Why the ‘Best User Experience’ MITX award means so much

Last night at the 2015 MITX awards, Punchbowl won the award for ‘Best User Experience.’ This award meant a lot to me — let me tell you why.Screen Shot 2015-05-15 at 7.19.11 AM

On February 25, 2014 (15 months ago, and just days before my second child was born), I held an offsite meeting with key members of the Punchbowl team. At this “eTeam meeting” I brought up a radical idea: what would happen if we removed 50% of the features in our product, drastically simplified the user interface, and focused the product on our core offering of digital invitations? After several hours of discussion, “Project Megadeth” was born.

For the next several months, I worked on strategy with close advisors and mentors. We worked through some of the tough business issues, thought hard about tactics, and plotted a plan of attack. A few months later, our product team had cleared their plate and was ready to go. In June 2014 at our Q3 kickoff meeting, I unveiled the bold plan to the whole Punchbowl team, and we set out on the most ambitious project in the history of the company.

Every day, for weeks and weeks on end, our design and product team met. Lead by our Director of User Experience, we explored, iterated, designed, thrashed, re-designed, and iterated some more. We built from the ground up with tablet and mobile phones in mind. Seven years of experience paid off, and eventually we had a design that we believed met all of our objectives. Our development team dove headfirst into implementing the design, and within a few months we began to see the new user interface come to life.

However, with any radical new design, there were several challenges. Our CTO is fond of saying “a spec is just a suggestion” and in this case it was definitely true. There were several issues that we had to solve during the implementation phase, as we balanced simplicity with powerful features. One example: we wanted to preserve our ‘Potluck’ feature, but we didn’t want it to be a required step for every user. We solved it by branching the feature from the ‘Invitation Options’ page and creating a mini user workflow for creation and editing. Sounds simple, but the devil is always in the details.

On October 20, 2014 we launched the new site. The response was overwhelmingly positive, and we were really excited about early usage. Over the next few months, we measured conversion and improved some of the user interface based on the metrics. We saw incredible growth, especially in our kids birthday segment. We knew we had a winner on our hands.

Fast forward to May 14, 2015: it’s now been well over a year since that fateful meeting with my eTeam. And yesterday afternoon, I had the opportunity to demo our fantastic product to a group of MITX judges. Several hours later, I sat with over 1200 people at the MITX awards ceremony. The event was elaborate and very fancy — and for the companies nominated, it felt like the technology Academy Awards.

When they announced the winner in our category, I pumped my fist and thought about the hundreds of hours that we spent designing and implementing the new user interface for Punchbowl. And I thought about the awesome people on the Punchbowl team, and just how very far we’ve come. I jumped up on stage, took the microphone as the lights shined brightly in my face and said  “Here’s the thing about great UI:  we spent literally hundreds of hours making a website that works on mobile, works on tablet, works on desktop and when you use it, it just feels like it works. I’d like to dedicate this award to every single entrepreneur who is not getting the notice that they deserve, who are taking one little step at a time, which is what we’ve done for the last seven years. So to the Punchbowl team, to Devin, to Blake, to Ryan, to Stephanie, we did it baby – let’s go!” (video of my acceptance speech below)

SWAMI SAYS: Some awards are just marketing gimmicks — and some awards mean a lot. The MITX award for ‘Best User Experience’ means a lot to me and the Punchbowl team. I’m very thankful and proud of the award.


My first boss: a tribute to Ben Lenz

This past weekend, I learned the sad news of the passing of Ben Lenz, a life-long family friend. Ben was the step-father to my brother’s friend Robert. Ben and his wife Pam (and her children) lived down the street from mine in the small town of Sea Cliff, NY. For many people, Ben was best known as the leader of the North Shore High School Explorers’ Club — for me, he was the first boss I ever had.Ben Lenz Bus

Ben Lenz was one of the most quirky, interesting people you could ever meet. No strike that — Ben defined the word eccentric. With his bushy gray curly hair, a cackling laugh, and his endless stories, Ben was a presence. He was very tall (probably over 6 foot 4) and the upper half of his body seemed to lean towards you [edit: according to his family, he wasn’t actually this tall. He just looked that tall to me!]. His gait was marked by a shuffle and a limp. Later in life, he used a cane as a walking stick. He drove a dark yellow VW bus, which he had converted into a camper.

