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Nine Pregnancies, Five Homeschooled Kids, and the Wealth Blueprint My Grandmothers Left Me [Generational Wealth and Financial Freedom for Homeschooling Families]
Episode 2918th May 2026 • Homeschool Money • Anthony Obey, Crystal Obey
00:00:00 00:22:16

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What if the blueprint for financial freedom for your homeschooling family has been sitting in your family history all along?

In this milestone birthday episode, Crystal Obey shares what she discovered at 45 about the generational wealth strategies her grandmothers built long before homeschool money was a conversation.

This is the mindset foundation the entire Homeschool Money podcast is built on.

Take the full FREE Class: FREE INTRO CLASS: Get $30,000+/Yr to Fund Your Homeschool Without a 9-5 Job

In This Episode, You'll Discover:

  • The generational wealth blueprint Crystal's grandmothers built
  • Why financial freedom for homeschooling families starts with a mindset shift, not a spreadsheet
  • How homeschooling five kids while running a business is training your children
  • The name your farm challenge
  • Why the homeschool lifestyle is one of the most underrated financial strategies
  • What turning 45 with intention looks like as a homeschooling entrepreneur
  • How Texas Education Freedom Accounts (TEFA) and current education funding shifts create a once-in-a-generation opportunity for families paying attention

Perfect for You If:

  • You want to build generational wealth while homeschooling without a traditional 9-5 job
  • You are looking for a mindset foundation before diving into specific income strategies and homeschool funding tools
  • You feel like you are behind and need a reminder that the forties and beyond are a launching pad, not a finish line
  • You believe homeschooling costs your family financially and want a new framework for thinking about the return on that investment
  • You are ready to stop spending what you have and start investing it strategically for the next generation

Transcripts

Speaker:

Okay, so I turned 45, and I wanna be

clear, I did not wake up and feel like

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a woman who had it all figured out,

draped in linen, morning light hitting my

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face perfectly, birds chirping my name.

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No.

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The very first thing I did in

my 45th year of life, the very

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first thing, was change a diaper.

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Welcome to my world.

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But honestly, even that felt symbolic

because that is exactly who I am.

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I don't just talk about

investing in the next generation.

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I am quite literally in the dark,

in the middle of the night, doing

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the unglamorous work of raising one.

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Now, I also have a

tradition with my brother.

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He and I share a birthday.

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Not twins.

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He is two years younger than me, which

means he's never once in his whole life

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had a birthday that was entirely his own.

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So every year we have

a little competition.

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Whoever says happy birthday

to the other one first wins.

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There's no prize, it's just

like silent satisfaction.

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So this year, this year I had a plan.

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I was ready.

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I was gonna text him the

very second midnight hit, and

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then my kids started talking.

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You know how kids do that thing where

they pick the exact moment where

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you need 10 seconds of silence to

unleash a full congressional debate?

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That happened.

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I got distracted, and when I finally

picked up my phone to send that

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text, his text was already there.

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He beat me again.

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Now I have to wait a whole other

year, and I'm already strategizing.

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But anyway, I sat there on the sofa

with my family finishing our movie and

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I thought, "Huh, I'm genuinely happy."

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Not the performed kind of

happy, not the I'm fine kind.

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The real settled, nothing

to prove kind of happy.

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And I wasn't expecting that because

nobody told me 45 could feel like this.

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Nobody told me that 45 would be the

year I feel more fearless than ever.

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Nobody told me that everything I've been

building, the marriage, the family, the

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business, the legacy, would start to feel

less like effort and more like momentum.

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Nobody told me that the 40s aren't the

finish line, they are a launching pad.

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So today, at 45 years old, I'm Crystal

Obie, and I wanna talk to you about what

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I've been building, where it came from,

and where I'm absolutely, intentionally,

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joyfully going because I think it's

gonna change the way you think about

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your own family's financial future.

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A fast-growing number of parents

are starting their homeschooling

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journey, while others have

been homeschooling for years.

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All of these parents are asking one big

question: How can I afford to homeschool?

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We're here to answer that important

question once and for all.

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Hi, I'm Crystal Obie.

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And I'm Anthony Obie.

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We've been homeschooling our five kids

for 13 years, and we funded it through

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our online consulting business that

we've been running for over 17 years.

