Elliot, What Credit Card Should I Get?

2015-12-20 18.19.20

In the past 18 months, I’ve been approved for 24 new credit cards.

When I tell people that, they’re often shocked, stuttering how they didn’t know such a feat was even possible or why anyone would ever want to do that. The reactions I provoke from my nonchalant statement are understandable considering we’re taught from early on that credit cards do to your finances what smoking does to your health.

So, for most people who haven’t questioned such common sense, it can be hard to explain that, after hundreds of hours of research and lots of practice, I’ve learned “travel hacking” to earn free flights, hotels, and cash. As such, I’ve been able to stretch my savings for maximizing my non-stop traveling throughout Asia since January. Better yet, I’m also unemployed and haven’t made much money in over a year.

Oh yeah, and my credit score hovers in the mid-700s, which most banks would rate as “excellent.”

It all sounds reckless and too good to be true, but I’ve explained before how doing this carefully actually improves your long-term credit score. Other than being American or living in the US (where banks’ lucrative promotions make this possible) and having average or better credit, there aren’t any prerequisites to travel hacking. Of course, the practice can be disastrous for anyone who’s irresponsible and disorganized, which is why your parents tried to scare you about credit cards.

From my past post and myriad conversations, my experience with travel hacking has clearly piqued the curiosity of many friends and friends of friends. As a result, beginners commonly ask me, “What credit card should I get for travel?”

The answer is there’s no one credit card everyone should get. Rather, you should make your decision based on your travel goals, spending habits, and willingness to learn how to gain the most value from your credit card. Furthermore, it helps to determine from the outset if you want just one or two cards that you’ll hold onto long-term or if you might take travel hacking more seriously and eventually apply for far more cards.

Some important questions to ask yourself before submitting any applications are:

  • How much do I normally spend per month and on what types of expenses (e.g., rent, groceries, gas, dining, travel)?
  • To and from where do I want to travel, where will I sleep (e.g., luxury hotels, Airbnb, hostels, guesthouses), and what will I do there (e.g., lounging on a beach, visiting museums and sightseeing, eating at fancy restaurants)?
  • When will I travel, and are my travel dates and times flexible?
  • What other card benefits do I want (e.g., airport lounge access, travel insurance, purchase protection)?

Still, whether you’re looking for a single credit card to keep long-term for all your spending or you’re interested in trying a few credit cards to reap multiple sign-up bonus offers, in most cases I end up recommending only a few different cards to apply for first.

I’ve had all of the following cards at one point, and these are their key strengths and weaknesses:

Chase Sapphire Preferred

The offer: Earn 50,000 Ultimate Rewards points (plus 5,000 more points for adding an authorized user who makes a purchase in the first three months of card membership) after spending $4,000 in the first three months of opening the card. Earn 2 points per dollar spent on travel and dining and 1 point per dollar on everything else. The $95 annual fee is waived in the first year.


  • The sign-up bonus is worth at least $550 in statement credits but can easily be worth over $1,000 if redeemed on Chase’s airline and hotel transfer partners, such as United Airlines and Hyatt hotels.
  • The current offer is the best sign-up bonus ever publicly available for the card, by a difference of 10,000 points.
  • The Sapphire Preferred is known to have the best included travel insurance of any card available.


  • Maximizing value from transferring Chase Ultimate Rewards points to travel partners can require patience to learn about partners’ rewards programs and flexibility to book award flights and hotels when there might not be the desired award availability.
  • Unless you spend a lot of your money on travel and dining, the Sapphire Preferred’s regular earning ratio is weaker than its competitors.
  • A new rule being enforced by Chase seems to deny any applicant for this card who’s opened five or more new credit cards (from any bank) in the past 24 months.

Capital One Venture

The offer: Earn 40,000 Venture miles after spending $3,000 in the first three months of card membership. Earn 2 miles per dollar spent on all purchases. The $59 annual fee is waived in the first year.


  • The sign-up bonus is worth $400 toward any travel expense.
  • There is no minimum redemption amount for award redemption.
  • For now it seems you can repeatedly redeem your miles against the same one travel purchase with no limit on the number of times you can do so.
  • Venture miles can be redeemed for travel expenses that posted as far as 120 days prior to the redemption date.


  • When you apply, Capital One typically does “hard credit pulls” on all three major credit bureaus, Experian, Equifax, and TransUnion, whereas most other credit card companies only use one bureau.
  • Capital One seems to approve individuals for credit cards only if they already have a Capital One bank account. If you want to sign up for a Capital One 360 bank account, you can earn yourself $25 bonus (plus $20 referral for me) by using my link. Fortunately, applying for and opening a Capital One 360 bank account doesn’t affect your credit score.

Barclay Arrival Plus

The offer: Earn 40,000 Arrival miles after spending $3,000 in the first three months of card membership. Earn 2 miles per dollar spent on all purchases. The $89 annual fee is waived in the first year.


