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Ep. 155: How this Expat lived her “American dream” outside of the US and became a remote content strategist with Cassandra Le

In this episode, I speak with Cassandra Le who is the founder of The Quirky Pineapple Studio (TQP Studio), a messaging and content strategy boutique agency. 

She is an award-winning marketing expert, was a contributing author in BRANDING QUICKIES, ranked #1 on Amazon in leadership, and has given workshops in English and Spanish in various countries around the world.

When she’s not working behind her laptop, you can find her exploring neighborhood cafés in Madrid (her adopted home), getting lost in translation in Spanish, or relaxing on the couch watching movie trailers or mukbangs on YouTube!

Listen Below:

 

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Transcription :

Debbie:

Hey everyone! Thank you so much for joining us. I’m so happy to be here with Cassandra. Hey, how are you?

Cassandra:

Hello. Good. How are you? 

Debbie:

I am wonderful. Thank you so much for being here. Can you tell us more about you and why you live an offbeat life? 

Cassandra:

Yeah. So, I am Cassandra. I’m originally from Virginia in the United States and now I live full-time in Madrid, Spain because I fell in love abroad and decided to move to be with the boo. And I started my own copywriting and content strategy boutique agency.

Debbie:

That sounds like what a lot of people would like to do; fall in love and move to an exotic country. 

Cassandra:

Yup.

Debbie:

I know it may sound like a no-brainer, right? It’s like “Okay, you found the love of your life somewhere and you just move there.” But is it really as easy as it sounds because I’m sure you had a lot of things in Virginia: family and friends and all of that. How is that transition like and what did you do to prepare? 

Cassandra:

Well, let me tell you. One, for anybody who does fall in love abroad; It’s amazing and also very frustrating sometimes – “good frustrating”. But I would really not recommend living abroad and then starting a business at the same time, which is exactly what I did because it ended up being so stressful when getting used to the new country and culture that I’m living in. And also the language: I live in Spain so they speak Spanish.

And two, learning the ropes of owning and starting a business but being a different country. So that was really really challenging. And also just deciding to leave my family was a huge thing because my parents are Vietnamese, American immigrants, a family is like a huge thing to us and my family is really close. We always suppose to see each other on the weekends and hang out and this was kind of like, “Oh my gosh! She’s leaving and she’s not going to be here.” 

Honestly, if you fall in love and you want to move abroad, think about it first and talk to your partner. And then, if you want to start a business, also think about it and kind of figure out what you actually want to do and make sure that you can do it, I think, online because I knew I wanted to work with clients overseas. 

Debbie:

Yeah. I think it’s definitely a really important message there: ask your partner first before you move.

Cassandra:

Yes. That’s a lot of conversation we had. 

Debbie:

Yes, don’t just move there and they don’t know. So, when you realized you wanted to start your business abroad, was it something that you already knew how to do or was this something completely different? Did you have any experience and background in copywriting and content strategy? 

Cassandra:

I have been blogging since I was 13 years old. So, I always had experience in social media, blog post writing, copywriting, and everything else revolving online content. And I knew I wanted, in my mind, to be a full-time travel blogger, but I realized that it just wasn’t sustainable for me. And I wanted a way to sell services to people and actually do something or service-based then finding different sponsors.

So, I actually decided that I would switch my travel and lifestyle blog into what it is today, The Quirky Pineapple Studio, and offer services to other service providers. That’s kind of how I did it. I didn’t necessarily study copywriting or marketing in college – I studied Hospitality management. 

And then I kind of have to really sit down and figure out my skill set: what worked and didn’t work and how I approached my processes in my services as compared to other people.

Debbie:

That is a huge leap to take because it’s something that you’ve essentially learned on your own and for most of us, it takes a little bit of time. And for you to do that and actually make it into a business and also moving to a new country, that must have been so overwhelming to not only start a business, something that you are also learning and really making into something profitable, but also, you don’t know the language of the area.

You’re in, really, you’re not familiar with a lot of different places. I’m sure that was a lot to take on 

Cassandra:

Yeah. Also, I had to figure out taxes and accounting in Spain. I mean, figuring out taxes and accounting in the United States is one thing but me figuring out how to do it as a foreigner in a different language was like a whole separate thing. I had to hire help because I just couldn’t do it by myself.

Debbie:

I wouldn’t even know how to tackle that here. As you said, I do hire somebody to help me, I can’t even imagine in a different country. 

