Maddie Orlando

Branding, Marketing, Fashion and Podcasting

Maddie Orlando

Location: Toolsy Headquarters
Date: 7/13/2020
Profession: Founder, Artless & The Sister Diary Podcast

Q & A

Tell us about yourself. Who are you and what do you do for a living?

My name is Maddie Orlando and I am 23. I was born and raised in Toronto and now usually split my time between Toronto and Los Angeles.

I lived a pretty normal life until about 2014 or 2015, I went to a normal high school, then to university and planned on going to law school after that. My younger siblings are in the entertainment industry and when I was in my first year of university my family moved to LA so that they could pursue their careers.

That was kind of my entrance into the entertainment industry as well. Since that time, I moved into the social media space, created my own YouTube channel and started a podcast with my sister, Lauren. I have also been working on a clothing company for the past year, which is called Artless.

Lauren and Maddie Orlando

What’s your backstory and what led you to starting your clothing company and podcast? What drives you?

For most of my life, I would say I followed a pretty traditional path in terms of education, but I always wanted to do something entrepreneurial. I am, and always kind of have been, driven by a desire to succeed.

Even when I was in elementary school, I feel like I was always competing with my classmates. All my friends at school were super smart and it definitely encouraged me to continue to push myself. When I was at Western University, I was kind of frustrated because I didn’t know what I wanted to do with my degree. I followed the path that I thought I was supposed to, but quickly found myself asking, “What is the point of this?”

I lived in Canada during this time and studied media studies, which as a program was very general and theoretical. In the city I lived in, social media wasn’t really accepted as something you could do as a career. People thought it was weird if you had a YouTube channel or took your Instagram too seriously.

I was definitely worried about what people would think about me and I think it held me back from pursuing anything that was unconventional at this time. 

Maddie Orlando in college

After my family moved to LA, I realized that working in the entertainment industry could be great opportunity for me to do something different. My siblings knew what they wanted to do from a very young age. My brother is a singer and my sister has made YouTube videos since she was 8 years old, so they had their “thing”. Once I graduated, I realized that I had to find a lane for myself. 

When I was in high school, I graduated grade 12 a semester early and worked for my dad, who’s a lawyer. This was a traditional, 9-5 desk job. In the best way possible, I think that working there motivated me to find a career path that I was truly passionate about; something that was exciting and unique, more along the lines of what my siblings were doing. 

My parents always encouraged us to do our own thing. Since I was little, my dad has always told me “never work for someone else if you don’t have to”.

I always have that in the back of my mind. He’s very entrepreneurial, which has helped me realize the possibility of starting a company or doing something different. Another thing he says is “the only way you’ll ever fail is when you stop trying”.

I feel like that helped to instill the confidence that I needed to just try to do my own thing, and I’ve been so lucky to have my parents’ support.

Maddie Orlando Parents

After graduating from university, it took a few attempts for me to clearly define what my path would be. I’m very interested in health and fitness, so at first, I thought that I wanted to do something in this space.

My plan was to create a gym/health club in LA, kind of like a combination between Soho House and Equinox. I also wanted to partner with wellness influencers who have an online presence, but no physical space to connect with their followers. The gym would be a place for them to teach pop-up classes, hold live events, and sell their products.

After creating a business plan and running some numbers, I quickly realized that a gym is a hard business to start and is often not profitable, especially when rent for retail space in Los Angeles is so expensive.

I took a few business courses in school and my dad is very business minded, so he helped me out a lot with creating these plans. I decided instead to start with e-commerce because the startup costs are much lower and it’s a growing business. It’s 2020 – people are shopping online and moving away from retail.

Ultimately, my dad and I partnered on an online apparel company called Artless. The first product that we created was influencer merchandise. My brother and sister have pretty large social media audiences and have sold merchandise for years.

Previously, they partnered with a company who assisted with designing, printing, selling and fulfilling the items. All the influencer really does is promote the items to their followers on social media. I was my sister Lauren’s manager for a few years and was responsible for communicating with the merchandise company they were partnered with, so I was pretty familiar with how the process worked.

My dad and I recognized that taking over the production of their merchandise would be a great way to enter into e-commerce, and that we could provide them more profit and value if we did it ourselves.

