We were lucky to catch up with Kuu Sanford recently and have shared our conversation below.

Alright, Kuu thanks for taking the time to share your stories and insights with us today. Coming up with the idea is so exciting, but then comes the hard part – executing. Too often the media ignores the execution part and goes from idea to success, skipping over the nitty, gritty details of executing in the early days. We think that’s a disservice both to the entrepreneurs who built something amazing as well as the public who isn’t getting a realistic picture of what it takes to succeed. So, we’d really appreciate if you could open up about your execution story – how did you go from idea to execution?

So, I have a background in Executive Assisting and over the years I have gained so many skills: from PR, TV/Film, influencer marketing, and the tech industry. All this time I never realized that I was building up this variety of knowledge on how to build a successful, impactful, and intentional business. I worked closely with amazing and inspiring CEOs & COOs (Monica, Jasmyne, and Kolanie, to name a few) and all that time I’d been working in the corporate world – it wasn’t until I started training to become a professional dancer about three years ago, that I realized how much I loved being in the creative space. I found a passion for graphic design, creative direction, fashion and web-design. Eventually, I started working with a small company where I wore multiple hats. I got to do graphic design, social media marketing, and brand strategy. As I began to help build this company, I knew I needed to be apart of something that let me dream big. Around that time, I came up with this idea of Sidewalk Chalk, from just being out one day and remembering how much I missed sitting on a sidewalk as a kid, drawing – with no limitations or boundaries to my dreams or imagination. In that moment sparked a feeling of joy and peace that I hadn’t felt in a long time. And so, I started thinking of that concept and realized like, Wow, this, this could be really fun AND impactful.

That day, I went home and created my logo, my brand identity, color scheme, and campaign ideas. I built out potential website designs, wrote out the values that aligned with myself and how I’d want to bring a company into the world, and it was such a seamless process – because it felt so genuine to who I am and what I wanted to build. And so, the first two, three months I was mainly creating mockups on my computer. Eventually, I realized I needed something physical in order to understand truly what I was doing and what I was capable of. Soon after I was referred to an amazing printing company called MilkyWay Brands. Once we started printing my ideas, I really saw my ideas come to life and I could not only see them, but I could wear them for other people could see and feel it. It created this whole other world for me, of understanding the difference between ideation and creation. And for me, I think that is such a huge turning point to reflect on, because at some point you have to execute your ideas, not just for the world to be able to see and feel whatever you’re creating, but for yourself to know what you’re capable of, and that you CAN bring your ideas to life. So yes, once we started printing the first samples and those came out really cool and people were excited, I began to wear those samples to events. People would ask questions, people would share how it reminded them of their childhood. And those type of connections and stories has continued to motivate me to believe in, and pursue this amazing process.

In addition, I’d say the key to executing an idea is SURROUND YOURSELF WITH PEOPLE WHO ARE ROOTING FOR YOU. Yes, there is this concept of needing people to tell you when something is wack. But you don’t need that 24/7 in your beginning stages. Because no matter what you will evolve. So finding people who support you, share your passion, and/or genuinely verbalize wanting to see you win – go be all up in their space! And receive the positive energy because whether you put out the perfect thing or not, you will get brownie points for simply executing and taking action. and then more people will want to help and the more you will want to keep moving in this inspired and exciting direction.

Kuu, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

SideWalk Chalk is a streetwear/lifestyle brand whose mission it is to spark joy and connection through nostalgic streetwear – one inner-child at a time.

My name is Ku’uleilani Sanford, aka Ku’u, and yes I’m a proud Hawaiian who grew up with two amazing parents that taught me how to find joy in the little things in life. The abundance of laughter and gratitude I experienced at a young age was a huge reason why I am a big kid at heart to this very day. I enjoy connecting with people and experiencing life on a big and small scale – whether it’s traveling the world with friends or an early morning, sitting on the porch in Hawaii with my dad while he plays his ukulele. Every moment matters, and shapes us to appreciate the experiences we have in life.

As a hooper, volleyball player, snowboarder, and dancer, I was always bundled up in sweatsuits. So when I started SideWalk Chalk, I had the executive assisting experience and building a brand from the ground up – but what I wanted most was to make people feel comfortable in their own skin (or clothes in this case). And all I knew how to do at the time was express myself genuinely and go after my passion – which wasn’t fashion, it was getting to know and understand people! Once I realized fashion was the perfect vessel for creating something tangible for people to see and feel, it was inevitable I’d do oversized t-shirts, and sweatsuits. What I didn’t realize, was that it would spark beautiful, connecting conversations with strangers who are now new friends… and the memories it pulls out of people is by far the most joyous part of the process, and why I wake up everyday ready to share our mission.

