What Nobody Told Me About Long-Term Solo Travel


Climbing the limestone karst islands of Ha Long Bay, Vietnam

Before my trip, there were many blogs I read and stories I heard from friends about how to prepare and what to expect for a year of travel by myself. Still, I missed many important warnings and lessons that I had to learn through trial and error and personal experience. Here are the ones I’ve found most crucial during my time abroad:

Not Being a Tourist Takes Discipline

There’s absolutely a difference between travelers and tourists–it’s learning. Tourists seek enjoyment from their visits, and there’s nothing wrong with that. On the other hand, travelers not only want to have fun, but they also seek to learn from the experience. In my mind, that distinction makes for far more tourists than true travelers.

Though I consider myself a traveler, since January I’ve often struggled to be one. Traveling requires a great effort to make yourself uncomfortable in novel surroundings, and it isn’t easy or always instantly gratifying. For example, in religious monuments, I’ve many times quickly snapped photos and walked out, never bothering to educate myself about the significance of the landmark.

In my case, my goal in Asia was (and still is) to better understand extreme poverty and promising solutions to the problem. While I’ve met some inspiring individuals in different countries working to fight poverty, I’ve had little meaningful interaction with poor people and immersion in their lives. Part of that is not having a language in common, though it’s more my unwillingness to abandon a fan and internet in order to see a reality I don’t yet know.

Sometimes You Need a Vacation From Traveling

Since most people don’t ever go abroad for more than a couple weeks at once, the idea of locking yourself in a hotel room near a tropical beach to watch an entire season of “House of Cards” sounds obscene. However, when exhausted from repeated overnight bus rides, wilderness treks, and MSG-laden meals, isolating yourself in an air-conditioned environment with fast wifi can be exactly what you need.

At first I felt guilty for taking daylong breaks from intense traveling, but now I’ve just embraced my downtime to catch up with friends and use my laptop. However, I have the tendency to take this relaxation too far and become complacent in a place where I’ve gotten comfortable. That was exactly what I ended up doing for three weeks in Chiang Mai, Thailand, which is perhaps the world’s easiest place to live as an expat. Fortunately, by now I’ve discovered the remedy to my laziness is to book imminent buses or flights to my next destination, effectively setting an end date to my complacency.


In Southeast Asia, there are three things you find almost everywhere–temples, waterfalls, and caves. It’s hard to become exuberant at the prospect of seeing another gilded Buddha statue when you’ve seen five in the past week.

Simply, my interest wanes progressively each time I’m presented with an experience that’s mostly indistinguishable from the last one of its type. I have to be careful to not come off as jaded to other awe-struck travelers who are enjoying short vacations or who are in completely new environments.

The flip side of this phenomenon is that I desire superlative experiences and just skip what’s mediocre. As such, having those one-of-a-kind experiences can be more expensive and arduous, but they end up being much more memorable.

At the same time, I seek out the less apparent characteristics that make a place great. Recently, I’d much rather wander into a bustling, gritty market to find the special dish served at every stall than visit a waterfall with a flock of Australians.

Never-ending Research

Before I became a nomad, I enjoyed researching upcoming short trips because I could feel some of the excitement of the destination before I got there. Now I can hardly go a day without spending at least 30 minutes on Lonely Planet and Agoda as I annoy friends familiar with the places I’m going for tips. Planning trip logistics is tedious, but the real downside is it can prevent me from fully enjoying where I am today when I have to already think about tomorrow’s bus schedules and visa requirements.

Hidden Costs

Given my maximum monthly budget of $1,500 (including all expenses such as food, accommodation, transportation, insurance, etc.), every little expense counts. And, it turns out there are many inevitable costs while traveling that I never planned to pay.

Water: I’ve always taken for granted the convenience of being able to safely drink tap water at home. In much of Asia, that’s not the case, so I’ve resorted to buying bottled water. Since I need about 5 liters per day, especially when out in 100-degree humid sun, the $0.25-$0.50 per 1.5-liter bottle adds up to over $50 monthly for me. Of course, I gladly take any opportunity to refill my bottles when I can at guesthouses and street food stalls, but, depending on the country, that isn’t always available.

Corruption: The sad curse of poor countries is that bribery and corruption are the norm, and foreigners are easy targets. Particularly if you’re motorcycling long-distance in these places, as I did in Vietnam, expect to pay $5-25 every time you’re stopped. If the enforcing authorities manage to successfully communicate to you, reasons for paying your “fine” include not having a proper motorcycle license and using your headlights during the day, among other creative infractions. Immigration and border crossings are also moments when travelers are vulnerable, and sometimes it’s not worth fighting, as someone I know battled over a few dollars at the Laos-Cambodia border.

Theft, loss, and damage: The longer and more intrepidly you travel, the likelier you’ll eventually have your purse strap slashed, your phone screen shattered, or your camera waterlogged. Even just last week, my newly-purchased phone was ripped out of my hands by a thief on the back of a passing motorbike in Phnom Penh. To hedge against this, I always buy cheap (but good enough) electronics because I have the propensity to go through four phones per year between clumsiness, forgetfulness, and unawareness.

Medical costs: Some health insurance policies might cover you while abroad, but it’s probably still a good idea to buy a separate travel insurance policy. Over a year of travel, it’s reasonable to have to see a doctor a few times. For severe incidents not covered by your primary insurance, travel insurance can save you thousands of dollars. At $80 monthly, I’ve been happy with World Nomads insurance, which comes highly recommended.

It Gets Lonely, But That’s Okay

To be fair, before I started my trip many people at least implied the loneliness I’d feel traveling by myself for so long. As the headstrong person I am, I mostly ignored their objection to my solo journey. But, they were right, just probably not in the way they intended.

So far in the six countries I’ve visited during over four months, I’ve met countless people and am hardly ever not surrounded by a mass of humanity. Moreover, I use Couchsurfing (both to find hosts and meet locals), practice new words with the women selling me curry at the market, and muse about cultural differences to other travelers. In the sense of solitude, I’m hardly ever lonely.

The real loneliness comes from not being with those who care about what I care about and possess the traits I admire. I’m now at the point that I’ve had enough meaningless small talk with backpackers who’s first question is, “So, where are you from?” followed by, “How ’bout a beer, mate?” As such, I actively avoid hostels and places frequented by other backpackers.

Luckily, my saving grace has been constant contact online with like-minded friends who motivate me to be better. Still, I lack much fulfilling in-person interaction, but besides the prospect of my close friends coming to travel with me, I accept my situation until I make somewhere home.

In the meantime, I’m better understanding my default behavior when I’m not around anyone I know. Realizing how I feel and how I act is paramount for succeeding and being happy at whatever I do next. Hence, I’m grateful because there’s no better way I could’ve learned that than wandering by myself.


What a Blind Masseur, Elder Crossbow Maker, and Deaf Server Taught Me About Competitive Advantage


Photo: Hue Lee

I remember the collective cringing and suppressed giggling in my seventh grade Spanish classroom when we learned our textbook’s word for “disabled”–minusválido. All it took was using the two English cognates within the word to literally translate the meaning as “less valid.” It was so blatantly un-PC that I almost preferred to miss the points on a pop quiz than to answer correctly.

I’m ashamed to admit my middle school reaction to the presence or mere topic of disability continues well into adulthood. Whenever I see someone with Down syndrome or amputated limbs, I tense up. I don’t know if I should look away or engage them while pretending they have no handicap.

“Don’t stare! If Mom taught you anything, it’s that you shouldn’t stare,” I’d command myself. I then become consumed by the intention to do what’s inoffensive, or at least doesn’t portray me as an atrocious excuse for a human being.

