National Women’s Small Business Month: Women Aren’t Just Building Businesses. We’re Building Legacies.

Oct 5

7 min read

What 15 years of entrepreneurship taught me about being underestimated, betting on myself, leading as a woman, and building something that outlives me.

By Rebecca Contreras

There was a time in my life when becoming a CEO wasn't even something I knew how to dream about. I didn't come from a family of entrepreneurs or have the financial means to start a business. I didn't have the traditional education people associate with successful executives. My childhood was filled with dysfunction, poverty and circumstances that could have easily determined the trajectory of my life. I was a teenage mother with a GED, and I knew what it felt like to walk into rooms and wonder whether I belonged there. I had also worked as a W-2 employee my entire career, with no background in what I now call the entrepreneurial spirit.

And yet, my journey took me from those beginnings to state government, to serving in the White House, to becoming a woman entrepreneur and building a multimillion-dollar company. I don't share that because I think success makes my story special. I share it because your beginning does not get to write your ending.

During National Women's Small Business Month, we celebrate a record-breaking number of women starting companies, creating jobs and taking risks—to the tune of 14.5 million women-owned businesses, representing almost 4 out of every 10 businesses in the United States. We should. Many of us have built our businesses while juggling it all, raising families, caring for the people we love and navigating rooms and industries where we were the only woman—or one of very few.

But we also need to talk honestly about what happens before the success people see: the self-doubt, the risk, the failures, the exhaustion, the moments you're underestimated, and the decision—made over and over again—to keep going anyway. After 15 years of entrepreneurship, I've learned that building a business will test more than your business skills. It will test what you believe about yourself.

Being a Woman in the Room

Early in my career, people underestimated me because I didn't have the education, credentials or experience they expected. Being a Latina added another layer. I learned that women can walk into the same room, bring the same results and still feel pressure to prove we deserve the seat. Let me say this clearly: although we have made tremendous progress, we have not yet arrived.

Women in leadership are often given conflicting messages: be confident, but not too confident; be strong, but not difficult. I stopped trying to solve that impossible equation. I could spend my energy convincing everyone I was capable—or I could get to work.

So I got to work. What I didn't know, I learned. Where I lacked experience, I surrounded myself with people and mentors who knew more than I did. When someone opened a door, I walked through it prepared to work my tush off. And when people underestimated me? Performance and results became my response.

To the women building today: you do not have to shrink yourself or adjust your unique style to make other people comfortable. Walk into the room knowing you belong there. Confidence isn't arrogance. It is believing you have earned your seat—and then using that seat with purpose.

At Some Point, You Have to Bet on Yourself

Before becoming an entrepreneur, I had built a successful career in government and the private sector. From the outside, I was successful. But eventually I had to confront a question: What am I building—and who am I building it for?

Mentors and leaders played an enormous role in my life, and there is nothing wrong with helping build someone else's vision. But I knew I had to take ownership of what came next. Starting AvantGarde meant betting on myself in a completely different way and taking a monumental leap of faith.

Entrepreneurship looks exciting from the other side of success. When you're living it, it looks a lot more like risk. It means carrying responsibility for employees and their families. It means losing sleep over payroll, losing contracts, navigating chaos with clients at times and making decisions nobody else can make for you. You can (and should) build a strong management team around you, but in the end, the buck stops with you!

There have been countless times during my 15 years as a business owner when I wanted to give up, throw in the towel, sell my company or completely shift my focus out of sheer frustration for lack of progress. What kept pulling me back to my center was my why.

Your Why Has to Be Bigger Than the Hard Season

At first, my why was deeply personal. I wanted to change the trajectory of my family and build a legacy for them. Financial freedom is built through the hard work of entrepreneurs. I knew what instability and living paycheck to paycheck felt like, and I wanted something different.

Over time, my why became bigger than me. It became about creating meaningful careers for employees, mentoring women and showing young women that where they started did not have to determine where they finished. It became about legacy.

Money matters. A business has to generate revenue, pay people, yield profit to invest and grow. But money alone will not carry you through every hard season. Purpose will. Faith will. The people you're building for will. The vision of what could exist because you refused to quit will.

Lead Like the Woman You Are

One of the most freeing lessons I've learned is that I don't have to strip away the parts of myself or the unique personality that God gave me that make me who I am to be taken seriously. Many women feel leadership requires becoming harder, less emotional or less relational. I believe the opposite.

Women bring a powerful combination of empathy, emotional intelligence, resilience, intuition and relationship-building into leadership. I call mine my “leading with love” DNA. At AvantGarde, I've learned that people don't just want direction. They want connection. They want to know they are seen, valued and understood.

Leading with love does not mean lowering standards. Trust me, I make difficult decisions, and compassion without accountability isn't leadership. It means demanding excellence while remembering there is a human being on the other side of every business decision. Women shouldn't have to leave their greatest strengths at the door to lead. Bring them into the room with you.

Faith, Grit and Getting Back Up

People sometimes look at the chapters of my life—the White House, entrepreneurship, awards, speaking, Lost Girl—and see a straight line upward. It was anything but. My life has been a series of pivots, failures, people believing in me, God redirecting me, hard lessons, significant losses and getting back up. Again. And again. And again. As recently as 2025, we sustained a sizeable loss outside of our control that could have been a point of discouragement…but navigating it with the right posture, heart and plan was pivotal to forward movement.

That is why I talk so much about grit. Grit isn't pretending things don't hurt or having everything figured out. Grit is continuing to move when the outcome isn't guaranteed—even when you don't feel like it.

My faith in God and personal faith journey has been central to the path. Looking back, I can see how God used people, circumstances, closed doors and opportunities to shape me long before I understood what He was building. I call my story Lost Girl for a reason. I know what it feels like to be lost. But being lost in one chapter doesn't mean you stay lost forever.

When You Get in the Room, Bring Somebody Else

I didn't get here alone. Mentors saw things in me before I could see them in myself. People opened doors and told me the truth when my résumé alone didn't tell my whole story. No one—and I mean no one—makes it flying solo.

That is why one of my greatest responsibilities now is to do the same for someone else. It is why mentoring women is personal to me and why investing in the next generation through Girls of Legacy matters so much. Talent is everywhere. Access is not. Potential is everywhere. Mentorship is not.

What good is getting into the room if we never widen the doorway? Success isn't just about how high you climb. It is about who has a better chance of climbing because you did. That is legacy.

Women Are Building Legacies

When I started AvantGarde, I was trying to create a better future for my family. That is why National Women's Small Business Month means more to me than celebrating women-owned businesses. It is a reminder of what happens when a woman takes ownership of her future, walks into the room even when she is scared, gets back up after being knocked down and reaches back to pull another woman forward.

So to the woman sitting on an idea right now, questioning whether she's qualified or wondering whether a hard season means she made the wrong decision: don't shrink yourself. Don't wait until every doubt disappears. And don't let where you started convince you that you know where you're going to finish.

I was once the lost girl. Today, I'm a CEO, entrepreneur, author, mentor, wife, mother and a woman still very much in process. My past shaped me without defining me. My obstacles developed me without defeating me. And the seat I worked so hard to earn means more when I can use it to make room for somebody else.

A business can generate revenue. A legacy creates possibility for generations. This National Women's Small Business Month, let's celebrate the women building both.

Source: Wells Fargo, 2025 Impact of Women-Owned Businesses Report (data released 2025).