The Homeschool How To

What if your kid's math class was the stock market?

Robert Grego pulled his 15-year-old son out of public school three days before 9th grade. He had no plan. So he asked his son what he actually liked, and built the year around it: Latin because he loves the Roman Empire, American and military history because he's obsessed with World War I, and no Shakespeare.

This year, his son's math is a YouTube channel the two of them run together called The Hostile Takeover. They break down stocks, read charts and solve for X with real dollar signs in front of it. His son makes the thumbnails, does the research, and they just got monetized.

Robert is a lawyer, hotel owner and dad of three. In this conversation we get into:

• Why schools teach Shakespeare (his answer: "Because they do")
• How much math a kid actually needs to make a living
• Why school teaches kids to memorize instead of think, and what that means with AI in their pocket
• The email he sent his school district about AI, and the reply he got
• How a professor making $300 during office hours got him into the stock market
• Whether 8 is too young to start learning about investing
• Paying your kids through your business and putting it in a Roth IRA (which, it turns out, I already did)

If you've ever worried that skipping the "normal" curriculum will leave your kid behind, listen to this one. Robert's son is learning digital marketing, business and algebra at the same time, and none of it came from a textbook.

Links:

• The Hostile Takeover on YouTube: https://www.youtube.com/@TheHostileTakeoverTV
• Market From Scratch playlist: https://www.youtube.com/playlist?list=PLNqyGrAdjjQE
• Robert's hotels on Lake George- the Sundowner, the Lake Haven, the Montreal and the Lake George Inn

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

If this episode got you thinking, follow The Homeschool How To and leave a review. It helps another parent find it.

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Her son could recite Goodnight Moon word for word at two years old, but he couldn't learn his letter names. He couldn't rhyme. He could read "redeemer" in scripture but not "an."

Liz from Idaho never planned to homeschool. Her husband wasn't sold on it either, so they made a deal: try kindergarten at home for a year, and if it didn't work, he'd go to school. After that year, her husband became the biggest homeschool advocate in the house.

Then came the reading. Five reading curriculums. Every Orton-Gillingham program she could find. Speech therapy, OT, an endless line for the neuropsychologist. When nothing worked, Liz figured, "it must be me," so she got trained herself. Today she's a dyslexia therapist, certified in EBLI, and in grad school for speech-language pathology.

In this episode, Liz explains the 3 D's in plain language:

• Dyslexia: reading
• Dysgraphia: handwriting and getting thoughts onto paper
• Dyscalculia: understanding quantity, time and counting

She also covers:

• The early signs she wishes more parents knew
• Why speech to print finally clicked for her son, who came up three grade levels in spelling in nine hours of instruction
• How audiobooks gave him a college-level vocabulary while he was still decoding at a 2nd-grade level
• Where to start with a kindergartner, and when to stop pushing
• Three-cueing, the "Reading Wars," and why she calls teaching kids to read her "civil disobedience"

Then the honest part. This year her son started school in 6th grade, and Liz gets emotional talking about it. If you've ever felt like putting your child in school means you failed, this conversation is for you. It isn't failure. It's paying attention to what your kid needs right now.

If your child is fighting you on reading, remember Liz's line: there's a difference between not being interested in reading and not being able to do it.

Resources mentioned:

For Speech to Print and Structured Linguistic Literacy, check out this page

Reading Simplified

Truth About Reading

EBLI

Sold a Story

Teach Your Child to Read in 100 Easy Lessons

Epic App

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

If you enjoy the show, please subscribe and leave a review. It helps more homeschooling families find us!

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What if you're homeschooling your child and you're constantly wondering, Am I doing enough?

What if they're not reading yet? What if you didn't get through all five subjects this week? What if your child spent most of the day playing, helping around the house, going outside, asking questions—and you still feel like you didn't “do school”?

That's exactly the kind of pressure we talk about in this episode.

My guest, Kiely Modiri, spent 10 years working in public education. She earned a master's in educational leadership, was on the path toward becoming a principal, and then became a mom and started questioning almost everything she had been taught about education.

Eventually, she created Alpine Village School and began working with parents to rethink what children actually need.

And one of the things that really stopped me was hearing that her daughter didn't really begin reading until around 8½ or 9—and Kiely wasn't worried about it.

Instead, she was paying attention to what her daughter actually needed at that point in her life.

We talk about homeschooling without recreating public school at home, why parents become so anxious about reading and academic benchmarks, what children can learn through free play and everyday life, and why Kiely believes connection should come before correction.

We also get into something I think a lot of homeschool moms will recognize: how much of our children's behavior can bring up our own childhood experiences, insecurities and fears.

If you've ever looked at your homeschool day and thought, We didn't get enough done, I think you're going to want to hear this conversation.

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

If you enjoy the show, please subscribe and leave a review. It helps more homeschooling families find us!

Connect with Kiely:

Website & Online Store: alpinevillageidaho.com

Instagram: instagram.com/alpinevillageschool

School website: www.alpinevillageschool.com

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What if your child isn't reading when you thought they would? What if they're not keeping up with the curriculum? What if you're starting to wonder whether you're actually doing enough?

