eaching Kids What We Were Never Taught

We are proud to share February 2026’s Friends and Family Fund Grant Winner: Cash Holland, founder of Financial BOSS, a nonprofit dedicated to educating, empowering, and elevating children so they understand how money really works.

Every month, Sky’s the Limit invests up to $2,500 in early-stage entrepreneurs through the Friends and Family Fund. These grants fuel ideas rooted in lived experience and built to solve generational challenges.

Cash’s work begins with a question many of us still carry.....

Do you remember what it felt like to struggle with money as a child?

“Hearing we can’t afford it without ever learning why.”

Meet Cash Holland

Cash Holland grew up watching financial stress shape everyday life. Bills were discussed, but understanding was not. The words “we can’t afford it” were common, but the explanation never came.

That gap followed many of us into adulthood.

Nearly half of adults say money negatively impacts their mental health. Anxiety. Sleepless nights. Stress that feels familiar because it started long before we had credit cards or bank accounts.

Cash recognized something powerful. These are not just adult money problems. They are childhood education gaps.

And research shows money habits are formed by age seven.

If the problem starts early, the solution should too.

Money habits are formed by age 7.

What we were not taught becomes what we struggle with.

Building What We Wish Existed

Cash founded Financial BOSS to make sure children do not learn about money through mistakes, stress, or silence.

At the heart of Financial BOSS is the Boss Squad Money Adventures Storybook, designed for children around age eight. Through relatable characters and real world lessons, the storybook introduces the four pillars of financial literacy:

• Earning
• Saving
• Spending
• Donating

But this is more than a book.

Around the storybook, Cash built Boss Student Success Packs that turn storytelling into hands on learning. Kids do not just read about money. They practice making financial decisions in safe, guided ways.

Validated by parents.
Piloted in Durham.
Adopted by community leaders.

Community Validation

Before asking anyone else to believe in Financial BOSS, Cash invested personal time, energy, and resources to prove it worked.

The validation came.

Parents and children participated in early Durham pilots. A commissioner publicly stated that Durham County families need this program and agreed to turn all seven county libraries into story hubs.

Why the Friends and Family Fund Matters

The February Friends and Family Fund Grant directly supports the preparation of 50 complete Boss Student Success Packs. These packs will support the Durham County Library rollout and Boys and Girls Club positioning.

This funding is not abstract. It is tangible.

It prepares materials for bookstore meet and greets. It places tools directly into children’s hands. It ensures that a child’s first relationship with money is built on confidence instead of confusion.

Cash’s larger vision calls on schools, libraries, and community organizations to adopt Financial BOSS at scale, purchasing hundreds or thousands of copies so financial literacy becomes the norm and not the exception.

February’s Winning Moment

Cash Holland was awarded the February 2026 Friends and Family Fund Grant after winning the live pitch competition.

Each month, the two most boosted pitches on the Sky’s the Limit platform, along with one wildcard, advance to compete live. Cash stood out by connecting childhood experience to adult reality and offering a proactive solution instead of a reactive fix.

Most financial education tries to repair damage after it happens.

Financial BOSS begins before the damage starts.

What’s Next for Cash Holland After Winning February’s Pitch Competition?

Fresh off the win, Cash is channeling the momentum into scaling Financial BOSS and expanding its impact. This post-interview highlights how community support and shared belief propel greatness, proving that when small businesses are backed by the right people, real progress follows.

About the Friends and Family Fund

The Friends and Family Fund provides early stage capital of up to $2,500 each month to underrepresented entrepreneurs launching bold, impact driven ideas. Through Sky’s the Limit’s community powered pitch process, more than $500,000 has been awarded to founders building stronger futures.

Every grant helps break cycles that would otherwise continue quietly for generations.

Want to Support Founders Like Cash?

Whether you are a donor, mentor, or community partner, your support helps children develop financial confidence before financial stress ever begins.

Sky’s the Limit exists so that bold ideas rooted in lived experience become scalable solutions.

👉 Join Sky’s the Limit and help build the future one child at a time.