In October, we learned that Annie Pontrelli was diagnosed with brain cancer. Because of what kind it was, she knew before any of us would even consider it that she didn't have long and that she wanted to make it count. She sprung into action as the planner, the uniter, and the encourager that she has been for her entire life. She wrote to Annie incredible emails filled with wisdom and one of the lines that jumped out and stayed with me was this:

"Sharpen your sense of wonder and connection."

She truly lived a life with a full heart and curious mind. And not just that, but she brought people along with her on that journey and invited others to explore with her. Whether it was the latest exhibit at the Met or returning to deep Brooklyn to show others the best Italian Bakery, everyone was invited. She never let her work get in the way of her life. She surrounded her daughter with friends and asked them to be teachers. Adriana, at the age of nine, has had so many voices sharing their story and has a network of people invested in her and caring about her unlike anyone else.

Annie was a part of our NYC story from the very beginning. She was a voice of encouragement when we friend to move here and failed. She was a cheerleader when we finally did arrive and was one of the first to hike up the 66 steps to our Village walk up to survey our precious 300 sq feet that we called home. She never tired of asking about our jobs or our travels. Her curiosity and generosity made for an incredible combination. As she was asking questions, she was ever so subtly sharing advice. It never felt like a lecture or anything other than a loving conversation. She was so smart that it elevated every single interaction and everyone around her to be their very best.

We know Brooklyn, all parts, better because of Annie. We know NYC, all parts, better because of Annie. We know ourselves, all parts, better because of Annie. We know what it looks like to live life, all parts, with a sharpened sense of wonder and connection because of Annie.

Dr. Abraham Maslow put self-actualization at the top of his hierarchy of needs. Plato encouraged Socrates to "Know Thyself." In NYC, when crossing the street, it is should be "Know Thy Stride," that just might be the difference between getting to the other side of the street and being a NYC Taxi and Limousine Commission statistic.

I am tall. I'm even taller on days when I wear my cowboy boots (or said another way, everyday.) I live in NYC and therefore my expectation of the speed for walking would look like running to others. As a result, my stride is longer than most. This can be hazardous when I am walking with someone through the city that is more vertically challenged, especially if they're not used to the pace of the city that doesn't sleep.

Knowing my stride allows me to get across neighborhood streets and avenues quickly. Knowing my stride gives me confidence when stepping off the curb at 23rd Street and 6th Ave in the middle of pedestrian rush hour with the Walk/Don't Walk sign signaling that there is only 4 seconds left before aggressive cabbies stomp down on the gas and come flying through the crosswalk. Knowing my stride lets me take the risks that others with different strides might not.

The same can be said about life. Knowing your stride allows you to know how far you can stretch and how fast. It allows you to say yes to risks that you know you can outpace and say no with confidence to opportunities that you understand intuitively will end up with misaligned expectations and damage to everyone involved.

But, just like walking in NYC, you only learn the full extent of your stride by using it and pushing it to the limit.

My bike only has one speed. Whether going down hill or making a climb, I don't have another gear to shift into. Me and my bike are a lot alike. I mentioned in my last post that I ride pretty aggressively in NYC. I wear a helmet and my training as a professional bus driver in college comes in handy as I zip through the winding streets of the West Village and the yellow cab dominated streets of Midtown. But now matter the neighborhood or terrain, I only have one speed.

Only having one speed is an incredible way to feel ever turn and know exactly what it is going to take to make it through an intersection or climb up a hill. Only having one speed means selling out to the effort you know it is going to require to grind through the backside of Harlem Hill in Central Park. With just one speed, there is no confusion about how to approach any kind of terrain, you just approach it like you do everything else and don't stop pedaling until you're on to the next one.

Yes, having one speed does mean your uphills feel higher and your downhills feel lower, but, knowing what you have and leaning into it makes the ride that much more personal.

I am a competitive person. I abhor the idea of playing a game and not keeping score. If there is a way to win, I will find it. If there is even a way to CLAIM a win, I will attempt to. Which is why riding my bike the past few weekends has proven to be an interesting change of pace. When I ride my bike in NYC, I usually head over to the West Side Highway bike path and ride North along the Hudson River. The path there is just wide enough to pass slower bikers or joggers without scooting over into oncoming traffic. And when I ride, I tend to pass a lot of folks. Even more now that the CitiBikes are out and people who haven't ridden in NYC are doing so for the first time in a long time.

