We’re excited to introduce you to the always interesting and insightful Cassandra Le. We hope you’ll enjoy our conversation with Cassandra below.
Cassandra, appreciate you joining us today. What was it like going from idea to execution? Can you share some of the backstory and some of the major steps or milestones?
My business, The Quirky Pineapple Studio, started off as a blog during my final year of college. I wanted to write about life after college, what it was like to transition into the working world, and travel. After graduating from college, I took a ‘gap year’ to teach English abroad in Spain – my blog, The Quirky Pineapple, shared travel stories, my experiences being Asian-American, and how it was to navigate through different cultures. The original idea and plan were to become a full-time travel blogger which I found to be more difficult than expected.
After two years teaching English in Spain, I decided to move back to the USA and get a ‘real’ job, full-time in Corporate America. I transitioned The Quirky Pineapple into a lifestyle and travel blog, talking about travel within the United States, women’s empowerment, and self-expression. I was trying to figure out what I was doing with my life because my partner and I were in a long-distance relationship and I quickly saw that the ‘blogging’ life wasn’t as lucrative as I thought it would be.
I started exploring different ideas to make money online and found a lot of different online business/small business/entrepreneurship groups in my area – so I started networking with them. It was really exciting because I started connecting with people who work online, create content, but they directly help their clients through the services that they offered – something I thought was way more attainable than becoming a blogger.
From all the networking events that I attended, I started thinking about how I could turn my blog into a business – not a business as a Creator – but one where I could sell services that people would pay for. I brainstormed different ideas, services, strengths, and skill sets that I could package together and sell.
I’m writing this now and it sounds like it was a super quick and easy process but making that transition into online business meant that I was also going to quit my job, I was going to move back to Spain so my partner and I didn’t have to deal with long distance, and I’d be taking a chance on this idea of mine. In reality, it took about 1.5 years for me to take this idea and turn it into a reality.
The first 6 months of the journey was really about networking and brainstorming what I could actually do…
Then the next 6 months was researching and figuring out if this was actually possible. I started investing my money into mentorship, going to paid networking events and conferences, and even investing into the business with branding, website, contracts, etc. During these 6 months I also had to work through how I’d tell my family that I wanted to quit my job, start a business, and move back abroad for love. It was INTENSE.
The following 6 months is when I started really making moves. I was working “two” jobs is what I like to say – my corporate, day job and my ‘side-hustle’ business. I was having calls, getting quotes, pitching my services, investing in business mentorship, and I had finally told my parents that I was going to take this idea and go full-time with it. It was terrifying and exciting at the same time. I had no idea what I was doing, I just kept telling myself if I believe in the idea enough and back it up, other people would have to see how dedicated I am and would want to work with me.
In December 2017, I quit my full-time job, hosted a launch party for myself (yes, I planned and paid for it myself!), and then 2 weeks later I packed all my belongings into four suitcases and got on a one-way flight to Madrid, Spain to start my “new life” as an online business owner, living in Madrid, Spain.
It’s officially been 5 years of full-time business ownership and whoa – what a ride.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers
I’m Cassandra Le (she/they), originally from Virginia in the USA but am now living in Toledo, Spain! I’m a first-generation, Vietnamese-American, eldest of three, and a Pisces sun, Virgo moon, and Cancer rising (if you’re into that type of thing).
I studied Hospitality Management in college, with minors in Business and Sociology (two very different subjects). Since I was 13 years old, I found out what blogging was and decided I wanted to be a full-time blogger/content creator. I quickly realized that the dream of blogging was not as lucrative, so I decided to pursue something else – marketing! To be honest, I didn’t ever want to be a marketer but I found that my skill sets and experience are really helpful for content marketing. Thanks to my interest in blogging from a young age, I’ve had experience creating all types of content (audio, visual, videos, images, etc.) that I use to help my clients amplify their message, create awesome content, and connect more with their communities.
Now, The Quirky Pineapple Studio works with BIPOPC, LGBTQIA+, and Feminist-run brands, small businesses, and thought leaders in DEI, Leadership, and Culture to help them share their message and awesome work, while also bringing in more clients and audience members.
I would say there are a few things I’m most proud of in my business and my brand:
#1: Professional –> Thanks to our brand message, values, and stories, I was a TEDx speaker in Los Angeles in 2021.