Like so many others who’ve never had meaningful personal experiences with disability, I’m stuck in the mindset of pity. We view mental and physical disability, often in conjunction with age, as a disadvantage compared to the rest of society. To me, even advocacy and assistance programs for disabled people seem rooted in a dynamic of inferiority, regardless of how much they harp on “empowerment.”

If the goal is to raise the status of disabled people, then isn’t assuming a best case scenario that’s merely palliative actually just perpetuating inequality? I’m talking about the charities donating electric wheelchairs to veterans and the organizations whose ultimate mission is for autistic people to live away from their families.

Overall we seem more concerned with finding new, more sensitive vocabulary than changing the reality of disability. Is that the best we can do?

Having a Blast with Master Chaisong

Until I visited Asia, I didn’t recognize any viable solutions. Sadly I figured many of the world’s disabled, discarded, and devalued people were doomed to remain unproductive drains on the rest of society.

To change my outlook I needed to first tire of the touristy activities offered in the otherwise quaint riverside town of Luang Prabang, Laos. Incapable of witnessing one more stack of elephant pants on sale at the night market, my research led me to the upstart Backstreet Academy.

Through a slick online marketplace, the company provides short lessons in traditional skills (including rice farming, hat making, and knife crafting) led by local instructor-tradespeople across Asia. Furthermore, the teachers are usually low-income and marginalized in their own countries.

All of Backstreet Academy’s unique offerings intrigued me, but the little kid inside of me jumped at the chance to make and shoot an authentic Hmong wooden crossbow. What’s more, the $25 price for a four-hour private session facilitated by a translator was unbeatable.

Best of all, I was getting one-on-one instruction from 84-year-old Chaisong, a Hmong master crossbow craftsman, in his village workshop. He guided me in whittling bamboo, puncturing precise holes with a fire-heated metal rod, and, of course, proper crossbow archery form. From Chaisong I learned not only about ancient weapon building but also daily life, family, and politics in Laos. In the meantime, I had the most fun in over two weeks there.

As an elderly man of a minority ethnic group, he had little opportunity, yet in this case he was making significant income for his family while Backstreet Academy generated revenue for itself.

More importantly, as a customer, I had a fantastic experience because of Chaisong’s age and minority background, not in spite of those characteristics which we typically deem disadvantages. It was due to Chaisong’s accumulated knowledge in a non-mainstream craft that I enjoyed myself.

From Econ 101, I recognized this as an example of a ubiquitous phenomenon that drives our work and buying decisions every day. Called competitive advantage, the concept predicts that businesses with superior attributes, such as new technology, highly-skilled labor, and access to natural resources, will beat their rivals.

Given its 97.6% TripAdvisor recommendation rate along with rapid expansion into new destinations, certainly Backstreet Academy’s activity offerings have a competitive advantage.

Once I realized how “disadvantaged” personnel actually could give a commercial advantage over other businesses, I began seeking them out in the rest of Asia.

Next, I visited a popular massage shop in Chiang Mai, Thailand with exclusively blind masseurs. Studies show that other senses, in this instance touch, are heightened when one sense is lost. As a result, I got one of the most relaxing massages of my life.

Later, in the bustling historic town of Hoi An, Vietnam, I found respite from busy walking streets inside Reaching Out Tea House. Staffed by hearing-impaired servers, the cafe requires patrons to silently communicate orders using labeled wooden blocks and writing. I soon melted into the room’s quiet serenity, which I was grateful for after days of intense traveling. Again, it was a disability that worked as an advantage to make me so satisfied; and considering Reaching Out is rated #1 of nearly 500 restaurants in Hoi An, I wasn’t the only happy customer.

Using Profit to Change Minds and Restore Dignity

In over four months traveling through Asia, I’ve seen countless examples of businesses utilizing disability and marginalization as a competitive advantage. Back in the US as well there are similar organizations profiting from people’s differing strengths, such as a car wash with autistic employees, while adding thousands of jobs.

Consequently, we should ask ourselves why this principle remains on the fringe even though disabled and marginalized people are powering businesses all over. Unfortunately, we’re limited by our obsolete beliefs. If we think that disabilities aren’t suited to employment, then no one ever tries to disprove that fallacy.

We need more businesses serving as role models and risk-taking entrepreneurs willing to shatter misconceptions. Charity and sensitivity training are well-intentioned, but they aren’t solving the root of the problem–we don’t appreciate all people’s differing competitive advantages.

Now pure, self-interested capitalism is the only force that can shift us from pity to profit. Then, we can spark a reconsideration of the importance intrinsic to all humanity.


What Happens When You Shut Down Southeast Asia’s Longest Tunnel

The ventilation fans roared as I tried to calculate how far inside the mountain I was. “What if they caught Saeid?,” I worried. But anxiety was pointless–I had to focus on squeezing my motorbike between the one lane of trucks and the wall.

There I was, the target of a high-speed chase, somewhere deep within Southeast Asia’s longest tunnel, revving a $275 fast-falling-apart motor scooter to its limits. In that moment, instinct overcame any shred of reason left me. After that and only now can I now empathize with the “bad guys” in Cops, whose televised attempts to flee always seemed so futile.

To get to that point took merely the three preceding minutes, but the lead-up to motorbiking the length of Vietnam with my friend Saeid set the stage. Throughout our trip preparation, we heard tales of corrupt authorities extracting bribes from defenseless foreigners. Having lived in neighboring Laos for over a year, Saeid had more experience with such nuisances, but even I surprisingly faced some greedy officers in more-developed Thailand a couple weeks prior.

Still, the most colorful stories came from the hyperbolic Iranian bike shop owner in Hanoi who sold us our motorbikes. He claimed he’d always take a hard-line stance when dealing with shakedowns. In particular, I’ll forever be able to mentally replay the dialogue he recalled to us from one of those run-ins, including the gem: “You touch my bike, I break your face!”

However, his recommendations of specific tactics to ensure the best outcome for ourselves didn’t instill confidence in me. Removing and hiding the keys to our bikes seemed risky, and the idea of speaking gibberish to both the officers and each other was absurd. Nonetheless, the overall message was clear–don’t take the authorities’ opportunistic behavior seriously, and if forced to pay a bribe, remember the amount is negotiable, just like seemingly everything else in the country.

As we drove south from Hanoi over the week, my pulse spiked every time we passed a toll or anywhere authorities could be present. Nearing Vietnam’s middle point of Da Nang, I was surprised that we’d driven nearly 1,000 km without even a close call, but that would all change near the outer limits of the city.

During what would total eight hours of arduous motorcycle riding to our destination, we reached the Hải Vân Tunnel, the longest in Southeast Asia. Diligently following our Google Maps directions, we began climbing the ramp to enter the four-mile tunnel.

Just as the ramp sloped upward, a transit officer appeared from the roadside frantically waving a traffic wand. Though I figured his signaling was directed at me, it would’ve been dangerous to stop on the narrow, fast-moving road. More importantly, I didn’t see anything wrong as we were keeping up with the speed of traffic and had our helmets on. My instant judgement was that the officer had nefarious intentions, so I pressed forward.

Halfway up the ramp Saeid​ reached my speed alongside me, and I yelled over the engine noise that it seemed the officer wanted us to stop. Saeid laughed at how blatantly we cruised past the officer, and I drove ahead of Saeid to the tunnel entrance.

Then, about 200 feet before me was another officer also waving us down, making me even more anxious about what I feared was organized extortion. With a jolt to the amygdala, my flight instinct kicked in, and I “floored” the gas on my ailing Suzuki Sapphire into the eerie mountain tunnel.