In the mid 80’s, Ben decided to build a garden in his sprawling back yard. This was not just any garden. It was a Japanese inspired garden that was a tribute to his wife Pam. The garden had plants from all over the world, water features, sculptures, windmills and much more. He named the garden “Pam-Ben-monium” – and it was.

Sometime around the 5th or 6th grade, Ben offered me a job helping him with the garden. I’m not sure how this came to pass, but I loved the outdoors and probably was hanging around near the Lenz’s house anyway. He put me to work right away, and boy oh boy did we work. We moved huge rocks, dug dirt, and weeded on our hands and knees for hours under the hot sun. Ben barked out orders, and set the expectation early on that he wouldn’t put up with any complaining. He believed in hard work.

Ben had his own vision for the Pam-Ben-monium garden, but he also solicited my opinion. Without hesitation, he agreed to implement a few of my ideas. As a 10 year old, I welled with pride as I saw the newest waterfall in the garden take shape. For years afterwards, I thought I would become a landscape architect. I still love to garden.

Without fail, we always ate together after we were done with work. We would climb down rickety stairs into the basement, where Ben kept his “emergency pantry.” The shelves were lined with cans and cans of food, and he would choose one for our meal. Then, we would climb the wooden front stairs (even more rickety, the whole staircase leaned towards you) up to the kitchen and ate like we were camping. He asked me questions about school, baseball, and my brothers. And he was genuinely interested in my answers.

I saw Ben Lenz sporadically over the past 20 years, usually at my brother’s house. He remained as eccentric as ever, with stories to tell of his latest hiking expedition or special project he was working on. He always greeted me warmly, with his large hand firmly gripping mine as if to remind me: don’t forget where you came from. The last time I saw him he told a tale of a horse that had escaped from a barn: I don’t remember the details, but I remember his hearty guffaw and deep broad smile.

I didn’t know it then, but Ben Lenz taught me several life and work lessons that I still keep with me everyday:

  1. There’s no substitute for hard work
  2. Have a vision, but don’t be afraid to implement other people’s ideas
  3. There is deep joy to be had by getting your hands dirty with the earth
  4. After you work hard, make sure to eat
  5. Keep emergency supplies in the basement
  6. Eccentric is what makes you memorable
  7. Invest in young people: the impact you make will far surpass your expectations

Ben Lenz died on March 4, 2015. As my old friend Ted pointed out, the date of his passing sent one last message: march forth. I think he would have liked that as the epilogue to his life’s story.

SWAMI SAYS: Rest in peace, Ben Lenz. May your soul live on in all those you have touched, and may you find endless pandemonium in the great beyond.

How to Kick-off the Year Right

start_the_new_year_off_rightLast week, I wrote about how I spent the last few weeks of December working through our strategic plan for FY2015. As I started the new year, I felt prepared and confident about the road ahead. But when you run a company, it’s not good enough for YOU to understand the plan. Your most important job is making sure ALL of your employees and contractors understand the plan too.

To kick-off the year right, I think there are four things that you have to do:

1) Preview your plan with a few employees: When you kick-off the year, you want to make sure that you have a few people in the room that have heard part of the story ahead of time. Choose a couple of people from your organization, and tell them a little about the plan. In my case, I made sure that the Executive Team was all on the same page, and I spoke ahead of time with a few other people. You don’t need to provide all of the details in these meetings. Just share enough so that the important pieces aren’t a total surprise to everyone in the room. This will go a long way towards helping you build consensus and momentum among the whole team.

2) Hold a kick-off meeting: At Punchbowl, I hold kickoff meetings for each quarter. But none is more important than the fiscal year kickoff. I spend several weeks preparing for our yearly kickoff meeting, and I think about the kinds of questions that I might be asked. The kick-off meeting is important to me as a leader, and I know that employees value it too. Consider this feedback I got recently from an employee, “Our quarterly meetings are one of my favorite things about working at Punchbowl. After working for a company where the priorities were never articulated, and I never understood the motivation behind any major decisions, this time we spend together as a team, getting on the same page, is something I really value.”

