For almost any creative, the dream is to be your own boss and turn your side-hustle into your career. It's shiny, there's freedom, more money if it's successful and so many other possible upsides. When Bimma Williams, sneaker professional turned expert conversationalist and host, left his stable career in the footwear industry to pursue his passion project Claima Stories full-time, these were the things he was after; and over time, he's been getting them, but not without some surprises along the way. Now with nearly fifteen years under his belt as an entrepreneur, five of which on Claima working with and interviewing some of the biggest names in the culture, Bimma has some stories of his own to tell and secrets to share with our community. Read the conversation below! Having left your 9-5 for a life as an entrepreneur and freelancer, what's something others thinking about doing the same should know? When most people consider freelance or starting a business, they often fail to realize what they are agreeing to take on. My creative expression is being a host, speaking, holding conversations, and now teaching as well. When I took that on, I'm not just taking that on. I'm also taking on, "how do I market and put myself out there?" Then you're in on finances. "How do I price myself?" Then you're taking on Operations because you need to figure out how to pay expenses and work on taxes and all of that stuff too. You're very involved in a lot of different things. You need to have the ability to harmonize all these different things. One thing to remember though is, yes, it is challenging but it's not impossible and there's also the opportunity for greater reward. You seem to be very humble with money and smart around spending on creativity. Are you thinking about that a lot? With any creative, when you get access to funds, the first thing you probably want to do is the biggest, shiniest thing possible. If you had all the resources in the world, you would leverage them but the interesting thing about that is, it's a mistake. We've seen it time and time again. When folks get too many resources, it actually diminishes their creativity. Some of the most creative projects and some of the best albums, did not have these glorious, gigantic budgets. They were just pure passion. When we did get that funding and that investment, we made some investments and some enhancements to production, but at the same time, we tried not to spend too much of that revenue. We would reach out to a brand and see if they would send us some microphones or some cameras or anything to keep the cost down. That money goes fast and you want to be super cognizant of how you can leverage it to get things to the next place over and over again. You've spoken about this concept of 'being ready' for opportunity. How does one do that? First of all, no one likes to hear this but you're never ready. It doesn't matter what the opportunity is because likely the opportunities are going to come from a place that you couldn't predict. Secondly, the opportunities are likely going to stretch you and so you have to make a decision on if you feel like you can rise to that occasion. One of the things that Will Smith spoke about in his book, that I love, is when you also are determining if you're ready or not, it also comes down to not being overly analytical and not overthinking the opportunity. When it's someone that you trust and they're bringing you an opportunity, to me, that opportunity is the one you need to say yes to and so sometimes being ready is purely just a mindset thing. You have to be ready in your heart. You need to be ready when it comes to how you want to put yourself in that situation. When you think about being ready, those are the things you need to think about. Once the opportunities and the audience come, it can feel tough to keep up with output demand. Have you every struggled with that feeling? All of these major media companies like Hypebeast or Complex, they all have huge content teams. This is why they can execute so much all of the time but as an individual, execute where you can execute. We've seen time and time again, so many different young creatives that may not have those systems, but they cut through with their thing. One of my favorites is Lynae Vanee. She puts out one video a week, and that thing cooks. She does her thing and she's not trying to compete with volume. She's competing with quality. I think when you have quality and you know your audience and you're hitting that sweet spot, people are always going to respond. They're always going to show up. When I came back, folks had missed me. It was clear. The response was there. So if I go away, it's not like I'm being forgotten in this sea of content or storytelling that's going out. So I think it's just important to remember that. Lastly, what do you think is the most important thing for any creative to understand, regardless of the industry? It's really important to develop a 'no bullshit mindset'. We can come up with a number of reasons why we won't do anything but I made an agreement with myself a long time ago was that there's nothing that's going to replace doing the work. That being said, I'm not going to feel 100% every day and it's okay if I decide, like, today I ain't got it. I'm going to take that break. If I can't put out something meaningful, what's the point? The world's not going to end and my audience isn't going to disappear because I needed to make sure I took care of myself. You can't do anything right if you haven't taken care of yourself first. Make sure to follow Bimma's Instagram for news on all of his upcoming projects and keep it locked to Pier Five for more conversations just like these!

