by Anastacia Gordon

I’m a writer, backpacker, (former) early-stage startup employee, (future) business school student and aspiring investor interested in consumer tech, music, media, and culture. This site originally served to document my first 10-day solo backpacking trip through Thailand (First Saga). I then moved on to documenting my unconventional experiences in the professional world, as the first employee at a now venture-funded startup called Jopwell (Y Combinator S’15) (Second Saga). Today, I write about whatever interests me in the business of music, media, and tech (Third Saga). Here’s to finding peace of mind and sharing a little piece of mine…

Jump to:   The First Sage  The Second Saga  The Third Saga  Contact Me  

99 Problems & Purchasing Concert Tickets is 1

Fact: Jay-Z is one of the most revered artists of our time.

Fact: Jay-Z has announced upcoming headlining performances at Philadelphia’s Made In America Festival, Queens’ Meadows Festival, Austin’s ACL Festival, and the UK’s Virgin V Festival.

Primary inference: Jay-Z is going on tour sometime this year, or next year.

Secondary inference: I probably won’t be able to get tickets to any of the shows in my city.


How can I be so sure? Because the same thing happens every year. One of my favorite artists drops a new album, announces a global tour, and provides a code to a limited presale ticket event happening the next day. My friends and I immediately head to GroupMe to share excitement about the tour and get to work on planning our elaborate ticket purchase strategy. “I’ll take the American Express presale, you take Citi, you do LiveNation and if those fail, we will all attempt to secure tickets during the general sale.” We set reminder alarms and timers for the final minute before the sale…59…58…57…Everyone opens Ticketmaster on multiple web and mobile browsers…25…24…23…Some of us aim to buy tickets for the entire group, others aim to make multiple purchases in smaller blocks of two or three tickets…12…11…10…Regardless, we all anxiously wait in formation, trigger/Twitter finger at the ready to find and purchase tickets…3…2…1…*CLICK*

Error – Unfortunately tickets matching your criteria could not be found. This event is sold out.

Image result for blinking gif       Image result for how sway gif

The Problem

Purchasing concert tickets has seemingly become more difficult than winning the Powerball. According to a report from the office of New York State Attorney General Eric T. Schneiderman, almost half of the total tickets available within a venue are usually reserved ahead of time and not made available for purchase by the public. Artists, promoters, credit card companies and others reserve these tickets for themselves and their contacts, or for presale events to cardholders. On top of that, it’s been estimated that as much as 60 percent of the most desirable tickets for some shows are purchased by bots or software programs that automate the ticket-buying process. So as sophisticated a ticket-buying operation as my friends and I run, we, like millions of real fans, barely stand a chance. In 2016, the State of New York was forced to take legal action, declaring it illegal to use computer software or computer-enabled devices to buy and resell tickets to concerts and sporting events for a profit. Offenders will be charged with a misdemeanor, punishable by up to one year in jail. Those who knowingly resell tickets purchased by a bot risk a fine between $500 and $1500. The federal government later got involved, passing the Better Online Ticket Sales (BOTS) Act making the use of ticket bots illegal across the country.

Unfortunately, however well-intentioned, these laws will do all but nothing to make the act of purchasing tickets any easier for consumers — the same way fines and laws didn’t stop people from illegally downloading music. Entire businesses, like Stubhub and SeatGeek, exist to structure and service the secondary ticket market, estimated at $5bn in 2015 by Northcoast Research. Demand will continue to far outweigh supply especially if artists like Jay-Z keep artificially limiting tickets available to the general public. Do you remember Jay-Z and Justin Timberlake’s Legends of the Summer Tour in 2013? Roughly 70% of tickets to each of the two sold-out shows at Yankee Stadium were reserved for presale events, the same sales heavily targeted by bots eager to secure the best tickets ahead of the general public. In artists’ bid to guarantee as much profit via ticket sales as possible ahead of any given show, the average consumer will continue to get the short end of the stick when it comes to reserving tickets directly from the merchant on their own.

A Solution
RobinI recently came across Robin, a startup founded in 2016 that serves as a personal concierge for securing tickets on behalf of concert and event-goers – even before events are announced and tickets go on sale. How? Robin has yet to reveal that piece of its formula. But if I had to guess, I’d assume Robin is building its business model on partnerships with artists and concert promoters or ticket vendors, like Livenation and Ticketmaster, that provides the company early access to a certain number of the tickets already being set aside ahead of sales to the general public.

The platform definitely benefits the most loyal fans who always support their favorite artists when they’re in town. It also benefits artists who want more of their tickets in the hands of actual fans. Although reservations are limited to four tickets, which hampers the “ticket farming” functionality of bots, and makes the platform less attractive for infiltration by a large-scale bot operation, predators could still easily take advantage of the platform. Robin does very little to verify that account-holders are real people. During signup it asks for a phone number to send updates to, but I merely skipped the step upon realizing it was for communication as opposed to verification. Later it prompted me to connect my Spotify account in order to generate recommendations for artists whose shows I’d want tickets reserved for in the future, but I was able to skip this step too.

On top of that, there is an obvious ceiling to the business. At scale, the platform becomes less valuable from a consumer’s perspective. For example, Jay-Z has millions of fans in New York. There will come a point in the company’s growth where it just won’t be able to guarantee all of its account-holders early access to tickets by choosing their favorite artists. Demand will eventually outpace supply and the company will need a new value proposition to retain and attract users. Although, Robin is a convenient tool to assist consumers in operating within the current landscape, it does very little to change the landscape itself and address the root issue of ticket re-sellers using bots to secure tickets at face-value ahead of actual consumers in attempt to exorbitantly markup ticket prices and resell these tickets to these same consumers.

THE Solution

A true solution means eliminating ticket arbitrage entirely by directly controlling the price of each ticket. This would effectively eradicate any semblance of a secondary market, thus, leaving those interested in buying and selling tickets for profit with no option to do so.

                No automatic alt text available.                 GUTS

Two European startups, LAVA and GUTS, currently leverage blockchain technology to do just that. Remember, where there is technology, there is a way!

By now you’re probably thinking OK this is great but – what is blockchain exactly and how could it help fans get tickets to the next Jay-Z concert without being forced to pay extremely high prices on the secondary market?

In short, it’s a type of technology that allows digital assets to securely, but transparently, trade hands without the need for a central regulatory body because the transaction is verified and recorded by all parties in the network. People can easily create, copy, alter and distribute certain physical assets on the internet because we live in a digital age. This creates a need to process online transactions between people through trusted third-party sources who keep master records. With blockchain technology however, because multiple records of any given transaction get distributed throughout the blockchain network, everyone essentially becomes a record-keeper which makes falsifying transactions almost impossible. A central governing body to verify transactions becomes unnecessary and individuals can freely and directly exchange things online with each other.Consider this using our ticket example: oftentimes when you buy a ticket online, sellers issue a digital copy of a paper ticket – like a PDF document. The owner can copy this document multiple times and sell copies of the same ticket to multiple people. The owner can choose to sell these (fake) tickets for less than she paid for it, for more than she paid for it, or for the same price. No one would know until it’s too late. Integrity lies completely at the discretion of the owner.

Secondary ticketing platforms like StubHub and Seatgeek protect against fraud in the first instance by fining sellers who distribute fake tickets and/or by blocking them from selling tickets through the site in the future. This threat alone dramatically reduces instances of fraud on these platforms since resellers need access to a market of buyers to liquidate their ticket holdings.

Issuing smart tickets using blockchain however, would eliminate this possibility entirely. The technology prevents individuals from duplicating tickets issued through these platforms because each “block” or record of a transaction is immutable and public. Anyone wanting to change the record for their benefit, would need to change them all, which becomes impossible at scale. That said, if ticket prices were hard-coded into these records too and ticket were only transferrable through a blockchain enabled platform, owners wouldn’t have the ability to sell fake ones or alter the face value of the ticket prices should they decide to transfer ownership and resell them in the future.

The Point

If people can’t alter ticket prices because tickets are only issued on blockchain-enabled platforms, then there is no opportunity to buy low and sell high, and thus no marketplace. No marketplace means no profits and no reason to create bots that purchase tickets for popular shows as quickly as possible. The only three things that would stand between me and my Jay-Z tickets are other real fans like me, the internet speed in my home, and a well-timed Twitter/trigger finger.

Genius, I know.

Whoa GIF - Jayz Clapping Whoa GIFs

Royalties. Royalties. Royalties.

About three weeks ago, Kendrick Lamar released his highly anticipated third album – perhaps one of the most highly anticipated hip-hop projects of 2017. DAMN. explored themes of religion, love, Black pride, police brutality, and perseverance in the face of institutional racism. Heavy. But very well received.

DAMN. sold 603,000 equivalent album units in its first week, the second highest debut for an album since Drake’s Views sold over a million in the first week in 2016. It also claimed nine of the top ten songs for the week of May 6th on Billboard’s On-Demand Streaming Songs chart, which tracks streams on platforms like Spotify, Apple Music, TIDAL, and more. Kendrick one-upped previous record holders, Drake and J. Cole who each concurrently held the top eight spots with songs from More Life and 4 Your Eyez Only, respectively.

Such a stellar body of work only exists via a meeting of the greatest minds. A look at the album credits reveals beats from heavy-hitter producers like Mike Will Made It and 9th Wonder, guest features from world-renowned artists like U2 and Rihanna, and an average of three writers per song.

With all those collaborators, digital distributors, and samples, it’s easy to see why lawsuits about unpaid royalties have riddled headlines over the past few years. Just last month, Spotify reached a $30m settlement on a $150m class action lawsuit filed against the company in 2015 over unpaid royalties. Having learned its lesson, Spotify announced its acquisition of Mediachain just last week. Founded in 2016, Mediachain is building a more efficient way to link music files on the internet (in this case, on Spotify) to its owners and creators so that they can easily and accurately receive payment for the money generated from streams on the music platform.

In the wake of these cases, plenty of other startups have popped up as solutions to the issue. I’ve been following three that I believe are particularly poised to define the space and lead the charge:

  1. Founded in 2015, Stem is an online platform that distributes music to streaming services and organizes the royalties associated with each play for the contributing artists. The company is off to a great start, already partnering with the largest streaming platforms: Apple, Spotify, SoundCloud, and YouTube. They are currently working on expanding that catalogue of partners to include Pandora, Google Play, Tidal, and more. Last year, Frank Ocean put the service on the map when he distributed his surprise album, Blonde, through the service. What makes Stem special is that it bundles distribution with royalty accounting, which is typically hard to come by for independent artists not supported by the robust infrastructure of a record label. Collaborators must agree on a royalty split, upload their own metadata (unique attributes embedded in digital music files used to identify the content, its owners, creators and contributors), and choose the streaming services where they’d like to distribute their content. From there, Stem receives the streaming and revenue data from each service and using its proprietary algorithm, uniquely packages this data and displays it in a comprehensive dashboard for all contributors. The service distributes music for free, but takes a 5% share of the royalties. With the rise of social media and independent artists like Chance The Rapper making history for his Grammy nomination and win in the Best Rap Album category for his streaming-only album, Coloring Book, the indie route seems more conquerable than ever.