  • The sign-up bonus is worth $400 to be redeemed toward most travel expenses.
  • The Arrival Plus has one of the best all-around earning ratios of any card, effectively giving you 2% cash back on all purchases to redeem in the form of statement credits toward travel. This makes it an excellent choice to be your only credit card.
  • Barclay instantly issues cardholders a 5% rebate on all redeemed Arrival miles.
  • Arrival miles can be redeemed for travel expenses that posted as far as 120 days prior to the redemption date.


  • The minimum award redemption for travel expenses will soon be 10,000 miles, meaning you can only redeem for expenses of $100 or more.
  • Certain travel categories such as museums and sightseeing are, or will soon be, ineligible for travel award redemption.

I hope this gives an overview of the major cards most beginning travel hackers should consider. I’m happy to help friends with this hobby if you have any questions!


I Never Meant It When I Said, “Thank You”

My life is easy.

For the past year I’ve hopped continuously from country to country (15 so far), experiencing awe-inspiring nature, exciting activities, and satisfying food. Before that I got to start a business in a place I loved, and even despite some trying moments, I felt fulfilled and profited enough to travel this year without working.

From birth through college, my life was similarly easy. As a healthy, upper-class, white American male from a loving family, someone else always paid for my elite education in addition to taking care of all my wants and needs. I got to have fun, enjoyed my friends, and never had to worry about much.

Moreover, nothing really bad has ever happened to me. I’ve never been hungry, sick, attacked, jailed, stolen from, morally wronged, discriminated against, nor denied my rights in any serious manner. At worst I’ve felt mild stress and disappointment, maybe most when I didn’t get into my first-pick college and had to settle for my second choice.

Altogether, I must be in the 99.9th or 99.99th percentile of quality of life among humanity. It’s almost all sheer luck—I’ve never done much to deserve my excellent circumstances and all the good others have done for me. Sure, I’m proud of my own effort toward certain accomplishments, but all I mostly ever had to do was play by the rules. And if along the way I struggled, I could always depend on a responsive, caring support system of family, teachers, mentors, and friends to go above and beyond to help me. Not to mention, my gender, the color of my skin, the country on my passport, and the institution on my diploma mean I’d still be far better off than most even if my support system were to crumble.

That’s all nice, but I’ve long felt a lingering discomfort over one problem of paramount importance. Unlike for so many of the inherited conditions fostering for my success and happiness, I am totally responsible for this problem.

For all I have I’m not grateful.

Yes, I know I should be; yes, I comprehend from an intellectual standpoint the unfathomably slim odds that the universe conspired toward my mere existence; yes, I recognize logically how it’s far less likely still that my existence could be so extremely easy. Allowing my mind to occasionally ponder this absurd probability hasn’t made me a thankful person.

To be such a person would require profoundly and overwhelmingly feeling, I don’t feel gratitude.

Upon recollecting times I thought I felt gratitude for my circumstances or selfless and caring acts from others, that sensation hardly ever persisted for more than a few hours. If anything, in those times I instead indulged in relief and joy more than gratitude. After all, my resulting words and actions were absent of a true karmic debt to others and more than fleeting recognition of their hard work and sacrifices that improved my life.

Of course, I offer “thank you”‘s countless times every day to strangers, acquaintances, friends and family while face-to-face, over the phone, and in writing online. Like so many of us, my thanksgiving is meaninglessly and mindlessly automatic, drilled into a regiment of good manners training from youth. Even signing off emails with “Thank you” feels so common that I’ll often add, “I appreciate your time and help,” to curry favor because the former would go overlooked.

My ungratefulness ends now. Or, at least I’m committing to taking the first step toward genuine gratitude.

Why am I doing this? At minimum I want to bolster my mood, as research published in the journal Cerebral Cortex shows gratitude stimulates both stress-regulating and pleasure-sensing areas of the brain. Yet, I hope to reap other wide-ranging benefits of gratitude from less physical pain to higher self-esteem to winning new friends.

My primary motivation is selfish, and for now I’m not ashamed of that, especially if the change eventually stokes me doing some good for others. One example summarized in The New York Times is:

“Researchers at the University of Southern California showed this in a 2011 study of people with high power but low emotional security (think of the worst boss you’ve ever had). The research demonstrated that when their competence was questioned, the subjects tended to lash out with aggression and personal denigration. When shown gratitude, however, they reduced the bad behavior. That is, the best way to disarm an angry interlocutor is with a warm ‘thank you.'”

Simply promising myself that I’m going to reflect on more of the good in my life probably won’t change how I feel. Therefore, I’m going to attempt a structured gratitude experiment inspired by Martin Seligman, founder of a field called “positive psychology” (which focuses on human flourishing in lieu of mainstream psychology’s obsession with our mental defects). In his book Authentic Happiness, he advises practicing the expression of gratitude in letters to colleagues and loved ones.

So, for 30 days preferably as part of my morning routine in order to build a new habit, I’ll express my gratitude to one new person each day. To further quantify my habit but limit the barriers (or excuses) to following through,my goal is communicating 100 or more words of unrestrained gratitude to at least one person per day. My communication may take the form of email, social media message, handwritten letter, voice/video message, or speaking in person. Of course, to reinforce this plan, I’ll share it with my accountability group and keep them updated on my progress.

