The Ree Drummond Story | Pioneer woman
Ree Drummond grew up a surgeon’s daughter in Oklahoma with big plans — USC, then Chicago for law school. And then she went home for a visit, walked into a bar, and met a cowboy. She gave up Chicago, moved to a cattle ranch eight miles outside of a town of 3,600 people, and at one point was hauling water because the ranch lost running water for months. Her city friends called her The Pioneer Woman as a joke. So in 2006 she started a blog — just to stay in touch, just to have somewhere to put all of it. No plan. No strategy. Just a woman on a ranch in Oklahoma being honest about her life. That blog got 20 million page views a month by 2011. It became a Food Network show that is still running after 40 seasons. It turned a tiny dying Oklahoma town into a destination that draws 6,000 visitors a day. In this episode I talk about what it actually cost her to give up the life she planned, why her voice connected with so many people, and what it means to just start writing about where you are — even when where you are isn’t where you thought you’d be.
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Welcome back to Fifteenish. This is Leah. Hey, friends.
So, there's this woman. She grew up a surgeon's daughter in Oklahoma. She went to country clubs, ballet classes.
She goes to USC. She's got a plan to move to Chicago for law school. She's got her whole life mapped out, right?
And then she goes home for a visit. She walks into a bar, meets a cowboy, and that is the end of Chicago. She ends up on a cattle ranch eight miles out of a town of 3,600 people.
And while all of this is happening, her city friends think it's the funniest thing they've ever heard, and they start calling her The Pioneer Woman as a joke.
So in 2006, she starts a blog just to stay in touch with those friends, just to have somewhere to put all of her thoughts. No plan, no business strategy, no goal, except, hey, here's what my life looks like right now.
That blog is now one of the most beloved lifestyle brands in America. Forty seasons on Food Network, nine best-selling cookbooks, a restaurant, a hotel, a bakery, and an ice cream shop in that tiny Oklahoma town.
Six thousand visitors a day to a place most people had never heard of. And all of it from a blog that she started just to stay in touch. Well, her name is Ree Drummond.
Let's talk about it. Ree grew up in Bartlesville, Oklahoma.
1:34
Unexpected Path
And like I mentioned, this is not the kind of Oklahoma that you might be picturing in your head. Her dad was an orthopedic surgeon and she grew up having a really comfortable life, especially for a kid from a small Oklahoma town.
And she had plans, really, really big plans.
She ended up going to the University of Southern California, which if you know anything about that school, is very much a place that people go when they have those big goals and ambitions that extend beyond their hometown.
She started in journalism, then switched to gerontology, which is the study of aging. And her plan after graduation was to move to Chicago for law school. That was it.
That was her whole plan. But then she went home for a visit and she walked into a bar and she met a cowboy. His name was Lad Drummond.
And I want you to understand who Lad is because his family owns 433,000 acres of land in Oklahoma. Yes, you heard that right. 433,000 acres.
They are one of the largest landowners in the entire United States. He is a multi-generational cattle rancher, very much a cowboy, very much not the kind of person Ree had imagined ending up with when she had her Chicago law dream going.
But she fell completely in love with him. Like completely. She has written about their love story so much over the years.
Honestly, if you've never read any account of her falling for this cowboy, you need to go find it because it is so good. They met in a bar, they fell hard, and in 1996, they got married and Ree moved to the ranch.
This is eight miles out of Pawhuska, Oklahoma. Population at that time was about 3,600 people. Chicago just wasn't on the table anymore.
I think about what that actually feels like to be in that moment.
You're a USC graduate, you had a plan, you were going somewhere, and now you're standing in a life that looks nothing like the one that you imagined in a place that is about as far from Chicago as you can get.
Married to a cowboy whose family owns a third of Oklahoma. Now you have to figure out who you are in that context. Not this version of yourself that was headed to law school, this version, the one on the ranch.
Now we want to be really clear about what this transition actually looks like because I think it's easy to romanticize the idea of trading city life for a ranch and think, oh, how charming and how cozy. But that is not what it was.
At one point, the ranch lost water, not just for a couple of days, for months.
And Ree, the surgeon's daughter who grew up around country clubs and ballet, was now hauling water, just figuring it out, learning to cook for a cattle ranching family, homeschooling her kids, trying to exist in a world that was completely different
from anything she had ever known or planned for. And her city friends thought it was hilarious. They started calling her The Pioneer Woman as a joke.
Like, look at Ree out there on the ranch being all pioneer-y and the name stuck and she leaned into it. In 2006, Ree started a blog.
4:39
Confessions of a Pioneer
She called it Confessions of a Pioneer Woman. And her reason for starting it was about as unambitious as it gets.
She just wanted a way to stay connected to her friends and family, to share what her life looked like out there on the ranch, and maybe to feel a little less isolated in the middle of all of that land. That was it. That was the whole plan.
