I’m not the smartest person alive, and if you look into my past you’ll find all sorts of evidence to support that claim. What I am, however, is extremely lucky – and I find it’s to my advantage to be acutely aware of that. Here’s a story…

In 2003, a little over 2 years into my 5-year battle with ulcerative colitis I decided to begin two large tattoos on my arms to express coming to terms with my mortality, which came about from almost dying at the end of 2001. I had the whole thing figured out, and did everything you’re “supposed” to do to get ready to get tattooed (research your artist, decide on a meaningful concept, wait a while after you decide to make sure you still want it, etc).

While my intentions were good, my timing was not and I overlooked a pretty big detail. What I failed to realize is that getting tattooed while on a massive, ongoing dose of immunosuppressants to battle my UC wasn’t very bright. I spent a total of 10 hours getting tattooed over the course of two weeks.

About a week after my last session my right arm started to get very sensitive all over, from above my elbow down to my wrist. This followed by redness and swelling which continued for a full week. My doctor prescribed me antibiotics to tide me over until my appointment the following week to check it out. I never made it to the appointment.

On the Saturday before my doctor’s appointment, I woke up to find my arm so swollen I couldn’t bend it. It felt as if my skin would tear if I bent it too far. This was also a day where I needed to get up, get showered, and drive to Indiana to watch my friends Jake and Shondi get married.

While I was at the wedding ceremony some really awful stuff happened to my arm (I’m skipping over the gory details). I stayed at the ceremony until it was over, apologized to Jake and Shondi for having to leave in a rush – promising an explanation later – and drove home as fast as I could.

I headed to the emergency room after I got home and soon after I got there, the attending physicians rushed me into getting an ultrasound to see how deep the abscess that had been brewing in my arm had gotten (I did say the details were gory). It showed that the infection was mere millimeters away from reaching my bone. As they explained, once the infection gets to the bone, the limb is lost – from above the infection to the end of the appendage. I’ll never forget asking the surgeon who came to talk to me about my chances of avoiding surgery, and him telling me things weren’t looking very good.

They started me on a massive dose of antibiotics which I responded to extremely well, and long story short, my arm was saved. I spent a total of 3 days in the hospital and was released to recover on my own. I told you I was lucky.

For those who know me, I obviously finished what I started, though it took me a few years to build up the courage to get work done again. And when I did finally finish what was about 30 more hours of work, it was under the direction of a doctor who aided me in the safest possible way to keep from getting an infection.

The result of my bad timing and missed details in 2003 was almost losing my arm, missing most my close friend/business partner’s wedding, and almost ending the career of my tattoo artist (he said in all seriousness that if I had lost my arm he’d never have tattooed again).

There isn’t a day that goes by that I don’t see the tiny scar on my right arm and remember that my life could be a lot more difficult. Even with the best of intentions, overlooking a single detail of a decision, or being impatient as to when to make a move can end in disaster. The fact that I’m typing this with two hands instead of one is one of the main motivators to go after what I want, but also reminds me to have patience to wait for it to come.

Well, so much for taking a bunch of time off before I went onto my next gig! For those keeping score, the announcement of me leaving Threadless was 4 weeks ago to the day. However, when something that’s difficult to pass up comes your way, it’s always a good idea to reassess your plans. In this case, a bit of serendipity was involved, and I have my friend Joe Stump and my new friend Daniel Burka to thank for that.

I couldn’t be more excited about my new role as director of design and user experience, though I have big shoes to fill. Daniel has done such an amazing job in his time as creative director Digg, so I’ll be striving to keep the same level of excellent design as I work to build a team that scales with Digg’s growth.

I don’t want to get into the nuts and bolts of what’s to come, but when the time is right, I’ll be posting about it on here. I’ll also be using this blog to give snapshots and explanation of design-in-progress, so stay tuned.

Huge thanks to Jay, Kevin, Daniel and the rest of the Digg family for this tremendous opportunity, and best of luck to Daniel as he begins work on his exciting new project with Cal Henderson and Stewart Butterfield.

I’ve made the hardest decision of my life today. I have resigned my position as chief creative officer at skinnyCorp/Threadless.

As you may imagine, this was not an easy decision. What makes Threadless special is its ability to turn every single person – from our vendors to our employees – into part of a giant family dressed in ink-slathered cotton. The collective dedication and creativity of the Threadless family, as well as our beloved community, is awe inspiring.

The pride I have for Threadless is unmeasurable.