The job market is a complex one to navigate but if one thing is certain, it's that results won't come without effort. For Rachel Wong & Istiana Bestari, when the market wasn't giving them what they needed to find their next big opportunity, they took matters into their own hands and developed the tools they needed to succeed. Quickly identified as a solution for a major gap in the market, Rachel & Istiana launched Monday Girl, a networking, events and digital platform to help women navigate the workforce and it's been a major success ever since. Now taking their 6-year side hustle full time, we got the chance to speak to the co-founders about their journey and expert tips, from networking to brand partnerships. Read below! Today, Monday Girl has become such an empowering place for women in the workforce. What was the motivation for starting the platform? Istiana: We built the platform that we wished we had, to solve a problem that we were struggling with. When we first met, we were both fresh to Toronto. We didn't know anyone and were trying to get our foot in the door. Rachel: All these rooms that I would walk into, I just felt, wow, I'm very much like the "only", whether it's the only woman, person of colour, or both. I was not getting any shortage of advice but it was a lot of advice that wasn't applicable for myself as a young woman of colour entering the workplace for the very first time. Istiana: For me, I remember attending so many networking events and just very quickly realizing how most networking events were not designed with women in mind. Typically, they were so exhausting. They were awkward. Also, I struggled with connecting with people on LinkedIn and I remember ranting to Rachel when we first met and she felt the same way. Rachel: In that same chat, we came up with the name of Monday Girl. We came up with the next action plans, and then we split up responsibilities. We were at it. You two seem like great business partners. How have you nurtured and grown your own relationship with each other over the years? Istiana: We really are each other's biggest cheerleaders. I don't think either of us could do this by ourselves and every day we're constantly hyping each other up. I think that's really important with having a co-founder is being each other's support systems celebrating our wins together. Rachel: I remember so many times where, for example, Istiana crushes it on a call or nails a presentation and I'm always just so proud of her and it goes both ways when I do things well. We really just hear each other out and hype each other up and that's helped us be such strong business partners. At least on the outside looking in, you seem very busy. Now that you're both in this full time, how do you keep it exciting and fun and not just feeling like a job? Rachel: Every so often, we get this really amazing message from one of our members about something that Monday Girl helped them with, whether that's overcoming a really tricky job situation where they had to deal with micro-aggressions at work or hearing that they used our resources to get a job or a mentor to get a referral. All these things keeps us going. Istiana: Another thing that's really important for us in keeping this excitement and momentum is that what we decide to do is always stuff that we're excited about. We're always planning things that we would love to attend, that we want to go to ourselves, all projects that we're excited about. It definitely is very hard work but it makes it a lot easier when we're building something that we're excited about. Y ou’ve done a really good job working with some major global brands and organizations on events and content for your community. How do you approach getting partnerships like that? Rachel: The first thing I'd say is don't be afraid to get ghosted and constantly reach out. After a certain point, people will get back to you and you just have to be okay with being persistent. Cold emails still work. The second piece is show that you put some level of thought - and it doesn't have to be super comprehensive or a full proposal - into your outreach and articulate how it can help the partner achieve their KPIs. If there's a specific collection or campaign that they're putting out, and you think there's a really strong synergy, talk to that in that very first sentence. People don't have the attention span to read through a long email, so just make that your only point if you have a point. The the third piece of advice is just to keep maintaining and building and give back where you can. Even if it's not always a paid thing, support the brands when you can. I think brands really remember that and that's when they want to work long term with. That's great advice! Lastly, what's a key networking tip you have for anyone that is looking for a new job? Istiana: A lot of people think, when they're starting out, "how can I connect with the CEO of my dream company?" and you're always looking for the most senior person in the room. Later, you'll realize that the most valuable people to network with are your peers. Start with the network that you already have. Tap into the people that you already know because there's a lot of connections there, whether it's your alumni, like clubs, sports teams. Rachel: Those are the people that as you grow, they grow with you and they're going to be able and have much more bandwidth than a CEO to actually help you and connect you with those openings or those roles when they do come up. I'd also say, don't be afraid to do this in an industry agnostic way too. Sometimes we think, "I'm in fashion and I'm only going to network to people in fashion". The reality is they're probably not going to tell you something opens up because they're going to want to go for it. However, if you're networking with people in different industries, there's a little bit more of a gap, so finding open spaces like that can be helpful. Make sure to check out Monday Girl for news about their events and mentor opportunities and keep it locked to Pier Five for more conversations with small business founders.

Almost every creative entrepreneur starts their business out of passion but as time goes on and the business grows, the legal matters of the business become more important but also often fall to the wayside. Zak Kurtz, lawyer and founder of Sneaker & Streetwear Legal Services dba Sneaker Legal, has turned his passion for kicks and coveted streetwear into a business designed to help creative entrepreneurs with all of those legal matters so that they can focus on their passions, while he focuses on his. We got the chance to chat with Zak about how he found an opportunity in a niche legal space, his tips for new creative entrepreneurs and what some of the keys have been to his success. Read the conversation below! Hey Zak! Thanks for chatting with us. Can you tell us a bit about you and your firm? Hey guys! So, my name is Zak Kurtz and I'm the founder of Sneaker & Streetwear Legal Services, also known as Sneaker Legal . Sneaker Legal works with clients in the sneakers, fashion, sports and entertainment space to help them protect their brand across a number of legal matters. You've built a very cool career in an admittedly niche space. What was the key to getting there? If you like something, go do it. I read a good book last week, and a line that I remember from it is, "let your joy be your GPS", meaning, whatever brings you passion, whatever brings you joy, do that in your life. Let that guide you. My grandfather was a judge, so I knew I wanted to be a lawyer but I wasn't sure about what in. I played soccer soccer in college overseas, so I thought I wanted to be a sports lawyer but in law school, while I was doing sports law, and I was president of all these things, and I was making a lot of money, I wasn't happy. I would sit on my computer and I would just look at trademarks like drawings of sneakers. Never did I know that one day I'd have a special law firm that's niche was in sneakers and streetwear. If you never giving up and follow your passions, that will definitely lead you to a good career and also a good life. We love that story and the self awareness about what makes you happy. At the end of the day, just be you. Staying true to yourself and what you love is the most important thing. If you're passionate about something, maybe it's sneakers and law or maybe it's something else, that will find a way to shine. If you want to build a brand and you're a good human being, people will come to you. We only live so long and I think it's important to be yourself and that really attracts people and brings good things into your life. You seem to have a great capability at getting clients. Any secrets there? A lot of the time, people don't reach out to legal because they're afraid of legal's answer always being "no". Due to this, most of the time when people come to lawyers, it's reactive. It's after you're getting a cease and desist or after you're getting a lawsuit. So, it's very important just to be upfront and work with your client so that that stuff doesn't happen. If you're releasing a shoe, come to us and we could say, "hey, this looks like an Adidas or a Nike. You might want to change this" or "this name is already trademarked by another company so you might want to change your name". We always take a very open approach because we believe it's important to be proactive with legal and I think that openness has helped create a welcome environment for new clients. Once you get a new client, what's often the first legal item that they might need help with? Starting is the hardest thing for your brand but once you start, you need to start thinking about all the stuff like establishing an LLC, registering