To add a bit of empirical rigor to this exercise, I’ll keep a log. In it I’ll track the recipients, the medium used, my mood (on a -5 to 5 scale) immediately after each day’s communication of gratitude, and notes on any reactions I receive from the recipients. Afterward, with the key disclaimer of a placebo effect and other variables at play, I’ll search for patterns.

I suspect my relationship with each recipient will affect not only how hard it is to convey my gratitude but how doing so makes me feel. Maybe expressing gratitude to the people I’m most estranged from will make me feel best in the end, or maybe that’ll be true of friends and family I’m closest to but most take for granted. There are undoubtedly many other factors I’m not even considering, but regardless I’ll report back after a month!


No, Mark Zuckerberg Didn’t Donate His Fortune to Charity; He Did Something Far Greater

Since Mark Zuckerberg’s $45 billion philanthropy pledge announcement, critics have derided he and his wife Priscilla Chan’s decision as blatant tax dodging and mere power consolidation. Zuckerberg’s detractors are justifiably suspicious of mega-billionaires’ self-proclaimed altruism through charity, especially as wealth inequality in America peaks. Moreover, cynicism about the ultra-rich’s munificence is fair because often their social spending is only made possible by their wealth-generating businesses that exacerbate society’s most pernicious problems.

In reality, Zuckerberg and Chan did not vow to donate 99% of their wealth to charity. They did something far greater for humanity. Or, at least they took a crucial, pioneering first step toward doing so.

At face value, all Chan and Zuckerberg did was create a legal entity with the amorphous mission of “advancing human potential and promoting equality.” Though unusual for prominent philanthropies, the Chan-Zuckerberg Initiative isn’t structured as a private foundation like the Bill and Melinda Gates Foundation. Rather, CZI is a Limited Liability Company (LLC).

There are vast differences between LLCs and foundations, which both underpin the criticism of CZI and reveal the intentions of its founders. While private foundations typically make grants to other non-profit organizations, LLCs have greater flexibility in what activities they can undertake.

In Zuckerberg’s own words: “We’ll donate to good non-profits and invest in good companies. The key is to be able to fund whoever is doing good work, regardless of how their organization is structured. Many foundations can’t do this, but because of our structure we can.”

The keyword is “invest,” and therefore, that’s precisely what CZI is: an investment vehicle. So, with proceeds from selling the Facebook stock it owns, CZI will invest in mission-driven, for-profit companies. Such investments may generate uncapped profits for CZI, which Zuckerberg insists would be entirely re-invested into additional social spending.

Yes, at face value, and under the theory that Zuckerberg is a status quo techno-baron, this is frightening. What’s stopping Zuckerberg and Chan from following the likes of the Koch brothers to fund an agenda that makes them and their fellow billionaires richer? Frankly, nothing besides bad PR. Of course, if they were to have opted for a foundation structure, then they’d be forced to give money to more conventionally charitable causes. 

Still, I’m more optimistic about Zuckerberg and Chan’s intentions and eventual impact. After all, they’ve made past gifts exceeding $200 million to public school systems in Newark and the Bay Area as well as investments in education companies like MasteryConnect.

Many doubters nevertheless cite that one of those donations, of $100 million to Newark schools, financed an undemocratic and ultimately failed reform process. As Zuckerberg and Chan’s first foray into massive-scale philanthropy, an initial outcome of mixed results is acceptable, particularly if the donors have recognized their mistakes and learned from them.

Yes, CZI’s LLC structure lacks the accountability mechanisms that apply to government programs and publicly-traded companies. However, at the same time, the LLC gains an advantage in that its administrators won’t have to pander to voters for reelection every few years or placate shareholders every quarter.

Consequently, Zuckerberg believes CZI can “make long term investments over 25, 50 or even 100 years” due to more freedom from short-term thinking. A prime example he offers in his Facebook announcement is: “Today we spend about 50 times more as a society treating people who are sick than we invest in research so you won’t get sick in the first place.” Almost certainly, CZI will fund such medical research and other innovations that can have long time horizons, which are unappealing to other donors and investors along with government.

Besides the time horizons of these investments, it’s clear that Zuckerberg and Chan are employing a portfolio strategy in deploying their capital similar to what’s common in the venture capital industry. In taking the risky bets others shy from, they accept and expect that not all of their donations and investments will yield positive results, but that a select few will bring outsize social benefits. And for the huge successes of their portfolio, they hope that the positive magnitude of those successes will far outweigh the negative magnitude of the failures.

Better yet, unlike a private foundation that must annually donate 5% of its endowment, as an LLC CZI can donate, invest, and spend as little or as much as Chan and Zuckerberg see fit. Thus, CZI can provide adequate financing for the opportunities and at the times it deems best for humanity.

