Chapter 45: Dominican Republic

Welcome to the Caribbean! We had a big adventure!

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After a brief four-month break, my passport finally came out for the first voyage of business school. Considering that the #1 stereotype about business school is that we 10% of our time doing “school” and 90% traveling, this will be far from the last trip of my academic career.

While “school” may only occupy 10% of my time (this is an exaggeration, at least 15% of my time is spent with educational endeavors!), classes do tend to cut into travel time. Month-long treks will have to occasionally be replaced by brief, 5-day sojourns abroad.

5-day trips call for closer destinations; I can’t fly to Seoul for the weekend, after all. However, considering my only experience abroad in North/Central America was a 5-day cruise to the Bahamas when I was a sophomore in college (and let’s be real, that hardly qualifies as going international), I am all for checking out Central America and the Caribbean.

Which brings me to this trip. New York’s finest business school gave us Monday and Tuesday off for fall break, so we decided to roll up 200-deep to the Dominican Republic.

There were minimal hiccups in the planning process, except for the fact that when 200 people tried to book the same flight from JFK to Puerto Plata at the same time (thank u Carly), the price 3xed in 15 minutes.

I also had a fun issue where the Chase Rewards Portal booked my flight under “RainesIv”, which led to me spending an hour+ on the phone with Chase and JetBlue reps until we figured out the problem. This led to a fun Twitter exchange between me and whatever intern runs JetBlue’s Twitter account, where they sort of gave us the greenlight to turn our flight into a party bus 35,000 feet up?

No matter, we made it. The squad took over a dozen Airbnbs and microtels around Puerto Plata, and festivities ensued. So let’s get into it: here’s a recap of the dumb stuff my friends and I did over the last five days.

Friday, November 4th


Haven’t woken up at 5:20 AM in a minute, but 7:30 AM flights call for drastic measures. I showered, thanked the exhausted figure in the mirror for packing the night before, and hopped in my Uber to JFK.

Over the last 6 months, I have become overly dependent on Clear for expediting my passage through airport security, but JFK is 20-years overdue for a makeover, and naturally they didn’t have Clear.

Luckily, my exit row upgrade (shout out JetBlue) got me into the priority security line, so I rolled up to my gate right as we boarded.

Our flight was deep with CBS kids (While the average age of my class is probably 28, “kids” still feels appropriate since we’re in school, right?); I think there were like 50 of us on the plane.

I’m also going to be referring to at least 30 people in this by name, and no one reading this outside of said people will know who any of them are, so that’ll be fun.

I was one of the first of our group on the plane, and Brody posted up behind me in the other exit row. He’s 6’7 on a bad day and needs every inch of the extra leg room. Brody was also ski masked up and passed out for the entire flight.

Coming into this flight, I had low expectations for JetBlue. However, they had free wifi that actually didn’t suck, which was a pleasant surprise. JetBlue is no Delta, but it dunks on every other US airline.

Squad landed in Puerto Plata (north shore of the DR) at like 11:30 AM, and there was a whole-ass band playing in the terminal when we disembarked. It was a total cliché tourist trap, but I’m cool with it. We went through customs, then Brody and I had to go *back through* customs because we hadn’t filled out any of the necessary entry forms.

At least we didn’t get deported.

Probably 2/3 of my Airbnb was on this flight, so we hit the ATM outside for some pesos (is every LatAm currency a “peso”?) before grabbing taxis to our place.

I knew nothing about the Dominican Republic and Puerto Plata before this, and I was expecting a resort-y type of place.


The town itself is really, really poor, and we turned off the main road (highway? Idk) down a dirt road that was in serious need of a repair job, and we pulled up at a legitimate compound in the middle of nowhere.

Home sweet home!

Like, every building on this street was a shack except for our crib. But man, this crib was a CRIB.

Our 20-person Airbnb had white-washed walls, a terra cotta roof, a pool, a patio, an outdoor bar, a gazebo, a yard, and a basketball court, and it was surrounded by a 10-foot-high wall topped with barbed wire.