When you were starting your business in Spain. What was that process like? Obviously, Google is our best friend, but what are some of your tips for somebody who also wants to do something similar? Is it really completely different? Are there any like tricks that really helped you out to make that transition easier? 

Cassandra:

Yeah. I guess it depends and this is getting into like the nitty-gritty stuff. If you want to be a legal tax resident in Spain, there’s one way to do it. And then if you are a digital nomad or if your location independent and you’re a legal tax entity in your home country, then that’s a different way. But I won’t get into that because I really recommend talking to a lawyer and accountant – don’t take my word for it. 

I would say, one, is having a community around you. When I first started my business, I found a community in the United States in Virginia where I’m originally from, and I really relied on them on, kind of, learning the ropes of starting an online business. I attended lots of networking events, I paid for trainings and resources, and that kind of helped me set up the foundation before I even moved.

And then when I moved, I found different networking groups and communities. There are lots of Facebook groups here in Madrid to connect with other entrepreneurs or online business owners If I just stay home by myself all day, I would be really sad which I was and then I needed like human interaction.

Debbie:

Yeah. I mean, that’s one of the things for us when we’re working remotely. I think it sounds really great: you get to stay on your couch all day, but also you become a hermit. I tell people this all the time, “‘Im literally at home, and whenever I have to either travel for work or even leave the house I get so upset.”

Cassandra:

I thought it’s just me, but that’s me. At first, I was really upset that I was at home and I got like cabin fever and I didn’t really know how to control my schedule and I thought I could just go out and come back in. And then, it was like a mix: I was sad, I was home and I wanted to go out and then, I went out and then I was sad that I was out. And I wanted to be home because I was spending so much time like in the Metro meeting with people that I wasn’t actually doing work to move my business forward like selling and creating things actually. 

So, I just was meeting up and having a social life. That’s great and I needed that but if you want to be a business owner, you have to make money. 

Debbie:

Yeah. I mean, it’s a really hard balance to have because when you own that business, everything that comes in your pocket you are in charge of. You don’t have a boss that’s giving you your payment every month or every two weeks, you’re the one responsible for it.

But I think, for me, it also goes beyond that where I’m just so comfortable in a lot of ways. That it’s just like getting me out now, it has to be something really big. But then when you leave the house, you’re like, “Oh my God! It’s nice to have fresh air. This is awesome.”

Cassandra:

Oh, yeah. There are lots of times where I’m thinking to myself, I wake up and I’m like, “Oh, I should take a walk today.” And I’m like, “Well, I have work I need to be doing.” And then, I end up having to like running errands and I go outside and I’m like, “Wow! The lighting outside is so different from the lighting that just comes through the window.”

You’ll have like this fresh air thing going on and it feels so good. 

Debbie:

I know. I think a lot of people think that when you’re a remote worker or you’re traveling constantly. But for the most part, we usually stay in one place for a long period of time because you also can’t get work done when you’re constantly traveling. At least for my experience that doesn’t usually happen because you always want to experience so many different things when you’re in a new place that work is on the back burner most of the time. 

Cassandra:

Oh, yeah. I completely agree. I went on a digital nomad trip and that’s actually where I meant Andrea of “its a Travel O.D.” and I thought it was going to be amazing. I was going to get a taste of like hardcore digital nomad life where we would move countries and cities each month. 

And then I realized, “Oh my gosh! My body can’t handle this because I am tired. I cannot move each month and then also keep up with client work.” Not just quite work but my own business. Admin things are like creating new stuff for my business. It was just so draining. So I want to keep up and see everything and be a tourist, but then also be a business owner and make sure that my business kept growing. 

Debbie:

Yeah. It takes a lot of time and effort to grow a business. And if you’re listening to this, if you can just imagine what it’s like to be running a business and also traveling at the same time. It’s really tough and it takes a very special person to be able to do that and be able to sustain it in a long period of time. 

Because I think, for the most part, 80% or 90% of the people I talked to really do this for a short period of time and then they settle somewhere for a longer period. Or they travel slowly and it becomes more sustainable. 

Cassandra:

Yeah, I totally agree. That’s why I like having my base in Madrid with my boyfriend and then on occasion, we travel. But then, I also realized that as much as it’s cool to say I’m a location independent business owner, I wouldn’t want to take the business on my travels if I’m going with my boyfriend – that’s a vacation to me. 

Like I need to make the hardcore distinction of when it’s a vacation and like when I’m traveling and working at the same time because styles in which I would travel would change drastically. 

