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From Below the Blog – A Five Year Retrospective

From Below the Blog – A Five Year Retrospective

Released Tuesday, 5th August 2014
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From Below the Blog – A Five Year Retrospective

From Below the Blog – A Five Year Retrospective

From Below the Blog – A Five Year Retrospective

From Below the Blog – A Five Year Retrospective

Tuesday, 5th August 2014
Good episode? Give it some love!
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This blog (formerly the “Lifestyle Business Podcast”) was started five years ago.  After four or five false starts, I meekly published an episode about the process we used to identify our first valet parking product. To this day, I get teased for my mousey mic skills, but I keep the episode live because it’s worth demonstrating that most of us start out with a shaky voice and wavering confidence.

It was a smart move to invite my business partner Ian on the show a few weeks later. From there on, a more or less weekly ritual ensued. We jumped on Skype, brainstormed a topic, and unloaded some lessons we had learned from doing business that week.

To my knowledge, we were some of the first bloggers sharing a story of location independence via a physical product business. It made for some decent, if lo-fi drama– a blue collar buddy flick. Can these guys make it?

Our little websites were always about much more than the products we were selling. We’re no visionaries. We were two broke middle class kids eyeing down many decades of 50-hour cubicle drudgery. We wanted to make great products, but we also wanted some control over our future.

In 2009, we really had no idea if things would work out. We just knew we were making a few bucks, our customers seemed to like our products, and that there was no chance in hell we were going back to normal jobs.

We used our business as a sandbox to experiment in: what if we left the country for 6 months? What if we started recruiting apprentices? What if we shared what we are doing with other entrepreneurs?

We believed from day one– “business” can be whatever you want it to be. And if that means “makes me rich” or “buys me cocktails in Thailand” or “lets me hang out with my family” or “allows me to write for a living”— you name it– we can probably find somebody doing it.


Although I often fall into the blogger pattern of preaching on high from numbered bullet point lists, I always aspired for TMBA to be more than preachy old me.

It’s more or less functioned as a long form business card. Under our names, our job description would read something like:

Hey, are you like us? Want to grab a beer and talk shop? Would you like to work with us? What’s going on with your business? Are you going to be in Singapore next weekend? Let’s swap notes.

As much as I’d love TMBA to be an outlet for my writerly aspirations (and I have many), more than anything it’s been a community. Not like an online marketing “community,” but a real honest-to-goodness community of entrepreneurs and world travelers.

Imagine our articles as the faint smoke signals of a fire that is burning thousands of feet below the blog. That fire is created by entrepreneurs who are using the internet, and the craft of enterprise, to take control of their lives.

They have met, struck deals, created partnerships, and swapped advice at TMBA and DC sponsored events. 1000’s more have met at ad hoc meetups inspired by those events. Ian and I have never cared what brand it happened under, as long as it happened. As long as cool people are getting together in the spirit of helping each other out, good things are going to happen.

*  *  *

If you were to buy me a beer, there’s a good chance you’d find me going on and on (and on) about all the serendipitous situations that have come about over the years from smart TMBA readers bumping into each other. At our monthly informal Juntos, which currently happen in about 20 cities worldwide, you can often track mutual acquaintances across multiple countries, continents, and projects.

If you are into SEO I might joke to you about the time I met Travis Jamison–about how he applied for an internship with us when he already had a 6-figure business (as a joke, I assume), to which I replied that he should forget about the internship and “just show up and hang out.” And then, of course, he actually showed up. Many good things have happened since.

If you were an app developer, I might share how I was nervous about giving a presentation on podcasting in front of a successful developer like Jesse Lawler— why would he want to hear me waffle on about podcasting?

But then, Smart Drug Smarts was born. He showed up. Jesse ended up setting up shop in Saigon and hosting a somewhat famous weekly networking party. We’ve continued to collaborate on projects like ValetUp.com and our new DC locator app. Good things have happened.

What about the time a writer named Elisa Doucette contacted me about a piece she was writing on location independence, and then ended up pitching a plan to come and help us grow our little business? No passport? No worries! She showed up. And good things have happened.

Speaking of growing businesses, I can still remember sitting in a hot apartment in NYC when I heard Taylor’s smooth southern accent waft over our Skype connection.

“Haven’t I talked to you before?” I asked.

“I actually talked to you 6 months ago. At that time I was teaching English and you told me I should stop that and get a job with an entrepreneur, so I did. And now I’d like to work with you guys.”

How could I resist? We made a deal, and of course, he showed up. Good things happened.

The world of people doing exactly what you want might not be that big. You might be able to find them. They might be right here, under a blog like this, sending smoke signals.