trademarks, bringing on a lawyer or having someone around that you can ask those types of questions to. I can't tell you how many questions I get daily about little things like "should I have a contract for this?" or "do I need an NDA for that?". These are simple questions that a lawyer could answer for free or in a few minutes and I think it's good to start building that network and have that team environment. If I was to focus on one thing though, It would be the trademark. Anyone could actually do their own application or do some research but if you take it the next step and actually hire a lawyer, working on the trademark will really help protect your brand. That way you're boxing out the other people from using that name or that logo. Lastly, outside of the legal field, what's one piece of advice you'd give to a new entrepreneur or small business owner? You need to have a great team and be able to rely on other people because you can't do everything yourself. Then, once you find the right people, you need to trust them and let them do their job. I'm very cautious about every micromanaging them. I want my team to know that, as long they get the work done, they can be creative and flexible with their approach and I feel like that's been a key to the success of my team. Make sure to follow Sneaker Legal for all of your sneakers and streetwear legal info and keep it locked to Pier Five for more conversations with creative entrepreneurs and small business owners. Legal Disclaimer: The information provided on this website does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this site are for general informational purposes only. Information on this website may not constitute the most up-to-date legal or other information. Readers of this website should contact their attorney to obtain advice with respect to any particular legal matter. No reader, user, or browser of this site should act or refrain from acting on the basis of information on this site without first seeking legal advice from counsel in the relevant jurisdiction. Only your individual attorney can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this website or any of the links or resources contained within the site do not create an attorney-client relationship between the reader, user, or browser and website authors, contributors, contributing law firms, or committee members and their respective employers. 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Earlier this month, Pier Five proudly hosted its first ‘Community Court Day’ event in Toronto in partnership with PUMA. The event was designed to give entrepreneurs and creatives a new way to connect outside of the office in a space that was conducive to conversation and relationship building. As big proponents of 'breaking up the work week', Pier Five brought out 25 of Toronto's cultural change-makers, including business owners, artists, content creators and brand leads to spend a day on the court, a place that fostered so many relationships for us growing up. The day got started with guests arriving to a care package with some of PUMA's newest basketball gear; of course we had to hook them up in the best. From the beginning, strangers instantly started becoming friends and learning about each other. There's something about trying on new sneakers with others that get spirits high. After some introductions, basketball coach/trainer and founder of Core Basketball, Ali Nizam, started the day with warmups and partner drills designed to get people out of their comfort zone. Regardless of experience, every single person was sweating by the end of it. Spirits were definitely high, and safe to say we were all on an equal playing field after that. The warm ups were followed up refreshments from our friends at Neutria and Barbet who kept us hydrated throughout the day and a good 'ol fashioned 'name game' - of course we had to bring some summer camp memories back - to help everyone learn a bit more about who was in the room. After that, guests were put into teams to put their skills to the test. Every single person was playing hard and throwing it down! Lastly, we wrapped the day with a roundtable-style discussion focused on getting out of your comfort zone , something that is key for entrepreneurs and that every guest of the day demonstrated so well that day. The #1 goal of the day was give creatives and entrepreneurs a unique space to get to know each other and we couldn't be more proud of how much that was accomplished. In an age of social media connections and a non-stop grind to the top, finding time to meet likeminded individuals in-person, even those in our own backyard, can be very difficult but when you find a way to do it, break down all of the walls, and just let people jam, the results are incredible. A major thank you to every single person who came out with an open mind and willingness to learn. We can't wait to see how these conversations turn into incredible things outside of the gym doors. As well, thank you to Neutria and Barbet for the incredible drinks and of course, thank you so much to PUMA for supporting our vision of creating unique spaces for inspiring people to connect and grow. We can't wait until the next one!

The realities of starting any business always have two things in common. The first is you can't predict your path. There will always be unknowns. The second is that no matter where that path might take you, anything is possible. Sarah Sukumaran, NYC-based tech exec turned sneaker designer and now founder of Lilith NYC has embraced that wholeheartedly and has some great antidotes for anyone looking to turn their creative passions into a business. The learnings that she has acquired over the years with traditional tech roles, a predictive analytics gig at Nike - a natural fit for a sneaker-loving software product director - to now the life of an entrepreneur, have set her up for years of success and are something we could all benefit from. Scroll down for some gems from the conversation with Sarah. Hi Sarah! You're a big advocate of embracing your community. How did that play a part in getting Lilith off the ground? It's amazing. When you put out in the universe that you're doing something, people will naturally gravitate towards you and start making those connections wherever they can. Lean into that. When I started vocalizing and putting it out there that I was starting a footwear company, people all of a sudden had these connections for me and that's how all of my contacts, angel investors and other people I now work with, have come about. What's it like going from the tech world to now being recognized as a sneaker designer and brand owner? I worked in tech and I thought that was my life. I was ready to become a DevOps engineer and I really thought that's where my career was headed. So now, it's so nice to explore this creative side that I didn't know I had. I really love colour theory and working with materials. When I'm in Portugal, going to the leather supplier and looking at the suede that we're going to go with, or looking at the colour swatches; I have such a strong passion for that. People now refer to me as a creative and I'm still getting used to embracing it because I still am this nerdy tech person but now I'm a creative too which is pretty cool. Any advice to someone who was in your position looking to start their own brand while working a 9-5? I am a big proponent of not quitting your job and working on your side hustle when you're getting a nice check at your current employer. The only reason I quit [Nike] was because it was a clear conflict of interest working for a footwear brand and starting my own. If I was working as a tech company I would definitely have done this as a side hustle and just kept collecting a check. You need to be able to financially support yourself or have savings to be able to take that leap on your dream. Work full time and spend more hours after each day building your startup. There are so many little things you can do to get your startup off the ground, especially in footwear. You can source the factory on the internet and spend $200 to get a sample made. Everything is possible. You just need to take those small steps and making it work doesn't have to involve quitting your job and going bankrupt throughout the process. Lilith has done a bunch of pop-ups and is in a few retailers. Is expanding that a big goal of yours? I think for any brand, you always need to have a multi-channel experience. In year one, we started getting approached by retailers but I just felt like I wasn't ready. However, I realize now how important that is and we're definitely working on getting into more and more doors and doing more pop ups. Online is great but getting people to try on the shoes, especially at my price point it key. Just like any portfolio, you need a diversified approach as an entrepreneur. So true! Lastly, has been one of your biggest learnings since starting Lilith? Shifting away from traditional seeding and actually using your customers as the influencer, that's been an interesting shift and learning for me. I was wasting time seeding people who would post once and never wear the shoe again. Now, I'll surprise a customer who's bought two or three pairs and be like, here's a free shoe because I know that they're going to wear the hell out of it and that's probably better marketing at the end of the day. They're the ones who post the authentic photos, wear the shoes and get complimented in person and get way more excited! They're their own ambassadors to the brand. I love it and they love it. Make sure to follow Lilith for news on their pop-ups and releases and keep it locked to Pier Five for more conversations with creative entrepreneurs like Sarah!