Debbie:

Absolutely. It’s so different and also when I travel for work, it’s not the same because you don’t really get to enjoy it the way you want. enjoy. It’s how your clients want you to enjoy it. So now, even that, even when I travel for work, even when it’s a really beautiful destination, I’m like, “I want to go here for vacation, not for work.”

Cassandra:

Yeah. I feel you on that. 

Debbie:

So, Cassandra, let’s talk about your “what now?” moment. After you decided to leave your life in the U.S. and to dive into a new life with your boo in Spain, we all have that “what now?” moment when we finally take that leap. What was yours like?

Cassandra:

Okay. I think they were multiple because I did the move but then also started the business at the same time. So I had a little bit of like a business “what now?” moment and then also a personal “what have I done?” moment.

So, when I decided to quit my job and move abroad, that was already a big thing personally because my family was kind of like, “What are you doing?” And then coming here, I didn’t know anyone except for the boyfriend. So I felt super alone. And I think it was like one day I was at home by myself in the new house in Madrid and I hadn’t left the house because I didn’t know where to go or who to hang out with.

And I just had a moment where I was like, “What have I done? What do I do now?” And that’s when I just joined a whole bunch of Facebook groups and joined a whole bunch of networking things because I was sick of soaking in my house by myself and being lonely. 

So, that was like the personal side. On the business side, the “what now?”, I think, was when I  realized that my business was going to be functioning based in Spain and it wasn’t going to be like the United States. I had a little bit of a culture shock because even though I mostly work with U.S.-based clients, I’m still living in a different country.

The marketing here is different, how people sell is different, how people run their business is different. And that really shocked me, I was like, “Oh my gosh! What now? What have I done? 

Debbie:

Yeah. I mean it’s a lot of culture shock that you had. So many different things happening and that’s a lot.

Cassandra:

Yeah. Again, that’s why I don’t recommend doing work at the same time.

Debbie:

Yeah. That’s a good advice. How much money did you actually save before setting off to do this? And how are you able to budget it to make it last? 

Cassandra:

So, when I first moved here, I think I had about $12,000 from my full-time job saved up. And then, I had money left in Spain, I don’t remember how much I had. But because I would have lived here before, I even came back as an English teacher. 

So I had a little bit of money. It wasn’t like in the thousand, it was like maybe a couple hundred Euros. And then, actually, what was really great was that my boyfriend was like, “Okay. I know you’re starting a business. Let me take care of everything and you focus on your business.” So anything that I spent was from my savings, but it was all either for business investments or personal things and from the kindness of my boyfriend. 

He actually took care of rent and utilities and groceries for a while until I could actually contribute. 

Debbie:

I think that’s also the beauty of not doing this on your own and you have an extra hand and extra help with this. Because it makes that transition so much easier and you don’t feel like you’re being pressured to do a lot of things that you really don’t want to do as well. 

Cassandra:

Yeah, for sure. I think we had the conversation before I moved and when I decided that I was going to start the business. And we kind of sat down and were like, “Okay. If you’re going to take the business, that means that you’ll probably be rocky in the first few months.” And the first few months went on to be more than the first couple months ‘cause when you’re a beginning business owner, you really are trying to find your bearing. 

So he was just like, “Okay. I don’t want you to have pressure to make money which will ultimately block you from making money.” Then, he was like, “I’ll take care of everything.” Well, everything in the house. And then,I just paid for whatever I needed to pay for.

That is very generous and I do realize that puts me at an advantage from other business owners, but I do want to say like, “That was the reality and that was my reality.”

Debbie:

Yeah. And honestly, you really do need that. And it’s a really great thing to have a supportive partner like that. Not everybody can have something like that. So however help you can get I say take it.

Cassandra:

Yes. If they offer it and you think it’s a good fit, take the help because it is a long road -this business owner thing.

Debbie: 

And also, I want to touch up about you and your communication with your boyfriend for anyone who has a significant other who wants to start this lifestyle. I mean, it’s a really tough road to be in and it was really nice for your boyfriend to be able to understand that. Especially since you also uprooted your whole life to be there for him. 

So, how would you say made this conversation really fruitful and also really helpful for both of you? Especially when you’re both starting this new life together and in this type of situation.

Cassandra:

I think any conversation about money is always very tricky. stay Especially with a significant other, your kind of like, “Oh my God. This is kind of like a big conversation to have with somebody else because you’re going to be sharing money.” It really ended up being like, “I’m still trying to be as clear as possible and kind of setting expectations and boundaries.” 

