You may have noticed that I gave my blog a face lift this week. I’ve been having some fun working on a redesign of my site for the last few nights and I’ve been rebuilding the live site as I go. The redesign is something that I’ve wanted to do for ages now, and it’s finally getting done. I spent a lot of time this past year with my nose in design books and learning how to code better while building sites for others. Now that I’ve finally gotten around to it, I’m really enjoying the process of designing for myself a bit. I’m only a few days in but I thought it would be fun to share a sneak peek of what I’ve been working on. I’m using a fantastic baseline grid by Teehan+Lax for the design, which is free to download. The main site is going to look a lot like the blog does now – minimal, grid-based and oh-so Helvetica Neue.
All posts in Journal
21 PostsMy 3 Themes for 2011
Every year Chris Brogan does a “My 3 words” post to bring in the new year. The idea behind coming up with the three words is that they’ll be guiding pillars for what you’ll focus on in the coming year. Instead of resolutions, you focus on your own core themes as a lighthouse for your actions and efforts. I read Chris’ post this morning and my 3 themes popped into my head almost immediately, so I thought sharing them here was a good way to kickstart the year. Here are my 3 themes for 2011…
Presence, Focus and Personality.
Nominated For San Diego “New Media” Blogger Of The Year

I’m excited and honored to have been included in InfluenceSD’s nominees for “Blogger Of The Year” for 2009. InfluenceSD is a San Diego-based awards event created to unite champions in new media. The event celebrates success in social media and the people behind the campaigns and content. The fact that I’ve been recognized in this category by my peers and readers is truly humbling. A heart-felt thank you goes out to everyone out there who reads my stuff and leaves comments on this little blog. You guys make writing a joy for me.
The award winners are decided by your votes, so if you read this blog regularly, I’d really appreciate it if you could help me stay in the running. Voting closes on March 24th. You can register and vote here. :)
Again, thanks to all of you out there who make the conversations we have on this blog what they are. You’re the reason I write.
Connecting and Making An Impact
This morning I got a pleasant surprise. The mail man dropped off a hardcover copy of Seth Godin‘s new book Linchpin sent from a new friend. Totally made my day. Luke, thanks for reminding me again why I love to write this blog, and why helping others and giving generously are the best ways to connect with others.


Three Themes For 2010
I’ve decided to ditch the idea of new years resolutions this year and focus instead on three key themes. Here they are:
Limiting Myself To The Essential
I read Leo Babauta’s book The Power of Less late last year and it had a surprisingly profound affect on me. I didn’t have any major “ah-ha!” moments while getting through the book. It’s all pretty intuitive stuff. What did happen was that in the weeks after I read the book I started noticing some of my…let’s say, “sub optimal” habits repeat themselves while I was doing the hum-drum, day-to-day stuff that I normally don’t think much about – little things like checking my email first thing in the morning or before I sit down to work. I realized that the little stuff can have a big impact on my work flow and that I spend more time than I should on some activities that break my momentum, distract me when I’m focusing, drain my energy and don’t help move my important projects forward. In 2010 I want to work on blocking out clutter and distractions, and focusing on just the activities and habits that help me achieve my goals, improve my relationships and keep me on track. Optimization is what 2010 is going to be about. Wish me luck with this one. ;-)
Deep practice
There are a number of things I’ve always wanted to be really good at that I’m “just OK” at right now because I haven’t made achieving expertise in those areas a priority (yet). There are a few core skills that I want to actively develop in 2010. In a few cases it may take over 10,000 hours of effort to get me to the level of proficiency that I’ve always wanted, which is why I never really committed myself in the first place. I’m shifting my approach and putting some long term learning goals on the high priority list. The marathon towards expertise starts now.
Shipping
I’ve always had an insatiable desire to learn. The problem is that my free time is limited these days, and my curiosity isn’t, so I spend more time than I should Googling, reading blogs, taking on new projects that get half done, or buying books that don’t get finished. Doing 80% of 10 things isn’t progress. It just means that nothing got 100% done. Time to put more time into fewer projects and focus on the essential activities that help me wrap up projects and ship content. And there you go…we’ve gone full circle.