That's exactly where this conversation goes.

Becky from Homeschooling Olympians homeschooled her five sons for more than 25 years. And one of those sons didn't learn to read until he was 10.

Instead of giving up on homeschooling, Becky learned to look at education very differently.

In this episode, we talk about the pressure homeschool parents feel to follow grade levels, check every box, finish every curriculum, and make sure their kids are “on track.” Becky shares how an incredibly overwhelming season — pregnancy, a child needing major surgeries, multiple grades, and too much curriculum — forced her and her husband to step back and ask a much better question:

What do we actually want our kids to know by the time they graduate?

That question became the foundation for their homeschool.

We talk about delayed readers, reading aloud, picture books, curriculum pressure, raising five boys, homeschooling through difficult seasons, and what Becky learned after looking back at 25 years of homeschooling.

And then there's the part I think every homeschool parent needs to hear: what happened to those five boys.

Their paths ended up looking completely different — from history and machining to filmmaking, music, science, business, and rowing — despite the fact that Becky says there were years when they did very little curriculum.

If you've ever wondered “Am I doing enough?”, “Is my child behind?”, or “What are my kids actually supposed to know?”, this conversation will give you a very different way to think about those questions.

Listen to the full episode of The Homeschool How To Podcast, and if it helps you rethink something in your homeschool, share it with another parent who needs to hear it.

From the episode:

Connect with Bekki: https://www.instagram.com/abetterwaytohomeschool/

13 Teeny Tiny Truth Bombs About Homeschooling

Honey for a Child's Heart

Sonlight Booklists

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

If you enjoy the show, please subscribe and leave a review. It helps more homeschooling families find us!

Support the show

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My guests this week, Owen and Christina, have five kids—and their family's answer to that question took them much farther than they ever expected.

It started with something surprisingly simple: their son wanted another thing.. "to be happy."

Around the same time, Christina watched a video about families who didn't have access to clean water.

So Owen and Christina did something most of us would probably never consider.

They shut off the water in their house.

For 10 days, their family walked to collect water, carried it home, washed clothes in buckets, and experienced firsthand how much of life we take for granted.

And then something unexpected happened.

When it was time to turn the water back on, they didn't want to.

That experience eventually led them to leave Canada and move their family to rural Guatemala, where their children have learned Spanish through immersion, worked alongside their parents, taken risks, made mistakes, participated in real community life, and learned skills you probably won't find on a traditional report card.

We talk about homeschooling, worldschooling, entitlement, purpose, community, raising capable kids, letting children fail, and why Owen and Christina don't see education as something that only happens in a classroom.

If you've ever looked at your homeschool and wondered, "Is this enough?"

This episode might make you rethink what education actually means.

Connect with Owen & Christina:

website: https://www.culturechalk.org/

Instagram: https://www.instagram.com/culture_chalk_travel/

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

If you enjoy the show, please subscribe and leave a review. It helps more homeschooling families find us!

Follow The Homeschool How To Podcast for weekly conversations with families who are doing things differently—and figuring out what actually works.

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What does your child actually need to learn—and how much formal homeschooling do they really need?

When I started The Homeschool How To Podcast, I wasn't even sure I was going to homeschool my own kids. I had a lot of the same fears so many parents have: Would my kids miss out? Would they have friends? Would they fall behind? Would I actually be capable of educating them?

More than 200 homeschool family interviews later, I've changed my mind about a LOT.

In this episode, I'm sharing what I've learned about homeschooling, socialization, curriculum, learning readiness, and what children actually need from us.

I'm talking about the fears I had when I started, why I no longer worry nearly as much about whether my kids are “on track,” and why I don't believe homeschooling has to mean sitting at the kitchen table with textbooks every morning.

I also share what homeschooling actually looks like in our house—including my son's completely unexpected opportunity to learn about horses several times a week because he wanted to. That experience has become one of the clearest examples of what I hoped homeschooling could be.

If you're considering homeschooling, you're a new homeschool parent, or you're constantly wondering “Am I doing enough?”, I hope this episode gives you a little more peace and confidence.

And remember: there is no one right way to homeschool.

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

If you enjoy the show, please subscribe and leave a review. It helps more homeschooling families find us!

Support the show

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Her son was all set to graduate from her homeschool and become a master mechanic — and then he enlisted in the Marines a month before he turned 18.

Christina Franco from Rooted Home Life joins Cheryl this week. She's a former public and private school teacher turned homeschool mom of five, and she gets real about the moment she realized it wasn't public school she had a problem with — it was school itself. They talk about her oldest son's surprise decision to join the Marines, the "mother's intuition" story from speaker Amber O'Neill Johnston that changed how Christina parents, why she doesn't believe in college for college's sake, and how family-style unit studies shape her very relaxed homeschool days.