Of course, none of this has been possible without Jake. He has always had the vision and ability to wade through my onslaught of ideas and cherry-pick the ones that we both knew were best for the community and for Threadless as a whole. The decision to leave was no different. After many long discussions with Jake and our CEO Tom, we’re all on the same page that this is the right direction to take.

If I had to pick the one thing I’ll miss the most, it will be working with Jake, Tom and the rest of the executive team as Threadless continues to grow more and more awesome.

So, whats next for me?

First, I am taking some time off. In the seven years of building Threadless, the longest vacation I ever took was about 2 weeks, and that was last month. I’m looking forward to spending real quality time with my family and friends, without meetings, deadlines or other work related things getting in the way.

Next, I am going to rededicate myself to things I love. Who knows, maybe I will start skating again. (Probably not, but we can all dream). I heard a rumor that people actually travel for pleasure. I may give that a go as well.

Lastly, I will start getting involved in a few projects that are just too exciting to keep secret, but too early to talk about. I hate to do it, but you will just have to stay tuned to hear about all the awesomeness to come.

The past seven years have been amazing. While I will no longer be involved in the day-to-day grind of the company I helped create, I will remain close to Threadless not only as an owner and advisor, but through my many friends there. And of course, I will continue to be an active part of the most awesome community, ever.

Thank you Threadless; I cant wait to show you what’s next.

This past Friday wrapped up my first “class” of TechStars as a mentor. I wrote a post at the beginning of the summer about what I thought was in it for me as a mentor. I was seeking inspiration. I got much more. Looking back, I almost feel naive wondering if I’d find inspiration. How could you not be inspired by ten teams of highly motivated, extraordinarily talented people busting their asses for 3 months focusing on ideas they believe in?

As a mentor, I worked mostly with Vanilla, Take Comics, Next Big Sound and a bit with Everlater.

As the summer progressed and I spent more time with the teams, there were two feelings that I tried to constantly be aware of: interest and excitement. As a mentor, I found it useful to think of my interaction with the teams the same way I’d think about test-driving a car. Interest is what gets you behind the wheel; excitement is what gets you to floor it. It was the latter that I knew I had to keep in check, which is something I’ve never really had to do at Threadless.

For me, excitement is what brings on the onslaught of brainstorming – new idea after new idea after new idea. I’m lucky to have a partner who is equally good at disseminating the good from the not-so-good as I am with filling a sheet with different paths to take.

Being a mentor is another story. If I want to spend all of my own time coming up with new ideas, tangents of those ideas, and tangents of those tangents, then so be it. However, I learned early on that when spending time with another company who is looking to you for either specific advice, or some guided brainstorming – a wild ride of new ideas is hardly constructive.

Going back to the car analogy, think about which feeling is more likely to instigate losing control and wrapping yourself around a telephone pole. This summer I better learned to harness and control my excitement. I know that it may sound strange, but it’s true. In learning to do that, I can now see how unbridled excitement can actually derail focus. I found that keeping my excitement in check allowed me to better give the teams what they often needed – which was for me to keep my mouth shut and simply be present as they answered their own questions simply by asking them out loud.

There’s nothing wrong with being excited. However, excitement is energy, and what you do with that energy is often times more important that the fact that it exists. Just because a car can go fast doesn’t mean it always should, right?

I walk away from the 2009 class of TechStars having learned a lot about being an entrepreneur. In a lot of ways, I’ve learned more in these past three months than I’ve learned in the past seven years at Threadless. After all, it’s a lot easier to take in the minutiae of the journey while riding shotgun than it is being behind the wheel.

This past week I watched two different documentaries about skateboarders from the 80’s who lost touch with their roots, struggled to adapt to the changing environment of their profession, and ultimately bottomed out in very sad ways.

“Rising Son” is a documentary about legendary skateboarder Christian Hosoi – one of the first skateboarders to make an incredibly successful living as a pro rider in the 80’s. The creator of the then-groundbreaking “hammerhead” shaped deck, Christian not only had the skill to rise to the top as a professional skateboarder, but also had an entrepreneurial drive that in many ways helped to shape the modern skateboarding industry today.

He is now 42 years old and only recently resumed his professional skating career after twenty-year hiatus through which he battled with drug addiction and served a 4-year prison stay on drug charges.

“Stoked: The Rise and Fall of Gator” is a documentary about controversially loved and hated ex-professional skateboarder Mark “Gator” Rogowski. After he rose to fame as a professional skateboarder, Gator gained near-celebrity status in mainstream media (during what I feel was skateboarding’s “glam” period), proving that if skateboarders had the right image to match their talent, brands could be built around them (in his case, Gator was to Vision Street Wear what Jordan was to Nike).

