The Power to Dream

Sometimes you underestimate the power of little things. Case in point, the power to dream. As people get more and more experience, imagination starts to take a back seat and you start thinking in terms of what might be possible.

It just struck me at a small gathering. We were planning an event and a group of us were talking about realistic approaches, what kind of strategies would work, what we need to do it. On paper, the obstacles are quite formidable. However, one person had the “vision” or the “dream” and somehow every time he said something there was so much conviction in his vision and hope in his eyes that nothing we could say would diminish it.

So we walked away with a little bit of that hope and started thinking of ways to do it anyway. It’s really amazing how we sometimes hold ourselves back for the stupidest reasons and draw conclusions when we get the greatest reality check for free: reality. Makes you wonder what the point of limiting yourself is when you can just deal with reality and keep adjusting your plans until reality eventually comes around.


Like all bloggers, every new year brings on a fresh bout of “I shall blog more” syndrome where we trick ourselves into thinking that with the new year we will some how magically be transformed into diligent bloggers that are eager to share our witty insights and soaring intellect with the world at large. We bow and scrape, write out our apologies for neglecting our loyal readers awaiting the next exciting installment with bated breath.

It all starts magnificently. We rediscover the joys of blogging again and may even get back into a regular schedule of posting. Then the well runs dry. We stray to twitter or facebook and look on as other bloggers crank out content. The rich bloggers hire other fresh bloggers while the rest fade away and before you know it it’s another year, saying “maybe this time it’ll be different”.

Founders at Work

Founders at Work certainly lives up to expectations. If you’re looking for inspiration on how people bootstrapped themselves in the tech sector to wild success here it is. Now, as a chronicle of the nascent IT sector at this point in history, there are a lot of people who were at the right place at the right time, think early 90s computer science majors. You can dismiss them as one hit wonders, trying to extend that last hit by becoming venture capitalists or dreamers now working at smaller web shops like the rest of us, looking at smaller payouts. However, you can’t deny the fact that they did it and succeeded.

There’s not much you can learn from one hit wonders. Just remember that if you ever get in a position where you find yourself out of your league with a wild streak of luck, you have nothing to lose but to run with it as hard as you can take it and cash out quick but not too quick. However this book is littered with gems. One story that stood out to me the most was the story of Max Levchin, the co-founder of PayPayl. He originally set out to offer encryption software for the palm pilot which evolved into payments (the most direct application of the technology). Paypal was more of a demo rather than the end goal. What stood out to me was the fact that as the service grew traction, he focused on fraud prevention more than anything else and even dedicated his full attention with the help of a brilliant intern to track down common patterns and flags to prevent it. The versatility to see the true deal breaker of a service and tackle it effectively, that’s not luck.

James Hong of HotorNot (since sold off) was another funny one. What started off as a lark soon grew into a business but what caught me was the approach he took, like stopping some random guy on the street and asking him, “dude, did you see that new site ‘hot or not’, you need to check it out” or hosting images off of Yahoo! geocities to scale and finally convincing a hosting company to sponsor their infrastructure in exchange for publicity. That’s true entrepreneurship.

All these people rose up to the challenge and didn’t give up. They came up with some weird and unique solutions. It’s a story of inspiration and character. It makes you want to jump out of bed and start a company.

Founders at Work

The End of the Internet Magic Mirror

I woke up today to read a really good email from Jason Calacanis. I was certainly one of the people who wrote some negative stuff about Jason only to be confronted with a nice man who is both a successful entrepreneur and a great speaker. It’s always an awkward moment. Luckily, after more than a decade using the internet and maybe the calming effects of age, I’m much less prone to internet asperges syndrome although I’m much more likely to blurt something out on twitter or have to check myself every now and then when sending a short email. The other day, Mike Arrington got spat on. While Mike isn’t exactly the most loved guy on the internet, many draw the line at getting spit on. While I agree that things are getting out of hand for people like Jason and Mike who are some of the most successful people who have bootstrapped themselves on the strength of blogging, they’ve also done their share of negative baiting, Arrington’s bashing of Twitter and particularly Blaine Cook comes to mind as well as Jason’s spats with David Winer. However, when the stakes escalate to personal violence then it’s time to splash water on our collective faces and try to wake up.