Far left staircase = my room

Pablo Escobar-esque.

We honked the horn, and our security guard, Eroicio (I think), shotgun by his side, opened the gate and guided us in.

“Wtf is this place,” I thought to myself.

We headed to the living room to check the place out. I guess now is a good time to take roll of my housemates for the weekend.

Guys: Me, Brody, Jacob (Jacob and Brody were my first two B-school friends, we roomed together on a pre-orientation trip to the Hamptons), Ben, Matt West, Ray, Julien, Spencer, Landon, Griffyn.

Girls: Carly, Danielle, Alli, Ava, Liz, Olivia, Caro, Jordan, Maggie, and Rachel Kelly (who we do endearingly call R Kelly).

Caro, Puerto Rican, was the only fluent Spanish speaker in our house. I was distant second, but I was able to ask some important questions, such as “Puedo sacar una foto con tu arma?” (Can I take a picture with your gun?) to our security guy.

A lot of the rooms had already been claimed, so Ben (weekend roommate) and I set off to find any available beds.

There were a couple of small-ish rooms with queen beds available, but we hit the jackpot when we explored outside. There was an upstairs room with outside-only access around back, and it had two (2) queen beds with its own bathroom.


We thought we’d get our own beds. Didn’t really work out like that once everyone arrived lmfao. Four dudes in a room for a weekend gets pretty grimy.

The rest of the afternoon was spent boolin’ by the pool and playing spikeball. We were famished by 1:00, but thankfully our house came with three chefs/cleaners.

To keep a tally, we had an two armed guards, three houseworkers, and a bunch of taxis on call.

Unfortunately, the food wasn’t going to be ready til 2. While chilling in the pool waiting on lunch, I looked at Ben and said, “We’re kinda stuck here, aren’t we?”

He started giggling and said, “Barbed wire, big walls. It’s basically a prison hahaha”

We were, quite literally, stuck in a luxury prison.

A prison with a kickass pool, basketball court, outdoor bar, and some phenomenal chefs.

Pretty much our entire class was staying in 8 different prisons that could only be reached by taxiing from crib to crib. So that’s just what we did: we hopped from prison to prison every day, and we had different prison parties every night.

But you know what? Prison is a 10/10 time when you spend it with 200 of your closest friends.

We could walk to a seaweed-heavy beach nearby, to be fair.

The chefs served some cheese quesadillas while we waited on the rest of the food, and I ate like 12 of them. Massive mistake.

After lunch I passed out for like 3 hours, I was going to die without a nap. One of the other groups (200 of us here!) had rented out an entire hotel, and they were having a birthday party (there was a literally a birthday party every night lmao) for a dude in my class named Rohan.

The whole dynamic down here was pretty wild because it literally wasn’t safe to walk anywhere at night. You had to have a cab to go from spot to spot after dark, so we basically had like 10 “safe spaces” scattered throughout this dilapidated town.

I threw on a black wife beater, most of the group adorned Hawaiian shirts or the female equivalent of dudes wearing Hawaiian shirts, and we headed out.

I’ll be honest, we wanted to move the party to our pad, because we had a ridiculous party pad, but Rohan’s B-day was sick.

Whoever was on DJ duty (probably Brody and Ben, they DJ’d like 90% of the weekend) crushed it, a good mix of basic-white kid bangers and the Latin top 50. Taxi after taxi of CBS students pulled up throughout the night, and the gazebo/bar got packed.

I also learned new vocabulary word this night!

I was wearing minimal clothing (wife beater szn), and Maite, a Brazilian girl in my cluster (our classes are divided into “clusters” of 70 students), told me I was being a “Piranha”.

Apparently in Brazil, when someone (normally a girl) goes out to the club wearing minimal clothing to get attention, they’re a “piranha”.

Piranha is a great term for someone being promiscuous.

Low quality cluster photo

Back to the party. Everything was going great except the fact that 200 liver-hardened B-school veterans demolished the booze supply in record time.

