The 2026 Homeschool Boss Midwest Summit
As homeschooling continues to evolve, we want to make sure that our community is equipped with the tools and support needed to evolve with it.
The 2026 Homeschool Boss Midwest Summit brings together homeschool group leaders, co-op directors and microschool founders for a full day of inspiring speakers, practical breakout sessions and real community built around one shared mission: building strong learners, strong schools and strong futures. Whether you’re launching your first microschool, growing your co-op or looking for better ways to develop your program, you’ll leave well-equipped with the tools to make confident, purposeful decisions for every student in your care. Come ready to learn. Leave ready to build.
The Conference
Speakers & Activities
A roster of heavyweights in their respective industries will bring practical, actionable insight through engaging sessions.
Food & Refreshments
Enjoy breakfast, lunch, and refreshments throughout the day, including coffee and tea to keep you energized and ready to connect.
Networking
Exchange ideas, build partnerships, learn from each others’ experiences. Challenge yourself to strengthen your community.
Schedule
Note: Speakers will be announced closer to event date.
Speakers
Chad Kinart
CEO, Homeschool Boss
Learn More About Chad
Chad Kinart is the CEO of HomeschoolBoss, where he leads the company’s work in norm-referenced assessment for K-12 families and educators. His career connects three worlds: sports medicine, assessment, and education technology. That mix gives him a practical view of what it takes to help learners, and the people supporting them, grow stronger.
Chad began his career as a certified athletic trainer (ATC). He later managed the exam-development process used to certify athletic trainers nationwide, working with subject-matter experts, volunteers, and vendors to keep a high-stakes assessment rigorous and fair. That experience grounded him in how good measurement is built and why it matters.
He then moved into K-12 education technology, where he helped schools and districts align instruction and assessment. At Instructure he was a Senior Sales Executive for Academic Benchmarks and earned a place in the 2023 Presidents Club. He later worked with Via TRM. Throughout, he has championed evidence-based decision-making and the idea that data should serve both students and budgets.
Chad holds a Master of Science and an MBA, with graduate study at the University of Nebraska at Omaha. He lives in the Twin Cities, and he describes his approach simply: living his best life one day at a time and working to make the world a better place.
Kathleen Cotter Clayton
VP, RightStart™ Math
About Kathleen
Kathleen Cotter Clayton is the daughter of Dr. Joan A. Cotter, author and developer of the RightStart™ Mathematics program. Kathleen is involved with curriculum development and has written or co-authored 18 manuals. She travels, teaches online middle-school classes, and speaks across the US and internationally, sharing the mission to help children understand, apply, and enjoy mathematics.
Kathleen has a Bachelor’s degree from the University of Minnesota and has two Masters Degrees from the University of Mary in Bismarck, North Dakota. In her spare time, Kathleen designs and creates mathematical quilts and loves to travel all around the world.
Oliver Stremple
Founder, Stress Less Bookkeeping
About Oliver
Oliver lives in South Minneapolis in a 114-year-old house with their spouse, two kids under 5, a tiny cat, and an old dog. They have always had an insatiable desire to organize information and ideas. As a homeschooler in rural Wisconsin, they made their first graph to chart how many times their donkey Brighty brayed each day. They have always been involved in social justice and grassroots organizing and this led to a Bachelor’s degree in social work and a career in nonprofit operations.
In 2025, they started Stress Less Bookkeeping to support small business owners and community members who do not love numbers make sense of their financial processes. Being self-employed has been everything they hoped it would be, allowing more time for art, sewing, quilting, native plant gardening, and homeschooling their kids.
Alex Roosenburg
Founder Development Specialist, National Microschooling Center
About Alex
Alex Roosenburg started her career as a classroom teacher, then a technology coordinator in International Schools. She became a school administrator at the age of 30, and after doing that for a few years, decided to open her own microschool, with a focus on future-ready skills and equitable tuition structures. At the same time, Alex worked as a coach for 4.0 Schools, to help fellow education entrepreneurs build out and pilot their ideas. This led her to meeting Don and Ashley at the National Microschooling Center.
Alex now works as a coach to groups that are starting schools, and as a Founder Development Specialist at the Microschooling Center, helping microschool founders at any stage in their journeys of microschooling.
