Samantha Handler of KicksBySammy: 5 Things You Need To Know To Create A Very Successful Lifestyle Brand

An Interview With Vicky Colas

Chef Vicky Colas
Authority Magazine
10 min readMay 21, 2021

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Collaborate — Work with other like-minded brands through limited-edition collections, giveaways, live conversations, and more — they will all expand your brand’s audience and attract more traffic to your brand.

As a part of our series called “5 Things You Need To Know To Create A Very Successful Lifestyle Brand”, I had the pleasure of interviewing Samantha Handler, founder & CEO, KicksBySammy.

KicksBySammy is an eye-catching, custom, and made-to-order e-commerce accessories company featuring emerging artist and founder Samantha Handler’s hand-drawn, colorful, and whimsical designs.

Realizing Samantha was in search of new and exciting canvases, she became a self-made CEO at just 18, launching and bootstrapping KicksBySammy as a manifestation of her love of drawing and fashion. Samantha started the company hand-painting sneakers with her bright, standout designs, and has since expanded into a variety of customizable products across home, art, and fashion. They’re ideal for all ages and genders.

With collections centered on Baby, College, Camp, Bridal, Painted Kicks, Art, and more, KicksBySammy offers products that are perfect for both everyday life and life’s milestones. With the ability to request your own designs and feature your own name, phrase or initials, KicksBySammy products are truly one-of-a-kind. Samantha also creates artwork for events, invitations, promotional products, and murals, having partnered with companies such as NBCU, CBRE, and Hamilton Jewelers.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your “childhood backstory”?

As KicksBySammy begins to grow bigger, I often look back at life before it and reflect on my childhood experiences that shaped me into the business woman I am today. I grew up in a small town in Westchester, NY. I am the eldest of three, so from a young age I always felt the need to be a good role model and leader. What many people do not know about my childhood is that my friends never knew me as an artist, but rather as an athlete. I think being an athlete was a huge factor in shaping my leadership abilities, confidence, and outgoing spirit. Soccer was my life from 6th to 12th grade. I traveled all over the USA for games and tournaments, held captain positions, and made life-long friends with diverse backgrounds, life experiences, and views.

As my transition to college began, I started to embrace my other passion: Art.

Art was a secret passion of mine since most knew me as an “athlete.” Drawing was something as a young girl I always did for myself as a stress reliever and never wanted to be judged on. I began to draw on sneakers and paint more that summer before college, which ultimately led me on a path that would change my life forever. Who would have thought a pair of painted kicks would change my life?

Can you tell us the story of what led you to this particular career path?

KicksBySammy originally began with just a pair of shoes and sharpies.

The summer going into my Freshman year of college (2013), I was bored at home and found an old pair of white Keds in my closet. Eager for college and desperate for some cool tailgate outfits, I had the idea to draw on the sneakers with Maryland logos and fun doodles. I loved how they turned out (at the time) and decided to post my creation on Instagram. I began to receive numerous comments and requests from friends and family who wanted a pair of hand-painted shoes for their college. I decided this was a great way to make some extra cash and began to take orders all summer.

Fast forward to my first semester at the University of Maryland, I wore the shoes out and people constantly approached me asking who made my shoes. More inquiries started to roll in from people I didn’t even know. One night, while hanging with my college friends they all said, “Sammy, you are onto something big with the shoes. You should make a business account for it and take more orders.” Hesitant at first, I decided to go for it. My first question to my friends was, “What do I even name this business?” My friend shouted out “KicksBySammy.” Not thinking twice that this would turn into my full-time business by 2017, I immediately went with it and KicksBySammy was born.

Over the years, KicksBySammy has evolved into way more than custom kicks, but the name always stuck and has deep sentimental meaning. It really shows my followers that a simple idea as a teen can evolve into something much bigger with time and hard work!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Entrepreneurs usually make at least one mistake. If you haven’t made mistakes, you are not taking enough risks. Each mistake has turned into a learning experience and shaped me into the girlboss I am today.

One of my “funniest” mistakes that was more naive than funny, is that I did not realize that pricing products is a journey. When I first started, I undercharged for my products. Each of my products involves customization, which is very time consuming. I barely understood the word margin, and when I did learn more about it I realized my margins were small, which meant I couldn’t sell to retailers.

I learned how to price items properly as I grew, by researching my competitors, testing the market, learning about wholesale, and understanding my product’s value. This is just one of many examples on how I learned that building a business is a journey of many ups and downs. To build a business you need to constantly be learning, evolving, putting yourself out there, and recognizing that success does not happen overnight.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

There are so many amazing business books and podcasts, but those who know me personally know I am a Shark Tank freak. I may or may not have seen every episode a dozen times. When I was younger, it was really the first platform that showed me as a young girl that I could start my own business. It was my introduction to terms like royalty, margins, licensing, etc. Every time I watch the show I truly feel empowered and motivated!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Don’t worry about failures, worry about the chances you miss when you don’t even try.” — Jack Canfield

I have realized that most people from a young age are taught that failure is bad or embarrassing. I have recognized as I got older that we all should embrace failure. Failure often means we tried something out of our comfort zone and took a risk to accomplish something. I encourage everyone to share with others when they fail. What did you learn from it? What can you change to succeed next time? What was the reason for the failure? Answering these questions will teach you so much about yourself.