Once I started to control myself, I was determined to outmaneuver detection and reach freedom on the other end, unaware of how far away it was. Consequently, my strategy was riding along the five-foot shoulder gap between the large trucks and tunnel wall. If necessary, I could closely trail big trucks to hide myself. Following this plan, two miles deep into the mountain without any signs of pursuers, I became more confident I’d exit without issues.

Abruptly, flashing lights and shouting from ahead startled me as the truck in front of me in our lane came to a halt. A large van coming from the opposite direction screeched to a horizontal stop, blocking both directions of the tunnel. Neon reflective men descended from the vehicle waving their arms and blowing whistles, forcefully gesturing at me to move my bike against the wall while they efficiently redirected traffic around me.

I was in big trouble. Then, a few seconds later Saeid cautiously pulled up behind me along with more officers. Actually, we were in big trouble.

I reflexively removed the key from the ignition and pocketed it, shaking from my imagination of what would happen next. Would they take our bikes away, shove us in the van, and lock us in some decrepit holding cell? In the process would they take our money and beat us until we let them extract everything from our bank accounts at an ATM?

As furious as these officers were, I couldn’t help but get the feeling this was the most excitement they’d had in a long time. From the fervor of their gesticulation and flawless rerouting of vehicles, it seemed they were finally enacting the emergency tunnel shutdown plan that they’d drilled countless times before.

One of the men strutted up to us and irately lectured us in Vietnamese. I stole a glance over my shoulder at Saeid, and it was abundantly clear from the man’s repetition of “No moto! No moto!” what we’d done wrong. A double-decker Chinese tour bus slowly rolled past in the oncoming lane as passengers got out of their seats to gawk at the captured fugitives.

Following ten minutes of seated observation of the officers diligently restoring traffic flow, they motioned for us to start our bikes so they could escort us back to the side from which we entered. I was surprised we weren’t yet detained, but their request was reasonable since they otherwise couldn’t have removed our bikes from the road. Ultimately, our strange death march motorcade ended on a tarmac just outside of the tunnel entrance where we got off our bikes while surrounded by four officers.

After more incomprehensible berating by an officer pointing to the small sign at the entrance depicting a crossed-out motorcycle, Saeid and I independently acted in unison on past advice to communicate neither in English nor Vietnamese. Saeid was defending himself in Farsi while I did my best to mimic him while pointing and shrugging at the Google Maps directions on my phone.

As we weren’t reaching a resolution by playing dumb to the officer’s insistence on the visibility of the road sign, another officer impatiently cut to the chase: “Mo-ney,” he said with his hand out. In hindsight, it’s shocking we didn’t hear that word, perhaps the only English word known by half the world, earlier in the interaction.

In a split second, the officers’ impressive coordination that we’d witnessed previously seemingly disintegrated. Just before the irate officer could process what his colleague had just uttered, he would go on to waste a big payday for himself and the others.

Now, a disclaimer: I should warn that the rest of this account is so comically absurd that it’s unbelievable, and Saeid and I still haven’t deciphered what happened or why it happened.

At that instant, the particularly animated officer began making obscene sexual gestures with his hands, which were soon followed by the other officers who together kept exclaiming, “Vietnam! Vietnam!” Patently confused by this least expected change of the officers’ behavior, Saeid and I burst out in laughter.

The initiating officer’s lewdness escalated to motioning at Saeid’s crotch and then lifting one of his own legs under the knee while hopping on the other leg as he thrust his arm beneath his knee. I’d witnessed many such depraved gestures in my lifetime, but this one was superior in its creativity and lewdness.

The officer then stopped his twisted game of one-legged hopscotch and actually lunged for and grabbed Saeid’s groin. Saeid flinched to cover himself, and the officer quickly let go. There was nothing else we could do besdes nervously join the officers’ chorus of cackles.

Suddenly and bewilderingly, the circumstances had changed, and I was certain nothing bad could happen, even if the preceding moments made it seem we would’ve at least had to pay bribes.

Maybe pushing our luck, in true tourist fashion Saeid then took out his phone to snap a group selfie photo, but all of the officers smartly declined except this one (whose face I’ve removed for his job security):

Credit: Saeid Kian

Credit: Saeid Kian

Finally, the officers relented, waving us off to drive in the dark over the mountain pass route above the tunnel that we were always meant to take.

And that, my friends, is the legend of how I closed the longest tunnel in SE Asia and my friend’s tight shorts saved my life, or at least my wallet. If there’s some wisdom to be learned from this saga, I haven’t found it. Instead, sometimes there are experiences that won’t produce “6 Things I Learned from” articles. This was certainly one of those times, and I hope to have many more.


Bullets vs. Big Macs: Why You’re Killing Yourself by Playing It Safe

By Tomas Castelazo (Own work) [CC BY-SA 3.0 or GFDL], via Wikimedia Commons

By Geoffrey Fairchild (Own work) [CC BY-SA 3.0 or GFDL], via Flickr

Four handguns and a semiautomatic pointed at my skull. The stench of raw sewage stung my sinuses while 105-degree sunbeams pierced the cracks in the hillside cinder-block labyrinth. My joints locked up, and I sucked in one shallow gasp as my brain went to mush.

It was December 21, 2012–the day the world was supposed to end. In the week before, I paid scant attention to the sardonic “Mayan Apocalypse Party” Facebook invitations; but for the longest 20 seconds I’ve ever known, I sensed my world would end then and there in Brazil’s biggest favela.

The shouted Portuguese commands didn’t consciously register with me, and whatever verbal and bodily responses I mustered were automatic. I peeled my sweat-soaked jersey above my stomach to reveal my empty waistband, and the blur of men behind the guns realized I was just an unarmed gringo. That’s all that mattered, and strangely they lowered their weapons, profusely apologizing as we parted in separate directions.

In fact I was hardly ever in any real danger despite the drama, which was entirely due to my ignorance. I had merely lost my way in Rocinha’s criss-crossed paths near my new apartment, leaving me looking confused and pacing back and forth. I later discovered my unusual behavior and out-of-place, stubbly, white guy appearance embodied the drug traffickers’ conception of an undercover cop.

More importantly, that harrowing experience gave me reason to stay and work against the systemic marginalization that fuels the existence of such drug gangs in favelas. After nearly a year and half living in Rocinha, I know I wasn’t much risking my life. I’m confident that I, like all foreigners with common sense, was in far less danger inside the favela than in tourist neighborhoods of Rio.

Nevertheless, my friends, family, and university emphasized more the grave risk in my post-graduation career choice. Not only was I straying from the trodden path of my peers to Wall Street, consulting, and the Fortune 500, I was not even pursuing any job or subsequent degree. Worse was that I was starting a scary business in a scary place with no real experience to guide me. Without a doubt, compared to the accepted model I was a freak. In society’s eyes, if I could dodge the gunshots, how would I ever make enough money to survive?

Ultimately, there was no Favela Experience IPO, yet I (and my customers) left without a scratch, and I earned enough to live off of for two years. Beyond that, I felt the unique fulfillment of running my own business, one that satisfied my customers while generating significant income for disadvantaged favela families. Even if I can’t innumerate a list of pithy business lessons from my experience, most valuable of all, I learned a great deal about myself and what I need to thrive. I won control of my present and my future, and as hard as it could be at times, I began truly living.

Looking back, the perceived big risk I took wasn’t so risky at all. I had little money to lose or commitments to harm. At the least, I stood to gain self-awareness and grit from the unpredictability and challenge of entirely new life experiences.

