Groundhog Day Party: What I’ve learned

February 1, 2008

There’s an saying in startup companies: “you don’t really know your product until you’ve eaten your own dog-food.” Over the past few weeks, I’ve been using MyPunchbowl on a daily basis as I planned our 12th annual Groundhog Day party. I’d like to think that I know my own product very well, but these last few weeks have helped crystallize my impressions of the product that I’ve helped build. Here’s a quick list of what I’ve learned:

Co-hosts: By far, one of the best features of MyPunchbowl is the ability to have co-hosts. I wish every MyPunchbowl user knew about this feature. As far as I know, we’re the only party planning website to offer true co-hosting. I made my wife a co-host and she’s been able to keep track of the guest list and party checklist by logging into her own account. Awesome.

Manage Guests page: I’m surprised at just how many times I’ve interacted with the Manage Guests page. It’s very useful and has all of the key features that I need. One problem that I’ve spoken with the team about: in my opinion, the page loads too slow. I have about 65 guests on the page, and it takes about 4 seconds to load. Too slow. Look for performance enhancements on this page in the future.

Party Checklist: Very, very useful. It’s great to be able to make a list of everything that we need and have guests choose something off of the list. It really helps relieve the burden of having to handle everything. Example: We put “6 packs of beer” on the list (8 of these), and they have all been taken care of by the guests who are coming. Wishlist: I wish I could set up SMS reminders for checklist items so that the people who agreed to bring something would get a reminder on their phone. Look for SMS integration throughout MyPunchbowl in the future.

RSVP Responses: Another fantastic thing about MyPunchbowl. I love that those who are not coming can send me a private note easily. The people who aren’t coming took the time to write significant, personal notes to me. On other sites, a guest who responds ‘no’ has to try to come up with a witty response (because everyone is going to see it). On MyPunchbowl, the guest can send the host a private note, allowing for a more personal connection. Awesome.

Party Themes: I’m really happy with all of the great themes that MyPunchbowl provides. I was quickly able to find a Groundhog Day party theme that fit what I was looking for. I love how easy it was to sort through the hundreds of templates. My favorite feature on this page is how I can find templates using keywords. I simply went to “G” and chose Groundhog. Simple and easy to use.

All in all, I’m really happy with MyPunchbowl. It really helped us with our party planning, and my wife and I feel relaxed and ready to welcome around 30 guests into our home on Saturday.

Happy Groundhog Day!

Party Planning and Online Invitations with MyPunchbowl


Hey Mike Arrington, get your hands off of me

December 19, 2007

Before the TechCrunch Boston Meetup, I had never met Michael Arrington. (For those of you who don’t know, TechCrunch is a very popular blog in the startup world, and Mike is the founder. As a result, he enjoys “celebrity” status in the startup world and also has his share of detractors).

Now before you read further, you should know a few things. First, I’m not personal friends with Mike — in fact, I don’t know him very well at all. Like most startup entrepreneurs, I simply sent TechCrunch information about MyPunchbowl.com a few days before we launched. I have some experience in PR, so I wrote Mike a pointed email telling him why he should care about MyPunchbowl. Of course, I was very happy when he emailed me back to say that TechCrunch was interested in taking a look. A few days later, I met with Nick Gonzales. Nick is a great person and he really took the time to understand why MyPunchbowl is different. TechCrunch covered our initial launch and again when we launched “Pick a Date.”

Throughout my dealings with TechCrunch, I’ve mostly dealt directly with Nick, but Mike and I have traded a few emails and spoke on the phone once. No interactions of consequence.

Fast forward to the TechCrunch Boston Meetup. I spent most of the night around our demo area talking to users, VCs, and press folks. One of Punchbowl’s board members is Don Dodge, and at one point towards the beginning of the night, Don pulled me aside to introduce me to Mike. We said our pleasantries, I thanked him for inviting us to sponsor, and I moved on. What transpired after our initial introduction was amusing to say the least.