Most of us headed back to the crib, but Brody and Julien ended up in another car headed “downtown”.

As you can expect, there is no “downtown” worth going to in Puerto Plata at 2 AM lmao.

When I got back, I started talking to our guard and asked what kind of gun he had.


“Ah, a 12-gauge. I have one of those,” I thought.

“Podemos sacar una foto?”


*takes picture which Eroicio*

“Puedo sacar una foto con tu arma?”


So I tried to get a pic holding the gun, but Jacob (wisely) told me to cut it out and go inside lol.

We kinda had rotating rooms over the course of the trip, but I think Jacob was my roommate for the night? Idk.

Saturday, November 5th


*slight cough* “THE PRODIGAL’S SON RETURNS!!”

Not how I planned on getting woken up Saturday morning, but I was happy to see my son Ben finally made it home at 8 AM.

Jacob has that dawg on him

We recapped the night, then headed downstairs for breakfast (shoutout to our cocineras for whipping the best desayuno in the game every morning).

Half of my house was going on a hike to see some waterfalls (I was supposed to tag along) and the other half was joining a bigger group for a boat party after lunch.

When I initially heard about the boat a month ago, I thought, “Man, I don’t really wanna be stuck on a boat.” The waterfall seemed like an excellent alternative!

But then at the party last night, Guillermo and Toni, my two favorite Colombianos, said, “Don’t be a loser, come on the boat!”

(Could be a misquote, but the sentiment is close enough)

So then I thought, “Damn, guess I need to get on the boat.”

After that convo I quietly told Caro, “…. I think I’m gonna skip the waterfall and go on the boat…”

To which she said, “Of course you should skip the waterfall and go on the boat, it’s a boat!”

Well the problem was that I didn’t have a ticket to the boat. No worries though. If I learned anything from spending two months in Argentina, it was that in Latin America, all you need is a little nepotism to get what you want.

Shoutout nepotism, I ended up getting a ticket for the boat.

Carly, who planned the whole boat thing, and who I initially told that I wouldn’t be attending the boat party, rightly dunked on me for my last-minute pivot.

At lunchtime we headed to the beach and boarded our ships. We had like 5 boats in total, and mine was two-stories with a waterslide running off the back.

About half a mile out from shore, we saw a ship was sinking in the middle of the bay. At first I thought it was supposed to be one of our boats (which honestly wouldn’t surprise me at all), but the captain said that they intentionally partially sink it every day as part of the scuba diving routine.


The music started blaring once we pushed off from the shore, and the ship quickly became a 2-story dance-floor with a bar in the middle.

I kicked it with my British mate Ollie for a bit while Matt West was busy coaching Julien up on nothing good.

An hour later we anchored in the middle of the bay, and Mr. West and I jumped off the top deck into the sea. R Kelly got wrecked, slipping on the deck, and she looked like a shark attacked her.

"Aim for the bushes" - us, probably

lol, lmao

Julien and I swam to one of the other boats to kick it with our boy Lawrence (Larry), and three of the Argentinians (shout out Manu, Agustin, y JC) joined us as well.

All of the Argentinians have nicknames for each other: Agustin is El Tanke and/or baby tank, Manu is The Gun, and JC is J Queen / The Queen. They are also incredibly homoerotic with each other. Just Latin stuff.

The whole party ended up on my boat (shocked that thing didn’t sink, we must have been 30 people over capacity), and then we headed back to shore.

Me, Julien, Mr. West, Larry

When we got back to our place, we decided that we were going to host the party for night two. Our setup was sick, our speaker was loud af, and we didn’t have neighbors.

We sent an announcement in the DR groupchat that we were having a “disco/pool party” (which is funny because literally no one had disco stuff on them. Why would they?).

Then we hung out by the pool, played basketball, ate some quesadillas, and set up for the fiesta.

Lawrence pulled up to pregame with us and said the cops had to escort him here. Apparently, he tried to walk from his Airbnb (he had his own place), and they straight up said it was way too dangerous for him to be walking down the unlit roads at night.