Fun Fact: Of the three founders, one is a woman.

  1. Also founded in 2015, Jaak connects media to content metadata in order to improve the licensing and royalty payment process for creators, collaborators, and distributors. Discrepancies inevitably arise when various sources including artists, publishers, record-labels, and streaming services keep their own records of music ownership and royalty payments. Even seemingly inconsequential differences in the written identity of an artist can lead to incorrect records and payments. For example, Jay Z, Jay-Z, Hova, and Jigga might be the same person in real life, but individual records might exist for each variation of his name. Jaak leverages blockchain technology to maintain a metadata network that allows various parties to easily and quickly communicate between each other, and at the very least, keep records using the same metadata. This ensures creators are more reliably compensated for the use of their content, and that the people and organizations using the content can more easily and reliably find and license it without fear of monetary retribution at some later point in time. This is the first step to dramatically improve the process of content licensing in today’s digital media space.

Fun Fact: Jaak was selected as one of the startups in Techstars’ first batch of music startups. Also, of the three founders, one is Black.

  1. Founded in 2016, DotBlockchain Music also seeks to leverage blockchain technology, but to develop an entirely new music format (to replace the MP3 and others) that along with the actual music will hold immutable metadata like ownership history, terms of use and licensing restrictions all within the same file. Since metadata is rarely standardized and easily corrupted or deleted, as described above, DotBlockchain hopes that popularizing this new file format will allow the industry to circumvent the issue altogether. Additionally, as ownership changes and payments are made, a transparent record of these transactions would remain with the file for all to see. DotBlockchain recently announced partnerships with four industry groups, a performance rights organization, a publishing royalty administrator, an indie music distributor, and a digital rights service. These partnerships give DotBlockchain approximately 65 million songs that it can use to begin building out its solution in the marketplace.

The fourth industrial revolution is upon us and I’m super excited to see how these companies go on to permanently shape the music industry and much more.

Virtual Reality & The Music Industry

Last September, during Labor Day weekend, I found myself stuck at home and unable to join the annual pilgrimage to Philly to partake in Budweiser’s debaucherous 2-day Made In America music festival. Let’s blame it on the fact that I was deep in the throes of a personal project, and ignore the fact that large swaths of people secretly give me anxiety. It was a beautiful long-weekend too. Savoring the last bits of summer and eighty-degree weather with my friends on Ben Franklin Parkway, cocktails in hand, near my old stomping grounds, would’ve been nothing short of bliss.

To add insult to injury, I’d be missing Rihanna’s headlining performance! The concert was on the heels of the 75-stop world tour for her eighth album, ANTI (hands down the best album of her career, and one of the best albums of 2016—don’t debate me). I saw her crush it at the New York stop earlier in the year, so I was even more depressed about missing the show. Stressed, I miraculously remembered my free Tidal subscription, and that the platform always live-streams the festival! At 9:23pm, two minutes before her performance, I scrambled to pull everything up on my AppleTV right as the beat dropped for her opening song. I LOST IT. And over the next hour and a half had the time of my life in the comfort of my apartment.

Only one thing would’ve improved that in-home experience—watching the concert in 360-degree video via a virtual reality (VR) headset.

The music industry as we know it is collapsing, that’s no secret. The digital age has altered the way people consume music. Social media and online streaming services have democratized marketing and distribution. Consumption is instantaneous, and often free. It is also increasingly immersive. Did you miss How Beyoncé perfected the ‘visual album’ with ‘Lemonade’ or Trey Songz revealing his new dating series is just a marketing ploy for his album #TremaineTheAlbum? Given these trends, the rise of VR technology presents an excellent opportunity for artists seeking to create new experiences for their fans while earning alternative sources of income, especially amid depreciating album sales and paltry streaming royalties.

VR has been around for quite some time, but it predominantly lived in the context of the gaming industry. However, we can thank Facebook’s 2014 $2bn acquisition of Oculus VR, then only a two-year-old company, for breathing new life into the technology. The enormous purchase price caught the eye of many, including leaders outside of the gaming industry. For the first time, they too began investing in and re-imagining the innovative possibilities and applications of VR in diverse, “nontraditional” contexts. A few years later, the music industry is slowly catching on.

As a prelude to ANTI, Rihanna signed a $25m partnership with Samsung to promote its brand and its GALAXY products, sponsor her tour, and “tease” the album to her fans. Together they unveiled a mobile website, a mobile game app, and a series of videos in the months leading up to the album release. Dubbed ANTIdiaRy, the project allowed fans to intimately explore a series of virtual rooms (blending VR and 360-degree video technology) representing various stages of Rihanna’s life to find clues and unlock pieces of her story and ultimately, her new album—right from their Samsung smartphones.

Note: It’s easy to conflate VR and 360-degree video. I’ll spare you a wordy explanation and instead point you to the graphic below that quickly sums up the differences. Industry vets are keen on the distinction, but I think from a consumer’s perspective, the experiences might as well be one and the same—just different points along the same spectrum.

Looking back, Rihanna attempted an incredibly ambitious and innovative approach to energizing fans for her album release through emerging technology. ANTIdiaRy was a testament to the opportunity for artists to provide more dynamic and interactive content to their fan base, while capitalizing on sponsorship income.

Going forward, we could see other revenue opportunities emerge as VR and 360-degree video technology is monetized via pay-per-view, subscription, and ad revenue models. Partnerships with companies leading the VR/360-degree video charge will play a key role in allowing artists to leverage the technology to create immersive experiences, market their projects and further distribute their music and live performances to fans.

Remember Dawn Richard from Making The Band III, who punched Aubrey O’Day in the head, and ruined what was left of Diddy’s beloved girl group Danity Kane? Well, she has been flourishing as an independent artist for some time now, and was among the first to experiment with VR content for her fans. Richard teamed up with VR Playhouse in 2016 to record and release a VR music video for her song “Not Above That,” which had previously reached the top spot on the iTunes electronic chart. Dawn was also the first to live stream on Youtube’s 360 Live platform, teaming up with the company to launch its new product with a 30-minute mini-concert performance.

Media and entertainment companies are following suit in collaborating with artists to bring VR content to the masses. Live Nation has already committed to the space, partnering with Citi and NextVR to produce live VR concerts for the bank’s rewards card members. Live Nation has also partnered with Lil Wayne and Major Lazer to provide fans with an intimate look at their lives and careers via its “On Stage” VR docu-series airing on Hulu’s VR app.

Although ANTIdiaRy gave us a positive look at what a multi-platform VR experience could look like for artists and fans, social media reminds us that the project was actually met with more confusion than acclaim. It’s a prime example of technology outpacing consumer behavior. It made a splash among her superfans for sure, but everyone else either didn’t have a Samsung phone, or just wasn’t ready to appreciate it and fully engage. 360-degree video and VR have a long way to go before mainstream consumers adopt them. For one, affordable headsets and a library of content primarily stand in the way.

Fortunately, a welcome byproduct of trendsetters like Rihanna and Dawn Richard experimenting with the technology is the creation of the robust content pipeline needed to drive its mainstream exposure and adoption. Additionally, the efforts of companies like Google to constantly improve the audiovisual experience, while manufacturing headsets at a more affordable price point, means the barriers between consumers and mass adoption will slowly continue to crumble. It’s only a matter of time before your favorite artist decides to ride the wave too.

We’ve seen Beyoncé reset the bar for musical experiences time and time again not only with her theatrical performances, but also with the release of two visual albums in the last three years. She still somehow fell short of Album of the Year at the Grammy’s both times. Since her best isn’t good enough, it’s clear that her next project has to live in an alternate reality to receive the critical acclaim it will likely deserve. She literally has no other choice. #BeyGreat 2018: The VR Experience? Perhaps. Don’t sleep—I know I won’t!

The Podcast Wave: Why Creators, Entrepreneurs, Investors, and Advertisers Should Pay Attention

If you know me, you know I LOVE podcasts. I’m like a kid on Christmas just waiting to unwrap her presents when a new episode drops from one of my favorites each week. I started listening in early 2014 when a friend of mine launched a show centered around girl talk. Around the same time, Serial was becoming popular and I needed to understand how in the world Adnan managed to get himself in that entire predicament in the first place. From there, my appetite kept growing. I primarily subscribed to shows recommended by friends focused on subjects like hip-hop, media, tech, entrepreneurship, leadership, and the all-encompassing, nebulous, “life.”

Today, I subscribe to about 20 podcasts and I know at least four people in my extended network who have their own podcast or are in the process of launching one in the near future. Being the nerd that I am, the emergence of podcasts among my peers piqued my curiosity, and convinced me that if the medium was on the rise on a micro level, the same had to be true on a macro level as well. I went in search of the bigger picture and dug up some really interesting research that points to podcasts as a bubbling market opportunity for creators, entrepreneurs, advertisers, and investors. I summed up the trends and my thoughts below.

Who listens to podcasts (besides me and my cool friends)?

According to The Podcast Consumer 2016 published by Edison Research:

educated, affluent, millennial males.

  • 56% are men
  • 38% are 18-34 (34% are 35-54)
  • 41% have a household income above $75k
  • 51% have a four-year college degree, some grad school or an advanced degree

Growth is good, but how fast?

screenshot-2017-03-01-01-59-32Growth in the awareness of podcasts jumped 12% in 2016, the largest jump since 2009 when awareness increased by 16% from the previous year. Additionally, monthly podcast listening increased 24% in 2016 and 75% since 2013. Weekly podcast listening increased 30% in 2016 and 86% since 2013. Of the people who listen to podcasts weekly, 79% of them listen to five or fewer per week. On top of that, podcast advertising revenue had been rising at annual rates of 20%, but in 2015, that rate more than doubled to 48%. To top it all off, ad sales totaled $167m in 2016 and are estimated to grow 24%, reaching $207m in 2017.

How and where are they listening?screenshot-2017-03-01-01-45-31

The devices being used to listen to podcasts are shifting quickly. In 2016, 71% of people listening to podcasts used a smartphone, tablet, or other portable device. In 2013, that number was only 42% and the rest accessed podcasts through computers. People mostly listen to podcasts at home (53%) and in the car (21%).

