Moved my Blog – Dale Thoughts

Hi all,

I moved my blog to . Hope to see you there!




Green Chile, Navy SEALs, and my ever changing life philosophy

I spent this past weekend in Albuquerque, New Mexico attending a friend’s wedding. Blair, the bride, was a friend I met while teaching in Egypt. She was planning on returning to Egypt to resume her studies there, but of course, the revolution changed her plans and she returned to New Mexico. Not to long after she was engaged and set a wedding date.

In case you are unfamiliar with New Mexico, the local cuisine is appropriately called New Mexican food. It’s a twist on regular Mexican food, the primary ingredient being green chili peppers. They are awesome. I am going to find some in Portland.

During my New Mexican meals and talks with old and new friends, I found myself reflecting on t he past few years of my life. There have been dramatic changes to my life plan since college. Each deviation that occurred has provided the opportunity for learning and growth, though the lessons themselves were not easy to identify at the time.

A while back I read this humorous but prescient College Humor piece that basically said that progress in life is made by recognizing how much of an idiot you were. Every two years or so you reflect on the previous two years of life and recall how naïve and silly you were to hold the particular life views you held. You realize that the world does not work as you once believed and that your current world view is really how the world works. This lasts for another two years and then the cycle repeats.

I would like to use this post to describe some of the “lessons learned” from the past few years of my life. I do not intend this to be advice for others. I’ve reflected upon the same episodes of my life and have concluded different things at different times. I’m sure when I do this post again in two years I will have different things to say, but that’s ok, I warned you.

What I consider to be major episodes of my life


College (2005-2008)

I went into college with a Navy ROTC scholarship. It was my intent to become a commissioned Naval Officer and more specifically, be accepted into SEAL training. The first two years of colleges was spent preparing my mind and body to become a SEAL. Since I knew that this is what I wanted to do with my life, I did not spend much time exploring other activities and interests in school. Frankly, I just thought most everything else was boring. Parties were fun, classes were mostly lame, and an inordinate amount of time was spent trying to attract girls [Note: The best thing you can do is get a life and stop worrying about girls]. My grades weren’t super great, but I made a conscious decision to put in the minimal amount of effort needed to get what I thought were acceptable grades.

Much of my mental energy was dedicated to thinking about becoming a Navy SEAL My close friends were fellow midshipmen who were also trying to become SEALs. I had a fantastic time bonding with these guys over workouts and beer. We even had an enlisted SEAL who was going through the NROTC program to become an officer; he became our mentor. He taught us a lot and joined us in our semi-frequent Margarita Friday’s where we drunkenly discussed…everything. It was fantastic.

Lesson: Being dedicated to a goal can be a wonderful experience. You become close friends with those who share your goal and your life feels purposeful. However, extreme focus may lead you to judge and exclude other people and activities unfairly. My whole worldview was framed in the context of trying to become a Navy SEAL. Had I gone to BUD/s in those years, I believe I would have made it through.

Study Abroad (Spring 2008)


I had been taking French since I was in 7th grade. I decided to minor in it in college not because I had a special love for it, but rather I placed out of the intro classes and it seemed like a shame to waste all those years spent learning the language.

I went to study abroad in Marseille, France in the spring of 2008. I stayed with a French host family, met my girlfriend Erica (a fellow GW student), and developed a love for travel. This was the first time since I entered college where my primary group of friends  were non-NROTC types. It was strange to hear about career goals that didn’t involve warfare of some sort.

I started enjoying the world of sidewalk cafes, and thoughts of alternative career paths swam around my head. At this point, I could not admit to myself that maybe there were other things to do than become a Navy SEAL. I would briefly think about jobs that would allow me to travel and not worry about passing fitness tests, but then criticize myself for being weak minded. How could I not want to be a Navy SEAL?

During my semester abroad, I traveled to Morocco, Italy, Turkey, and Greece. I loved it. I loved trying new foods, meeting new people, and achieving a truly relaxed mindset. I told myself that when I was finished with the Navy, I would find a way to travel long-term.

Lesson: Its ok to have doubts about your goals. The goals that you’ve been working for the longest will be the hardest to critique. I wish I had the courage at the time to discuss it with others.

My last year in college (2008-2009)


I should have paid more attention to the symptoms. My workouts were slipping and I was not in great shape. I was still thinking about everything I needed to do to get accepted into BUD/s, but I was no longer excited about it. It became a chore. When I heard that in November 2008 that I was accepted into BUD/s, I was excited, but this excitement did not last long.

For the second half of my senior year, my attitude towards BUD/s alternated between excitement and dread. I talked with several friends who went to BUD/s (and completed it) in previous years and they said this was normal. I convinced myself I was normal for feeling that way, but it became harder and harder to get excited about it.