Even if Zuckerberg and Chan have so far directed relatively little of their vast fortune into social benefit initiatives, the CZI launch is perhaps the strongest indicator yet of a new paradigm for philanthropy. No longer will issues like global poverty and climate change remain the exclusive purview of gridlocked governments and donor-dependent non-profits. Zuckerberg and Chan (though hardly first movers) are building a future in which solutions to social and environmental problems will be designed as for-profit businesses that receive investment from funders seeking financial returns.

In fact, in that hard-to-imagine, radically-different future, Silicon Valley moguls won’t be the only participants in effecting change. Partly because more capital will flow into profitable approaches addressing our most dire challenges, more and more of us will work with the organizations that people like Zuckerberg and Chan are supporting. Better yet, when more examples prove this burgeoning philosophy, as employees and investors we’ll make more money by working with and supporting these companies.

Now what we most need to spark this shift is a mission-driven company to become as highly valued and prominent as Facebook is among its conventional peers. Only then will similarly oriented businesses be able to convince the most promising talent and most risk-taking investors to join them. Until then, the brightest minds and most money will continue to flow into comparatively more lucrative yet less socially beneficial industries.

Ultimately, I applaud Chan and Zuckerberg for making a bold decision about how to use their privilege and power to advance society, in spite of the wide-ranging reproval their announcement drew. True, it’s healthy to distrust the billionaire class, but let’s recognize and defend their imperfect yet promising nontraditional efforts to do the most good for the most people.


The Hardest Journey


Hulking, imposing behemoths stood confidently before me. Asserting themselves over the landscape, they occupied my field of vision from end to end. Bulbous clouds made haughty yet futile attempts to blow past, but were forced to split, contour, and yield to walls of sharp ridges.

A wave of guilt washed over me as I held my awestruck gaze. Every time before I’d ever said “mountain” was a lie. These were real mountains–five-mile-high heavens-scraping monuments of rock and ice. The Annapurna clan guarded by their Himalayan brethren put all other vertiginous families to shame.

To truly appreciate their power, we soft, mortal humans can only walk beneath, across, and (for those who dare) atop them… and then keep walking some more. So, that’s exactly what my friends and I did for 19 straight days on Nepal’s Annapurna Circuit Trek this October and November.

To be fair, I alone never would’ve proposed undertaking the mission of trekking for four to eight hours per day to an elevation of nearly 18,000 feet. I enjoy the outdoors, but only as a brief escape from cities. Maybe Boy Scout camp quashed any potential affinity I ever harbored for existing in unbridled nature, in all its shower-less and insect-plagued glory.

Far in advance of visiting Nepal, my friends diligently planned our trek, sharing gear lists, references on trail guides, and warnings about altitude sickness. However, having worn the same pair of flip flops daily over many months in tropical Southeast Asia, I was daunted by the impending necessity of buying a down jacket, long underwear, and a water filtration system. Then, learning that an out-of-season blizzard in 2014 killed over 20 trekkers on our chosen route didn’t brighten my outlook. Moreover, Nepal had hardly recovered from this April’s catastrophic earthquake.

After flights were booked and our guide arranged, our prospects quickly worsened in the weeks preceding our trip. In September Nepal’s fragile post-Civil-War democracy passed a new constitution, some parts of which angered a prominent ethnic minority with strong ties to India. Shortly thereafter, this led to an unofficial blockade on fuel imports from India into Nepal, which has crippled Nepal given the landlocked country’s dependence on India for virtually all its fuel.

Closely following the dire news developments, we feared the fuel crisis would cancel flights, constrict bus circulation, and limit everything from food availability to emergency helicopter rescue services. We debated canceling our trip while the US Embassy and Nepali contacts warned us it was dangerous to travel, especially for mountain treks.

We went anyways.

And it was one of the best decisions I’ve ever made.

It sounds foolhardy, but we determined there was little risk in at least flying to the capital Kathmandu, assessing first-hand the situation on the ground, and leaving immediately if necessary. Fortunately, upon landing, I didn’t perceive a country in crisis. Sure, taxis had doubled their fares, and menus were pared down as cooking gas supplies dwindled, but it would’ve been a shame to halt our expedition due to those inconveniences.

Meeting our beaming guide Krishna for the first time impressed me with the calm resilience of Nepali people. As the breadwinner for his wife, two young children, and extended family, it was tragic enough that the earthquake razed their home and forced them into temporary shelter. Worse was that the blockade further threatened his livelihood from tourism, which he had built starting as a teenage porter hauling back-bending loads of supplies for trekkers. Having experienced such enduring hardship, he later encapsulated his nation’s ethos when he told me, “Even when I’m suffering, I’m happy.”

Each day on the trail delivered new superlatives for me. There was the highest lake, the greenest valley, the widest rock face, and the fastest river, not to mention the greatest exhaustion, the thinnest air, and the most blistered feet.

