Tools of the Connected Geek Trade

As we move up the food chain of life, our free-time becomes more and more precious. There are only so many hours in the day and my generation utilizes them to the fullest. I have been blessed and fortunate to be placed early on in my career in leadership positions while often having to continue my technical work.  This means keeping a foot in each role and staying current. The past few years I have honed my life work-flow to accomplish this. Here are my tools of choice:

From the time I carried my fathers forgotten Palm or Casio PDA, I have always had some sortof technology in my pocket. When the connected PDA and first smartphones began to hit the market I scrounged what little funds I had to acquire one. There is no other device that  is more of a  knowledge force multiplier. Being able to find old emails, read RSS feeds, and query my second brain AKA the Internet made my moments in line at the store or riding around town filled with information consumption. In the military I was given the blackberry to the left and it changed everything. I always had issues with organization and keeping appointments. No longer! Today I am glued to my HTC Evo 4G most of my waking moments to ensure I am responsive to my clients and friends. In addition it downloads all my news and information for O2G access.


One of my favorite activities is diving into technical manuals and white papers. Many of my clients and coworkers can attest to me awake at 1am reading through some material and having that “AHA!” moment and sending them a fix. In the early days of my life I carted a few hundred pounds of books around, but that isn’t needed anymore. Truth be told, books are no longer that necessary. Between Instapaper and eBooks I am set. The long form articles on my favorite websites mixed with the ability to search some command or term through a few hundred PDF’s make me a knowledge machine. I have gone through every eBook technology, but have finally settled on the iPad as my reading consumption device. The SoftBook reader I started with provided much better reading clarity, but at the expense of PDF rendering and multi-application usage. Part of being a young business geek is mobility and having a single purpose device just doesn’t work anymore.


My vehicles all have bluetooth for stereo or iPods for a very simple reason, podcasts. Ever since I start with Juice on my linux box years ago I was hooked. It started as a way for me to connect and listen to other like-minded geeks. When I was a teenager I did a local radio show focusing on technology every so often, but specifically I was the “Linux” guy. Before podcasts unless you happen to catch me on those rare Saturdays, there was little opportunity for you hear the latest news. Even then if you happen to catch the show I wasn’t able to dive into the gory details of Linux kernel or latest GTK releases. Podcasts changed all of that. Every night my devices download the latest and greatest Economist, tons of TWIT stuff, This American Life, NPR Planet Money, BBC Documentaries, Hardcore History, MIT CoursewarePhilosophy Talk, and countless others. While walking to the metro or sitting at work I almost always have some podcast going. They allow me to absorb information while multi-tasking and completing other tasks. Also due to the extensive selection I am able to broaden my horizons by moving outside the mainstream and hearing other perspectives. In the business world this has afforded me a ton of kudos. “That contract won’t hit there because the finance ministry is in utter-turmoil” makes you sound like a superstar.


It is embarrassing how much I use Google Reader. In fact thanks to their trending and analytics I can tell you I have read 2,240,432 items since 2006.  I have bounced on self hosting my RSS reader and using NetNewsWire, but always come home to Google. The API and integration with applications allows me to view and sync my feeds across all my devices. In a systems engineering perspective though Google Reader though is the tool, the requirement is information. For me to be beneficial to my customers I must always be aware of the latest and greatest. On top of general information, I add a multitude of political, religious, local, and hundreds others to my stream to compare. It is impossible to ingest news and data in a linear fashion. For example rather than “watching” television on a single station I am able to see every opposing view within seconds. Over the years I have also kept up with researchers and people I admire via RSS. The next time I see them I am able to know what their mind is focused on and make the best use of our engagement. “I loved your article on new network heuristics using more than just simple ICMP/SNMP, where do you think the technology will take vulnerability scanners?” Being able to showcase that you are aware of what the industry is doing, what they are doing, and that your time with them is important ensures you aren’t just talking about the weather.


