Sisterhood, Systems & Success: Navigating Business & Culture with Lesley Braga

Mar 7

Cozypreneur Episode 23

In this special episode of Cozypreneur, Stacy Braga sits down with her sister, Lesley Braga, to dive into entrepreneurship, building efficient systems, and navigating life as first-generation immigrants. Their conversation spans everything from business strategies to family dynamics, touching on the challenges of career transitions, the importance of cultural identity, and how privilege plays a role in success.

If you're an entrepreneur trying to streamline your systems, a fellow first-gen navigating identity, or just someone who loves a good sibling dynamic, this episode is for you!

From Corporate Operations to the Unknown

Lesley Braga, an expert in project management, operations, and regulatory compliance, has spent her career making complex systems run smoothly. But after being laid off at the end of 2024, she found herself at a crossroads. With a mortgage, two kids, and no immediate job prospects, she’s now figuring out her next steps.

This conversation sheds light on a common struggle—how do you transition when life throws you an unexpected curveball? Lesley shares her perspective on operational efficiency and how those same skills can be applied to entrepreneurship, something Stacy has been refining in her own business.

The Power of Systems in Business (and Life)

For entrepreneurs, especially those wearing multiple hats, having strong systems in place is key. Stacy shares how she once resisted using tools like ClickUp, finding them overwhelming at first. But now, with a streamlined approach, she uses it to track her recurring tasks, podcast episodes, and deadlines—freeing up mental space for creativity and growth.

Lesley, with her background in operations, immediately saw ways to further refine and optimize Stacy’s systems. Their discussion highlights an important takeaway: the right systems don’t just make businesses more efficient, they also reduce stress and decision fatigue.

First-Gen Struggles & the Cost of Success

A major theme of the conversation is the experience of being first-generation immigrants. Stacy and Lesley reflect on the unique challenges they faced growing up—balancing cultural identity, taking on adult responsibilities at a young age, and navigating a world that often overlooked their backgrounds.

Lesley recalls how her high school guidance counselor discouraged her from applying to college, assuming she wouldn’t be able to afford it. Meanwhile, she was expected to act like an adult in other settings, translating legal and medical documents for their parents. These conflicting experiences shaped their perspectives on privilege, opportunity, and the hidden barriers many first-gen individuals face when building a career or business.

The Privilege Conversation That’s Missing in Online Business

While many business owners promote the idea that “anyone can start a business,” Stacy and Lesley discuss why that narrative is misleading. Having financial security, a second household income, or even access to free housing can be the difference between success and struggle.

For Stacy, knowing she had housing stability, a financial cushion, and a partner’s income allowed her to take the leap into entrepreneurship. Not everyone has those advantages, and it’s important to acknowledge that success isn’t just about “hustling harder.”

Family, Identity & Keeping Culture Alive

Beyond business and career talk, the sisters reflect on the importance of keeping their Portuguese heritage alive. Lesley, who teaches her children Portuguese, shares why she prioritizes cultural connection despite societal pressure to assimilate.

They also touch on how being white-passing adds another layer of complexity to their identity—how they’re seen as white Americans in some spaces, yet still experience the struggles of being raised in an immigrant household.

Looking Ahead: Entrepreneurship or Corporate?

As Lesley explores her next career move, she wonders if starting her own business is a viable path. Stacy, having spent years building her own, acknowledges both the freedom and struggles that come with entrepreneurship. While there’s a lot of appeal in working for yourself, the reality is that it takes time, financial stability, and a solid support system to make it work.

For now, the sisters joke that maybe Lesley should just run operations for all the podcasters out there—because if this episode proves anything, it’s that she knows how to get things done!

What’s Next?

This episode is a mix of business strategy, cultural identity, and sibling banter, offering an honest look at what it takes to navigate life’s transitions. Whether you’re an entrepreneur, a first-gen professional, or just someone trying to get their life together, there’s something here for you.

If you enjoyed this conversation, stay tuned—because the idea of a family podcast might just be happening!

Let us know—should the sister podcast become a reality? And if you’re a fellow first-gen entrepreneur, what’s been your biggest challenge in balancing business and cultural identity? Drop a comment or DM Stacy on Instagram (@stacybragacopy)!