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Now, we're combining Crystal's financial

coaching expertise with my digital

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marketing background, where I help

entrepreneurs launch and sell online.

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We're here to help fellow

homeschooling parents self-fund

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their homeschool journey and create

lifestyle businesses for financial

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freedom without a nine-to-five job.

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Are you ready to start living life

on your own terms and make your

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homeschooling experience a lot more fun?

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Well then sit back, crank up the volume,

and enjoy this episode of Homeschool

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Money.

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So welcome to the

Homeschool Money podcast.

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I'm so glad you're here.

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Most people turn 45 and look

back And I did look back, but

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what I found there wasn't regret.

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What I found was a blueprint I

didn't even know I was holding.

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So let me tell you about my grandparents.

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On one side of my family, there was a farm

in Tennessee, and this wasn't just a farm

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in the way we romanticize farms today.

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It wasn't a lifestyle brand

or a homestead hashtag.

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This was land with purpose.

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My grandparents used that farm

to do something extraordinary

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during one of the most painful

migrations in American history.

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After the Civil War, Black families

were moving north, heading to cities

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like Chicago looking for safety,

opportunity, and a fresh start, and the

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journey was long and hard and expensive.

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And my grandparents,

they opened that land up.

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They said, "Come, work a season,

earn what you need, then keep

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moving toward your dream."

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They weren't running a charity.

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They were running a bridge.

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They looked at people in transition and

said, "We have something, and we will use

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it to help you get where you're going."

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Hey, real quick, if you're liking the

show, hit follow so you don't miss a

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single episode, and drop a five-star

rating and a review to let us know that

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you're loving the content and tell us

what topics you'd like us to cover.

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This will help more people find the show.

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And please share this episode

with a friend, your co-op,

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or anyone who needs it.

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They'll be glad you did.

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Now back to the show.

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That's legacy work.

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That's generational thinking, and I

didn't fully understand until recently

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that I've been doing the exact same

thing, just in a different century

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with a different kind of land.

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And then there's my other grandmother.

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World War II changed everything for her.

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The men went to war, and suddenly,

women who had been told their place

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was cleaning other people's houses

were now needed in the shipyards.

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She got to build battleships.

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She got paid wages she

had never seen before.

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And you know what she did with that money?

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She didn't spend it on things.

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She didn't upgrade her lifestyle.

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She bought land in Indiana, and

that land, that quiet, unglamorous,

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nobody's putting it on Pinterest piece

of land provided housing security

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for five generations of our family.

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Five generations.

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I've been sitting with the math on that.

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If you tried to give five generations

of a family housing security today

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through rent, through mortgages,

through any modern financial tool

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available to us, you would be talking

about hundreds of thousands, possibly

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millions of dollars over a century.

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My grandmother did it with one wartime

paycheck, one decision, one piece of land.

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She never wrote a book.

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She never had a platform.

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She never gave a Ted Talk.

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But she made one strategic decision

with her resources, and that decision

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is still paying off for people who

weren't even born yet when she made it.

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That's the energy I'm

stepping into at forty-five.

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Here's what I've come to understand.

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I have spent the last forty-five years

in training, and I mean that sincerely,

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not as a cliché, but as a fact.

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Twenty-four years of

marriage, twenty-four.

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That's not just love, that is practice.

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Practice in partnership, in communication,

in building something with another

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person, even when it's inconvenient and

imperfect and absolutely not what either

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of you imagined it would look like.

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That's a skill, and it

has made me sharper.

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Five children homeschooled

while running a business.

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Homeschooling my children has not

been a sacrifice of my ambition.

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It has been the incubator for it,

because when you are responsible for how

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five different human beings understand

the world, you get very clear, very

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fast about what actually matters.

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You stop being vague.

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You stop accepting systems that

don't serve your family, and

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you start building your own.

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I wanna say something that I don't

think gets said enough in any space

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where homeschooling families gather.

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Homeschooling is not

a financial sacrifice.

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It is a financial strategy.

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Most people only look at what it

costs, the curriculum, the time,

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the income you stepped away from.

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They never look at what it builds.

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They never calculate the value of a

child who graduates knowing how to think,

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knowing how to work, knowing how to earn,

because they watched their parents do it.