Anyways, people started pouring in at 10, DJ Brody and DJ Benny crushed the aux, and the place was bumping until ~4 AM. (I got chastised for “calling it early” by Jacob and Ben for going to bed at 3 AM. Sad!)

The party started off like pretty much any other party: music playing, everyone chatting around the bar, whatever. Then JC said, “Let’s cut off the lights,” and the action really picked up after that. The gazebo became a dance floor and people started jumping in the pool, while our shotgun-armed security guard made a lap around the house every 30 minutes.

The image of this Dominican dude casually dragging a 12-gauge through a party full of 200 MBA students is just as ridiculous as it sounds.

The party hit its crescendo around 1:30 when Toni and Agustin started plotting to throw folks in the pool, and then it just got reckless. Bodies were flying everywhere, phones were in danger of water damage, and it’s honestly a miracle JC didn’t get killed because he probably threw/got thrown in the pool no less than 10 times, and he was so many cervezas deep that he briefly lost the ability to speak English.

(At one point we were wrestling and I threw him a bit too close to the edge for comfort. I thought no one noticed until I saw Caro shaking her head at me like a mother who just saw their 8 year-old stealing cookies from a cookie jar. No Argentinians were harmed in the making of this blog.)

I also learned about this weird thing that all the LatAm kids do called “trespicos” or “3 little kisses”, where they straight up group kiss each other (These are typically cross-gender, I would like to point out)

For those who are curious, the LatAm : US contact equivalency chart goes something like this:

This is a joke, but also it isn’t.

When I asked Guillermo and Laura wtf was up with the LatAm crew ripping weird 5-way kisses, I got pulled into one myself.

As the great Justin Timberlake once said, “It’s not gay if it’s in a 3-way.”

It’s like a dap, but with your mouth.

As alluded to earlier, I cashed out at like 3 AM.

Sunday, November 6th

Sunday was, for me, a chill day. Like clockwork we had another phenomenal breakfast before playing some spikeball and kicking it by the pool. I had a lot to work on (newsletter, blog, and an online course I’m teaching on how to monetize a newsletter), so I spent most of the afternoon alternating between shooting hoops and working on my laptop.

Good Morning - Ben (identifies as Pea/Cock)

We headed to a beach-front restaurant for dinner that afternoon, and a bat shit on my thigh about five minutes after we sat down.

Besides that, the meal was great.

After dinner, Julien started a very heated debate over who would win a fight: five clones of one of us (like, 5 Jack Raineses), or a single female lion.

I personally think that if 5 of me fought 1 lion, we’d win. I’d lose 3 soldiers, but someone would survive.

Raz, an Israeli guy in my class, was having his birthday party at his house that night, so we headed over there after dinner. The second I walked in, I saw that one of my boys, Alex, had gotten cornrows earlier that day, and he looked insane. We ripped celebratory heaters, because why not?

It was humid and hot af, so I was literally a ball of sweat after an hour. After midnight, we sang happy birthday to Raz and some of the guys lifted him up on a chair in the crowd (Jewish parties are so sick. I think I’m going to apply to become honorarily Jewish). This devolved into random folks climbing on each other’s shoulders all over the dance floor, because who doesn’t want to be elevated?

Me and Toni (my son)

I went to the front gate to relieve myself, and two dudes with shotguns were standing on the other side.

“Are you the guy in charge of the party?” they asked me.

“Nah, I’m just the guy peeing.”

“Well we want to talk to the guy in charge of the music.”

“Is it too loud?”


“Do the songs suck?”


“Well I don’t really see what the problem is but yeah I guess I can give someone a heads up.”

I grabbed Clayton, one of the dudes staying at that house, and told him what happened. It turns out that the music was too loud, but the cool thing about the DR is that you can just pay a dude with a shotgun $50 to go away and he will.

So the party went on.

Aani (Argentinian girl in my class) and I ended up taking an album worth of photos from each event, so we snapped several on the dance floor at like 2 AM.

