The Journey of Entrepreneurship with Cassandra Le


Cassandra is the creator and found of The Quirky Pineapple Studio, a virtual studio providing copy writing and content strategy services for businesses in the tourism, hospitality, and gastronomy industries. She focuses on writing heartfelt words that connect businesses to their audience, creating an engaged and loyal community.

When she’s not working, you can usually find Cassandra road tripping with her boyfriend, finding the best street food, and gallivanting through cobblestoned streets for the perfect Instagram shot! We chatted with her to see what inspired her to start working for herself.

Hey Cassandra! Tell us a little bit about yourself.

I’m Cassandra, a copywriter and content strategist at The Quirky Pineapple Studio. I’m originally from Virginia, but now call Madrid, Spain home. Usually you can find me working from my couch or favorite coworking spaces in Madrid, and sometimes I am working and traveling at the same time (perks of being location independent)!

A few of my favorite things in no particular order are:

  • Reggaeton

  • Discovering street food and hidden spots

  • Traveling

  • Cooking and sharing meals with other people

  • Meeting new people

I’ve been blogging since I was 13 years old and always knew that I loved writing and sharing experiences with people to inspire and motivate them to live a lifestyle that they’re proud of.

Things unrelated to work (so you get a rounded picture of who I am): I’m a Pisces (shout-out to all my other Pisces), I am allergic to cinnamon, and I don’t like breakfast foods (I really don’t like pancakes).

How did you get started as a content strategist?

I started as a copywriter and content strategist after quitting my full-time job and moving to Madrid! I knew I wanted to work in content and write, but I never knew how I could make that lucrative and something that could actually be my full-time job.

It took me a while to “create my own” path, but after researching a bit more about online jobs, creating a business, and realizing my own strengths - I decided to make a switch from being a lifestyle & travel blogger (what I was doing as a hobby before) and turned it into a service-based business.

Now, I’ve been working as a content strategist in English and Spanish for businesses and brands in tourism, hospitality, and gastronomy - helping them to hone in on their brand message and create a content strategy that brings in a community of loyal clients and fans.

What inspired you to take this direction?

This is a bit of a funny story because it involves the reason why I decided to move to Madrid in the first place! I had lived in Spain before, for two years, as a an English Teaching Assistant. After doing that for 2 years, I decided to move back home to the United States and find a full-time job. During my year and a half at home, I continued to work on my blog on the side, and got more involved in the creative and entrepreneur community in my hometown.

While I was doing that, my boyfriend and I were in a long-distance relationship: he was in Spain and I was in the United States. What really inspired and made me take the leap in this direction was the fact that we didn’t want to do long-distance anymore! But, I knew if I were to move back to Spain, I didn’t want to teach English. So, I had to get creative with what I could do and this idea of having an online business was always brewing in the back of my mind.

I quit my job and two weeks later, I packed my bags and moved permanently to Madrid, Spain and took my business full-time as a copywriter and content strategist with The Quirky Pineapple Studio! It was a huge change - but it’s been a great journey so far!

Working for herself is no walk in the park, but Cassandra has found ways to work hard and travel - while still maintaining her sanity!

Working for herself is no walk in the park, but Cassandra has found ways to work hard and travel - while still maintaining her sanity!

What has been your biggest challenge this past year?

My biggest challenge this year has been a culmination of moving abroad and starting my business at the same time. I thought that because I had already lived in Spain, I would be used to the culture, language, and people - but this time around, it was completely different.

Also, the fact that I was transitioning into a full-time entrepreneur put even more pressure on me to make things work for my business while trying to adapt to my new home at the same time. It ended up being really overwhelming the first few months because I felt homesick, frustrated, and defeated with my business and my new life!

It took a few months to get used to my unique situation of starting a business in a new country after immediately moving there - but it’s also helped me to become more adaptable and quick-thinking. I’ve definitely built a great community of international business owners, entrepreneurs, and relationships to help me move forward and keep me grounded when things get difficult.

What is your favorite part of traveling and working?

You know, to be honest, working and traveling is HARD! It requires a lot of discipline and time management - also, it really requires you to know your limits and when you need to take time off to rest and when to say “no” to activities.

My favorite part, however, has been the connections I’ve been able to create because I am working and traveling at the same time! I’ve been able to meet really great and ambitious people who are business owners, entrepreneurs, startups, and creative people in general! I’ve been able to share ideas, learn from them, and get inspired by the entrepreneurial spirit in each place that I visit.

Not to mention, it’s great to be able to control my own schedule and have the flexibility to travel and work at the same time  - working extremely hard certain days and having the freedom to go on a tour, go to the beach, or just enjoy the place I’m visiting!

Tell us more about The Quirky Pineapple Studio.

Ah, yay! The Quirky Pineapple Studio is a virtual studio offering copy writing and content strategy services for businesses in the tourism, hospitality, and gastronomy industries. We focus on using a business’s brand message to create heartfelt words that connect them to their target audience, to build brand loyalty and an engaged community!

The Quirky Pineapple Studio focuses mainly on brand loyalty and visibility - putting the clients (community) at the heart of everything we do because we really believe in creating a relationship with your audience!

We offer services like: website copy writing, content creation, brand and content strategy, and also branded event coordination in Madrid! We also have a few products like the Your Soulful Branding Workbook and an editorial calendar and stats tracker bundle to help people create soulful personal brands and organize their content creation and publishing process.

I’ve got so much more planned for The Quirky Pineapple Studio, like local workshops, retreats, digital products, group programs, and more! My big goal is to turn The Quirky Pineapple Studio into a physical space to host creatives, entrepreneurs, and travelers - where we can all share and connect with one another!

If you could offer any advice to other people starting out as a freelancer or entrepreneur, what would you tell them?

Oh, this is a great question! There are a few things I’d share before starting your freelancing/entrepreneurship journey:

  1. Figure out WHY you want to do this, especially as an entrepreneur… having passion, loving something, etc. isn’t enough. Know WHY you want to do something.

  2. Create a community that you can fall back on when things get tough. It doesn’t need to be a big community - but a small group of people who you can trust and depend on when things get tough.

  3. Trust your gut. Really… trust your gut, no matter what people say (take everything with a grain of salt) and trust your gut when it comes to important decisions.

  4. Last one is: GRIT. It takes a lot of grit to be an entrepreneur and keep business going. Keep going (if it’s what you love) and keep connecting with people!


Last but not least, what is your all-time favorite Croissant coworking space?

Oh this is so hard! I haven’t been to all the spaces (yet), but my favorite Croissant coworking space in Madrid, Spain would have to be The Shed Coworking! It’s so nice and modern inside and located in a great neighborhood!