Maddie Orlando Merch

We started off selling hoodies and T-shirts because I knew that’s the type of merchandise that most artists and influencers sell. I researched everything online and having worked with merchandise companies before, I had an idea of what brand of blanks they used, Gildan for example. So I would Google, “where do I find Gildan blanks online?

We bought hundreds of blank hoodies and T-shirts as our starting inventory and stored them in our garage in Los Angeles. My sister, Darian, is very artistic, so she designed a logo for Lauren and Johnny.

We also had a young graphic designer who we actually found on Instagram help create some of the artwork. Once everything was ready to be printed, I brought the blanks and art to a printer in downtown LA.

The whole thing was quite a process at first because we were learning the most efficient and effective way to do everything, but we have it down now. Recently we’ve been focusing on creating more merchandise products and developing a larger customer base. I’m lucky to be connected to a lot of influencers in LA, which has been great for the business. 

At the beginning I was basically doing everything by myself. I communicated with the designers and printer, dropped off the boxes of merchandise, and fulfilled everything. I think when you start a business, you kind of have to play every role.

How did you go from selling merchandise to getting to where you are today?

The merchandise that we created was a great start to our company, but I always knew that I wanted to make actual clothing as well. The process of making merch isn’t that creative because you’re just printing a design on a blank piece of clothing.

I wanted to create custom, cut and sew pieces that I would actually wear, so I did more research and I found somewhere in Los Angeles that could help with the process. My dad and I set up a day and interviewed a bunch of different apparel companies, to find one that would be a good fit and also to learn more about the process of making clothes. 

We started with development in April 2019. At this point, I had no real concept of what I was doing. I was constantly Googling terms that I didn’t understand and tried to do as much research as possible, but mostly learned about each step of the process as we went along.

I was like, I’ll just pretend like I know what I’m doing and figure it out eventually.  We experienced delay after delay and it took almost a year to get my first round of samples, which was pretty frustrating.

In the future, I think I’ll be able to skip this long period of development because I have a better grasp on the intricacies of the process. I’ve learned so much about fabrics, patterns, trims, where to get clothes made etc

Can you tell us a little bit more about the process involved in making your own clothes?

The first thing I did was actually design the clothes. I knew that I wanted the first collection to be simple, neutral and casual, but I had to get my ideas on paper. I settled on six styles that I wanted to release in the first drop – a tee, tank top, silk dress, oversized unisex hoodie, tennis skirt and jogger pants.

Next, I found a graphic designer on Upwork to help me complete my tech packs, which are basically technical drawings of the clothes you’re going to make. I explained to her how I wanted these pieces to look and feel, and she made a digital drawing of them (still not entirely sure how she did this or what a tech pack is for!). I brought the completed tech packs to the cut and sew company.

Next, we sourced fabrics and trims. I worked with someone at the cut and sew who recommended a few different fabric options for each piece for me. I brought her some of my favorite clothes and we looked at what fabrics they were made of as well.

Together, we decided on fabrics for each style. She connected me with the different textile companies and zipper and trim stores in Los Angeles and I reached out to place orders for sampling. 

Sampling is the next step in the process. The cut and sew makes three versions (samples) of each style. These are all in one size, the sample size. I received my first round of samples in February 2020, ten months after starting the development process.

I was my own fit model, so I tried on the samples and made sure I liked how they fit on my body. I made minor adjustments to each piece so that they were perfect for production. 

Once the samples are approved, they are graded from the sample size (XS) to all of the other sizes. A production marker is created, which is basically a template for cutting the fabric during production.

Our production was approved and about to begin right before COVID… literally on March 13. Obviously, there has been huge shutdowns and delays in every industry, and the cut and sew and the manufacturers in LA were closed for a few months. They just reopened a few weeks ago, so I’m super excited to finally begin.

Maddie Orlando Favorite Style

Through starting your career, have you learned anything particularly helpful or advantageous?

I’ve learned that you really have to fake it til you make it in the beginning. Even if the entire process isn’t clear to you, you’ll figure so much out just by going through the motions.

I also learned a lot in University and it was a really great period of time for me to mature and figure out what I wanted to do with my life, but I don’t think it’s always necessary. I’ve learned much more about what I’m doing now by actually doing it.

How do you find the courage to take on projects you know nothing about?

I’m so lucky to have support from my parents. As my partner in Artless, my dad provides me with business advice and guidance and has passed on lessons that he’s learned from running his own business.

