Interview: Cassandra and The Quirky Pineapple

I am excited to share with you my latest interview with Cassandra, where she shares her story, and introduces her business. Cassandra and I met during meetup one evening in Washington DC, and I just loved her energy and passion. Her journey is so inspiring, and I hope you enjoy this interview!


Cassandra, the creator and founder of The Quirky Pineapple Studio

Cassandra is the creator and founder of The Quirky Pineapple Studio, offering copywriting and content strategy to businesses and entrepreneurs in the tourism and hospitality industry. She is originally from the Washington, DC area but now resides in Madrid, Spain. When she’s not chugging away on her laptop, you can usually find her gallivanting through cobble-stoned streets, looking for the next cool/hip restaurant or cafe, or traveling with her boyfriend!
1. So, you recently started an online business, tell us a bit more about it?
Yes! I have transitioned from being a lifestyle and travel blogger to a virtual micro-agency offering copywriting and content strategy services for businesses and entrepreneurs in the tourism and hospitality industry. My business is called The Quirky Pineapple Studio and it has been running since the end of December 2017. I decided to rebrand my blog into an online business because I decided to move back Spain to be with my boyfriend (that’s another story for later), and knew that if I moved, I needed a job that would sustain me and allow me to travel and work with clients from all over the world.
The Quirky Pineapple Studio offers three main services:
– Copywriting & Messaging
– Content Creation
– Strategy Sessions (for brands or bloggers)
Through each of these services, I work with businesses and entrepreneurs in either the tourism or hospitality industry to hone in on their message and craft heartfelt copy that connects them to their community online AND in person. I believe that in the tourism and hospitality industry, there is a strong focus and importance on connection and building relationships. As someone who’s worked practically all her life in the customer service industry – I understand that experiences are the driving forces that keep people coming back to an establishment and what lure them in to “try something new”. The Quirky Pineapple Studio focuses on those experiences and shares them in clear and thoughtful copy and content, so your ideal clients can start the experience online, first, and then take it in person.
2. How did you know you were ready to leave your full-time position? What gave you the courage to move-on and do your own thing?
For the year and a half that I was home, working at a large engineering consulting company, my boyfriend and I had a long distance relationship. It was hard – but we knew that eventually, we would like to physically be together again. While working at my full-time job, I finally had the income to invest back into my lifestyle and travel blog. I used a lot of the money I was earning to invest in conferences, workshops, networking events, and equipment for my blog. I worked on it every day I got home from work and throughout the weekends. By then, my boyfriend and I had been dealing with long distance for more than 6 months. We had to decide who was going to move, either he would come to the United States or I would move back to Spain.
While we were deciding what we would be doing, I got really sick and needed to have surgery. That pushed our plans back by at least another 6 months. After my surgery, something in my mind clicked that I did NOT want to deal with using my PTO for sick days, I didn’t want to work for someone else, and I wanted to give it a try with my lifestyle and travel blog. So, it wasn’t until October that I realized I was going to make the jump and move AND quit my job. Also, all of my co-workers at the time were also transitioning into new positions at different companies and I didn’t want to stay at the same place. Something in my gut told me to give this a try, so I gave my month’s notice in November and left the company in December.
It took me a year and a half of testing, trying and experimenting to feel comfortable to finally quit my FIRST (and hopefully only) full-time corporate job and pursue my creative endeavors full-time. The courage was knowing that if I didn’t try this now, I would be stuck and feeling like I “should” have done it. Also, I realized that many of the priorities and lifestyle choices that my friends were making and wanted – weren’t my goals or my priorities. If I stuck with this career path, I would not be able to pursue the lifestyle that I WANTED. I wouldn’t be able to do everything I wanted to do, if I stayed at my previous job, besides jumping in and starting The Quirky Pineapple Studio. And if I didn’t quit, my boyfriend and I would have definitely still been dealing with long-distance.
I’m on a mission to create the lifestyle that I want, surrounded by the people I want to surround myself with and pursuing what I love. It sounds “romantic” and very privileged to say something like this – so I understand that this doesn’t apply to everyone. That’s why one of The Quirky Pineapple Studio’s core values is to give back to others who may not be in the same privileged and comfortable position I was/am in to pursue something like this.
3. What do you like about editing, copywriting, and ghost writing for other businesses?
Ah – this is another tough question because there are a lot of things that I love about copywriting, content creation, and editing!
To start off, I did not major in communications or English. I was actually enrolled in the Communications major program at my college (shout out to James Madison University!), but then I switched during my sophomore year to be a Hospitality Management major. Writing has always been my medium of expression. I’ve been writing since I was a little girl, keeping diaries, journals, and writing poems or short novels. I think it started when my mom asked my sister and me to keep daily journals of our days so that she could read them and know how our day was.