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They never count the wealth of a family

that stayed close, stayed intentional,

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stayed aligned, because alignment is the

foundation everything else is built on.

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I have been an entrepreneur throughout

this season of life, and my children

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are watching me fail and get back up.

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They're watching me negotiate,

create, vision cast, and execute.

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They are learning, without a single

worksheet, what it looks like

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to build something from nothing.

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That is not a cost.

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That is a curriculum, and it is the

most valuable thing I could give them.

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In the weeks ahead on this podcast,

Anthony and I are going to break down

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exactly what that strategy looks like

in real numbers, the wealth tools,

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the income systems, the funding most

families are leaving on the table.

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But today, I wanna give you the

foundation, the mindset that everything

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we're about to teach you is built on.

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We are in the middle of the biggest

shift in American education in a

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generation, maybe in our lifetime.

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The conversation about how children

learn, where they learn, and who pays

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for it has cracked wide open, and

families who are paying attention right

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now, who are making strategic decisions

right now, are going to be the ones

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who come out of this transition with

options My grandparents' farm was a

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bridge for families in transition.

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I am building a bridge for

families in transition.

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That's why I do this work.

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That's why I show up.

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That's why this is not

just a business to me.

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It is a calling that has been

echoing through my bloodline

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for over a hundred years.

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I wanna talk about something that

doesn't come up enough in spaces

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where women gather to talk about

business and legacy and education.

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It's the body.

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I'm forty-five.

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My body is changing, and I have decided

fully, completely, and without apology

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to embrace every single bit of it.

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Because here's what I know.

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This body carried five children,

four miscarriages, including the five

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births, so nine total pregnancies.

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This body showed up on the hard days.

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This body got back up.

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Every change it's going through right

now is just evidence that it has

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been working, and I refuse to spend

the next chapter of my life at war

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with the vessel that got me here.

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I also wanna share something

a great aunt told me.

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I used to call her every week

because she was the kind of woman

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you call every week if you're

smart enough to know what you have.

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And she told me something I wanna

give to you today as a gift.

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"In your forties, you are only

almost halfway through your life.

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You have so much you can still do.

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There is no rush."

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You hear that?

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She said, "No rush."

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I sat with that.

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I let it rearrange something in me because

so much of what makes us frantic as

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parents, as women, as entrepreneurs is

the false belief that we are behind, that

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the window is closing, that we should

have already arrived somewhere by now.

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But what if the forties

are not the finish line?

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What if they are a launching pad?

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I have done the hard work

of clarifying my values.

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I know who I am.

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I know what I believe.

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I know what I will and will not do.

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And that clarity, that took

forty-five years to earn.

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You cannot shortcut it.

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You cannot buy it.

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You cannot borrow it.

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You just have to live it.

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I have a dream business, and

I can see it clearly now.

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I am in my dream city.

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I have a full cup.

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Not a cup that is barely holding on, not

a cup that is half full because I keep

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pouring out and forgetting to refill.

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A full cup, and I am

positioned to walk in overflow.

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And here's what a full cup

means for me financially.

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I am not making money

decisions from scarcity.

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I am not saying yes to the wrong

opportunities because I'm afraid.

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I am not underselling what I

have built because I am not

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sure it's worth full price.

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That shift from scarcity to overflow

is the most valuable thing I own at

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forty-five, and it did not come from

a course or a coach or a spreadsheet.

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It came from forty-five years of living,

building, failing, and getting back

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up That shift is completely available

to you, and that is exactly what this

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podcast is here to help you find.

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Everything hard that happened, and

there for sure were hard things.

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There were seasons I really

wouldn't wish on anyone.

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Every single struggle was worth

it, not because suffering is noble,

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but because I am still here, and

I know things now that I couldn't

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have known without going through it.

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Hey, I hope you're enjoying the show.

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We'll get right back to the

discussion, but I do wanna talk

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high level with you real quick.

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You see, transforming your finances so

you can self-fund your homeschooling

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journey without a nine-to-five

job takes a roadmap, right?

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A- and you may be wondering,

where do I even start?

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Start at step one.

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Our Homeschool Money Makeover program

breaks it down into five practical steps

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that help any family achieve a financially

abundant homeschooling lifestyle.