It’s true that there was no particular section in and of itself that any reasonably fit person couldn’t handle. Nevertheless, lugging my pack (We opted not to hire porters.) up and down steep, uneven, and sometimes slippery inclines for 19 straight days without ever a full day of rest was challenging. Then, there were days on end when I could never warm up my entire body, even inside my sleeping bag, because the temperature indoors at night probably dipped as low as 15 degrees Fahrenheit. Beyond that, climbing above 12,000 feet, I felt as if I were breathing through a straw that kept getting thinner and thinner. Of course, it didn’t help that we often had to awake before sunrise and forced ourselves to stay up later because it’s dangerous to oversleep amid the low oxygen levels of high altitudes.

All the factors together meant the Annapurna Circuit was by far the most consistently physically demanding experience of my life. Thus, the trek forced me to build the mental endurance needed to conquer the tedium of thousands upon thousands of steps when I most longed for a warm shower and 15 hours of deep sleep. Ultimately, I felt deeply rewarded by the mental stamina that let me witness some of the most spectacular natural wonders of my life.

A day-by-day log of what we did and what we saw wouldn’t do justice to the see-it-to-believe-it beauty of the over 100 miles of trail we walked, but two highlights I’ll always remember.

First, during a three-day side trip to 16,000-foot-high Tilicho Lake, we descended from the lake to base camp just as snowflakes began to trickle down in the afternoon. The snow continued heavily and steadily, nearing a foot deep by the morning. So, we were forced to decide whether to stay at the isolated base camp and wait out what the forecast predicted could be another couple days of snow or hike for six hours to the nearest major town before the snow could intensify.

We weighed the risks and chose to hike out to avoid being trapped at base camp. The path was harrowing as the ground alternated between hard ice and dark slush, forcing us to judiciously choose our steps and dig our trekking poles. To avoid further danger, we left considerable space between ourselves along the mountainsides with ominous “DANGER! ROCK SLIDE ZONE” placards. Still, we all slipped again and again, but luckily never far enough to slide off the trail and down the ravine into the pulsing river 1,000 feet below.

To save time, instead of eating lunch while the snow could get worse, we depleted the emergency stores of Snickers we’d packed. Wet, hungry, and drained, we arrived in the small piece of civilization called Manang and indulged in slice after slice of what tasted like the best apple pie we’d ever eaten.

A few days later, we prepared to cross Thorung La, the world’s highest mountain pass. Actually, we’d been mentally preparing ourselves to summit the pass since we elected the Annapurna Circuit as our trek months before. As the highest and riskiest point on the trail, our route required waking up at 3:00 am, climbing 3,000 feet to the summit before the winds could start and then descending 5,000 feet on the other side, all over eight hours of hiking.

In the moonlight as determined caravans of mules forced us to the trail’s edge, I struggled to suck in enough air even when standing still. Concentrating on our ascent through mounds of frigid powder, belabored huffing replaced our normal conversation.

At around 8:00 am, we triumphantly reached the prayer-flag-adorned summit marker at 5,416 meters (17,769 feet). Maximizing our 15 minutes on the pass, we formed a diamond shape between our bodies to conduct history’s highest ever game of Frisbee toss, pending approval by the Guinness Book of World Records, of course. Then, emboldened by our accomplishment, I gleefully skipped and slid down thousands of feet of soft snow alongside Krishna who was genuinely shouting a “weeeeee!” with each leap forward.

At our destination for the night below the snow line, we basked in the warmth of the lower elevation and consumed a day’s worth of meals in one sitting. I hadn’t felt such a sense of victory and relief in a long time. We had scaled the world’s highest mountain pass and lived to dine on a feast on the other end.

Overall, this exceptional adventure wouldn’t have been possible without my travel partners Caelan, Brian, and Ted. I’m grateful to them for handling the lion’s share of the trip’s logistics and for tolerating my gruffness through the cold, pain, and fatigue.

Most of all, thanks to our superb guide Krishna Adhikari who made sure we never came close to dying, and managed to do so while laughing with a grin permanently fixed on his face. Furthermore, Krishna’s selection of comfortable lodging, filling meals, and fun activities allowed us to focus on moving one foot after the other and relish in the unparalleled landscape. I highly recommend you contact Krishna if you ever want to visit Nepal.


“Dear Karim”—An Open Letter to College Students Struggling with What to Do with Their Lives

I was recently a guest speaker for a University of Washington entrepreneurship class that let me speak about my experience leading up to and during my time as an entrepreneur in Brazil. The following is excerpted and edited from an email I sent to a pseudonymized student from the class who asked me for advice.


Dear Karim,

I’m glad you enjoyed the class, and thanks for reaching out.

Before I continue, a disclaimer: I’m in the top 0.01% of the world in terms of opportunity as a healthy, white, upper-class, American man. Moreover, I’m fortunate that my family has always paid for my very expensive education, so I’ve never had student loans. I say this because, yes, your circumstances matter a lot, and I don’t know you, so I can only speak from my own experience. Nonetheless, following what I’m going to tell you, I’ve been able to at least support myself since June 2013 after my graduation.

