family + business operations for parent entrepreneurs


We're Kevin + Courtney Gilroy: married best friends turned parent entrepreneurs. is the resource hub + like-minded community we were missing in our first days of new parenthood + business ownership.

Becoming a profitable stay-at-home family changed our life. Now, we help other current + soon-to-be parents have a healthy start to parenthood + entrepreneurship.

Learn more about our systems for running the business of family alongside the family business here or ask us questions here.




The Most Important Question for Parent Entrepreneurs

jenna kutcher yellow shirt blue background

Jenna Kutcher shares her take on parenthood, entrepreneurship + what living organically means to her.

Created by potrace 1.15, written by Peter Selinger 2001-2017
Reading Time: 12 minutes

Parents field questions ALL DAY LONG. From “what’s for dinner?” to “where’s their other shoe!?” to “are we there yet?”

I mean, if you haven’t been asked for a snack in the last 2-hours, are you even really a parent?! 

And for business owners, questions abound all day long, too. From “what’s most important to work on next?” to “is this the best use of our time?” to “is it time to automate or hire?” The list – understandably – goes on.

So it stands to reason that as a parent entrepreneur, you’re fielding your own 6,200 thoughts per day PLUS those outsourced to you as a leader in your home + work.

That’s a lot of questions to answer!

And so, where do you even begin? 

My friend Jenna Kutcher says it’s with ONE simple question that she answers in her new book, “How Are You, Really?

From the book, she writes —

“It’s no surprise we’re exhausted. Before we’re even fully awake, we start scrolling through everyone else’s opinions and ideas and solutions— our news feeds, our Facebook page, our Instagram feeds. We crowdsource our life to push us toward something else, to distract us, to lose those 3 AM thoughts in the comforting chaos of the latest craze. We set goals we think we’re supposed to, we buy the bestselling planner, we create the resolutions that sound nice to (and for) everyone else, and we hope for the promise on Monday that it’ll all be different.” 

I love a good call-out. 

And in today’s episode, I want to introduce you to Jenna because if there’s anyone to give a good call-out, it’s her. And I should know — because she has called me out personally! But, most importantly, she’s highly credentialed in this online business space while living aligned with her family-centered values.

She’s a born-and-raised Minnesota wife, mom of 2 little girls, and an entrepreneur with a 7-figure online course business, while hosting her #1 marketing podcast: The Goal Digger Podcast. She shares the stage with Tony Robbins, Marie Forleo, Ed Mylett, Maria Menounos, Dean Graziosi, Mel Robbins + so many inspiring top-level thought leaders often. And she’s doing so with a baby on her hip.

If you’re a parent entrepreneur desperate for a breath of fresh air + a good friend to grab you by both shoulders + shake you to wake up to your life + start living it, then this conversation with Jenna is for you.

Let’s get into it!


So what’s even more fascinating is if we go before that, I didn’t want to be a mom for a long time. Then, it was on my heart + I really shifted, which was shocking because it’s like, “wow, we can change our minds + grow.” What a beautiful reminder for all of us!

But the first time that we got a positive pregnancy test, I was a full-time wedding photographer so I was in the business of trading time for money. I was also in the business of denying help: help that I desperately needed as an entrepreneur. And I think a lot of people can find themselves that way.

Just like the book feels like my baby, my business was my baby. And it was something that I was white-knuckling because I was so worried to release my grip on that control. I just believed a lot of lies around like “no one can love this the way I do” + “no one can do these things the way I can.” 

So when I got that first positive pregnancy test, I remember we were in Hawaii, at a luau, + I was predicting my due date. And my heart sank because I realized I was going to have to cancel on five brides. I was going to have to give up a significant portion of our income + that was not going to work. How was that going to work? 

And Drew, my husband, is selling wine + he was in his busy season where they have blackouts so he couldn’t take days off. And he thought “maybe I can get a weekend off” but that was not what we wanted!

We pictured being in nature with our kids or being at home + reading stories. Now, all of a sudden, we were thinking about entering parenthood in this way that felt so frantic + suffocating. 

And so it was just fascinating with our experience because we went through two losses + it took us three years to meet our daughter. 