I also think that when we created the company, I was in the right frame of mind to feel confident about it because I didn’t really have anything to lose. I thought to myself, let’s try this out and see how it goes… worst case scenario I can go to law school as I had originally planned, or get a traditional job.  

I’ve also found confidence by learning from successful people. I think the Internet, podcasts and social media are great because they allow you to gain insight from people who are not necessarily in your immediate circle.

Hearing someone else’s perspective can really help shift your mindset, especially if you’re doing something a little out of the ordinary. I like listening to the stories of successful entrepreneurs and business owners because it shows you that it’s possible for you to achieve that type of success as well. This can help to eliminate self-doubt. 

I think it was harder to take risks when I was in school because of what was considered ‘normal’ by the people around me. I cared about the opinions of others and constantly looked around to see what everyone else was doing. It definitely took me getting out of that place, both physically and mentally, to change that.

Since then, I’ve tried not to let the fear of failing hold me back, but obviously sometimes I’m still like, “What am I doing?”.

Where did your podcast come from? What do you want to accomplish with it?

I started a podcast called The Sister Diary with my sister, Lauren, last summer. At the time, I was only really using Instagram, which is a very surface level platform. I felt like the people who followed me didn’t really know anything about me.

I wanted to find an outlet where I could be vulnerable and share more of myself. I tried YouTube, but talking to a camera and filming every moment of my day didn’t really feel natural to me.

I love listening to other people’s podcasts and I much prefer talking in a mic than filming myself talking to a camera. I knew that podcasting would be the perfect platform.

When we launched, Lauren was only 14. I saw an opportunity for us to reach a demographic of young people who didn’t really have much audio content that was targeted towards them.

Lauren and I also have an eight year age gap, which is a unique element of our show. We talk about a range of lifestyle topics that pertain to teenagers and young adults. Our tagline is, “we discuss anything that you’d share with your own sister.” We honestly want to make our listeners feel like they are part of our family. 

I had to convince Lauren to actually get in the studio and record the first episode. We were in LA at the time, and I found a studio on Google and decided to just book it. Lauren’s the type of person who wants to plan everything, to be super prepared and for it to be as perfect as possible.

I’m definitely more impulsive. When I have an idea or want to do something, I just jump into it right away. I told her that if we didn’t like the episode, we wouldn’t post it. That first day, we ended up recording two or three full podcast episodes.

They weren’t even that bad, and we posted them all. We have definitely adjusted and improved since then, but I’m so happy we launched when we did. 

The goal for The Sister Diary has evolved over the past year. At the moment, we’re trying to find a balance between delivering content that is both relatable and aspirational.

We really want to show girls that everyone goes through the same experiences and challenges in life. Personally, my goal is to share some of the things that I’ve learned, and talk about things I wish I knew when I was a teenager. These discussions have really helped us build a strong community. 

Another goal for Lauren and I is to feature a variety of perspectives and amplify a wide range of voices through the guests that we have on the show. We’ve learned so much from our guests and love to pass on their stories to our audience. Of course we talk about light, fun topics like fashion and skincare, but we want to continue to also delve into more important issues.

What’s it like working with your family?

It’s interesting for sure. We’re all super close and I spend more time with my family than most people my age. It’s nice to know that they always have my back and will support me in whatever I do. I also learn a lot from them, even from my younger siblings. We have outside management now, but for a long time we kept everything work-related within our family, which was nice. 

As you can imagine, our family dinners are more like business meetings. When we’re all in Toronto, we sit down for dinner and talk about brand deals, social media, TikTok. It’s funny.

Maddie Orlando Siblings

How would you say you differentiate yourself from other clothing brands and podcasts?

I think our podcast is unique because of the eight year age gap between Lauren and I. It allows us to talk about topics from two totally different perspectives. I feel like it helps us speak to a young audience. Lauren can relate to our listeners, and I can speak to them as a person who has already gone through all of those experiences. 

When I started my clothing brand, I knew I wanted to make clothes that are different than what’s already available. I also wanted it to reflect my personal style. I personally love mixing masculine and feminine elements in my wardrobe, and comfort is always a priority for me. I am also very into streetwear, but these brands are mostly targeted toward men and don’t really fit me properly. Artless is a feminine streetwear label, blending oversized, edgy, menswear-inspired pieces with delicate silk and feminine silhouettes. 

