Maddie Orlando Talks Being in the Public Eye, Launching Artless Forever, and More

Culture

You probably know Maddie Orlando from her Sister Diary podcast with her sister Lauren. Or maybe from her brother, Johnny Orlando, who's Gen Z's social star. And let's not forget about her perfectly curated Instagram feed.

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Either way, Maddie Orlando is a rising internet figure, and she's writing the next chapter of what's to come next.

The Teen Magazine had the chance to talk with Maddie about her relationship with family, the future, and her recently launched brand, Artless Forever.

On Growing Up

What was your childhood/upbringing like?

I grew up in a small city outside of Toronto, Canada. I would describe my childhood as idyllic — I was very sheltered and grew up alongside people who were similar to me, which I think gave me a pretty singular view of the world.

I never really considered challenging the traditional education or career path. I planned to graduate from high school, go to university and get a job. I actually thought that I was going to go to law school.

My family has always been very close, so I spent a lot of time with my parents and siblings growing up. Before about 2012, we had a very “normal” life. I went to school, danced competitively after school, and skied on the weekends during the winter.

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In December 2011, my brother started posting YouTube videos, which were all of our first experiences with social media and the entertainment industry.

Being Widely Known Online

Your family is pretty big in the public eye—how’s that been like?

It has definitely been interesting! Until I graduated from university in 2018, I mostly just observed Lauren and Johnny’s (my younger siblings) careers in the public eye.

I was worried about what people at my school would think if I pursued a similar career myself, but I always thought that what they were doing at such a young age was admirable.

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Since then, I have gotten much more comfortable being a public person and sharing my life online. It definitely comes with certain challenges, though. People on the Internet can be mean, judgmental, and presumptuous.

However, I’d absolutely say that it is more positive than negative. One amazing thing has been the opportunities that have come with it. We have been able to travel, go to events, meet incredible people, and start businesses because of the platform that we have.

Sibling Dynamics

Are you close with your siblings? What have you learned from them and what have they learned from you?

I am super close with my siblings. We spend so much time together… maybe even sometimes too much!

I think my family dynamic is interesting because there is a big age gap between me and my sister, Darian (23), and our two younger siblings, Johnny (18) and Lauren (16). I like to think that I give am able to give them advice about things that I have already gone through, like school and friendship and relationship drama.

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Lauren has told me that the best lesson I’ve taught her is perspective. As a teenager, I remember thinking that everything seemed like such a big deal. The little things felt like the end of the world and I really let them stress me out. I always remind Lauren that high school is just a tiny part of her life and there are so many amazing things that await her in the future.

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I have learned a lot from all three of my siblings as well — both practical skills, like video editing and Photoshop and about hard work, creativity and not caring what others think about you. They showed me that challenging that normal path that I mentioned is both possible and rewarding.

The Sister Diary Podcast

You started a podcast with your sister Lauren a couple of years ago. What made you two start recording?

Yes! We started The Sister Diary in July 2019. To be honest, it was kind of created on a whim, but there were a bunch of reasons behind it.

Lauren was unsure of what to post on YouTube and how she was going to evolve online and I was obsessed with podcasts. Also, despite having an eight-year age gap, we thought that the conversations that we had in real life were somewhat interesting and had the potential to provide value to our audience.

Now, I think that the age gap is what sets our podcast apart. Lauren is able to provide a teenager’s perspective on the topics that we discuss, and I am able to evaluate them as someone who has been through a lot of them already and has come out the other side.

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We didn’t plan or overthink the podcast. We decided to do it, launched that week, and adjusted as we went, which I think has been crucial to our success.

The podcast has been so fun and serves as a way for Lauren and me to catch up and chat every week, which is really special. I think it has also allowed us to connect more sincerely with our audiences as well. You really get to know someone when you listen to them talk for an hour a week!

On Artless Forever

Your brand, Artless Forever recently launched—what inspired you to start it?

I am so happy Artless is finally out! I was inspired to start my own brand almost two years ago after I graduated from university and was trying to figure out my career path.

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I have always been interested in fashion and obsessed with clothes, and above all, wanted a job that allowed me to work for myself. I saw this as the perfect way to utilize the audience that I had on social media (which was largely thanks to my family) and find my place in the entertainment industry in my own unique way.

Creating The Brand

How were you involved in the creation of Artless Forever? What responsibilities did you have? How did the process flow?

I’m involved in the entire process, from design to fulfillment. We’re still a very small company so I wear many hats!

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My dad is also my business partner, which has been great. He has lots of experience with entrepreneurship and business in general, so he is able to solve some of the major challenges that we have experienced along the way.

The first thing that I did after deciding that I wanted to start my own brand was Google “how to start a clothing company”. I really didn’t know anything about the process, so extensive research was important.

I figured out that I had to find a cut and sew manufacturer in Los Angeles that could help us with development and production. I set up a few meetings for my dad and me, and eventually, we decided on one in downtown LA. I worked very closely with their team on the development of the line.

I first created tech packs for my designs, which are basically documents that contain all of the necessary technical information about each garment. We then thoughtfully sourced fabrics and trims for each style, and I was responsible for reaching out to the fabric mills and trim stores to order the ones that we chose. The cut and sew team then created patterns, marked and graded the garments, and produced samples.

