continues his blog post with a description of the 80/20 rule for entrepreneurs: 80% of the time you should be in control of what you’re doing, and 20% of the time you should be in over your head.

I like the spirit of this 80/20 rule, but I would amend it a little. For me, I think it’s important to concentrate the feeling of being in over my head into a burst. I think it’s important that once in a while — for a stretch of a few days in a row – to push myself out of my comfort zone and feel in over my head. Sometimes this will take the form of attending a conference where I have to do a lot of meet and greet with executives way over my level, and sometimes it takes the form of tackling a really hairy product or technical issue with our development team. The key for me is to concentrate that feeling of being “in over my head” into a few specific days, and then get back to the tasks and objectives that I want to achieve for the month.

If you’re an entrepreneur and you never feel “in over your head” then do whatever it takes to stretch yourself to that place. It’s not comfortable while you’re there, but soon you’ll look back and see how far you’ve come, who you’ve met, and what you’ve learned.

Thanks to Jeff Bussgang for tackling this important subject.

It’s Saturday, May 3rd, 2008 — the first Saturday in May. That means it’s Kentucky Derby Day.

As I sit in my home office on this rainy morning, my wife is downstairs preparing Mint Juleps and various southern foods (from the smells I’m guessing pulled chicken, corn bread, and sweet potato pie). My job is to help set up the chairs in front of the TV and nail down the betting rules. Here’s what I got so far:

$2 to enter. Pick a horse randomly from the hat. If you pick Big Brown, Colonel John or Pyro (one of the three top horses on the morning line), you have a choice to make:  

• For Big Brown: pay 5 times more (total bet $12) or choose another horse
• For Colonel John pay 3 times more (total bet $8) or choose another horse
• For Pyro: pay 2 times more (total bet $6) or choose another horse 

3^rd place: Double total bet, 2^nd place: Triple total bet, 1^st place: Remaining pot
A few of the Punchbowlers will be coming over to the house this afternoon (it’s not a required company event like our annual Groundhog Day Party but they’re coming anyway!) Should be a fun afternoon. MyPunchbowl was very useful for our online invitations and potluck coordination. Damn, I wish we could have purchased Kentucky Derby party supplies through MyPunchbowl. Someday….

Whether you’re having a party or not, turn on the TV around 6pm EST (NBC) for the best two minutes in sports. See it once and you’ll be hooked. Happy Kentucky Derby Day!

I’m taking some time over the next week to unplug from the office. I’ll be shutting down completely, not reading emails or connected to the web world….

In the meantime, here are a few related blog posts to read:

Need perspective? Then go on vacation

Why NOT to work on vacation

I’ll be back in about a week. Until then, I’ll be here:

Have a great week!

I get bombarded from outsourcing companies all of the time. Some are professional requests, some are more salesy, and some are downright pushy. I usually delete most of them, but this one (that I got last week) was too good/funny not to post. Read carefully.

Sir, this is Jahangir from Art n Design. We are the team of expert freelancers, we know the value of time and professionalism. We are agree on all of your terms and conditions. We’ll sign the contracts with you and then move forward. Give us a chance to proof ourself. We are young innovative and professional. We have worked in Professional environments and know how to deal with the things even in tough deadlines. I can provide you samples on Ruby on Rail if there is a chance to get some freelance work. We can work on any terms and conditions with acceptable prices.

My favorite line: “Give us a chance to proof ourself.” Maybe we should hire them for editorial.

I’m really proud of the announcement we made this morning — Punchbowl and Kayak.com have teamed up to offer a party planning travel center on MyPunchbowl.com. The team at Kayak has been great to work with, and we’re really happy to offer travel services right alongside our event planning toolset.

Here’s the press release we issued this morning:

MyPunchbowl.com and Kayak.com Launch Party Planning Travel Center
MyPunchbowl adds Kayak.com travel search capabilities in time for graduation party planning.

Framingham, Mass (PRWEB) April 15, 2008 — According to the U.S Census, more than 6 million students will graduate from college and high school this academic year. For many families, a graduation provides a reason to celebrate - but it also presents coordination headaches to plan the party and get everyone to the event destination.