What are your themes for 2010?
Best of 2009
2009 was a great year for me and this blog. I had a ton of fun writing, I learned a lot and I got the opportunity to meet and work with a whole host of really smart, engaging people who opened my eyes and inspired me. In this post I’d like to take a moment to reflect on 2009, share some links and thank the people who really made an impact on me this year. Here’s my best of 2009:
My Top 10 Posts of 2009:
#1. Did Mark Zuckerberg’s Inspiration for Facebook Come Before Harvard? – A special thank you to Richard MacManus for giving me the opportunity to guest post on ReadWriteWeb earlier this year. The Facebook back story has become a growing obsession of mine since the release of Ben Mezrich’s book Accidental Billionaires: The Founding Of Facebook A Tale of Sex, Money, Genius and Betrayal. I did a considerable amount of journalistic research before the release of Ben’s book digging at where the idea for Facebook originated that lead to the article that went up on ReadWriteWeb. Fortunately, the syndication of the article onto the NYTimes (that my Mom was particularly proud of ;-)) surfaced a whole network of people who were around Mark Zuckerberg at the very beginning, before Harvard. There’s still some non-trivial elements of the Facebook story that run the risk of not make it into the history books, so my research is on-going. Stay tuned for some exciting stuff in 2010 on that front.
#2 Focusing On Value: How I’m Changing How I Use Twitter : By far the most popular article on this blog this year by measure of Tweets and comments. Thanks to everyone who contributed to the discussion and a special shout out to Nate Ritter, who started the conversation that led to the post.
#3 100+ Killer WordPress Resources: Even though I wrote this in late 2008, it was still the most heavily traffic’d post on my blog in 2009. Chalk that up to some good SEO that get’s me in the top 3 positions for the term “WordPress Resources” on Google.
#4 The Best Techniques For Building Your Tribe On Twitter The Right Way: A lot has changed with Twitter since I wrote this article, but much of it is still useful. I still use most of these tools and methods regularly.
#5 Emergence: What Developers and Entrepreneurs Can Learn From The Evolution Of The Retweet: What matters is not what your software can do, but how people use it. Culture on the web is constantly shifting. Entrepreneurs should watch changes in usage patterns to maximize value for users.
#6 How To Say Thank You On The Social Web: There’s an ingrained culture of reciprocity out there on the web that has it’s own currency. This post offers you some tips on the unwritten rules for participating.
#7 Status Culture – Public vs Private and Why It Matters – Discusses the difference between how we use different platforms to share our content, and how those differences shape online culture, the way we behave, and the evolution of systems and who plays.
#8 The Cookie Jar Principle – a short post with a useful metaphor on how we should approach relationships. I was happy this caught on and got handed around.
#9 Built It, Then Make Them Experts – Principals and best practices we can take from the video gaming industry that startups and software developers can use to accelerate adoption and customer happiness.
#10 How To Use Google Trends Like A Pro – A few great tips on how to take your Googling to the next level.
Giving Thanks – People Who Made A Big Difference To My Life in 2009:
This isn’t an exhaustive list by any means, but here are a few people who deserve a tip of the hat.
Alex Iskold and Fraser Kelton – I met Alex and Fraser when I sent their startup AdaptiveBlue a harmless feedback email back in 2007. That single email has (arguably) had a greater impact on my life than any single piece of web writing I’ve done to date. It started a string of online conversations that has turned into two friendships. Both Alex and Fraser have individually gone out of their way to help me out on several occasions when I needed it and I owe them each a debt of gratitude for coming through for me in the clutch. I wish both of you (together and individually) great success in 2010.
Nate Ritter – I met Nate at a Tweetup at the beginning of the year in San Diego after reading about him in Wired the year before. He’s genuine, brilliant and he’s become a great friend. He is also the best person to have in the room when someone says “Anyone up for Guitar Hero?”.
Mark Lovett – At the beginning of this year, Mark and I met for lunch. He told me he was starting a blog. I had no idea how committed he was or how much he would inspire me. This year I’ve enjoyed joining others in having important discussions on his site GlobalPatriot and watched Mark rapidly grow his online presence, run ultra-successful fundraisers and meetups. He’s a person to watch in 2010.