The Internet Magic Mirror

The crazy thing about the internet is the “fake anonymity” creates a magic mirror effect between the haves and have nots. In this case the “haves” can be anything from more money, more fame (especially the internet variety), or simply more expertise. Usually, the target of ire is someone with a very visible profile or following. Their actions are more or less public and their opinions shape discussions on the internet. It’s like we’re looking at them from behind a magic mirror. They see a mirror, we see them. The only difference is they may not see us but they can hear us like we hear them. If you peek at the comments section of any famous blogger intrepid enough to allow them, you see it is a veritable cesspool with some rare gems in between.

Why is the anonymity fake? Unless, you are a cracker or hacker versed in internet protocols you know very well that unless you hop a couple proxies and take steps to cover your tracks, that when you overstep the line, the police will come knocking at your door. Probably, given away by your internet service provider. Also, the longer you stay on the net the more common patterns emerge. Common handle names and avatars not to mention writing style. These are all digital fingerprints that you leave all over the internet. If you own a domain, your real name and mailing address might be a whois search away or plug in an email address from your contacts into facebook to look them up. Yet, we seem to think that we are a lot more safer saying whatever comes to mind without thinking out the consequences when posting online. We might as well as use our real names.

Negativity Echoes

What we have is something more akin to a WWE wrestling match than civil dialogue where crowds jeer and boo the “bad guys” who are in reality not so bad and even really great people in real life. It becomes a form of entertainment where we forget that we are constantly looking to these people for inspiration and ideas while ridiculing them with snide comments.

The Value of Anonymity

However, while I agree with Jason’s plea for civility and empathy, we are talking to people in a stable, democratic, and more or less civilized society. We must not forget that anonymity can serve as fertile ground for the exchange of ideas and as agents for social change. Civility and privacy is defined by the ruling class, just look at the liberties the Bush administration took with our privacy. Anonymity is the “blood barrier” of last resort that prevents government from encroaching on our rights when social checks go awry, it’s why the internet is a dark, powerful force in changing communist China (for better or worse is something history will show). America’s founding owes a lot to men like Thomas Paine (who would no doubt be a political blogger in this day and age) and the Federalist Papers. America’s independence and democracy was forged in the crucible of anonymous discourse led by the very leaders of the American Revolution. To sacrifice anonymity in the interest of civility and empathy would be a very steep price to pay indeed.

We Live in Public (and the end of empathy) « The Jason Calacanis Weblog

Some Things Need To Change

The Obama Campaign Significance

Barack Obama ’s successful bid for president is probably just as significant as having our first (at least openly) multi-racial president (remember his mother is white and he only met his father once or twice). He changed the nature of campaigning for good and finally delivered on the promise of information technology driven movements. Just look at the Barack Obama web site and you not only get links to Obama information on the web but links into virtually all the popular social networks and services, each with an official Barack Obama account (including an updated CV on linkedin). On top of that the site also hosts its own little social network where you can connect with others and promote the campaign. If the Kennedy’s debate against Nixon for the Presidency on live national TV was the defining moment ushering the age of television in American politics this election was the defining moment for the role the internet and social networks are to play in elections of the future. If network television brought everything to the masses, in this election, the internet brought back grass roots to the masses.

An interesting twist in this election is not only how Obama successfully leveraged the internet for a distributed grass roots campaign but how Sarah Palin unwittingly leveraged the popularity of internet memes by offering endless material for parody and innuendo from those seeking to exploit her image.