3) Set the company bonus: Once you communicate the strategy for the year, I believe it’s important to set a bonus for employees that aligns with your strategy. At Punchbowl, we offer a cash bonus of 10% of your base salary based on achieving the goals. I split the bonus between the quarterly priorities (50%) and year-long goals (50%). For each quarter, there are 3 business priorities and 3 product priorities. That’s a total of 24 priorities for the year. In addition, we set out ambitious objectives based on our company’s strategy. This methodology helps align what employees do everyday with their bonus, and also ensures that employees succeed when the company succeeds.

4) Ask for feedback: The last part of your kick-off plan is to ask your team for feedback about the kick-off meeting and strategy. Include questions like “What did you think of the kick-off meeting? Are you clear on our fiscal year strategy? Why or why not?” and “What components of our strategy are you most/least excited about?” You’ll find that certain people who don’t have much to say in a group setting have a lot to say over email. And you’ll also see commonalities among what people think. Finally, it’s an opportunity to learn what parts of your strategy still need to be emphasized in future team meetings.

SWAMI SAYS: As a small company CEO, it’s critical to kick-off the year right. If you follow my plan, you will have everything you need to get your team on the same page and be successful for the year. As I write this post, it’s still early January — so it’s not too late to kick-off the year right. There’s nothing else on your plate that’s more important.

The most wonderful time of year (to work)

Wonderful time of year imageThe past couple of weeks have been busy with Christmas, and New Years Eve holidays. It’s the time of year that lots of people take time away from work, and email inboxes quiet down. Many of the days around the holidays have fewer people in the office, and there are very few scheduled meetings. It all can amount to a unproductive environment at work.

And yet, for me the holiday weeks have always been some of the most productive times of the year. I relish the days where I don’t have any scheduled meetings, there are fewer emails to respond to, and I can focus on the big picture. For this small company CEO, these past couple of weeks are critical to success in the new year.

I’ve spent the time working through our strategic and financial plan for year ahead. I’ve pored over financials, dug deep into the strategic possibilities, and had long conversations with advisors and mentors that I trust the most. I’ve read business related materials that have helped round out my thinking, and I’ve had quiet time to contemplate the year ahead. Indeed, for me it’s the most wonderful time of the year to work.

This first week of the new year, I’ll meet with the whole Punchbowl team to unveil the fruits of my labor: a well-thought out strategic roadmap for the year. It includes not only a clear description of how I made decisions, but also a product and marketing roadmap for the year. While I can’t predict whether or not the plan will be well received, I can be assured that I’m well prepared and that the plans have not been made rashly.

Even though I’ve worked most days over the holiday period, don’t be mistaken. I also had lots of time with my family, and plenty of time to see friends. But I was in the office on all of the work days, and spent evenings and some of the weekend at home thinking about work. I never shut off work like I do on vacations.

I’m not a fan of cold weather, and I would gladly trade one day in the summer for two days working in the winter. I’d rather work hard during December, January and February than during beach weather. I look forward to this coming summer when I’ll take a couple weeks off and enjoy the weather. That will be my reward for working hard through a time of year that lots of people shut it down.

SWAMI SAYS: Did you take a lot of days off this holiday season? Next year, consider working as much as you can during the holidays, and taking more time off during the warm summer months. You’ll start the year feeling ready to go and fired up.

Roy Hobbs, Single Malts, and Destiny’s Child

Over the years, I’ve been interviewed many times for various publications. The most recent time was this week when I was interviewed for an article that appeared on BostInno. It’s sometimes hard to convey who you really are when you are asked a series of seemingly random questions — but I thought the questions and my answers in this interview provides nice insight into how I think and what matters to me. Special thanks to Connor Barnes and Linda McDonough of Cassidy Turley Boston for the opportunity. You can read the entire interview on BostInno, and I’ve chosen my favorite questions to re-blog here. Enjoy, and let me know what you think.