On the other hand, it was actually the traditional and dogmatically-presented “safe” path that was terribly risky for me. I can’t refute that by working 80+ hours weekly to “maximize value” for faceless clients I could boost my hypothetical, initial high-five-figure salary to mid-six by age 27. Nor can I deny I could go on to a prestigious MBA plus $150k in debt to next slave toward the arduous partner/VP track. By my 40s I’d probably become quite wealthy, albeit pressured to maintain an exorbitant lifestyle in order to maintain my social and professional circles.

Still, what was suspiciously absent from that senior year calculation of potential career options was everything but wealth. I’m grateful I had the foresight to recognize the likely health and spiritual costs of following convention. I simply would’ve hated that kind of work and probably wouldn’t have been very good at it.

Whether scarfing down artery-clogging fast food meals at my desk so I could meet urgent deadlines or awaking to dread another day of a tiring routine at a company I don’t care about, I’d be forgoing well-being and self-actualization for financial security and social conformity.

What’s so special about safety, anyways? At its core, seeking safety is one of our two possible responses to our fear of an unknown future. The other is embracing uncertainty.

By seeking safety, our rewards are necessarily bound by what’s socially desirable: income, status, and appearance. At best, the cult of safety bestows incrementally better lives, in the material sense, upon its devotees who are left wondering, “What if?”

Alternatively, by embracing uncertainty, we seek the painful challenges that force us to try and fail, to open ourselves to new beliefs, and to finally grow beyond the lives we’re told to live.

Applying these attitudes to the real world two years out of college, I’m dismayed to see the safety fallacy gripping friends and former classmates who have incredible potential. I can’t think of a single person who took a finance or consulting job who doesn’t lament significant elements of their work, including the meaningfulness of the role, the mindset of their colleagues, and the lifestyle of their profession.

Nonetheless, these people rationalize their dissatisfaction as a few brief years of “paying their dues” to get promoted, earn higher salaries, and do more important work. In particular, I worry for those aspiring entrepreneurs who are waiting for the right moment. The longer they wait only accumulate more personal commitments (relationships, children, and debt) and increasingly accustom themselves to lavish habits. They say they’re “saving up to quit,” but they struggle to state concrete sums needed to do so.

In my case, I know every day rejecting safety further excludes me from ever returning to safety. It only took a few guns pointed at my head to accept that challenging path, but I know the rewards will be exponential from here forward.


How a Guy in Underpants Got into The New York Times, The Wall Street Journal, and CNN

“How did you do it?”

I’ve been asked that question many times since starting Favela Experience in reference to how the business earned such widespread press coverage. In the eyes of many, our features in Forbes, The New York Times, CNN, The Wall Street Journal, and other international media outlets were our greatest point of success.

Most importantly, this achievement didn’t take any magic, special connections, or spending money. To the contrary, I even coordinated this press and gave Skype interviews from my dungeon-like favela apartment often without putting on pants. If I can do it, so can you.

In comparison to my early desperation for PR (so much so that I did this), by the end of the FIFA World Cup I’d learned a great deal about getting media coverage. The key is straightforward but not easy, and if I could distill it in two words, it’s this:

Be newsworthy.

That might sound as us unhelpful as telling a short person to be tall; yet, newsworthiness consists of two important parts, that when combined, are potent bait for journalists. Nonetheless, to truly understand what subjects the media will report on requires empathizing with the people who run the news business. And “Business” is the operative word because if you don’t recognize the profit motive behind media organizations, then you’ll be forever mystified about why TechCrunch isn’t begging for quotes on your new “way better than Tinder” dating app.

You already know this, but media organizations mostly make their money from advertising revenue. Moreover, advertisers show their ads on blogs, TV, and newspapers because they expect the ads will make them a lot more money than the cost of the ads. In order for them to profit, advertisers typically need as many media viewers as possible to see or hear their ads.

No matter how effective the ad, if media outlets have too few viewers or listeners, then advertisers won’t even consider spending their advertising budgets with those media companies.

Be (Strongly) Emotional

Now, how do media companies (especially those intended for mass audiences) get us to read, watch, and listen? It’s simple: they appeal to our emotions. Not just any emotions–fear, lust, disgust, and intrigue are all some of the strongest ones. Journalists know this, so they’re deliberate in choosing emotional stories.

Look at the most-viewed articles on any mainstream news site, and from the headlines alone you’ll likely be able to pinpoint at least one of those emotions summoning you to click. In its most blatant form, the “sweeps week” phenomenon, by which otherwise-orthodox media covers particularly salacious stories, shows how powerful emotions drive the news.

For Favela Experience, the newsworthy emotions elicited by press pieces about us were fear and disgust. First, stereotypes about drugs and violence in favelas cause the public to (undeservedly) fear favelas, and the idea of unsuspecting tourists staying in favela homes only exacerbates this fright. Furthermore, hyperbolic representations of favelas as “squalid slums” provokes hygienic disgust, and presumptions about a rich kid from Beverly Hills taking advantage or poor favela host families induce moral outrage.

Of course, I wish I could say we were so successful with PR because our story incited fascination and inspiration, but I know it was mostly the negative emotions that led reporters to eventually beg me for interviews. If you’re unsure of that, then next time you turn on the nightly news, notice how most stories focus on disaster, war, crime, and scandal, rather than humanitarianism, peace, selfless acts, and societal advancements.

Ultimately, I encourage those aspiring for PR to make themselves controversial, as long as you’re okay with the press and public demonizing you (as was what happened to me). Breaking social norms and pissing off people (especially the ones whose opinions don’t matter to you) is an excellent tactic to get into the news.

Be Relevant

The other component of newsworthiness is relevance to context. The media cover certain themes at certain times, so fitting one of those themes and then “being in the right place at the right time” can make your story worthwhile.

In the case of Favela Experience, our story was always strongly emotional, but it wasn’t relevant to the mainstream until the public began to think about the World Cup. That didn’t happen until about six months before the tournament, particularly around the Dec. 6, 2013 draw event determining which teams would play in which host cities. Fittingly, the media only really began to approach me then, their requests reaching a fever pitch in May and June of last year. As incredible as it would’ve been to me before, at that point I actually had to turn away many journalists.

Also important to realize is that the World Cup is a recurring event (every four years) with a pretty predictable media coverage timeline. PR seekers can look at other similarly recurring events to determine when their stories will be most relevant.

How Will the Media Find Me?

Prior to getting lucky, I tried different tactics with journalists to varying degrees of success. Had I never sought out press, the media still probably would’ve found me based on the fact that Favela Experience had a searchable web presence, and the journalists knew people who would’ve referred them to me. Regardless, I still advocate “pitching” journalists because this can speed up the process, even though I don’t have specific recommendations on how to do so.

I attempted cold calls, emails, and Tweets in addition to warm introductions (by searching LinkedIn for who had connections at my target media outlets), but since no single method worked better than the others, I suggest experimenting with all of them. To illustrate the unique paths that led to PR, I’m summarizing the chain of events for some of our notable press features:

LAN (the Latin American airline) blog – While LAN’s blog doesn’t have an immense readership, this piece is worth mentioning because it was the only press we paid for, splitting with our partner Favela Adventures the ~$300 cost of comping the writer’s flight, transportation, accommodation, activities, and food. After a friend told me about him, I cold emailed this journalist because he’s also one of the writers of the Lonely Planet travel guide for Brazil. Forgetting he never replied, I saw he Tweeted an article from Rio’s English news site (coincidentally written by one our customers) that mentioned us. I immediately Tweeted back, and shortly thereafter we arranged a weekend-long visit. An added bonus was that the writer later recommended us in Lonely Planet’s 2014 World Cup guide.