I really brought nostalgic designs. (like our hopscotch sweatpant) into this concept to remind people that as kids we’re limitlessly creative and we believe we can do anything or be anything. Our confidence in following our passion is unmatched (I remember how confident I was that I was going to be a dolphin trainer and it brightened my world to know one day I’d speak with dolphins like in all the Disney Channel movies I watched hah). But regardless of what we thought we would be, there was a space of genuine belief that we could accomplish anything we put our mind to and were passionate about. And SideWalk Chalk’s goal is to remind people that that part of us is still alive within. We are capable of doing and being everything we want to be – we just have to believe, and talk about it. We have to connect with others in this genuine space of joy for ourselves. Joy, I believe, comes from being your truest self and being proud to be that. The other part is having a community that makes you feel welcomed as yourself as well. So something that makes me the most proud of what I’m building right now is that we’ve already been able to create so many connections with our community. The concept of our first collection called The Art- of-Joy, featuring our hopscotch sweatpant, has sparked numerous conversations of childhood moments people haven’t thought about in over 20 years, and has proven to remind people of that genuine feeling that there was a time when they felt unstoppable – and all they have to do is tap in.

And last but not least, I want to give a huge shoutout to my Dad, BenJAMIN Sanford, who, from the first time I showed him the mock up’s I made on my computer, has been my biggest supporter. He recently retired and now drives Uber in Hawaii (because he loves driving and talking to new people), and has since talked about my brand with all his riders and now has SideWalk Chalk business cards to give people on his rides. There’ve even been people who’ve messaged me on Instagram sharing that they met my dad and they do video production, modeling, etc., and would love to help support the brand. Shout out to the love and joy he spreads from Hawaii to here. :)

Okay – so how did you figure out the manufacturing part? Did you have prior experience?

So this is the perfect question because originally we started with blanks so that was the first process to understanding how to bring something to life in a quick and more affordable fashion. However, my dream is to create a sweatsuit that feels super comfortable, fits well and makes you feel good- so it was inevitable that I needed to go into cut and sew.

And cut and sew is a much more difficult process in many ways. I knew that it’d be kind of hard to get into that industry from what I’m told. You either have to have a ton of money and Capital to purchase these large minimums or you have to know somebody that’s already in the industry that’s willing to share their contact, which is a whole other story for many people.

And so the idea of getting into cut and sew was a little daunting, however, my story started by reaching out to an embroidery company that was an hour and a half away from me. The unfortunate part was that it was really far and I didn’t know if it was worth the time to have to drop things off and pick up with the small inventory I had. However, I connected with Marcel and he was, and has been, the most helpful person so far in my process. First, he told me about all the places that I could do wholesale blanks from, which was a huge, huge deal because that is what was able to get me started on seeing the possibilities of other things I could do outside of street wear, like hats, duffle bags (yes, these will be dope!), etc. He’s the one that sent me the companies to go to for patches and who I should reach out to for all these different aspects of things I didn’t even know of at the time.

It wasn’t until a month or two later that I reached out asking if he knew anyone in cut & sew. He didn’t, but he connected me with another amazing human, who might. She works at a dye shop, and I got to meet with her and she was just so joyful and loved what she did. And for me, those moments are so impactful. Being able to connect with others who are just as passionate about what they’re doing is really important for feeling inspired and motivated in your own space. Eventually she asked me what I was looking to do and I said, “Cut and sew”, and she said, “I have the perfect guy for you. They do really low minimums because he likes helping up and coming designers and entrepreneurs, and he’s been in the industry for so many years. Reach out to him, he’ll help you.” At first I said “there’s no way. This person doesn’t even know me? Why would he? Why would he help me? But I reached out anyway.

Met with a pattern maker, and the process had begun. It was such an eye opening moment because you get told, especially in fashion, that people don’t like helping and people are gatekeepers and people are this and that. And while that is definitely true, there are also so many people who are willing and wanting to help you. I realized that the more you express yourself in what you’re doing and the joy that you’re doing and the the mission that you’re doing it for, the more you will attract people who resonate with you, and maybe those people can’t help you, but they will give you a contact who can, because they believe in what you’re doing.

That was a really huge moment for me that someone who I’d only ever talked to on the phone was already so invested in seeing me win. And moments like that really make you want to help others and it makes you want to invest in other people. And so I guess the lesson that I continue to learn through this process is just be genuine, be yourself, and the more you own that, the less affected you will be by people who aren’t willing to help. And the more you will attract people who want to help. Then the more you attract those people, the more you will want to keep moving and growing and learning.

I also think talking about what it is that you’re doing, asking questions and most importantly, ask people what you can do for them? “How can I help?” What things are they working on and maybe giving them one of your contacts because it’s so important to give – and the more you give, the more you will receive.

And I truly believe that. And so, yeah, finding a manufacturing place is definitely daunting. But it’s possible. And the last thing I’ll add, is: go to events! Go out, talk to people, call places, ask questions, because the more you connect with people, the more information you will have access to simply by talking about what you love.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

Contact Info:

• Website: sidewalkchalk.co
• Instagram: sidewalkchalk.co
• Facebook: https://www.facebook.com/sidewalkchalk.co
• Linkedin: https://www.linkedin.com/company/sidewalkchalk/
• Twitter: sidewalkchalk.co

Image Credits
KuuBaby Productions, Jon Rabon, Maegan Alys Centella