My parents are business owners, who worked during the day. While we were at school, they worked. When we came home from school, they were still at work, and wouldn’t arrive home until 7/8pm. My grandma took care of us after school and as part of our homework, my mom asked us to keep a journal recounting our day so she knew what was going on. I think from there, writing has always been a way to recount my ideas, thoughts, and opinions. I used it as a way to express emotions and keep people informed about my life.
My favorite part of copywriting, content creation, and editing is working with someone who is so filled with passion and ideas and working to create a message that they can proudly share their business. The reason why I chose to work with businesses and entrepreneurs in the tourism and hospitality industry is that these services offer a special type of experience that involves working directly with people and creating a sense of belonging, relationship, and building a community.
Working with tourism and hospitality professionals to create real, heartfelt, and honest copy to build a community is my favorite part.
Working with tourism and hospitality professionals to create real, heartfelt, and honest copy to build a community is my favorite part. It’s taking someone’s message, polishing it a little, and sharing it with the world – I love being able to be the support system behind a passionate business, company, or individual, creating copy that shares the absolute best of them!
4. You also recently moved to Madrid, Spain. How is life there? What is the most difficult thing you have had to adjust to?
Yes! I can now call myself a Madrileña! (;
Life here is really different! This isn’t my first time living in Spain, it’s my 3rd – so I’m going through a bit of a frustrating and interesting time trying to transition and find my own space in this city. I am originally from the Washington, DC area, so being close to a city is really great. I can find so many different activities, groups, events, restaurants, etc. There are so many different people living here, coming from all parts of the world. I am really enjoying exploring my new home city and learning to love all the quirks and growing pains that come with it.
The most difficult thing I’ve had to adjust to is giving myself patience and grace to adjust to this new lifestyle. Like I mentioned before, this isn’t my first time living in Spain and I have a high enough level of Spanish to get around, hold my own in a conversation, and even understand Spanish bureaucracy – BUT this is my first time living in Madrid. So I’m becoming frustrated with myself and that I am not “adjusting” or “integrating” as fast as I want to or thought I would be.
5. What is the greatest benefit to hiring a skilled copywriter, like yourself?
Ooh! The greatest benefit to hiring a skilled copywriter is having a consistent and clear voice throughout all of your platforms, that is strategic and will connect with your ideal audience.
I’ve found that hiring a copywriter is always a last-ditch investment. Everyone always focuses on hiring a graphic designer, website developer/designer, photographer, etc – all the visual aspects, before working on their message and clearly expressing it. Although I definitely believe that the visual aspects of branding are extremely important, the COPY is what is going to hook in your community and share your brand’s personality in a way that instantly connects to your audience. If you aren’t clear about your business’s message or what you’d like to express to your audience – the visual aspects will be all over the place and won’t have as high of an impact.
The greatest benefit to hiring a skilled copywriter is having a consistent and clear voice throughout all of your platforms, that is strategic and will connect with your ideal audience
Hiring a skilled copywriter will take the guess-work out of writing copy, that only focuses on you, and use a specific strategy to really connect with your ideal clients/audience in a way that makes them intrigued and excited to learn more about your business, ultimately leading to sales and brand loyalty.
6. What is next for The Quirky Pineapple Studio?
Well, I have officially been in business for almost 4 months now – working on this full-time!
It has been an extremely BIG learning curve! Before, I had always viewed The Quirky Pineapple Studio as a side-hustle or passion, where I tried EXTREMELY hard to make it full-time but was always working for someone else or in another position. I love having all the time to focus my efforts on growing and building my business to be something that I am proud of – but it definitely comes with learning curves and a lot of discipline.
I’ve got a lot of plans for The Quirky Pineapple Studio and want to make it a place that not only offers copywriting and content strategy – but something more than that! My grand idea is to be a creative hub – for artists, makers, movers, travelers and more, to be a space that feels welcome and inviting, where they can share, learn, and collaborate with one another.

But, in the short term, I would love to start hosting online classes (I guess webinars?) and in-person events in Madrid! I want to teach others the power of words, skilled copywriting, and creating a personal brand! For the in-person events, I would love to bring together a group of creatives and others who want to learn and be part of the community, to host workshops, classes, or intimate dinners – where they can connect with others and find inspiration/motivation to chase their adventure!

7. If you could give one piece of advice to a woman who also wants to open her own business, what would it be?

One of my favorite quotes is:

“Good judgment comes from experience, experience comes from bad judgment”
– Rita Mae Brown
To me, this is the guiding factor in all decisions I make, leading to great opportunities, failure, or a weird route. This is the little dare that pushes me to pursue something that I’ve been thinking about for a long time. With this quote as a piece of advice, I would definitely recommend thinking about WHY you want to open your own business and WHAT you want out of it. Make sure that the reasons for those two align with something that feels good to you.
Thank you for reading you can find links to her website and social media  accounts below!