2023 is already looking promising as I head into my one-year anniversary of owning my own business! Along this journey I’ve had the pleasure of looking up to many fellow creative entrepreneurs who are also living the nomadic artistic lifestyle that I’ve come to embrace as my own. Entrepreneurship can be quite lonely and in this short and fast-paced year, I’ve sought out community with fellow creatives more than I ever have before. Creatives who so happen to be old friends from college.

Cassandra Le (she/they) is a first-generation Vietnamese-American, immigrant living in Spain. They’re also a brand and visibility strategist and copywriter who believes that business and marketing can be fun and can be used to help historically marginalized folx build generational wealth and rock the system (read: BURN IT DOWNNN!).

After starting their first business selling customized bookmarks in sixth grade, Cassandra later went on to have a travel and lifestyle blog and personal brand. For over ten years, she’s been creating content across all mediums from written, graphics to audio, video, photo, and more. Through her business, The Quirky Pineapple Studio, she’s worked with small businesses around the world in English and Spanish – helping them share their story, connect with their community, and drive sales with content marketing that is enjoyable and with less manipulation. 

Now, living a location-independent lifestyle, she helps brands and businesses share their story and message and grow their communities with clients, supporters and ambassadors. Cassandra and I got to talk about how she threw the rule book out the window and is living life on her terms.

Lo: Tell us a bit about yourself! Who you are, what you do, and how you got to Spain?

CL: Whew – loaded question to get us started! Who am I… 

In professional terms, I’m the Creator and Founder of The Quirky Pineapple Studio, a brand strategy and content marketing studio for BIPOC, LGBTQIA+, and Feminist-run brands. I work as a Brand and Visibility Strategist, planning, writing, designing, and executing content marketing strategies for our clients. I’m also a Creator (first time I’m saying this aloud in a publication), where I create content that helps folx explore the nuances of different topics to create deeper connections to ourselves, our community, and our message in the world through travel and self-expression.

Personally, I’m creative, sensitive, a big people person, and a human trying to figure out what ‘life’ looks like as someone who floats in-between countries, cultures, and languages.

Originally I’m from Northern Virginia but have been calling Spain home for the past five years (seven in total if you don’t count the one and a half years I returned to the USA to try and make it in “Corporate America”). I first came to Spain to teach English abroad through a government program called Auxiliares de Conversaci├│n but later stayed and made my home here because I fell in love abroad with a Spaniard (that’s a whole other story!).

Lo: Tell us what the Quirky Pineapple studio is and how did you conceive the business? 

CL: The Quirky Pineapple Studio┬« is… really… all my dreams and the vessel I use to create a better world.

In more practical terms (lol) it is a marketing agency focusing on brand strategy, copywriting, and content marketing for mission-driven brands, thought leaders, and organizations who want to get their message heard, rally their communities, and make inclusive, awesome shit (read: content). 

Upon publication of this post, we’ll be celebrating our five-year business anniversary in December 2022! I’m really proud of where the agency has grown, from being just me to now a team of two full-time people and four to five contract writers.

Before having The Quirky Pineapple Studio, “The Quirky Pineapple” was a travel blog that documented what it was like living abroad. Then, when I was back in Virginia for one and a half years, it was a travel and lifestyle blog, exploring travel and living an “unconventional life”. When I moved back to Spain, I pivoted again and turned my blog into what it is today – a service-based business that helps people, businesses, and companies with direct one-on-one services and coaching/educational resources. 

Lo: What was your biggest challenge starting a business in another country?

CL: I think my biggest challenge in starting a business in another country was learning the culture of business in that country AND within that continent.

What works in one culture and country cannot be copied and pasted in another culture and country – this refers to business practices, pricing, marketing, networking, sales, etc.

Because each country and culture has its own way of valuing certain things (services or products), economic systems, cultural understandings, etc. – taking one business concept and moving it to a whole different country required me to really do a deep dive into my ideal clients, culture, and values.

Lo: How has speaking another language contributed to the growth/expansion of your business? Any language apps or things you used to help on your multilingual journey?

CL: I think the fact that I speak English and Spanish fluently (IE: I can definitely hold my own in a debate or argument now!) – has helped differentiate me from other marketing agencies. It’s also opened up my clientele to different folx who speak both English and Spanish or have some dual cultures/values that I understand and can relate to, being someone who was born and raised in the United States but has spent most of my adult life living and working abroad. I think that we function in Spanglish, this brings in some really amazing talent for our collective of writers, which gives us a multicultural and global perspective.

To be honest, I never used any apps to learn Spanish. I took it in middle school for a year, high school for three, and had a one-week volunteer trip in Guayaquil, Ecuador where I really put my (poor) language skills to practice. I think the best thing you can do if you’re learning a language is to immerse yourself in it – and not only immerse yourself in the language but the culture OF that language because language isn’t ‘static’, it’s a living thing that changes based on cultures, history, politics, etc. 

Lo: Much of your work can be done from home. How did you find your niches (IE: brand strategy and copywriting)  for the Quirky Pineapple studio? How did living abroad help and not help?

CL: I think I stumbled into this work, to be honest. I’ve been blogging since I was 13 years old after reading “Mommy blogs” and thinking… “What, I want to create content around my life and get paid for it!!”

