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Entrepreneurial Lessons From Sydney Sherman de Arenas: Kindness, Encouragement, and Building Sustainable Success

Sydney Sherman de Arenas headshot

Meet Sydney Sherman de Arenas, the Co-Founder and CEO of Montie & Joie, a sustainable brand revolutionizing supply through a mission of connection, empowerment, and joy. 

Sydney’s entrepreneurial journey is one deeply rooted in a family legacy of serial founders and driven by a personal connection with a skilled artisan in Guatemala. As a result, Montie & Joie was born out of a profound need to fill the gap in the production side of artisan craftsmanship. Sydney’s commitment to ethical employment and consumption is at the core of Montie & Joie, empowering a global community of artisans with meaningful and fairly paid work. Her path has embodied the philosophy of building a business one small block at a time, emphasizing the importance of simplicity and ethical values.  

We asked Sydney about the founding story behind Montie & Joie, how she navigates self-doubt as an entrepreneur, and what’s next for her and her company.

Tell us the story behind your company’s founding. How and why did you start working on Montie & Joie?

I come from a family of serial entrepreneurs. Before founding Montie & Joie, I already had some successful businesses running. Montie & Joie started somewhat in reverse from my other projects. Through repeated visits to Guatemala and connecting with a skilled artisan who didn’t have a way to make a living from her remarkable talents, I saw a significant need to fill a gap on the production side of a business, as opposed to the customer side. This was a risky, back-to-front position to start a business from. But my Mom and I felt passionate about ensuring that Monite & Joie was successful so we could provide an income and creative outlet for talented artisans in Guatemala and beyond. Today, our global community of artisans have excellent working environments, are paid fair wages, and are contributing to an environmentally conscious way for customers to enjoy fashion, homegoods, and interiors.

In what ways has your upbringing or past experiences contributed to how you operate as an entrepreneur?

My parents are both entrepreneurs and were extremely intentional about building a very close family unit. I had a childhood defined by open lines of communication between my parents and I, where we would often discuss business and money. Even as a young child I remember playing at writing checks and my parents taking me to discuss investing with a stockbroker. It was never a question of if I was going to be an entrepreneur but when and how. During an MBA program for entrepreneurship, one of my colleagues mentioned how they could tell I was already ahead, simply because of my upbringing. Being an entrepreneur is really hard. I’m grateful to have parents who supported me and my siblings to be conscientious and driven adults with the ability to start our own companies.

Image of woven basket

What are the biggest mistakes you’ve made?

While building an online marketplace that inspired me to start selling Montie & Joie’s creations named The Etho, I unfortunately became business partners with someone who turned out to be very untrustworthy. I was so overwhelmed with a desire for this online marketplace to be successful that I ignored a number of red flags. I’d raised over one- million dollars from friends and family to fund this business. When this business partner intentionally brought the business down, I felt I had failed not only my friends and family but also the hundreds of brands who were connected to The Etho. It was an exceptionally hard lesson to learn that quick fixes don’t exist. Since then, I’ve learned to build a company one block at a time, while carefully verifying anyone who I work with in order to create sustainable businesses with amazing teams full of trustworthy people.

What’s the biggest misconception that others have around entrepreneurship?

I have a memory of sitting down to dinner after I had just moved to NYC at a time when I was working extremely hard on building The Etho. I was extremely short on cash, was working all hours of the day and night, and barely had time to look after myself. I overheard a conversation where a young, beautifully made-up woman shared her dreams to be an entrepreneur just like Kim Kardashian to her dinner date. I felt like she just didn’t get what entrepreneurship was, and it really made me think. 

To me, entrepreneurship isn’t glamorous, especially not at the beginning. Because of our ability to perfect our image on social media platforms, I see a lot of brand stories that make it look easy and/or glamorous. The reality is, when I even have time to look in the mirror, I normally see imperfections that are a direct result of my dedication to my work. I sacrifice sleep, give out of my own income in order to pay the salaries of employees during political unrest or downturns, and stress over carrying the weight of being responsible not only for myself but for the livelihoods of many people. These are the sacrifices entrepreneurs make that don’t make it onto a social media highlight reel.

