Sunday, June 19, 2016

The Arrival Shock

"Hey Brother!" I excitedly yelled to Mike as I gave him a hug. I hadn't seen my best friend in over 4 months. I was ecstatic to see him and start this new chapter in our lives, despite the long red-eye flight and long day I spent in Buenos Aires.

After the initial goofy banter that is common in our unique friendship, I couldn't help but notice that Mike seemed a little uneasy. I shrugged this hunch off and went straight to the window of our 8th floor Airbnb to admire my first view of Santiago, Chile. It was beautiful. The city is backdropped by the scenic Andes mountains in almost every direction.


After taking in the view and catching up, we decided to head to the bohemian neighborhood known as Barrio Bellavista for dinner and a beer. When we opened the menu we were immediately hit with culture shock. As we fumbled through the Spanish menu, a waiter hurriedly mumbled, "buenanochequeestatomandoweon?"

"Que?" I replied. I thought I spoke Spanish pretty decently but I had no idea what this waiter had just said to me. Mike and I assumed he was taking our drink order so we each ordered a beer by pointing to the menu and saying "cerveza". It seemed that the waiter understood our Spanish, so why couldn't we understand his? And what were these strange words on the menu? Palta? I've never seen that word before. And did that waiter say "sipo" after we ordered our beer? What is a "sipo"?

Now I knew why Mike looked a little uneasy earlier. Did we just move to a city we knew nothing about? And a country we knew nothing about? Do they speak a different language here?

The answer to all three of those questions is yes. It just hit us that neither of us really knew much about Santiago or Chile or Chilean Spanish (or Chilean food, or Chilean beer, or Chilean people, etc). We got our first bit of culture shock and began to second guess ourselves.


Then our food and beers arrived. A plate of french frieds covered with grilled onions, steak, avocado (That's what palta means!), and topped with a fried egg. It was delicious, and so were the Kunstmann beers!

Things started looking up. Our optimistic personalities kicked in and we put to rest any doubts. Sure we didn't know much about Chile, but we were excited and open-minded, which is all you need when experiencing a new culture.


Our next day in Chile we began apartment hunting. What an adventure that was...

When we learned Spanish in school, we learned phrases like "Donde está la biblioteca" or "Donde está el baño". Sure these phrases can be useful, but as Mike and I began our search for an apartment, I began to wish I had learned even more practical phrases like "Do you have a 2 bedroom, 2 bathroom, furnished apartment available for rent?"

After entering over 20 apartment buildings throughout various neighborhoods of Santiago with no luck, we finally decided to use a booking agency called home urbano. At this point we had narrowed our search down to the hipster neighborhood known as Bellas Artes, full of personality, unique bars, amazing restaurants, and close to our coworking space. We saw a few apartments that were listed on home urbano and ultimately found the perfect apartment. Despite a mix-up that almost resulted in the booking agency giving us the wrong apartment while another group took our apartment, we prevailed and moved in just 5 days after we landed in this foreign city.

(View from the rooftop of our new apartment)

These first few days in Santiago were definitely not what we were expecting. They were full of ups and downs. We hurried to a government ID office to arrive near opening hours, only to wait 4 hours and have their computer systems go down and have to return another day. We nearly signed a lease for the wrong apartment due to a mistake by the leasing agency. Processes to get a bank account and become a legal resident were longer and more painful than the DMV. The cell phone signal around the city is intermittent and mostly 3G. We weren't in San Francisco or New York anymore.

Despite this culture shock and rude awakening, the Chilean people were far from rude. We immediately found many Chilean friends in Start-Up Chile and through mutual friends from the states. Every person we met from Chile was very excited to share their way of life with us. Hearing the locals express similar frustrations made us feel less foreign. Our new friends started inviting us to asadaos, teaching us slang, introducing us to business contacts, and helping us assimilate.

After we truly got to know some Chilean people, we realized we made the right choice. Despite our initial culture shock and hesitations, we now knew that moving to Chile was the best decision we ever made!

Sunday, May 22, 2016

Do Something that Scares You

The moment had finally arrived.  After months of agonizing uncertainty, our dream had come true and it was time to pull the trigger on the opportunity of a lifetime.  There was only one problem -during the longer than expected wait...life happened.  We managed to convince ourselves that the Start-Up Chile door had shut in our faces and it was time to start making other plans.

While Ray and Melissa were falling deep into their whirlwind romance, I started preparing myself for a cross-country move to start a new chapter and new challenge in New York City.  And just like that, the stakes had changed.  What would have been a no-brainer a month earlier, was now a choice with considerable implications.    

It's not that Ray and I had taken the decision to quit our great jobs and comfortable lives lightly, it was that now there was another life that was going to be greatly impacted by our decision.

In the end, the decision came down to four relatively simple factors:
  • We were a team
  • We were more than just partners, we were best friends
  • We had a great idea
  • Ray had found himself an amazing girlfriend
or in other words-
  • Either we both went, or neither of us went.
  • We would support each other, however things turned out.
  • Wolo
  • Melissa supported Ray and told him to follow his dream, even if it meant moving 6,000 miles away weeks after she had just moved across the country to be with him.

With the tough decision made, we had lots of work to do and loose ends to tie up.  In addition to breaking the news to work and our roommates, we somehow had to obtain letters from our doctors and the FBI proving we were free of disease and criminal records.  Against all odds, one month later Ray and I were granted visas and we set out on our journey to the other side of the world.