What it all means: The industry is expanding quickly, but there is still plenty of room to grow. We live in the age of on-demand binge consumption. Netflix, Hulu, Spotify, Apple Music et al. truly ushered in a new era of behavior and podcasts fit right in It makes perfect sense why more and more people are being drawn to the medium. Looking forward, three things stand in the way of mass adoption and consumption:

  1. Growth in mobile device ownership and adoption. We’re sure to see an increase in podcast listening well into the future as mobile phones and portable internet-enabled devices continue increasing in ubiquity. Gone are the days when people needed an iPod, or needed to be at a computer to listen. Additionally, with the impending rise of connected cars and smart devices like the Amazon Echo and Google Home, podcasts will become even easier for less tech savvy consumers to access at existing points of popular consumption, setting the stage for continued growth in podcast listeners and increased listening habits among current listeners. It’s simple: people tend to adopt things more quickly when they are easier to access. screenshot-2017-03-01-01-44-13
  2. Discoverability, shareability and searchability. Distribution remains a challenge. In order for mass adoption to occur, and for the total audience to grow beyond the current 58m monthly listeners, not only do podcasts need to be even easier to access, but finding podcasts of interest also needs to be easier. 11% of podcast listeners are 12-17 years old and 17% are 55 and older. There is plenty room for adoption within these age groups, but tapping into them means access to a more comprehensive library and better recommendation tools for similar shows based on my listening habits and interests. Think Spotify Discover Playlists and Apple Music recommendations. Podcast networks like Gimlet, NPR and the Loud Speakers Network are trying to do just that, but there is still a long way to go. Additionally, in today’s social media driven society, a more integrated platform that allows listeners to interact with podcasts, react and share audio snippets or comments at specific moments, would also go a long way in cultivating loyalty, engagement and referrals. Cross-pollination is key. As a podcast listener, I can also say that being able to search audio the audio files for specific words would also go a long way in helping me digest the content and share specific pieces of conversation to friends. Luckily, Popup Archive and Clammr already seem to have a head start on addressing these needs.
  3. Efficient monetization, measurement and analysis tools. The podcasts I listen to sell native ads to brands targeting the show’s listener demographic. A marketplace that helps pair brands with relevant podcasts is imminent. Art19 already allow podcast hosts to insert ads at optimal points of the show. There is surely more innovation to come to streamline monetization. At one point, I convinced my team to experiment with podcast ads. The problem for us, was that as a very young startup that offers a service (as opposed to a product) we didn’t have the tools in place to measure the impact of said ads. On top of that, concrete dollars saved on a product is a whole lot more of an incentive for new users to “site their source.” Had we been able to digitally track referrals on our end and easily compare that against podcast engagement stats, we might have been more committed to the medium as an effective advertising channel. Anywhere from 60%-65% of podcasts are downloaded through Apple, but the company provides almost no data on engagement. For example, show hosts know how many downloads they get, but not how much of the episode people listen to. This has to change in order for companies large and small to continue cutting more checks and larger checks for ads. Apple is currently asleep at the wheel, but that leaves the door wide open for innovators.

That said, the future is bright for all parties involved: creators, entrepreneurs, investors, and advertisers. I’m so excited to see how the industry develops over the next few years. Now is definitely the time to dive in. Don’t let me say, “I told you so!”

P.S. – Check out a few of my favorite* podcasts below:

  1. hibtHow I Built This – “A podcast about innovators, entrepreneurs, and idealists, and the stories behind the movements they built.” Favorite Episode: Cathy Hughes on Radio One
  2. atygAnd Then You Graduate -“Discussions and interviews on what comes after following all the rules.” Favorite Episode: Marisa Mendez: How to make it in the Radio industry
  3. btcBE The Code -“Spotlights on the most influential blacks in technology – from celebrities to financiers – and how they are reshaping the industry, with their unique perspectives.” Favorite Episode: Marlon Nichols, General Partner, Cross Culture Ventures
  4. bgpBlack Girl Podcast – “From the POV of 5 black women in the entertainment industry. Candid, hilarious, painful & raw.” Favorite Episode: Pain
  5. tcjsThe Combat Jack Show – “The undisputed #1 HipHop podcast, the Combat Jack Show features interviews with HipHop icons & the most in-depth conversations about music, news, culture & race.” Favorite Episode: The Foxy Brown Episode
  6. tsbsThe Series B Show – “Brandon Jones highlights the journeys and ideas of top influencers in tech, business & culture via one-on-one in-depth conversations.” Favorite Episode: From Unpaid Intern to Fashion & Beauty Powerhouse – The Kahlana Barfield Brown Episode – Part 1 & Part 2
  7. mgrhRevisionist History -“Reinterpreting something from the past: an event, a person, an idea. Something overlooked. Something misunderstood.” Favorite Episode: Carlos Doesn’t Remember
  8. wsjWSJ Media Mix – “Lively analysis, timely insights and in-depth interviews, the covering the fast-changing media and marketing business.” Favorite Episode: Snapchat’s Pre-IPO Ad Sales Offensive
  9. hbrHBR IdeaCast – “A weekly podcast featuring the leading thinkers in business and management from Harvard Business Review.” Favorite Episode: Negotiating With A Liar
  10. tccThe Casey Crew -“DJ and radio host DJ Envy and his wife Gia Casey will explore the good, bad, ugly and beauty of relationships and family.” Favorite Episode: Did Chrisette Michele’s Fiancé Agree With Her? A Conversation With Chrisette and Biggs

*Please reserve your judgement. I am dynamic and skilled in the art of code-switching. I frequently indulge in a variety of high and lowbrow interests. Lol.

Going Fast & Far: Notes on VC Fundraising – Pt. 1

*Note: I’ve only barely scratched the surface with this post. There is A TON of other things to keep in mind when fundraising, but I’ll cover that in more detail in a second post – part 2. Until then, enjoy part 1 and stay tuned!

There is a famous African proverb that says, “If you want to go fast, go alone. If you want to go far, go together.” For a person who sometimes despises relying on other people, this quote often provides great perspective on what can be accomplished with a little patience and a little teamwork. I recently started wondering how I could apply this to the context of Jopwell. Unfortunately, the dichotomous nature of the proverb posed a huge problem. As a newly minted startup team racing to build a billion dollar business, the proverb offered no advice for going fast AND far at the same time.

“If you want to go fast, go alone. If you want to go far, go together.” – Unknown

Luckily, experience is a great teacher when African proverbs fail. In Jopwell’s short life, we have discovered that going fast and far requires two things: mentors and venture capital. This post will focus on the venture capital part of the equation.

Have you ever wondered why very successful companies like Uber still raise billions of dollars in funds? It’s because one of the most critical aspects of a startup’s growth process, or ANY business’s growth process, is raising money. Access to extra capital allows companies to keep growing, or to go farther in their quest to dominate the market, at a faster rate than would normally be possible through organic means, relying solely on their own profits.

When I first joined Jopwell, I was extremely fascinated by the process of getting people to invest hundreds of thousands to millions of dollars in early stage companies. I remember my uncle telling me when I was little, “There’s so much money out there, you don’t even need your own to start a business anymore.” My teenage self merely thought, “Really? Where??” I had no idea at the time that what he was teaching me about was venture capital. Come to think of it, I don’t think he knew what he was teaching me about either. These things just didn’t happen in our Jamaica Queens community or in the black community in general, as far as we knew. I had only read about companies raising venture capital in this mythical place called Silicon Valley via newspapers or saw fictitious deals go down on television. The only way I saw people in my community start businesses was by going to a bank and applying to take out a loan.

Today’s booming tech world however, has created a very real and very large marketplace for wealthy people (angel investors) and companies (venture capital firms) to invest in early stage companies through venture capital (VC) funding. Michael Seibel, who co-founded and Socialcam which each sold to Autodesk Inc. for $60m and Amazon for $970m respectively, made headlines last year when he was appointed as the first Black partner at Y Combinator. He has been an amazing resource to Jopwell as we work to get this thing right. The Jopwell team recently attended a Black entrepreneur showcase event in San Francisco where Michael provided some excellent insight into what exactly it is that Y Combinator and VC investors look for when investing in early stage companies. Having been at Jopwell through it’s initial $1,000,000 raise and through the Y Combinator application process, Michael’s points couldn’t have rung more true. For budding entrepreneurs, those who have applied to YC or the fellowship program or those who are going through their very first round of funding, from a very high level, VCs typically look for a few basic things:

  1. A fully committed, well-connected team with technical talent. – You have to be working on your business full-time. Let’s be clear. No one wants to commit boatloads of their money to you to build the next great company, if you can’t commit all your time to building it. Investors don’t want to hear that you are working on your idea “on the side.” Booming businesses aren’t built on the side. They are built from hours of hard work and complete dedication. Your commitment level is a signal to investors; one you can control. I know, it sounds like a catch 22. You can’t quit your day job and focus on your company full-time without funding, but you can’t get funding without quitting your day job to work on your company full-time. We’re all adults with bills and responsibilities that make working without income difficult, if not impossible. Porter and Ryan were extremely fortunate to have worked in finance prior to taking the big leap. But even without a finance salary anyone can start small, save and budget. It’s definitely not that simple, but it’s a start. Entrepreneurship is a test of earnestness. I also hinted at this a bit in my first post about what swayed me to join the company. But the composition of the team is extremely important. Not only does the team have to have had experience with the problem the business is tackling in some capacity, but the team members also have to have a certain level of trust and rapport with each other that comes from years of friendship or a meaningful shared experience. When building anything from scratch, things change, people disagree and things get messy. However strong existing relationships means the group likely already knows how to work with each other and play off of each other’s strengths and weaknesses or they can bounce back when things do get messy. Last but not least, investors place a huge emphasis on the presence of developers. If you’re building a tech platform/solution you can’t outsource the development of your platform forever. It’s expensive and you eventually won’t be able to guarantee consistency. Find a technical co-founder.
  2. A business that targets a HUGE market – think billion$. Different investors are looking for different sized businesses. But all investors are in it to make money. They want to see that you are solving a huge problem so that they stand to get a piece of a huge check. It’s that simple. Everyone in the tech world is looking for a billion dollar market opportunity, the Airbnbs, Snapchats and Ubers of the world, but multi-million dollar markets mean profits too. Not all successful businesses play in billion dollar markets.VC is a high risk, high reward game. 90% of startups fail, so it makes sense to attempt to maximize returns by backing companies solving problems that serve a really large market. This way, there is at least a chance to eat a small piece of a huge pie.
  3. A company that doesn’t need money. – Raise money before you need it. But if you are raising money when you need it, act like you don’t. When it comes to investing money, there’s just something more comforting about being wanted rather than being needed. No investor wants to hypothesize about why you need money so badly. You know how they say start looking for a job when you don’t need a job? This is the same principle. Not needing money or at the very least, acting like you don’t need money gives you leverage to set or negotiate terms. You always want to be negotiating from a position of power. Investors often have way more than money to offer, like connections to people or companies that will help you grow your business. If you don’t need money, then investors will likely bring all those additional things to the table as well. From there, you can create a marketplace for yourself. After all, economics shows us what happens to prices when heavy demand meets limited supply.

