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.




What Being the CEO of My Pregnancy Did for My Motherhood

We’re sharing how we arrived at the decision to have a home birth + ultimately what that did for us as parent entrepreneurs.

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Hi OrganicFamilyCEOs! This is Courtney. Today, I’m sharing how Kevin + I arrived at the decision to take charge of our pregnancy + ultimately what that did for me as a mom entrepreneur.

We have had two (yes, 2!) incredible home births to welcome our children into the world + the decision to have those births was one of many we made that we feel set us up for success in parenthood. Our hope is that your empowered decision-making around pregnancy translates positively to your business, too.

Let’s go!

When I was a child, I decided to become a doctor. I absolutely loved the idea of helping families -specifically women + babies - to live their healthiest life possible. 

And when I wasn’t caring for my younger siblings, or starting my first business babysitting in the neighborhood + then ultimately concierge nannying at the Ritz, I was studying to become a doctor. 

I got into Boston University (Go Terriers!), studied with the best of the best + I was succeeding on the outside. I was also, however, feeling emotionally spent + energetically drained the entire time on the inside. 

It was like something in my body was rejecting the experience.

I was brilliant, motivated + doing “all of the things” I was supposed to be doing, + yet something felt… off.

But I stuffed that down — way freaking down. I was Courtney the rule-follower, the one who dependably read the textbooks + checked all the boxes + got the A+ approval.

Now, when the time came to make my ultimate career decision — to decide to step into actual medical school — I had been working for some of the top medical researchers in the world. And during that experience, I had the privilege of sitting in these behind-the-scenes, closed-door meetings with other top medical researchers, doctors + practitioners.

I’ve seen some “ish” in these think tanks (+ I’ve heard even more). I couldn’t be more grateful for those experiences because they saved me from what could have been a drastically different experience in the conventional medical world, that unfortunately, many birthing families experience. 

What I Learned in Pursuit of Becoming a Doctor

Conventional medical intervention is one of the unnecessary interventions that can lead to adverse birth outcomes.

These adverse outcomes could have been avoided had both the birthing families + medical professionals been empowered with the information they need to make individualized, well-rounded informed decisions as a team for each particular birth.

What I learned from that highly unique experience is that so much of the conventional healthcare system is BROKEN. There’s a near-complete disconnect between what’s truly good for the patient + what’s profitable protocol for the provider.

That’s not an overstretch — there’s an abundance of data to prove that statement + even more HIDDEN data out there (like in real-deal, not-paid-for-by-politics-or-pharma think tanks) to support that claim.

And beyond the data — hidden or in plain sight — ask the people

I spent the majority of my time with families in the special needs community. An overwhelming, undeniable majority had adverse pregnancy + birth experiences. No one was listening to them. By conventional standards + education, I was taught to prioritize the data. But that didn’t feel right. 

We Have Pregnancy + Birth Options

When the time came for us to look into having children as a newlywed couple, we initially thought we didn’t have a choice. We thought we had to follow the conventional standards because we were taught that there was only one way to do pregnancy + birth. 

But when I reflected back on all that I had learned in that research experience — the experience that ultimately proved to me that I don’t actually want to go to medical school after I’ve spent my entire life preparing for that career — I realized that I don’t actually want to give birth in the conventional setting either.

[Related: Our First Home Birth Story]

And when I made that decision, I realized something else. 

Just as my entire body was rejecting that medical school pursuit the entire time, my body was rejecting that medicalized pregnancy + birth idea.

I realized that my entire life I had ALSO stuffed that down. Way freaking down. Because I was Courtney the rule-follower, the one who dependably read the textbooks + checked all the boxes + got the A+ approval.

When I got honest with myself, every time I heard a pregnancy war story, or a planned natural birth going to yet another “emergency” c-section or other intervention, or that a mother believed her baby’s entrance into the world was compromised, my insides twisted. I felt unwell. 

Why weren’t we questioning why birth, a normal physiological event, was suddenly challenging + traumatic for the majority of women?!

When I named + I acknowledged that truth, it felt simultaneously BOLD + REBELLIOUS + most importantly, FREEING.

I felt like I was standing naked + exposed on the top of a mountain + that I had a choice to make. Shrink down small + try to meekly cover my truth, or stand up tall + own it.