I understand the stress you’re feeling now, probably much like many of your classmates. With a couple years of perspective since college, I can confidently say you actually don’t need to narrow down what you want to do with your life in your early 20s.

Those who do narrow it down now often end up telling themselves they don’t want certain things they’ve always wanted, or they just get so consumed by their new lives that they forget what it was they ever truly wanted. It’s okay to try lots of different things to see if you like them, if you’re good at them, if they’re good for the world, and if you can survive doing them.

Students who take it as dogma that you should have the rest of your life figured out by now are the ones most likely to rationalize themselves into comfortably numbing but less-than-fulfilling careers and lives. Most of my peers from college have fallen into that trap, and I know it’s hard to resist because family, friends, and society exert tremendous pressure on young people to follow conventional paths. I always felt suffocated by the banking, consulting, and Fortune 500 recruiting events at school because those companies do such a good job of convincing you that working for them will solve your problems and prepare you for the rest of your life.

Nevertheless, if you get a corporate job, you aren’t necessarily bound to get sucked in and live a rich but empty life. Moreover, you might even make a career for yourself in a company like Amazon or Microsoft that is both gratifying and pays well. Getting many honest inside references (especially from people who lack the incentive to recruit you) at different levels of a company is a good way to predict what working there would be like.

Since making a safe and fulfilling career is so difficult, I caution you against pursuing a soul-crushing, high-paying job in order to pay off student debt, save enough money for a business, travel long-term, etc. Even if your plan is to work such a job for only “a couple years,” I still caution you against doing so for the following reasons:

First, you’ll probably get accustomed to significantly more lavishness than you have in college. Your job where you work 60+ hours weekly will largely determine the friends you have, the activities you do outside of work, and even the most core principles you hold. Often, there’s novelty and fun in the “expense budget lifestyle” in the beginning. However, I know from close friends that the ensuing focus on fancy outings, expensive possessions, and high social status can quickly become bothersome and outright toxic.

Second, the more years you work in such a situation, the more commitments you’ll gradually acquire (long-term relationship, children, mortgage, etc.) and the less energy you’ll have. With more obligations, you’ll become more risk-averse because you’ll have higher costs in time and money to maintain those commitments. As such, it’ll be far harder to risk everything you have to follow an unconventional and uncertain passion that you’ve long dreamed about. On the other hand, you’ll much more easily adapt if you take the leap from being a poor college student to a poor entrepreneur or one of the first employees at a new company.

Starting my business was the hardest thing I’ve ever done, and I might have actually had to tolerate more bullshit in different ways than my peers in conventional careers. However, that 1% of the time (since it’s at least 99% dealing with mundane and agonizing bullshit) when I felt self-actualization for my achievements and impact was so rewarding that it more than made up for everything bad. Better yet, I probably left Brazil with more money in my bank account (~$35,000) from the business than many of my banker friends in NYC blowing their salaries on rent and bottle service. Now I’ve easily traveled the world for the past nine months while those bankers pull 100-hour weeks in anticipation of their year-end bonuses and next promotions.

In my case, to answer your original question of how I made my original decision, it came down to purpose and risk.

There was superior meaning for me in (1) learning more so than any other option I knew of by starting a business, (2) being in a place I loved–Rio de Janeiro, and (3) doing something that might benefit poor, marginalized favela families.

Furthermore, I knew I had very little to risk by failing–little money to lose, no debt, no wife, no children, and no dependent relatives. The worst case scenario was I’d gain an interesting story, learn a few things, and have to temporarily get a conventional job while plotting my next adventure.

Stay risky,



With a Little Help from My Friends

I’ve spent a lot of time by myself in the past couple years. While single-handedly starting my business in Brazil and traveling alone in Asia, I’ve found only extrinsic motivations keep me from reverting to my default state of internet-induced slobbery. Lacking face-to-face contact with friends, family, and mentors, it has been tough to gain the inspiration and motivation to better myself.

Fortunately, even when facing very different work and personal environments, three friends and I committed to holding each other accountable for our own self-improvement. Over two years, we’ve consistently set monthly goals together as a group and held monthly calls evaluating ourselves and each other’s progress.

This habit has been one of my greatest assets since graduating college, and I credit my accountability group with providing me important structure in my very unstructured life. I like to think we’ve combined forces to make ourselves and each other healthier, wiser, and more likely to fulfill our greatest ambitions.

With time, we’ve tested different components of our accountability group, but what follows is my view of what works well for us and might to do the same for you.


Find the Right People

None of this can function with the wrong group dynamic, so choose carefully.

Draft your friends. Tough love is a deciding factor in making the group function well. You should feel comfortable criticizing anyone in the group when she is slacking, and I’d cringe giving and taking criticism when the person isn’t a friend. Of course, you have to truly care about everybody in the group’s success to gain long-term reciprocal accountability.

Make sure there’s mutual admiration and a drive to stay respected. Because I hold each person in my accountability group in high esteem for his character and accomplishments, I want to impress them all. Simultaneously, I don’t want to embarrass myself among those I admire, which encourages me to meet my goals.