I graduated college and was commissioned into the Navy as an Ensign in May 2009.

Lesson: It’s easy to rationalize your own worries, especially if your friends help you rationalize it. You owe it to yourself to truly explore the signals your mind is sending you, not just label them as normal aberrations. It may turn out to be nothing and you can continue along your original path (as my friends did), but it may turn out your need to make a serious change.

BUD/s (2009-2010)


I checked in to BUD/s that July. They were limiting the number of officers that could be in each class to about 10-12. What this means was that I and about 30 other officers would be stuck in what is called PTRR until we were assigned to a class.

If the signals weren’t loud and clear before, they were now. PTRR is easy compared to anything you do in a BUD/s class. You go through two evolutions in the morning and you’re done for the day unless you have collateral duties. Evolutions would be some sort of workout. This could include swims, PT sessions, obstacle course, or beach runs. I dreaded it every morning.

Every morning I would wake up depressed about going to PTRR. Many of the other officers were depressed but for a different reason: they wanted to start training. They thought they were losing their edge and just wanted to start and finish BUD/s so they can move on to the business of being a SEAL.

I was out of shape relative to the other members of the class. I sometimes enjoyed the workouts, but that was rare. I thought that if maybe I just got to the point where I would class up, all my fear and dread would go away. Maybe something magical would happen and I would start enjoying everything.

I was scheduled to class up in January after winter leave. Ok, I thought over Christmas I would get my mind straight and I would come back mentally strong and ready to kick butt.

The first day back I still hated it. The second day back I worked up the courage (if you can call it that) to quit.

Lesson: You can only fool yourself for so long before your situation becomes intolerable. In hindsight, I consider myself lucky that BUD/s is a place where you either have to commit or leave relatively quickly. Had I actually classed up right away, I would’ve been gone within a few weeks. Because PTRR was easier, I dragged out the process longer than I should have. This lesson would serve me well when I’m teaching English in Egypt

Egypt (August 2010-2011)


The Navy discharged me that summer. I had applied to a different program in the Navy, but since they were making budget cuts, many officers that dropped out of their initial training program were given the boot.

This was a mixed blessing at the time. It was tough as I was still strongly attached to my identity as a Naval Officer (if not a SEAL).  Though I had become a little jaded with government work, it was difficult getting over something you’ve worked so hard to achieve for four years.

Nonetheless, my desire to travel sent me to Egypt where a friend helped Erica and I obtain teaching jobs at her school in Cairo

It turned out that I wasn’t a big fan of teaching either.

The private school I taught at didn’t particularly care about what the students were learning. They loved acting like bureaucrats and detested being educators. Most of the students did not care. They felt entitled to good grades regardless of their performance.

Needless to say when the revolution kicked off, I decided not to return to the school. I tolerated working there for a while, but I was not passionate about the job. It paid well and it allowed me to travel a bit, including a trip to Beirut, but the money did not make up for the suckiness of it.

The worst part about this job was that it made me more hateful. I began hating the students, the administrators, and the Egyptian education system as a whole. The anger began to spill over into other areas of my life in Egypt. I would become more frustrated with certain aspects of life in Egypt than if I had not been teaching.

Following a two week trip to Thailand, I returned to the US to get TrekDek off the ground and find more meaningful work.

Lesson: If you hate your job and you’re able to, leave as soon as possible. If you must put up with the job, figure out what your goals are and do your best to achieve them ASAP. Staying at a job you hate is bad for your soul.

Lesson Summary:


  1. Being dedicated to a goal can be a wonderful experience. However, be aware that you might be missing out on other activities that can help you grow as a person.
  2. It is ok to have doubts about your goals. The goals that you’ve been working for the longest will be the hardest to critique. Make sure you are honest with yourself.
  3. It’s easy to rationalize your own worries, especially if your friends help you rationalize it. You owe it to yourself to truly explore the signals your mind is sending you, not just label them as normal aberrations
  4. You can only fool yourself for so long before your uncomfortable situation becomes intolerable.
  5. If you hate your situation/job, change it as soon as possible. Don’t drag it out any longer than you need to.

My next post I will describe the things I’m learning from my current situation as an entrepreneur/unemployed guy in Portland.



PS: There’s a funny MSNBC video on SEAL training that I am in briefly in. You can see my sad self between minutes 1:01 and 1:04 going through the low crawl on the O-Course

How TrekDek Cards came to be a part of the World Domination Summit

From Egypt to Portland: TrekDek, Chris Guillebeau, and the WDS

Last weekend I was able to volunteer at the World Domination Summit in Portland, OR. How did I even hear about this oddly named conference? Well, it all goes back to a time when I was in the exotic land of Egypt.