Startup Lessons 101

Jopwell was selected as one of 96 teams from a pool of 6,000 to participate in the Summer ’15 class of Y Combinator, the preeminent accelerator program for startups. On June 1st, our team packed up and moved to San Francisco, California for the duration of the program. We live and work out of our apartment, in which we somehow manage to fit 9 people. It has been an absolutely amazing experience. The work never stops, but neither does the fun nor the learning. Some common themes have arisen over the past 10 weeks that I think any innovator or budding entrepreneur might find interesting…

  1. Do things that don’t scale. – Sometimes, the best practices that end up defining a company’s brand, strengthening its relationship with its users and ironically helping it grow, aren’t sustainable long term. However, these practices are still critically important to the success of a company. AirBnb is an amazing example of this idea. In the early stages of the company, the two co-founders participated in Y Combinator and also moved out to the San Francisco Bay Area, like the Jopwell team did this summer, to participate. The program consists of mandatory founder dinners and office hours with YC partners, scheduled at each team’s discretion. In between these required events, founders and their teams are expected to work on growing their businesses nonstop. For AirBnb, that meant frequently flying all the way back to NYC (where they saw the most business) to go door to door to recruit new customers and helping existing ones improve their apartment listings by taking high quality photographs of the space themselves, on behalf of their customers. This was no doubt a very expensive, tiring and time-consuming practice. However, this “white glove” service and dedication to “doing things that don’t scale” not only drove the activity on their site, but it also allowed them to directly connect with and learn from their customers, increase customer satisfaction and ultimately lay the foundation for the strong brand of trust it is known worldwide for today. The AirBnb founders did whatever they needed to do, no matter how unsustainable, to ensure their users were finding success via their platform and that has made all the difference. Jopwell practices this same principle on a daily basis to ensure that our candidates are finding opportunities specific to their skills and interests and that company users are finding ideal talent for the roles they are seeking to fill. No matter what it takes, our end goal is to satisfy both of our customers.
  2. Think long-term greedy. – One of the main differences between start-ups and large corporations is the scope of their focus. Large corporations have whole strategy teams that plan the entire company’s future over the next 5 years. Whole departments and products hang in limbo, paralyzed without specific forecasts and timelines. Early stage start-ups are on the opposite end of the spectrum. Our goal is always the same: get through the day ahead. We don’t know if we will be around tomorrow, in a week, in a month, or much less in a year so we are perpetually focused on executing in the short-term. This isn’t to say that start-up founders and their early-stage employees lack vision. It just means that we often prioritize the ‘right now.’ That is the difference between whether we make it far enough to even be able to execute on the long-term vision or not. When pushing new features, we focus on the most immediate needs of our candidates and company users, as opposed to the bigger plan we have in store. Every so often, we must remind ourselves to be “long-term greedy” and look at the bigger picture. For example, sometimes our sales team faces the choice between locking down a partnership for a contract with less than ideal figures and belaboring the negotiation in hopes of landing a bigger deal. It’s important to remember that building a successful business for years to come is about winning wars, even if that means losing a few battles along the way. If you find yourself in a less than ideal negotiation position, try to decipher the battle versus the war.
  3. Done is better than perfect. – Every single person on our team is a high-achiever. Perfection is everyone’s middle name. However, when shipping new product features, I’ve learned that done is always better than perfect. In fact, there is no such thing as perfect. Creating the best product for the market requires constant iteration. Time is always passing, cultural norms are always shifting, technology is always advancing, people’s wants and needs are always changing, and thus the market is always moving. Perfect today might not be perfect by tomorrow’s standards so theoretically, there is no end to improvement. That said, at a certain point, it is more important to launch your business, product or feature sooner and worry about perfecting it later. Some benefits are obvious: less time to market could mean a first mover advantage over competitors. Others, less so: you will get a better understanding of the core product and the things that are most critical to your customers. The most important thing when launching a new product or feature is getting feedback from the actual people who use it. The sooner you publish, the sooner you polish. The worst feeling is perfecting a new feature that it turns out no one wants, or no longer needs because the need no longer exists or because it is being satisfied in a different way or by a different source. Time, money and human capital are basically a luxury for start-ups. The minimum viable product or MVP will do the first time, every time.
  4. Jack be nimble, Jack be quick – small size is an advantage.  What I love about working at a startup versus working at a corporation is the agile nature of the business and the speed at which the team implements change. If something isn’t working or yielding the desired results, WE CHANGE IT. Immediately. There is no bureaucracy. Nothing stands between us and a quick response to feedback, besides data and an impromptu pow wow. Our size is one of our biggest advantages when going up against larger, more established companies.
  5. There’s real value in your story. As I mentioned in my previous post, one of the reasons I felt comfortable joining Jopwell was because I was confident in the fact that this team is the only team that can bring this specific idea to market at this specific point in time. A huge part of the pitch to investors up until this point (including Y Combinator) has been about the networks we have built, the collective resources we have amassed and the expertise we have cultivated as a result of our unique experiences navigating various diversity recruiting programs since high school. Our story is also a part of our unique value proposition that we leverage whenever possible. Investors, the media and users all buy into our story and as a result, we mostly pitch our story instead of having to sell it.

My Startup Journey: How I Became the First Hire at a 4-Month Old, Pre-Seed Stage Startup

At the end of 2014, I joined Jopwell, a minority recruitment tech platform that connects Blacks, Latinos and Native Americans to top companies for internships and jobs. I joined the company four months into its establishment as the first official employee, to lead business development. Since my start, I have received many questions from family, friends and even strangers, curious about my decision. Here is my story.

I admit, I wasn’t initially blown away by the idea of Jopwell and the need for a tech solution to diversity. I was a beneficiary of some of the more well-known non profit organizations providing access to educational and professional opportunities for ethnic minorities from underprivileged backgrounds. As far as I knew, there were plenty of existing solutions to America’s diversity problem.

Despite this however, my decision to join the team was very simple. It came down to one thing – the people. At the time, Jopwell consisted of two people and a dog.


Porter – Co-Founder and CEO, Ryan – Co-Founder and President and Max – office pet, all crammed into a 12×6 room in WeWork (shared office space for businesses, usually start-ups) in SoHo. I’ve known Porter since high school. We became fast friends at Lawrenceville when he started as a new boarding student sophomore year. There weren’t very many students of color at the time, so we were happy when new students of color were admitted and quickly grew pretty close trying to navigate the new environment together socially and academically.

During our junior year, a Vice President in Diversity Recruiting at Morgan Stanley launched a program to expose students of color to Wall Street and the world of finance at an early age through an internship. Porter and I were selected to interview and fortunately received the opportunity, at 17, to intern for one of the best banks on the street. One summer, on a bus ride from Morgan Stanley’s Westchester office to its Manhattan headquarters, Porter was bouncing some of his random, eccentric business ideas off of me, as he often did. I would weigh in and attempt to pick them apart for fun. But that day, he definitively put it in the universe. He promised that he would start a company one day. And I promised that if I could, I would help him build it. One day.

I went off to UPenn, continued at Morgan Stanley for 4 summers and eventually started my career in management consulting. He went off to Yale, spent 5 summers at Goldman Sachs and eventually started his career in finance there, selling foreign currencies. We still managed to keep in touch over the years and caught up at a high school reunion event, where he filled me in on his decision to leave Goldman Sachs and on his early progress with getting Jopwell off the ground. Since high school, I had always known Porter as a passionate and determined person who dreams big and gets things done. So when he told me he quit, I knew he wasn’t blindly chasing a lofty dream, but diligently working towards a clear goal.

Coincidentally, I also went to school with Ryan. We were one year apart at UPenn, but we met for the first time in that cozy 12×6 SoHo office. After spending many hours talking to Ryan – getting to know his story, understanding his role in fulfilling the Jopwell vision, understanding how he and Porter were executing on that vision and watching him field tough questions from investors to close Jopwell’s first large round of funding – I knew this was going to be a special team. The unique combination of our personalities, backgrounds and personal experiences made us the right team to tackle America’s diversity recruiting problem at such a critical time in this country’s history. We had all received amazing opportunities through diversity recruiting initiatives and wanted to provide the same access to people who may not have had the same resources that we did.

I am a relatively risk averse person, so before joining an early stage, pre-seed startup it was important for me to have the utmost trust in my teammates’ sheer hustle and leadership abilities. I am a Jamaican immigrant who also coincidentally grew up in South Jamaica Queens, New York before educational opportunities led me to a completely different environment. I have found my way to success in both gritty, resource-strapped environments and in ritzy, opportunity-rich ones despite numerous challenges and failures along the way. As a result of this unique upbringing, I am confident in my ability to succeed, no matter the odds or the playing field. Before diverging from the path I had mapped out for myself in the corporate world, I needed to have the same trust in Porter and Ryan. But observing their interactions, was just icing on the cake. Their natural business acumen, keen salesmanship, unwavering passion and clear vision combined with their scrappy nature reminded me of myself in so many ways. I saw how in sync they were with each other’s thoughts and how they resolved problems when they weren’t so in sync. I saw their individual strengths and weaknesses and how well their strengths complemented each other’s weaknesses. Lastly, I saw how resourceful they were with both their financial and social capital. This gave me all the confidence I needed to ultimately join the pair on the journey to leading Jopwell to success.

Six months in and looking back, I am confident in my decision. Before joining Jopwell, my life experiences have never been more relevant to the work that I do on a daily basis and that is a truly amazing feeling.


I chose “The 50th Law” by 50 Cent and Robert Greene as my reading material for the trip. It basically centers on one cardinal principle: fear nothing. Of course, this theme fit in really well with the trip. It wasn’t purposeful, I’ve been looking forward to reading it for quite some time now. Anyway, within the first few pages, Robert Greene immediately caught my attention with some thought-provoking ideas about fear and human nature. I found it kind of frightening how closely my thoughts mimicked some of his words, many of which I share and live by as principles and others which I previously considered but chose not to embrace. I haven’t finished the book yet and I won’t ruin it all for you, but let me share a few thoughts with some of Greene’s ideas peppered in…

“Your fears are a kind of prison that confines you within a limited range of action. The less you fear, the more power you will have and the more fully you will live.”