#2: Personally –> The business now supports me and my partner, pays for rent & utilities, vacation, and other things (something that I honestly was struggling to believe during the first 2 years of business)
#3: Professional & Personally –> We have a global audience and clientele that we work with – which is amazing because we’ve hosted tours around the USA to meet clients and community members
#4: Overall –> The idea that I once had to ‘make money online’ is now a full-on business that we’re working on every day and working to build. My partner now works with me in the business and we get to work on this dream and idea together!
What do you think helped you build your reputation within your market?
SO MANY THINGS – let me list them out:
#1: Networking
#2: Hyping myself up
#3: Clear brand message and strategy
And now let me explain:
NETWORKING — In the beginning of my business (and still now), I networked with ANYONE AND EVERYONE. I would go to free and paid networking events, conferences, workshops, summits, all of it – to get my name out there and build some sort of brand awareness with people who could be my ideal clients, collaborators, or potential referrals. I think because I networked so much and was “everywhere” (which is also very tiring, but when you’re starting it’s that hunger for growing that kept me going), it helped build my reputation within my market because people started putting a face to the name. I was a nobody, especially after moving to a foreign country, so I decided I’m going to network to make myself memorable and a somebody within the community.
HYPING MYSELF UP — Similar to networking, I knew that I needed to ‘earn’ respect and trust in a market that had no idea who I was. First, I was moving abroad to a foreign country in a foreign language – how will people know me if I am actually new to the area? Second, I was going to be networking in my home country/native language, so how do I maintain that connection with people in the case that I will also get clients from the USA? I hyped myself up every chance I had. Whether it was my first big client, marketing campaign, random idea, networking event I attended, etc. – I talked about myself like I was ‘hot shit’! It worked. I believed so much in my own business mission, brand message, and services that I hyped myself up everywhere – on social media, in networking events, pitching myself for podcasts, and all of it. Since I was everywhere in-person at networking events in Spain, and online – sharing my wins and being featured in media/PR outlets, it helped to build my reputation!
CLEAR BRAND MESSAGE & STRATEGY — Before jumping into all the networking and hyping myself up, I think the biggest thing that helped solidify and build my brand reputation was that I knew what I was saying, how I helped people, the benefits of working with me, and I had a clear strategy to get visible. Without that, I think my networking and ‘hype’ strategy probably wouldn’t have gotten so far because I would’ve been unsure about what I was saying or how I helped. Having this in place, first, was what made my reputation stick even more.

How about pivoting – can you share the story of a time you’ve had to pivot?
Where do I even begin – hah! Let’s talk about life – this is quite recent because I realized that my business, The Quirky Pineapple Studio, is growing and I needed to make shifts to better support this growth.
Of course, I can go into the business side of things with the pivot – adjusting our systems, investing in better tech platforms for a seamless client and back-end experience, reworking our operations to better support growth, and removing me from the operations… all of those things I’m currently working through and pivoting into with the business.
The biggest thing, however, I think is the life pivot I’ve had to make because of this shift. It’s a life and mindset pivot because I’ve had to let go of stories, beliefs, and mindset blocks that hold me back from truly being a Leader and CEO. It’s been a huge life pivot because I realized that my life cannot revolve around my business, like it did the first 5 years when I was growing. I need(ed) to make really big lifestyle shifts to start believing and acting like MY rest, joy, creativity, and fun was more important than doing things for the business.
I can’t really share the story as if it ended because I’m currently going through it now – I realized that I am not my business, I am not my work, and I also deserve to do fun things outside of work and the business. It’s been a huge learning curve and a big mindset shift because I’ve held onto this identity of business owner for 5 years to get the business to where it is today. Now, my big pivot project is moving into Leader and CEO and prioritizing my vision and joy instead of always giving it to the business. Big changes, y’all!
Contact Info:
- Website: https://thequirkypineapple.com/
- Instagram: https://www.instagram.com/thequirkypineapplestudio/
- Facebook: http://facebook.com/thequirkypineapple
- Linkedin: https://linkedin.com/company/the-quirky-pineapple-studio
- Other: Cassandra personal IG: https://www.instagram.com/cassandratle/ Cassandra personal LinkedIn: https://linkedin.com/in/cassandra-le/es I’m lost, so what? Podcast (Cassandra’s podcast: https://imlostsowhat.podbean.com/
Image Credits
Laura Quintero Photography