Michael Wall
Youth Voter Outreach Specialist, Office of Minnesota Secretary of State
About Michael
Michael is the Youth Outreach Specialist at the Office of Minnesota Secretary of State. He specializes in supporting success and the mission of the client through the building of relationships. He leads the day-to-day operation for various youth voter outreach programs at the Office of Minnesota Secretary of State Steve Simon.
Theresa Redfern-Hall
Product Specialist, Homeschool Boss
About Theresa
Theresa Redfern-Hall graduated from a women’s liberal arts college in the Midwest. She has a BA in Paralegal Studies and has spent time working on an MA in Library and Information Science at the College of St. Catherine. Over the years, Theresa has worked as a legal assistant in a law office, an advocate for battered women, a court reporter and bailiff for county court judges and a volunteer coordinator for a women’s shelter.
Her homeschooling journey began with the birth of her oldest child in 1995. Since that time, she has been involved in area homeschooling groups, co-ops, study groups as a parent, and worked for several years as an Independent Peabody Tester. In 2008, she began teaching other homeschooled students at area homeschooling co-ops and served as board president of one local co-op.
She has been working with the Homeschool Boss team since 2019.
Dr. Stuart Grauer
Founder and Head of School Emeritus, The Grauer School
About Dr. Grauer
Dr. Stuart Grauer is founder and Head of School Emeritus of The Grauer School in Encinitas, California, has spent more than thirty years asking what happens when schools are designed around human relationships instead of systems, around places instead of programs, and around freedom instead of compliance. He is also founder of the Small Schools Coalition, through which he advises and researches schools around the world, and the author of The Way to Pancho’s Kitchen: A Trail Guide for Small School Leaders (2026). His work explores a simple but urgent question: as education races toward larger systems, artificial intelligence, and immersive digital worlds, what distinctly human experiences become more—not less—essential?…less artificial, more real?
Dr. Grauer is a prolific author and speaker who writes nationwide, monthly columns about naturalist-inspired leadership and small schools education for various sites and has provided keynote addresses for groups worldwide. As Joe Brooks, Executive Director, Community Works Institute, noted, “Stuart Grauer is rapidly becoming one of America’s most important and popular educational story-tellers.”
Chad Kinart
CEO, Homeschool Boss
Chad Kinart is the CEO of HomeschoolBoss, where he leads the company’s work in norm-referenced assessment for K-12 families and educators. His career connects three worlds: sports medicine, assessment, and education technology. That mix gives him a practical view of what it takes to help learners, and the people supporting them, grow stronger.
Chad began his career as a certified athletic trainer (ATC). He later managed the exam-development process used to certify athletic trainers nationwide, working with subject-matter experts, volunteers, and vendors to keep a high-stakes assessment rigorous and fair. That experience grounded him in how good measurement is built and why it matters.
He then moved into K-12 education technology, where he helped schools and districts align instruction and assessment. At Instructure he was a Senior Sales Executive for Academic Benchmarks and earned a place in the 2023 Presidents Club. He later worked with Via TRM. Throughout, he has championed evidence-based decision-making and the idea that data should serve both students and budgets.
Chad holds a Master of Science and an MBA, with graduate study at the University of Nebraska at Omaha. He lives in the Twin Cities, and he describes his approach simply: living his best life one day at a time and working to make the world a better place.
Kathleen Cotter Clayton
VP, RightStart™ Math
Kathleen Cotter Clayton is the daughter of Dr. Joan A. Cotter, author and developer of the RightStart™ Mathematics program. Kathleen is involved with curriculum development and has written or co-authored 18 manuals. She travels, teaches online middle-school classes, and speaks across the US and internationally, sharing the mission to help children understand, apply, and enjoy mathematics.
Kathleen has a Bachelor’s degree from the University of Minnesota and has two Masters Degrees from the University of Mary in Bismarck, North Dakota. In her spare time, Kathleen designs and creates mathematical quilts and loves to travel all around the world.
Oliver Stremple
Founder, Stress Less Bookkeeping
Oliver lives in South Minneapolis in a 114-year-old house with their spouse, two kids under 5, a tiny cat, and an old dog. They have always had an insatiable desire to organize information and ideas. As a homeschooler in rural Wisconsin, they made their first graph to chart how many times their donkey Brighty brayed each day. They have always been involved in social justice and grassroots organizing and this led to a Bachelor’s degree in social work and a career in nonprofit operations.