Today, MyPunchbowl.com a leader in online event and party planning, has answered these needs with the launch of a new party planning travel center powered by Kayak.com, the world’s largest travel site. Kayak.com’s award-winning search functionality has been added to MyPunchbowl and provides quick access to the most comprehensive travel search on the Web. Party planners and goers can now search prices and availability for hundreds of airlines, more than 100,000 hotels and all major rental car brands without ever leaving MyPunchbowl.com.

“Lots of our users are researching trips for events such as graduations and family reunions and we are pleased to bring the power of Kayak.com straight to the party planning source,” said Paul English, CTO and co-founder of Kayak.com. “In this difficult economic climate, many travelers may need to price a trip before replying to an online invitation and now these consumers simply and quickly use the Kayak.com search widget to research prices and availability without leaving MyPunchbowl.com.”

The MyPunchbowl Travel Center includes all of the core features that are available on Kayak.com, plus:
• Event hosts can search flights, cars, and hotels directly from their MyPunchbowl account
• Event guests have travel search capabilities directly within the MyPunchbowl save the date or online invitation
• A simple option enables hosts to choose whether or not to display the travel center on the guest view

“Our new travel center furthers our goal to be the leader in end to end party planning online by integrating Kayak.com’s travel search technology within the site,” said Matt Douglas, CEO, Punchbowl Software. “Like MyPunchbowl, Kayak.com makes planning travel easier by searching hundreds of travel sites for prices and availability, and providing all the tools and content a traveler needs to make an informed decision about their purchase. Together, Kayak.com and MyPunchbowl make attending an event even easier.”

MyPunchbowl offers a modern, user-friendly interface that adapts to the party planning needs of the host. Unique features such as “Pick a Date” and “Party Checklist” along with online invitations help hosts with coordination and logistics through every stage of party planning. MyPunchbowl is the perfect site for planning a graduation party, birthday party, or important life milestone celebration.

To view the MyPunchbowl Travel Center, signup for a free account at http://www.mypunchbowl.com

About Punchbowl Software
Punchbowl Software was founded by software and user interface experts Matt Douglas and Sean Conta. They were frustrated with the available methods for planning an event or party and knew there had to be a better way. Matt was previously in senior management positions at Bose Corporation and Adobe Systems. Sean has held positions at Zildjian Cymbals and Innoveer Solutions as a user-experience specialist. The company is located in Framingham, MA in the heart of the Metrowest technology center of Boston and is backed by Intel Capital. To learn more and sign up for a free account, visit http://www.mypunchbowl.com

About Kayak.com
Kayak.com, the largest Travel 2.0 site in the world, is a global Internet media company operating Kayak.com, Sidestep.com, TravelPost.com and TravelSearch.com. Kayak.com and SideStep.com display results from more than 400 travel sites, providing prices and itineraries for hundreds of airlines, more than 100,000 hotels, all leading rental car companies and 18 cruise lines. Kayak.com has won more awards since launch than any other travel site including “100 Best Products of 2007″ by PC World; “25 Sites We Can’t Live Without” by TIME Magazine; “Best Search Engine” by the Associated Press; and “Best of the Web” by BusinessWeek, Forbes.com and US News & World Report. Launched in 2005 by co-founders of Orbitz, Travelocity and Expedia, Kayak.com’s investors include General Catalyst Partners, Sequoia Capital, Accel Partners, Norwest Venture Partners, Trident Capital, Oak Investment Partners, Lehman Brothers Venture Partners and America Online, Inc. Kayak.com has sites in the UK, France, Germany, Spain and Italy. For more information, visit www.Kayak.com.

For more information about MyPunchbowl.com, please contact:
Matt Douglas
Punchbowl Software   
650-814-3393     

For more information about Kayak.com, please contact:
Kellie Pelletier   
Kayak.com   
203-899-3111   
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Scott Kirsner of the Boston Globe wrote a fun blog post last week with his list of 50 interesting Boston-based companies

Here was his “off the cuff” criteria for the list:

There were basically two questions I considered:

1) Is the company working on something important, or at least fun?
2) If you worked there, would you put people to sleep explaining what you do?

If the answer to the first question is “yes,” and the second “no,” the company is eligible.

MyPunchbowl made the Web 2.0/Digital Media list along with successful companies such as Brightcove, Maven Networks, and TripAdvisor.