Barack Obama’s time as a community organizer in Chicago and his standing as a virtual newcomer and outsider served him well. While Obama’s campaign proved to be a demonstration of the power of social networks in spreading the message and building momentum in disparate pockets of social connections, we will have to see how and if Obama is able to maintain a meaningful dialogue with those that put him in power through the technology he leveraged so well.

Getting on the Ball with GTD and the iPhone

I’ve been experimenting with GTD (Getting Things Done) since buying an iPhone. We live in an age where there are just way too many things to rob us of our attention and keeping us from focusing on the things that matter the most. Life is a series of actions that combine to a greater or lesser effect depending on what those actions are and how they are structured. In order to focus on the greater things in life you need to either eliminate the lesser tasks or handle them as efficiently as possible.

The reason why I chose the iPhone to revive my GTD workflow is simple: ubiquity. I will always have my phone with me no matter where I go. Out of all the apps I chose Appigo’s Todo ($9.99) simply because it is the best one out there. It syncs with web services Remember the Milk and Toodledo but works perfectly fine as a standalone. I spend my time at work in front of a Windows pc but use a mac at home so some kind of web service integration is a must. I use Remember the Milk simply because it has a good feature set and there are a variety of tools for posting tasks, such as twitter. So far Appigo Todo is the only native iPhone app that has web synchronization built in.

The reason why I like Appigo’s Todo is simple:

Focus on standard task management

They don’t try to put their own spin on GTD that you must adjust to. They give you a standard, yet well thought out tool set. There’s a quick add button for tasks. You can set a default due date (like today), list, and/or priority level—this is one feature that makes it better than adding tasks within RTM. You can easily set repeating tasks as well.

Quick Context Switching

You can easily switch lists or show All. What’s more you can filter All to selectively ignore some lists. When you switch lists the tasks you add go into that list.


You can sync on startup or manually. I choose manually for the time being since I had a really hard time with my iphone constantly getting trapped in the “black screen of death” but since the 2.1 firmware seems pretty stable, if my iphone doesn’t crash this week I’ll definitely enable it. It was also a real lifesaver when I did have to restore my iphone since there’s an option to “reset and re-sync”. I was up and running in no time. In fact, Todo is the first app I re-installed when I didn’t have time for a full restore.

My GTD System (Obviously a Work in Progress)

Add ALL Your Tasks

There are some tasks in life that you really don’t need to right down. Breathing, sleeping, brushing your teeth, pouring yourself coffee in the morning or eating. However, for the most part, I put down any tasks that are even vaguely optional or those that tend to get ignored easily. Some examples include: exercise, reading the paper, throwing out the trash on the designated trash day, drink medicine, etc. You only have to add these tasks once with a proper repeating schedule and never worry about them again. By putting all your tasks on the list you can forget about it. Just plan out your day, decide on a sequence of tasks and come back to the list as you knock them off. You don’t need to juggle them in your head any more.

Put a Deadline on them All

A task without a deadline is merely an intention. Let’s be realistic. Suppose you have a task called “write my great American novel” sitting at the bottom of your list without so much as a deadline. Do you think you’ll ever complete it? No. It’ll just be there looking up at you, nagging you silently but not nearly enough to get you to actually work towards completing it.

If the Task Takes More than a Couple Days to Complete, Break it Down

Back to our big task of “writing a novel”, smacking a deadline on it alone will not ever make you a novelist. Why? Because you will never write a novel in one sitting. Any task that takes longer than a couple days or even a day needs to be broken down. If you want to write a novel you can start by setting a recurring task for every day or two to “write one page of my novel”. If each chapter is 60 pages, you can set another task to “finish up current chapter in novel” with a deadline two months in advance and so on.

This really applies to any major undertaking whether it’s a medium-sized project at work or hosting a party for a friend (find a venue, email friends, choose a present, etc.) that are ultimately a series of related tasks. You need to break them down into chewable bits you can chip away at on a daily basis. It’s the only way you’ll achieve your greater goals. Just think of how many excruciating hours professional musicians practice scales and standards. They don’t simply say, “okay, perform at Carnegie Hall next month”. Same approach here.

