This episode? I’m obsessed.

Kelsey Cook is a certified teacher, entrepreneur, and mom of four who built a nationwide subscription box business that now ships over 14,000 boxes a month. And she started it while raising her kids and running a preschool... all during nap time.

In this episode, we talk about what it really looks like to start a business as a stay-at-home mom, how to grow something meaningful without burning out, and why starting small is sometimes the smartest strategy of all.

Here’s what you’ll hear:

• How a few preschool packets on her porch turned into a full-blown subscription box business
• What made her say yes to launching before she felt “ready”
• How she balanced building a brand while raising four young kids
• The real reason parents love her boxes (hint: it’s not just the activities)
• The mindset shifts that helped her stop overthinking and start scaling

This is the episode for every mom sitting on a business idea but feeling like there’s no time, no space, and no way to make it happen. Kelsey proves it’s possible to build a business that works with motherhood, not against it.

🎁 Exclusive Listener Discount:

Use code SYDNEY15 for 15% off a box! Grab yours here → https://rstr.co/learning-with-kelsey/3471

If you’re looking for an easy way to support early childhood learning at home without adding more to your plate, these boxes are gold. No prep. No stress. No last-minute craft supply runs.

✨ Connect with Kelsey:

Instagram → @learningwithkelsey

Website → https://learningwithkelsey.com

Subscribe to Mompreneur Mastery for real conversations, smart strategy, and stories from other mompreneurs who are growing their business in the margins of their day. Because success doesn’t have to mean doing more. It just has to work for you.

This episode contains affiliate links. That means I may earn a small commission if you purchase through the link, at no extra cost to you. I only share products and businesses I truly love and trust.

Mentioned in this episode:

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Join Plan it, Post It, Profit and plan a month of Instagram posts that lead to sales in just 5 days!

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Foreign.

Have the absolute pleasure of being able to talk to Kelsey Cook.

And this might be one of my favorite episodes ever.

So Kelsey is a certified teacher, an entrepreneur, and a mom of four.

And she's on a mission to make early learning easier and way more fun for parents everywhere.

After six years in the classroom and a degree in early childhood and elementary education, she traded lesson plans for packing tape and launched Learning with Kelsey, a subscription box that turns turns everyday moments into hands on learning adventures for little ones.

What started as a passion project in her living room during COVID is now a go to resource for families across all 50 states where she helps parents ditch the overwhelm and spark curiosity, connection and confidence with their kids.

And her story is so amazing and I know you're gonna love it.

So let's dive in.

Welcome to mompreneur Mastery, where we build businesses, raise families, and skip the hustle.

That doesn't actually help.

I'm Syd o', Brien, certified Instagram strategist, mom of three and your no Fluff guide to making more sales with content that's strategic, simple, and you can actually make in the small mom cracks of your day because Instagram shouldn't feel like a full time job you're not getting paid for.

If you're ready to stop posting just to stay visible and start sharing content that actually converts to sales and gets you clients, you're in the right place.

All right, now, before we get into your business, Kelsey, can you tell us a little bit about how your business got started?

Yeah.

So I was a teacher.

I taught third grade and then I taught kindergarten.

And then when I had my first baby, I decided to stay home because it was so hard to do teaching and have a baby.

It was so crazy.

And so I stayed home and then I missed teaching so much and so I was like, okay, what can I do that would still do teaching but be able to be home?

And so I started a preschool out of my home and I taught preschool for four years and it was so fun.

It was like the perfect mix.

It was two hours, twice a week.

I had two kids at the time that I was doing it, and my older son got to be in.

It was so fun.

And then Covid happened and so I had to close preschool.

And after closing preschool, I was like, okay, these little kids are at home.

I miss them.

We did so many fun things at the end of the year.

What can I do?

So I started putting together little packets for them of things that we would have done in preschool and leaving them on the porch for their moms.

And so the moms would come get em and do them.

And they started sharing about em on Instagram.

And so I was like, okay.

More people were kind of reaching out to me in my neighborhood, just saying, oh, can I get one of those?

Because, like, we don't know what to do with our kids.

