Ep 96: How a Mom of 4 Built a Nationwide Business During Nap Time with Kelsey Cook

Written By Sydney OBrien

How One Mom Built a Nationally Loved Business During Nap Time: An Interview with Kelsey Cook

If you've ever found yourself Googling "easy activities for toddlers" with one hand while microwaving chicken nuggets with the other, you're going to love this story.

I recently sat down with Kelsey Cook, a certified teacher, entrepreneur, and mom of four, and it might be one of my favorite interviews ever. Kelsey is the founder of Learning with Kelsey, a subscription box company that helps parents engage their little ones in meaningful, hands-on learning without the stress, mess, or mental load of planning it all yourself.

From Teacher to Porch Drop-Offs

Kelsey spent six years in the classroom teaching third grade and kindergarten before making the decision to stay home with her first baby. Like so many moms, she wanted to be present for her children, but she missed teaching. That led her to start a small preschool out of her home, a perfect mix of mom life and teacher life.

Then COVID hit. With schools and her preschool closed, Kelsey started putting together learning packets for her students and dropping them off on porches. Moms loved them. Word spread. And suddenly she had people in other states DMing her, asking for their own packets.

When Passion Turns into a Business

That porch project grew into a full-blown business. She started mailing out packets, created an Instagram page, and within months, transitioned to mailing curated boxes. But it wasn’t until a conversation with another mompreneur who told her to "just go for it" that Kelsey decided to take the leap.

Since then, Learning with Kelsey has grown into a nationally recognized brand shipping over 14,000 boxes a month. And the most impressive part? Kelsey has built the business entirely around her role as a mom.

Built by a Mom, for Moms

Every decision Kelsey made, how she scheduled her work, what she delegated, who she hired, was based on what worked for her family first. She worked during nap times and late nights, relied on her husband (who eventually joined the business full-time), and built a team of fellow moms who now help pack and ship boxes during school hours.

Her story isn’t just inspiring. It’s relatable. The chaos, the boundaries, the flexible routines, and the stubborn refusal to burn out. Kelsey shares how she let go of perfectionism and started taking messy, imperfect action to bring her ideas to life.

Why Parents Love the Boxes

Each Learning with Kelsey box is more than just a stack of activities. It's:

  • Hands-on learning, zero prep: Everything comes ready to go with exactly what you need (no late-night Amazon orders or buying 1,000 pompoms).

  • Connection-centered: The boxes are designed to help parents connect with their kids for 10–15 minutes a day through meaningful play.

  • Age-specific: Boxes are tailored to toddlers, preschoolers, or kinder-prep kids, with themes that make learning fun and engaging.

Whether you're homeschooling, working full-time, or just trying to make it through the week with your sanity intact, these boxes meet you where you are and help you feel like you’ve got this.

Advice for Mompreneurs

One of my favorite parts of the interview was hearing Kelsey talk about starting before she was ready. She didn’t wait for the perfect name or website. She just created a logo on Canva and figured it out as she went. Her advice?

"Start small. Take one step. You don’t need to know everything right away. Just get it out there."

She also touched on how motherhood has helped her become a more confident business owner. The same instincts that help you advocate for your kids? They help you advocate for your business too.

Want to Try a Box?

Kelsey was kind enough to offer 15% off for our listeners and readers, use SYDNEY15 code for 15% off a box. You can grab your own Learning with Kelsey box at the link below:

https://rstr.co/learning-with-kelsey/3471

Whether you’re looking for an easier way to support early learning or just want to create more intentional moments with your child, these boxes are a total win.

Connect with Kelsey

This episode reminded me that the best businesses aren’t built overnight and they don’t have to be built perfectly either. They’re built one idea, one box, one nap time at a time.

If you’re a mom with a dream and a toddler on your lap, let this be your nudge: it’s okay to start small.

And if you loved this interview, don’t forget to subscribe to Mompreneur Mastery for more real conversations, helpful strategies, and business tips that actually fit your life.

This post contains affiliate links, which means I may earn a small commission if you choose to make a purchase. I only share products and businesses I genuinely love and trust.

Sydney OBrien
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Ep 95: The Branding Shift To Take Your Offer from Meh to Must-Have with Aiza Cheung