I don’t mention these stories in order to take any kind of credit. All these people were successful before they ran into us. If there’s one thing I’ve learned over the years it’s that people don’t “give” opportunities, you make them for yourself. I tell the stories to share my enthusiasm about having been there, and about having known these people and their adventures.

And these are just the first four examples that came off of my fingers– but I’ve heard and seen 100’s (thousands!?) of stories in person. From people who’ve commented on a post saying “I’ve got to quit this job,” to beginners asking for advice who have turned their hunger into million dollar businesses (really!), to old school brick and mortar entrepreneurs on their first world tour with family in tow. So many of us with ambitions that most think are “crazy” or at best “slightly irresponsible,” make it a reality.

This blog and our community is like a clumsy flipper in the pinball game of life— imagine us tapping furiously away until our forearms cramp– hoping to bump motivated individuals in the right direction.

That direction is always the same: back into the game, and into other motivated individuals that can inspire and inform.

*  *  *

Speaking of motivated individuals, it’s worth mentioning my chance meeting with my business partner, Ian (AKA Bossman, CEOh-yeah, Egon, E), in 2006. Bossman is the idea guy. The entrepreneurial one. He is the Yin to my Yang, the spreadsheet to my speculation, the walk to my talk. He tells the dirtiest jokes you’ve ever heard.

We became friends over a few beers and car talk. I had a tiny little Mitsubishi Eclipse that was dying for a stereo upgrade. Most days I spent over 2 hours in that car, and I wanted to listen to some loud music and to satisfy my growing fascination with these new things called “podcasts”— a format that let individual practitioners share their lives with just a microphone and a laptop.

Instead of listening to Howard Stern or other morning jocks, I started spending my commute on I5 listening to quirky entrepreneurs.  Maybe they had a handful of employees or clients and some SEO experience.  Maybe they were small time. Maybe they weren’t going to make it at all, but their perspective and experience were invaluable to me.

Bossman and I had a lot to talk about. We were both, more or less, broke. We were both hungry. We both wanted way more than what we were given.

At the time the deal went like this— Bossman comes up with the ideas and ensures our products were great. My role was to be the “make it happen guy.” Cut our partnership deal in the first place, get clients, ship product, and make sure everything was straight from a business point of view. But while the story of our business most certainly starts with Bossman, the story of this blog starts many years before that.

I was 19. I had used my entire summer earnings to fly to Mexico City for an adventure. The place was intoxicating and exotic, but it wasn’t the street food or the ancient ruins that made the biggest impact on me. It was the way I lived when I was there. It was the freedom I experienced, the people I met, and how I interacted with them. For the first time in my life, I had complete control over where I was and what I was doing.

Years later, when I was sitting in cheap beige cubicles with people who were preoccupied with condos and mortgages and company picnics— when I was dreaming of “travel”— it wasn’t the tacos or the pyramids I missed, it was the freedom. I wanted to own my life.

At the age of 25, sitting in traffic on the way to the office, it seemed a notion so exotic as to almost be impossible.


It’s this perspective, my background in cubicles (and before that in warehouses, and factories, and family style restaurants) and hours long commutes, and the general expectation of decades of more of the same, that keeps me out of the “downsides of digital nomadism” discussion (for the most part). I’m here to build my life around the things I value. That’s the extent of the promise I’d make to anyone— being a digital nomad certainly won’t make you happy, and it might not live up to all the expectations you have for it. It will only give you a platform— time, income, mobility— from which you can decide the rest.

All the talk of “beaches in Thailand won’t make you happy” or that “location independence is a fad” or that “I really just want to find work that I love” are, in my view, all flimsy counter points generated from spoiled generation Yers, corporate apologists, or temporarily temple-fatigued travel bloggers.

It all misses the point— being location independent isn’t the end. It is the beginning.

*  *  *

The Four Hour Work Week showed many of us that it was possible to quit our jobs, automate our businesses, and travel the world. But for me– a guy who needed to make a few bucks and who wasn’t content working my way from adventure to adventure, from menial job to menial job– I needed to hear another message. Here it is:

You can live location independently and build wealth at the same time.

And when I heard it, and believed it, my other options as I saw them– being a perpetually broke bohemian, toiling away in a soulless job for decades to get f*ck you money, or staying the course in those beige cubicles– melted away.

There was a comment a few years ago on one of Tim Ferriss’ book marketing mega-posts. In the post, Tim outlined the tactics he used to become a bestseller, but the commenter reminded him that the most important point went unmentioned– that Tim had, despite a “get rich quick” title, written an outstanding book. One worthy of being a best seller.