And I was like, okay, well, maybe I could sell these.

So I started selling them for like $15 a packet, I think is what I did.

And I made an Instagram because I was like, okay, I'm going to kind of talk about these somewhere.

And more people in other states wanted them.

So I was mailing packets and I kind of was like, okay, I feel like this is an actual thing more than just like this pandemic need.

Like, people are loving being able to do activities.

And kind of as a teacher and mom, I had this unique perspective that not everyone has.

And so I was like, okay, I'm going to go all in.

I sent.

I, at the time had done like 50 packets.

And so I'm like, okay, I'm gonna do a box.

I'm gonna put it in a box.

It's easier to send.

Cause I was mailing them in envelopes.

And that's how it started.

And then we've just gone from there and it's just been crazy.

That's so cool.

That's like quite the origin story.

Like, you're like, say it quick.

And I'm like, well, it's kind of long.

Totally fine.

Like, it needs to be that long to go from the beginning to the end.

It's like, yeah.

Wow, that's incredible.

It's so fun.

Yeah.

Pandemic.

There were definitely some.

Some big negatives there, but the creativity is like, kind of interesting to see at the same time, like, how people worked with it.

And like, yeah, so that was a really cool story.

And then how long was it from like, when you started leaving packets on your porch to when you had like, like mailing boxes and like a more subscription type of thing?

So like, just a few months.

But when I really made like, what I have now, which is 20 activities in a box, was about a year later.

And yeah, so since then we've grown.

I sent 14,000 boxes last month.

So it's just been insanity.

Yeah, I can imagine.

What was the moment where you were like, oh, my gosh, I have to.

I have to like, do More and make this a legit business.

So I actually, I had a friend of a friend, actually that was owned a business.

She owned a really cool, like, kid sock company.

And she reached out to me and was like, hey, can we go to dinner?

Like, I think you have a really good idea here.

And so I went out to dinner with her and this was like in the summer when I was still doing packets.

And she's like, I think this could be a business and I think you should just go for it.

And I didn't really know her that well.

That's not something that I would have ever, like, done.

I kind of was like, I don't know how to do a business.

And she's like, you can do it, so just do it.

I think this is a good idea and you should just do it.

And I was like, okay, I'm just going to do it.

That's awesome.

Yeah.

Sorry.

I was kind of thrown by my kid coming in.

That's literally the story of my life.

I'm like, I.

So I have four kids now.

So I'm like, I've built this business with babies on my lap, feeding babies, pregnant.

So my kids are always coming into every meeting that I have.

All the time.

All the time.

It's the best.

How old are your kids now?

So I have 9, 7, 4, and then 18 months.

Oh my goodness.

Wow.

Yeah.

Yeah.

I hope I only have three, but they're also like closer in age.

Mine are, yeah, seven, six and four.

Oh, my gosh.

Yeah.

So, yeah, I, I can, I can understand the chaos part of it for sure.

Yeah.

And I do feel like my third.

That was like my hardest transition was having a third baby.

Because I'm like, it was a crazy.

All of a sudden you feel like there's so.

And yours, like, are the same.

Mine, I had five, three, and then a newborn.

And so it's like everybody's at home, nobody's at school yet.

And it was just chaos.

So adding a fourth was like, oh, my gosh, we already have chaos.

So it's easy.

Yeah.

That's interesting.

I would think four.

I would just be like, no, I can't.

Adding another one.

Really?

I'm like, I know, like, what already.

Is going on here, which is a lot.

Adding one more just like, what's one more?

Yeah.

And you're like, the older ones are kind of more self sufficient, you know, they could do more things, which is nice.

Yeah.

How hard was it to like build and grow that business with young kids out?

It was so hard.

I'M like, I did, I did a lot during nap and bedtime because, you know, I was like, I quit teaching because I wanted to be home.

So I'm like, I now don't want to, like, be working 247 because I love being a mom.

That's like my number one priority.

So I. I would do it during nap and bedtime.

And then that became like, crazy because I felt like I was never off, you know, like, I would stay up so late, I would never have a second where I wasn't being either mom or business.