Angie Swartz – In between running her new company SquareMartinimedia, her blog SixFigureMomsClub and speaking at events around the country, she was kind enough to invite me as a guest a few times on to her radio show TwitterTalk radio. I had a blast. Special thanks to Angie for great times at the meetups that I attended this year. She always goes out of her way to say hello and strike up great conversation.
Clay Hebert – Clay is the founder of Tribes Win and co-founder of Fear.less online magazine. He’s great to chat and share ideas with. He writes a great blog and has a unique way of looking at the world that I totally appreciate. I expect to see a lot more from him in 2010.
Ryan Graves – Ryan’s become somewhat of a partner in crime on the web. His stamina for writing and producing content consistently impresses me. He’s always up to something. We started out blogging at almost exactly the same time in 2007 and I’m on his blog a lot – his stuff is full of energy and he writes almost daily.
Vada Dean & Matthew Clower – Expect these two gentlemen to make waves in 2010. It’s been great getting to know you both. Matthew, thank you for making important connections happen at the precise moment I needed them. Vada, thank you for the many insights you consistently add here on this blog.
Alex Rainert – Alex writes a great blog called EveryDayUX.com that I frequent. Damn good stuff. Recommended reading for any design junky.
Christian Messer – I’ve been aware of Christian on Twitter since 2007. From the very beginning I singled him out because he was posting things that I found useful. I learned more from his links in terms of design than almost any other person on Twitter. Check him out @whiplashdesign.
That’s it from me for now. Many thanks to all the people online who helped me learn this year and who’ve taken the time to leave thoughtful comments on this blog and connect over the web. I’ve reached out to most of you individually to express my gratitude, but I haven’t gotten to you all yet, but don’t worry, I’ll get to you soon enough. That’s something I’m going to do much more of in 2010. Happy new year, everyone.
Absolut Me
A Wordle of your delicious tags can be surprisingly revealing about what makes you tick…

The Last Time I Saw Dan Zaccagnino He Was Just Some 15 Year Old Who Wouldn’t Put His Guitar Down…
That was over a decade ago. I was one of 7 senior proctors who lived in Memorial House at Choate in 97-98′. Dan was a freshman who we were lucky enough to have in the house. I haven’t seen him since I graduated that year. This morning I caught a clip of him on the Colbert Report talking about the company he co-founded, Indabamusic. You might have heard of it. They’ve built a global community of over 125,000 musicians in 170+ countries. Incredible. So that’s what you’ve been up to, Dan. A very humble hat tip to you…
| The Colbert Report | Mon – Thurs 11:30pm / 10:30c | |||
| Dan Zaccagnino | ||||
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George Needs A Job
Everyone, meet George. Every morning at 7:45am for the last 6 weeks I’ve passed him on my way to work in Carlsbad, CA. Every day he’s up before me, standing proudly in business attire with his bright yellow sign that says in huge bold letters “I NEED A JOB”. Today I stopped and interviewed him on camera in hopes that I could share his story with all of you, because it’s quite inspiring (see the video below).
I’ll let George tell you about what his 6 weeks holding his sign has been like in the video, but I would like to share some additional thoughts about him. Off camera I had a chance to chat with George and ask him very directly about why he believed standing at the side of a main thoroughfare in Carlsbad was a good idea and what the experience had been like for him. I genuinely wanted to hear what he had to say – 6 weeks is a long time to stand in the hot sun holding a sign like this one. His answer was incredibly humble, optimistic and honest. He said “I am one of the huge percent of people who’ve been laid off in California, and all of them are looking for work. This turns the tables in my favor. Every morning I have people see me who can help. People have come together to help me pay my rent, and this week I’ve had more interviews than I’ve had in 3 years, but it’s taken 6 weeks of standing here to get to this point. It’s hard because it hurts your pride standing on the side of a road with a sign like this, but the experience has been positive and I’m optimistic.