At 43 years old, he is now serving a 39-year sentence for raping and murdering a girl in 1991.

Pleasant stuff, eh?

For both of them (though, Gator more so than Hosoi) the skill that got them to where they ended up became secondary to the image they focused on upholding. What they had in common, in my opinion, was letting their personal brand blind them from the reality of fleeting relevance as their industry shifted focus (from vert to street skating).

Because their brand was so prevalent and so strong, it didn’t allow them to be nimble enough to change with the times, which lead to a sad, far-and-fast fall from the top.

So, what’s the point?

While it may require hard to work to achieve a successful personal brand, it unfortunately doesn’t require any actual skill. In fact, there’s no inherent factor in personal branding that requires you to continue to do what you did to get there once you find success. Why? Because it’s entirely possible to achieve great success in personal branding while having literally no marketable skills whatsoever (*cough* Paris Hilton *cough*).

If you’re not careful, personal branding could easily overshadow your actual skill-set and then you’re the person who is well known… but… what was it for again?

Watching these two documentaries, I saw the parallels between what happened to Hosoi and Gator in the 80’s (and others in the skateboarding industry at the time) and the rise of personal branding in social media today. I find myself sometimes wondering “OK, I know of this person – but why? What do they do again?”. Personal brand can grant someone scene celebrity in an relatively young industry which has been built on innovation, hard work and relationships (much like the skateboarding was in the 80’s) – merely by focusing on the relationships part.

I’m not saying that it’s not important to put yourself out there – because like it or not – these days it is. However, don’t let your personal brand shift you from person to persona as it gains traction. You’re here for a reason (unless you’re the offspring of someone who already has found tremendous success), so don’t lose touch with that reason. Your skill-set that jump-started your personal brand needs just as much work as your brand does (if not much, much more).

Innovation, hard work and relationships fuel the business we’re in (or at least the one I’m in). Those values are listed in order of importance. Personal brand only deals with the 3rd in the list, and alone has little to do with industry relevance. Focus too hard on that, and your creativity/innovation and hard work suffer.

Relevance is one of those things that you don’t realize how important it is to have until it’s gone. In my opinion, that lead to the fall of Hosoi and Gator – let it be a cautionary tale for us all.

Today is getting on my nerves, and it’s the fault of a good-sized bunch of you. Did you do some celebrating today? You know who you are! Talking/tweeting about the monumental occasion that occurred just past noon – a time when the universe aligned to remind us of the gift of consecutive numbers. If you missed this “special” occasion – don’t worry, it didn’t actually happen – and it won’t happen for another 81 years.

So, what were you celebrating? 12:34:56 7/8/09. But wait… does something look a little odd to you? Me too. While “09″ is still technically, “9″ – it doesn’t create the effect most people were celebrating as if it was the Pope’s birthday. Now let’s remember what year it is: 2009 (aka ‘09). “09″ is part of a number set that looks like this: 01, 02, 03, etc. The rest of the numbers belong to a number set that looks like this: 1, 2, 3, etc. So, while technically “09″ comes after “8″ – it’s really just a square peg in a round hole.

In order for there to be real cause for a celebration, the date would have to be: 01:02:03 04/05/06 – which isn’t all that exciting, is it? That’s about as exciting as celebrating 04:05:06 07/08/09 (which is today, and the good news is that if you’re really into celebrating pointless consecutive numbers, you still have a few hours to go out and buy beer and a piñata).

However, if you really want to celebrate the single-digit number set in all its glory as it happens naturally in modern date and time conventions, then mark your calendars – it’ll happen at thirty-four minutes and fifty-six seconds past noon on Saturday, July 8th, 2090 (aka 12:34:56 7/8/90).

C’mon folks. Are we really that devoid of reasons to celebrate? Hopefully you have some party poppers left, because here’s three real reasons: you’re not dead yet, Sarah Palin is still doing amusing wacky shit, and Kevin Bacon turned 50 today.

Whew! I feel much better now. You?

I have a flight at 7:30pm to head to San Francisco to spend time with my girlfriend and also to connect with some folks for work. There’s nothing abnormal about this routine, but on this night – I’m missing out on something that I’d like to have been a part of. Tonight at 10:01 (my time) I will be missing out on being “able to choose a username for [my] Facebook account to easily direct friends, family, and coworkers to [my] profile.”