Right.

So it was really hard.

But my husband is like my number one supporter, my number one teammate, and he kind of was always saying to me, like, if it's too much, like, hire it out.

Like, you can do this, this, this, and then let other people do something else.

And so that was hard for me because it was like my baby, you know, and like saying, okay, now someone else do this part of it.

But that was like my biggest reason for success, I think, is that I was able to bring on a team of people that have been so helpful to me and have helped me grow and learn.

And yeah, my husband actually quit his job in December and is working full time with me now, which is so much better.

I'm like, I love that.

That's way better to have.

Have him doing so many things with me because it was, you know, for a while it was like, okay, he's doing his full time job.

I can't, I can't expect him to help me.

And he would help me when he got home, but then it was just chaos.

So that's been really, really great.

That's so cool.

I love that you're able to outsource like that.

I.

It's so important to be able to delegate.

Even like in just parenting, like, you can't do it all on your own.

You got to have that village.

So it makes sense.

Like, you need that in business too, for that success without completely, like, burning out.

It's so stressful.

Yeah.

And I think, like, the more that I've talked about business and like, I always thought, like, okay, I'm not a business person.

Like, I don't know business.

I'm not.

It's so hard for me to even consider myself an entrepreneur because I'm like, I'm a teacher, I'm a mom.

It's so, it's so foreign to me.

But the more I talk about it, the more I'm like, there's so many similarities between being a mom and being an Entrepreneur and so many things that, so many skills that we learn as moms that translate exactly over into business.

For me, like I, I've learned, like you said, delegating like a village is so important.

And I've learned that in my kids lives, having a coach or a teacher or someone else talk to them and share advice with them and give them something I can't is so powerful.

Just like me reaching out to someone maybe that is really great at marketing or really great in another area that I'm not.

It's such a value to my team too.

Yeah, absolutely.

And I think, I think the biggest skills that translate are time management and like flexibility.

Like.

Yeah, those are so important when you're a business owner.

Yeah.

And as a mom, you know, you learn, you fit things in everywhere.

So we're the ultimate multitaskers.

Yeah, absolutely.

Like, I feel like the most common one at my house is like my kids get really into certain kinds of foods or snacks and if we run out or like it's gone bad or something, you always gotta have a backup plan.

It's like that in business too.

You gotta just be able to roll with it and like just keep going, adapt and move on.

Yeah.

And I'm.

And I feel like, like when you become a mom, you're like, oh, I know what I'm gonna do.

And then you find out.

Okay.

There's so many things I don't know.

Yeah.

And that's the same with business.

I'm like there every day.

I'm like, oh, new issue that I had no idea that even existed.

But you're right.

Yeah.

Yeah.

The same thing like every.

I feel everyone's a perfect parent until they're a parent.

And then everyone's a perfect business owner.

Until they're a business.

Exactly, Exactly.

Oh my gosh.

So what about your boxes?

Makes them so unique and makes everyone love them.

Do you think so?

I, I'm really passionate about early childhood education, but also about parent involvement and parent connection.

Because I think that is the best thing that you can do for your kid is foster this great relationship in those early years.

So my boxes are more than just like, you're giving your child something to do with them.

It's something that moms or dads or whoever's doing with them is sitting down and doing with them.

So it's more about the connection point that you're getting 10 to 15 minutes a day where you're getting to do an activity with them.

You're all involved with them, you're making them Your focus of their, your attention.

And I think that is where like the magic happens with my boxes.

They're fun activities.

I love the activities.

Obviously I'm excited about them.

But at the end of the day I think like the parent connection is like the most special part about it.

That'S so, so important.

And I feel especially for mom business owners where it's very easy for us to get bogged down in like the constantly going between like work and business.

And like you always have these things on the back of your mind where it's very hard to be like present and in the moment.

So having like the pre, like determined activity like all laid out where you can have that connection you need, but it's also not something you have to like come up with on your own because you just don't have the brain space for it would be like incredibly helpful.