The announcement podium was near our demo area, so Mike was back and forth near our demo area throughout the night. We were very crowded, so it was a tight fit to get by. At one point, as Mike walked by, I put a MyPunchbowl “World’s Greatest Host” sticker on him. With a smirk and a sarcastic comment, he accepted. Here’s Mike sporting the MyPunchbowl sticker:

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Later, Mike inadvertently bumped into me as he passed by our demo area. He jokingly asked, “Who are you? Have we met?” Apparently Mike didn’t know I’m from New York. I pushed him back, pretty hard. Mike’s a big guy, and he was pretty amused at all 155lbs of me leaning into his shoulder. He smiled, and continued on.

20 minutes later, the scene repeated (Like I said, it was pretty crowded…). A smile, a smirk, a slightly harder bump — and he moved on. I’m pretty sure I talked trash and said something to rile him up, but I don’t remember what it was.

About an hour later, the scene repeated yet again. This time he leaned his shoulder into me pretty hard as he passed by. And then we had this exchange:

Matt: (I got in his face.) “Hey Mike, I’m going to kick your ass.” He seemed to liked the challenge.

Mike: “When are you going to stop busting my balls?” He towered over me.

Matt: “When the %^$* are you going to actually look at my site?” (note: although TechCrunch has reviewed the site and we sponsored their event, Mike has never actually registered on the site as far as I know).

Mike: “Give me one reason I should bother.”

Matt: “Because I spent the last 3 years of my life and most of my savings on this startup.”

Mike: (Thinks for a second, takes my card and puts it into his shirt pocket) “Yeah, ok.”

And then….. Mike hugs me. It was a kind of sarcastic “I feel your pain” hug, and he held on as if to prove his point. I laugh and tell him that I won’t let him forget that moment…

Later, I’m downstairs and I tell Don Dodge about what happened upstairs earlier. And he insists on a picture between Mike and I to reenact the moment.

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I’m sure Mike gets hundreds of emails a day — and my guess is that at least 80% of them are people kissing his ass and pitching for coverage on TechCrunch. I don’t know exactly what that’s like, but I have a good idea. When I was at Adobe, I got hundreds of emails a day. It was a constant battle to separate the noise from the gems. Eventually you turn cynical to just about everybody — that is, unless they do something to show you that they are different.

So what have I learned about what Mike Arrington and Matt Douglas have in common? Like me, Mike has a sarcastic sense of humor and enjoys a challenge. He’s got a soft spot for the “truth” about what it takes to start from nothing and build a startup. And while he geninuely enjoys recognition, he can laugh at himself and the absurdity of it all.

I’m not friends with Mike– but get us away from the tech/startup world and I think he and I would enjoy having a few beers and playing competitive air hockey. Just for the record, I’d win.

Here’s another shot of Mike and I at the end of the night:

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So Mike… if you’ve read this far: when are you going to create an account and let me know what you think about MyPunchbowl.com? Don’t make me hunt you down — I may be small, but I pack a hell of a punch.

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Party Planning and Online Invitations with MyPunchbowl


The Kiva.org CTO

December 16, 2007

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Kiva is an interesting company. They are in the business of “micro-lending.” Here’s the basic jist: individuals like you and me can donate small amounts of money (e.g. $10 or $25) directly to businesses in developing countries. Kiva processes the money, and connects to the organizations that provide financing to small (often entrepreneurial) businesses. It’s a great startup, and I’m proud that I’ve (finally) joined Kiva as a user.

But I’m even more proud that my cousin Sam is the Chief Technical Officer of Kiva. (For those keeping track at home, Sam is actually my cousin-in-law, but since I’ve known him for many years, I’ve now adopted him).

Sam is the perfect software engineer. He’s got the geek thing totally down: the type of programmer who talks to himself as he’s coding and who sees the best solution for any problem. The Kiva job is great for him too. It appeals to his sense of responsibility for the world and offers its fair share of technical challenges.

Sam is a very generous person. I’ve been to San Francisco four times already this year, and I’m going again this coming week. Sam not only picks me up and drops me at the airport, but he gives me a place to sleep at his apartment (usually for a week at a time). If that wasn’t enough, he provides me his car so I can shoot up and down the peninsula. Sam has literally saved me thousands of dollars in hotel stays, airport transfers, and car rentals. On my last trip, he wouldn’t even let me pay for gas. Well, sorry Sam—I’ve just made the first of many donations through Kiva in your honor. If you won’t let me pay it back, I’ll pay it forward.