Breaking big tasks also have the added benefit of helping you map out an informal course of action. For example, say you add a task to “host Bob’s birthday party”, you then need to break it down into a series of smaller tasks: pick a date everyone can attend, get party supplies (add a list in the memo section), pick a venue, finalize reservations two days before, collect money for surprise gift, order gift from store, etc. See, just the act of breaking a big task down gives you a course of action you can follow. Stagger the due dates into the proper sequence and then all you have to do is check them off. No frets or worries. Of course, as you go about these tasks new ones will pop up and you’ll have a better chance of discovering holes in your plans before they become an issue.

Make Your Call

Inevitably, some tasks are always going to be lagging. My advice is to either reschedule them or reconsider whether you really need to do them. Maybe you can just cut this task out of your life for good and be better for it. Letting tasks fester in the overdue department only lowers your motivation. If you can leave the task overdue so long then either it’s unimportant or you have some serious procrastination problems. If it’s the latter you simple need to DO IT. Really. Ultimately all tasks come down to the simple question, “are you going to do it or not?”. The only answers are “yes” or “no (physically or mentally impossible, too lazy or just don’t want to do it). You need to make your call and live with it. You can’t have a task list full of intentions. If they are simply overwhelming then you can break them down or translate them into something more realistic.

Stay in the Zone

It feels good to be constantly checking off tasks that you are getting done whether they be errands or milestones in achieving your dream. It also gives you a good idea of what your capacity is. Once you get yourself in a good cycle you can start experimenting with structuring your tasks. What combination or sequence of tasks work best for you. How can you multi-task mundane tasks (like getting back to a colleague while a software installation is running). Which tasks take longer than you thought. The act of writing tasks down and completing them creates a virtuous cycle and ultimately getting more and more things done. It gets to the point where you almost wonder, “hey, maybe I don’t need task lists at all, I can just focus on doing it”. Of course, you don’t want to give in to that temptation. You simply need to find bigger goals to work towards.

So far, the combination of my iPhone and GTD has helped me to get more things done in less time and keeps me from wasting time or avoiding essential tasks altogether. I’ve been able to juggle a variety of obligations more deftly than ever and focus more. However, the best thing is that it opens room for improvement.

Garbage In Garbage In

The main problem with our digital lifestyle is the fact that there’s too much garbage. What makes it worse is that we have an entire generation raised on this proliferation of garbage regurgitating more garbage. Consider me guilty of this.

In an ideal world we’d cut out all the waste and focus on what matters but instead what I find is more people are simply tuning out. It makes more sense than trying to keep up. Humans don’t scale, corporations do but only to the limited extent to which you relinquish control to autonomous groups.

I’m beginning to feel the only real communication of consequence happens in group settings and of course deeper personal interactions, but more people are shying away from that.

All these so-called communication tools whether devices or web service just hook us into fire hydrants. We have to constantly mind the valve and water source. In real life the people we hang out change naturally with time and where we stand in life. We meet friends of friends through friends, see familiar faces in familiar spots. The web still has potential to evolve but it will take something really innovative for people to fully tune in.

A Shaved Head

I got a haircut that took me from neo-hippie to shaolin monk in under 10 minutes. Oddly it wasn’t as shocking or liberating as I expected. Head felt lighter but not necessarily cooler. The main difference was other people’s reaction to it since I’ve always had long hair.

The Pros
5 minute showers from shampoo to dry
Save time styling hair
It’s a standard and universal look thanks to pop culture

The Cons
More frequent haircuts
Might need different wardrobe
Head exposed to the elements

Blogging is Bad for Your Health

According to the New York Times, bloggers are under stress and suffering a variety of health issues trying to keep up with the game.  So please tell me something new.  Like all good link bait, even people like Marc Andreessen are biting.  Of course, journalists should know.