In 2025, they started Stress Less Bookkeeping to support small business owners and community members who do not love numbers make sense of their financial processes. Being self-employed has been everything they hoped it would be, allowing more time for art, sewing, quilting, native plant gardening, and homeschooling their kids.
Alex Roosenburg
Founder Development Specialist, National Microschooling Center
Alex Roosenburg started her career as a classroom teacher, then a technology coordinator in International Schools. She became a school administrator at the age of 30, and after doing that for a few years, decided to open her own microschool, with a focus on future-ready skills and equitable tuition structures. At the same time, Alex worked as a coach for 4.0 Schools, to help fellow education entrepreneurs build out and pilot their ideas. This led her to meeting Don and Ashley at the National Microschooling Center.
Alex now works as a coach to groups that are starting schools, and as a Founder Development Specialist at the Microschooling Center, helping microschool founders at any stage in their journeys of microschooling.
Michael Wall
Youth Voter Outreach Specialist, Office of Minnesota Secretary of State
Michael is the Youth Outreach Specialist at the Office of Minnesota Secretary of State. He specializes in supporting success and the mission of the client through the building of relationships. He leads the day-to-day operation for various youth voter outreach programs at the Office of Minnesota Secretary of State Steve Simon.
Theresa Redfern-Hall
Product Specialist, Homeschool Boss
Theresa Redfern-Hall graduated from a women’s liberal arts college in the Midwest. She has a BA in Paralegal Studies and has spent time working on an MA in Library and Information Science at the College of St. Catherine. Over the years, Theresa has worked as a legal assistant in a law office, an advocate for battered women, a court reporter and bailiff for county court judges and a volunteer coordinator for a women’s shelter.
Her homeschooling journey began with the birth of her oldest child in 1995. Since that time, she has been involved in area homeschooling groups, co-ops, study groups as a parent, and worked for several years as an Independent Peabody Tester. In 2008, she began teaching other homeschooled students at area homeschooling co-ops and served as board president of one local co-op.
She has been working with the Homeschool Boss team since 2019.
Dr. Stuart Grauer
Founder and Head of School Emeritus, The Grauer School
Dr. Stuart Grauer is founder and Head of School Emeritus of The Grauer School in Encinitas, California, has spent more than thirty years asking what happens when schools are designed around human relationships instead of systems, around places instead of programs, and around freedom instead of compliance. He is also founder of the Small Schools Coalition, through which he advises and researches schools around the world, and the author of The Way to Pancho’s Kitchen: A Trail Guide for Small School Leaders (2026). His work explores a simple but urgent question: as education races toward larger systems, artificial intelligence, and immersive digital worlds, what distinctly human experiences become more—not less—essential?…less artificial, more real?
Dr. Grauer is a prolific author and speaker who writes nationwide, monthly columns about naturalist-inspired leadership and small schools education for various sites and has provided keynote addresses for groups worldwide. As Joe Brooks, Executive Director, Community Works Institute, noted, “Stuart Grauer is rapidly becoming one of America’s most important and popular educational story-tellers.”
Where
Coeur de Catherine
St. Catherine University
2004 Randolph Ave
St Paul, MN 55105
Parking
Parking is free!
The Coeur de Catherine (CdC) building is listed as #3 toward the southwest side of campus. Dew Drop Parking Lot and Library Parking Lot are the closest to the building. Elevators are available.
Entering Campus from Gate 3 (Randolph Ave)
1. Drive straight until you reach a T intersection.
2. Turn right and continue down the hill.
3. The Coeur de Catherine (CdC) will be on your right as you drive down the hill.
4. Parking is available at the bottom of the hill in the Dew Drop and Library lots.
Entering Campus from Gate 4 (Fairview Ave)
1. Drive straight, following the road until you reach a T intersection.
2. Continue straight, going down the hill.
3. The Coeur de Catherine (CdC) will be on your right as you drive down the hill.
4. Parking is available at the bottom of the hill in the Dew Drop and Library lots.
When
September 30, 2026
8:30-5:30PM CST
Register
We can't wait to see you!
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