Wendy Oliveras
I believe that how you treat people shapes what you receive in return. Respect, integrity, and accountability are not abstract ideals to me, they are operational principles. Believing in yourself and setting clear goals have been foundational to my own success, and they are the same disciplines I encourage in others.
What began as a personal passion for playing chess has evolved into one of my most effective empowerment tools. Chess teaches patience, foresight, calculated risk, and resilience. Through teaching life skills and entrepreneurship as a second chance to inmates and returning citizens, I gained a deeper understanding of hope, perseverance, and the transformative power of strategic thinking. Those experiences strengthened my conviction that with structure, guidance, and belief, people can redesign their future.
I also have a deep love for writing and for helping others succeed in life, whether through business development, personal growth, or mindset transformation. Outside of my professional work, I enjoy family time, kayaking, dancing, playing chess, and embracing life fully. For me, success is not only measured in outcomes, but in impact, joy, and the lives uplifted along the way.
• MS Degree, The New School, Human Resources Management
• Jersey City Shero Award (March 17
• Philip Roth Endowment Grant Recipient
• Harvard Business Review Advisory Council
• U.S. Hispanic Business Council
• U.S. Small Business Chamber of Commerce
• U.S. Chess Federation
• Teaching life skills and entrepreneurship to inmates at New Jersey corrections facility (10 years)
• Business Beyond Bars community initiative
• Dress for Success New Jersey - job searching and job training programs
What do you attribute your success to?
At the core of my work is the belief that strategy must be paired with service. My success has come from combining disciplined thinking with genuine care for people, helping individuals build wealth while simultaneously rebuilding and strengthening their lives. Entrepreneurship, when approached strategically, becomes more than income generation; it becomes a pathway to dignity, ownership, and long-term stability.
I lead with integrity, remain consistent in my commitments, and approach every interaction with respect and intention. I care deeply about the people I serve. It is not only about helping them believe in themselves; there is profound fulfillment in witnessing someone step into their potential and succeed.
Teaching and empowering others is not simply something I do—it is innate. I know I am effective in this space because I bring clarity, structure, and conviction to every room I enter. Helping others grow, execute, and win is both my strength and my purpose.
What’s the best career advice you’ve ever received?
The best career advice I ever received was clear and uncompromising: “This is the last day of your pity party. Dry those tears, stand up, and keep it moving.”
That message reinforced resilience and personal accountability. Setbacks are inevitable; remaining stuck is a choice. The discipline is in recognizing the obstacle, adjusting your approach, and advancing anyway.
Just like in chess. You cannot undo a move once it is made. If you lose a piece, you recalibrate. If your strategy fails, you reposition. The game continues. Success belongs to the player who stays composed, thinks ahead, and makes the next move with intention.
What advice would you give to young women entering your industry?
First, master your craft. Competence builds confidence. The more technically prepared and knowledgeable you are, the less room there is for self-doubt. Invest in continuous learning, understand the fundamentals of your field, and refine your skills consistently.
Second, think long-term. Approach your career strategically and with intention. Every decision, partnerships, projects, branding, professional development, should align with a broader vision. Short-term wins are valuable, but sustainable success is built through deliberate positioning and disciplined execution.
Finally, create your own opportunities. Do not wait for permission, validation, or an invitation into a room. If access is limited, build your own platform. Design the table. Lead the initiative. Innovation and leadership often begin with the courage to step forward without being asked.
What are the biggest challenges or opportunities in your field right now?
In my field, one of the biggest challenges is helping people navigate systems that were not designed with them in mind. Whether it’s access to funding, business education, or second-chance opportunities, many aspiring entrepreneurs, especially those who are justice-impacted, face barriers that can feel overwhelming.
Another challenge is changing perceptions. There is still stigma attached to incarceration, and that can limit opportunities before someone even gets a chance to prove themselves.
But within those challenges are powerful opportunities. More communities are open to entrepreneurship as a pathway to economic independence. There is growing interest in second chances, workforce development, and alternative career paths. Technology also makes it easier than ever to start and market a business with limited resources.
Overall, this is a moment of possibility. With the right guidance, structure, and support, people can build something of their own, and that is where the real opportunity lies.
What values are most important to you in your work and personal life?
Integrity is foundational for me. I believe in doing what I say I will do and showing up consistently, whether in business, in teaching, or in personal relationships.
Respect is equally important. How we treat people matters. I approach every interaction with fairness, empathy, and accountability, because trust is built through everyday actions.
Service and impact also guide my decisions. I want my work to make a measurable difference in someone’s life, not just professionally, but personally. Helping others grow, believe in themselves, and move forward with confidence is deeply important to me.
Finally, discipline and strategic thinking shape both my career and personal life. Clear goals, thoughtful decisions, and steady execution create sustainable success. Those values allow me to lead with purpose while staying grounded and balanced.