Although exhausted from travel (this place is seriously on the other side of the world), the excitement and adrenaline of touching down in my new home kept my energy and spirits high.  As I made my way to the Airbnb, though, I started to get a little worried.  I wasn't sure what I had expected, but as I looked out my window at a gray, dilapidated city, my excitement started to fade.   Soon after, doubt and fear started to creep into my mind as I started to question our decision - had we just made a huge mistake?

Friday, May 6, 2016

Start-Up Chile Acceptance

Months had passed since Mike and I submitted our application on September 30, 2015. As Mike mentioned in Hurry Up and Wait, our friends and family persistently asked us for updates that we didn't have. As time went on, our lives kept moving forward - full speed ahead.

Mike was progressing in his career and enjoying life in San Francisco. Having nearly given up on Start-Up Chile, he decided to plan an awesome bucket list trip to Carnival in Rio.


Meanwhile, I was living in New York, progressing in my career, and taking advantage of my ability to work remotely. I met a girl in Santa Barbara and fell madly in love. Luckily we were able to travel often and see each other at least once every 2 weeks. My girlfriend, Melissa, started looking at jobs in New York. She eventually found her dream job at Columbia University working with the health promotion site Go Ask Alice!. After a few weeks of interviewing and presenting, she found out on December 18, 2015 that she landed the job.

We couldn't believe it! After living almost 3,000 miles apart for months, we would now be in the same city! Melissa and I popped a bottle of champagne and toasted to the end of our long-distance relationship.

Just two days later, I received an email that would change my life forever (and Mike's, and Melissa's)...

2015 Application Process
Your startup has been selected!
Dear Raymond Collins,
Congrats! Your startup “Bucket List Sherpa” was selected to participate as part of Start-Up Chile’s new generation. You are about to begin a once in a lifetime experience: to build your startup along with a community of entrepreneurs from +70 countries is something you’ll never forget. Together we will build great companies and lead the startup revolution taking place in Chile. Welcome!
As stated in program´s Terms and Conditions, you will be the legal beneficiary of the capital and the one who must live in Chile for the seven-month term of the program.
These are the team members who you stated on your application. Please remember that the Beneficiary and team members CANNOT be changed:
  • Michael Swisher
The following steps in the process are as follows:
1) You must answer to admission@startupchile.org with either:
  • “Yes, I will participate. My arrival will be on February 15th, 2016"
  • “No, I won’t join the program”. It would be great to know why you chose not to join us.
***Please make sure to let us know whether you’ll join the program or not before December 25th. If you fail to do so, we’ll assume you chose not to join the program***
2) Once we get your email answer, we’ll get in touch with you within one week to provide all the information required for your arrival to Chile.
**Please DO NOT ENGAGE in any expenditure related to Start-UpChile until we get in touch with you with specific instructions on that**
We look forward to hearing back from you and meeting you within the upcoming months!
Kind regards,
Start-Up Chile Team





Friday, April 22, 2016

Hurry Up and Wait

The blessing and the curse of applying to a start-up incubator before you have an actual product, is that it forces you to think about every aspect of your future company before you might have otherwise.  For a couple of co-founders at our early stage of development, it was hard enough containing our excitement about the possibilities for our bright future, let alone answering 30 tough questions about our business that we hadn't yet considered.

"How have you validated your product market fit?"



We had some serious work to do...


With a looming deadline fast approaching, Ray and I upped our Google Hangout game and fought through our demanding schedules and time differences to race towards the finish line.  The application came down to the wire, (as you might have expected if you knew us in college) and we finished our video at 4:30 am with mere hours to spare.



Following our application submission, spirits were high as we began eagerly awaiting word from Start-Up Chile.  Before we knew it, a couple of months had passed and friends and family began relentlessly asking us when we would find out about our grant.  Ray and I had no idea how or when we would hear anything from this relatively unknown incubator halfway across the world, so we did the only thing that made sense to us at the time, remained cautiously optimistic that we would be hearing any day now...

 I hate to admit this, but after another month passed with no word, and with the questions from our enthusiastic supporters beginning to wane, Ray and I started to lose hope.  Had the opportunity that was going to kick us in the ass and send us on our next great adventure fallen through?  Had we screwed up the application somehow?  Or even worse...had we let our own optimism trick us into thinking we had a great idea?

Wednesday, April 13, 2016

Wait, why are you moving to Chile?


It has been about a year since the fateful night Ray and I first talked about Wolo at a friend's Vegas bachelor party.  That night ended pretty blurry for Ray (a great story for another time about a super-star DJ and some misplaced cake), but our vision is still as clear as ever.



We are very excited to (finally) share our journey, and even though we're a little late, we figured it would be best to start from the beginning.  We promise to update often so that you can catch up quickly or binge like your favorite shows on Netflix.

To take a step back, I suppose we unknowingly caught the Wolo bug during a last minute backpacking trip to Costa Rica that was inspired by the arrival of our first credit cards (dangerous beginning, we know :)  Ray and I were juniors in college at the time, and over the course of the last 10 years, our bucket lists have only grown bigger and badder, despite checking off some awesome things along the way.
For those of you who are hearing about our project for the first time, the realization that inspired us was the same as the mindset we had been living by for the past 10 years - Money is better spent on enriching life with experiences, and all experiences are more enjoyable when shared with friends.  

The idea had been right in front of our faces all along!  Let's create a platform where people can go to be inspired by, and connect with, other like minded people who share the same passions in life.

Fast forward a few months later when Ray and I met again at the wedding of our friend whose fateful bachelor party got the Wolo train moving (thanks Bao & Jackie!), and our plan started to take form,

After a few whiskeys, I popped the big question, "Ray, what do you think about applying for an incubator in Santiago?"

To which Ray of course responded, "Santiago?  As in Chile?  F**K yeah dude, let's do it!"