MyPunchblog

What makes something the brutal truth? In my opinion, the difference between the “truth” and the “brutal truth” is that the other party doesn’t want to hear your perspective. There’s an inherent resistance (and usually vested interest) by the other person to live in their world, even though an objective 3rd party would likely disagree with their point of view. The brutal truth confronts the situation head-on with the hope that it will help set everyone on a better path.

I’ve been in a few situations recently where I decided to tell the brutal truth.

The first situation happened at work. We’re working on a new feature for MyPunchbowl, and it’s been progressing steadily. The lead developer on the project has been working hard over several weeks to hit the deadline. It hasn’t been an easy project, and there are multiple pieces to coordinate. He’s making progress, but it’s going to be a close call whether it will get done on time.

Last week I had the chance to see how the feature is coming along. The developer gave me a quick demo, and I was happy with the functionality and how the project was coming together. There was clearly lots more to do, but I could see how it would be a great feature for our site. However, there was something really wrong with the new feature: it was ugly. Really ugly.

Here’s where the brutal truth came in: despite the look in the developer’s eyes and the approaching deadline, I had to tell him that the feature was simply ugly. I specifically explained why I thought it did not meet our standards for shipping a great product and I asked him and our lead designer to revisit the visual look of the feature. It was a hard conversation. As much as I wanted to tell him that the feature was almost done, I knew that the brutal truth would lead us to a better end result.

I had a similar situation recently with a family member. This person is having a hard time, and is going through some personal problems. Unfortunately, a similar situation has happened in the past and the most latest episode is almost a carbon-copy of before. As hard as it was to do, I believe that telling the brutal truth was the best way to deal with the situation. Others around me felt that we should be careful to not upset the situation more by highlighting the similarities, but I knew in my heart that it was time to confront this person. Sometimes hearing the brutal truth hurts. But I believe that by my actions to tell the brutal truth, the end result will be much better.

Try it for yourself: sometime this week tell someone what you are actually thinking rather than sugarcoat it because you’re afraid of their reaction. You’ll feel liberated by knowing that you’re helping to drive to a better end result more quickly.

They say that “the truth can set you free.” Perhaps, then telling the brutal truth “can set you and others free.”

Do you think telling the brutal truth is sometimes the best course of action? Why or why not? Please share your thoughts with me and others in the comments.

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.

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.

One of the hardest things about running a startup is keeping the focus on what really matters. Why is this so hard? Because on any given day you have to do all of the things that keep the startup engine running: finance, accounting, hiring, legal issues, taxes, investor relations — you get the picture. It’s pretty easy to get lost in all of that activity. It’s all important stuff, but how much of it really matters?

We’ve been talking alot about “what matters” inside of Punchbowl over the last few days. Our goal has been to identify the very few things that we believe can drive our business in the short-term. With our limited resources, we don’t have a lot of bandwidth to be spending on things that don’t really matter.

Here are a few questions that will help you decide if your startup is currently working on what ”really matters”:

1. As a company, what is your next important milestone?
2. If you are raising capital, what are the critical metrics and proof points that will help tell your story?
3. What are the revenue drivers for your company? (users? eyeballs?) How does your priority list directly relate to your revenue drivers?
4. Is your development team working on features that are “nice to have” or are they critical to moving the business forward?
5. What’s the most important thing you can do to grow your business?
6. Who feels the pain if you don’t do a particular item on the list? Your users? Your investors? Your employees?

It’s been an interesting few days as we’ve whittled down our laundry list of things we want to do to only the things that matter. The list above has been a useful tool for me as we’ve focused on what really matters.

If you’re in a startup: ask yourself the questions above. Are you currently working on the things that really matter?

I just found this gem from the blog of Mike Hirshland. Given that I come from a family full of MIT geeks, I just love this excerpt written by his partner at Polaris, Bob Metcalfe (this was apparently written as part of an article originally published in the MIT Technology Review in 1992)

“I am sad to find that the MIT culture,
at all levels, is still permeated with
the notion that professional salespeople
are properly placed in the food chain just
below green slime.
That attitude relegates too many MIT
students to bleak Saturday nights alone,
because they think it unseemly to do
the bit of selling conducive to lining up
a date….
And too many MIT entrepreneurs launch
companies that give no thought to selling
and so promptly crash and burn.
I can tell you firsthand that selling is
one of the highest arts in entrepreneurship.
Most companies, even successful
high-tech companies in Silicon Valley,
spend 10 times more on selling than on
engineering….
In short, nothing happens until something
gets sold.”