Forbes  I read a Forbes profile about my former employer and noticed the writer’s (actually a contributor–see the section below) beat included for-profit social enterprise, so I figured I’d pitch her. I found her personal website listing her cell number and then called and left a voice message. She quickly returned my call but seemed rushed and disinterested, asking that I follow-up with her by email. I did, but only a week later did she respond asking for a Skype interview. The interview was over an hour, but she quickly published the article entirely about me and my business.

The New York Times video and article  Before I moved to Brazil, a mentor introduced me to a journalist friend living in Rio whom I met shortly after arriving in Brazil to run Favela Experience full-time. That woman told me to contact a fixer (a sort of liaison) for international journalists in the country, but that particular fixer didn’t contact me until many months later. At that point working with The New York Times, she contacted me to arrange an in-person visit by an entire multimedia crew.

CNN article – Though I don’t remember if they’d found us from The New York Times pieces, they emailed me to write an article and shoot video. After this was published, many other international media outlets contacted me citing CNN’s coverage, showing how one feature can spiral into many.

The Wall Street Journal video – Without me seeking them out, journalists and producers from The Wall Street Journal arranged an in-person interview for a video piece shortly before the World Cup.

A Shortcut to Forbes and The Huffington Post–”The Contributor Network”

If you want PR for the purpose of credibility (but aren’t so concerned with mass awareness), then consider pitching Forbes and The Huffington Post. Both of these along with other sites’ business models leverage “contributor networks,” legions of writers often without journalism backgrounds who end up writing for free or close to it. These denominated contributors are separate from the regularly paid staff journalists and freelancers whose work is generally more prominently displayed in the publication. Alongside the article author’s name, you can usually see if he or she is a contributor.

If you didn’t realize that crucial difference in author classification last time you read Forbes, then you’re like 99% of the population. At least for now, you can use this general ignorance to your advantage!

I estimate there are over 10 times as many contributors as paid staff, and you’d be surprised at how unremarkable you have to be to be a contributor for Forbes or HuffPo. After hearing horror stories from a friend who works at Forbes and seeing some embarrassingly bad pieces in HuffPo, I know the bar is low to become a contributor.

Most important is that, in general, you can far more easily get a positive response from a contributor than a staff journalist. When pitching, just remember the motivations of contributors might not match staff–they could be out for self-promotion or résumé padding.

Nevertheless, when the article is published, you’ll still get to brag to everyone, at least the ignorant 99%, that you were featured in Forbes, The Huffington Post, or any other of the myriad publications that use contributor networks.


That Time I Made an English App for Brazilian Prostitutes

By Tomas Castelazo (Own work) [CC BY-SA 3.0 or GFDL], via Wikimedia Commons

By Tomas Castelazo (Own work) [CC BY-SA 3.0 or GFDL], via Wikimedia Commons

NOTE: This post itself is rated PG, but the Android app is NSFW.

A Jackson Pollock-esque drizzle of syrup and bacon crumbs trickled down *Lorenzo’s t-shirt as “Living in America” blared on repeat over the house speakers. He stood stooped over an overflowing plate held inches from his face, his basketball shorts’ pockets inexplicably hung inside-out. At 4:00 am I had no right to question him because my appearance wasn’t any more polished than his after another night of user testing.

In retrospect it’s darkly poetic that the best all-you-can-eat American breakfast buffet in Rio de Janeiro is in a brothel, a sexual buffet of sorts. Lorenzo gazed impatiently down at the metal serving tray, neurotically opening and closing the lid in hopes it would magically replenish itself with Eggs Benedict. And I too was almost as determined to get my 14 reals worth of arterial congestion. Even amid that dystopia of lust and gluttony, there was a faint glimmer of compassion in how perhaps as consolation to the women having slow nights, they’d always eat for free.

Only during those twilight hours before the sun broke over Copacabana, between steaming stacks of pancakes and sausages, the weary prostitutes would seem to let their guard down. Sometimes we’d dine next to the women on bar stools, our silent chewing intermittently interrupted by occasional slurps of orange juice. Other times, in an ironic role reversal, Lorenzo and I were still attempting to sell them on our app and explaining its benefits.

Breaking the Taboo

It became an unlikely weekend routine for us, two broke foreign entrepreneurs each running our separate businesses the rest of the time. Lorenzo would endearingly refer to the beachfront blocks below his Manhattan-priced studio apartment as “‘Stoot Row,” and whenever he’d GChat me “stoots tonight,” I’d know my evening plans.

After keeping it to ourselves for so long, the story of how Língua Boa came to be had to be told. It wasn’t as if Lorenzo and I were lifelong friends. We only really knew each other by being gringos trying to accomplish something against the tide of Brazil’s horrendous business climate.

However, our paths to the country were quite different. Having cultivated a passion for Brazil from various visits, I flew to Rio on a one-way ticket two weeks after college graduation to grow my alternative travel venture Favela Experience. On the other hand, when given the opportunity to create the Brazilian software sister company of his dad’s hardware startup, Lorenzo moved knowing merely a few words of Portuguese. Yet, what we most had in common was an aspiration toward greater opportunity for marginalized Brazilians–Lorenzo via quality education from affordable technology and I via increased income for favela families from community-empowered tourism.

One of our first times together was in the fall of 2013 alongside his dad who was visiting for meetings. The conversation fittingly drifted to the looming Copa do Mundo. Lorenzo asked, **”Did you hear about this story with the prostitutes in Belo Horizonte getting English classes for the World Cup?”

Of course I had. After all, my business depended on the FIFA tournament to the point of me maniacally refreshing my Google News feed. That piece of news had recently been the top-trending article on CNN because, well, what’s better click-bait than the stereotyped sensuality of Brazilians and futebol? Disregarding its salaciousness, the report’s context was pertinent–the country’s English fluency rate was miserable. More urgent was that 600 thousand inebriated, predominately male fans from around the globe were set to arrive in less than a year; and contrary to popular belief, no, you really can’t get by on Spanish in Brazil.

Lorenzo nonchalantly continued: “On the side, I started messing around with making an app to teach English to Brazilian prostitutes.”

I was incredulous. Sure, Lorenzo was hardly a buttoned-down guy, but he and his business were publicly visible. Despite that buying and selling sex are both legal (with restrictions) in Brazil, why tarnish your personal and professional reputation associating with such a polarizing industry? Moreover, Lorenzo had to focus on far more important things, like maneuvering government bureaucracy for his business and making rent.

Still, the concept behind the app was intriguing. Of course, he wasn’t imagining its users delivering doctoral thesis defenses, or even having substantial conversation in their new second language.

Instead, he explained, “There’s this Tim Ferriss blog post about how the 100 most common words in English are used half the time.” That meant that hypothetically that a language learner could very quickly begin to communicate with little study. Applying that thinking made sense, and I saw how this was just another example of the 80-20 rule in action.

On top of that, Lorenzo’s dad added that he founded an NGO in developing countries to employ the poor at business process outsourcing centers. Though the workers don’t learn to converse in English, they’re trained in just the technical lexicon needed to be effective at their jobs.

We were still talking about prostitutes, though, so I laughed off the absurdity of Lorenzo’s excitement over something so taboo. Now I see how hypocritical I was as someone working to change the perception of favela residents, another heavily stigmatized group. Specifically, my prejudice stopped me from recognizing that anyone should have access to learn anything, especially if that thing can improve quality of life.