Basically what that says is that as long as I’m sitting on an airplane, I’m not in front of a computer, trying my best to snag facebook.com/jeffrey. It’s ok though, and here’s why. I’m not Jeffrey. I’m Jeffrey Kalmikoff. Besides, as long as there’s that bastard giraffe hocking toys to kids, I’ll never be the Jeffrey. And really, if Toys ‘R’ Us folded tomorrow, and I did become the Jeffrey, it’s still really just be Jeffrey Kalmikoff.

I was talking to my younger brother Josh on the phone as I drove to the airport. We discussed a few things, including a really kick-ass idea he has for a gaming website, but also talked about snagging his Facebook vanity URL. His point of view, “if someone gets what I want, I’ll just think of something better. Something wittier.” “Josh” I said, “do yourself a favor and just get your name – that URL will likely outlast whatever you found funny or witty or interesting about something like Uncler3mus (his twitter name).” “Just trust me on this one,” I said.

Even in the last 6-7 months the shift from pseudonym to real name in one’s online identity has been pretty prevalent. Many of my friends (myself included) went from pseudonym to real name – and some from real name just down to initials. What the shift really means is that everyone is seeing the value in having a single name – or at least a few names that all essentially mean the same thing. For me I’m Jeffrey (twitter), JeffreyK (skype), Jeffrey.Kalmikoff (gmail), and the one I’m starting to phase out FancyJeffrey (aim) – which at the very least still has my name in it.

I wanted to share those anecdotes to illustrate what I’ve come to terms with, and I think that it’s important that other people try to realize it as well. Your name only matters as a way to be a linkable entity to an action. Having an awesome “online handle” isn’t going to make what you do online (or off) any better than if you would have been using your own name. We’ve learned this lesson in the last 10 years as we started out being scared to have people learn our real identities online, so we created fake ones (mine used to be iFDL). The time of fear online is long since past, so it’s time to stop hiding behind “RadDude199″ or “ButteflyGrl22″.

As the time ticks away until Facebook opens the flood gates to vanity URLs tonight, maybe try to resist the urge to go after your current online moniker or pseudonym, and just go with what’s real. Just be you.

This is the presentation that I gave at the BIGOmaha Conference in Omaha, Nebraska on May 8, 2009. I had such a great time at this conference. Big thank yous to everyone involved in putting on such a spectacular event. Jeff and Dusty did an amazing job, and it was so much fun being able to hang out with all of the people who came out to the Koneko center. I also had a great time spending time with my friends and fellow speakers who both attended and presented. I hope you enjoy my talk – any feedback would be much appreciated! Thanks!

The other night, I watched a video by my friend Gary Vaynerchuk in which he was saying how he felt that the use of press releases are obsolete. His point is that you have a better chance at winning if you’re that “big fat-ass Italian uncle who tells a story and crushes it” – someone who has a conversation with people, rather than just blasting out information at people.

So, are press releases dead? A relic and a reminder of a way of doing business that once was? For Gary, yes – 100%. For others, maybe not so much. I happen to agree with Gary that if you tell your brand story well, and you have an openness with your community enough to have a dialog, then press releases are likely not necessary. However, any tactic should stay in play until it no longer provides value. So, what if you’re sending out press releases and they continue to provide value? The answer should be obvious: keep sending press releases.

This isn’t about press releases though. Not for me, at least. The bigger picture that I’m talking about here is tradition – and in particular, how tradition relates to business. A tradition is a long-established or inherited way of thinking or acting; a customary or characteristic method or manner in which one does something. Let’s look at that definition and try to extract the “value adding” words: Long-established? No. Inherited? No sir. Customary? Nope.

My issue with those words is that they all imply that there’s build-in respect. But why should we respect something in business just because it’s something that people have been doing for a long time? The answer is we shouldn’t; and therein lies the problem with traditions. But, lets first get to the core of a tradition and discuss how it came to be.

Any tradition begins simply as an idea or solution that once created value. It worked its way from idea to tradition as time went by and the idea went unchallenged – and that’s the key. Unchallenged ideas that provided value at one point are ideas rife to become traditions. This is bad for business because if you never challenge you own ideas periodically, how do you know if they’re still relevant? Think about it this way – if you go to the doctor and are diagnosed with a problem that requires medication, do you get prescribed once and take that medicine forever without periodically getting checked? If you wouldn’t treat yourself that way, why would you treat your business that way?