I have no intention of starting an Operating System war, but I have to attribute my ability to stay connected to UNIX/Linux. With my Debian and OpenBSD home servers I am able to SSH, tunnel, VPN, manage, sync, and store my data securely. Even those items that I have moved into the cloud I still ensure I sync back to my home systems. Using a mixture of screen, bitlbee, tor, and links I am able to keep constant roaming communications with everyone. The prevalence of open-source gives me the ability to do this securely and from any device. Heck, even my Blackberry from work has a SSH Client. Numerous times I have been in situations where my ability to have constant and secure communications has saved us. “Oh noes! We can’t access this from here?!?” Then I step in with a UNIX platform and a comms link and fix it. Others argue that in fact its the ability to utilize remote services, but I’d argue that UNIX is the only intrinsically remote/secure way to do it.


Where were you when you found out Osama bin Laden was killed? I was sitting in bed with my iPad and twitter open. The pace at which information flows now is mind blowing. I believe this is why we see CNN and others just running shows around “trending topics” which is highly depressing. The edge has been lost and given to people willing to sort through the data. Between Reddit, Twitter, and Hacker News I am able to stay DAYS ahead of the mainstream and react before the masses have been made aware. You must apply some filters to the data as it is often streaming live to your device. For example when the riots began in Egypt and Iran there was a good bit of disinformation, but if you took it as a whole the picture made more sense. I can’t imagine relying on mainstream media to curate my information any more. The only reason I utilize news outlets like the Economist, BBC, or Al Jazeera is to dig deeper. Seeing pictures and video live from breaking news is great, but I go back to traditional media for the “what it all means” side. If you want to stay steps ahead of your peers these three sites will keep you there for tech, politics, and just about everything else.


At this point in life I cannot afford to hire an assistant and many close to me have made it clear they aren’t interested in pitching in :) Google Voice (tech hipster point – I was using it when it was Grand Central) has changed the way I think of mobile communications. No matter where my phones are I am able to get SMS, Voice Mail (transcribed!), and make calls with Google Talk. Everyone continues to see my single phone number and is no smarter to the fact I am not near a line. There are still a few rough edges, such as the feature-set and lack of strong applications for iOS or updated Android apps, but it doesn’t change the fact it is central to my daily life. On the fly recording, conference calls, and movement from one phone to the next keeps me in constant comms.


Last time I forgot an important date? NEVER…If it is on my calendar I am guaranteed to be there. My girlfriend is able to, at a moments notice, know if we are going to have time to go out or eat in. Friends are sent meeting invites to parties and meetings to make sure I am there on-time. In good humor they joke with me about my meticulous attention to sending meeting invites to the simple things, but I am sure deep down appreciate my timeliness. Do I need to send an invite to remind me you are coming to play basketball? YOU BETCHA! Between Google Calendar and Tasks I have a forward and reverse look at all important dates in my life. Before the advent of a central calendar I was tied to a single data point. Forgot your phone? Screwed. Forgot your day planner? Screwed. Forgot your girlfriend? Double in Trouble. Live alerts via javascript, SMS, and email ensure that I am not only on time, but usually early. The Air Force made damn sure I knew that on-time was late; 15 minutes early was on time.


I am going to let a secret out that my father taught me. It really ties into the last entry on Google Calendar, but expands beyond just reminders. When we work in business we often divorce the P&L, staffing profiles, and technology reports from the pure emotions of life. Many of my colleagues are very nervous about Facebook and other Social Networks. There is certainly some risk in being transparent to your staff and coworkers, but think of how much better a leader you are if you know the things that effect our lives outside of work. For example in the past when I was managing a highly mobile team I was able to see when my guys’ kid was having a birthday. Or see that his weekend was filled with an emergency due to some unexpected event and react. In a business sense none of that is suppose to matter, but imagine the look and relief in their voices when I called to tell them we could do without them for a few days to handle business at home. It was an amazing feeling to send some guy home for his birthday or anniversary even if he hadn’t told anyone. Sure I was cheating by using published data, but I did it to ensure my team was happy and getting the all to forgotten recharge time. Teams I no longer work with I still follow to see how their careers are blossoming, families growing, or their desire for another challenge working for me :)

This is a short sampling of what makes-up my process for staying savvy and connected. I am having such a hard time to decide where to cut off this list as there are so many more. Netflix, Skype, Amazon, Kayak, TripIT, etc. There are just a ton of things that make me incredibly connected and organized. The downside to all of this of course is I am LOST without an internet connection. Such are the things we give up to have a digital life.