Shameless Opportunism

Around that same time I was consumed by generating awareness of my fledgling community homestay operation in time for a pre-World-Cup crowdfunding campaign. I was studying SEO and realized how much links from reputable sites would advance my internet marketing efforts. Online PR from respected publications could not only convince customers concerned with safety and legitimacy but also boost Favela Experience’s Google rankings. Yet when the traditional route of cold Tweets to journalists was failing, my desperation made me more drastic.

A month after not discussing or even contemplating Lorenzo’s far-fetched idea, we were loitering outside of an Ipanema bar while commiserating about our business problems. A mass of giddy hostelers overflowed into the street before us, foreshadowing a gringo surge magnitudes greater the coming summer for 2014’s FIFA tournament. Suddenly, a wave of brilliance overwhelmed me.

Lorenzo’s app wasn’t so ridiculous after all!

I proclaimed, “We’re going to build the prostitutes app together. It’s sex, soccer, Brazil, and technology all in one. It’ll be too good for the press to resist. And they’ll have to at least add links to my business when they talk about who made the app. Favela Experience will be number one on Google. I’m a genius!”

But, we had to take this seriously. There’d be no half-assing. I was so intent on employing the Lean Startup method that it would’ve made even Eric Ries himself cringe. Before writing a line of code, we were going to get ample, structured feedback on the idea from prostitutes and adjust accordingly. We couldn’t spend a lot of time building something that no one wanted to use. After all, what if prostitutes didn’t even have smartphones? (It turns out they almost all had at least simple Android devices, even a year and a half ago.)

There was one glaring problem. As I was already familiar with strangers’ attacks on the ethics of my controversial business, I worried how the media would portray us. They could paint us as greedy, unscrupulous American male techno-pimps exploiting vulnerable women for profit (even though we never wanted or tried to make any money directly from the app). At the very minimum, they could claim we were contributing to an “immoral” trade.

Our dilemma was that we figured sex workers would only download the app if they thought they’d earn more money through better communication and negotiation with foreigners. For many people that premise in and of itself was reprehensible. So, I proposed we hedge our bets by sneakily incorporating features that could enhance prostitutes’ health and safety outcomes. However, striking the right balance would be tricky. We couldn’t be overbearing and risk deterring users; but the social good component had to be prominent enough that we could reasonably defend ourselves.

Separately, I realize in hindsight I was abruptly asserting part ownership of Lorenzo’s app without even asking. I may have been taking away this cathartic release from the stress of his job. I’m now embarrassed that I was too impressed with myself to care. Fortunately, Lorenzo is so agreeable that it didn’t matter, and he seemed excited that I’d be helping.

Paying to Not Have Sex

One Friday night shortly thereafter my declaration, rough work weeks behind us, we descended Lorenzo’s apartment to begin our research. I was nervous since I’d never actually been inside a brothel, nor even knowingly talked to a prostitute before. We already understood generally where sex workers congregated; however, I was shocked how out in the open it all was, particularly in side street nooks adjacent to five-star hotels like the iconic Copacabana Palace. Having frequently passed through this prime tourism area in daylight, I never noticed any of these seedy establishments.

What made me especially uncomfortable was the men in dark suits on street corners who’d accost us to promote certain brothels and bars. They were seemingly agents guiding potential customers to different establishments, possibly for a commission.

We let one man lead us into a tight alleyway where he opened a door to a musty room full of women standing and aggressively inviting us inside. I was instantly overwhelmed because something about it scared me. Quickly signaling to Lorenzo we should move on, I hoped we could find a more laid-back bar that was more conducive to conversations.

Leaving the suited man behind, we wandered the streets perpendicular to the beach until we peeked into a nearly empty bar with a more mellow atmosphere. We walked in, sat down, and two women soon joined us while others took turns apathetically pole dancing. The staff was at best unenthused and at worst grouchy. Still, it seemed like our best option, so we stayed.

Not long after we got to our table I realized Lorenzo and I had hardly discussed a game plan. What do we talk about, and how do we act? The assumption is that we want to pay for sex, so how do we handle that? Do we have to build some rapport first, or should we just tell them what we’re doing?

Luckily and unluckily, the women were professionals. We felt at ease talking to them, but they were doing their best to seduce us. That included pressure to buy very expensive drinks for ourselves and them. Since I don’t drink alcohol, Lorenzo ended up drinking for me, and his tipsiness didn’t help our cause.

At some point, the women took us for a smoke break outside where they gave us our first of many privileged glimpses into the personal lives of sex workers. One complained about working a boring retail job during the day. The other had a child whom she’d leave with her mom at night, and she was confident none of her family knew what she was doing. Even though these facts were all consistent with I imagined, hearing the women talk about themselves engrossed me.

After some more time together, the ladies excused themselves presumably to use the restroom. Somewhat panicked by our mounting tab, I turned to Lorenzo to regroup and outline what to discuss from then on.

Most importantly, we had to find out if the women even recognized the problem the app could solve. As foreigners ourselves, we could reasonably inquire, “Can knowing English help you make more money?” Once they came back, we talked a lot more about English, but that quickly devolved into them eagerly parroting sexual slang to us in barely understandable attempts at our language.

We weren’t accomplishing much, it was getting late, and it became clear to the women we weren’t going to leave with them, so we asked for the check. At that time Brazil’s currency was far stronger, making our hearts sink when we realized we each owed over $50, an unacceptable hit to the survival budgets we had imposed upon ourselves.

It was an expensive and ineffective outing, but at least we had begun. In the future, we’d have to be more deliberate with our approach and more efficient to get a significant sample size of responses in the short time we allotted ourselves on weekends.

Um Programa Para Garotas de Programa

On a subsequent trip, we finally narrowed down our target location. Unlike the more discreet locales we visited before, Balcony was an anomaly. It defiantly inhabited a beachfront corner of a renowned stretch of Avenida Atlântica grasping for its bygone glory days.

To call Balcony a brothel might be technically inaccurate, and even now I don’t understand its business relationship to prostitution. At street level it was an innocuous awning-covered restaurant serving mediocre, moderately-priced American fare (with the exception of its underrated 4 am breakfast buffet). Throughout the day and evening, couples and even families dined there. However, the establishment’s connected interior housed an ample sports-bar-like area where prostitutes and middle-aged, white male tourists mingled. While I never ventured there, upstairs was a separate nightclub apparently boasting rooms for hourly rates.

What was so ideal about Balcony, besides being two blocks from Lorenzo’s apartment, was that we could casually enter and exit because the property didn’t have bouncers or lines, let alone doors.  On weekends the prostitutes and their raucous clientele would overtake the adjacent plaza, so sometimes we wouldn’t even need to go inside to meet potential users. This layout facilitated a relaxed, welcoming vibe that made conversation with the women easy and even enjoyable.

Perhaps most crucial, though, for our bootstrapped project was that we didn’t have to spend any money there.

Our light wallets and unique purpose created the issue of how to actually approach the women. Immediately stating our attention could draw bewilderment, whereas prolonged chatting under the guise of being typical customers could rob the women of precious time with income-generating men. After many negative reactions, we perfected our introductions to be a compromise between both ends of the spectrum.

Eventually our routine converged on either asking the women in Portuguese if they spoke English or just simply opening in English. We’d then use our own interaction as an example proving the need for our app, and if they were receptive, we’d continue soliciting more feedback. Frankly, the responses were mixed, and surely many positive reactions were to appease us while some negative answers just didn’t understand our shoddy explanations. With practice our pitch became so effortlessly delivered that we could split up to each meet a dozen women a night, and it was then that things started to get interesting.

