In a little over 18 months, Gowalla worked with just shy of 70 major global brands to create incredible campaigns built around the experiences that their brand could uniquely curate around the places that people go. Here are a handful of my favorite partners that I had the chance to work with:

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Most people learn how to play a new game by having someone who has played before teach them. That is the fastest way to get the game going and then “learn as you go.” But, the fastest way to win, and then likely be called a cheater, is to read the rules.

Growing up, my family played a lot of games. Card game, board games, and guess which word I want you to say games. Each time that a new game was introduced, via birthday present or unsuspecting friend, there was a scramble to understand more of the rules faster than everyone else. Whether it was taking turns reading the side of the box, huddling around the small print pamphlet like it was the Dead Sea Scrolls, or reading all the rules before telling anyone else that there was a new game in the house, the rules were a big part of the indoctrination to the Ellwood family game night.

The reason for the clamor around the rules was quite simple: they tell you how to win. And, when it comes to games, that is the only reason to play. (The “let’s not keep score and just have fun” thing just doesn’t work for me.) The rules lay out what exactly you would do to win faster than others and says that these things are illegal. But, in telling you the things that are against the rules, it also paints the picture of what kinds of things should be paid attention to and the areas of the game that advantages might be acquired.

This weekend, the Sunday New York Times front page above the fold story featured a detailed look into the complex tax planning strategies of the hier to the Estée Lauder fortune.  The headline and the sentiment of the article do little to hide the author’s distain for the ways that Ronald Lauder and his family have structured their finances. Several times throughout the article there are references to his “shrewd use of the US Tax Code.” This is followed by general statements about the complexity of “labyrinth of trusts, limited liability corporations and holding companies” that may or may not have been developed to with their likely favorable tax implications in mind.

Looks like someone read the rules.

Looks like someone else doesn’t like the rules.

And while this article may serve as further proof in the case against the Haves being made by the Have Nots, I took it from a different perspective. What are the rules that I haven’t mastered? What are the advantages that exist in my world that I am not maximizing? What are the angles that I can take in the games I am currently playing that will frustrate others not clever enough to find them?

“If no one is accusing you of cheating, you probably aren’t trying hard enough.” – WinnerTweet

They say it takes doing something 10,000 times before you can gain true mastery of it.

If that logic is true, 922 days after joining Twitter, I can begin to say I am mastering Twitter. This blog post will be sent out as my 10,000th tweet.

To mark this milestone, I decided to take account for what has been shared and sent out over the past couple years and 10,000 tweets. As I looked over all the details I uncovered, here are some stats that I found interesting (to run these stats yourself, check out TweetStats.com and CrowdBooster.com)

Here is what the break down of how far each and every one of my tweets went. Some were retweeted by people with a lot of followers and there for reach a ton of folks. Others were retweeted a bunch of times.

Total reach of each tweet

Even through I joined Twitter in May of 2009, I really didn’t get into it until moving to New York in 2010. Here you can see how many times I tweeted each month over the past couple years. (Average 219/month)

Number of Tweets per month

Another interesting stat that I thought was really interesting was what time of day I tend to tweet. As you can see here, unless I am sleeping, there is a chance that I am sharing something about what is going on in my world. And, this may or may not reveal how little sleep I actually need.  (average tweets/day = 11.6)

Tweets by time of day

Then of course the question of, what the heck am I actually tweeting that much about? Here is a word cloud of some of the top words and hashtags that I’ve sent out over the past 10,000 tweets.

Top words in tweets

There is a very true saying that “what you measure is what you manage.” And, as I look back over this set if data and some of these other points that TweetStats.com and CrowdBooster.com revealed, it begs the question: “What, if anything, should I be doing differently in next 10,000 tweets?”

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On one of my favorite trips so far this year, I headed down under to Sydney and had the incredibly unique experience to speak at the Sydney Opera House as a part of XMediaLab Global Ideas conference. It was a wonderful experience and some of the most fun I’ve ever had giving a speech. Afterwards, I sat down with author Brad Howarth to talk creativity, success, and Gowalla.

I cover a lot of different ways that Gowalla has worked with brands and where we see the location based world going. Would love to hear your thoughts our conversation.

Part One (8:04)

Part Two (5:22)

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When Annie and I landed at LaGuardia this morning, we must have pulled the winning lottery ticket and actually had our luggage come out within 3 minutes of arriving at the baggage claim. Our good fortune continued when we hopped in the back of the next taxi queued up and asked our driver to take us home.

When he found out that we’d just come back from a weekend in Texas seeing my family, he asked what we thought about Rick Perry running for President. We talked a little further as he zipped in and out of traffic on the FDR and found out that his son is a Spine Surgeon having finished up at Cornell Medical School and his daughter is a banker in Midtown having completed her degree at NYU Stern.