I have long considered myself a fearful person. Many Caribbean-born/American-raised people would probably agree, fear is a cornerstone of mom and dad’s parenting style. That’s where my fear originated. My mom in particular ruled with an iron-fist. I, in turn, was an obedient child who followed the rules (for the most part) and clung to my parents’ every word. Together with my dad, my mom did/is doing a great job of raising my sister and I into competent, compassionate, independent and responsible adults, among other things. This fear of authority and consequence embedded in me by my mom’s parenting style probably kept me from making some mistakes, that my peers in an environment like Jamaica Queens commonly made, like getting pregnant, getting arrested or doing drugs at too early of an age to understand or deal with the consequences myself. I am eternally grateful to my parents for this. Their austerity kept me on the straight and narrow and got me to where I am today.

“This fear eventually taints you, it quietly tames you.”

But eventually, this fear becomes a pervasive mindset that affects how you view certain things in life, like authority, the status quo and your power with regards to challenging them. This fear eventually taints you, it quietly tames you. It makes you dependent on tradition, structure and order and ill-adapted to chaos, fluidity and change. Robert Greene said it best, “[You] shift from feeling fear because of some threat, to having a fearful attitude towards life itself.”

The moment I realized this about myself is the moment I emerged from my shell and started living, as cliché as that sounds. The most successful people, the change-makers, aren’t obedient. They test the waters no matter the current and embrace changes in the tide. In my quest to be one, or at least to be my best self, I had to re-examine the way I operated and everything I thought and believed; I had to embrace experiences I previously avoided out of fear and approach everything with a novel eye. I saw these new experiences as opportunities instead of risks. Some experiences turned out to be actual risks, lol. But even so, most turned out to be opportunities that propelled my development forward. “Understand: momentum in life comes from increased fluidity, a willingness to try more, to move in a less constricted fashion.” I made a committment to being more fluid and this newfound openness has, so far, been a splendid decision full of new lessons and applications. It has been an immensely rewarding journey that I have yet to question.

“I saw these new experiences as opportunities instead of risks.”

Although unintended, this trip was another successful step forward in eradicating this fearful attitude towards life. It has really solidified some things I always knew to be true. For example, “In times of prosperity, we have the luxury of fretting over things.” This gave the expression “first world problems” new life, and not in the traditional sense! In Thailand, I had to divert the energy I previously spent fretting over frivolous things, like the potential for poor outcomes, towards a heightened attentiveness in the moment that would allow me to make more acute assessments of my surroundings and actually led me in the right direction. Twice, on something like a 5-hour BoltBus ride, and once in a taxi, I was dropped off at the side of a highway and pointed towards the direction of my assumed destination with a few botched English words. Twice, on something like a 12-hour regional Amtrak train ride, I was left to “guess” my stop based on the activity of other passengers. I didn’t have the luxury of spending time worrying about the difficulty of my predicament; I had to look for opportunities around me that I could leverage in order to solve my problem and get to my ultimate destination. As Roosevelt once said, “…the only thing we have to fear is fear itself — nameless, unreasoning, unjustified terror, which paralyzes needed efforts to convert retreat into advance.” My experience navigating Thailand and observing the culture is a testament to that. As a result, I’m so glad to say that today, not only am I less bound by fear of the unknown and potential future events, but I am also more solution-oriented and less problem-focused than I was yesterday and I am all the better for it.

“In times of prosperity, we have the luxury of fretting over things.”

By now, most of us have either learned or been told, as Roosevelt suggests, that attitude plays a critical role in success versus failure. One’s attitude often times shapes one’s reality and I always considered myself a realist. I live life and base my decisions on the facts that present themselves around a given situation. I have heard many people tell me that this is a negative mindset with which to approach to life. I never understood that. Realism, in its purest form, is impartial. It’s the events themselves that are either positive or negative. But I now understand.

Due to human emotions, realism is almost never executed in its purest form. Thus, negative events can linger on the conscience, eventually weighing on one’s outlook and perspective towards life. Guilty. That said, taking into account this Catch-22, I have learned that a realist actually needs to be more of an optimist. In times of adversity, you need to be able to see something better, something greater, for yourself, so as not to allow the daunting circumstances perceived around you, in that short moment, to guide your decisions. In adverse situations, the perceived circumstances around you, are by definition always usually less than ideal. So, being a realist in these situations inevitably restricts the solutions you can see for yourself. Your possibilities (and actions) are inadvertently grounded within the real context of your present circumstances. This is counterproductive to any real progress and advancement since presumably, in bad times, what you seek is a future way out – a way to the next level. I met so many people who expressed difficulty in adjusting to their new lives in Thailand or an overall lack of fulfillment in their old lives back home, but what got them through their respective transition periods was their ability to not lose themselves in the challenging realities of their present circumstances.

So with that, I challenge you to examine your own fears and limits. The time is now! Look inside and look outside yourself. What do you want to do? What keeps you from doing these things? Why? Repurpose my experiences, use them as a starting point to propel yourself towards your own growth; use them as encouragement to start your own journey – whichever form that may take. Experiment. Reorient your thinking to the possibilities of your desires. What would these possibilities look like without your preconceived limits or notions of fear? Get after it and find out. You might lose, but you might win. Either way, you learn and you grow…closer to finding peace of mind.

“…move before you think you are ready…it is a law of power that your energy will always rise to the appropriate level.”


Part 2: Oh, the places you’ll go! Oh, the people you’ll meet!

I rode to the Phuket ATV Park with the IT director of the company. He received my online reservation and upon realizing that my location was too obscure for the minibus with the rest of the group to navigate to, he picked me up in his pick-up truck instead. I know, this would never happen at home! There are too many Ted Bundys in America. But remember, anything goes in Thailand. They just operate in whatever way is most practical at the time, with little attention to the “rules.” But on our ride to meet the minibus, we struck up regular conversation. He asked where I was from and what brought me to Thailand. I obliged. He then followed up with his story.

He is from the southern part of Thailand, even farther down than Phuket, closer to the Malaysian border. He told me he was born and raised in Thailand, but he often gets mistaken for a tourist in his own country. The other natives think he is Malaysian. He did look a little different from most others I saw. He had longer, wavier hair – which he kept in a ponytail, his skin had a slightly darker hue to it – almost bronze, he had a stockier build and his face was broader than that of others. I have no idea if these features are common among Malaysian people, but that is what I noticed in him. He spoke great English, which he told me he learned in school growing up and from his English teacher, Tony. He also told me how he went to university in Thailand, where he studied Tourism. I know tourism comprises a significant part of the Thai economy, but I was surprised that the schools had a major dedicated to it. How practical! American colleges emphasize intellectual curiosity more so than practicality, when it comes to higher education. Considering the employment numbers and trends of my peer group, I think we could take a page out of the Thai handbook on that one. We talked about our love for the warm weather and laughed over a story about a trip he took to visit a friend in Finland during its winter season. He thought he was going to die between his walk from the airport to the car because it was so cold. He had his friend rush him to the hospital, where to his surprise, the doctor only gave him a few shots of alcohol to warm up and sent him on his way. LOL. Ridiculous. He wants to visit New York one day – but only in the summertime.

On my way back from Phuket, I met a boy on the bus from Mauritius. Mauritius is an island off the coast of Madagascar. Madagascar is an island off the coast of South Africa. It’s alright, I needed all the reference points too. To give you even more context, the now extinct dodo bird originated from Mauritius. They are a multi-ethnic people mixed with Black, White, Indian and Asian. They speak French. This young man went to university in Australia and stayed there after graduation because there were more opportunities. He is now a social worker, or he was a social worker, until he quit his job to travel. He enjoyed his job, despite the troubled teens trying to stab him every once in a while, but he felt he needed to get out and see the world. He needed a spark. He is backpacking through Southeast Asia for three months and was on his way to Ko Samui, an island off the eastern coast of Thailand, for the upcoming full-moon party. He seemed like someone you could find right here in the city, dressed in a retro Chicago Bulls snap-back hat, a pair of Raybans, a tank top, cargo shorts and matching Nikes. He had both of his ears pierced too. He was certainly the most stylish back-packer I had come across during my 10-day trip.

On the second leg of my trip from Phuket back to Bangkok, I met a girl from LA on the overnight sleeper train. It later turned out that she actually went to elementary school with a mutual friend who went to Penn with me. Small world. But anyway, the food finally got to me and we met because she offered me water when she saw that I was sick. The next morning we realized we were sitting across from each other and she asked how my stomach fared through the night. From there, we got to talking. She just finished her stint teaching kindergarteners in a province outside of Bangkok. Prior to that, she had been working as a paralegal in Atlanta, hating life and doing work that wasn’t mentally stimulating and that wasn’t benefiting anyone in a meaningful way. She needed a change and opted for a complete 180 by taking the teaching position in Thailand. She left a comfortable life with a decent paycheck, an apartment in downtown Atlanta and a boyfriend for a new life that at first, she questioned a great deal. She now had to live in an industrial complex outside of the city that was not very scenic at all, she didn’t particularly like small children and had hoped to work with high-schoolers and she couldn’t get around on her own because of the location of the complex. Then, of course, there was the language barrier. But everything has a way of working out for the best. After nearly a year in Thailand, age fell in love with the kids and now even hopes to have her own some day, she met a new boy, and she got into her first choice grad school program. In August, she is going to Columbia in NYC to study public health. New friend!

We talked for an hour or so, until we got to Bangkok. Although her time as a teacher had ended, she was still exploring Thailand before her journey home. She spent the previous 10 days at a silent Buddhist retreat because she wanted to understand Thai culture on a deeper level. She and about 30 others lived like monks, sleeping on cement blocks with wooden pillows, eating twice a day for breakfast and lunch only and meditating for hours on end. They also learned some of the core Buddhist monk beliefs. For example she told me one belief she struggled with was their view of happiness. Basically, everything that most people believe is true happiness is not, but instead it is actually suffering. Nothing on Earth or in life is lasting, so in order to achieve real happiness, you must rid yourself of any emotional attachment to material things and even to loved ones. This did not sit well with her and she went through a series of different emotions throughout that short time, from feelings of peace to feelings of depression and even to feelings of anxiety. But, she made it through. Many people did not and instead chose to leave at various points throughout the 10-day period. Backpacking Thailand alone sounds like a huge challenge, but I feel like her previous 10 days were infinitely more rigorous than mine.