Yeah, it's so nice because even I kind of found that even as a teacher, as someone that's done so many activities in my time, like with a two year old, sometimes I was like, okay, what do I do?

And I'm like, well, I can look this up, I can find.

But then, then by that point it's gone.

You know, your moment of teaching or connecting is gone.

Yeah.

And then it's like, well, I have to get like these supplies for it and like run to the store for this.

Like.

Yeah.

Yes.

So they come with everything that you need to do the activities and like in the perfect amount.

Because I also found if you want to use pom poms, like you have to order a thousand off Amazon.

And nobody wants a thousand pom poms at their house.

No, no one wants that.

We did that like one time and my kids started eating them and I was like, we're done.

This is a problem.

I can't.

It was like finding them on the couch for weeks.

Oh my gosh.

Yes.

Yes.

It's too much.

It's chaos.

That's so funny.

And now we are a homeschool family and my kids were.

Well, my youngest is at that age where a lot of the learning we do is done through play.

Because it's not like a four year old's going to like sit and listen to me like yap about history or something.

Yeah, for sure.

Is there like, are there more educational components in your boxes?

Yeah.

So we have different boxes.

We have four, five different ones.

So I do them by age because another thing that I found was like I would see activities that were for a 2 to 4 year old and I'm thinking, okay, there's no way it's for a two and a four year old.

Those are so, so different.

So different.

Sounds like they would be similar, but.

No, no, they're not even close.

And even I would say like teaching preschool, I'm like, I can tell a spring birthday from a fall birthday kid, you know, even like those six months make a huge difference.

So I have a toddler box, a preschool and a kinder prep for our activities.

So they're very geared to their ages.

So like for the four year old box, they're working on fine motor skills, but they're also working on introducing letters, tracing letters, scissor skills, like simple things like that, color matching, counting.

But they're doing it in a fun way.

So like for instance, in this last box, it was the May box is all about flowers and gardens and they had flowers with a pipe cleaner with a number on them and they were threading beads onto the pipe cleaner.

So they're getting to, it's fun, it's exciting for them.

But then they're also getting to count.

They're getting to practice fine motor.

They're getting to practice even like number order.

So there's so many different little things that they're working on.

That's so nice.

And then like, yeah, the more fun it is, the more likely they'll actually like do it and learn from it too.

Oh yeah, yeah, you gotta have it.

I love themes and I think that's the teacher in me that loves a good theme.

So every box is themed monthly and everything is around that theme.

So like our June boxes, oceans.

And so there's so many fun things that they're getting to do with ocean animals, with seaweed, like all these different things.

I love that so much.

Like, yeah, I know my kids when we do like little mini unit studies and everything is around a theme, they, it's like when they're most engaged for sure.

Yes.

It's so funny.

But I'm like, I, I love a holiday, so I get it.

Yeah, same.

What was something you wish more moms knew about starting a business with kids at home?

I think I wish more moms would just go for it.

That's kind of what I've learned is I just put things out without like second guessing it, which is not really my personality.

So it's so funny that I've been able to do that in business.

But I think because I felt so excited about it and I loved it so much that I was just like, I'm just gonna do it I'm not doing this with the purpose of this is gonna be a huge business.

This is gonna be whatever.

And so I was like, I'm just going to make a logo on Canva.

I'm just going to throw Google how to do a website and just try it.

Because you can always change things.

You can always perfect things.

You can always make them better.

But I think, like, that first step of just doing it is the best way to get it out there.

So don't wait till you have the perfect name.

Don't wait till you have the perfect logo.

Just put it out there and then see where it goes.

That is such great advice.

And I feel like the.

Not for, like, my whole business, but, like, for different offers, specifically.

The more I come up with something and am excited about it and, like, put it out there before it might not super be ready.

But, like, we can tweak it along the way.

That, like, man.

And is, like, catching and is, like, great for marketing and attracting new people.

And you're so excited about it because you know how good it is.

And you are normally like, your own ideal client or customer.

So, like, they need it too.

So, yeah, definitely jump in.

It's not.

It's not about being perfect.

Yeah.

Cause it can get hard.