But the greatest lesson that I couldn’t see when I was in the situation that was so dark + heavy was that the waiting season was just as important as that which we were waiting for — our sweet little daughter + these Saturday mornings having pancakes as a family.

And so it was just a really big wake-up call for us. A lot of times I think those waiting seasons can get wasted because we are so stuck in that grief or “the almost”, but, for us, it was this time where we were just intentionally releasing the grip, letting go of that white-knuckle life so that we could figure out how to free up our time, which is our currency.

And that’s how we want to spend our lives with our kids. 

A lot of people can relate to seeing that their lives aren’t lining up logistically with what they’re dreaming + waiting for, being frustrated in the waiting + just wanting to get to that finish line + something ultimately has to give.
That often begins with the permission to ask for something more, which is often easier said than done. So tell us about that: the permission to ask for more that you gave yourself. 

It’s so interesting because when we are ambitious women, a lot of times we lean on tools to hold ourselves back. And what I mean by that is we lean on things like gratitude, which is one of the most beautiful practices a person can adopt, but while gratitude can keep us feeling grateful, it can also keep us feeling stuck.

And what I mean by this is that if we’re having something that feels off, or if we’re in a place in our life that we’re struggling, we often share that struggle with apology + then have all the caveats of “but I’m so lucky because I have a 401k” or “I’m so lucky because I have healthy kids”.

I think we all need relationships where we don’t have to throw in the caveats – where people know + understand that there is privilege, gratitude + all these beautiful things. But also when we feel that nudge or that ping that there might be something different or there might be something more a lot of times, it’s easier to ignore it.

Because the second we acknowledge it, the second that we recognize it + even speak it into existence means that we need to do something about it. And I think a lot of us are afraid to even whisper those like deeper desires because we think “well, crap. Now I need to go out + do something.”

And I think that’s where a lot of people are finding themselves right now. 

not only are you now called to do something, but You’ve acknowledged that there’s something more to do but it’s for yourself + that can feel selfish.
SPEAKING TO THIS AUDIENCE OF PARENTS, How do you reconcile with the initial pang of guilt that can come with looking at growth?

I have it all the time + I hope we can reconcile it, but I also remind myself there’s this part in the book where I talk about integration + blend because a lot of times when I have mom guilt is when I’m not incorporating my children into the work, or I’m not even allowing them to see what is happening.

This morning, Coco was up in the middle of the night for two hours. I told her “baby, mom has got to go to bed. Mama gets to talk to people tomorrow” + she asked “talk about what?”

I was inviting her to understand my humanness + my human nature, but also my intention + inspiration. And so now, it’s such a fascinating thing having a toddler that understands more because I get to invite her into this work, whether it’s sitting next to me during a team call, attending an event with me + watching me on stage, or just literally watching Baby Shark while I was writing my book in the corner of my screen.

It is fascinating because I think the guilt comes in when we try to separate things + try to live with our life in boxes, because it’s not meant to be that. 

Even when it comes to my marriage with Drew, if there’s something that’s going to take me away from my family, I consider how I can either incorporate them into it or communicate why this is so important to me + help them buy into the vision. That shared vision is everything.

I think guilt comes in when you’re the one carrying the torch + lighting the path on the same way.

We shoot ourselves in the foot when we make it our sole responsibility to execute this vision. You being the CEO does not mean you’re solo. You might start your business solo, but when it comes to the family angle, you’re not solo.
What does your family operating system look like behind the scenes? Tell us details of what happens in a day or a week.

Last Sunday night, Drew + I were getting ready for bed. We sat down at the kitchen island + I walked him through my schedule in the coming week because he’s a stay at home dad + I’m still nursing our little one. He’s doing school drop off, pick up + all of those things so we really do have to be like a tag team. I sat him down + told him “I need your full attention. We’re going to walk through this together.”

We do a lot of family planning meetings like that. We also do a lot of habit tracking in my family. And it’s just something that I’ve really adopted recently, especially with the book coming out. I want to be energized, not just in my work, but in my family life. That requires things like taking care of myself, taking my vitamins, working out, all of these things. 