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Step one: install the

abundance operating system.

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Most people believe that they need two

nine-to-five jobs to make it in America.

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The truth?

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With all the technology and the

tools available today, there's never

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been an easier time to generate six

figures a year in income working just

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15 to 20 hours a week than today.

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When you have a strong why for

homeschooling and you know the

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real costs, you unlock the courage

that you need to become a money

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magnet without a nine-to-five job.

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Step two: get crystal clear about what

you're gonna do with your first $1,000

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that you make outside of your day job.

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Write down specific homeschool

needs that $1,000 can cover.

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Yes, this is a small amount, but if you

can learn how to set a target of making

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your first thousand dollars outside of

your nine-to-five job, that's going to set

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a fire in your belly and the determination

that you need to make the next $100,000.

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Step three: find all the money falling

through the cracks in your budget.

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With Crystal's three financial coaching

certifications, listen, she's gonna

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help you be able to streamline your

budget and free up money without

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sacrificing your favorite things.

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You can't build a strong financial

future with money falling

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through your pockets, right?

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So let's plug up the leaks.

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Step four: discover new ways to

make money and claim free money

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available for homeschooling families.

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We discuss grants, scholarships,

proven fundraising opportunities that

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savvy homeschoolers are using, and

we show you how to use them, too.

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Step five: launch or scale your

money-making success system to completely

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replace your nine-to-five job income.

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Whether it's a side hustle, a freelance

work, or a new business, identify your

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single most viable opportunity and turn

that into $3,000 in income, $5,000,

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$10,000 a month in income, or whatever

you need to feel financially abundant.

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Implementing these five streamlined

steps will make you feel more

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financially empowered than ever before.

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You will gain the momentum that you

need that by step number five when

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you're making more money- You're

going to feel unstoppable financially.

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Through our marketing consulting

business, we've helped literally

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hundreds of entrepreneurs

build online selling machines.

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That's what we do in our business Life and

Launches, and we share our million-dollar

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automated selling system with you inside

the Homeschool Money Makeover program.

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Inside the course, you're gonna get

all the video lessons, worksheets,

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templates, and guides that you need

to walk through all five of the

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steps to transform your finances.

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And right now, during our special

introductory offer period, you'll

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get bonus gifts plus our lowest

enrollment price ever, making

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it easy to enroll and make your

first thousand dollars back fast.

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Go to homeschoolmoney.com

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to watch our free class, and then you're

gonna get an inside look at the full

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Homeschool Money Makeover program.

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Don't wait.

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Go to homeschoolmoney.com

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to start the free class and enroll

into the full program today.

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Now I'm done having children.

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I have energy, I'm happy, and

I welcome with both arms wide

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open the next forty-five years.

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So what does intentional living

at forty-five actually look like?

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It looks like starting

a new legacy in Texas.

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My grandparents had Tennessee and Indiana.

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I have Texas, and I am choosing Texas

on purpose, not by accident, not

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just because of the weather or the

culture as much as I love them both.

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I am choosing Texas at a historic

moment, a moment when this state

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is changing the rules of education

funding in ways that will benefit

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families like ours for decades to come.

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Texas just made a billion dollars

available to help families choose

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how and where their children learn.

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We are planting here.

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We are building here, and I am

inviting every family listening

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to plant and build with us.

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Just like my grandmother looked

at her wartime paycheck and said,

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"This is a bridge, not a spending

account," I am looking at this moment

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in Texas and saying the same thing.

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The tools are here.

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The funding is here.

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The community is here.

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What are we going to build?

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It looks like building a business

that creates bridges for families

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the way my grandparents created

bridges for people in transition.

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Because the families I serve, the

ones navigating education funding,

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the ones trying to figure out ESAs

and homeschool co-ops and scholarships

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and real estate and all the tools

available to them, they're in transition.

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They're moving towards something

better for their children, and I

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want to be the farm that they stop

at to get resourced and refueled.

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It looks like showing up on stages

and in rooms and on podcasts and in

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communities and saying, "You have more

options than you think, and I am living

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proof that it is possible to build

something intentional, sustainable, and

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generationally meaningful, even while life

is full and loud and beautifully chaotic."

