Samantha C. Olexa, Esq., Managing Attorney on Influential Women
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Influential Woman · Law

Samantha C. Olexa, Esq.

Managing Attorney, Ivy Legal, LLC

Waukesha, WI 53222

3Years experience
4Awards received

Certifications · Degrees · Memberships

Degree UC Berkeley Law Executive Education Degree Western Governors University- M.B.A. Degree Marquette University Law School- J.D. Degree University of Wisconsin-Platteville- B.S. Cert Licensed to Practice Law in Wisconsin Cert UC Berkeley School of Law General Counsel University Program Cert Privacy Law and Data Protection Cert Certified Occupancy Specialist Member Wisconsin State Bar Association Member Wisconsin State Bar Association CLE Committee (3 years) Member American Bar Association Member Vice Chair of Real Estate Trust and Estate Law Committee for Young Lawyers Division (ABA) Member Wisconsin Commercial Real Estate Women Association (WCREW) Member Scribes (Legal Writing Association)

Her Story

About Samantha

Samantha C. Olexa is a strategic legal advisor, attorney, and entrepreneur who serves as Managing Attorney and owner of Ivy Legal, LLC, where she focuses on real estate, business, and corporate law. In addition to guiding clients through complex legal matters, she oversees the day-to-day operations of her firm, combining legal expertise with business leadership. Known for her practical approach and dedication to client service, Samantha helps individuals and organizations navigate legal challenges while building strong foundations for long-term success.

Her professional journey is a testament to resilience, determination, and lifelong learning. After leaving high school and earning her GED, Samantha worked her way through positions in food service, retail, and property management before pursuing higher education. She earned a bachelor’s degree in criminal justice, a Juris Doctor from Marquette University Law School, and later an MBA from Western Governors University. She further expanded her leadership credentials through the prestigious General Counsel University program at UC Berkeley Law Executive Education, which she completed on a full scholarship. Prior to launching her firm, Samantha served as an Associate Attorney at an AM 200 Law Firm, and in-house as the Director of Legal Affairs with Wisconsin's largest multiple listing service.

Beyond her legal practice, Samantha is deeply committed to professional development, mentorship, and service. She serves on the Continuing Legal Education Committee of the Wisconsin State Bar Association as well as the Vice Chair of the Real Property, Trust and Estate Committee for the Young Lawyers Division of the American Bar Association.

Samantha’s story—from GED recipient to attorney, business owner, and respected legal leader—continues to inspire others to pursue ambitious goals regardless of where they begin.

Her Interview

Ten minutes with Samantha

01What do you attribute your success to?

I attribute my success to perseverance, continuous learning, and the willingness to keep moving forward despite setbacks. Throughout my career, I’ve tried many different things; some worked, and some did not. The key was never allowing failure to be the final outcome. Each challenge became an opportunity to learn, grow, and try again.

I have also learned the importance of setting boundaries and knowing when to say no. As a woman, that can be especially difficult, as many women are conditioned to be people pleasers. In the legal profession, balancing professional success with personal well being often requires making difficult decisions, and not everyone will respond positively. I have found that trusting my instincts, maintaining strong ethics, and doing the right thing the right way—even when it’s uncomfortable—has been critical to my success.

Moreover, education has been the foundation of everything I have accomplished. Investing in myself, putting in the effort, and committing to lifelong learning transformed not only my career but also who I am as a person. I truly believe I would not be where I am today without that dedication to growth and self improvement.

Today, as a mentor, I try to pass those lessons on to younger women: believe in yourself, keep learning, and don’t give up. There will be setbacks along the way, but resilience, hard work, and education can open doors you never imagined possible.

02What’s the best career advice you’ve ever received?

Prioritize quality over quantity. No matter what you are working on, it’s important to take the time to do it right. That means giving your best effort, paying attention to details, and double (and even triple) checking your work before moving forward. In today’s fast paced environment, there can be pressure to respond quickly or produce a high volume of work. However, rushing often leads to mistakes that ultimately create more work and frustration for everyone involved. For example, sending an email without fully understanding the situation or producing multiple documents filled with errors is far less effective than delivering less work product that is accurate, thoughtful, and well executed.

Throughout my career, I have found that consistency, attention to detail, and a commitment to excellence build credibility and trust. Quality work speaks for itself and has a far greater long term impact than simply focusing on output. That advice has stayed with me and continues to guide how I approach my work every day.

03What advice would you give to young women entering your industry?

Develop confidence in yourself and have the courage to stand by your values. Law is a demanding field, and there will be times when your opinions, decisions, or boundaries are challenged. It’s important to have a thick skin, trust your instincts, and not let others intimidate or discourage you from pursuing your goals.

Also - always stay true to who you are, and don't change for anyone (even if they are paying you handsomely). Let your morals, ethics, and personal values guide your decisions, even when it may be easier to take a different path. Integrity is one of the most valuable assets you can have, and maintaining it will earn you respect and help you build a career you can be proud of.

Most importantly, do not let anyone convince you that you need to change who you are to succeed. Be authentic, work hard, trust your judgment, and remain confident in your abilities. When you lead with integrity and stay committed to your principles, you create a strong foundation for both professional success and personal fulfillment.

04What are the biggest challenges or opportunities in your field right now?

One of the biggest challenges in the legal profession is that it is inherently adversarial. While many people associate that vibe specifically with litigation, the reality is that even transactional practice can be highly contentious. Much of the work involves advocating for clients who are facing difficult and often stressful situations, which can create a constant level of conflict and pressure.

In my real estate practice, for example, I often work with clients who are dealing with serious issues such as eviction and/or the possibility of losing their homes. Knowing that the outcome of a matter can have a significant impact on someone’s life adds an emotional weight to the work. As attorneys, we are tasked with advocating vigorously for our clients while navigating challenging interactions and negotiations along the way.

Because of this, mental health and stress management remain significant challenges within the legal industry. It can be difficult to maintain a positive outlook when you are regularly exposed to conflict, uncertainty, and the struggles that clients face. In my experience, that challenge can be even more pronounced for women in the profession.

The key is finding ways to support your clients effectively while also protecting your own well being. Maintaining perspective, setting healthy boundaries, and staying connected to the positive impact of your work are essential. Although the profession comes with its challenges, helping people navigate difficult circumstances and achieve meaningful outcomes is also one of its greatest rewards.

05What values are most important to you in your work and personal life?

Honesty and transparency. I believe that many misunderstandings and conflicts arise simply because people are not communicating openly or directly with one another. No one is a mind reader. If something is important to me—whether it’s a major issue or a small concern—I can’t expect others to know that unless I communicate it clearly. The same principle applies in professional relationships, where clear and honest communication helps build trust, strengthen collaboration, and prevent unnecessary confusion.

I have found that being straightforward, forthcoming, and transparent creates stronger relationships and leads to better outcomes in every area of life. Whether working with clients, colleagues, friends, or family, honesty fosters trust, accountability, and mutual respect. Those are values I strive to bring to every interaction and decision I make.

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