You'll hear about:

• How a public school teacher ended up distrusting the entire system, not just one school
• The real story behind her son enlisting in the Marines right after graduating homeschool
• How being a blended family can affect homeschooling
• A mother's intuition story about a medical procedure gone wrong
• Why she doesn't believe in going to college "for the experience"
• How family-style unit studies work across five kids at different ages
• Her honest answer on putting her kids' faces online

Connect with Christina:

Instagram

YouTube

Podcast

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

Support the show

Instagram: TheHomeschoolHowToPodcast
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What happens when a former public school teacher sells everything to homeschool from a bus?

Three years after her first appearance on the podcast, Jennifer Gossett is back with an incredible update.

Since we last spoke, her family has traveled to 47 states, sold the bus, bought a home, and discovered that homeschooling doesn't have to fit inside one box.

In this episode we discuss:

• Why she left public education
 • What roadschooling really looked like day to day
 • Why they decided to stop living on the bus
 • Raising children with different learning styles
 • Dual enrollment and graduating with college credits
 • Whether homeschoolers really miss out on prom, sports, and friendships
 • Traveling America as part of your child's education
 • Why she believes it's okay to change your mind

Whether you're just beginning your homeschool journey or dreaming about traveling with your children, this episode is full of encouragement and practical ideas.

Connect with Jen:

https://www.instagram.com/un_hustled/

https://www.facebook.com/theunhustlebustle

https://www.tiktok.com/@unhustled

jens.a.cooker on TikTok 

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

Support the show

Instagram: TheHomeschoolHowToPodcast
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Can you really homeschool while traveling the world? What if homeschooling was actually illegal where you lived?

In this episode of The Homeschool How To Podcast, Cheryl sits down with Stacy, a homeschooling mom, worldschooler, and resilience coach whose family made the life-changing decision to leave Germany after discovering homeschooling wasn't legally allowed there.

Today, their family travels throughout Europe while homeschooling their three children through a blend of worldschooling, roadschooling, self-directed learning, and unschooling. They share what daily life really looks like, how they afford long-term travel, why they chose this lifestyle, and what their children have gained by learning from the world instead of a traditional classroom.

We also discuss:
 ✔️ Why homeschooling is illegal in Germany
 ✔️ What worldschooling and roadschooling actually look like
 ✔️ Waldorf (Steiner) education vs. homeschooling
 ✔️ How WWOOF and Workaway help families travel affordably
 ✔️ Helping children discover their strengths through interest-led learning
 ✔️ Building resilience in homeschooling families
 ✔️ Finding community while living a nomadic lifestyle
 ✔️ Common fears parents have before homeschooling — and why it doesn't have to be all or nothing

If you've ever wondered whether homeschooling could look completely different than the traditional model — or if you've dreamed of traveling with your kids while giving them an incredible education — this conversation will inspire you to think outside the box.

Resources mentioned:

• WWOOF (Worldwide Opportunities on Organic Farms)
• Workaway
• Stacy's resilience coaching information-Instagram- @resiliencewithstacy
  www.resiliencewithstacy.com

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

If this episode encouraged you, please subscribe, leave a review, and share it with a friend who's considering homeschooling.

Support the show

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What do you do when the school waits until the night before the last day of school to tell you your child is failing — and it turns out they broke his own IEP to do it? 

Dr. Amy Moore joins Cheryl this week. She's a cognitive psychologist and former teacher who left the classroom to research why struggling kids kept getting missed. She's also raised three sons — now 27, 25, and 21 — all neurodivergent, all homeschooled differently based on what they actually needed. 

They get into the real story behind pulling her oldest out of school in 6th grade after a last-minute email about 20+ missing assignments his 504 plan should have flagged much earlier. From there, Dr. Amy breaks down the difference between neurodiverse and neurodivergent, why social-emotional learning programs in a classroom of 30 can't replace what happens one-on-one at home, and how to tell if your child is dealing with a content gap or a skill gap when something isn't clicking. 

You'll hear about: 

• The night her son's school broke its own legal accommodation — and what she did the next morning
• Why co-regulation (not curriculum) is the missing piece in most SEL programs
• How dual enrollment programs like Colorado Early Colleges let homeschoolers earn college credit for free
• Why a major meta-analysis found a leading reading approach wasn't moving the needle — and what she says actually is
• Her advice for any parent who's terrified an IEP means they can't homeschool

If you're staring down a diagnosis, an IEP meeting, or a kid who just isn't clicking with the curriculum you picked — this one's for you.

Connect with Dr.Amy:

www.thebrainymoms.com

www.amymoorephd.com

www.instagram.com/thebrainymoms

Ready to homeschool but wondering where to start?

📘 Grab my book, So You Want to Homeschool? Everything You Need to Know Before You Start

🎓 Need a step-by-step plan? Check out Cheryl's mini-course, How to Work and Homeschool 

📚 Still wondering, "What do I actually teach?" My guide walks you through exactly what homeschool families focus on by age and subject.

If this episode encouraged you, please subscribe, leave a review, and share it with a friend who's considering homeschooling.

Support the show

Instagram: TheHomeschoolHowToPodcast
Facebook: The Homeschool How To Podcast