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Team Spotlight: Lucy Winchester

Charter School Capital

October 7, 2020

Lucy Winchester - Office Manager at Charter School Capital
Lucy is a Mother, free spirit, and Charter School Capital’s first employee. Growing up in El Paso, Texas, with four sisters and two brothers, she grew up learning to follow where life took her and support the global community. Now, over a decade in the charter finance sphere, she reflects on how far Charter School Capital has come.


How did you meet Charter School Capital?

I’ve known Stuart (CEO of CSC) for 28 years; we met in the 90s at a firm where I was initially his Executive Assistant. We’ve always worked well together. I’m the sound, constructive side to his ever-changing, creative genius. After initially working together, we always stayed in contact. Any new project he started, I was there to help with the groundwork.
One day he called me and said, “Brad and I have this idea, it’s a passion project about schools. It’s never been done in the market before, so it’s something new, we’re going to try to see if it works. Are you up for moving to Portland to help us set up?” And I said, “Sure!” That’s what I always say to Stuart’s ideas. There I was, basically inventing the wheel for every part other than finance for Charter School Capital.

How would you describe CSC and your position?

Over the past decade, my position has shifted from the first employee to the office manager. I feel my role has always been the same. I am part of the base that built our platform and help maintain its shape. When I started, set up a system to collect information from the schools to create the receivables, setup the office, and start an HR Department for our new company. Now, I’ve morphed into the office management aspect of Charter School Capital. I take pride in my role, being a trusted asset that supports the team and vision of Charter School Capital.

What brings you joy?

My family brings me the most joy. I have a son and two grand-doggers, a pug named Sophie and a Boston-terrier named Charlie. They tend to keep me on my toes during the day.

What did you want to be when you grew up?

Back in the 70s, I was a hippie, groovy child. I remember wanting to travel, help others, and go on the next adventure. Later on, I learned that my personality type is supporting others while being independent and free-spirited, I’ve always fit that mold.

Over the years, what wisdom have you learned?

I’ve always been a person who went where the wind took them. At one point, I took a trip to Puerto Vallarta, Mexico, with my friends, and we loved it so much we decided to stay and move there. So I would say, live without regrets and pursue a life you want to live.

From your position, how do you impact charter schools?

From the beginning, I’ve been able to support schools that were operating in their church basements and help them into a building that allowed them to double their students. We found out early on that our efforts at Charter School Capital could go a long way. In the past, I would have close relationships with schools and their leaders, now I help the internal connections and functions of CSC to ensure our mission continues.

What gets you out of bed in the morning?

Feeling like I have a purpose in helping impact people’s lives, my faith, my family, and taking care of others. Family is a big deal to me; my four sisters and I Zoom call them every night. CSC has become part of my family; that’s why I’ve stayed since its birth.

What’s something about you that might be surprising?

Until recently, I’ve been riding a Harley motorcycle for the past ten years. When I first moved to Oregon to help setup Charter School Capital, I convinced my best friend Claire to move up here, and we got our Harleys together. Once Claire came up here, Stuart (CEO) agreed we should hire her, and she’s been working with us in various hats and positions. Stuart and Claire were the start of the “CSC Wamily” up here in Oregon ever since.

If you could create a New Class Subject, What would it be?

How to Support Yourself. Showing students the necessary skills in life like cooking easy meals, balancing a checkbook, and how to apply to jobs. Skills that don’t have an expiration date, and you can always rely back on upon.

In your view, what does the world need more of? Less of?

More kindness and acceptance.
Less hesitance.
If people treated others with kindness without asking anything in return, we would see a global impact. Kindness can make a difference in someone’s life, and act like a butterfly effect, encouraging others to act selflessly.

What do you hope to see for the Future of Charter Schools?

I hope to see more acceptance and understanding of charter schools. What I admire most about the charter community is their dedication and passion. They are in it because they love to teach and help others, not because there’s a paycheck. I wish that was understood on a grander scale.

What do you hope to see for the Future of CSC?

In those first months, I thought at best we would be able to sell Charter School Capital, and then we would follow more passion projects around education. Luckily, we never sold, and instead, we’ve seen a movement of finance groups following our model. We’ve been able to evolve, shift to serve the market, and grow. My hope is for CSC to continue to expand, find more ways to help schools, and fund different aspects surrounding education and community.

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