We recently connected with Paulaska Ramirez and have shared our conversation below.

Paulaska, thanks for taking the time to share your stories with us today Looking back, do you think you started your business at the right time? Do you wish you had started sooner or later

I founded Generation Fearless in 2019, at a time when I had already spent nearly a decade in higher education, supporting first-generation students. I was deeply immersed in student success work, but I realized there was a gap in mentorship and resources specifically tailored for first-generation women beyond the academic setting.

At that point in my career, I had built strong networks, developed leadership skills, and gained the experience necessary to create something impactful. If I had started earlier, I might not have had the strategic knowledge, professional relationships, or confidence to navigate the complexities of launching a nonprofit. On the other hand, if I had waited, I may have missed the opportunity to respond to the immediate needs of first-gen women who were seeking support in real time.

Starting when I did allow me to blend my lived experience as a first-gen woman, my professional expertise, and my passion for advocacy into a mission-driven organization. Looking back, I wouldn’t change the timing—I believe Generation Fearless was launched at the right moment, when I had the clarity, resources, and drive to make it sustainable.

If anything, the only thing I might have done differently is seek more funding and support earlier on to scale faster. But every step of the journey has been a learning experience, and I’m grateful for how Generation Fearless has evolved.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My Story & Journey:
I’m the founder of Generation Fearless, a nonprofit organization dedicated to empowering first-generation women through mentorship, career development, and financial wellness programs. My journey into this space wasn’t by accident—it stemmed from my own lived experiences as a first-generation woman. I am a first-generation everything; first-generation American, college student, professional, and founder. I’ve spent over a decade supporting first-gen students at William Paterson University, where I also oversee the Educational Opportunity Fund (EOF) program. Through this work, I realized that many first-gen women face unique challenges, not just in academics, but in navigating their professional journeys and financial well-being. That’s when I knew I had to create something specifically designed to fill this gap—Generation Fearless.

I started this nonprofit in 2019 with the mission to educate, empower, and support first-generation women at every stage of their journey, whether they’re students, professionals, or entrepreneurs. I wanted to provide them with the tools, resources, and networks they need to succeed without the boundaries imposed by their circumstances.

What We Offer & The Problems We Solve:
At Generation Fearless, we provide a range of services tailored to first-gen women:

Mentorship & Coaching: Offering one-on-one career coaching, personal growth retreats, and leadership development workshops.
Scholarships: Our Fearless Trailblazer Scholarship helps first-gen women access higher education and professional opportunities.
Financial Wellness & Professional Development: We host retreats and workshops focused on financial literacy, career advancement, and building sustainable success.
The core problem we solve is the lack of targeted support for first-generation women, especially in areas like career progression, financial literacy, and personal growth. We bridge the gap by offering tailored resources and a supportive community that champions their success.

What Sets Us Apart:
What makes Generation Fearless unique is our holistic approach. While many organizations focus solely on academics or career development, we take into account the complete well-being of our participants—academic success, career development, financial wellness, and emotional resilience. The community we’ve created is centered on empowering women to thrive in every aspect of their lives, and we do so with a focus on intergenerational healing and cultural awareness.

Another distinguishing factor is our mentorship and leadership programs, which are designed to provide ongoing support, not just a one-time experience. We believe that mentorship should be continuous, so we provide long-term guidance and a network that helps women not only survive but thrive in spaces where they may not have had a roadmap before.

What I’m Most Proud Of:
I’m incredibly proud of the impact we’ve had on the lives of first-generation women. From providing scholarships to creating spaces where women can learn, grow, and lead, it’s been incredibly rewarding to witness the transformation in those we serve. I’m particularly proud of how we’ve created a community where women can come together to share their experiences, build connections, and empower one another.

What I Want You to Know About Me and My Work:
I want potential clients, supporters, and followers to know that Generation Fearless is not just an organization; it’s a movement for first-generation women who are ready to break barriers, build generational wealth, and rise above challenges. I’m passionate about helping women realize their full potential, and I want them to know that we’re here to guide and support them every step of the way.

I believe in empowering women to take ownership of their journeys, no matter their starting point. Whether you’re a student figuring out your path or a professional aiming for the next level, we’re here to help you navigate those challenges with resilience and confidence.

Can you tell us about a time you’ve had to pivot?

When I founded Generation Fearless in 2019, the plan was to serve primarily as a local organization focused on providing in-person events and community-building opportunities for first-generation women. We had already started creating immersive retreats, workshops, and mentorship programs that would allow us to make a direct, personal impact on our participants. But, as we all know, COVID-19 disrupted everything.

At first, like many organizations, we found ourselves facing an unexpected pause. All our in-person events were canceled, and for a while, it felt like everything we had worked so hard to build was suddenly on hold. But that moment of uncertainty became the catalyst for a massive shift in how we thought about our mission and the way we could continue to reach women.

Instead of succumbing to the limitations of the pandemic, we asked ourselves: How can we continue our work in a way that serves even more women, beyond the local community? This question led to a realization that we didn’t just have to be a local organization—we could grow into a national and even global force for first-generation women.

So, we pivoted to online programs. We transitioned many of our workshops, retreats, and mentorship offerings to virtual formats. This was a huge learning curve for us, but it opened up new doors. By going online, we were able to expand our reach, connecting with first-gen women across the country—and eventually around the world.

Our online programs, like our May retreat, became an essential part of our offering. We also developed virtual coaching, workshops on financial wellness, and professional development that could be accessed from anywhere. This was a crucial moment for us to redefine our mission and scope, and we began building a more scalable, accessible model that would serve women on a much larger scale.

By the time restrictions eased, we had already transitioned to hosting hybrid events—a mix of online offerings and in-person retreats that allowed us to stay connected to our core community while reaching new clients in places we hadn’t initially considered. In 2023, we took our first national road tour, hosting in-person events and programs in several U.S. cities. Our success in these areas reinforced the idea that we were capable of growing beyond our original vision.

Looking back, I realize that the pivot during COVID was one of the best decisions we ever made. While it was initially driven by necessity, it transformed Generation Fearless into an organization that could serve first-gen women across the globe, rather than just in one community. We have learned to adapt quickly, stay true to our mission, and take advantage of new opportunities to expand and connect.

What’s worked well for you in terms of a source for new clients?

The best source of new clients for Generation Fearless has been word-of-mouth referrals and the power of community partnerships. When women experience the transformative programs and support we provide, they naturally share their stories with others, creating a ripple effect within their networks. This organic growth has been invaluable because it’s based on trust and authenticity—women recommend us because they’ve experienced the impact firsthand.

Additionally, our strategic partnerships with educational institutions, nonprofits, and professional networks have been key in reaching new clients. By collaborating with organizations that align with our mission, we’ve been able to tap into broader networks of first-generation women who are seeking the kind of support and resources we provide.

Finally, our events and retreats—such as the annual “Owning My Journey” one-day retreat—have been fantastic ways to engage with new clients directly. These immersive experiences create lasting connections, and participants often return or refer others, building a loyal community.

Contact Info:

• Website: https://www.generationfearless.org/
• Instagram: https://www.instagram.com/generation_fearless/
• Linkedin: https://www.linkedin.com/in/paulaskaramirez/