Two weeks ago in North Lauderdale, Fla., funeral services were held for Russell Shaw, a prolific blogger on technology subjects who died at 60 of a heart attack. In December, another tech blogger, Marc Orchant, died at 50 of a massive coronary. A third, Om Malik, 41, survived a heart attack in December.

Other bloggers complain of weight loss or gain, sleep disorders, exhaustion and other maladies born of the nonstop strain of producing for a news and information cycle that is as always-on as the Internet.

In Web World of 24/7 Stress, Writers Blog Till They Drop – New York Times

It comes as a total shock that sitting in front of the computer all day digesting an endless stream of information with minimal social interaction in a highly competitive field would actually cause a blogger’s health deteriorate.  I’ve always enjoyed New York Times articles for their quality content.

Michael Arrington’s quote really shines in this article, love him or hate him, the old dog’s got a couple tricks in him slipping some humor into a great display of deadpan sarcasm.  You can almost see him giving pertinent readers a virtual wink.

“I haven’t died yet,” said Michael Arrington, the founder and co-editor of TechCrunch, a popular technology blog. The site has brought in millions in advertising revenue, but there has been a hefty cost. Mr. Arrington says he has gained 30 pounds in the last three years, developed a severe sleeping disorder and turned his home into an office for him and four employees. “At some point, I’ll have a nervous breakdown and be admitted to the hospital, or something else will happen.”

“This is not sustainable,” he said.

Yeah, a couple million dollars a year and employees to write for you isn’t sustainable.  I’ve been blogging for a while in a variety of incarnations and all I can say is, hang on to your freaking day job.  People making money off this get early signs of success while the rest of us manually spit out minor Google fodder that helps make Larry and Sergey rich and richer.

UNIX Everywhere in the House

I just found out that my DVD/HDD recorder is probably a UNIX box. No way of finding out for sure as there is no network connection but it seems so. It’s a Pansonic I believe. Toshiba makes a more geeked out version that I might buy at a future date with full networking and even file transfers to other network connected computers. I guess it’ll depend on whether I’ll watch that much TV on the commuter train or not.

I found out all this while researching ways to get TV programs onto the iPod Touch, yet another UNIX machine. I also hear that there are a few smart phones essentially running UNIX too. You wouldn’t know it from the number of devices with the fabulously ghetto Windows Mobile sticker on it but UNIX is really the unsung hero. Too bad these Japanese appliance manufacturers and all other vendors like TiVO can’t do more to coordinate their efforts. Of course, that would mean choosing a single or family of a UNIX distribution and setting up a means of contributing back improvements that would help the competitor.

Such fragmentation will probably reduce the risk of keeping UNIX alive and viable by spreading it out across various manufacturers. It might go against the values of some open source hippies to see corporations making a pretty penny off of community-driven projects. Still I would say it’s much better than having Microsoft or Apple dominating appliance operating systems. Plus, it might open the door for standard UNIX systems to connect with such appliances.

One thing that sucks is that these companies try to play down how much UNIX is in their system and what they’re doing to push back some contributions. I would say that there is a culture of fear preventing companies from owning up and acknowledging how much open source they use since it opens up a Pandora’s box of potential legal issues ranging from blanket lawsuits emanating from Microsoft’s blanket legal attack on supposed UNIX infringement to GNU and other open source (I use this term loosely) “promoters” launching attacks on enterprises eating a free lunch.

Other than that UNIX is a good match for appliances because it’s light-weight, infinitely hackable (since the source is all there), and compatible with any platform (as stuff written in C compiles to most processors). I’d love to see a trinity of UNIX, Apple, and Microsoft with M$ slipping into the sewer dominating IT. We really need to think of the future.

As much as I like Apple, if there was an equally attractive open source alternative, I would gladly switch. At the very least we need some good competition from a closer cousin. Of course, I doubt I’ll ever be SSHing into my toaster to execute a command but who knows…