We made it back home at like 2:30, and a bunch of the guys in my house were planning on going fishing in the AM. Not I, big day teaching class.

Monday, November 7th

Matt West came up and grabbed Ben to go fishing at like 6:30 AM, and I went back to sleep for 4 hours. I woke up at like 10:30, grabbed breakfast, then worked on some stuff on my computer until class started at 1. We had a Zoom fiasco (of course), and had to pivot to a Google Meeting last minute, but it worked out.

Also, apparently Alex (cornrow guy) never went to sleep and showed up for the fishing trip. Insane.

Most of my house that didn’t go on the fishing trip hit the beach that afternoon, and I headed to Ryan, Guillermo, and JC’s house with Caro, Manu, and Toni.

While we had a barbed wire compound with armed guards on a dirt road, they had a beach front crib with a pool and hot tub that looked like it belonged in the richest part of Charleston, SC. I had a few piña coladas by the pool, before Guillermo introduced me to one of his friends.

Guillermo had met this dude, Martin, at McKinsey training like 6 years ago, and Martin was now doing his own digital nomad thing living wherever. He happened to be in Puerto Plata this month, so Guillermo invited him over to hang.

I walked up and said, “What’s up man, I’m Jack.”

And he replied, “We’ve met before.”

I thought that he had perhaps seen something of mine on social media, but he’s not even on Twitter. It turns out that he has been traveling for the last year, and we stayed at the Selina Hostel in Lisbon at the same time last December.

Sure enough, we had like 7 mutual followers on Instagram from the week that I was there.

You want to talk about a small world? That doesn’t even make sense.

Met this dude in Lisbon, pretty sure he dropships or something.

Caro and I headed back to our place for dinner, and I hung out with the fishing boys.

“Yo Brody, how was the boat?”

“Umm… it was good?”

*He busts out laughing*

“Ray and I were sea sick the entire time, it was rough”

Apparently, the sea was ridiculously choppy, and they never once stopped the boat. Like even when they were fishing, the boat kept on moving full speed. Brody and Ray were half-sick for the entire ride, but Ben and Captain Matt West were chilling.

We played a bunch of drinking games that night before heading to the third birthday party of the weekend for a girl named Cami (yes, I’m aware that this is getting repetitive lol).

Mr. West, premier entertainer

Just like yesterday, some dudes with guns had heard about the party. They came over before the party started and said the house needed to pay them if they wanted to blare music all night.

So they paid em like $40 and a warm bottle of tequila to screw off, a masterclass course in negotiations.

LatAm crew copied my gun pic

So we rolled up at like 10:00, and Aani and the LatAm girls covered our faces with glitter (this is important later!)

We realized that our house hadn’t brought enough drinks, so we paid a taxi driver to go scoop some. Unfortunately, when he arrived, we didn’t have enough cash on hand. While Toni and Caro ran around to raise some funds, I tried to make small talk with our delivery boy.

“Ummm, mi peluquero es Dominicano”

(My barber is Dominican)

“Cuento cuesta tu corte?”

(How much is your haircut?)


“$30??? Es $5 aqui!”

At least I didn’t ask him about the weather. Anyways, funding secured. We got the man his cash.

We kicked it over there until like 1:00 before heading back to the crib; no one wanted to feel awful with a 9 AM wakeup call and 1:00 PM flight.

Tuesday, November 8th

I tried to wash the glitter off of my face for like 10 minutes the next morning, but it didn’t work. So when I went through customs on the way out, the officer started making fun of me for looking like I got caught up in an orgy with Tinker Bell and the Fairy God Mother.

Having glitter on your face isn’t ideal! Having morning-after glitter all over you while you flew 3.5 hours from the DR to JFK really, really isn’t ideal!

And that brings me to today, where I’m writing this sentence 10 minutes out from JFK.

I hope you enjoyed my first grad school field trip ❤️ Going to spend January in Europe, so I’ll have more fun stuff to share then.

Catch you guys later.

- Jack

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