Admitting that what everyone else said was “the right thing to do” wasn’t looking or feeling like that for me caused a shift in me.

It was like I had shed a thousand-pound weight off of my back that I didn’t even know I was carrying, much like how it felt when I acknowledged that just because I could do medical school didn’t mean I should. Much like how it felt when I decided to start my own business.

I’ve since walked through life as the most EMPOWERED, CONFIDENT version of myself. My full 100% experience in motherhood + the business ownership that came afterwards.

I make clearer true-to-me decisions unapologetically.

I am more in love with my husband + my body than I ever thought possible.

I am healthier — mentally + physically.

I am a magnet for opportunity.

And so what I’m offering to you here with this story is this:

Just because there’s a conventional system or academic blueprint out there for you to follow with your pregnancy doesn’t mean you have to follow it to a tee.

In fact, you could meet your most empowered self on the other side of the decisions you make to go against that status quo.

Just like in entrepreneurship.

So, what came next?

The Family Start-Up School™

I looked into my options for customizing that blueprint. If you’re an entrepreneur, then this part probably comes naturally to you — you have a natural curiosity to customize + personalize an offer.

I found myself watching the documentary The Business of Being Born by Ricki Lake + Abby Epstein + that was my tipping point.

There was no going back + that felt GOOD.

That felt GREAT.

Using my intuition, my smart sense + my ability to curate thoughtful information + education alongside the experience stories of other parents, I decided that I would step into leadership with my pregnancy, birth + motherhood experience in the same way that I had stepped into entrepreneurship.

And like any true nerd, I documented my decision-making process along the way because it felt like a radical new experiment. 

So, I wrote out what I knew for sure + I culled through everything I could possibly get my hands on. I was taking impeccable notes, simultaneously searching for a couple that looked like us who had maybe chosen to take this type of ownership over their pregnancy + birth experience (+ not finding it at the time).

And now, years later, I’m putting it all into action + I have 2 successful home births to show for it.

I’ve compiled all of that knowledge + examples + simplified them down into the most efficient resource for soon-to-be parents — The Family Startup School™.

The Family Startup School™ is the resource we wish we had as new parent entrepreneurs with full lives + full hearts. Whether or not you decide to have a home birth, a free birth, or a birth center or conventional hospital birth, our intention in this offer is to help you decide what makes the most sense for YOU

Take control of your pregnancy + birth experience so that you don’t have to look back realizing that you stuffed your own specific wants + needs down just to check the boxes needed to get that external approval.

Remember that at the end of the day, what really counts is the approval you give yourself when your head hits the pillow every night.

We share more details about The Family Startup School™ at the end of our free masterclass called The Pregnant CEO: Chief Expecting Officer — how to be the boss of your birth, right from the start — so go grab a seat in the free masterclass. It’s meant to be watched by couples so bring your partner, if they’re into it!

Jumping into that free masterclass could be one of the most powerful moves you make for your parenthood experience. 

Becoming the CEO of Your Pregnancy + Parenthood

Being the CEO of my pregnancy meant that I had to be willing to de-systematize my approach to motherhood or parenthood at-large.

Taking the leadership role of your pregnancy, birth, postpartum + the parenthood that comes after it requires you to first get quiet. Understand your TRUE initial gut feelings about the options in front of you + take those into account when listening to stories from your friends + family.

Being a leader of your pregnancy means creating your own safe system to do your most productive work — producing a BABY, a human, breathing baby — much like when you create your own business as an entrepreneur to do your most productive work for your customers.

Only you know what feels true for you + best for your body + baby.

Making decisions from that place of informed trust — knowing that what you want is more than allowed — sets the trajectory for how you then move through life thereafter as a parent entrepreneur.

You can be in charge here + you can be in charge of what comes after.

And I can promise you that when you step into that leadership capacity, you heal from physical birth faster, you bond better with your babies + partners… The benefits ripple out into the world via your business + your beautiful impact on the community.

The world needs more of that confident leadership. You can do this. We can do this. And when we do, watch what happens.

So, now, we’d love to know: how will you step into confident leadership in your pregnancy + beyond as a parent CEO?

Share your thought process with us + other like-minded entrepreneurs in the chat on the free masterclass. We’ll see you inside!