If there's something that Carlo Aragon, designer and founder of social gorpcore community, Salomonology, knows, it's the importance of a strong foundation. From URL to IRL, Carlo has taken his childhood loves, from video games to sneakers to outdoors exploration, to build a base for some incredible projects that not only help people dress well, but also care for our planet at the same time. Find out how he does it in our conversation with Carlo below! Hey Carlo! The growth of Salomonolgy has been so incredible over the last few years? What's the goal with the page? To this day, we still get people who are like, "yeah, you wear Salomons, but how many hikes have you done recently?". It's like that"oh, you're wearing the band tee, but do you really listen to that band?" I really try to push the fact that a piece of clothing is meant to be worn, whether it's for its original initial technical purpose or just for casual wear. So the page is really exists to show people that there's nothing wrong with taking something that's meant for something else and just wearing it for a completely different reason. For me, an article of clothing has always been an article of clothing to be enjoyed. Why is it about gorpcore that makes it something you really care about? I want more people to be more conscious about the environment. I think with the way that the the world is projected to look in the next 10, 20 or 30 years, it's not looking great but when people go out and enjoy the outdoors, I think they start to recognize more about how lucky we are to actually have it. If people need to be into a trend for them to finally start hiking to appreciate being outdoors more, then that's awesome. I think gorpcore has really helped people get outdoors more and if Salmonology can be the doorway or that first step in getting people to use that style to be able to get outdoors more and appreciate what we have, it will make people more aware of how we need to be more protective of our world and nature in general. From a strategic standpoint, how do you approach projects longterm to keep your audiences locked in? I think people are always looking for how genuine you are in the work that you produce and how true to yourself you are with what you produce. At the end of the day, if the project stays connected to that one anchor that you started from in the beginning, what you build over time will still be meaningful. Know what your foundation is, stick with that and build off of that so that people can look back at everything that you've produced in the past and to see that you've stayed true to yourself. I think that's what people really recognize and appreciate. Makes so much sense! Lastly, as someone with a fashion brand and a knack for influencing people's style, what tips would you give to someone working on their personal style? When you're trying to find your personal style, I think it's important to focus on silhouettes and fit. That's the best way, because when that becomes your priority, you could go to the thrift store, you could go shopping at the mall, you could go anywhere, and then you could start shopping not for brands, not for labels, but for fit. When you leave the door every day looking like you're wearing the same outfit, but it's actually different clothes, that's when you've kind of achieve the personal style. In addition to that, I feel like it's also important to look back on stuff that make you happy, and then you incorporate that into stuff that interests you. Make sure to check out Salomonology and Carlo's new brand Equipe Works and keep it locked to Pier Five for more conversations with creative entrepreneurs!

Very few things in life last forever but while many try fiercely to hold on, Sandro Petrillo, Canadian DJ, artist and entrepreneur, has learned to find beauty in the impermanence end enjoy the ride. After a period of burnout and time to reevaluate his work habits, Sandro developed and launched his new venture, SSSOAPS, a premium soap brand that encompassed everything that he loved; shape, colour, smell, tactile experience, and every-changing energy (something he grew fond of with music development). We got the chance to chat with Sandro about his journey with SSSOAPS and pocketed a few gems that he had to share throughout the chat. Check them out below! Sandro on Embracing Impermanence In many of the artworks or the creative practices that I lean into, I love the idea of impermanence. I love the idea that what we encounter in our daily life and beyond is truly impermanent. Everything at a certain time will be here, and then it will not and I think getting to know those things and getting to be comfortable with those things and that sort of measure of time and connection to things is really a beautiful connection to the way that we live. Soap, and the time period in which soap disappears and changes form, is very indicative of that transfer of energy in impermanence. Sandro on Trying New Things I'm a very big believer in that life happens for us, not to us. When we have opportunities in life that are challenging, those are opportunities for us to learn and to grow with. Don't be afraid to learn. Don't be afraid to spend a little bit of money and time to try things out. Sandro on Learning To Let Go In this day and age, you will encounter so many opportunities, so many potential lanes to go down, so many new ideas that take you down a different path. I think while that is the case, further sharpening your non-attachment will be a huge tool in making sure that you can maintain your work and stay focused. Understand that, while it's great to have ideas and new experience things, it's important to consider all of that in your calculation of what is your capacity and what you can get done. Then, on top of that, learn to let go of things and understand that you don't have to do everything. Sandro on Scaling With Intention When the opportunity to scale comes, really lean into your intention behind what you're trying to build. It's something you need to be careful of because you can turn it [the business] into a bit of a monster. Like, you can turn it into this thing that you once loved and now fear and resent. Scaling is the inevitability of a business's trajectory but I think it's something to be really mindful of and really careful with. Think about why are you going there, why do you want to move in that direction and what is it going to take to move in that direction. Make sure to follow SSSOAPS on Instagram to get info on Sandro's latest drops and keep it locked to Pier Five for more conversations with creative entrepreneurs.