I hope all of the readers of this blog will visit Kiva.org and sign up for a free account. And if you see any problems with the site, let me know. I know the guy who can fix them.

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Party Planning and Online Invitations with MyPunchbowl


Nominate MyPunchbowl for the Crunchies

December 3, 2007

A few of the leading tech blogs are sponsoring a new awards competition for 2007. The blogs involved are TechCrunch (thus the name “Crunchies”), GigaOm (we like them, although they’ve never written about MyPunchbowl), VentureBeat (great blog for any VC deal news), and Read/WriteWeb (good blog for up-to-date product news).

You can participate by nominating MyPunchbowl to one of the 20 categories. To nominate MyPunchbowl or yours truly, visit the Crunchies nomination page.

Thanks for your support of MyPunchbowl.com.

P.S. Shameless plug: Did you miss that?!? You can nominate me….

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Party Planning and Online Invitations with MyPunchbowl


Are we in a bubble?

November 27, 2007

Scott Kirsner wrote an article this past weekend for his Innovation Economy column in the Boston Globe. In the article, he looks at the question of whether or not we are in a economic bubble. As is typical with Scott’s longer form pieces, he sought out opinions from both sides and he does a great job of interviewing people with many different opinions.

Along with the article, Scott produced a video with short interviews of people with opinions on the subject. I was lucky enough to be interviewed by Scott at the TechCrunch Boston event.

I’d like to take a moment to add to the few points I made in the video:

  1. I believe that startups whose sole business model is advertising will have a hard time as we go deeper into 2008 and 2009. Although the market for online advertising is growing rapidly, there simply is not enough demand to fill the supply of startups who believe they can build a business solely on advertising revenue.
  2. I believe that we are in a “startup bubble.” It seems everyday there is a new social network that launches and yet another website that aims at a specific vertical. They can’t all co-exist. At some point, the startup activity will slow down.
  3. Companies (like Punchbowl Software) that have a hybrid business model will be able to adapt more quickly to any economic downturn. At this point, we have more business development opportunities for e-commerce partnerships than we can handle. While we believe that a large percentage of our future revenue will indeed come from advertising, we’re building a diverse business that we believe will help us weather the storm of any economic downturn.
  4. I expect that merger and acquisition activity will pick up significantly during 2008 and 2009. As small companies feel less sure of their ability to survive in an uncertain market and large companies look to invest in new technology and services, I think we’ll see a lot of consolidation in the market. In the past, this would have fueled even more startup activity — over the next 1-2 years I think you’ll see this will have the short-term effect to dry up the startup community.
  5. As always, the market is goes in cycles. A few years from now, everyone will be asking if we are in a recession. I believe that the cycles will be much shorter over the next decade– so we will see more highs and lows. In this kind of a market, timing is everything. Let’s hope Punchbowl Software is in the right place at the right time.

Whether or not we are in an economic bubble this time is debatable and maybe even laughable, but I think one thing we all agree on is that it is a great time to be an entrepreneur.

Thanks to Scott for including Punchbowl in his interview. Scott is great for Boston– he’s asking the hard questions and raising the consciousness of the entire community. As a journalist, I can’t imagine that there is anything more rewarding.

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Party Planning and Online Invitations with MyPunchbowl


Holiday Party Planning: MyPunchbowl gets a Face-lift

November 19, 2007

This morning, we announced a brand-new version of MyPunchbowl.com. We’re very excited about this new release — it’s a complete face-lift of the site and we’ve added a few new features as well. It’s been quite a team effort, and we’re all really proud of what we’ve accomplished. It’s hard to explain how good it feels to ship a new release after months of feature spec’ing and testing, and this one feels better than most. We would love to hear your feedback: particularly we would love to know what you think about the overall new look as well as the new theme selector. To send us feedback, click “Feedback/Support” at the bottom of any page on MyPunchbowl.com. So what are you waiting for? Go check out our new release and start your holiday party planning!