If you could have had the starring role in any movie, already made, what movie would it be?

MjD: Well, the obvious answer would be Groundhog Day and I would love to play Phil Connors. The scene where he drives down the railroad tracks, gets stopped by the police, and proceeds to order fast food when he rolls down the window still gets me every time. But I think the movie “The Natural” would fit me better: a total unknown comes out of nowhere and possesses unbelievable talent. I’d like to think of myself as a modern day Roy Hobbs in the tech startup world: no one believed I could build a company from nothing, but here I am. Above all, I’ll have a huge love of the game of baseball, and in my opinion “The Natural” is the greatest baseball movie ever made.

What do you do for fun?

MjD: I have two kids now, and I spend most of my time with them. Those who don’t have kids will never understand the unbelievable joy you can feel showing them something new for the first time. Last weekend, I took my 4-year-old daughter to a local pond and we set sail using my inflatable raft. Splashing each other with water as we paddled around was more fun than I could possibly describe. I’ve also developed a habit for great beers and whiskey. It’s lots of fun to taste new craft brews and single malts. And the more you taste, well… it gets more fun.

What is one thing the startup scene is missing in this area?

MjD: The startup scene is missing enough early-stage investors who can suspend their disbelief of new entrepreneurs. We almost didn’t get funded simply because I didn’t have a track record of startup success. Meanwhile, second-time entrepreneurs are getting silly, ridiculous money for bad ideas simply because they had some success in the past. We need more investors taking risks on first-time entrepreneurs with good ideas.

If you had a theme song that played every time you walked into a room, what would it be?

MjD: Probably the chorus of the song “I’m a Survivor” by Destiny’s Child. The lyrics “I’m a survivor, I’m not gonna to give up, I’m gonna to work harder, I’m gonna make it” are all you need to know about me. I may lose a given battle, but I’m not going to lose the war. And I have a very long memory for people who stand in the path of my success.

Who is the most fascinating person you know?

MjD: On the street where I live, there is a man who walks to the train at exactly the same time every morning like clockwork. He wears a fedora and carries a briefcase, looking straight ahead with no expression on his face. In the evening, he comes home at exactly the same time every day, briefcase in hand, with barely a nod to people he passes. One day, I stopped him to say hello and asked him what he does for a living. He told me he’s an engineer for Verizon and his primary job is maintaining code for landlines using an outdated language called Cobalt. He’s worked at the same job for 30+ years. Here’s why I’m so fascinated: this man is the polar opposite of me. I can’t imagine doing the same job for 30 years, working on outdated technology in a declining market. This guy clocks in and clocks out, happy to collect a paycheck and inch his way towards retirement. The mindset of someone like that is fascinating to me.

Any advice for the young entrepreneurs out there?

MjD: Here’s what I wish someone had told me: as a young entrepreneur, your instinct is to solicit advice from those who have been successful and those who might know something about your market. This is a great way to meet a lot of people and grow your network. But don’t mistake their quick take for anything more than a 15-minute look into your world. They don’t understand the nuances as well as you do and they don’t understand the context as well as you do. So while it’s important to surround yourself with people who can help, it’s more important to listen to your inner voice. Look deep inside and ask the question “what do I really think?” You see, it doesn’t really matter if you’re right or not. What matters is that you have the conviction to keep going, to not give up, and to learn along the way. Successful entrepreneurs listen to their inner voice more than they listen to the opinions of all of the people around them. The first step to success is to truly believe in yourself.

Eight years ago today, we incorporated Punchbowl, Inc.

It’s April 11, 2014 — which means that eight years ago we incorporated Punchbowl, Inc. as a Delaware company. I’m always nostalgic on April 11th, thinking about how far we’ve come as company and how far I’ve come as a entrepreneur. On a day like today, I wish I could reach back into the past and talk to Matt Douglas of 2006.