Having a visual guide for us has been really helpful in keeping track of what we want to do on a daily or weekly basis + figure out how we can do it together or how I can take the time that I need to in order to get things done.

[Related: The Value of the Digital Family Calendar]

I envision that once our kids are a little bit older, we’ll be having family meetings once a week where we walk through this schedule + we tag-team things. I just feel like when everyone is on the same page, it makes such a difference. 

Coco is a very deep feeler as a child, like an actual deep feeler, so her knowing what to expect + her understanding what happens next has been really big for her feeling safe + secure in our day-to-day life. 

It’s also been a really great thing for us as parents to really acknowledge + it actually does feel good to know what’s happening next. We’re always learning from our children.

You look totally different than where you are now today with two kids + a thriving marriage compared to when you were just starting your business. The Jenna Kutcher in front of us now “has it all” — you’re a supported family-centered CEO. 
How do you operate your family + business at the same time without sacrificing or feeling like you’re sacrificing one or the other? 

That is such a beautiful question because I feel like for so long we’ve been striving for balance but I think balance is the wrong thing to pursue because if you think about it, balance is like a moment. It’s not something that you can continue to maintain. We can achieve balance but you can hit it for just a second + then you’re off again. And you’re only going to beat yourself up. 

For me, it’s all about leaning into my values + for a long time, one of the reasons why I didn’t write a book was because I believed it was going to take time away from my life. So I had to create pockets of time to make this a worthy spend of it. 

I look at time as my currency so how I am spending my days is how I’m spending my life. And I want to spend my life engaged with the people that I love so with the book, a lot of the values I had to rearrange were things that were traditionally done.

They wanted me to travel to do my audio book but I told myself “I’m going to figure out a way to do this from home.” So I called our local radio station + recorded in a sound booth with my cousin who’s a DJ who did my audio engineering so that I could be home with my kids. 

I had to do a photo shoot + they wanted me to go to a studio so I asked “is there a way we can figure out how to do this from home so that I can be with my children + they can be a part of this instead of me going off + doing my work?”

We recently went on a trip + brought the kids along + it was honestly one of the best vacations, even though I was working. For me, it’s about figuring out how we can incorporate work in a way that doesn’t take me out of my life, but keeps me in the life that I want while doing the work that I love.

And that’s been a challenge but I’ve got to step up to the plate because if I’m going to talk about these things, I gotta be living them. And I am such an alignment freak — I will not say one thing + do another so it’s been such a good challenge for me to really think outside of the box + propose different ways of doing things that maybe traditionally haven’t been done that way, but that can invite in a whole extra aspect.

And I can tell you that you can hear the happiness in my voice or see it in my face in those instances that I do that because I am living in alignment. 

What does living organically mean to you? 

It means living a life that feels good — one that’s not for “looking good”. If we think about organic food, all the food looks the same on the outside, right? You can’t tell the difference between an organic apple + a non-organic apple. However, it’s going to make you feel different, right?

[Related: 001. Establishing Family Values by Living Organically]

So often, success is pointed at the things that look shiny. It’s those vision boards, Pinterest pins, the Instagram posts. But to me, success is a feeling. Coco often catches me crying happy tears + she just smiles because I’m living my dream.

And it’s not the kind of dream that I’m going to look back 10 years from now + feel regretful for having missed. I’m so awake to it that it feels so good. 

That’s what I want people to do — to redefine success. “Having it all” involves deciding what “it all” is because our life is actually really simple when we boil it down but it feels so good.

And because it feels good to me, that’s like having it all. 

Jenna, you are the ultimate OrganicFamilyCEO. I could not be more excited to celebrate the inevitable success that this book will be + the impact that it’s going to have. What a change maker. Thank you for sharing your personal behind the scenes with us.

Courtney, thank you so much for letting me be your first guest! I feel so honored + thank you for doing the work that you do. Your audience is so blessed to have you. 

I wish that a decade ago, people were talking about these topics because I think it would have saved me a lot of heartbreak. It probably would’ve saved me a lot of chapters of that book. 

But at the same point too, I’m just grateful that this is something that is being shared about, because I think that more people want it all, but they don’t even know what that could look like. The work that you do really matters + I’m just so grateful to have been a part of it.