The Homeschool How To

The Homeschool How To Podcast

Thinking about homeschooling? Start here.

Real families. Real strategies. Real life. 200+ interviews with homeschooling families — everything you need to take a leap.

You've asked for it!

I’ve finally compiled everything I’ve learned from interviewing homeschooling families into one easy guide for YOU! Click here to grab your copy!

Behind The Mic

Hi, I’m Cheryl—your fellow conspiracy-loving mama who firmly believes the government has no place in raising my kids.

Here’s the kicker: I had zero experience with homeschooling when I realized I wanted to keep my kids out of the school system. I thought homeschoolers were weird and spent their days sewing and whittling. Could I blend our world with homeschooling? Would my kids resent me for missing out on traditional experiences like the prom and football games?

I didn’t know, so I set out on a mission to learn from the experts.

I began my podcast interviewing homeschooling families so I could explore all the ways people are homeschooling, breaking free from the confines of cubicles and classrooms to embrace a life of freedom and curiosity. This journey has been life changing and led me to leave my 16-year government career to fully embrace the homeschooling lifestyle.. and I want to help you do the same!

Join me on this exciting journey as I interview seasoned homeschoolers, uncover creative approaches, and share what I’m learning along the way!

Grab My FREE 30-Day Homeschool Quick Start Guide!

New to homeschooling and not sure where to begin? This free 30-day guide walks you through exactly how to get started — step by step.

Free 30-Day Homeschool Launch Blueprint cover

👉 FREE GUIDE HERE

Latest Episodes

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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#190: He Pulled His Son 3 Days Before High School. Now Math Class Is the Stock Market.

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#190: He Pulled His Son 3 Days Before High School. Now Math Class Is the Stock Market.

October 10, 2026

Cheryl - Host

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#189: “It Must Be Me”: The Signs of Dyslexia Every Homeschool Mom Should Know

October 3, 2026

Cheryl - Host

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#188: Your Child Doesn’t Need to Read by 5: What a Former Teacher Wants Homeschool Parents to Know

September 26, 2026

Cheryl Daley

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Testimonials

"I love how she is delving into how education in a public setting is making a lot of people question its methods and that homeschooling can be a viable option for people, and has so much to offer families. I myself was homeschooled. Growing up, our parents were looked down on, it is so nice to see the podcast showcase how many people have been happy with their choice to homeschool."

"This has been the most useful podcast! Questions you’ve asked are exactly what I had in my head. The the noise of people around me who just don’t get it yet, doesn’t bother me as much, as I’m learning through you and your guests about all this! Thank you so much for doing this!."

"A perfect podcast for those exploring a homeschooling journey. Every episode is packed full of resources! So many families have been forced by the government to homeschool. Get prepared now before the woke corruption comes to your school!"

"Great podcast for parents who want more info on whether homeschooling is a good option for you or not. Crazy to see how different each state operates. Thanks Cheryl for putting in the work for us."

"Love this podcast! The conversations are great. I’ve been going back and forth for some time now about whether or not I want to homeschool. My husband is also listening with me and open minded now! You’re giving such good insight! Keep going🙌🏼❤️"

"Very informative and the host has a smooth, educated voice with great insight and questions. She actually sounds just like Megyn Kelly! Very professional."

"I love this podcast so far. I’ve learned so much from listening as I get other stuff done. I am about to start homeschooling my oldest as he is turning 5, so this is perfect for me at this time. Excited for more episodes!"