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The Curse of Capability

I had an interesting realization recently when discussing funding options for a web site I built. For some background, I’ve worked on it occasionally on weekends (and a few multi-week sprints) throughout the last 4 years. It has slowly grown up to be a pretty robust lump of technology. For it to have a chance at taking off, it will need serious attention from a bunch of different angles: design, user experience, back-end optimization, sysadmin/devops, content acquisition, moderation, and marketing.

There are always valid arguments in favor of and in opposition to raising capital. After a couple of years of having no intention to seek funding for this project, I started to lean in favor of it. Part of it is manpower and not spreading myself too thin. Another part is skill set—my skills are too broad.

I’m pretty good at a few things (interactive development; “making stuff move with code”), but much less so at a bunch of other things. I can do various things under the “big D Design” umbrella (from product to user experience to graphic design), but that doesn’t mean I should. My design work is definitely inferior to those who specialize in it. I can do database administration and query optimization, but that doesn’t mean I should. My low-level systems prowess is definitely inferior to those who specialize in it. Basically, I have the ability to build a fully functional and fairly usable proof of concept, but not an all around amazing product. I can bring an idea to life, but beyond that, it’s best to let specialists take it from there.

Throughout most of my career, I’ve always worked alongside complementary specialists, allowing me to focus my attention to my own specialty. My best work has always been the work I’ve done with good teams. My best solo work, while sometimes being technologically innovative, is nowhere near as well-rounded or impressive.

So, I hit a roadblock. If I were talking to investors with an idea, a plan, some slides, and no ability to pull it off myself, an investors answer would simply be, “Yes,” or, “No.” However, because I technically can build everything from front to back, the answer becomes, “No,” or, “Come back after you launch it and start getting some traction.” If an investor has the option to see the product in action and gauge real-world interest, why not wait and see?

Well, I need to get back to my client work now…

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Homeless for a year

Here's @brianshaler waiting for the train. PLEASE hope w... on Twitpic (looks like Twitpic isn’t working right, and I can’t download and upload their photos via my phone.. I’ll try to fix the image when I’m not restricted to my phone)

I didn’t set out to last any specific amount of time. I thought 6-12 months of full-time travel—the much more glamorous way of saying homeless—was doable, considering I had already spent a few years traveling part-time while working. On a few occasions, I had used my 1-week carry-on bag to last 4 or more weeks. I figured as long as I could find a way to do laundry every week, I could travel indefinitely.

The core of the experiment was about living expenses and sustainable travel. Traveling, even on a tight budget, is very expensive. The cost of food, lodging, and transportation while traveling can easily match or exceed your standard cost of living. Full-time travel could thus double your monthly expenses. But what if you were able to eliminate the first part of the equation and only pay living expenses wherever you currently are? What if you could go to Rome for a month and not have to pay for the month of rent and utilities back home?

To keep travel cheap, on a per-day calculation, you need to travel slowly. Going to another continent for one or two weeks results in a very high per-day cost, but you can save on lodging by staying longer (weekly rates are lower than daily rates, and monthly rates are lower than weekly rates) and lower the per-day cost of transportation by putting more time in between flights.

I decided a year ago to try this out. I rented a studio in the Bahamas for 35 days for $600, a room in DC for 4 weeks, a hotel in Germany for a month (which was thankfully reimbursed by a client), a hostel in Budapest for 3 weeks, a mountain-top hotel in the US Virgin Islands for 3 weeks, and a cabin in lower Manhattan (which I had to see to believe) for 5 weeks.

So, 6-12 months. When will it end? When will I “settle down” and return to traveling only part-time, 1-3 weeks per month? It’s an internal conflict I’ve had since the 6th month. The full-time travel is exhausting, stressful, and both physically and mentally taxing. But at the same time, I’m in a position to travel longer and farther than I would otherwise be unable to. Giving up now would feel like squandering the unique opportunity I have. I have never been to Asia, Australia, Africa, or South America, and this would be a great time to do it.

The jury is still out. It could be up in the sky, for all I know. Speaking of which, I am now on my descent into Charlotte, North Carolina. Time to turn off and stow all portable electronic devices.

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“We want you to move to SF.”

In 2008, I decided to change jobs. I reached out to employers I had deflected while happily working away on exciting projects. I don’t remember what made me choose the company I ended up working for, but it very well could have been the opportunity to travel.