How true. Selling is what separates good products from great companies. I believe that MyPunchbowl.com is a great product– but it’s going to take selling to turn Punchbowl Software into a great company.

Read Mike’s full post — it’s worth a few minutes of your time.

I just came across a post by Fred Wilson (a NY based venture capitalist) that described how he is working on vacation.

I had a gutteral reaction to this post especially as Fred wrote about different ways to multi-task while on vacation. “A friend of mine listened in to a board call where he is an observer while skiing with his wife. He had the call on mute and the headphones under his helmet. We’ll have to ask his wife what kind of company he was on the hill that morning but that’s the kind of mutli-tasking we have resorted to at times.”

Oh Fred– as much as I respect you, this is wrong in soooo many ways. I believe the best way to take a vacation is to completely unplug and disconnect yourself from your daily routine. There are so many reasons to do this as a component of work/life balance; here are the most important ones:

1) It’s best for your colleagues: By remaining plugged in throughout your vacation, you’re not teaching your co-workers and colleagues to learn how to make tough decisions. In Fred’s case, he’s a valuable mentor to his portfolio companies. By not being available for a few weeks a year, you’ll help the CEO’s of your portfolio companies far more than by being involved in every decision. In some cases, the wrong decision will be made– but you know what? That’s ok. That’s part of the process for any CEO. Step away once in a while, and you’ll be rewarded by how self-sufficient your companies actually are.

Another note about this: In my experience, I’ve seen that the people who always stay plugged in are more likely to have trouble delegating responsibility than those who are able to step completely away once in a while. I’ve never worked with Fred, but I’m guessing that he may struggle at times with delegating tasks. By unplugging completely a few times a year, you’re training yourself to delegate. It’s a cathartic experience to step away from all decision-making for a handful of days. Try it once and you’ll be hooked.

2) It’s best for your family: I was struck by something that Fred wrote in his post: “The idea of a ‘get away from it all’ vacation is a romantic notion that I cannot seem to achieve as much as the Gotham Gal and my kids would like me to.” When you are constantly plugged in, you send the message to your family that you’re not fully engaged. They (obviously) want you to devote all of your energy to them, so they can feel in the hearts and minds that there is nothing that Dad would rather do than be on vacation with them. You can’t multi-task and effectively deliver this message. It requires truly “leaving it all behind.”

I’m sure that you would walk away from all of your work if something tragic happened to someone you loved. Don’t wait for that shocking phone call to change your behavior. You can choose to unplug and focus all of your energy now — and you’ll enjoy every minute of it more.

3) It’s best for you: When you constantly are plugged in, you’re always viewing the trees– and not seeing the forest. As we tackle challenges throughout our daily life, there’s a constant chatter of problem-solving going on in our brains. I find that it takes me a few days after the start of my vacation to remove all of the “trees” from my brain. Then, after a few days of mental quiet, I take the last two days of my vacation to think about “forest” items in my life. This is the true benefit of a vacation; to allow you to step away, quiet your mind, and re-emerge with new perspective and thoughts about life and work.

Too often in our lives we lose sight of our place in the world. Vacation enables us to reflect on how we fit into the world at large and examine the impact our daily lives have on the bigger eco-system around us. There’s no better feeling in the world than being able to recognize how it all fits together and then get back to the nitty-gritty tasks with that fresh perspective.

I recognize that people are different, and what works for one person doesn’t necessarily work for another. But I’ll tell you this: unplugging has certainly been effective for me: some of the best ideas for MyPunchbowl.com came to me sitting on a sunny beach in the last two days of my vacation.

So Fred: give it a try. Promise your wife and kids that you’ll unplug for one week. Leave the blackberry at home. Tell your colleagues and portfolio companies that you’re unavailable. Quiet the noise inside your head for the first few days, and then focus 100% on your vacation for the next few days. Then on the last days of your vacation, grab a good old fashioned pencil and paper and write down some thoughts, trends, and ideas that come to mind. Some of your best ideas will come from your vacation notebook — and you’ll look at it with awe in years to come.

Over the past week, much has been written about what it takes to build and run a successful startup. It started with a post from Jason Calacanis where he suggested 17 tips to save money while running a startup. In the article, Jason suggested that you should fire anyone who is not a “workaholic” (update: Jason has written more about what he meant to say). The original post caused quite a stir: first TechCrunch responded to Jason’s post by suggesting that Calacanis fires people who have a life. 37 Signals weighed in with their take on work/life balance. Then Allen at Center Networks provided his own perspective.