They say that pressure produces diamonds and this definitely shows through with Rae Mendoza and I'll Call You Tomorrow, his clothing brand and artist collective based out of Edmonton, AB that has been working hard to put their city on the map amongst the heavy hitters of Toronto, Vancouver and Montreal. We got the opportunity to chat with Rae about the growth of his collective, how it opened up new doors with his agency Tomorrow Works and tips he has for creatives looking to get noticed. Read some excerpts from the conversation below! Rae on Building Things His Way Being housed and running everything from our home city of Edmonton, Alberta is really freeing for us. It lets us build our community how we want to do it and not as a reflection of something else. We just love this challenge of building new infrastructure and new opportunities for people that resonate with our platform where they don't typically exist. It also just lets us be a bigger fish in a small pond. Rae on Working With Friends I was very fortunate from the start to just always be around just super talented people, whether it was photography, design, music, now tattooing and illustration. Once I started working with them though, I really quickly realized where now as a business owner working with my best friends, it's up to me to set those boundaries of like, "in this space we're professionals working together and I'm holding you accountable for deliverables, and we have a specific function we need to do, and then we can go back to being friends outside of that space." In terms of finding the right people, a lot of it comes down to that gut feeling of knowing that we see things eye to eye, whether it's like good product, good design, taste levels, community, or you just knowing that this person's honestly just a good person. Rae on Finding New Opportunities Tomorrow Works as an agency has this living portfolio that is always constantly putting out new work in the form of I'll Call You Tomorrow. The bulk of our business just comes from people seeing our brand and then knowing that they can do something similar for their brand and their business. It's such a small circle these days of who is interconnected, putting your work out there and just showing that what you can do and how you deliver it at a very high level is the most important thing. Most of those things will kind of just sort themselves out and come to you. Then as a consultant and on the agency side, it comes down to you being ready for those looks as they come. Rae on Passing The Torch We started noticing it happening now as me and my team, we're getting a little bit older, where young kids will come up to our events and our parties and they'll be like, "I'm 22 or 21 and the first pop up or cool art party that I ever went to was one of your events and now I'm starting my own t-shirt line or I want to do certain things in the streetwear and arts community because of that event" and seeing that grow outside of us is some true 'pass the torch' legacy type shit. That's the stuff that keeps me up at night that I love. Make sure to follow I'll Call You Tomorrow and Tomorrow Works on IG for news on all of their upcoming events, projects and clothing releases and keep it locked to Pier Five for more conversations with entrepreneurs coming soon.

Once you get going, it can be hard to slow down but we can't forget the tales of our childhood. You can't rush success. Slow and steady wins the race. Such is true for Josh Heares, founder of New Zealand based clothing brand Porter James Sports, who has spent the last two-and-a-half years carefully crafting his label. With a clear path ahead and a mind that has never been more focused, Josh is on his way to becoming one of the most stand-out menswear street brands in our opinion and we got the chance to chat with him about his journey from advertising to fashion, how he plays the fashion game with an analytical mindset and where he hopes to take the brand in the future.

Read the full interview below! Hi Josh, thanks for taking the time to chat with us. For those who aren't familiar, can you tell us a little about yourself and how your brand, Porter James Sports, came to be? Thanks guys! I started Porter James out of my living room in Auckland, NZ about 2.5 years ago, in December 2020. Before that, I spent my career in the advertising and design space so I was new to fashion taking on this project. Today, I would say PJS is the convergence of menswear and streetwear and the values we champion are 'simplicity' and 'timeless design'. We try to be accessible but from day one, I was really keen on ensuring that we didn't look like a 'part-time' fashion brand. I have a high bar for the brands I wear as a consumer and PJS had to match that. With no prior experience in fashion, what was the motivation to pivot from your career in advertising? In my mid-twenties, I got a promotion at my advertising agency and was really excited. At the time, I thought this was my dream job, blending business and creativity together but one day realized that I didn't see a long-term path for this and felt like something was missing for me and wanted to create a change.