If you’re interested in the innovation economy, Scott’s blog is a must read. Thanks for including us Scott!

Punchbowl Software is looking for a person to lead our marketing communication efforts. If you know anyone who would be the perfect fit, please send this along. Thanks!

Who we are:
• A group of highly-skilled software professionals
• A Venture Capital backed early-stage startup
• A company located in Framingham, MA

Who you are:
• You are bright, articulate, and have excellent writing skills
• You have experience dealing with the press, key influencers, and bloggers
• You have expertise in utilizing email newsletters as a component of a well-rounded marketing strategy
• You have a working knowledge of search engine optimization
• You know how to leverage social networks and Word of Mouth to drive user adoption
• You have enthusiasm and passion with readiness to join an early-stage startup
• You live within a 45 minute drive of Framingham, MA.

To apply for this job:
1) Create a user account at http://www.mypunchbowl.com
2) Send a *one page* resume, impressions of the site, and brief introductory email to jobs at punchbowlsoftware.com.

We *DO NOT* pay recruiter fees. Please: no recruiters, headhunters, offshore development teams, or offshore individuals.

The Webby awards are kind of like the Academy Awards for the web. For years, they have been recognized as the most important award to be bestowed on a web site. In the early days, a website that earned a Webby was sure to be a commercial success.

As the web has evolved, the annual Webby awards have been a constant. Each year, they are still an important barometer of the best websites available.

We’re really happy to announce that MyPunchbowl has been nominated for a Webby award in the category of “Events.” Here’s part of the email that was sent to me: “As one of only five nominees in its category, your work and the team behind it are eligible for the Internet industry’s two most sought-after awards: The Webby Award and The Webby People’s Voice Award. This honor signifies the highest standard of excellence.”

There are two winners for every category:

1) The Academy Webby Awards’ winner, selected by the 550 member academy

2) The People’s Voice Award winners, selected from voters like you

So, we need your help! Please vote for MyPunchbowl for the People’s Voice Award (unfortunately, you have to signup for an account in order to vote. If you love MyPunchbowl, I hope you’ll take a minute to create an account and vote for us. Once you signup to vote, you’ll find us under the Living>Events category).

Thanks in advance!

I’m not a huge fan of conferences — perhaps it’s because I’ve been to so many over my 15 years in the software industry. I had a good streak going for a while: I had been to every MacWorld conference (in both Boston and SF) for five years running, and I went to every National Association of Broadcasters (NAB) tradeshow for 8 years in a row.

Last week I attended the AlwaysOn Venture Summit East conference. The conference is a mix of entrepreneurs, VC’s, and a handful of press people. There were about 350-400 people at the event.

My plan was to go on Tuesday only, and skip the event on Wednesday. When I went on Tuesday, I was blown away– here were most all of the VC’s that I wanted to meet; all accessible and available to talk to within a few hours of an afternoon. I sat in on a couple of panels, but that was no comparison to the networking I was able to do in the main hall. I left the meeting on Tuesday with a stack of business cards and a few confirmed meetings for the future. Pretty darn efficient.

On Wednesday I had a few meetings scheduled throughout the day so I wasn’t planning to go back to the Venture Summit East conference. When I woke up in the morning, I felt something pulling me back. So I drove to Boston, and on the way I cancelled my other meetings. When I arrived at the conference, I sat down for lunch. Within a few minutes, I had met another few VC’s that were interested in Punchbowl. The afternoon was equally as fruitful — had a quick conversation with Scott Kirsner from the Boston Globe and met Bijan Sabet from Spark Capital and Chris Greendale from Kodiak Venture– just a few of the people in the stack of business cards I carried away from the event.

It’s not often I’ve gone to a conference where I feel like the time spent at the event was more efficient than the time I could have spent in the office. The AlwaysOn Venture Summit East was fantastic, and I look forward to the conference next year.

If you’re involved in the tech scene in or around Boston, you’ll appreciate this list of upcoming Boston tech events. Thanks to Don Dodge for putting together this list.

You’ll probably see me at the Web Innovators Group meeting and perhaps at an upcoming MITX event. I would also like to attend the Nantucket Conference, but I’m not yet sure we’ll have the budget to do so.

If you’re going to one of these events and want to meet up, just drop me a line before the event.