We also talked about our views on Thailand and the culture and it seemed she was very aware of her ‘Whiteness.’ I told her about my time in Phi Phi, how it seemed like a party haven for backpackers and about all the trash they left behind, destroying the aesthetics (and ecosystem) of the island. She expressed how horrible she felt as a White person in Thailand, having witnessed how others disregard the culture, treat their experience as a getaway instead of a learning opportunity and disrespect locals on their trips. It was an interesting and actually quite refreshing perspective to hear. Many people our age just aren’t that self-aware.

I am so glad to have had the pleasure of meeting such colorful people with  diverse beliefs and intricate stories in such a short time! Absolutely amazing.

Same Same…But Different

“Same Same” is a popular phrase here, for some reason. I didn’t get it. Instead of just saying, “The Same,” people say “Same Same.” Tourist shirts even say “Same Same” on the front and “But Different” on the back. I still didn’t get it. But now, it kind of makes sense…

On Sunday morning in Phi Phi, we got breakfast at a local bar on the island. The TVs caught our attention because of a story about a missing Malaysian plane. Apparently, it just went off the map and officials have yet to find any signs of it. It had been missing for 24-48 hours. Missing. In 2014. With no idea of what happened, where it went or the status or the health and well-being of the 200+ people on board. Is this an episode of LOST or what?

Anyway, it occurred to me in that moment that I am not exposed to international news on a regular basis. Most news channels at home, as far as I know, are local or national. Any other news channels focus on international news but from a US perspective. This realization quickly made me feel a little shallow and ignorant. I’ve been exposed to too much at Lawrenceville and Penn to not be more worldly. And again, the world is so much bigger than me, my everyday life and the bubble that is New York City or my immediate sphere of influence.

But then, in the same instant, another thought occurred to me that quelled these feelings just as quickly: probably 98% or more of people around the world primarily only concern themselves with their day-to-day lives and making a living. For most people, there is no incremental survival value gained in being aware of foreign politics or culture. This applies to people in Jamaica Queens, New York all the way to Phuket, Thailand. It’s a universal principle. Such knowledge is really only beneficial to individuals operating at the highest level of society – in business, medicine, engineering, technology, politics and the like – and practically irrelevant to most others. Same Same.

So there is no shame, necessarily, in not being well-versed on international affairs. But, considering that I am working to one day eclipse the highest levels of society, I, unlike most others, have a responsibility to work on cultivating my international perspective. Whether that happens through continued international travel or staying attuned via more neutral/unbiased international news sources it’s something I need to be more conscious of developing. But Different.

The Power of a Dollar

It’s funny how being here, even if only for a few days, has affected my outlook on affordability and the power of a dollar. 1 USD is equivalent to approximately 32 Baht. Anything that costs me over 300 Baht, or roughly $10 is a luxury. Let’s not event TALK about anything over 500 Baht (~$15), those things are just plain unnecessary. With so many vendors selling the same items in such close proximity to each other, there really isn’t any good reason to deviate from this formula. That’s the beauty of the free market and the principles of supply and demand.

Anything Goes

Everything here is basically off the books. Anything goes. Everything is always up for negotiation and if you win, you win; if you lose, tough luck. Thailand is a much less controlled and regulated place than the US. It seems there is only culture and tradition and no standard of governance to fall back on.

For example, mopeds and motorbikes are a very popular mode of transportation. People often ride around on them on highways and busy streets without helmets. They treat motorbikes like cars and oftentimes travel with as many as three or FOUR people at a time, usually very small children, on the bikes. Crazy. Motorbike accidents are so common here, especially among foreigners. It’s not the motorbike drivers who are the problem, it’s the cars and tuk-tuks that sideswipe the motorbikes or cut them off that cause the accidents.

Sometimes there are random police checkpoints, but my host told me those are only to make money off of foreigners. Foreigners following the same local norms are fined huge sums, while natives are free to pass.

I thought I would never be caught dead on the back of a motorbike without a helmet. Ironically, because it’s such a popular mode of transportation, I have ridden with my host several times, unprotected. Once, we fit three people on the bike on our way back from market. Who am I? I hope my insurance covers this.


“Do you want to go Phi Phi?”

“Hey, do you want to go Phi Phi? A bunch of us are going this weekend.”


“Oh, sorry! Phi Phi Island! I forget you’re not familiar.”

This weekend I traveled to Koh Phi Phi island (pronounced coe pee-pee) with my host and three of the other teachers from the foundation. Breathtaking isn’t even the word. I was in complete awe of the beauty of it all, the ENTIRE time. It was just unlike anything I had ever seen. With it’s fine white sand beaches, clear blue-green waters, colorful fish and islands that jut out of the middle of the ocean like tropical glaciers reaching high in the sky, it’s beauty was simply unmatched. And apparently, I wasn’t alone in my thinking. Hoards and HOARDS of people unloaded from ferries, yachts and long tail motorboats, like a spilled bag of rice, from dawn until dusk in order to take in the island’s beauty and surrounding wonders. It’s not even high [tourist] season yet!

A little after we arrived, we went on a 6-hour cruise to tour the island and surrounding beaches. We made various stops along the coast to snorkel, kayak, swim and just explore. At the end, we anchored our boat and watched the sunset at sea. It was a really captivating visual experience.

Throughout the duration of our cruise, the crew members played reggae classics the whole time! I’m talking Bob Marley, Shaggy, Sean Paul, Cecil, Buju Banton and Beenie Man. I just love that Jamaican culture can be found everywhere; it makes me so proud! One European girl said, “Wait a minute, this isn’t Thai music!” She wasn’t ready.

The one downside to the experience was the trash on some of the smaller beaches and in the water surrounding some of the islands. Phi Phi is well known for it’s full-moon parties that go from dusk until dawn on the night of each full moon. Over the years, tourists have watered down this celebration, making it less authentic to the tradition and culture. Today, full-moon parties just involve a lot of tourists partying with drugs and alcohol on the beach. The tide carries this trash left behind from these parties to the areas surrounding Phi Phi. One of our boat’s crew workers basically collected trash by hand when he could, as we cruised around various lagoons. Our boat stopped at a small bay with wild monkeys. You could basically get within inches of them, there were no cages, guards or barriers. There are clear signs saying not to feed them and not to leave any trash. People brought Pringles, water bottles and soda cans and gave whatever they could to the monkeys for a cheap thrill or a photographic moment. -_- It’s so sad how people sometimes just have no regard or respect for nature. We ruin everything!

The sights I saw yesterday were what I’ve been dreaming of and looking forward to experiencing in Thailand. The world is just so very beautiful!

At night, Phi Phi reminded me of college. Our hostel was on the beach, alongside a strip of bars and restaurants, probably about 100 feet from the water. Beginning around 8pm, every single one of them came to life, with lights, glow-sticks, pong tables, fire-twirlers, flaming hoops and blaring house/techno music. They should call it Backpacker Beach. Everyone was a young traveller. Everyone. It was cool to mix and mingle. I met people from Sweden, Austria, the Czech Republic and the Netherlands. No matter where from though, drunk people are all the same. Lol. The party didn’t stop until 3 or 4am, but who was complaining?

Part 1: Oh, the places you’ll go! Oh, the people you’ll meet!

(I’m not even sure if that Dr. Seuss quote is accurate, but it made for a good title.)

Here’s a look at some of the interesting people I’ve crossed paths with thus far…

I shared a cab with a German boy who was checking out of the hostel at the same time that I was. He was going to the train station to leave Bangkok and continue his journey north; I was heading to the train station to leave Bangkok and continue my journey south. It turns out he is just 20 years old, hasn’t started college yet and has been traveling for six months, beginning when he was 19. He started off in Australia for four months with a group of friends, but they ran out of money and because it’s hard to get jobs in Australia without a specific skill-set or license, he and his friends had to split up. He came to Southeast Asia because he had never been and wanted to see it. Wow! I was amazed at his valor! But apparently, backpacking between high school and college is very common among German youth. I could never imagine myself or my little sister doing this at that age. When he runs out of money again, instead of finding a job in whatever country he is in, he will return home and start university. He wants to be an English and Spanish teacher, as he is in love with languages. At some point, he plans on backpacking South America so he can brush up on his Spanish. He was so comfortable and confident about his extensive travel route(s) that he settled me. Moving from place to place, not knowing what the future holds and going with the flow was his idea of normal – just baffling. I freak out when the slightest change potentially throws my five-year plan off course.

We got to the train station and ate KFC (LOL, I know! I don’t even eat fast food in the States, but I had to choose between a spicy chicken breast served with a lemon sauce over white rice, potentially getting sick from local street food or being famished until arriving in Phuket the next afternoon) before our trains departed and we had to bid each other adieu. Although it was only for a short time, he gave me great perspective on a different cultural standard and the real meaning of autonomy and independence.

On my way to Phuket, I met a really cool, young married couple in their late twenties or early thirties. They have been living in Bangkok for three years now and absolutely love it. The husband is from Toronto and plays professional soccer for a Thai team, after a few stints in Europe, and the wife is from Chicago and spent some time teaching English in Thailand. They love their low-cost luxurious lifestyle, the weather and their proximity to relaxing vacation destinations like Phuket. They live in a sizable luxury condo in the middle of Bangkok for roughly 400 USD per month, they go to dinner out on the town as often as they want, spend weekends in Phuket at their friend’s villa on a private island and just live a very relaxing and care-free life. But it wasn’t always good. They told me stories of the initial hardships when they first moved to the country too. They each had moments where they were frustrated with the culture and language barriers, but then those moments became fewer and farther in between. Now they are well-adjusted and even speak pretty good Thai! These two gave me a pretty good perspective on a standard of happiness different from my own.

These two were also hilarious and hospitable people. After telling them how I’ve basically been starving, they laughed but assured me they could relate, as the wife did the same when she first moved too. They gave me a whole list of delicious foods to try in Phuket and their Thai names so I could request what I want. We also bonded because the husband, who has dirty blonde hair and green eyes, is actually Trinidadian! There are white Jamaicans and Asian Jamaicans, but it was still a little surprising. He turned his accent on and off like a native and we talked about food, carnival, music and other cultural similarities and differences. He still manages to cook authentic Trini food pretty often for his and his wife’s friends here in Thailand, even though he can’t find ackee, has to make his own saltfish and has to get jerk sauce and pepper sauce shipped from his family in Trinidad – very awesome couple and comforting conversation. These two were also a testament to adaptability.

I met my host in Phuket. She is the only other Black girl in Thailand from Indiana and is spending about a year working for a foundation and teaching English to children in Thailand. We share a lot of interests like Taboo, Robert Greene, and too many others to name. She loves Thailand, but loves traveling more and when her contract is up, she will move on to explore another country as an English teacher and start all over again. Amazing. I don’t think I’ve ever personally met a Black woman doing something so fearless and adventurous.