Their Stories

NOTE: I’ll answer what you’re probably wondering. No, Lorenzo and I didn’t have sex with any of the women from our outings. Believe it or not, we couldn’t afford to pay the $50 to $500 to do so. Ethically and politically, I see nothing wrong with prostitution as long as it’s verifiably consensual, safe, and legal. Like drugs, prostitution happens everywhere regardless of regulations or norms. As such, my position is that we should seek to contain its risks while empowering sex workers. Nonetheless, I never have and never will pay for sex, not because I look down on it but because I myself am not fulfilled by that kind of encounter.

*Camila stuck out. Her dress, while form-fitting, was elegant and exposed far less than the other women. I doubted whether she actually was working by how she stood aloof from the schoolyard-like cliques of other women cackling and jerking around her. She appeared confident other than how she impatiently shot her glance repeatedly from the pulsing crowd to her phone and back. It was as if she awaited a date who was 10 minutes past standing her up. From that mysterious impression, my research goals took a backseat to discovering who she was and why she was there.

As if I couldn’t start with anything else after introducing myself the same way so many times, I approached with, “Hey, do you speak English?”

Yes, she certainly did. In fact, she expressed herself more fluidly and intelligently than most any other native Brazilian I could remember meeting. I was engrossed by everything she had to say because she was such an outlier.

“I learned English when I was little from listening to my uncle’s Rage Against the Machine CDs.”

In spite of her metal-infused educational foundations, she was witty and eloquent, defying society’s stereotype of sex workers. Moreover, she was in her final year of medical school at PUC-Rio, an elite private university where many of my upper-class Brazilian acquaintances studied. I wondered if she sat next to them in class.

Understandably, but to the chagrin of my inquisitive nature, she wasn’t too forthcoming with other details of her life. She told me she came from a little-known interior state that prostitutes its ecosystem to voracious Chinese appetite for raw goods. Moreover, by her atypical demeanor it made sense when she mentioned she’d only do this work around once a month to pay personal expenses. Yet never did she convey feelings of embarrassment about this side job even if it was a secret—a practical one considering machismo’s omnipresence in even Brazil’s most esteemed professions.

Lorenzo joined the conversation, and we must have talked for an hour before she likely remembered why she was even in that Brazilian Applebee’s-cum-bordello to begin with. In all the weekends we returned to Balcony, I don’t recall speaking with Camila again, though I sincerely hope by now her name is preceded by the honorable “Dra.”

Then there was *Solange, reminiscent of a carioca version of hip-hop celebrity Amber Rose, whom Lorenzo met without me at Balcony. As she was basking in her professional peak in her later 30s, she boasted of spending most of the year abroad where she made much more money. Still, she planned that the euros, or pounds, or dollars would lead her back to Rio for FIFA’s nearing June-July mayhem.

Solange was what Silicon Valley VCs would label in a deck as an “early evangelist.” She enthusiastically saw the need for what we were attempting, and she wanted to help. She was going to tell all of her friends about the app and make sure they used it. When our nights became monotonous, seeing her light up as we walked inside and wave Lorenzo over to introduce him to someone new made me reconsider my occasionally foul mood. Unfortunately, by the time we had a downloadable app, it appeared Solange had already jetted off to Europe before we could get a list of leads from her.

Still, perhaps most memorable of all was *Martina from the Amazon. Quickly getting to know us from our repeat visits to Balcony, she didn’t seemed concerned with wasting her time chatting. In particular, she recounted the saga of her romance with her abusive, on-and-off, wealthy foreign boyfriend whom she lived with at times in Europe. It was a lot to take in, but at the same time I was glad she trusted us enough to share the details. In return we told her a lot about ourselves, and she listened eagerly.

Most entertaining, however, was that while it was abundantly clear she was financially unattainable to Lorenzo, Martina seemed to genuinely pursue him anyways. Sometimes I had to return the focus from her flirtations back to app feedback and getting her colleagues’ contact information. Even before dawn as Lorenzo ensured the buffet’s cream cheese and jelly mostly skipped his mouth on a direct path to his t-shirt, she still didn’t give up on him.

Ultimately, the women’s diverse personalities and stories became a highlight of our project for me. As we had to suspect the intentions behind their words and mannerisms, the women could have just as easily mistrusted us, two dubiously Portuguese-proficient gringos with strange non-sexual requests.  (Of course, that’s all neglecting both the blatant and more subtle gendered power dynamics at play.) Perhaps it’s wishful thinking that Camila and others’ interactions were real in the face of a sex marketplace predicated on feigned desire. Still, I like to believe what these women showed me amid the muffled soundtrack of ’80s power ballads was at least partially their true selves.

Two-Man Hackathon

Months of hiatus followed due in part to the demands of our primary jobs and in part to procrastination over actually incorporating user feedback into a working Android app. Largely from being in the right place at the right time, after the FIFA draw announcement amped fanfare, my travel business quickly made headlines—first in Forbes, then The New York TimesCNNand other international media. Consequently my original reason for joining in on Lorenzo’s idea was no longer relevant.

By then it didn’t really matter. Both Lorenzo and I became motivated to get the app done and onto as many devices as possible before the FIFA opening ceremony. To be fair, that was Lorenzo’s goal the entire time as he envisioned a whole suite of trade-specific tools for professions that could benefit from English access—taxi drivers, bellhops, snack vendors, etc. He even had grandiose plans for enterprise software and consumer platforms for sex workers.

Unfortunately, we had only allocated one do-or-die weekend to lock ourselves in Lorenzo’s apartment and produce Língua Boa v. 1.0. It was going to be a rough “minimum viable product” and a rough, mostly sleepless 48 hours. Our fuel of choice (or by necessity) was $1.00 pastel chinês meat and dough bombs from the unappealing bakery below Lorenzo’s building.

We agreed the logic behind the app was ultra-simple. We’d make a glossary of the 100 most useful words and phrases listed in chronological order based on a standard prostitute-client interaction. Each entry would have the English and Portuguese translation alongside a relevant rights-free image with touch-activated English audio. The content themes moved from greetings to flirting to negotiation to sex acts, including the right amount of health, safety, and comfort-related vocabulary.

Because none of our female friends agreed to voice the bawdy audio, I was the one to recite “Nice to meet you” and “My name is” (among more NSFW terminology). Of course, the few friends I’ve showed the app to find that part hilarious.

Also worth noting is that the real use case is less a way for users to be able to recite useful words and more for them to operate the app as an audiovisual aid in their client interactions.



Since Lorenzo is the one who can actually code, I was left to select the vocabulary, find images, and figure out the Google Play Store. I’d like to say it was a 50-50 effort, but Lorenzo deserves most of the credit.

Notwithstanding his hard work after much frustration, I did come up with the app’s name, Língua Boa. It’s a smug double entendre that’s meant to appeal to the nature of the users’ work, and if you download the app (Android only) or view our hastily-made logo, you should understand.

Given the app’s content, it was a gamble as to whether the Google Play Store would accept our submission. Luckily we had nothing more than the $25 application fee to lose, and possibly because of Google’s laxness the app was never removed.

It’s the Journey, Not the Destination

I’d love to report we got our app to thousands of sex workers across the country during the World Cup and heard high praise of its utility. In a last-ditch effort to spark some PR, I did actually have an interview with The Guardian about the app, but it was never published.

The truth is Língua Boa is crummy, and it was supposed to be, at the least in its first iteration. It’d take weeks more work of testing and development for users to find some value in the app. Though we revisited Balcony a few more times in subsequent months, we didn’t invest enough time into making Língua Boa something anyone wanted.