Matt signing the original Punchbowl incorporation papers

If I could talk to Matt in 2006, here are eight things I would tell him:

1) Your team is everything: You won’t get very far with this company without a fantastic group of people with you along the journey. Hire slowly, and fire fast. Pay close attention to what makes each person tick. Some of the people around you will become life-long friends.

2) It’s going to take longer than you think: Everything is going to take a lot longer including developing the product, raising money, hiring a team, and growing the business. Starting a company isn’t a short-term affair. Be prepared for a very long ride.

3) Starting a company is full of heartache: The road you’re about to embark on will be a very tough journey, and you’re going to feel deep sadness and heartache along the way. You’ll be betrayed, tricked, and ridiculed. But just know that around the bend is another day, and it does get better.

4) Don’t compare yourself to others: Oh, this is so hard. But it’s critical to your sanity. You’re going to see other companies get more funding, and other entrepreneurs start numerous companies while you’re still working on this one. You’ll see CEOs with more Twitter followers and startups with more users. Remember, you can only control your small sphere and you’ll drive yourself crazy trying to keep up with others.

5) Don’t worry about the competition: You can spend lots of time worried about what your competition is doing, or you can focus on what you can control. Hire a great team, build a great product, and focus on revenue and costs of your own business. The competition will come and go, but you control your own destiny.

6) Raising money is very, very hard: It’s difficult to put into words just how hard it is to convince people to part with their money and invest it in your company. Until you get the check in the bank, anything can happen. The key to success is presenting the company as an investment opportunity. Remember, people have lots of places they can invest their money. Find ways to get people truly excited to invest in your company.

7) Survive and advance: Like the NCAA basketball tournament (“March Madness”) it doesn’t matter how you win — just find a way to survive and advance. When you look back, the details will be fuzzy, but what you will always remember is that you found a way to survive. And that’s more than most entrepreneurs can say.

8) Form your own opinion: You’re going to be surrounded by lots of so-called experts along the way. Listen to what they have to say, but make sure you form your own opinion. It’s their 15 minutes of advice, but it’s your company. And you have to live with the decisions.

SWAMI SAYS: They say Rome wasn’t built in a day, and neither are successful startups. In fact 99% of successful startups grind it out every day and wake up many years later just hoping to have seen some success. Today, I’m going to pause for a moment to celebrate just how far we’ve come. What a ride it’s been!

Six Things I Want to Teach My Dog about Work

Dharmesh Shah recently wrote a blog post about the lessons of entrepreneurship that he wants to teach his son called “12 Things I Want to Teach my Toddler about Work.”  It was an neat post which offered his typically pithy insights, with the twist that it was directed at his three-year-old son. After reading the post, I started making my own list of things I would like to teach my four-year-old daughter. I came back to the list recently to add a few items. As I was making notes, my dog Roxxee interrupted, and wanted me to take her for a walk. In typical fashion, she sauntered into my office and with her tongue sticking out and her tail wagging so hard it hit the walls.

So I took her for her afternoon walk and the fresh air gave me some new perspective. As we walked (and I spoke to her), I thought to about the things that I wish I could teach my dog about work . (In case you’re wondering, yes, I do talk to Roxxee as if she would respond to me). In the five years I’ve been bringing her to work, she’s heard and seen EVERYTHING at my office. Here are six of the most important things I want to teach my dog (and my readers) about work:

1. Always be loyal – In the business world, loyalty is arguably the most important trait. Roxxee is usually loyal, but sometimes she can be distracted or lazy. At times, she can appear like she just can’t be bothered (like when I tell her it’s time to go home at the end of the day). Employees look for loyal employers and partners look for loyal counterparts. Don’t let complacency or laziness get in way of always being loyal to your colleagues and partners. If you get a reputation of not being devoted and steadfast, no one is going to want to work (or play) with you.

2. Greet everyone in the same way – This does not mean sneak up behind your guests to sniff their…uh…shoes. It means welcome your guests and greet them all with the same level of energy regardless of how tired you are or how tasty the bone you’re chewing. You never know if the person you’re greeting is going to be someone important in your life (or perhaps your new dog walker). Make that first impression really count.