7 Things You Probably Didn’t Know About Me
A few days ago I was called out on Twitter by a new friend of mine, Ryan, to write a “7 Things You Probably Didn’t Know About Me” post. I’ve never been one to turn down a challenge. In the name of holiday fun, here goes:
1. I was kind of musical in a past life. I grew up on 2 piano lessons a week from age 7, and graduated to playing the alto sax in a jazz quartet for a couple of years in high school. Eventually, I dropped the instruments and joined not one, but two a capella groups – one in high school (The Maiyeros) and another right after that at Boston University (The Dear Abbeys). In college, we made a couple of records - one horrible, one not so horrible. Had a ball both times. I even got to sing the national anthem at a Celtics game once, which was pretty neat. Some of the best memories I have are of singing with others.
2. I once worked for a surf tour startup company in Australia. Before I graduated from University, I spent six months backpacking around New South Wales surfing and giving multimedia presentations to travelers from all around the world. I met the owners of the startup while on one of their weekend surf trips out of Sydney. One night over burgers we got talking about their business model, and how they needed a web site and someone to do PR for them. They asked me if I knew anyone who knew HTML and who could work PowerPoint. I was in the right place at the right time. It was the most exciting job I’ve ever had.
3. My father is a professional tennis player. True story. For about 12 years he coached the National Davis Cup Team for the Bahamas. He was in the top-200 in the world for a while when he played on the circuit and he’s even in the Bahamas Sports Hall of Fame. I love playing tennis but I…ahem…didn’t inherit any of my dad’s talent.
4. Water sports were more my thing. I swam and played waterpolo competitively throughout high school and as a graduate student at Georgetown in D.C. in the Mens Atlantic division. Waterpolo doesn’t really get you the kindof props that football or basketball get you, of course (insert reference to drowning horses here), but I loved it. Most of my life-long best friends are waterpoloers (if that’s even a word).
5. Some guys go fly fishing with their dads…we go spearfishing. I grew up in the Bahamas, what can I say? It kind of comes with the territory. August 1st is the official opening of lobster season down in the islands, and every year me, my dad and my brothers would get up near dawn, hose off our gear and head out to a reef somewhere to catch dinner. Seafood BBQ’s invariably followed.
6. I love concerts. There’s really no substitute for experiencing music live. My first concert ever was James Taylor when I was a senior in high school. My second concert was Elton John at The Boston Garden (back before it was the Fleet Center when they still had the old floor that Larry Bird played on). Just Elton and a piano for 3 solid hours and he was literally the most energetic performer I’ve ever seen (to this day). That was the best concert of my life, but not just because of the music. There was also the fact that I went with a cute girl I met in English class…
7. I never got over that girl. And (luckily) I never had to. We got married a few weeks ago. Just a small group of family and close friends joined us for a week off the grid in the Bahamas to celebrate. It was one of the most memorable weeks of my life, and it was fantastic to be surrounded by so many people who mean so much me. We still talk about that concert, over 10 years later.
So there’s my seven. If any of you would like to continue the chain, feel free to link back here in the comments. Get personal, and tell the rest of us what makes you unique.
Happy 2009, Everyone.
Shut Down, Unplug, Reboot
After a long (but much needed) break from everything Internet, I’m excited to be back at the keyboard. OK, maybe not everything Internet…despite my conscious effort to stay off the grid these past few weeks, I still maintained near-daily twittering thanks to my blackberry. If you’ve been following me on Twitter, you’ve watched me make some major life changes over the last three or four weeks, including a rockin’ upgrade to a new job. Needless to say, I’m honored (and lucky) to have been offered such a great opportunity and I’m completely stoked to have made the jump. Although I will miss working with close friends at KPMG, I’m really looking forward to settling in to my new diggs. The new position comes not only with a whole set of exciting new challenges and learning opportunities, but also with the chance to make some positive lifestyle changes as well (a theme I will reflect on in a second).