I had landed a gig teaching English at a private school in Cairo. Teaching was never what I had intended to do, and it was really just a means to facilitate travel. In any case, I was trying to figure out how to get TrekDek up and running.  The process of figuring out how to get this business off the ground involved reading a lot of books, one of which was of course, The Art of Non-Conformity by Chris Guillebeau. I  e-mailed him to tell him how much I enjoyed his book and maybe get some feedback on TrekDek. To my surprise, he actually responded. Awesome.

Flash forward to May 2011. I moved to Portland because a) it is an awesome city and b) I thought it would be a great place to launch TrekDek. After my first batch of cards was made, I remembered that Chris lived in Portland. I sent him a few decks and once again to my surprise, he enjoyed them so much that he wanted to put them in all the WDS gift bags. Score! It was at this point that I looked up what it was. After reading about it, I couldn’t pass up the opportunity to be there personally to see all the awesome speakers and get some feedback from the WDS attendees. I begged and pleaded to be able to volunteer for a few weeks and I am happy to say my strategy of wearing the WDS staff down payed off.

The Best Part of WDS

Hands down, the best part of WDS was meeting the fantastic attendees. I’ve never met so many people looking to live life on their own terms. Most of my peers from college are struggling to define themselves through their careers, or attempted careers (sucky economy and all). It was refreshing to meet entrepreneurs, travelers, pastors, speakers, bloggers, and translators. I won’t even begin to tell you how many side projects that were being discussed.

The beer tour was a fantastic opportunity to meet some excellent WDS peeps (shout-out to Group 1). I had a long talk with Caleb Wojcki (@calebwojcik) about his upcoming wedding and plans for a long trip to Bali. Though I can’t say I’m not a little jealous of his upcoming adventure, it was inspiring to hear him talk about his aspirations and the concrete steps he is taking to get there. I wish you the best of luck (though luck has very little do with it) on your journey.

TrekDek reception

 Though I don’t mean to toot my own horn, I received very positive feedback on the TrekDek Playing Cards. In order to work TrekDek into the conversation without sounding too much like a sales guy, I had to make my own TrekDek jewelry. Now I know what you’re wondering and no, there aren’t any pearl TrekDek necklaces for sale. What I ended up doing was punching a hole through a pack of TrekDek cards, running a book ring through it, and attaching it to the name tag chain everyone was wearing. This was a much less awkward way of talking about the cards because most of the time, the person I was talking to would ask “why the heck are you wearing those?” It occured to me later that it wasn’t obvious that I was the guy behind the cards and not just a huge fan.

There were a couple of suggestions that a few people had for the cards:

A. Make it obvious that they double as actual playing cards

B. Have a website where people can upload the stories of their adventures that took place while accomplishing a TrekDek challenge.

Both are good points. In fact, I’ve already been working on B for a quite a while. Its still under development but you can test out some of the features here . Don’t be too harsh, it is still far from complete but I would love your feedback.
See you next year

I saw the amount of people that signed up for next year. All I can say is…Wow.

Good luck on your quest for world domination and I will see you in a year!




My Japanese mom and what she thinks about entrepreneurship

So I recently sold my first few decks of TrekDek Playing Cards (yay!) and naturally told my parents about it. My mom, always sending me random things in the mail, sends me a congratulatory card.

The Card. Cute right?

So I open it up, and there’s a nice, grammatically incorrect note.


And then I open the rest of the mail to find…

The classifieds! There was a note attached that said "Just in case."

Oh Mom…



Purchase TrekDek Cards Now!

You can purchase TrekDek cards in two places:

A. From

B. From Storenvy . Use the coupon code VAGABOND to get 15% off!

Hope you enjoy them!



First month as a start-up founder in Portland, OR

For those of you who don’t normally read this blog, about a month ago I moved from Lexington, MA (Yes, the famous shot heard around the world Lexington) to Portland, OR. I moved to Portland for a few reasons. My girlfriend lives here, my (now former) co-founder lives near Portland, I like the city, it has a small but growing tech scene, etc.This blog post is about my first month as start-up founder in Portland.