I’ve been working on the brand for so long and I’m so excited for it to finally come out. I’m sure it will continue to change and evolve as we release future collections.

To what would you attribute your success thus far?

I would attribute my success thus far to my ability to take action without being held back by the possibility or fear of failure. There have been many times where I wasn’t sure what I was doing or my path wasn’t entirely clear.

I think my impulsivity in these situations really helped propel me on my path to success. If I had waited for the perfect time to launch, I never would have released the podcast or started my clothing company. 

When it comes to social media, I think success comes from consistency. You have to post content that feels authentic to you, and do so on a regular basis.

I also think it’s important to pivot according to new trends and apps that come out. My younger siblings were obsessed for TikTok for months before it was super popular and at first, I thought I was too old for it. I probably still am too old, but I have been posting videos there because that’s where people’s eyes are. It’s the hot new app, and in order to maintain success, you have to be able to adapt. 

I think the last thing that has contributed to my success is allowing myself to be open and vulnerable online. I’m not naturally an over-sharer, but I’ve found the more that I do share with my audience, the more they feel connected to me.

We always get the best podcast feedback when we are open and honest and speak as if we were talking to a friend. People will DM us and say,“I loved that episode so much because you guys were so real”. I think being your true self is always the best thing. Stay in your lane and don’t compare yourself to others, it’s a waste of time. 

My definition of success continues to change. When I was younger, I thought that I just wanted to make a lot of money, and that’s all that it would take to be successful. But, I’ve since realized that you can be the wealthiest person in the world, but if you don’t like yourself or don’t like what you’re doing, you’ll never feel like you’ve succeeded.

I also started to get into the habit of saying “I’ll be happy when ___”… when I make a certain amount of money, when I live in Los Angeles full time, when I get x amount of followers on Instagram.

Now, I’m focusing on being happy right now, even if I feel like I’m not successful yet or that I still have lots of work to do on my business.

Success to me is living in a state of gratitude and being blissfully dissatisfied with life. I didn’t make that term up and I’m not exactly sure who did, but I think it’s a great way to describe the feeling I want to have.

It basically means being happy, grateful and able to enjoy every small moment of life, while also constantly striving to be better. I’m a very achievement oriented person so hitting targets or reaching goals does make me happy. 

How do you set goals for yourself?

I certainly don’t feel like I have done enough to say I’ve been successful in my profession. But what has worked for me in making certain things turn out successfully was making fear a friend, working I journal in the morning, which really sets up the day and allows me to clear my mind.

I notice a huge difference in how I feel and what I accomplish when I set aside time in the morning to reflect and plan for the day ahead. In my journal, I write down a to-do list and then anything that I am thinking about at that moment.

Once it’s on paper, I don’t have to think about it anymore. I also will rewrite my big goals, the things I want to achieve in the next year or so. Then, I’ll make a list of things I can do that day to get closer to achieving them.

Goals are made of tiny sub-steps that can be accomplished over time.very hard towards my objectives, and trying to be as intelligent as possible in the decisions that I make.

What accomplishment would you say you’re most proud of so far? Why?

I spent a lot of 2019 in Los Angeles by myself. I would say that is one of my biggest accomplishments so far. I made the decision to fully pursue Artless and I knew that in order to do so, I had to be in LA.

It was really uncomfortable at first because I didn’t know anyone and spent a lot of time alone there. There were times when I questioned what I was really doing and felt like I didn’t fit in.

I was happy that I stayed there for so long and didn’t immediately run back to Toronto. I feel like pushing through that and not going back to where I was familiar and comfortable is my greatest accomplishment so far.

What was the biggest challenge you’ve had to overcome? How did you go about overcoming that?

Adjusting to life in LA and having to meet new people there was definitely a challenge for me. Like I was saying before, I felt a little lost at first. I wasn’t always happy.

I discovered that the city is much less mystical and glamorous than it appears on the outside. I overcame this challenge by reminding myself of what it would teach me and how it would pay off in the future.

I knew that I would never achieve the things I wanted if I didn’t push myself. I think any period of growth feels uncomfortable at the time, but when you’re on the other side of it you are so happy you stayed with it. 