I was my own fit model, which meant I tried on the samples and made any necessary revisions to the sizing and construction. This was a very cool moment — it was the first time I saw the clothes in real life. Most of the styles were amazing and ready to move into production, but we actually scratched one style entirely because it didn’t turn out as I envisioned.

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In early March 2020, after over a year of development, our samples were finally approved and I signed the production contract. Three days later, the factory shut down for four months because of COVID-19. This was a frustrating, unforeseen challenge that set our launch back a few months, but ultimately it was worth the wait. Once I received the samples, I organized e-commerce and creative campaign photoshoot in Toronto.

Before we launched, I was responsible for finalizing all of the tiny details that you would never think about, like buying poly bags, hang tags, sewn-in labels, and care instruction tags. My dad and I also started working on our marketing and advertising strategy and hired an agency to assist with paid promotion. We finally launched on February 1, 2021!

Artless Forever in 5 Words

If you could describe your brand in 5 words, what would they be?

Elevated, effortlessly cool, constantly evolving

The Fun Part & The Hard Part

What was the most fun thing about starting the brand, and what was the most challenging?

I love that having my own brand allows me to be creative. I enjoy every element of the creative process, from design, branding, and marketing, to posting on social media.

To be honest, curating our Instagram feed has been a great creative outlet for me. It’s such a fun little project. I also love the design process. I’m working with an amazing, talented designer now who really understands my vision and is incredible at helping to bring it to life. We’re currently in the process of creating both our spring/summer and fall/winter collections, which I am so excited about.

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Marketing and branding are also super fun. It has been a cool challenge for me to continue to establish the Artless “world” — the lifestyle that is associated with the brand.

As we evolve, I want Artless to be about more than just the clothing itself. I want it to be a brand that stands for individuality and self-confidence, advocating that the coolest people are those who simply embrace and live as their most authentic selves.

There have also been obstacles and mistakes along the way. I think the initial pre-launch phase was the most frustrating because everything seemed like it was taking so long, and I didn’t have a clear enough grasp on the process to really predict the timelines. I like to think that it will be easier and quicker next time we go into production!

Projects Coming Soon...

What projects do you have coming up? Where do you see yourself in 5 years?

I’m currently working on a project with all three of my siblings. It’s the first thing that we’ve really done all together and I am so excited to share it. I hate when people talk about “secret projects” but unfortunately I can’t say much more at this point!

In 5 years, I will be almost 30 (!!!) which is absolutely insane. I am not really a long-term planner and I don’t know what the future holds, but I hope that at that time I am successful, healthy and fulfilled.

Advice From Maddie

What advice would you like to give to everyone?

Your potential is endless and you can become anyone that you want to be in this life. Don’t limit yourself to who you think you are, the career that you think you should have.

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I think that fulfillment comes from living in alignment with yourself, not with the status quo.

10 Quick Q’s with Maddie

1. What is a personal favorite piece from Artless Forever?

The silk dress in Neptune! And everything we’re designing for SS21.

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2. Shoutout to your besties—who are your ride-or-dies?

I have amazing friends that I made both in school and over the past few years.

My friends Abbey and Syd are definitely two of my very best friends. We always have the most ridiculous, hilarious time together.

3. What is your favorite childhood memory?

Traveling with my family.

4. Guilty pleasures: songs, movies, TV shows?

I don’t really listen to music or watch movies or TV, which I think makes me really weird.

I’d say my guilty pleasure is sugar. I love dessert.

5. Where is your happy place/Your favorite place you’ve traveled to?

I love Los Angeles. I don’t know if it’s my happy place, but I feel very alive there.

My favorite place I have traveled to is a tie between Singapore and Amangiri. I just went to Amangiri, a resort in Utah, this past January and it was one of the most beautiful, tranquil places I’ve ever been in my life.

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6. Your favorite clothing brands?

Are You Am I, Danielle Guizio, Jacquemus

7. What are your favorite hobbies?

I love health, wellness, and fitness.

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When I have more time on my hands, I want to study to become a holistic nutritionist or something in that field.

8. If you were a candle, what fragrances would you be and why?

I am obsessed with eucalyptus and sandalwood.

They are strong, earthy, powerful fragrances… That resonates with me.

9. Something about you that most people don’t know:

I used to want to be a writer when I was younger and would write novels for fun.

10. If you had nine lives, what would you be or do in each one?

If I had nine lives, I’d want to be a fashion designer and entrepreneur (like in this one!), a nutritionist, doctor, travel blogger, animal rescuer, astronaut, Charli D’Amelio, entertainment lawyer, and Kendall Jenner’s stylist.

Keep Up with Maddie

To keep up with Maddie, make sure to give her a follow on Instagram @maddieorlando, and Artless Forever @artlessforever.

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Sophia Zhang
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Sophia Zhang is currently a high-school sophomore residing in Chicago, fifteen in age but five at heart. Besides writing, Sophia spends her days playing piano, volleyball, or her favorite TV show on Netflix.