Our cabbie was 62 years old and moved to New Jersey 45 years ago after leaving Hungary as a young man. He waited in Italy for over 2 years to get his visa approved before arriving in New York and starting a new life in America. He met and married his wife of 35+ years and worked 7 days a week to put food on the table for his young family. He started driving cabs on the weekends to make some extra money and then realized he could own his own business. He took all the money they had in the entire world and took out a loan to buy an NYC Taxi Medallion. When he bought the Medallion, it cost him $27,000. He eventually bought two more and had a small taxi company of his own. This past December, he decided that he wanted to sell his business and only drive a couple days a week for a friend. He sold each of his Medallions for $910,000 and is now sitting on $2,700,000 deciding what he wants to do next.

He said something that really stuck with me: “Back then, everyone knew that if you work really hard to become really good at what you did, you could make a life for you and your family. You might not have everything, but with enough hard work, you could be happy. And I guess you could say that worked out for me.”

That is the kind of country I want to live in. That is the kind of truth I want to share when I’m in my 60s.

That is the reason I love talking to NYC Cabbies.Tweet

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It’s what the chicken does that makes us ponder his motivation. We see noble young men helping old ladies do this in the movies. Crossing the street and getting to the other side is a normal part of an urban existence and also has some amazing parallels to the risks and rewards of the entrepreneur.

Now, I should probably point out that these observations are made with the assumption that you don’t look at the Walk/Don’t Walk sign. I only bring this up because, like in an industry or competitive endeavor, if there is a clear cut sign broadcasting what your next move should be, you’re already too late and everyone else is going to do the exact same thing as you.

The things I pay attention to when crossing the street and in assessing risks in business:

The Distance: How big is this street we’re endeavoring to cross? Is it a one way? Are there multiple lanes? Is there a median in the middle that can be used as safe harbor halfway across? Knowing how far you’re going to have to make it once you take that first step is a huge factor in taking the risk.

The Collision: How fast are the cars approaching? What is the average speed of the traffic flying by? How quickly will they make it to where you are intending to walk? What kind of vehicle is it? You have to know what kind of progress you need to make across the street before you take that first step.

The People: Are you making this gamble alone or are you taking people with you? If you have others that are going with you, do they know the speed at which you need to make it across and can they keep up?  Is there someone else lining up to dart across when the moment is right? Are they going to make their move first? Taking stock of who else is impacted by your next move is essential. You have to have total buy in from those with you and total awareness of others that might get in your way.

The Motivation:  How badly do you need to get to the other side? Is it a now or never kind of proposition? Are you going to miss out on something amazing if you don’t? Or can you wait a little bit and have the same results without as much risk? The timing of your first move is one of the most important decisions you can make. And, sometimes not beginning and missing the opportunity all together is riskier than stepping out knowing you have to move quickly.

Some of the things to do both as a competitive street crosser and as an entrepreneur:

Step to the front of the crowd: Don’t ever stand on the curb, take a couple steps out into the street and get a better look at what the factors are. Then, if you see the timing is right, go for it.

Know yourself: Knowing how quickly you can get from standing still to full speed is something only you can judge. Knowing your strengths and your limitations is essential for taking risks with confidence.

Commit to the decision: The worse thing you could possibly do is take a few steps out and decide you need to go back. By the time you slow down, turn around, and endeavor to make it back to the curb, you’ll have put yourself and anyone around you in more danger than if you’d committed and push forward without looking back.Tweet

My Dad has a lot sayings. A couple of gems are, “Gotta make list,” “Winning isn’t everything but losing sure stinks,” & “Gotta have a system.” As a former Barista, I am still amazed at the systems Starbucks uses to pander to the every whim of the fickle American consumer.

One of the first things you learn in Barista training, shortly after the brainwashing and Howard Schultz worship service, is how to call out drink orders. Since everyone has to earn their spot on the bar, the first position you learn is order taking. Once you take the order, you call it out to the person on the bar. The person on the bar, in between frothing soy milk and squirting raspberry into a tween’s cream based mocha frappuccino, has to scribble down on the side of a cup the order. The order takers job is to translate what the customer says into Barista speak and the official system of drink ordering to make it easy for the guy on the bar to scribble down.

So, when a soccer mom on her cell phone says, “Um, yeah, can I have a latte, a medium? Oh and make it with skim milk and put some hazelnut in it. And two Splenda. And also, make it decaf.”

The order takers translation, going in the order of the boxes on the side of the cup is: “Grande decaf nonfat hazelnut 2 Splenda latte.”

So, if you want to order like a pro, figure out your drink based on the boxes on the side of a cup.

Or, if you want to enjoy coffee the way it’s meant to be consumed, order the way I do: “Viente Bold. Black.”Tweet

I flew with Virgin Atlantic for the first time this past week on my trip to London.  It was a great experience and I enjoyed it more than most cross Atlantic flights. And then, I checked my inbox this morning to see an email from them entitled, “Was it as good for you as it was for us?” and I loved the whole experience even more!

As I was on the flight, I was thinking about Richard Branson and how he was the genius behind the experience I was having.  I’ve had a pretty well documented man-crush on Branson and always look forward to choosing to support the companies associated with his Virgin brand. He is the kind of businessman that I aspire to be: irreverent to the establishment, intentional about the end users being the focus, and having more fun than most think prudent.

And to answer the question asked by the email, “Yes, my first time was everything I hoped it would be.”Tweet