And sometimes, I get passed. Usually by guys in spandex with bikes that cost more than my first car. At first, being passed bothered me. They were beating me was my default thought process. They were going faster and they were winning. But then I considered, did the people that I passed think the same thing? Was me zooming past them in the realm of consideration that I was winning? Of course not. And neither were the guys zooming past me thinking that they were beating me. It wasn't a race. We were all out there for different reasons with different levels of equipment and training and health. Even though we were all doing the same activity, an activity that by its very nature showcases speed, strength, and distance, we were not riding with the same end game in mind.

I am in San Francisco this morning and I've been thinking a lot about the technology scene and industry and how it too isn't a race.  There are countless ways that you could think that someone was passing you or that you were falling behind, but that isn't a fair race to ride because we are all coming into it with different equipment, skills, and teams than everyone else.  And, if we are all smart, we are all riding for a different end game than everyone else. An end game that is ours and ours alone. I'm not talking about an exit or the cover of FastCompany or some other moment in time goal, those can't be the reason we are all riding as hard as we are. The reasons have to be bigger, otherwise you won't enjoy the downhill that comes after you powered through the grind to get to your momentary peak.

When it is all said and done, most of life isn't a race against anyone else but ourselves. Everything that we are building has to be worth it for our own definition of a win, not for anyone else's.

I have attended three local political events in the past ten days. That is three more than I attended all of last year. But, as the flurry of activity died down on the national campaign cycles, where big money and SuperPACs actually were the ones with impact, the momentum has started picking up for some big local elections this fall.  As I listened to candidates and representatives from campaigns, one thing became clear: an understanding that technology is important is no longer enough, first hand knowledge and personal examples of using technology for the benefit of their constituents is the new standard. This truth was on display at the Start Up City Conference hosted by Manhattan Borough President, Scott Stringer. Starting the day with a Keynote by the "Godfather of the NYC Start-Up Scene," Fred Wilson, the day brought a well rounded look into the ways that the city of New York is thinking about the growing digital industry as well as shed light on how far the Big Apple is behind other smaller cities in terms of connectivity and infrastructure. Some of the harshest words toward that end came from Andrew Rasiej as he called out Chattanooga, TN for having internet "20 times faster than New York." As the Chairman of the 32,000 member New York TechMeetUp, Rasiej and their community have laid out their top seven policy initiatives.

The conference wrapped up with a panel of almost all of the candidates for New York Mayor and was moderated by Buzzfeed's Ben Smith. Mr. Smith started off the panel with the only question that seemed to really matter to the technorati in the audience, "What kind of phone do you use personally and what is your favorite app?" 100% of the candidates answered that they used a Blackberry personally and only half of them could name their favorite app. The other half resembled Sarah Palin when Katie Couric asked he about her reading habits: "Oh yes, apps, I use a lot of them. I couldn't name one specifically that I like because I just seem to like them all." The candidates that could name an app were split between MLB and Pandora as their favorite app.  And while you can't judge a person by their apps, but is was a huge miss to not show some competence in using the technology that is free and readily available to make their own lives better as their example of a favorite app. And made an even bigger miss when they could have given a shout out to some of the fantastic companies making that technology right here in NYC. These response to the question drew me back to another event that I attended earlier in the week.

"We need leaders that know and that use tech" was the opening statement from Twitter and Square's Jack Dorsey as he endorsed and introduced Reshma Saujani for New York's Public Advocate at her rally last week. The packed room erupted in cheers as when taking the stage Ms. Saujani told the crowd that "we don't need another politician, we need a change agent." She went on to lay out her personal experience in the world of digital and technology and pointed to her experiences founding girls who code. Running an incredible digital savvy campaign, Ms. Saujani is the first of what I hope to be many more technology entrepreneurs who make the cross over to involvement in public service. As the digital community digs deeper and brings more value to every area of our lives, we need leaders in every level of government who understand, and are not afraid, of technology.

The final event that I attended was for Michelle Wu, a candidate for the City Council in Boston. In the back of a fantastic restaurant on the Upper West Side, Jacob's Pickles, current and former residents of Boston gathered to hear an update on their city given its recent tragedy, but also to hear Ms. Wu's vision for the future. As a recent graduate of Harvard's Law School and an alumnus of Elizabeth Warren's successful bid for the US Senate, there were more than just loft ideas share, but comprehensive plans for action. "True change happens locally when people, when neighbors, come together for the good of their community."

I am fascinated by politics. Perhaps even more so as I recently went on a West Wing to Scandal to House of Cards political entertainment binge fest. But also because, much to the dismay or my Libertarian leanings, government is going to be a part of just about every meaningful initiative that I undertake going forward. Whether building companies, launching nonprofits, structuring my will and estate plan, or just saving for retirement, there are rules and regulations to be understood. And having the right people with a seat at the table for those conversations and future reforms is most definitely in all of our best interest.