Also, the process of developing a clothing line has been a huge challenge for me. We experienced so many delays and made a lot of mistakes along the way, which was tough and extremely frustrating at times.

I consciously adjusted my perspective toward this challenge and tried to find something positive that I could take away from it. Mistakes are great teachers. I learned so much about working with a team, how to act in order to be respected in the business world, and about the apparel industry in general. 

COVID was particularly tough because it felt like we had made great progress toward launching Artless at the start of 2020, but then everything shut down and our production came to a complete halt. I hate the feeling of being at a standstill.

During this time, I really learned that the only thing that is in my control is my reaction to events. I had to change my perspective.

How are you feeling today? What’s your ultimate goal right now?

I am feeling good! There was a very long period when we were all stuck at home where I was constantly asking, “what is going on in the world” and “how are we going to recover from this”? I’m happy that life is starting to go back to normal and I have hope that things will continue to get better. 

My ultimate goal is to have a successful official launch of Artless. Once that happens, I am looking forward to continuing to release new styles. I want to keep the momentum going. I also want to move to LA full time and get my own place there. I’m so excited to decorate my own apartment.

Software & Tools:

What software/platform/tools do you use for your business? What do you use each for?

Instagram & Tik Tok: In terms of social media, I try to post on these platforms fairly regularly. TikTok is blowing up right now, so that’s been a priority for me.

I’m in the process of finding my niche on TikTok. I don’t think you have to be a comedian or an amazing dancer to do well on the platform. I try to post on social media in a way that feels natural and authentic to who I really am. Over time, I’ve been able to figure out the type of content, photos, and outfits that actually represent me best. 

I have a manager at an agency called DBA (Digital Brand Architects) who helps a lot with social media strategy. We discuss content ideas and she encourages me to stay consistent with posting. DBA has been great to work with because they have amazing relationships with brands, which is so valuable. 

YouTube: I don’t use YouTube often, but I want to start posting there more. When I started my channel, I thought I had to be like every other YouTuber who vlogs their day and talks directly to the camera.

I would film videos and not post them because they didn’t feel natural to me. I didn’t like how I came across in those videos. The content that I enjoy sharing on YouTube is less talking and more showing. I love creative, montage-style videos. 

Shopify: In the past, my brother sold concert tickets through Shopify and the web developer who designed that site told me that it was a great platform for e-commerce. So, we decided to use Shopify to sell the merchandise and apparel. It’s very user friendly and straightforward.

This was helpful because I did most of the website setup myself. I’ve tried to build websites before on other platforms and I had no idea what I was doing. It felt impossible. I definitely recommend Shopify for anyone opening an e-commerce store. 

For the podcast: When we started the podcast, Lauren and I recorded in a studio and the sound engineer would send me the audio files after the session. I had to figure out distribution myself, so I did a few Google searches to choose which hosting site to use. We decided to go with Buzzsprout because it was fairly simple and easily connected to Apple Podcasts and Spotify. 

After about 6 months of doing our show, Lauren and I joined a podcast network called Dear Media. Our producer there helps with recording, editing and distributing the episodes, which has been great.

They also connect us with guests and sponsors. It’s saved a ton of time and energy, and I’m happy I don’t have to edit anymore!

Wix: Lauren and I also have a blog, which is an offshoot of The Sister Diary brand. The goal was always to expand the podcast and grow it into more of a lifestyle brand, which encompasses all of the different parts of both of our personalities.

We created a Sister Diary blog (, newsletter and merchandise. We use Wix for the blog and newsletter. It’s designed to be basic and user-friendly, which is great for our purposes.

Our newsletter is released every other Sunday. In it, we recap that week’s podcast episode, share some things we’ve been loving recently, and include a listener submission. Our listeners have really enjoyed that part. Having a newsletter has been great as well because it has allowed us to build up our mailing list, which is valuable to have. 

Klayvio: Klayvio is an app that is integrated into the Shopify dashboard. It allows you to create customized emails for marketing to your customers. It was recommended to me by the PR company that I am working with, The Mayfair Group.

Mayfair been helping a lot with branding, PR and marketing. I’ve been working closely with their graphic designer, who assisted with designing the emails, as well as the Artless logo, brand deck, hang tags, and shipping boxes.


What have been the most influential books, podcasts, or other resources you’ve learned from along your journey? Why?