Since then, I’ve created and had so many different types of blogs and content – on Xanga, Myspace, Tumblr, Blogspot, Live Journal, Blogger, Wix, Squarespace, WordPress, etc. – to types of content like travel vlogs, style vlogs, eBooks and workbooks, webinars, etc. I think the only thing I haven’t actually tried and created recently is my own NFT (might come later haha). 

From all that experience at 13 years old, just dabbling and experimenting, I realized I had skill sets that people would actually pay for. I decided to figure out which skills I enjoyed the most and then decided to monetize that. I also knew I wanted everything to be online so that I could create a location-independent business and lifestyle. I think my living abroad helped to solidify the “location-independent” aspect of my business because I added it into everything that I do and made sure that clients knew I was completely remote.

Lo:  What do you wish you could have done differently when first starting your business abroad? What advice do you have for people looking to also live and work for themselves abroad?

CL: Great question! I was just asked this recently in a Small Business Panel and I’ll use the same answer that I shared there – I wish I would have trusted myself more. I wish that I had more self-trust and confidence to stick by my decisions, follow my gut, and not need external ‘validation’ and ‘guidance’ that actually really hurt my self-esteem and self-confidence. 

In a more practical sense, I don’t think I would change anything when I first started my business abroad. I think everything I did, all the people I met, and the opportunities I took on or didn’t have helped me be a better business owner, service provider, and person overall!

Some advice I would share with folx who want to live and work for themselves abroad –  I think I’d share two things:

Take some time to understand and explore who you are, the cultures you have, the biases, your privileges, etc. – The reason I share this is because most folx who move abroad end up comparing their home country to their new host/home country. I see this a lot with folx from the USA who move abroad and then basically impose their culture into everything (what we call cultural imperialism, can also be colonialism – I shared about this in my TEDx Talk). The more self-aware you are, the more you’ll be able to be a better business owner AND a human in general, especially when you’re mixing cultures, languages, customs, and traditions. 

Be clear on what you’re offering and how you help – Moving your business or work online requires LOTS of discipline, especially if you’re the one controlling your own schedule, work, etc. Knowing what you offer, what you do, how you help, and having the language and message to clearly share is how you can create more ease within your business! When you’re confused about what you do, what you offer, etc. your clients or community are also confused. 

Cassandra TEDx Talk on “How Current Work Culture Recreates Colonial Systems”

Lo: What’s been the most rewarding part of this journey for you so far?

CL: The ENTIRE thing! A lot of people asked me when I quit my corporate job, launched my business, and moved abroad (within a two-week time span, highly DO NOT recommend to folx) if I had a “Plan B”….

LOL, I did not have a Plan B. I actually was so confused why people would ask if I had a backup plan or some sort of contingency if this business idea of mine didn’t work. Why would they think it wouldn’t work? I certainly went in with so much faith and gumption that I told them that having a “Plan B” was a waste of time and energy because I knew this was going to work and I believed in myself enough to make it work.

The entire journey to get to where I am has been wild. I honestly don’t think I imagined The Quirky Pineapple Studio and my life the way it was – I kind of just put in the work, have my privileges to lean on, and went in with all this faith and now I’m running a multicultural brand strategy and content marketing agency, with clients around the world, a fully remote team, and doing fun projects within the business and personally!

Lo: Any self-care tips for aspiring business owners/travelers?

CL: SO MANY! I think I’ll share my top three self-care tips as a recovering workaholic:

  1. Have hobbies outside of work (I thought I had hobbies outside of work, but when we went into quarantine and couldn’t leave our homes during COVID, I realized I don’t have any hobbies that didn’t require going out, having coffee or window-shopping with friends.)
  2. Boundaries are so important in ALL areas of your life, boundaries with clients, yourself, what you accept/expect/do not allow, with your time, with your energy, etc. Having clear boundaries and actually being able to speak them and share them with people has really helped me feel less resentful, more at peace, and calmer. 
  3. Create dedicated spaces for yourself when you travel or work. For me, this looks like having a portable office set-up that helps me get in the zone for work and also carrying around crystals or my tarot/oracle cards when I travel so I can also have time to journal and reflect on things. Having the two helps take my mind from work to not work, and also keeps me grounded in different things.
Cassandra and I have the same tarot deck! Love the Star Spinner deck by Trungles
Photo by Laura Quintero Photography

Lo: Any last tidbits of wisdom you would like to share?

CL: I will share that having a location-independent life and business is really amazing and I’m so grateful for having one, but it’s not for everyone. A lot of things folx don’t see in my day-to-day thoughts, conversations with my therapist, and life are questions like:

  • Where do I belong? Do I belong?
  • What is home? How do I create a home?
  • How do I continue living this lifestyle and create a life I enjoy?
  • How do I find “real friends” if I’m never around them?
  • Do I move back to the USA to have ‘better’ opportunities?

It sounds super romanticized to say that this lifestyle is all amazing without sharing some of the deeper things that I also experience. I wouldn’t trade my lifestyle at all, but I do want to share that there are questions and conversations that I often have that require me to be very intentional about what I do – in my personal or professional life.

Needless to say, Cassandra’s words were exactly what I needed as I reflect on this past year of stepping into my creative entrepreneurship. Follow The Quirky Pineapple Studio on Instagram and be sure to check Cassandra’s Instagram to get the latest scoop on their life abroad!


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