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.


First time entrepreneurs should avoid two-sided marketplaces

marketing-challengesIf you are thinking of starting a company, there is one decision that you need to make right up front. Are you trying to create a product or service for one market or are you going to attempt to create a two-sided marketplace? Most of the products and services that we use are one-sided. A company builds a product that certain users demand. A two-sided market (e.g. marketplace)  is one that requires demand from TWO different types of users. That’s really tough to build.

I didn’t know it at the time, but I made a smart decision when I started Punchbowl. Although I had ideas about how to create a two-sided marketplace, we’ve created a product that is fairly simple to market and grow. To be successful, all we need to do is to get more people to plan an event. We’ve tested some ideas around creating a two-sided marketplace, but our bread-and-butter is a simple one-sided market.

Two sided marketplaces are very difficult – they suffer from the “cold-start” problem because you need demand from two sides. Most of us know the “original” two-sided online marketplace: CraigsList. When CraigsList started, the site needed both people wanting to sell things and people wanting to buy things. In the early days of the Internet, this wasn’t a sure bet. But CraigsList was able to create demand on both sides of the market with a simple user interface and by being one of the first to market. And it didn’t hurt that it was free!

Here are a few other two-sided marketplace examples:

  • eBay (EBAY): Needs both people who want to sell things, and people who want to buy things in an auction style.
  • Homeaway/VRBO (AWAY): Needs both people who have vacation homes that they are willing to rent and consumers who are looking to rent vacation homes.
  • (CRCM): Needs both families in search of child care providers, and people who are seeking child care jobs.
  • The Knot (XOXO): Needs both brides seeking DJs, caterers, and bakeries and local vendors who offer their services for the wedding market

Several times a month, an entrepreneur reaches out to me to get my take on their startup. And more often than not, I’m being pitched a two-sided marketplace. Here’s the problem: to create a two-sided marketplace, that means you need to do TWICE the amount of marketing to be successful. And while two-sided marketplaces can be very lucrative, more of them fail given this intrinsic challenge. If you’re a first time entrepreneur, I would strongly recommend that you build a company for only one market, and leave the more difficult two-sided marketplace for your next rodeo.

SWAMI SAYS: Starting your first company? Don’t try to build a two-sided marketplace. It’s difficult enough to build a great team, get your product to market, and find users. If you’re successful building your first startup, you’ll have the experience to try and build a two-sided marketplace. One last thought: successful two-sided marketplaces can be very lucrative. All of the companies I listed above are publicly-traded companies. Take a look at their financials and quarterly reports to learn more about what it takes to build a successful two-sided marketplace.

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.

Just pick up the f*#@ing phone

Like most people, I send dozens of emails a day. Pretty much anything that I work on can be dealt with using email. But is that always the right choice? Most of the time, the communication is simple and requires a simple answer so email is a good choice. Other times, emails fly back and forth, sometimes spanning an entire week, before any resolution. I’m shocked at how much time is wasted, and how much can be lost in translation. Email replies become long chains, hours become days, and progress is slowed to a crawl. Which begs the question.. why didn’t we just pick up the f*#@ing phone?

On March 10, 1876 (138 years ago!), Alexander Graham Bell successfully called his assistant, Thomas Watson and said, “Mr. Watson — come here — I want to see you.” In that moment, he enabled us to make an instant connection, wherever we are, with anyone we want. We forget that the ability to make a phone call is something miraculous. The phone is still the way big business is done and how major deals transpire. Ask any investor, investment banker, or CEO and they will tell you that for most of the significant deals in their career, the telephone played a critical role in communication.

I get it — not everyone likes to talk on the phone. There are niceties to be exchanged, needless small talk, and awkward silences. However, if it’s important and time-sensitive, calling someone to hash it out is so much easier than the inefficiency of email. Countless times a month, I’ll challenge one of my employees who is having trouble making progress. I’ll simply ask “well, did you call them?” (What I’m really thinking is “why didn’t you pick up the f*#@ing phone?”)

Screen shot 2014-05-28 at 3.55.24 PMHere are four situations where a phone call could accelerate your progress:

Situation #1: You are knee-deep in legal documents, and have gone through several iterations of changes. You’re sending ‘track changes’ back and forth with your comments, but neither party really understands the reasons for the changes.

Solution: Just pick up the f*#@ing phone. Spend one hour hammering out all the changes together and be done with it.

Situation #2: You’re working on a new business deal. You have a proposal in place, but there’s a significant gap in your partner’s understanding of the product. They are asking questions, but all of the questions are a little “off” because they don’t understand some basic things.

Solution: Just pick up the f*#@ing phone. In a matter of minutes, you can educate the partner about the product and get over this hump. Time is money so get on the phone and fast-forward the partnership.