Follow the link for the press release….

MyPunchbowl gets a face-lift in time for holiday party planning

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Party Planning and Online Invitations with MyPunchbowl


OpenSocial and MyPunchbowl.com

October 31, 2007

Yesterday, I spent a good portion of the day writing down some thoughts about social media platforms. My goal is to set a course for Punchbowl Software as a company and articulate our strategy around the social media platforms.

Like most Web 2.0 startups, we dipped our toes in the murky waters of the Facebook platform. In September, we released a Facebook application called “Party Animal.” While it was interesting for us to learn about the Facebook platform, so far Party Animal has not become one of the really popular applications. I suppose we shouldn’t be surprised: as the O’Reilly group so eloquently pointed out, only 84 Facebook applications have 87% of the traffic. Maybe if we had gotten on board early we would have been more successful.

So after spending some of my day thinking about the social media platforms and debating about which platforms to support in the future, it was particularly good timing when I stopped by TechCrunch last night and saw the announcement from Google about OpenSocial. Here’s the deal: rather than companies like ours writing applications directly for the Facebook platform, we can now write to Google OpenSocial and connect with a “new universe of social networks all over the web.” This is interesting.

What does it mean for MyPunchbowl.com? Well, we still have a fundmental question to answer: how much effort and energy should we put towards supporting these social networks? The reality is that MyPunchbowl.com’s traffic is growing fast and our users want new features and functionality on the main site. We’re quickly establishing ourselves as one of the leaders in event and party planning, and we have more opportunities than we can handle right now. Like all startups, we have limited resources. So while this announcement from Google helps companies like ours by theoretically limiting the distraction, it is still a distraction from our core mission.

Once the dust settles from this most recent development, startups like mine still have the same question to answer: is it worth the distraction to develop for the social media sites or are we better off focusing our energy on our main app? From my perspective, Google’s OpenSocial doesn’t help answer this question. It’s just another option to consider.

Additional information and good reading on ZDNet, O’Reilly, Mashable, and GigaOm.


Making decisions with a coin flip

October 24, 2007

Yesterday I was in a meeting — and it came to the point of the meeting when one of the parties in the room had to commit to documenting what we had talked about and sharing the notes with the other party. This moment in a meeting is always a bit amusing. Both parties want to make sure good notes are created after the meeting, but neither side really wants to step up to add more work onto their plate. We’re all busy, and yet we all want to make sure there is written documentation of the good progress we made in the meeting.

So yesterday when it came to that point, we decided it the old-fashioned way: a coin flip. I can’t even recall who suggested the coin-flip, and I believe the comment was made somewhat in jest. But then we looked at each other in the eye and both agreed. Ok, we’ll decide based on a coin flip. No harm, no foul.

The other party provided the coin and did the flipping honors. “Heads” would mean that Punchbowl would be responsible for delivering the document (yep, that means me). With bated breath the coin was flipped….. TAILS!

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Yes, I admit that it wasn’t the most formal way to resolve the issue, but you know something? It worked. I would have gladly taken responsiblity if it had come up Heads. But I’m sure glad it came up tails! Next time you need to resolve this kind of situation, use the coin flip. It works.


Doug Levin

October 21, 2007

This past Thursday night, the Massachusetts Technology Leadership Council held their annual awards. See Scott Kirsner’s blog for a full list of award recipients.

I was very happy to learn that my friend and colleague Doug Levin, the CEO of Black Duck Software won the award for CEO of the year. Doug wrote a post about winning the award — interestingly titled “My Psalm.” It’s nice to see Doug credit Team Black Duck for his award.

I’ve known Doug for more than five years now. We met at the University of North Carolina, where he taught a class on entreprenuership. I actually didn’t take the class, but I reached out to him privately to get to know him. I was moving to Boston within the year, and Doug and I had similar backgrounds and interests.

What followed over the next few years was a number of breakfast meetings, where we traded stories and talked about technology. Before Black Duck began, Doug was interested in the open source community as a whole and we talked about how the software industry would change as a result of open source. During that time I got to know Doug pretty well.