Have you struggled with self-doubt as an entrepreneur? How do you navigate this?

There have been so many ups and downs along my entrepreneurship journey, and my self-doubt has gone up and down with the success of each company. I've poured a lot of time, energy, and finances into therapists and other groups or programs that have helped me to discover more about myself and separate my self-worth from the success of my businesses. As entrepreneurs, it’s important that we work on ourselves because our companies are direct reflections of who we are. 

As I rebuild my self-worth, I find myself sharing what I’ve learned with employees and other ambitious people, helping them to quell an insatiable competitiveness and replace it with self-assuredness and teamwork. Each day I’m learning more about my inherent value and the value of those around me, solidifying that self-worth regardless of my entrepreneurial successes.

Sydney Sherman de Arenas with indigenous women

Has your definition of success evolved throughout your journey as a founder?

My definition of success has definitely changed over the years, and I attribute much of that to engaging with different people and places throughout the world. After completing a program in Austria, I became friends with people from all over the globe and was lucky enough to visit many of them. Upon visiting India, I was particularly struck by the extreme levels of poverty. I decided that after I’d completed my MBA I’d create a business that would do something significant to positively impact people in developing countries. Unfortunately, my initial definition of success was very numbers oriented. How much was I selling? How many people knew my name? After experiencing serious difficulties in business, my definition of success shifted away from numbers and toward happiness and freedom. My dad has always said, “Money doesn't buy you happiness; it buys you freedom,” and I think that's really true. Success for me now looks like freedom and happiness in my personal life, as well as freedom in the lives of the people I work with across the world.

What resources or people have contributed the most to your successes?

I think about this all the time, as access to opportunities is absolutely critical to success. With supportive family and friends, parents who are successful entrepreneurs guiding me, and an incredible business partner in my husband, I have so many wonderful resources and opportunities that propel me toward success. Even without considering my family, I had a fantastic public education, went to an incredible university, and have a U.S. passport, which enables me to travel the world. Living in Guatemala, I am often reminded of how valuable these resources are. In my local community, I meet people who are lucky if they get enough money to buy food for the day, let alone a formal education. I have a disproportionate amount of resources supporting me to do everything that I'm trying to do. When I look around me, I see people who do not have these same resources, which spurs me on to create opportunities for others in every way I can.

Have you discovered any underappreciated leadership traits or misconceptions around leadership?

Growing up in a supportive household has shown me that being a kind and encouraging leader goes a really long way. It’s all about thinking, “What can I give away?” instead of, “What can I gain?” In our small community in Guatemala, we are not here to compete with each other; instead, we are here to support and encourage one another. We are here to treat our employees like human beings and build loyal teams of people who feel respected. This mindset doesn’t only make sense from a moral perspective but also from a business one. It’s simply a fact that it’s more expensive to replace employees than to step in and support your existing team to flourish, even in difficult times.

What would you tell your younger self if you were to start your entrepreneurial journey all over again?

Focus on building your business one small block at a time. Where things have gone wrong for me in the past is having an enormous grand vision and biting off a lot more than I can chew. There are so many benefits to starting off with something simple, figuring out how to build a business on your own, and learning how to sell to just one person. Because if you can sell to one person, you have a chance at selling to more if you continue to build something that people truly desire.

What’s next for you and Montie & Joie?

I’m working hard to connect many of my companies together, including finding opportunities for Montie & Joie to contribute creatively toward the hospitality businesses I run with my husband. Monite & Joie is also involved in designing the interiors for an extremely exciting project in Steamboat Springs, Colorado called The Astrid. Overall, I’m simply placing one foot in front of the other, taking Montie & Joie back to our basic values of ethical employment and consumption, and growing one day at a time.

Image of Sydney and other Montie & Joie individuals

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