They wanted me to move to SF and work in their headquarters (they had a satellite office in Santa Cruz), but they ended up giving me two job offers. One included a high salary, a signing bonus, and required I live in SF and work on-site full-time. The second offer had about $40,000 chopped off the salary, no signing bonus, and allowed me to work from home, while visiting the office for at least 2 days per month.

For almost 3 years, I was in SF every calendar month, and for the last of those years, I subletted an apartment there.

The brilliant thing, though, is this: my reduced salary was still very competitive against local Phoenix salaries, and the yearly travel cost was less then the difference. It was a win-win. My employer saved money while paying me fairly well and covering my travel expenses.

While in Phoenix, I got to live the work-at-home freelance lifestyle (i.e. flexible hours and no work/life balance), which helped me get actively involved in the Phoenix tech community.

Oh, how I miss direct deposit..

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“Finally, a REAL Hungarian man”

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I was hanging out with a new friend I made in Budapest, via Twitter no less. A homeless guy approached us, stood in front of me and started speaking in Hungarian. My friend stepped in, speaking Hungarian to the man, gave him some change, and then the man left. My friend translated what the man had said to me. “Finally, a REAL Hungarian man!” My friend set him straight. Just a funny looking American.

In Hungary, almost every person on their paper currency features some sort of facial hair. Most of the statues, too, don mustaches and beards.

My handlebar mustache was uncommon among the people there,but it seemed to fit right in with their money and art. Their history.

I was a blast from the past.

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The beginning of a journey

Today is Thanksgiving, and people are saying what they are thankful for, including life-changing, path-altering things. If there was one moment in time, a single realization, or a crucial decision which set me off on this path I have taken, I think I know what it is. When I stopped to think about it, I was surprised by the answer.

I’ve seen this type of instant occur for other people—in some cases, I’ve been told I was there for it. Something happens, and opens a new door for you or gives you an all new perspective. You walk through this door, even though it feels strange, like uncharted territory. That leads to something else happening, and then something else. It’s a chain reaction that, once set in place, will continue to move you in new directions, even if you don’t realize your new life can be traced back to on event, person, conversation, book, or whatever.

This chain reaction, in a less combustive term, is the path of your life. Is your life stuck in traffic on the highway with everyone else, going to a 9-5 cube farm job? Sometimes it’s not your decision to get kicked off that highway and into the woods, as you can see in the Lemonade documentary. In most cases, if you really want to keep that comfortable, consistent life, you can fight your way back on it. So whether or not it’s your choice to get off the beaten path, it’s up to you to stay on it and see where it’ll take you. This decision is the beginning of a journey.

Setting off on a new path doesn’t necessarily require quitting your job or getting laid off.

After my path-altering realization, I kept my job for a couple of years, and then I got a new job and worked there for almost three years. So for me, entrepreneurship only came after many other things happened and I achieved what I referred to as exit velocity. At some point, it did become inevitable.

In 2005, I realized that even if I reached the peak of my career, having a good portfolio doesn’t make you an industry leader. At the same time, I was starting to wonder how Digg was taking off, even though it was the same content as Slashdot. I realized digg was primarily successful because of Kevin Rose, who had spent years on one of the only nationally broadcasted TV channels that focused exclusively on technology. That gave him an incredible amount of exposure within the tech industry. If you or I had launched Digg at the same time he did, it very well may have floundered, as the first 10,000 users of a User Generated Content site are the most crucial when going up against an incubant like Slashdot. When people heard Kevin Rose had founded Digg, many surely signed up simply because his name was attached to it.

That realization in 2005 set off a series of reactions that eventually led to my change in jobs, starting my business, and my world-wide couch surfing adventures. Digg was where I started getting my name out in the tech industry, which is how my next employer found me. I built simple applications that crawled Digg’s data and allowed Digg users to explore and interact with it. My name was plastered all over it, in hopes that it would start to look familiar among people in the tech industry.

When I signed up for Twitter, it seemed very similar to Digg, except more personal and more interactive. Twitter was primarily made up of people in technology, and thus people I wanted to get my name out to. I did the same thing I did on Digg. I ran experiments and developed simple applications, such as twitter-based games and crappygraphs.com. Next thing you know, I was the second most-followed user on the site! Twitter, then, indirectly led to many more things happening in my life.

But would any of this have happened if I hadn’t made that realization in 2005?