The week I took off during the transition was particularly rewarding. Aside from getting some much deserved rest, it got me away from some of my (sub optimal) habits, and gave me a chance to regroup, reset and get back on track. I was reminded that a good forced period of being unplugged is necessary and healthy because it gets you out of your regular patterns and forces you to take a good look at what’s working for you and what’s not, and gives you a fresh perspective to help you re-evaluate your happiness as well as your goals and approaches to achieving them. And in the spirit of making changes that positively affect my life and happiness, the following are a few zen-ish themes I’ve been giving a lot of thought to in my time off (feel free to comment and contribute your own):
You Only Have So Much Energy In Your Tank
Managing and monitoring your own energy levels well is a core-skill that everyone should spend time mastering. Our energy tanks are not infinite (mine definitely isn’t) and energy levels are always in flux – we’re always in motion, either filling up our tank or burning through it. Keeping your tank full is largely about how you allocate attention and choose activities.
Different Activities Affect Each Of Us Differently
You don’t have to sit on your butt to recharge. Finding and engaging in activities that energize you and filling those energy reserves (whether it’s reading about something you’re interested in, pushing yourself to get a runners high, learning a new skill or engaging yourself creatively) is key to being happy(er) and effective when you have to do something that depletes your tank. The trick is learning which activities energize you. (Reading cool photoshop how-tos and books about the web, for example, is something odd that really gets my brain going and brings me to life…weird, maybe, but it’s an energy ++ when I’m feeling tired. On the other end of the spectrum, watching mindless TV actually drains me (think The Hills or The Real World, rather than the discovery channel). Everyone’s got their own energy boosters. What’s yours?)
Set Time Aside For Activities That Energize You
Obvious. Use energy boosters to manage your energy levels when you’re burn rate is highest. If you’ve reached the bottom of your tank, your productivity, efficiency and creativity will likely be equally low and it might be time to take a break and do something else. If you’re approaching empty, head it off by quitting a little early before you burn out. The most effective people strike a perfect balance so that they maximize the time that they are efficient, productive and energetic.
Manage Your Fill/Burn Rate
The same activity will never give you (or take) the same amount of energy every time you do it. Your fill and burn rates change depending on how much energy you have at any given time, especially when you’re running low. As you approach empty, your burn rate for activities that drain you goes up. Said another way, activities that drain you will drain you more quickly when you’re burnt out. We’ve all experienced this. Know when you’re approching burn out levels and focus on energy rich activites to keep you in a productive energy zone.
Make Time To Connect With Non-Work Friends During The Week
People often don’t realize how energy-rich the activity of connecting with friends can be. Feeling isolated can up your burn rate no matter where your energy and activity level is, and even limit your ability to recharge. It often becomes apparent after you’ve gone past the point of no return and loneliness sets in. Some people are natural loners, but even they can experience depression if a feeling of not being connected takes hold. Connecting periodically is a must for everyone.
Plan For Randomness
Doing the same activities over and over, no matter how energy rich they are, is futile. Repetitive experiences are always subject to diminishing returns. Keep things new to max out your fill rate.
Taking The Red Pill: Thoughts On A Week of Professional Hacking Training
This week I really got to see just how deep the rabbit hole goes. Five long days sitting in a lab in Orlando with 20 professional hackers has opened my eyes to just how insecure the systems and connections we trust every day really are. The experience was nothing short of mind-bending. Passwords were pulled from the air at the touch of a button, CNN’s home page was defaced in front of my eyes, and tens of thousands of dollars could have easily gone “missing” from e-commerce websites at checkout – and these guys were loving every minute of it. The bigger and more complex the hack, the greater the bragging rights, and the capture-the-flag competitions in our little “closed loop” lab got pretty intense. I say this with a smile – I’m just as paranoid now as I am stricken with awe and admiration of people who have mastered this particular brand of technical hocus pocus.
