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.

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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 Punchbowl.com. Follow@mattdouglas on Twitter. 

It took me 25 years to meet Mickey Mouse

By now, hopefully you have heard the news — Punchbowl has been named the exclusive provider of digital invitations featuring Disney characters. To say I’m excited would be a gross understatement.

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This is the kind of deal that doesn’t come easily and requires many, many meetings. Over the past two and a half years, I’ve had countless phone calls and exchanged numerous emails with the folks at Disney.  I’ve gotten to know my counterpart at Disney very well through this process. And yet, I’ve never met him.

I’ve seen a picture of him online, and I’m sure he’s seen mine. We’re connected on LinkedIn, I have his cell phone number, and I know some details about his family. In the past few days, I’ve been on the phone with him several times per day as we prepared to launch this partnership. But we’ve never shook hands, shared a meal, or looked each other in the eyes. This significant deal was completed without ever meeting face to face. Like many people I do business with these days, neither of us felt the burning need to get together. Oh, we tried a few times. The latest attempt was when I was in Southern California for a conference. He even gave me a great tip about flying out of Long Beach instead of LAX. But our schedules didn’t align and I wasn’t able to stick around an extra day. “That’s ok,” we both agreed, we’ll catch each other next time.

Perhaps it’s fitting, because it took me 25 years to meet Mickey Mouse. Unlike many kids in America, I never had the opportunity to go to Disney World or Disneyland as a child. Of course I loved all of the characters, but growing up in a middle-class family with six kids it wasn’t practical to go on a Disney vacation. Many of my friends went, but I grew up without seeing the live Disney experience. That didn’t quell my desire to go.

In my mid 20s, I was living on the West Coast and my girlfriend (now wife) and I took a trip to Disneyland. I loved it. I’ll never forget seeing the Muppet Studios or flying on the California Dreamin’ ride (I even bought the soundtrack). A few years later, I went to visit my family in Orlando and had the opportunity to visit Disney World. I loved Epcot, the parades, and the rides. And I even got to meet Mickey Mouse up close and personal.

I hope it doesn’t take 25 years for me to meet the person at Disney who helped make this deal happen. As I’ve told him numerous times, I wanted this deal badly, and I did everything I could to get it done. In the new world of online business, he didn’t need to meet me to know that I am who I appear to be online. I’m a passionate entrepreneur who loves hard work and doesn’t like excuses. And I didn’t need to meet him to understand that he was looking for a great partnership with a company that has a best-in-class product and team. Together, we learned everything about each other without the need to meet face to face.

SWAMI SAYS: Big deals can happen between companies even if you never meet face to face with your counterpart. So it’s more important than ever to make sure that your digital persona matches who you really are in-person. In this day and age of business online, it’s a whole new world. It’s a magical world, where when you wish upon a star, sometimes dreams do come true. Check out the new Disney Digital Invitation Collection.

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.

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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. Punchbowl.com 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.

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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 Punchbowl.com. Follow @mattdouglas on Twitter. For every new follower this year, Matt is donating $0.25 to Water.org.

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 Indeed.com 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…)

7 Pithy Insights about Dharmesh Shah

Note: This is a refresh of a post that I originally wrote in 2007, but it was removed from the web when I created my new blog. Much of the content below is new.

Before I begin, a disclosure: Dharmesh is an investor in Punchbowl, an advisor, and a business friend. However, even though I know him fairly well, he remains an enigma for many people in the Boston startup community (and beyond). What makes this man tick? How does he churn out such great content, attract fantastic people to join HubSpot, and invest in so many companies as an angel investor? (more…)

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…)