Certainly we both learned a lot from this entire process. I was grateful for the exposure to a population I otherwise wouldn’t have come to know. I can’t claim to comprehend much about the economics and social reality of sex work or have much first-hand knowledge into the dark underbelly of that industry even if we did see some signs of illegal drug use and underage prostitution. (Balcony was suspiciously shut down on the World Cup’s opening day over child abuse allegations.) Though this project proved not all prostitution is demeaning or exploitative, I deeply respect the individuals, NGOs, academics, and public sector serving at-risk segments of the sex trade.

Toward the end, the experience for me became much more about the practice in empathizing with a taboo group and finding ways to improve sex workers’ livelihoods and well-being. No, we didn’t get far, but my point is that this is a fight worth fighting.

There’s untapped human and commercial potential serving not just sex workers but other “untouchable” populations like the disabled and the unexotic underclass, not to mention the 2.7 billion people living on $2 a day or less. Nevertheless, strides won’t be made without input from and ownership of new initiatives by these groups.

Open minds, creativity, and relentless resourcefulness are what we need to make progress. I’m ready to get to work—are you?


*Names have been changed upon request or to protect identities.

**All quotations have been approximated from memories of personal experiences taking place between September 2013 and June 2014.


What Next?


I trembled on stage as I gripped the handheld whiteboard scrawled with my answer to the tie-breaker question. My fellow sixth graders sat in the audience fidgeting in their seats with their fingers crossed, hoping I’d beat the other finalist, a fifth-grade savant. I’d written “Scotland,” but the correct response to which country is a former British penal colony was Australia. I was wrong. The other side burst into cheers filling the chapel of my tiny Jewish elementary school. I swallowed a lump in my throat as I shook hands with the ecstatic victor of Temple Israel of Hollywood Day School’s qualifying round for the 2002 National Geographic GeoBee.

The sting of defeat from that moment sticks with me today. However, it’s actually the lead-up to that story that’s far more important for me now. Fundamental to who I am as an adult is a former youth obsession with the names of states and countries along with myriad other world geography trivia. From as young as I can remember, I absorbed every factoid possible about places near and far.

A Childhood Rite

Fortunately, I practiced a helpful ritual every night as I anxiously awaited my mom to put my dinner on the table. Between kitchen-bound shouts of, “What’s for dinner?!,” I’d fervently dart my eyes back and forth over a placemat printed with a map of the US. The visual osmosis was so strong that I could doodle accurate borders of all 50 states from memory in class while tuning out redundant lessons on Hebrew vowel mark placement.

My associated fascination with planes probably made me an annoyingly precocious child on our flights to visit distant family. Before the days of rainbow spectrum terror alerts, my dad would always succumb to my pleas to visit the cockpit to get my metal “wings” pin from the pilot. And while in air, I’d fog up my seat’s ice-specked window with my chubby face pressed firmly against the glass at 35,000 feet. Between servings of peanuts and V8, my gaze was fixed downward at Earth’s vast surface while I imagined the sensation of gliding through a blanket of cotton candy clouds.

In my teens I was giddy to explore somewhere beyond the familiar (as exotic as Passover vacation seeing my relatives in Livingston, New Jersey could be). My wish was granted, and I visited Europe with my parents, eventually partaking in month-long, Spanish language immersion trips to Spain and Argentina with other high schoolers. Then, when I wasn’t ready to go to college immediately, I spent a formative gap year volunteering in Chile.

Latin America’s passion and alluring economic prospects made it my preferred region, and I was determined to become an expert. Consequently, I learned Portuguese, did a semester-long study abroad in Brazil, and kept returning to that dangerously seductive land. (If you’ve read this blog, you know what happened next.)

After a couple years of samba, acai, and starting a venture in one of the worst nations for business, I came to a crucial realization. I was static, an unwelcome requirement of running my enterprise there. At that pace, how was I ever going to reach those abstract corners of my childhood dinner placemat map?

Considering the constraints of human life expectancy and the mounting obligations that come with age, I decided now is the time to journey. Particularly, to go everywhere I want, I have to always be moving. The globe is too expansive for lingering anywhere too long. Yet, endeavoring to see everything is a futile pursuit.

Instead, I want to experience that which is uniquely extraordinary. Certainly there are lots of nice beaches in the world, but I’m only interested in the superlative beaches–the one with the whitest sand, or the sharpest cliffs, or the most entertaining monkey inhabitants. Likewise, there are many mystical temples, an abundance of exuberant festivals, and fancy restaurants in excess. I can’t, nor do I want to, experience them all.

Go East, Young Man

Did I close my eyes and spin a globe? No, I was very deliberate in picking a destination. I’ve just begun a year traveling most of the 19 countries in Southeast and then South Asia. Well, why there?

First of all, the region seems to be the cultural opposite of Latin America, where I became too comfortable after living there for three years from 2008 to 2014. Meaningful travel (not to be confused with vacation) should challenge you physically, intellectually, spiritually and emotionally. Otherwise, how can I expect the experience to teach me anything? I know I’ll be uncomfortable here because I’ve never been to Asia until now, know few people here, don’t speak its languages and am ignorant of its history and culture.

This doesn’t mean I won’t spend some time doing the fun, touristy things, especially if they’re unique. Already in this first month spent in the Philippines: I learned to kitesurf, joined a five-day island-hopping boat expedition, and achieved Open Water diving certification while exploring Japanese shipwrecks from WWII at 80 feet below the surface.

Second, this region is very affordable to visit. In Vietnam, Cambodia, Indonesia, and other countries a backpacker can do a lot on a $50 daily budget. That’s necessary for me, so I can stretch my earnings from Brazil and still have enough of a cushion for whatever I do next. I’m confident I won’t break the bank by travel hacking (signing up for credit cards to get free airfare and accommodations), couchsurfing (both with friends and their friends as well as through Couchsurfing.com), and judiciously evaluating which activities to book and which to skip.

Third, exploring this region is key to my career aspirations. In broad terms, my interest is using innovative approaches to solve social and environmental problems. More specifically, I’m intrigued by scalable, for-profit models to improve the poor’s livelihoods and quality of life. As such, it’s fitting that Southeast and South Asia already have both lots of need for and activity toward those efforts. For example, India alone possesses 800 million people living on $2 a day or less, yet it’s also home to some of the most promising organizations serving that demographic.

My plan is to meet with such social enterprises to see their field operations in action. Simultaneously, I expect to have significant interactions these business’ customers and other poor people to better understand their reality from their perspective. This could take the form of organized tours offered by renowned development institutions such as Grameen and BRAC in Bangladesh. Alternatively, I could end up asking my tuk-tuk driver to sleep on the floor of his house, cook meals with his family, and play soccer with his kids.

To Adventure

I didn’t have anywhere to sleep tonight until a few hours ago, but had I constructed a regimented itinerary I’d have missed crashing the traditional, drunken wedding of a friend’s Lao colleague this weekend. Showing Lao grandmas how to Harlem Shake to Indochinese crooning in a village set beneath dramatic, limestone karsts isn’t an activity in any tour packages.

My point is that the structure of a trip itinerary would only constrict my open-ended travel goals. I want to be able to change directions on a whim, especially when so much of this region is unknowable through TripAdvisor reviews and Lonely Planet guides.

Ultimately, it’s premature to make any commitments so soon, but I envision this year leading to the connections, experience, and inspiration for starting another business. In the meantime, I’m just wandering.

P.S. You can always see what I’m up to more regularly on Facebook and Instagram.