Ed Mylett: Whenever I need motivation or to change my mindset, I listen to Ed Mylett’s podcast. He brings on high performers to talk about success and living the best life possible. 

Joe Rogan: I only listen to certain Joe Rogan episodes because they are so long, but the ones I do are always super interesting. He’s a great interviewer and I find myself paying attention to how he asks questions and communicates with guests. 

The Goop Podcast: I love the Goop website, so naturally this is one of my favorite podcasts as well. They cover a wide range of health and lifestyle topics and have such unique guests. 

The Skinny Confidential: This was one of the first podcasts I ever listened to, and I continue to tune in every week. The hosts, Lauryn and Michael, have a hilarious dynamic and I appreciate their genuine and honest conversations. 

The MIMIBEE Podcast: This is another one of my go-to podcasts about health, wellness, mindset and personal development. Mimi motivates her listeners to become the best version of themselves, and I always feel inspired after listening. 

Books: I’ve really been trying to become a reader in the past few months. I used to love reading when I was a kid, but now I never seem to have time for it. Right now, I’m reading Joe Dispenza’s book called Breaking the Habit of Being Yourself. It’s about self-development and working on your mindset in order to live a different life.

The other book I’ve been reading is Eckhart Tolle’s The Power of Now. It’s all about mindfulness which is something that I’ve really been working on. 

Resources: I try to constantly learn from others, especially those who are established in their field. I’m always looking at other influencers and businesses to see how they operate and what tools they use.

I’ve been lucky enough to connect with people in LA who work in the same industries as I do, and even people who are just doing interesting things. I think listening is a very important skill and you can learn so much by being attentive to others.

Are there any courses that have helped you?

Even though I was terrible at it, I took an accounting course in university that turned out to be very valuable. I think knowing basic accounting is essential, especially when you are a business owner. For the final project in that course, we actually had to start our own business and prepare financial statements, projections and a marketing plan as if we were going to create one for real. I hated it at the time but I learned great skills in that course.  

I also just started one of Joe Dispenzas’s online courses. I thought it would help me immerse myself in his work and better understand the science elements of it. He talks a lot about neurochemistry and quantum physics. I bought it a few days ago and have really been enjoying it so far.

Where would you steer someone who wants to learn more about what you do?

If someone reading this wants to start an e-commerce store, I would tell them to start off by doing lots of online research.

There are so many free resources available to you online. TOOLSY is a great example! There is someone out there who has already done what you want to do, and you can learn from them. Once you have your product, making a website and selling/fulfilling it is easy. It’s probably easier than you think it is.  

If you’re interested in podcasting, I would say go for it. There are no barriers to entry in podcasting. You can record into your phone or computer microphone if you don’t have a professional mic available to you. It’s probably not going to be perfect at the beginning, and that’s fine. 

In general, I would encourage people to take action. If there is something that you want to do, do it. I think people are hesitant to launch because they are worried about the things that could go wrong, or what other people will think about them.

In my opinion, it’s better to try different things until you figure out what you want to do instead of waiting until you’re totally clear on what your path is. I don’t think there will ever be a moment where I feel 100% confident in what I’m doing for the rest of my life.

What are you doing to continue learning and growing in the fields that you’re in as well as personally?

Continuing to grow, both in business and on a personal level, is very important to me. I never want to be at a standstill. I think that goal setting, and holding myself accountable to those goals, is critical. I try to regularly self-assess and refine my thoughts, habits and actions. I’m constantly looking forward to see how I can be better than I am right now. 

Another thing is learning from others. Whether it’s through podcasts, books, or real-life relationships, I try to expose myself to the perspectives of people who know more than me and are more successful than me. This has definitely helped with my growth.

Final Question:

What advice would you like to share with people based on your experiences?

First, you need to have unwavering confidence in yourself, or no one else will. Instead of talking about the things you want to accomplish, take action. It’s better to act and make mistakes along the way than not do anything at all.

Personally, I never want to look back at my life and regret not trying something or not living up to my full potential. You only get one shot at life. I also think that success is a constant, endless work in progress. If you delay your happiness until you feel successful, you will never be able to fully appreciate what you have.

Live in a state of blissful dissatisfaction with life; be both mindful and present and also future focused, consistently searching for growth and progress. Finally, you only actually fail when you just give up or stop trying. I’m still trying to remember that.

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