Here’s the deal with Doug: if you can’t take the honest (often brutal) truth, you shouldn’t hang out with Doug. He tells it *exactly* like it is from his point of view, often using descriptive analogies to illustrate his point. He does not mince words — if he thinks you’re doing something stupid he’ll tell you. Be prepared for him to quickly point out your faults with extraordinary detail, and suggest an alternative path that often seems unachievable.

Allow me to illustrate: Doug and I met for breakfast in mid 2006 when I was trying to get Punchbowl off of the ground (just checked my notes: it was 6/28/06). We had gone for a while without meeting — he was knee-deep in Black Duck, and I didn’t feel like I was ready to talk to him about Punchbowl. At that meeting, I described to Doug our progress to date. I was proud of what we had done without any funding — and was ready to show him the plan. Doug took one look at it and point-blank told me that I needed to upgrade the plan to make it attractive to potential VC’s. Then he challenged me to go get someone like Intel Capital to say that they would be interested in being involved in a Series B. I left that meeting feeling frustrated. He hadn’t really acknowledged our progress to date, and had suggested a path that seemed entirely unachieveable.

Looking back, I wish I had pushed Doug after that meeting to help me more. I didn’t know at that point how to “upgrade the plan.” I didn’t know how to get VC’s really interested. Doug suggested that I try to get Intel Capital interested in a later-stage round of funding. But I was looking for seed-stage money. How could I engage Intel at this early-stage?

What transpired over the next 12 months was a steep learning curve and lots of starts and stops. I met with lots of seed-stage investors, was rejected more times than I care to admit, and faced an everyday challenge to keep my head up. If I had met with Doug again, he could have helped me upgrade the plan. He would have shown me a path to success faster than I could on my own. He would have given me the brutal truth.

Eventually I got an introduction to Intel Capital on my own, and the rest is history. Here’s the ultimate irony: I just checked my notes: it was one year to the day from that breakfast meeting with Doug when we finally received a term sheet from Intel. Wow. With our closing on October 1st, it took me 15 months to make the unachievable happen.

There is a reason that Doug won the CEO of the year. He knows how to accelerate success. He thinks big, and does not mince words. He has the ability to evaluate a situation quickly and offer ideas and solutions. But most of all, he tells you the brutal truth — even if it takes you a while to figure out how to achieve the seemingly unachieveable.

Congratulations Doug.


How to prepare for an interview

October 17, 2007

After our recent funding announcement, my first order of business is to hire people to fill our newly open positions. As anyone who has started a company will tell you, the people you hire early into the company are *critical* to the long-term success of the business. The first few employees set the tone and vibe for the company. We strive to hire the best people we’ve ever worked with. And we spend alot of time together, so it’s critical that we all get along well.

Over the past several days I’ve done a number of interviews with candidates. One thing I’ve been struck with are the vast differences between those who prepare for an interview and those who don’t. Here’s some advice that I gave a college-age person yesterday (she was interviewing for a college intern position). Before you interview, learn about the person that is going to interview you. With all of the resources of the web, you can find out a lot about me pretty quickly; where I’ve worked, my professional experience etc. But more importantly, you can find out personal things about me. What makes me tick? Do we share the same interests? Do we know anyone or anything in common? These are critical things to learn BEFORE the interview so that you can not only make small talk but you can “get inside my head.”

Let me contrast this to a person that I’m going to interview in the next hour. I’ve never met this person, but already I’m impressed. Not only did she take the time to learn our product (she provided a great summary of things she liked/disliked) but she followed that up with a clarification email a day later. AND…. yesterday she posted a thoughtful and interesting comment to a recent blog post I wrote. I don’t know if she’s done her research on me, but my guess is that she’ll be prepared.

So how do you prepare for a interview? Spend time showing your interest and thoughtfulness. Learn about your interviewer (especially things that make that person tick). And when all else fails, learn the product inside and out.

To the college student who wasn’t prepared: I sincerely hope that you’ll take this advice and use it in the future. There’s simply no substitute for preparation before an interview.

To the person who I’m interviewing at 11am: I look forward to talking with you. You’ve already demonstrated a keen level of thinking that we look for in the people we like to hire. Smart. Very smart.