3. Focus on long-term goals (not just short-term ones) – Roxxee (like most dogs) has a one-track mind. She’s does what she has to in order to get treats. But unlike this Pavlovian response, building a company is a series of short-term goals (i.e. treats) that lead to long-term successes. Real progress isn’t accomplished by only achieving short-term goals. You’ll find success by viewing those short-term goals as stepping stones to larger, more meaningful goals down the road. Don’t just focus on the treats!

4. Get fresh air everyday – One of the reasons I love having Roxxee in the office is because she forces me to take a break in the afternoon. But I don’t check  out from work on those walks. The fresh air wakes up my mind and helps me think differently. I usually ask if anyone wants to catch up with me and they join me on a walk. The fresh air helps foster some great conversations. Whether you have a dog or not, I recommend stepping out of the office at least once a day to get some fresh air.

5. Sleep when it’s time to sleep, work when it’s time to work – Roxxee often sleeps most of the day away, and if she were an employee that would be a serious problem. To be productive, everyone needs to get 6-8 hours of sleep every night in order to be ready for work. My worst days at work are when I’m tired and sometimes the only solution is sleep. Rather than continuing the vicious cycle, the best way to be productive is to reset your body so that you can work efficiently. And when it’s time to work, you need to be alert, engaged and ready. Roxxee might need to learn to sleep a bit less during the day.

6. Only wag your tail when you mean it – Like most dogs, when Roxxee is happy, she wags her tail. It’s her way of telling someone that she appreciated a treat, a walk, or a pat on the head. But sometimes Roxxee wags her tail as an innate reaction, and not as a response to something positive. I think it’s important to provide positive feedback to employees, but not unless you really mean it. Too often managers provide positive feedback for insignificant and inconsequential milestones. It’s important to only recognize meaningful moments so that employees know what matters and what doesn’t.

SWAMI SAYS: They say that dogs are “man’s best friend” — and Roxxee is no exception. I treat her like a member of the team at my company. And while she’s an important fixture in the office, she could stand to learn a few things about work. Can I teach this dog some new tricks? Probably not. But perhaps the things I would teach her might be helpful in your startup or company.

Matt Douglas is the Founder & CEO of Follow@mattdouglas on Twitter. 

5 reasons you must repeat your strategy

Every great company or organization should have a high-level strategy that can be explained in two minutes or less. A company’s strategy is the blueprint to success, and a great strategy helps connect every single employee to the vision of the company’s growth.

A strategy is not a mission statement. A strategy is a clearly-defined path to growth and financial success over a set period of time. Your strategy should explain how you acquire customers, how you monetize them, and the key differentiators of your business. In short, your strategy is the reason that you’ll be successful in the market. (more…)

5 Advantages of Starting a Company in Metrowest

This article first appeared on on August 1, 2013 as a guest post. Matt Douglas is the Founder & CEO of Follow @mattdouglas on Twitter. For every new follower this year, Matt is donating $0.25 to

If you’re starting a tech company in Boston, most people assume that you’re thinking about locating your office in either Cambridge or in downtown Boston. The argument is that those areas are the tech hubs of the city, and you would be a fool to plant your company anywhere else.

In Silicon Valley (where I lived in the late 90s), there are companies both inside and way outside of both San Francisco and San Jose. Lots of people live in places like Palo Alto or Redwood City and commute to either city — and vice versa. The whole area is considered part of Silicon Valley. But here in the Boston area, unless your company is located in Cambridge or in downtown, it’s considered way outside of the major tech area. We need to change that perception. (more…)

Twitter syntax is important

tweet-meThis week, I started more actively building my brand online. As part of my strategy, I announced on my blog and on Twitter that I will donate $0.25 for every new Twitter follower that I get this year. And in the first day, a few prominent people helped by re-tweeting. I grew my Twitter following 10% in one day. I’m starting with a fairly small base, but that’s progress.

In the process of tweeting, I’ve already learned a few syntax things about Twitter that are useful as I spend more time on Twitter (hat tip to @adamrubin for his clear explanations): (more…)