Box Babe: Samantha Dong

Meet Box Babe Samantha Dong, Stanford student turned entrepreneur. After an injury that prevented her from wearing the heels she loved, she decided to start her company, Ally Shoes. Read about how Samantha is making heels a woman's best friend and her necessities for survival as an entrepreneur.

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You live in the NYC area, what keeps you there? What makes the city special?

I lived in NYC for two years for my first job after college, and recently moved back after spending 4 years in the SF bay area. When I decided to start Ally, it made sense to move back to NYC where a lot of our target customers and footwear design talent reside. In addition, despite my love for the outdoors and the California sun, NYC reminds me most of my hometown, Shanghai, with more dynamic industries and people of diverse backgrounds.

What is the story of how you started Ally Shoes?

Growing up, both of my parents worked in fashion retail, so it’s an area I was fascinated by at an young age. During my first job in consulting, I was staffed on multiple Omnichannel projects for brands and retailers across the US, which gave me a front row seat to how technology was changing the way people shop. But it wasn’t until a hiking incident that triggered me to look into comfortable high heels.

First year in business school, I went on a 7-day trek in Africa. I reached the summit and had an amazing time. But on the way down I injured both of my big toes and hurt multiple tendons. It took half a year until I could start wearing closed-toe shoes. Also, heels were no longer an option. But I wasn't ready to give up. One question kept popping up in my head: Why do heels HAVE to hurt?

That thought led to a year of extensive research with shoe experts around the world and hundreds of conversations with women suffering from heel pain (which is most women). That’s why I decided to move back to start Ally, and make heels women’s best friend, instead of a necessary evil.

How do you overcome day-to-day obstacles in your life and business?

There’re a couple things that helped me get through tough times:

  • Remind myself of the big picture: I vividly remember one of the top venture partners in Asia once said, the best quality he sees in entrepreneurs is not perseverance nor charisma, but the sense of clarity. Once you have clarity on why you’re pursuing what you’re doing, be it a burning passion or a strong calling, everything else is secondary. I couldn’t agree more. When things get tough, it’s easy to be stuck in the present, and the obstacles ahead of you will seem bigger than they are. But when I remind myself of what propelled me to start the business in the first place, it gives me the clarity to keep moving forward.

  • Find ways to relax: This is particularly tough for entrepreneurs, but very important to maintain a clear mind and outlook. For me, the key is to find time and activities outside of work that I enjoy, namely yoga, hiking, and reading.

  • Be scrappy and keep pushing: There’s no way to sugarcoat how hard entrepreneurship is, particularly because we’re doing something that’s not been done before, with limited time and budget. It’s supposed to be hard, otherwise something is wrong. In addition to vision & strategy, sometimes it’s really just about knocking on enough doors and hoping one of them would open. I’ve had numerous cases where I’ve completed a mission impossible, just because I didn’t give up.

  • Ask for help: Entrepreneurship is a truly humbling process, in the sense that I’m constantly reminded of my own limitations, and made me realize that I can’t do it alone. I learned to not try and control everything, but instead seek help from my team, advisers, mentors, our customers, and even strangers.

Say a reader wanted to start their own business, what advice would you give them?

Have a great support system. It’s going to take much longer and be much more difficult than you ever expect; it will likely take a toll on your mental and physical health. Make sure you have plan and people around you to help you through these times.  

Name a book everybody should read right now.

The Life-Changing Magic of Tidying Up” by Marie Kondo. I believe we live in the age of abundance - in terms of physical things and information. This book not only helped me declutter my living space, but also form a clearer and purer mentality in life.

Who is the coolest woman you can think of right now? What makes her so cool?

Lyn Slater (@iconaccidental). She’s 64, a professor, and a fashion icon. Lyn herself says it better:

“Women (like me) who are not famous or celebrities but are smart, creative, fashion forward, fit, thoughtful, engaged, related and most importantly clear and comfortable with who they are.”

 Lyn Slater

Lyn Slater

What's the last purchase you made that simplified your day-to-day life the most?

A printer - sound so silly, but we used to outsource all of our printing. The new printer saves us money and time on running back & forth Fedex to print.

What do you believe to be true that almost no one else agrees with you on?  

The significance of a diamond engagement ring is overrated. It’s merely a marketing ploy by de Beers during the 1930s when diamond demand was down. They also later controlled supply in order to maintain price and created the misconception that diamond is rare, when in fact it’s not as rare as some other gemstones. But this does show how powerful it is when a product is connected with our deepest emotion (in this case, love), and then get rooted into social norm.

How can we find out what you're doing these days? 

Follow us on Instagram! (@allyshoes)

If you had a Renzoe Box right now, what will we find in yours?  

Eyeliner, foundation, two high shadows (one silver tone, one bronze tone), two lipsticks (pink one for daily, red one for special events)


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Ally is a fashion-forward company for ambitious women who believe beauty doesn’t have to hurt. Every pair of Ally heels is built using a patent pending 4-step process for heels that look as good as they feel.

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