My host’s roommate is a fellow New Yorker. She taught in NYC for 10 years and when she visited Thailand on a vacation, she fell completely in love with the calm, loving and supportive culture. It was just exactly what she needed in her life at the moment. Upon returning home, she quit her job, bought a one-way ticket to Thailand and never looked back. She didn’t even have a job! The odds were indeed in her favor, because she eventually found a great teaching position at an international school here in Thailand. That was basically the best case scenario. She even found that in her contract at her position in NYC, as long as she gave them 30-days notice, she would be able to return to her position within five years (ah, the perks of tenure. So if things don’t work out, she has a great back-up. Incredible. This is no longer a story you only see on tv! She gave me a better understanding of what it means to follow your heart’s desire.

The other women my host works with at the foundation are so funny and full of personality. I told them my birthday is on Friday and they responded, “Oh my goodness, we have to go out drinking!” LOL some things are just universal. One of the girls grew up in Philly and went to Temple, she was also a Communications major. What a coincidence.

I hope I get to circle back with the girl who was going to be my host in Bangkok. She is Asian, but I don’t think she is Thai. She grew up in Long Island near me and is in Thailand for graduate studies. She had an amazing story too.

It’s kind of crazy the random connections you can make with people so similar and so different, so close and yet so far away from you too.

Market Madness

Remember the grossly under-priced tour I booked yesterday from the seemingly humble and genuine woman with good English? It turns out, it wasn’t a scam and the tour was AWESOME. Yes!! One point for Stac’s gut. Had I listened to head, I would’ve kept walking and assumed her price was just too good to be true. I usually NEVER go with my gut feelings unless they are well-reasoned. Due to jet lag, I haven’t really been sleeping; I just crash at random moments and take naps. I haven’t really been eating either – still afraid of getting sick. So this morning I woke up after 1.5 hours of “sleep,” but missed the free toast breakfast and had to hop right in the minibus at 7:00am for the tour. I have to say, I was on edge to the point of paranoia. I kept imagining how dreadful the potential tour scam COULD turn out. I was just waiting for the shoe to drop. You just never really know what’s real and what’s not. Thai people are so very kind! But so are the hustlers. It’s exhausting always having to be hyper aware of your surroundings, which makes it hard to relax and enjoy yourself. Bangkok is kind of draining. I’m definitely looking forward to Phuket. For some reason, I think it will be a little less intense. Anyway, eventually I calmed down. I was in a van with 6 other tourists, 5 men and 1 woman. They were all friends from Brazil traveling through Southeast Asia for a month. They were very funny and friendly. It’s interesting how even in a sea of strangers, being around certain types of people in certain situations can put you at ease sometimes. Our first stop was the infamous Maeklong Railway Market. Brace yourselves for this oddity. It was about a 1.5 hour drive outside of Bangkok. The market is set up along railway tracks and primarily consists of locals selling fresh produce and seafood. The kick is that four times per day, an actual train runs along those tracks, right through the market! The shop-owners pull-back their awnings and draw their items away from the tracks to let the train pass and when it does, they return everything as it was and continue selling. Talk about bizarre!

Our next stop, was the also infamous Damnoen Saduak Floating Market. It’s a market on water! Think, Venice in Asia. This was more like a flea market. Locals sold food, miscellaneous souvenirs, art, clothes, fruit and spices – the works. If you made eye contact, or even if you didn’t, the vendors would pull your boat to theirs or to their dock in attempt to make a sale. It was very cool, definitely haven’t seen anything like it before.

Lastly, we took a cruise in a long-boat, through the canals to have a look at how the locals live along the river.

After the tour, we returned to Bangkok and I walked home. No stress! Phew! On to Phuket!


Today, I got scammed! Well, sort of. So, I’m staying near Khaosan Road, a really popular area for tourists. The doorman at the hostel gave me a map and told me a lot of the temples are about a 20-minute walk away from the hostel. So I locked my backpack behind the front desk as I saw others do and set out with a map, a pair of sunglasses, mosquito spray, my cell phones, personal identification documents/cards and money etc. on a walk through the city. The sidewalks were narrow and lined with vendors selling food, clothing and other miscellaneous items. It was like walking through a more compact Soho or Chinatown. I saw interesting looking food items, but was way too scared to try anything. I haven’t bought any Pepto Bismol as yet and travelers diarrhea is real. I saw small shops selling cute clothes and miscellaneous items. There were many booths advertising various tours to different sites throughout the city. There are two really cool things I want to see, but they are in obscure locations, not easily accessible by public transportation. A tour or a personal driver is really the best bet. I figured a cab would cost too much and a tuk-tuk would be uncomfortable, considering the distance, so I opted for a tour. I checked some prices online and stopped at random booths for quotes, but everything was too expensive. I saw prices from 1,500-5,000 Baht. No way. On my walk, I randomly asked a woman at a booth and she quoted me 350 Baht. Bingo. She spoke English really well and seemed humble and genuine. We chatted a bit and since she had exactly what I wanted I purchased the tour package on the spot. I didn’t even question why it was so comparatively low. I’m not sure what price I was looking for, but that was an excellent one. (This might be a scam too, it has yet to be determined.)

After this, I continued on my walk, and as I was nearing the palace, a man sitting on a random ledge dressed in business casual said, “Hi, how are you doing? Where are you from?” I answered him and kept walking, but somehow we ended up talking. He started giving me advice on what to see and where to go, he was drawing circles and arrows all over my map. He seemed so helpful, too helpful, so I asked, “Wait a minute, who are you?!” I had no articulate way of asking him why he was sitting on a random ledge giving advice and if he does this often. It turns out he is a cop, but was in plain clothes due to the protests – some sort of undercover situation. Long story short, he feeds me some line about how the Grand Palace is closed for a holiday until 2pm, how the government is sponsoring tuk-tuk drivers with gas for the day in order to take tourists around. It’s really cheap, too cheap, and the driver basically takes you all around to different sites. The catch is, he takes you to random shops he claims he needs to stop at, in order to get the free gas vouchers and what you don’t know, or what you shouldn’t know is, if you buy something (which is obviously extremely overpriced) the driver will get a hefty kick-back at a later time. Good thing I read all about this scheme online. I went along with it to see it play out, and I must say, it got pretty elaborate. All these really well-spoken old Thai men were just in the right places at the right times, to enlighten me on something new. I can see how people fall for it. It’s amazing how convincing these people are and how they actually make quite a bit from it. When he saw I wasn’t buying anything from these vendors, he let me know his “shift” was almost ending and he had to go. LOL. At least I got a cheap chauffeur for the greater part of the day. The palaces and Buddha statues are beyond beautiful. But whether in New York or not, you always have to be on your toes!

Check out the pictures of my day, below!

“Dem A Bleach Out Dem Skin!”

My first quest here was to find mosquito spray, face wash, toothpaste, lotion and shower shoes. It was easy enough because 7-Eleven stores are like Bodegas or Starbucks here; there’s one on every corner. I just had to walk around the block from the hostel and cross a major intersection. There was a cross-walk, but there are no lights or virtual crossing-guards. I’m used to busy streets and crazy taxis in New York and I hardly ever cross at the cross-walk, but THIS I was not ready for. Traffic flows in a steady stream and of course, no one yields to pedestrians. So I basically stood next to a local woman and used her as a shield from oncoming traffic mimicked her steps. I felt like I was playing Russian Roulette with my life! She literally stepped out into moving traffic and stood in between cars as she slowly and casually made her way to the other side of the street. She was probably about 4’10” and offered me and my 5’7″ frame zero protection whatsoever, but I made it!

Inside 7-Eleven, I set out to find my toothpaste, face wash, mosquito spray, shower shoes and lotion and I noticed something peculiar. Almost every single skin-care product had some sort of whitening formula in it! I knew India and Korea were big on skin lightening/bleaching products. Both men and women in those countries like their skin to be as close to basically an opaque white as possible. But it caught me off guard here in Thailand. So because my chocolate skin brings all the boys to the yard I’d rather not go back home resembling Vybz Kartel I opted for anything that didn’t have the word ‘white’ on it, except my toothpaste of course.  This lotion for babies will just have to do! (After some more thought, I decided to chill on the face wash too. ‘Light’/’bright’ is too close to ‘white’.)


The Beginning

Packing. Let’s just say, I didn’t think it through! You would think, after 4 years of packing for boarding school and 4 years of packing for college, I could handle packing a single backpack. Nope, I still pack like this. Thank goodness my roommate upgraded me at the last-minute or I would’ve been screwed struggling way more than I already was! Her backpack is definitely bigger than my NorthFace and has more compartments, but I still ended up packing and re-packing that thing about a dozen times. Please note the status after my first 11 attempts. As you can see, the essentials were NOT inside. Problematic. So some things just had to go, like my towel and being cute. I can always purchase the extra necessities here, especially since everything is so cheap. Once I gave up on packing the cutest outfits, I got the real necessities in and got it done!

Traveling. Let me tell you how much TV I did not get to catch up on because there was no Wifi on the plane. Aren’t we in 2014?? I thought that was ubiquitous by now. I was so blown devastated. Instead, I read a little and slept a lot. But, there was absolutely no beauty in my rest. I woke up multiple times, to catch myself looking like A, B and C. I just have no couth when it comes to sleeping in public.

I walked on to the plane with a huge smile, the set-up was something I had never seen. It was chic, spacious and cushy! Then I got to my seat, which was not. I felt like a sardine in an actual tin can. But then my luck changed. The flight was pretty empty and so was my row! Needless to say, I took complete advantage and used all three seats as a make-shift bed for the first 10-12hr leg of my flight. It was glorious.

There wasn’t anything too notable about my stop in Abu Dhabi. The only thing I will say, is that I was intensely aware of being “different,” which was primarily due to how I was dressed (leggings, long t-shirt, cardigan, sneakers) compared to everyone else (traditional garb), as opposed to how I looked. I was conscious of whether or not my leggings would be considered too revealing, even though my cardigan and t-shirt covered my figure. But that difference was somewhat expected though, so no story there.

At the Bangkok airport on the other hand, I felt at home. The first thing I noticed was that all the signs, unlike in Abu Dhabi, were in English with Thai subtitles which is a little surprising, but made perfect sense. Tourism comprises a significant portion of the Thai economy. The country is the number one tourist destination in Southeast Asia. I went through immigration, bought a SIM card for my phone with unlimited 3G internet and a few minutes of talk time, and made my way to the Sky Train with no problem. They speak enough English to communicate the important things. I foresee the language barrier being the hardest part.