A mentor told me about this idea of envisioning my dream day instead of my dream job and that changed everything for me. I started thinking about the things I value most like making my own schedule, being able to be creative and work with other passionate people instead of large corporations, and then being able to work from wherever I wanted. Fashion checked a lot of those boxes so I started spending a lot of time looking into how to make that possible. So from there, how did you get started? I threw myself in the deep end. I got an agent out in Guangzhou, China and flew out there to meet him to speak about product development. Luckily he was from New Zealand and spoke perfect English which was a huge help. From there, I just asked a lot of questions. I brushed up on all of the product development information, figured out how much money I would need to start everything. On the other hand, having worked in advertising for so long with brands like Mercedes-Benz, I knew what world-class delivery looked like and had a benchmark for what I wanted to try and hit with my own brand. The reality of leaving your job and starting a brand is that money can get tough. How did you manage there? Absolutely! I knew that I was going to need income from other sources so I started a consulting side-hustle, which allowed me to sustain enough revenue once I left the agency job. I still do it now and it's a great extra job, allowing me to use my past experiences and help others develop their brand plans. I know the brand is strong and will continue growing but it obviously takes time so I didn't want to put all of my eggs in one basket from the beginning. You seem like you're very patient, which doesn't always come so easily to entrepreneurs. I think it's important to look at things like a sliding scale, not a light switch. Success won't come overnight. I heard this great quote that "people overestimate what they can do in a year but underestimate what they can do in ten years". Where you are now, consider it a stepping stone that's planting seeds to where you want to go. I know that if I'm intentional and become comfortable putting in the work, it might take two or three years to start seeing some real return but in ten years I'll be very happy about the work that I put in. Do you have a long term or ten year plan for the brand? I just want to continue to grow the brand bigger, while staying in my lane. I've never been clearer than I am now on what our products look like and what our 'brand filter' is, meaning how I think we should look and what we should be putting out. We're focusing on DTC growth now which I'm really starting to figure out and I think that I'm on the right path which is the most important thing to me. The DTC landscape is ever-changing. What are the most important thing to be thinking about these days when running an online business? This isn't new but the only way to really grow a huge business is by acquiring more customers, so that's where all of my focus is. You need to understand why someone might not buy from you and mitigate all of those barriers. For me, as a brand from New Zealand, it's improving shipping so that new customers can take a chance on the brand. I've worked to ensure I can offer fast-free shipping because I know my quality is good, and that if I can get my products into the hands of the "fashion-guy" of a friend group, they'll influence their ten friends and that's how everything will grow. So I just need to ensure the person landing on my page has no reason not to checkout. Besides the quality being top notch, what's your strategy for the product design and collection building? As you connect with new producers and learn new things around the product, I think it's easy to get overwhelmed. The truth is, you can build a multimillion dollar brand around just five or six styles ( a great shirt, a great pair of trousers, a great hat, etc). I've watched so many brands scale massively by perfecting certain styles and that's what I'm trying to do. That helps me ensure the quality, fit, and look are perfect. Taking inspiration from other trends and brands is ok but apply what works for you and make sure to stay in your lane. I'm also trying to remind myself to slow down and constantly iterate as opposed to pumping out a lot of product quickly. I'm constantly thinking about how I can make the product better, from the stitching to the materials, to the decoration. I'd say taking it slow is what is going to help us win. Love that! Slow and steady wins the race. Make sure to check out Porter James Sports for their newest drop on Monday, July 17th and keep it locked to Pier Five for more conversations with creative entrepreneurs!

A common through line in entrepreneurship is resilience but the idea of always "pushing through" is often easier said than done. What helps is having something to push through for and Jess Sanchez, founder of Colombian-Canadian jewelry brand Santa Isla has a thing or two to say about purposeful commitment after building her business across the world for over a decade. Created with the Embera Chami (meaning people of the mountain in their traditional language) artisans of Colombia, Jess has fostered a community around her Colombian culture that shines light on this centuries old art form that she knows she can never stop supporting. We got the chance to speak with Jess about her ups and downs as an entrepreneur, how she has adapted the business over the years between multiple countries, the reality for anyone looking to start a business, and where she hopes to take the brand next. Read the full interview below! Hey Jess, thanks for taking the time to chat with us! For those who aren’t familiar, can you tell us a little bit about yourself and your business Santa Isla? Absolutely! So I'm Jess, the founder of Santa Isla which is a jewelry brand. Santa Isla is my love letter to Colombia. It's an exploration of where I come from, woven with my Canadian identity. I consider the pieces of Santa Isla little tokens of Colombia for everyone to wear and hold. All of the pieces are made with lovely Embera Chami artisans who weave spiritual intentions that you can hold and feel. Looking back at your Instagram, it seems the brand has been around for a while but evolved quite a bit throughout the years. How did it start and what was that evolution like? It started 12 years ago when I came across these Embera artisans in Colombia and really loved the bead work they had created. I bought two pieces and was wearing them around in all of the big cities in Colombia I was travelling to and so many people were asking me about the necklaces, what they were and where they came from. It was a bit dumbfounding to me, like "how can something that comes from here and is so rooted in our heritage be so unknown to so many of our people" and it pushed me to spend more time learning about this craft and the history behind it and made me want to make some of them myself. I spent a lot of time trying to find and connect with these Embera artisans to learn and once I did, that's where Santa Isla started; but it was a passion project, not meant as a business. To learn more about the Embera Chami, click here. For almost 8 years I was making really extravagant and large pieces but it wasn't until 2 years ago after a bit of a break during COVID that I started to pivot to merge these traditional techniques with more fashion-forward designs like rings, anklets and necklaces that are the driver of the brand now. Wow, so you've really put in the time to build this! Absolutely. As an entrepreneur, you have to put in the time. I understand that the time part isn't very sexy. We don't want things to take time. We want them to move but unfortunately - or maybe fortunately - it's really an exercise in patience. You really have to put in the time to get to know your business and your offering and then you can't stop. You spoke about this fairly significant pivot from more traditional to fashion-forward pieces. What was the reason for that shift? After so many years of creating these traditional pieces, which were mostly bought as display or art pieces, I decided I wanted the brand to be more accessible and in order to do that, I had to change the offering. Once I started getting into smaller, more fun and easy to wear pieces, it completely changed things for the brand. Was it scary making such a big change like that? I've had so many moments of doubt and asking myself, like "what am I doing" but I think that those moments of reflection are really important. As an entrepreneur, there are going to be so many moments where something isn't working but you can't stop; but you can pivot! The place