At a certain threshold of inaction, the group will disintegrate, so pick proactive and honest members. This phenomena has struck our group often and is the greatest threat to the group actually benefiting us: one person performs poorly and starts to slip on reporting progress, so the others lose motivation and do the same. Slacking will eventually affect everyone at some point, so the only defense is if at least one of us at any given time rallies the group, reports his progress, and pesters the others until they do the same.

The easy reaction to another’s inaction is more inaction. Thus, the only solution is consistent check-ins, even if you lose face by admitting weak performance.

Share some important commonalities. I’m not saying you have to be carbon copies of each other, and certainly being too alike could insulate you from unfamiliar ideas, backgrounds, and experiences. Still, everyone in my group is interested in social impact, business, and world travel and culture. Consequently, when I declare a monthly goal to arrange for myself three homestays with poor families, everyone in the group will understand my aim and give helpful feedback. My accountability group would be far less worthwhile if it instead were to comprise my other friends who don’t share my interests and aspirations.

Four people is the ideal number. While we initially contemplated expanding the group from the four of us, we haven’t discussed including others since then, probably because four people feels like the “Goldilocks” size. With pressing schedules, we can even struggle to pick an agreeable time and then conduct a meaningful call in an hour. More participants would just complicate an already difficult task. Additionally, having an even number lets us split into rotating pairs for more frequent check-ins, sometimes including sending daily priorities to each other.

Be in nearby time zones. From the beginning, my entire group has never been in one place, nor hardly even the same side of the globe. Even though we’ve quite consistently kept our accountability habit despite our distance, you’re stacking the odds against yourself by forming a group with far-flung people. It’s hard enough because a practice like leads to self-selection by those with time-sucking work and personal schedules.

In the best case scenario, at least occasionally replacing monthly calls with face-to-face gatherings can strengthen the group’s social pressure element. I’ve noticed both positive and negative reinforcement feel stronger in person than by phone. Just by traveling with two friends from my accountability group, it feels harder to escape from my monthly commitments.


Set the Right Goals

Since we began in 2013, our goals have spanned the realms of work, relationships, health, spirituality, finance, creativity, and beyond. As the point of our accountability group is to become better humans, no goal is off-limits, but don’t narrow your objectives to just one area. The group’s duty is to question and advise on each other’s goals, ensuring everyone focuses on what matters most.

These parameters seem to make our goal setting most successful:

Have one focused group call per month. We send out a Doodle poll to pick a call time a few days beforehand, and we each summarize our own performance on the past month’s goals in a group email before the call. Ultimately, our calls are most valuable when we don’t waste time recapping. Use calls to pose questions, challenge each other, and ask for and offer help related to your goals.

Set process goals, not outcome goals. The difference between the former and the latter is that a process goal is an action entirely in your control. However, an outcome goal depends on other people and circumstances, which you often can’t control.

For example, a process goal is to “email 10 new potential customers in a week” while its corresponding outcome goal is to “sell $5,000 of products in a week.” What if the company’s products you’re selling are unappealing to customers, and there’s nothing you can do about that? Setting that outcome goal and then failing to meet it might discourage you, when the failure was hardly your fault.

As such, process goals are more effective than outcome goals, especially when matched with persistence and experimentation. My logic is process goals only measure your own effort, so it’s harder to rationalize excuses for not completing them. Moreover, process goals force understanding of how you do something, which is necessary for you and your accountability group to change and improve your approach.

Choose quantifiable and easily provable goals. It’s difficult to hold yourself and others accountable for vague goals. For instance, picking the goal of “go to the gym” isn’t very helpful if your aim is physical fitness. Instead, try to “complete 4 sets of 5-7 repetitions of deadlifts, squats, and bench presses to muscular failure every Monday, Wednesday, and Friday.”

Better yet, it’s satisfying to send your accountability group a screenshot of that online course module you finished or a photo of you drenched in sweat after your run. At the same time, receiving this proof from others in your accountability group boosts social pressure for you to accomplish your goals.

Limit yourself to between one and three big goals per month. A greater number leads to you neglecting some of your goals when unexpected distractions and challenges inevitably occur. It’s easier to be able to remember each other’s few major objectives, so you don’t need to reference an old email before checking in on each other’s progress.


I hope our habit prompts you to see if group accountability can benefit you and your friends. Also, I’d love to know if anyone else practices something similar and how we can improve our process.

Above all, I’m grateful for my accountability group for their dedication to making me a better person and for their unwavering friendship. Moreover, thanks to Spencer Ingram for instilling a foundation of “less talking, more doing” in me during our weekly accountability sessions at HackCville in 2012-2013, which has formed the ethos of our group.


My Dirty Trick to Seeing the World

On the tarmac of the smallest airport I've ever been in Phongsaly, Laos

About to board a tiny plane on the tarmac of the smallest airport I’ve ever visited in Phongsaly, Laos

Disclaimer: The following applies to organized and responsible individuals who are American citizens or residents. Use this advice at your own risk.