When I first took on KicksBySammy full time, at 21 years old, I was terrified with the idea of failing. What if no one bought my products? What if no companies wanted to work with me? What if I couldn’t pay rent or make a stable income? All of these what if’s in my mind almost stopped me from following my dreams.

However, I realized if I didn’t try, then how could I know what I was capable of? I am so happy I did not let the fear of failure control me because I would have never been able to do what I love everyday, meet so many amazing fellow girl bosses, and work with so many incredible people and companies! The fear of failure is real, but just remember you never know what your fears will cause you to miss out on!

Ok, thank you for that. Let’s now jump to the primary focus of our interview. For the benefit of our readers, let’s define our terms. How do you define a Lifestyle Brand? How is a Lifestyle Brand different from a normal, typical brand?

A lifestyle brand is a brand that not only is selling a product, but a way of life. Its purpose is to guide and inspire the like-minded community they create, with the idea that their product will help contribute to the ideal version of yourself.

What are the benefits of creating a lifestyle brand?

When you create a lifestyle brand you create a way of life. These brands are able to connect to their followers and customers on a deeper level. Customers feel a sense of community and belonging with other like-minded individuals. When a customer purchases your product they feel inspired and motivated, with a sense of purpose. Therefore, a person is likely to continue to purchase from you and stay a loyal customer as the brand grows.

In your opinion, what is an example of a company that has done a fantastic job building a believable and beloved Lifestyle Brand? What specifically impresses you? What can one do to replicate that?

One company that I think has done a fantastic job building a believable and beloved lifestyle brand is Kim Kardashian’s brand, SKIMS. With numerous other loungewear and shapewear companies, they have been able to stand out not only because of the celebrity face behind the brand, but because of the community they have created. SKIMS represents confidence. No matter your skin color, body shape, or gender identity, in SKIMS you feel more secure, worthy, and beautiful. Being comfortable in your own skin is what this brand is all about. The inclusivity of this brand inspires me, and I think it is a major component in why the brand is so successful.

Can you share your ideas about how to create a lifestyle brand that people really love and are ‘crazy about’?

Create a lifestyle brand that has longevity and isn’t just a “trend.” You want people to continue to want to be part of your brand and keep the buzz going for a long time. Find ways to have your company evolve with your customer and their needs.

People also need a brand that is a mix of life that is realistic and idealistic. You want your customers to be able to connect with your brand, yet also imagine a better life that your community and product will help create.

What are the common mistakes you have seen people make when they start a lifestyle brand? What can be done to avoid those errors?

Be GENUINE. I think people are over the fake, superficial, and perfect lifestyles that some brands create. People love authentic brands. Not everything about your brand needs to be picture perfect, over-edited, or unrealistic. Think hard about the community you want to create and never forget your brand revolves around your amazing customers! Your customers and followers will define your brand.

Let’s imagine that someone reading this interview has an idea for a lifestyle brand that they would like to develop. What are the first few steps that you would recommend that they take?

I would say start with the basics. You need to build your brand from the ground up. It is easy to jump to all the fun parts of building a brand, such as photoshoots, logo design, brand ambassador programs and more, but begin with defining your brand’s target market, mission, and value. Highlight key ways for your brand to stand out from others out there. You want to be unique and not copy what another company is already doing!

Ok. Thank you for all that. Here is the main question of our discussion. What are your “5 Things You Need To Know To Create A Very Successful Lifestyle Brand” and why? (Please share a story or example for each.)

  1. Be yourself

Show your customers and followers that there is a real person behind your brand. Your audience wants to come along on your business journey. Let them behind-the-scenes of the manufacturing process, a typical day in the life, daily struggles, travel, employees/interns’ lives, and more. People will instantly connect more knowing when they purchase your products they are also supporting you and your dreams. Do not be afraid to be authentic and show everyone the real you!

2. Build a community

If you want your brand to have longevity, you need to build strong relationships with your customers and followers. Show your customers what your brand represents, believes in, and values. By creating a bigger picture, your customers will connect more with your brand and continue to be loyal.

3. Provide transparency

Be honest with your customers. The more your brand tells a story at every level of the business the more involved people will feel with your brand. Put everything out there!

4. Add value

Provide your audience with trust in order to increase customer retention. You want your brand to continuously stay relevant in your customer’s life. Make sure to stay on top of their needs, go the extra mile for your customers, and continue to improve their experiences.

5. Collaborate

Work with other like-minded brands through limited-edition collections, giveaways, live conversations, and more — they will all expand your brand’s audience and attract more traffic to your brand.

Super. We are nearly done. Here are our final questions. You are an inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Age is just a number. I want to encourage girls and boys of all ages that you can start working on your dreams whenever you want! No time is too early, and you never know the life lessons you will learn on the way. My mission is to encourage the youth to shoot for the stars and to show anyone that with hard work and passion anything is possible. I hope to serve as a mentor and role model to the next generation. I am always open to mentorship calls; I want people to feel comfortable reaching out to me via social media or email!

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Hey, Mark Cuban! He is driven, tech-savvy, and knows how to sell. I would love to pick his brain shooting some hoops, over a cup of coffee, on Zoom, or on the phone.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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