I’m sure there are lots of times where both of us were kind of frustrated with the situation. I got frustrated because I couldn’t contribute when I wanted to. And of course, there were times where he was like, “Maybe you are investing too much back into your business,” and we don’t know if it’s actually providing a profit or getting a return from it.

So, we’ve had conversations like that. And I think we just ended up having to talk about it at the moment and not the kind of like wait and let it build up. So I guess something happened then, we would actually need to approach the situation. And also, I didn’t, ever, go to my boyfriend and say, “Can I do this?”, or, “Can I do that? It was never like asking him for permission ‘cause that’s kind of weird.

But it was always like, “Okay. Just so you know, this is what I’ve decided to do. What is your opinion?” And he would share his opinion and then, in the end, I decided what I wanted to do with any investment or anything like that. 

Debbie:

Yeah. It’s just getting input instead of you asking for permission. I think that’s a really good way of putting it and you’re still owning what you’re doing. But you also need that extra mind to tell you if what you’re doing is in the right direction. 

Cassandra:

Exactly.

Debbie:

So, it’s always good. It’s like brainstorming for couples.

Cassandra:

Yeah! Couples for the win.

Debbie:

Exactly. So, now, Cassandra, what would you say is your secret sauce for making your business successful right now? 

Cassandra:

Okay. So, a few things. I think going into the secret sauce, a couple of ingredients: one is investing in your education and in mentorship, I think that’s huge. I’ve invested in, I think, four different business coaches and one life coach actually who have helped me kind of just figure out the next step to make sure that my business grows and is profitable and actually sustainable for the lifestyle that I want to live – my own offbeat lifestyle

And then, another one is to really get feedback from your clients or if you don’t have clients yet, get feedback from people that you would want to work with. That has been a huge thing where, as a creative or as an entrepreneur, you’re just brainstorming in your own head and you try to come up with things that you think would be fabulous and absolutely amazing. 

But if you don’t take it and ask for feedback from people that could actually buy your services or your product, then you’re kind of missing the mark. So, asking for feedback constantly from my community, from my audience, from potential clients, or even people who have never worked with The Quirky Pineapple Studio or myself, but have deemed themselves like our brand ambassadors has been super helpful.

Debbie:

Having that feedback is like another way of brainstorming. You either take it or leave it, but at the end of the day, it’s really good to be able to understand what you’re target clients are thinking about what you’re actually giving them. So, that’s a really great tip for us.

Now, when you’re living abroad, Cassandra, what type of international insurance are you able to use? 

Cassandra:

I actually have universal healthcare here. So, I have a residency card in Spain now and that actually put me under the Spanish Healthcare System. I don’t know what other people are using but you can always buy private health insurance to live here. But I only know about the public health care system.

Debbie:

Well, that’s a great thing about certain countries is that you do get that Healthcare System but there are so many different ones that don’t give you that. Specifically, in parts of Asia or in Central and South America and even in the U.S. we don’t get that.

Cassandra:

Leaving the U.S., it’s been an interesting thing to learn about Universal Insurance. 

Debbie:

It’s true. It’s like finding insurance when you’re in a steady location, like the United States, is hard enough, but it’s even harder when you’re always on the go and always on the road. And I’m always confused by so many of the requirements that they have and I need so much help to get through the process of even claiming your insurance. 

That’s one of the hardest things. It’s like you could never get anyone online or on the phone and that’s why I’m really glad that I’m partnered with Integra Global who has the most incredible customer service. They have 24/7 help. You can submit a claim through their app and your claims are managed by their in-house Global expert team who are always there to handle any issues which mean less stress and panic because I always do that. 

Cassandra:

Yeah. I get it because whenever I fly home, I don’t necessarily have health care anymore because I’m covered here. And I’m also over the age of 26, so my parents aren’t going to keep me in the healthcare system.

Debbie:

Exactly. In the U.S., once you’re over 26, they don’t do that anymore. So if you guys want to learn more about Integra Global go to IntegraGlobal.com for more details. Their coverages are really excellent and they have it in so many different countries that are not covered by universal healthcare like Cassandra is at the moment.

So, when she comes back to the U.S., it’s a different story. When you go to Mexico or somewhere in Asia, it’s totally different.

Cassandra:

Very, very different. I am just within the system. When I leave, I am not in the system anymore. 