And especially, like, you're taking in other people's opinions or, you know, like, you kind of have to just, like, tune it out and just say, like, I like this.

I'm gonna do it.

Yeah.

And I feel like the more, like, outside opinions I get, the more bogged down I get.

And I'm like, is this a good idea?

Should I do this?

Should I scrap it?

Should I change this or that?

And I'm like, no, just a hundred percent.

Just because the opinions you really need are yourself.

From having to do the work and making sure it fits within your life.

And also the people buying it because you want them to, like, benefit from it, obviously.

But, like, there's a lot of outside noise a lot of the time from random people.

And I'm like, sometimes that's very valuable.

Sometimes.

Yes, it's not.

Yep.

You have to, like, take what works for you and then leave what doesn't.

Yeah.

And if it.

You try it and you know it doesn't work, don't feel bad about leaving it, no matter who it's coming from, because you know, you know your own experiences best.

For sure.

Mm.

And I think that's another thing where motherhood has really helped me.

I think that I've gained so much confidence in becoming a mom.

And, and growing with my kids, and that's helped me to be more confident in business.

Like, you know, when you have a kid, you have to.

You're their number one advocate and you have to be the one to say things.

And you can't, you can't second guess every single time.

You just have to be confident that you know what you're doing.

And I think that has helped translate over into business so much for me.

Yeah.

Now that you mentioned it, I'm like, huh, yeah, me too.

I can definitely see that.

The, that advocacy, like before kids, I was like, very.

I don't know if I want to stick up for myself.

I'll just like, you know, be a people pleaser and go along with this.

But now I'm like, exactly.

I can't.

I don't have.

I can't do that.

That doesn't work for me.

I'm not going to pretend it does.

Yeah.

And that's.

I.

Exactly the same.

I feel like I grew up, I've been a people pleaser for my whole life like that.

So jumping into being a mom, it was so much, so hard for me to be like, okay, I'm the one that has to say, it doesn't matter what this person's saying.

It doesn't matter what this person's saying.

And it's definitely taken practice.

But the more kids that I've had and the older my kids have gotten, I've gotten so much better at it.

And so in business, same thing.

Look, I've.

There's been hard conversations I've had to have that have been tricky or like, difficult for me to do, but the more that I do it, the better I get at it.

Yeah, for sure.

It's definitely a skill and it's not super fun to learn, especially when you are a mom and you're just kind of like thrown into it like there's no course or anything, but the more.

You do, the easier.

Just go for it.

For sure.

Yeah.

Yep.

For sure.

Fake it till you make it.

Yeah.

Yeah.

What is of advice you would give to a mom who has maybe like an idea, but zero time or energy to pursue it?

I would say start small, you know, so if you.

Even if it's like you're just sharing about your idea, you're maybe not offering it for sale or whatever, but I think just do something small that gets you in a step in the right direction and then you can build on it.

It doesn't matter how long it takes.

You know, you.

Some people take some five years to do something.

Some people take some a week, like just do a little and then that will kind of help you to see what can I give to it, what can I not?

And in the end, you're the ultimate decider.

You know, that's what's so cool about being an entrepreneur is you get to decide what your time is.

You get to decide what's most important.

And so I think just doing a little bit is like the best first step.

Absolutely.

That's such great advice.

And I feel like that also relates to parenting.

Like, different kids are sometimes on different timelines if there's.

They have different needs or need different supports.

So not comparing yourself and you're like, what other people are doing, because it's not fair to anyone to compare like your chapter one or chapter two to their, like chapter 11 over here.

Oh, yeah.

And it's like, you know, I'm thinking like, okay, it took me four years to even take.

Take money for my business.

You know, I put everything back into it.

So it's like, yeah, it looks fun now, but like, I was working for free for a very long time.

Yeah, it takes a lot to get to that point.

Yeah, yeah, yeah.

How did being a mom of four influence the way you built your business?

So I think that it helped me in how I was going to build my team.

You know, I brought on, basically I started by bringing on all moms, which has been really cool, but it helped me to see, like, hey, this is what's most important.

I knew that being a mom, being in present with my kids was my most important thing.