Since inquiring about else’s finances can be so taboo, I relish in my friends’ discomfort when they ask me about mine. No, it’s not because I enjoy people having to excuse themselves to ask me, “How can you afford to travel for so long?” Though they might expect a response including the words “trust fund,” it’s exhilarating to reveal the truth that’s far from that. Better yet, it’s a little-known truth that changed my life and can change theirs.

The Basics of “Travel Hacking”

It’s called “travel hacking,” or using shortcuts to get free or nearly-free airfare, hotels, and other accommodation. Travel hacking is a lot less nefarious than it sounds, and it’s completely legal, even if the airline, hospitality, and banking industries might not like it.

Though travel hacking takes many forms, the most lucrative is applying for credit cards with valuable sign-up bonuses that you can redeem for flights, accommodation, and other travel expenses. In the year since I started, I’ve received 16 new credit cards with sign-up bonuses totaling over 700,000 miles and points across different loyalty programs. Better yet, I’ve used my earnings to fly from Brazil to Boston for $60, NYC to Miami in first class for $11, LA to the Philippines for $34, and many other places for pennies on the dollar. Along the way, I even stayed at a couple five-star Hyatt hotels for free! Oh yeah, and my credit score hovers between 740 and 800, which is well above average.

Whoa, whoa, whoa–hold up! Credit cards?! Certainly, your parents always warned you to be very scared of those dangerous pieces of plastic because they can wreck your finances. In fact, I agree with your parents, but only if you’re irresponsible and disorganized. What your parents probably didn’t know is that credit cards can give you the freedom to travel virtually anywhere in luxury on a budget, all while building your credit.

So, how does this all work? There are four straightforward steps:

  1. Apply for credit cards, starting slowly at first and spreading your applications among different card companies.
  2. Meet the minimum spending requirements, usually $500-$3,000 over the first three months to earn the sign-up bonus for each card.
  3. Redeem the sign-up bonuses for free or nearly-free flights, hotels, or other expenses.
  4. Shortly before the annual membership fees (which are typically waived in the first year) are due, cancel or downgrade the card to a no-fee version.

What’s the Catch?

First and foremost, you cannot carry a balance on your credit cards. To compensate for the big sign-up bonuses, banks attach hefty interest rates to their premium travel credit cards, and by paying this interest, you’ll negate your earnings. If you don’t trust yourself to pay your balance in full, then just don’t bother with travel hacking because it’s too dangerous.

Second, your reaction to the suggestion of opening and closing many credit cards was probably, “No way! That’ll ruin my credit!” In the very short term, the new inquiry on your credit report requested by the credit card company will likely ding your credit score 3 to 5 points (commonly on a 300 to 850-point scale). In addition, closing a credit card generally has a negligible effect on your credit score.

However, after three months, if you’re paying your balance in full and on time, your credit score will recover and rise because you’re creating a dependable credit history, which is the greatest factor in a FICO score. Still, if you’re seeking a car or home loan soon, for example, it’s best not to apply for too many new cards.

Finally, you’ll have to meet your cards’ minimum spending requirements, which requires actually making transactions. If you don’t think you’re able to spend thousands of dollars on credit cards, there are many ways around this. My favorite trick is making a trusted relative an authorized user on your accounts to make their spending count toward your minimum spending requirements.

Before You Start

Unfortunately, poor credit will make it difficult to gain approvals for the best cards, but everyone should have a firm understanding of their credit profiles, regardless of how good they think their credit is. Request free credit reports from the three major credit bureaus from AnnualCreditReport.com to verify your information is correctly cited. Even if you have late payments listed, it’s worth negotiating with banks to have these removed.

Next, you’ll need to pay down your existing credit card balances to almost nothing because 30% of FICO’s score is determined by your credit utilization. The lower your balances are as a percentage of your total credit lines, the better. At that point, wait up to a month for your payments to post and the card companies to report your new low balances to the credit bureaus.

Also, not having a solid plan of where you want to travel and when will make travel hacking less effective. Certain loyalty programs have far cheaper award redemptions and more award availability than others at specific times of the year for travel to certain regions.

Nevertheless, it helps to be flexible with your desired timing as peak travel dates might already be unavailable before you even decide you want to go somewhere. Similarly, don’t expect to sign up for cards today and travel tomorrow–in most cases, you’ll need at least three to six months from when you apply for a card to when you begin your trip.

Some recommended cards to start with because of their flexibility, waived annual fees, other perks, and reasonable minimum spending requirements are the Barclay Arrival Plus and the Chase Sapphire Preferred (my referral link). These were both some of my first travel hacking credit cards, and they’ve allowed me to go on some unforgettable trips.

I’m happy to give my friends specific advice on which cards to apply for and overall strategy, but I need to know more about your specific travel goals and habits. For introductory travel hacking tips, I recommend the blogs Million Mile Secrets, Frugal Travel Guy, and The Points Guy.

If money is your biggest barrier to seeing the world, travel hacking might be your ticket to freedom.