Before last week, I was pretty green when it comes to black hat hacking – I’m grateful for having the opportunity to learn so much and meet the great group of guys that took part in the pilot training program. It’s funny, I hear horror stories from my clients all the time, but I’ve never really seen the true extent of what is possible by looking over the shoulder of someone waving the magic wand. This week was awesome because I actually got to get my hands dirty and try things in a closed network that I couldn’t even attempt in my own time without breaking the law. For that reason alone, this week was invaluable – it gave us all a chance to trade our white hats for black ones, if only for a few afternoons, and get to “know our enemy” on a much more intimate level. For those of you wondering, here’s a high level overview of what 50 hours of “Ethical Hacking” training covers:
- Abusing DNS
- Abusing SNMP
- Passive intelligence gathering (techniques for gathering info remotely, what types of info bad guys go after and how multi-pronged attacks are planned)
- Hacking TCP-IP
- Stealthy Network Recon Techniques
- Breaking Windows and Unix Passwords (terrifyingly easy, btw)
- Learning exploitation (using zero days, reverse engineering and gathering info on known exploits from the net)
- Exploiting Windows OS, Apps and Linux (ever seen someone hack into a machine by writing and executing code directly into windows media player? Jaw dropping stuff)
- Deep Target Penetration (how to go after info on the CEO’s laptop from outside the firewall, for example)
- Offensive Sniffing (you’d be shocked at how many passwords you can get with free tools just sitting in a hotel lobby)
- Covert Channels (think a firewall can stop everything? Wrong.)
- Covering Your Tracks (manipulating logs, using stenography to hide information in plain sight, matching traffic types and patterns, exploiting how intrusion detection systems work)
- Wireless insecurity (this module made me never want to connect to the net in public places again, but also taught me how to get free wireless at just about any Starbucks or public hotspot – very cool)
- Attacking Routers
- Hacking Web Apps (defacing web pages, e-shoplifting and SQL injection to exploit interfaces with web databases etc. – coolest thing was that we saw the instructor change the price and quantity of an expensive set of items in his shopping cart on a real e-commerce website using just a free firefox extension.)
All of this is pretty scary stuff, really.
Overall, my memories of this week will be bitter sweet. The good is that the experiences I had will significantly change the way I approach my work from now on, and will definitely improve the way I engage my clients. The bad is that….I can’t go back to not knowing what’s out there. I worry that the geek in me won’t get the same kind of “job-well-done” rush that I used to get when I’d finish a security assessment or an IT audit. A week ago, I thought we were really designing good full-body armor, but now it feels like I’m handing my clients some cheap fencing gear, patting them on the back and reassuring them that they should feel confident about going into battle. My heart sinks a little, you know? I know now that we just don’t have the budgets, the equipment or permission to be able to do what’s truly necessary to protect a company’s systems from the really dangerous attackers. That all may change as our industry evolves, but for now, the cold hard truth is that even an IT security expert with an unlimited budget, no restrictions and infinite time couldn’t get your risk to zero. It’s a scary world out there and my eyes are wide open. The only question now is, if Google can be your worst enemy, and novice hackers can download powerful tools for free, and attack an organization from virtual, anonymous “clouds” from anywhere in the world without much fear of getting caught, how do you really circle the wagons effectively? Or more importantly, how do you stop paranoia getting the best of you? ;-)
Feasting With A Foodie
We all eat, but some of us enjoy it more than others. Sometimes a lot more. Eating with someone who truly appreciates not only food, but everything that goes into the experience of eating, can be a total joy.
Last night I went out to dinner with a “foodie” friend of mine, Kevin, a staff writer for LAist.com whose up and coming blog 50meals.com is a must read for food-lovers living in, or around, Los Angeles. I admit that I go out to eat sushi a lot when I’m on projects in L.A., but I had never been to Little Tokyo, so when Kevin, a seasoned pro, excitedly suggested Sushi Gen I was in. From beginning to end, the night was full of lively conversation about food, life and all the small things that make the whole experience of meals so great.
What I love about Kevin is that his energy and appreciation of all the meal’s details is infectious. He doesn’t just talk about food being “good” – Textures, aromas, colors and flavors all get an uncommon level of attention in the across-the-table banter. And, of course, sometimes no words are necessary – you can see it written all over his face when he takes a bite of something he’s really satisfied with. He totally lights up. (Kevin – how good was that melt-in-your mouth toro, or that black cod!?). All in all, the night reminded me of just how important it is to be around people who appreciate the small, simple things that make an experience joyful. Thanks to Kevin for such a memorable night in L.A.!



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