That a book so timely would be mentioned as a must read still 7 years after it was published, and almost 9 years after it was written says something about it’s quality, and it also says something about it’s popularity. I’ll mention it again just for good measure— if you haven’t yet read the Four Hour Work Week, you ought to go do so.

I can understand why 4HWW grinds some people’s gears. The writing is so tight and segmented that it reads like a sales letter. And that’s not a bad way to look at it. To date, it is the single most effective sales letter for the location independent movement. I haven’t asked them, but I would not be surprised if 80+% of DCers have read the book. For better or worse, 4HWW is the Bible of the digital nomad movement.

If 4HWW is the Bible– the foundational text– we’ve striven to be the Sunday school worksheets.  Providing guidelines on how concepts from the book look when implemented in the field. We’ve experimented in real life with almost every concept explicitly mentioned in the book— from remote work agreements, outsourcing, remote teams, dream lining and goal setting, mini-retirements and travel, automation, filling the void, and productivity.

We’ve worked to extend and augment the concepts where we can— from niche selectionidea generation heuristics, masterminding, implications of lifestyle designhyper globalized small businessesmini-mogulismbaselining, global teams, and the old school cold-call hustle, among many others.

We have probably been best known for our apprenticeships and job opportunities— so called “lifestyle design jobs.” If you dig through the archives you’ll probably run into 20 or so job offers we’ve created over the years, the template of which have been used by many in our community to build their teams. In my mind, this style of team building is an immediate implication of the core concept of lifestyle design– if business owners want time and mobility freedom so much that they are willing to trade some cash to get it, why would employees be any different?

We’ve worked to distance ourselves from the “intern” or “apprentice” stuff. We’re focused on connecting legit entrepreneurs who’ve made this lifestyle a reality, not handing out jobs, although we certainly intend to continue to use this blog to recruit new team members.

*  *  *

When we started our blog in 2009, we were ‘way too late to the game.’ Everybody had already “figured podcasting out,” or at least figured out that podcasting was no way to make money. (My how things have changed!)

Now, in 2014, we are occasionally referred to as “old guys” or the original gangsters. But, of course, there are always more original gansters. In our case, they were Jeremy and Jason at Internet Business Mastery. Over the course of a 6 month period, I listened to most of their back catalog. I joined their membership. I met Jeremy in person and plied him for advice (thank you Jeremy!) Hell, I even moved to the Philippines because of one episode.

They inspired me to dream of travel and of online success. They proved to me that it was possible. They showed me how it was done— by picking up the mic and sharing your experiences. Or by opening up your laptop and creating new ones.

And the most important one I’ve created to date doesn’t show up on our “popular posts page.”

It’s this one. Sometimes it’s difficult to remember that the most important blog stat– impact— doesn’t show up in Google analytics. In this case, 6 entrepreneurs met the requirements, and would end up being influential in our development. We spent Sunday evenings on the phone together swapping notes, giving tough feedback, and pitching ideas. Every week somebody would get to present a new idea— to sit on the hot seat— and that person, if willing to take the heat, would get gold.

On one of those calls Matt, an insanely intelligent entrepreneur, was busting me up. This is valuable Dan. Do more of this. I’ll pay you for it! Start an official mastermind.

I eventually wised up and took his advice. I threw a mastermind event, and people showed up. Good things have since happened.

Fast forward just a few short years. At the end of October, 100’s of us will be gathering in Bangkok to meet, to show up, and I’m sure, good things will happen.

*  *  *

For me, these articles and podcasts are just smoke signals which vaguely gesture to a fire burning bright in the valley below.

Follow this metaphor for a while— perhaps building a platform of time, income, and mobility isn’t so much a matter of scaling a mountain (We have often stressed the difficulty of building businesses over the years, as if we are all mini-sisyphuses enduring the heat and rolling boulders in an absurd struggle).

What if instead you start on the ridge, surveying the valley below.

Maybe the challenge is in trusting that there really is a fire under those wafting signals. That if you descend the trail you’ll find a camp worth staying in for a while. That being based there might not be so difficult. That you’ll benefit from the support of the others who are on the ground.

Maybe doing the work is the easy part. Perhaps the hard part is giving up your place on that ridge.

From high above the valley you can scan the horizon and spot many different signals— indications of life below and opportunities to be had. You know that once you’ve descended the trail and joined the camp– once you’ve shown up– that the perspective you enjoyed from the high ground might be very hard to reclaim indeed.


Thanks to all of you for a great 5 years.



Thanks to Alex McQuade, Taylor Pearson, and Matt Gelgota for reviewing a draft of this article.


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