I’ve spent some time chewing over this bru-ha-ha this week. Although the controversy revolved around work/life balance, I sensed there was something deeper that was at the root of all of this dicussion– specifically, what does it take to build a successful startup? The reality is that startups are like snowflakes. No two are the same. Products are different, teams are different, market conditions are different, competitors are different, challenges are different. So what does it take to be successful building a startup?

Much has been written about this too: Arrington says that hiring is the thing that matters most. Dave Winer says it’s mostly about building a hot product. Tony Wright weighs in with a post that probably rings the most true to me: it’s different in every case.

As I digested all of these great points of view, and reflected on my own experience with MyPunchbowl.com I wondered if there was one piece of startup advice that was universal– something that everyone could agree on. Something more important than saving money, or working hard, or building a product that people really wanted. Is there some piece of advice that could trump all of these very important things?

I think there is. And it’s a pretty simple concept that is much, much harder in practice than could possibly be described in a blog: DON’T GIVE UP.

Don’t give up: when you’re all alone at the beginning, trying to figure out if there is a market for your product

Don’t give up: when all you have is a Powerpoint presentation and a vision.

Don’t give up: when you struggle to explain what exactly it is you are working on (chances are you’re not even really sure yet yourself)

Don’t give up: when you can’t find people to take a risk with you, to join you at the infancy stage of your startup

Don’t give up: when every VC you meet with says that the “market is too small” or “the competitive space is too crowded” or “they don’t see how it can become a 100M company. (Read Mike Feinstein’s post)

Don’t give up: when product development is going slower than you would like, when big bad bugs slow you down, and when the user interface still isn’t quite right.

Don’t give up: when your early beta customers tell you the 50 other things the product needs before they would actually use it.

Don’t give up: when the press (or bloggers) won’t cover your product or write about your latest development

Don’t give up: when potential partners don’t return your phone calls and show a mediocre interest in actually closing a deal

Don’t give up: when individual angel investors get cold feet before they write the check

Don’t give up: when you can’t find GREAT people to hire to round out your team

Don’t give up: when they tell you it can’t be done or it’s already been done — when they tell you to pick another market.

Don’t give up: when the competition heats up

Don’t give up: when others can’t see the potential that you do

Don’t give up: when others around you do.

To all of those who wrote about what it takes to build a successful startup, I challenge you: is there another golden rule of startup success that trumps my Golden Rule?

Whether you save money, build a hot product, hire the right people or fire the workaholics, I believe that the only thing that matters is that you don’t give up. This is something that can’t be taught: it’s like the Gatorade commercials: do you have IT in you?

If you’re trying to build a startup– or maybe you’re struggling to get it off of the ground I hope you’ll re-read this post when you feel like giving up. Then pick yourself up, dust yourself off, and get back to it. Little by little everyday. Just don’t give up, and the rest will take care of itself.

As we build MyPunchbowl.com, I remind myself everyday not to give up. That’s the only thing that really matters.

The last few days have been a whirlwind for the Punchbowl team. We’ve moved!

We’ve opened our new office in Framingham, MA just a few minutes away from the I-90 highway (for those of you not from this area, we’re about 30 minutes from Boston, without traffic). It’s a great location for our employees, and provides room for us to grow in the future.

The new office is pretty spacious and has a couple of great rooms: one we’ve nicknamed “The Bowl” and the other “The Cave.” I work in the Cave– despite it’s nickname, it has a nice window and lots of natural light. The Bowl is the main room where the real work takes place. We’re really happy with the setup and vibe of that room in particular.

We have plenty of space in the office, with room for brainstorming on the whiteboard and meetings. There’s also a “lounge” area which is great for lunch and impromptu discussions. We also have a conference room which we can use for more formal meetings with investors or partners.

There are a few other tenants in the building, and it’s a dog-friendly office. Don’t tell his owner, but we’ve adopted one of the other residents of the building… meet the newest Punchbowler (his name is “Mozart”):

If you’re a friend of Punchbowl (canine or otherwise), we hope you’ll get a chance to come by and see our new digs at some point. But make sure you come with a plant or other foliage in hand– we could use some!

The new Punchbowl office is located at 873 Concord Street, Framingham, MA 01701.

Party Planning and Online Invitations with MyPunchbowl

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

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:

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.

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:

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.

———

Party Planning and Online Invitations with MyPunchbowl