Getting plugged into the Portland Tech Scene
I knew coming from Boston that Portland’s start-up / tech scene would be significantly smaller. That is exactly why I wanted to come here. When I was in Boston, I went to a few networking events and met some awesome people, however, I was definitely a small fish in a big pond. Part of the appeal of Portland was that the pond in question is significantly smaller. Though I’m still a small fish, it has been significantly easier and more rewarding  to work with a smaller group of tech and start-up people. I’ll give you some examples:

a) I got to meet Rick Turoczy of the Silicon Florist and am currently helping him out with a few guest posts for the blog

b) Interviewed Darius Monsef IV, the founder of ColourLovers and YC Alum, for a Silicon Florist blog post. Also got to discuss TrekDek with him and received some great feedback (Thanks for backing my Kickstarter by the way).

c) Attended the launch event for the Portland Seed Fund and got to talk with one of the fund managers, Angela Jackson, for a bit. Oh yea, apply by May 31 if you want to be considered for the summer class.

d) Met some fantastic entrepreneurs and start-up founders, including Jason Glaspey, the current Product Manager at Urban Airship, PeeKay Chan from the soon to be launched HubGenie, and Sean Keener and Riel Manriquez from BootsnAll.

When I arrived in Portland I deliberately sought out people heavily involved in the Portland start-up scene. What I didn’t expect was how friendly and welcoming they all were. I pretty much cold-emailed everyone and they were all happy (I think) to meetup for coffee and chat for a bit. I am extremely appreciative of all the people that I’ve met here. Though its possible that tech peeps are just a friendly bunch no matter where they are, I really believe the laid back Portland vibe has something to do with it. In Boston, most of the entrepreneurs and investor types I met were very friendly, but it was a different mind-set all together. It might just be a function of the size of the tech crowd, but I think its also a city culture thing. I would love to read a blog post comparing Portland to Silicon Valley.

Finding a co-founder in Portland

When I arrived in Portland, I had a co-founder. Unfortunately for me, it turned out that he was too busy to take on that co-founder role. He was busy managing his own software that he licenses out as well as several rental properties that he owns. C’est la vie. No hurt feelings or anything but that put me in the position of having to find another tech co-founder.

Progress to date? Several leads but haven’t found one yet. The most promising leads have actually resulted from non-tech related activities. I went to a few Meetups. One was a travel group and the other was a Portland New In Town book club meetup. It just happened that there were a few coders in both groups that liked the concept and seemed fairly interested, but those conversations are stills taking place.

Most of the coders that I’ve met through tech related activities have also been interested in the concept, but it seems as if they are all happy doing consulting work and working on some side projects. I don’t know how this compares to the valley, but that seems kind of Portland like as well. There is definitely an emphasis on “just enough success” and working to live. Though frustrating for someone looking for a co-founder, its great from a lifestyle perspective.

I think I may have to change my approach quite a bit. Suggestions?
The roller-coaster emotions of being an entrepeneur

My personal experience in this area seems to be fairly typical. Most of the time I’m fairly optimistic. My happiness is highly correlated with discover different possibilities for the project, meeting other entrepreneurs, and making incremental progress on the project. The severe semi-frequent depression is highly correlated with mean hacker news comments (amazing how affected I am by anonymous feedback), perception that the project is not progressing and you can’t do anything about it, and the occasional glance at my dwindling bank account. Overall though I think it helps to be in Portland in both cases. When you’re happy, you feel so lucky that you’re in a great city with lots of natural beauty around it. When you’re bummed, well, you’re still bummed but at least you’re still in a great city with lots of natural beauty around it. Boston is a little too much city and not enough nature for the emotional ups and downs of a start-up founder.

Job Search

There’s a certain piece of advice that Portlanders give people thinking about moving to Portland. It is BYOJ, or Bring Your Own Job. Indeed that seems to be the case here. Granted, I haven’t been trying very hard to get a job, but I’m also trying not to end up in a job where I will want to throw myself off the Burnside bridge. I even wrote a blog post about one of my job interviews at a law firm. This may not be a realistic attitude, as I either have to start generating revenue or be homeless. Lame. If anyone reading this post knows about any start-up jobs for non coder positions let me know.

Concluding thoughts

If you want to start a start-up in Portland, I think its a great place to do it. If you want to raise some serious funding, you’ll probably have to leave. But, in the early pre-launch stages, I don’t think you can beat the lifestyle or the culture of Portland. I imagine that the most ideal scenario (other than having funding) is having a part-time job that pays the bills while you work on your start-up. Working part time here is something that is celebrated so no worries about being shunned.



Kick Starter – Raising money to produce TrekDek Cards

Hello all!

I’m raising money to produce a batch of TrekDek playing cards via kickstarter.

Check out my kick starter page here .

I’m trying to raise $5000. If you pledge

$1 – you will receive one TrekDek card of your choice.

$26 – A deck of TrekDek playing cards.

$52 – Two decks of TrekDek playing cards. One for you and one for your traveling friend. I will even send it to your friend directly.

I’ll keep posting updates on the blog about my progress.