you start might not always be the place you finish and that's ok. The important thing though is just don't stop. We love a brand with purpose and it seems that Santa Isla is exactly that. Can you speak more about that connection with the Embera Chami artisans and the part it plays in the brand? That is everything for me. That is my "why". For a brand, I think that your story is everything. Running a business is not easy but it's much easier to stick with it when there's something attached to it that's outside of you. Working with and supporting these artisans is the only reason that I've kept going after all of these years. It was hard and for a long time I wasn't making money but I kept on going because these people are amazing and they've been helping me learn more about my identity so how can I not continue to give back. As Santa Isla grows, where do you hope to see the brand go long term? If there was another brand I had to compare Santa Isla to, I'd want it to become like a Telfar where everybody has one, and it's cool that everybody has one. I want us to be worldwide with drops selling out and me being able to get Santa Isla into the hands of everyone, being accessible. I want it to be the marker of a community where everyone is proudly wearing Santa Isla and supporting this culture. Love that! Lastly, on your crazy journey with the brand, what is one piece of advice you'd give to an emerging entrepreneur? If you're ever feeling stuck or down, go help somebody! Even with a simple compliment, it can change people's attitudes and if you can find ways to then weave that into your business, it changes the game and can be a big motivator for you to keep going. If you want to become a part of the Santa Isla community, make sure to follow them on Instagram for news on all of the brands upcoming drops and keep it locked to Pier Five for more conversations with creative entrepreneurs coming soon!

There's something about empowering emerging talents that really speaks to us at Pier Five and anytime we come across others in their field who are passionate about the same thing, we are immediately drawn to them. This was the case for Saucony collaborations manager Jason Faustino who has worked for the last 17 years to create opportunities for emerging talents, whether that was in his sneaker boutique Extra Butter or on footwear collaborations at Saucony. We got the chance to chat with Jason - hot off of his collab with our good friends Raised By Wolves - to discuss his journey through the sneaker industry, his vision for collabs, business tips for sneakerheads and his outlook on the future of sneaker drops in 2023. Hey Jason, thanks for chatting with us! For those who aren’t familiar, can you tell us about yourself and your role at Saucony? For sure! l'm Jason Faustino and I lead brand collaborations across Saucony Originals and Performance. Ive been with the brand for a little over 4 years. I work on the marketing side and am very involved with product getting to do a little bit of everything. Your history in sneakers goes way back, notably co-founding Extra Butter in 2007. Can you speak about your journey in the sneaker industry from them to now? While I was in school I used to break dance a lot near this mom & pop sneaker store and started working there and was learning a ton about those brands and products. I was doing everything, from stock room management, buying and advising on marketing strategies and without even realizing it, was getting a crash course on sneakers. While I was at the shop, I learned about Magic which is this major trade show in Vegas and used my credentials from the shop to get in. I originally learned about Magic through this shop called Fruition. I told them I wanted to open my own shop one day and they really mentored me on how to build my vision and cultivate a successful brand. Fast forward to 2017 I ended up launching Extra Butter which was a movie themed sneaker store in Long Island and NYC. It turned into a pretty successful business. I found a ton of incredible brands and did lots of collabs, including some with Saucony, and then that relationship is ultimately what led to me going to work in-house at the brand. We've spoken to people at shops on the collab side but how does working on sneaker collabs in-house work? It's a lot of fun. when I started, my main responsibility was marketing and I just focused around what stories could and should be told. Once I started to get my feet wet, I spent a lot of time looking through seasonal catalogues and choosing what silhouettes I want to work with and then figuring out who I want to collab with on those silhouettes. We'll bring in the collaborators and I'll work a lot with the product team and we'll really build everything out together. I was told - and now firmly believe - that product and marketing better be in lockstep with one another to have any sort of success. It's cool though because I have freedom to create the stories that I connect with and think our audience will really love. What’s the process for building out those story for a campaign? The big thing is really thinking about what the brands stand for. A lot of people have this misconception that collaborations have to be this big crazy thing but the most important is just staying true to each brand ethos and going from there. For example, when I was at Extra Butter, we did a collab with Asics and so I really wanted to tap into the Japanese culture of Asics and blend it with the pop culture ethos of Extra Butter and tie in a favorite movie, Lost in Translation, which is how we landed on a karaoke themed collection. Once we landed on that, it was almost like method acting. I was doing a ton of karaoke, observing others do it and really immersing myself into that lifestyle and then the story built itself from there. You’re in the midst of a big collaboration with Raised By Wolves right now. How was the launch party this past weekend? It was amazing! I really wanted to give full creative freedom to Cal and the brand and they brought in some incredible talent to put the creative and party together. I'm really happy about how this all came out, from the shoes to the experience. We've noticed that a lot of recent Saucony collabs are with emerging designers or brands that are in the midst of some serious growth. Is that all intentional? For sure! I try to find those who haven't had their chance to tell their story yet. This is something I've always been about. Even back in the day with Extra Butter, we would often be a brand's first retail partner. I see it like sports and placing bets on people. We might not always know what the outcome will be on the new talent but that's why I like it so much. Somebody's gotta give that creator their first collab and I like to be that brand. I also want to be able to grow with our collaborators and go on a journey together. The emerging creatives have so much to say and Saucony can be that brand that helps people discover them and grow with them over multiple collections. What advice would you give to young sneakerheads looking to get into the industry like yourself? If you're truly about this culture, at some point realize the difference between being a consumer vs. being in the industry and follow those industry paths. Figure out what you really love about sneakers - maybe it's design, maybe it's storytelling, maybe it's sales - and pursue that. There's not a job for just loving sneakers but there are so many cool opportunities that exist that can get you very close to sneakers. Another thing... I often see people idolizing people and obsessing over 1 role model and trying to be like them but that can only get you so far. It's important to bring your own charisma and ideas to the table. With everything that's happening in sneakers and fashion, those new ideas are what will get you far, not just being the same as someone who's already made it. That's really good advice! Before we let you go, what's something in sneakers that you're excited about for 2023? It sounds strange but I feel like the sneaker game overall is a bit stale and that is exciting to me. A lot of people don't realize but some of the launches we're getting are still delayed from the pandemic and there's a lot of the same stuff which people are sick of BUT that means that we're at the point where there's room for newness and innovation and I'm excited to see what we can bring at Saucony and also what other brands bring! Now it’s time to get more exciting and innovate Make sure to check out Saucony on Instagram for updates on all of the newest collaborations and keep it locked to Pier Five for more conversations with incredible designers and creators!