And so I built everything else around that, you know, so I knew these are the times that I'm not gonna be available.

These are the things that I'm not gonna do.

And setting that tone at the very beginning really helped us as we kept going.

And so, like right now, my warehouse, I have 20 women that work there and they drop their kids off at school and they come and they work at our warehouse until 2 o' clock, and then they go pick their kids up.

And it's like, that has always been something that was really important for me is that the moms were able to give back to their families while also getting to be moms and getting to be home, which was important to them too.

So I feel like that has influenced how I built my business, who I've brought on my team and all that.

That's amazing.

I love that so much.

Like, not only for like you and your business, but also helping other moms as well.

Like, I love working with other moms because they just get it.

Like, my youngest came in a couple of minutes ago, just handed me a snack to open, and then started chanting Odd Squad.

Cause that's what they're watching right now.

I bribed them with PBS kids to be able to do this.

I love it.

And, yeah, like, you didn't even bat an eye.

It's just, like, whatever.

It happens.

Yep.

It doesn't matter.

Yeah.

But being able to help other moms do that too and be more aware of their, like, needs and schedules so they can achieve that as well is, like, really amazing.

Yeah, it's been really cool.

And.

And also, you know, like, moms are so scrappy.

Like, we learned so many different things.

I feel like I've learned.

I've gotten so many great ideas from my.

The moms on my team.

I've gotten so many great, like, tips.

It's just been really incredible.

Yeah.

I started my business as, like, a social media manager, and then I did it while my husband was deployed, and it was, like, the worst timing in the world.

But, like, bad idea, but fun.

Yeah, exactly.

And then I was like, wait, I want other moms to be able to do this too.

So I, like, switched to working just, like, marketing just for moms, for, like, very similar reasons.

So, yeah, moms need the help, so I'm glad we were able to.

To do that.

Yeah.

I love it.

It's fun.

And it's.

You know, we have a couple boys down there now, so we don't discriminate against our boys, but we need.

We need them.

We definitely need them to lift all the things.

Yeah.

Can definitely understand that.

And can you tell us more about how people can get your boxes?

Yeah.

So you can follow me on Instagram at Learning with Kelsey.

And then I have a website, learningwithkelsea.com so you can order the boxes there.

And then I just share tips and previews on my Instagram, too.

Perfect.

Yeah.

And I've been following you, and I love your content.

Thank you very much for that.

Oh, good.

Thank you.

You know, content's hard.

It is.

It is tricky.

I will also share all of those links in the show notes so people can connect with you and try out your boxes so they can connect with their kids in a way that doesn't take up a lot of their extra brain space, because I know my listeners don't have any of that to spare.

Yeah.

But thank you so much for coming on and chatting.

I love you so much.

Yes, thank you.

Thank you for having me.

It was so fun.

So you can very easily see why this is one of my favorite interviews I've ever gotten to do.

Kelsey has such a great story and I got so much from having this conversation with her about business and not comparing myself to others and doing what works for you and sometimes taking that imperfect, messy action can lead to really amazing results when you put in the hard work.

So I hope you got a lot out of this episode as well.

And I also want to share that Kelsey also hooked us up with something really special.

If you want to grab some of her learning with Kelsey boxes, she's giving us 15% off, so definitely check out the link in the show notes for that.

I know I will be grabbing some for my youngest because as a homeschooling parent I know that the best learning happens through play.

So I'm really excited to be able to do that with him and foster that connection in a way that I don't have to plan or go run to the store to buy all the supplies and end up with a million extra pom poms.

So connect with Kelsey at the links in the show notes and I can't wait to be back in your earbuds next week.

Thanks so much for hanging out with me on mompreneur Mastery.

If this episode gave you more clarity or a little boost of confidence, I would love for you to follow the show, leave a review, or share it with a fellow mom building her business on her own terms.

And hey, if something really clicked DM me on Instagram I am ocially yours strategist and tell me the one thing you're doing differently.

After listening, I love hearing what is landing for you.

Until next time, here is to less stress, more sales, and a business that actually fits your life.