Situation #3: You’re raising money for your startup, and you haven’t heard back from an investor who has expressed interest. How do you get a firm commitment?

Solution: Just pick up the f*#@ing phone. Raising money is a sales job, so do the hard work. Pick up the phone, call until you reach the person, and ask for the sale. I’ve raised hundreds of thousands of dollars just by picking up the phone and being persistent. You can too.

Situation #4: You’re hiring a new employee. After a few rounds of interviews and some internal conversations, it’s time to make the offer. Yes, you can send an offer by email, but you really want to convey how much you want them to join the team.

Solution: Just pick up the f*#@ing phone. Call and personally ask the person to be a member of your team. It will differentiate you from other employers and set the tone that you really care about them as a person. You’ll be surprised at how much of a difference this makes in the final stage of recruiting.

SWAMI SAYS: Email is great for lots of communication, but sometimes the most efficient solution is to pick up the phone. Don’t hesitate to call someone to work out the hard parts, and leave the simple stuff for email. Make a personal and instant connection via phone, and watch how you much more you can get accomplished. Just pick up the fucking phone!

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!

The ‘flyover’ states

Like most startup CEO’s, I spend most of my time dealing with companies on either the East Coast or the West Coast. Between Boston and New York on the East Coast, and San Francisco, Silicon Valley, LA and Seattle on the West Coast there are a lot of potential partners for a business like Punchbowl.


However, over the last year, I’ve noticed an increasing number of potential partners and big customers  that are between the coasts. I’m talking places like Idaho, Missouri, Indiana, and Minnesota. In fact, I spent several hours last week talking with a couple of companies in the Midwest that are several billion dollar companies (yes, that’s billion). And guess what? Many of them talk about their strong customer base in the middle of the country.

Those of us on the coasts tend to forget that there are a lot of people who live between the coasts. The wonderful thing about the Internet as a marketing channel is that you can reach them just as easily as the people on the coasts. You don’t need to get on a plane or spend thousands of dollars on billboard ads up and down the interstate. doesn’t care where you live (and we love our international customers too!). (more…)

Chicken Soup for the Entrepreneur’s Soul

A few weeks ago, I had a meeting that was supposed to be uneventful, but it left a lasting impression. The meeting was with the CEO of a small company in downtown Boston. On my drive into Boston (about 25 minutes) I reflected on how much I value these kinds of meetings. In this case, it had taken a few months for us to find a date that would work for both of our schedules. I looked forward to meeting this fellow CEO.

When I walked into the company’s offices, I was immediately impressed. It was the kind of office that says a lot about the company: modern conference rooms, open-style workstations, colorful walls, and a whole lot of smart-looking people that looked genuinely happy to be at work. The CEO took me for a tour of the facilities — which included a design firm that worked within the company (not affiliated, they just shared space), and an artist-in-residence (you know, the kind that actually paints art). Very cool. (more…)

All because of George

If you have lost your faith in humanity and the goodness of people, read this story. It happened to me and my family today, and I’m still shaking my head in awe.

Today, my wife and my 3 1/2 year old daughter were headed up to a lake in NH — somewhere in the middle of the state. We chose a route to avoid traffic, and found ourselves cruising along the highway sometime around 2pm about 70 miles from home. All of a sudden, I noticed white smoke blanketing the highway behind us. I assumed it was another car, but my wife quickly pointed out that it was coming from our car. I had no idea what was going on, but it was clear that we needed to pull over right away.  (more…)

Change one word and improve your conversations

A very wise person taught me an important lesson several years ago:

Rather than saying “but”, try saying “and” instead.


I remember when I first heard this advice, my first reaction was that this was another one of those trite phrases that people like to say sometimes. However, I really trust the person who shared his wisdom with me, so I took the time to carefully listen to his perspective. (more…)

The 24 hour challenge for job candidates

Matt Douglas is the Founder & CEO of Follow @mattdouglas on Twitter. For every new follower this year, Matt is donating $0.25 to

Every month, I spend a significant amount of time interviewing candidates. At Punchbowl, we hire full-time employees, independent contractors, and interns. Regardless of the position, all of us work together as a close team. So it’s critical that we hire people that fit the culture and vibe.

I’m fond of saying that ‘good’ people are relatively easy to find: place an ad in Craigslist or and you can find educated, experienced, and talented people within days. But finding truly GREAT people is really hard — how do you find people with superb communication skills, a strong work ethic, excellent personal traits, combined with a willingness to join a small company? And how do you make sure that the skill set and mindset of this new person will be additive to the team you already have in place? I can tell you from experience: hiring great people is very hard.

Over the years, I’ve developed a sequence to my hiring process to find great people. My goal is to learn about the person as much as possible before offering a position. I want to know how they think and what makes them tick. One part of my process is something I call the “24-hour challenge.” (more…)