We’re huge proponents of this at Threadless. We’re a business that started in a very non-traditional way. We’ve told the story many times about how our business started by accident, and we grew by only doing things that made sense to us – only taking steps that we were comfortable taking. Essentially, we did all the things that seemed like a good idea at the time. With all of that said, it wouldn’t make much sense for us to not constantly be challenging our own ideas, considering that the initial success of our business was an ongoing series of trials and errors.

While working to keep traditions out of our business is a logical thing to do considering how we began, that doesn’t mean that traditions should have a place in business that began in a more traditional way. The upside to this point of view is it really doesn’t take much to “de-tradition” your business. All you have to do is simply challenge the agreed upon “good” ideas to ensure they’re still relevant. By doing that you very well may discover that all your ideas are still good ideas, and nothing changes. However, you also may find that your ideas need to be tweaked slightly to regain relevancy. That’s not a bad thing, is it?

Ideas are not immune to the aging process. Like wine, they get better with age only if cared for properly (right Gary?). This care involves always challenging an idea to ensure that it’s still relevant. Double-checking the relevancy of your ideas is an important exercise because by doing so, you get to ensure that your ideas are working for your business and not against it. In the end it’s important to realize that no one is smart enough to come up with an idea that is so brilliant that it stays relevant forever without being cared for.

So what’s the bottom line? If you have a tradition of bringing in pizza for your whole staff on the last Friday of every month should you stop? Of course not. There’s a difference between traditions that effect the culture of your business and traditions that effect mechanics. Obviously, I’m speaking about the latter. A tradition is the antithesis of a nimble organization and can keep you from seeing how ineffective your once effective idea has become.

Ever since I moved to Boulder, I’ve been super interested in startups. It’s not surprising really, Boulder is a startup kind of town. I’m not sure the exact figure, but I’ve heard something along the lines of “there’s 100,000 people in Boulder and 170 startups”. My interest in startups isn’t because I feel motivated to start a new business, but because of two reasons:

1. I love the whole process of coming up with new ideas and then figuring out how to make them a reality.
2. I love being put into situations where I’m required to learn in order to keep up.

Whether it’s discovering a niche that needs to be served, or simply just coming up with something that’d be really cool to do – I crave the excitement that comes from that initial spark of creating something new, then problem solving and learning to bring an idea to fruition.

I recently became a mentor for TechStars, a Boulder and Boston-based company that provides a bit of seed capital and a whole lot mentoring in a 3-month bootcamp format. The mentors involved are an incredibly diverse group of individuals from amazing companies. Each mentor brings something unique to the table, all in the interest of helping each of the companies that make their way through the program find a higher level of success. It’s an awesome program, and I’m honored to be involved.

More than being honored, I’m super excited to get involved in mentoring some of the companies that fit well with the area of expertise that I’m bringing to the table, which is a focus on community-based business as well as brand positioning. Granted, there’s no guarantee that I will be a good fit for any of the companies, but I’m eager to spend some more time with the groups to see where I can help.

I’ve had a few people ask me already “what’s in it for me?” Why would I spend my free time mentoring startups? Sure, I do have limited free time, and no I’m not some crazy person who isn’t happy unless he’s working (well, maybe there’s a little bit of truth to that). The reality is that I’m super passionate about ideas. There’s something so special about “the beginning” – it’s a completely different type of energy between creating an idea and sustaining an idea.

I feel it’s so important to always have a connection to the beginning of ideas, because it’s the time where you have solidified the “why” and you get innovative with the “how”. I’m sure it’s not the same for everyone, but my ability to stay creative and think about things in new and innovative ways is dependent on new ideas – even if it means coming up with some crazy idea and thinking it through, knowing that it’ll likely never see the light of day.

So, while I may have expertise to offer this “class” of TechStars, they also have a lot to offer me by way of inspiration. I’m always on the lookout to be inspired. I’m excited to observe how groups handle interaction in different ways and see how they handle the transition from idea to execution. That isn’t to say that the company I work for isn’t an unending source of inspiration (because it is), but hey – show me the law against being greedy when it comes to seeking out and consuming inspiration!

Lastly, I’m simply excited to help out. I’ve said it many times – I’m a community guy. TechStars is an integral part of the Boulder tech community, so as an active member of it – I’m more than happy to give some of my free time to help out in any way I can. So what’s in it for me? I can’t say for sure, but I’m hoping to connect and create relationships with new and interesting people. Besides, knowledge for inspiration is a pretty good trade, wouldn’t you say?