The Sky Train system is very clean, modern and easy to navigate. It reminded me of the metro in DC. Once I got off the train, I made my way to my hostel via a 15-minute tuk-tuk ride. A tuk-tuk is a 3-wheeled vehicle that serves as a taxi. There are regular taxis, but I’ve seen plenty of those in New York, so I opted for a tuk-tuk instead. It has no doors and no seat-belts. It’s just you, your driver and a prayer. All it takes is one sharp turn and you would literally be on the pavement in the middle of street traffic. It was still pretty exhilarating cruising around like that in the warm open air. The driver quoted me 200 Baht to get to my destination, I said no and before I could even low ball him with a counter-offer, he re-countered with 150 Baht. I still said no and ended up paying him 120 Baht. Negotiating is probably what I am looking forward to the most while I am here. It’s a fun skill to hone in different environments.

Hostel-ing. Since I wasn’t able to finalize things with my host in Bangkok in time, instead, I opted to stay in a hostel for the first night. Yes, a hostel. I know, when I think of the word “hostel,” this and this come to mind for me too. We watch way too much TV. In reality, a hostel is just a cheap place to stay, full of many international travelers. My hostel in particular is rated 2014 Best Hostel in Bangkok by Travelfish and it is set up like a dorm-room, but they vary and can resemble boutique hotels. If my host and I can’t meet/organize ourselves tomorrow, I will likely stay at a different one in a different part of the city for one more night, before heading south to Phuket. Tonight cost me about $11. It’s clean, comfortable, near some attractions that I will see tomorrow and I feel safe. No complaints here. Hostel fears debunked!

I’m so excited for what tomorrow holds! My driver said he could take me all around to various sites. We shall see. Tuk-tuk and away!


“One thing I wanted to tell you before you left, – not that I’ve ever travelled that far by myself, but I’ve done a series of things to put myself out of my comfort zone – have zero expectations about the trip, about what will happen, or who you’ll be when you come back, just go. And say yes to everything. I’ve done things before, and expected some huge cataclysmic shift and “nothing” happened. My expectations didn’t allow me to really benefit from the experience. It took me awhile to realize that.”

The above stroke of genius quote is from a recent conversation with one of my best friends that got me thinking about my expectations for the trip. I found it thought-provoking in its novelty, because his advice is almost the antithesis of that which I have received from most others so far. I can’t tell you how many people have told me how life changing my experience will be.

Ironically however, although my last post was teeming with personal desires and the inspirations behind my decision to take this trip, I wouldn’t go as far as to say that I have any particular expectations to fulfill. It’s almost counterproductive to this challenge. Part of the point of this trip is to find comfort in discomfort by embracing, or at least not shying away from, the uncertainty that comes with not always having expectations. Having expectations is almost a way for the mind to structure the unknown in a way that makes it a less formidable place to be. Expectations give people a false sense of security in situations where they often have no control over the outcome. My only expectation is to have fun, and since fun by my standards, is as simple as having some time to read a book and catch up on my thoughts – things that I have direct control over – I think I’m in pretty good shape.

To address the part about expectations around who I will be when I get back – this is not an “Eat, Pray, Love” situation. I’m not going through a psychotic break tough time, I’m not trying to “find myself” due to an identity crisis, nor am I trying to change direction in life. I don’t have it all figured out, but I can say that I am very happy with where I am and where I’m going and I have long had a strong conception of who I am as a person. I have already spent past years doing the bulk of my internal due diligence. This trip is not a manifestation of a quarter-life crisis. My quarter-life crisis already came and went. The trip is a tune-up; it’s merely a vacation with a twist. Unlike Kanye, I’m not looking for the answers.


“Step outside your comfort zone.”

I remember back when I was in high-school, our motto at the time was “Step outside your comfort zone.” Faculty and staff alike would frequently encourage students to do so, in the classroom, on the field/court and beyond. Every time I heard it, I remember always thinking, “Ain’t nobody got time for that,” “Now I exactly would I do that?” I am the queen who reigns – the keeper, the cultivator – not the conqueror. That’s not to say I don’t like doing the heavy lifting required for success; lest we not forget, there is also a fair amount of work involved in maintaining and advancing the kingdom – but that’s another discussion. My point is, I stick to what I know. That said, you can only imagine how little stepping there was going on anywhere in my life at the time. “Thanks, but no thanks,” I would tell myself. Attending a school like Lawrenceville, considering my background, was enough of a step outside of my comfort zone.

Even through college, those who got to know me well could attest to how risk averse a person I was. I considered each decision with the utmost diligence and Stoicism. If I made a mistake, it was probably because I had already calculated that I could mentally/physically/financially bear the consequences such an ill-fated decision would afford me. Yup, you get it – I did way too much thinking, all the time. But in a surprising twist, a fairly recent life event convinced me to make a change and over the past year or so, I have really embraced the notion of taking more risks so that I might grow from new experiences. Over the past year, this change in thinking has indeed served me well, so I will keep striving to live by it.

“Your fear of making a decision is rooted in the potential for difficulty in the future. The truth is, no matter what you decide, there will be difficult times in the future. So you might as well make a confident choice.” – Unknown

So fast forward some 8-10 years later from my high school days and I now understand exactly why I should step outside my comfort zone, why I need to step outside my comfort zone. As an adult who strives to be a better person everyday, in all aspects of life, constantly challenging myself to re-examine my behaviors, habits and beliefs in pursuit of mental/physical/spiritual growth is, by default, a routine exercise in habitual line stepping – with that line being (lo and behold) my proverbial comfort zone. To become a better person, I have no choice but to push past what I know and experience things I previously thought beyond me. Had I heeded this mantra then, I would have had more than a head start on the journey to growth that I am seeking now. Ironically, my high school motto partially inspired this trip. Putting myself in a position where I will have no choice but to rely on myself will surely shed new light on what it means to have faith, trust my gut and be resourceful.

To become a better person, I have no choice but to push past what I know and experience things I previously thought beyond me.

Another inspiration came from some more realizations on another subject. Anyone that knows me can also attest to the fact that I am a die hard New Yorker. It is, after all, arguably the greatest place on Earth. Unfortunately however, it can get pretty monotonous and feel like a small bubble of privilege and pretentiousness, which I despise. I love that I’m surrounded everyday by peers, doing and accomplishing some truly amazing things, and that I too, am on the verge of some great things – but we are such a small subset of the world at large. Every day, I see a Facebook post about a new JD/MD/MBA/PhD/Master’s program acceptance, a new publication, a new business/non-profit venture, a new promotion, a new license etc., some undoubtedly impressive and inspiring things, but “‘blessed’ is the new brag” and I never want to get so absorbed in my own goals/accomplishments/life/immediate sphere of influence that my tunnel vision disconnects me from the world around me. It’s so much bigger than that! I want to see, understand and draw inspiration from different types of success, definitions of life and forms of happiness. So with my 25th birthday approaching soon, I thought, “What better time to take a walk outside the Cave than now?!”

I try to show her that the world is truly hers for the taking.

Many of you know how dear my little sister is to me. For those of you who don’t, let me tell you, she is the little love of my life! I do a lot of things with her in mind. I try to show her that the world is truly hers for the taking. For instance, last year, I encouraged her to apply to a summer program called Girls Who Code, despite her disinterest in Math and Science and her affinity for Art and English. She was accepted and by summer’s end, she ended up growing a lot, accomplishing some great things and finding a new passion in computer science. Although she tells me how much I inspire her, what she doesn’t know is how much she inspires me too! I want to both follow her lead and teach her something new in the process. I want her to see that she should never let fear, complacency or the unknown anchor her stride.

Some other things that inspired this trip are a general desire…

to meet new people.
to learn new things.
to inspire and be inspired.
to have new experiences.
to be more carefree.
to lose [old parts of] myself.
to find [new parts of] myself.
to reflect – on where I’ve been, where I’m going and what I want.
to have more faith.
to be more humble.
to give more love.
to gain a fresh perspective of the world.
to embrace uncertainty and relinquish the [constant] need for control.
to live!

The Route

So my journey to Thailand, begins in New York on March 2nd. 18 hours later, I stop in Abu Dhabi, UAE for a 2-hour layover, which I wish was longer as I would have loved to go on a quick desert safari. From Abu Dhabi, my plane heads straight to Bangkok, the capital of Thailand, and lands on March 3rd. The total travel time is 20+ hours!! Yeesh. The thought of that alone makes my head, neck AND back hurt. Jesus, be an upgrade to first class. 

My original plan was to split my time between Bangkok and Phuket, to get a feel of the contrast between the big city and the coastal province, but the political protests in Bangkok are intensifying. So for my safety, I will probably only spend 1 or 2 days in Bangkok. I just can’t imagine embarking on the 9-10 hour train and bus ride to Phuket immediately after that brutal flight.

To give you some visual context, I created an animated map of my journey. I plan on updating the map with more detailed locations, pictures and descriptions for each of my stops, once I get to Thailand, so stay tuned.

Click on the image and press play in the top right corner to check it out!


Hello, Family and Friends!

I created this little blog, at the behest of my line-sisters, but I decided to share it with all of you as well. I’m not quite sure I will actually be able to curate posts regularly, given what is to come, but I will certainly try!

So, as some of you may know, a few weeks ago I made a decision and took a plunge. I decided that for my 25th birthday, I will go backpacking in Thailand for 10 days!!

(I would’ve extended the trip a bit, but PTO wouldn’t let me finish.)

I will be traveling alone, with only the things that can fit in my trusty old NorthFace and I won’t be staying in hotels. Instead, I will be “couch-surfing,” or staying with Thai locals (kudos to I will explore what the country has to offer and navigate the place primarily on my own.

Yes, yes, I know what you are all thinking. As this is definitely something new for me, my parents, family, friends and co-workers, etc., when spreading the news, I got all types of reactions. From excitement to bewilderment to confusion to encouragement to disapproval – trust me, I have certainly heard it all.  However, some were absolutely priceless! Check out my favorites, below:

“Thailand? That’s a Muslim country. Are you sure you want to go there?”

“Whaattt, you’re going alone? [Expletive], have you seen Hangover 2?! They have like, machetes and OxyContin over there!”

“That’s crazy. I could never do that. But you know, sometimes a little danger is cool. It’ll be nice.”

“Ohhhh, wow, so, you’re actually going on a real vacation…”

                                                                                                                                       “Backpacking??…Alone??…Wait, who??..Staaci?!”

“…watch out for the lady-boys and don’t try the opium.”

…and I thought I surrounded myself with the cream of the crop.Guess not, LOL!

“Everybody acts like I’m nuts. I’m not nuts, I just want to feel it all.” -Fiona Apple