Debbie:

I mean, it’s pretty crazy. A lot of times you don’t think about that but such an important thing to do especially if you’re traveling for a longer period of time. It’s just a great way to really secure yourself.

Now, let’s fast forward to 50 years from now and you’re looking back at your life. What legacy would you like to leave and what do you want to be remembered for?

Cassandra:

This is kind of a tough one. A legacy that I would like to leave is through copywriting and content strategy specifically. I would love to leave a legacy that really has impacted my audience. Not just clients but like anybody who follows me or The Quirky Pineapple Studio online.

To be confident in their voice and to be confident to use their voice and share about their successes and achievements without feeling ashamed, nervous, or embarrassed about it and just really owning their power. That’s like the biggest thing that I would like my legacy to be.

Debbie:

That is a really great one.

Cassandra:

Thanks. And then being remembered for that, but also just being remembered for somebody who kind of lived life to my fullest capacity and kind of didn’t take any crap from anybody. I think someone who is just having fun with business and travel at the same time. I don’t want to be just remembered for business things, I want to be remembered for being a full, well-rounded, developed human being.

Debbie:

There’s a lot of different things in life aside from our business. I know it takes up like 70% of our time but it’s not the only thing.

Cassandra:

Exactly. There are other things but my business is amazing. I do work on it quite a bit.

Debbie:

Well, especially when you love it. It doesn’t feel like work because you always want to be doing it ‘cause it’s so much fun and you’re always learning. 

Cassandra:

Yeah. 

Debbie:

What are you currently working on that is really exciting to you? 

Cassandra:

So, I actually just launched a 4-month mastermind called “Use Your Voice” and it’s for service-based business owners who want to increase the impact that they make either helping more people with their services or even just making more money in their business. I’m super excited because I’ve never actually been a mastermind before and this is the first time I’m launching something like this. 

But I just feel like, over the past two years that I’ve run The Quirky Pineapple Studio, I was experimenting and like testing out different services and packages and this is the first time, like finally this year 2020, that I feel super aligned to the services and the type of work I’m offering. And I feel like this mastermind and everything else that I’m doing just makes sense. 

Like I am not trying to like squish things together anymore. It just all flows really really nicely.

Debbie:

Don’t you love it when that happens?

Cassandra:

Yes. I thought it was flowing before but I clearly didn’t know what “flow” meant because this is a completely different feeling. Like I don’t feel like I’m pushing something. I don’t know if you ever felt like this where you feel like it’s flowing but what you’re doing is just kind of like forcing it.

Debbie:

I always feel that when I’m not worrying about something and I just focus on what I need to do that it always comes. I think that if you are thinking about it too much as you said, you’re forcing it too much, it actually leaves you. It’s like a magnet and you’re not attracting it anymore because you’re trying to force it. I definitely understand what you’re talking about. 

Cassandra:

It’s like overthinking that you’re like, “This is going to work,” and then you try and plan out every little single thing. I love planning but like sometimes you really just need to relax. And then, like you were saying, when you relax, things start coming to you.

Debbie:

And then, take action. That’s the thing, right? 

Cassandra:

Oh, yeah. Don’t forget that. 

Debbie:

Because when you’re overthinking something it actually stops you from doing what you need to do. And I think sometimes it’s like, “Think about it!” Usually, your first instinct is the best one. So, just go for it, trust yourself, right?

Cassandra:

Yeah. That’s a huge one. I think if you are an entrepreneur, a solopreneur,  or solo business owner, honestly, trust your instinct – listen to your gut. It is most of the time, probably 9 out of 10 or 99.9 out of 10, right.

I got into so many situations where I’ve ignored my gut and my intuition and then I’m like, “What have I done?”

Debbie:

Yes. That’s always the case for the most part. It’s like, “Why did I do this? Oh my gosh.”

Cassandra:

“I should’ve listened to myself.”

Debbie:

I know. Now, if our listeners want to know more about you, Cassandra, where can they find you?

Cassandra:

They can find me on my website which is thequirkypineapple.com or on Instagram, you can follow the business account which is @thequirkypineapplestudio, or if you want to follow my personal account @cassandratle.

Debbie:

Perfect. Thank you so much for being here. I really appreciate all of the tips and tricks that you gave us.

Cassandra:

Thank you so much for having me, it was a lot of fun. 

GET THE EXTENDED INTERVIEW WITH CASSANDRA WHERE SHE SHARES HOW TO BECOME AN ONLINE COPYWRITER


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Show Credits:

Audio Engineer: Ben Smith


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