The powers of curiosity are truly incredible! Carolyn Chen, founder of dog care brand Dandylion has learned this throughout her life as a serial entrepreneur with years in the beauty industry and now pet care industry. As she follows her passions and curiosities, she finds that doors continue to open, much of which by the people she meets along the way and the communities she builds with likeminded individuals. We got the chance to speak with Carolyn about her experience founding Dandylion and tapped into her tricks and advice for new entrepreneurs looking to turn their everyday passions into full-time businesses. Hi Carolyn, for those who aren’t familiar, can you tell us a little about yourself and Dandylion? My name is Carolyn Chen and I am the founder of Dandylion which is a community powered dog grooming brand on a mission to clean up and add transparency to the dog grooming industry. Dandylion launched just over a year ago and was inspired by my life as a parent to a dog with itchy and easily irritated skin, finding that there weren't a lot of products out there that were effective and transparent (like the products in human skincare/grooming) in terms of the ingredients in the solution. Where did the name come from? I wanted a name that captured the essence of a childlike carefree-ness to the world. One day I was listing to that song "Dandelions" by Ruth B and loved how the word captured that feeling. I also liked the play on words with “dandy” and “lion. It also helped with trademarking which, from my time founding other brands, I know is very important when it comes to picking a name. Speaking of other brands, we know you have some history founding beauty brands. How did that help inform the process for creating Dandylion? Yes, so I've had 4 years as a DTC beauty brand founder. It all starts with understanding the problem you are trying to solve for. For Dandylion, I was trying to solve the itchy skin issue for my dog, but I wanted to validate the idea to see if other dog parents experienced the same pain point. I started with 100 interviews with dog parents and then once I dialled in on the problem, I brought in a vet dermatologist and human skincare chemists to help develop a solution for dogs. It was important to have experts to bring the latest thinking from human formulation and understand how to best formulate for dogs. For example, the PH level of dog skin is different than human skin, which is something we learned from our vet dermatologist. Since its launch, Dandylion has seen hugely positive reception IRL and online. Can you speak to what you think was key to achieving this. A few things for sure. Asides from the product needing to perform well, we try to come up with innovative solutions and formats and involve our community ever step of the way. The community that we have built has been so integral in helping Dandylion grow so quickly. From support on social to friends and family helping me pack and ship boxes, everyone has really come together to help which I am so thankful for. Looking more at the product, from the packaging to the creative ads, everything seems very premium and almost high-end. Why was that important for you? I'm glad you see that! It took me a very long time to develop and I learned Adobe Illustrator on my own to design this [laughs] so thanks for noticing! My brand is really going to be for this next generation of dog parents so when I look at the brands they're consuming, I have to fit within that. I'm looking at brands like Glossier or Recess or Aesop which connect so well with millenials and Gen Z and that was how I drew inspiration for Dandylion. Dandylion comes in at a price of $22 per bottle whereas most brands come in around $8-$10. Has there been any difficulty entering the market as a more premium product? So far it's been well received but I think it all comes down to brand values which are: High quality ingredients Proven by experts and scientists Eco-conscious formula and packaging Better Value. Dandylion uses less product per application so you get more uses out of each bottle than the regular brands That's great to know and we definitely understand this. With the brand growing so quickly, what are you thinking about most as you scale? For us it's always about planning ahead and being prepared for things before we need them. So, thinking about things like supply and demand. If I have 10 orders per day now, what does it look like when I have 100 orders per day and what do the pieces around supply chain and operations look like then. the set up process to scale those operations so it's very important to look ahead. Another big thing for me is optimizing cash flow. So, finding ways to hold onto money longer, whether that is finding ways to pay suppliers later or finding ways to get money from customers sooner. If you can optimize for cash flow and plan ahead, you'll be in a great spot to grow. Those are 2 great pieces of advice! Before we let you go, what are some pieces of advice you'd give to any young entrepreneur that is looking to start their own business? The biggest thing is to follow your curiosity and see where that leads you. Try as many things as possible, fail fast and learn from it. I think this will give you a lot of new perspective that you can incorporate into any project that you're working on.

I also think goal setting is very important but keep those goals flexible. It's great to have something to work towards but you want to ensure that if something changes, you can account for that. Lastly, surround yourself with people who uplift you and can make the process of starting something a lot more enjoyable! Make sure to check out Dandylion on Instagram for news on new products and community events and keep it locked to Pier Five for more conversations with inspirational founders just like this!