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It looks like my marriage getting richer.

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Twenty-four years in, and I am more

committed to this partnership than I ever

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have been because I understand now that a

great marriage is one of the most powerful

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wealth-building tools a family has.

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The alignment, the shared vision, the

trust, it compounds just like interest

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It looks like my children watching

their mother step fully into her purpose

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and learning by osmosis that purpose

is not something you stumble into.

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It is something you build brick by brick,

year by year, generation by generation.

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That is what turning 45

with intention looks like.

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Not slowing down,

accelerating, but with wisdom.

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Now, before I let you go, I want to

leave you with something to sit with

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this week, because every episode I want

to give you something that moves you,

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not just something that informs you.

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So here's your challenge.

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I want you to name your farm.

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What I mean is this.

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My grandparents had a farm.

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They had a resource, which was

land, and they used it strategically

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to build a bridge for others.

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My grandmother had wages she had never

earned before, and she turned them

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into a five-generation housing legacy.

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They both had something, and

they decided what it was for.

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You have something too.

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Maybe it's knowledge.

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Maybe it's a network.

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Maybe it's a financial tool you

haven't fully activated yet.

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Maybe it's time you've been

spending but not investing.

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Maybe it's your story, your real

complicated, beautiful story that

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another parent desperately needs to hear.

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Maybe your farm is 15 years of

special needs parenting and everything

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you know about navigating IEPs and

funding that other families don't.

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Maybe it's a nursing degree that

could become a home income stream.

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Maybe it's a paid off car that

frees up $600 a month you could

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redirect into your children's future.

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Maybe it's a spare bedroom

sitting empty while another

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family needs affordable housing.

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Maybe it's your debt-free story, the

one you've been too embarrassed to

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share, that someone in your circle

is desperate to hear right now.

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What is your farm?

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And who are you letting stop there

on their way to something better?

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Write it down.

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Just one thing.

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Don't overthink it.

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Your legacy is not waiting

for you to be ready.

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It's waiting for you to be willing.

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So here's my birthday ask.

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I wanna hear your farm.

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I genuinely want to know.

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So please send me a message or tag

us on social because when I see your

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:

farm, I am going to show up for it.

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:

I'm going to share it.

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:

I'm going to celebrate it.

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This is my birthday promise to you

because this is not a one-way show.

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This is a movement, and movements

are built when people name what

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:

they have and decide to use it.

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:

So tell me your farm.

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:

I'm listening.

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:

And if you wanna keep building, if

you wanna figure out how to take that

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:

thing and turn it into a real funded

strategic plan for your family's

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:

future, I wanna help you do that.

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:

Come find me.

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:

The link is in the show notes.

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:

Let's build this together.

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:

Thank you so much for spending your time

with me today, especially for my birthday.

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:

This community is part of my overflow,

and I do not take that lightly.

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:

I'll see you next week

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:

If you liked today's episode,

make sure you tap the follow

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:

button so you never miss a thing.

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:

And if it helped you, share it with

a friend or your homeschool group.

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:

Sharing is caring.

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:

Do you love free stuff like me?

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:

Sign up and watch our free beginners

class called Get 30,000 a Year to fund

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:

your homeschooling without a 9 to 5 job.

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:

When you sign up, you'll get instant

access to the class, and you'll

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:

get our weekly newsletter with

tips and strategies to make your

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:

homeschooling journey affordable.

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:

Go to homeschoolmoney.com

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:

and register right now.

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:

Ready to get your homeschool money?

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:

Head over to homeschoolmoney.com

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:

to enroll in the full Homeschool

Money Makeover course.

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:

You'll get the tools, templates,

and step-by-step help to find

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:

your first $1,000 fast and create

30,000 or much more every year.

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:

Each module of this program is designed

to transform your finances and help you

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:

experience financial abundance so you

have the flexibility and lifestyle freedom

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:

to homeschool your children without

a 9 to 5 job and without sacrificing.

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:

And right now, we have an amazing limited

time offer that gives you huge savings

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and bonus gifts you're going to love.

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:

Go to homeschoolmoney.com

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to enroll today.

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:

And don't forget to give us some love

with a five-star rating and review.

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:

It'll help more people find our show.

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Have a great day.

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Bye.

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