Stay in touch, share some stories, maybe some recipes. But here is where it gets really interesting because what Ree did on that blog was so simple and so specific and so genuinely herself, people just couldn't stop reading it.
She wrote about real life. She wrote about the actual messy, funny, complicated version of what it looked like to be a city girl raising four kids on a cattle ranch in the middle of Oklahoma. She wrote about Lad.
She wrote about the cows and the horses and the mud and the chaos. She wrote about cooking enormous amounts of food for ranch hands and family gatherings. She took her own photos.
They were really good ones actually. And she had this voice that just felt like sitting across from a friend who was just telling you about her day. And people ended up finding her.
Not because she was marketing herself or pitching herself or trying to grow an audience. They found her because what she was writing felt real. It felt like a relief from everything out there that's overly produced and perfectly curated.
It was just a woman on a ranch in Oklahoma being honest about her life. By 2011, just five years after she started, the Pioneer Woman blog was getting over 20 million page views a month.
6:01
From Blog to Brand
This was all from a blog that she started to stay in touch with friends. Now, back it up a year before the show even launched, she appeared on Throwdown with Bobby Flay on the Food Network.
For anyone who doesn't know, Bobby Flay is one of the most well-known chefs in America. He challenges home cooks and chefs around the country to cook-offs in their specialty, and Ree beat him.
In her first ever television appearance, she just showed up and cooked the way she always cooked, and she won. The Pioneer Woman cooking show launched on the Food Network in 2011. It is still running.
Over 40 seasons. Over 500 episodes. It is one of the longest-running cooking shows in Food Network history.
And then, there's her small town. Like I said, it's about 3,600 people. It's not a destination.
It's not a place that was on anyone's travel radar. And in 2016, re-opened the Pioneer Woman mercantile right in the middle of downtown Powasca. She was in a 25,000-square-foot building.
There was a restaurant, a bakery, a retail store, all in one. And people came. Like, a lot of people.
The mercantile draws an average of 6,000 visitors a day to a town of just 3,600 people. Isn't that wild? Just do the math.
6,000 visitors a day to a town of 3,600 people. And then she opened a hotel right down the street called The Boarding House. And then a pizza place.
And then an ice cream shop. Ree Drummond essentially just revived a dying small town by opening businesses that brought people there, specifically because of her. Because of a blog that she started in 2006 just to stay in touch with her friends.
Ree Drummond did not set out to build a brand.
7:52
Unplanned Success
She did not have this vision in her life of building this media empire or a product line or a restaurant empire in a small Oklahoma town.
Remember, she had the plan of going to Chicago, going to law school, and that plan went in a completely different direction when she fell in love with a cowboy.
And for a while, I'm sure that probably felt like a loss, like this life that she had just imagined for herself just wasn't going to happen.
But instead of fighting it or grieving it forever or spending her whole life on a cattle ranch, wishing that she was somewhere else, she just leaned in.
She picked up her camera, she started writing, she cooked enormous meals for ranch hands and photographed every step.
She shared it with her friends, then her friends shared it with their friends, and then strangers started finding it, and then 20 million people later were reading about her life on a monthly basis on a ranch in Oklahoma.
She built a life, and the brand came from that life. I really want to think about that distinction a lot, guys, because I think we're so conditioned to think about building something as this very strategic, intentional and planned out process.
You identify the market, you find the gap, you build the product, you grow the audience, and all of that is real, and yes, works for a lot of people. But Ree's story says something different.
It says that sometimes the most powerful thing that you can build is just an honest record of your actual life.
That showing up consistently and being yourself, genuinely, not this curated version of yourself, but the real, messy, complicated, funny version.
That is actually a strategy, and maybe that's the most sustainable one there is, because you can't copy it. Someone else can try and do what Ree does, and it won't work out the same way because it won't be Ree.
The thing that she built is so specifically hers, is her voice, her ranch, her family, her love story, her food. There is no version of it that can exist without her being exactly who she is. Here's the other thing.
She started this in 2006, on a blog in rural Oklahoma, and it was at a time that the internet was still pretty new, and nobody was really talking about content creators as a career or even a business.
She was just writing because she needed an outlet and it helped her feel connected, and she kept doing it consistently for years before anything big happened. But let me remind you, 20 million pages a month did not happen overnight.
The Food Network Show didn't happen overnight. The Mercantile didn't happen overnight. It happened because she showed up for years doing the thing that she actually loved, and eventually the world caught up to her.
I also think about where she started. She lived eight miles outside of a town of 3,600 people. Remember, she didn't have running water at one point.
The location didn't stop her. The isolation didn't stop her. The gap between the life that she had planned and the life that she was actually living didn't stop her.
She just started writing about where she was. And that part just really gets me because I think so many of us are waiting for conditions to be right before we start, waiting until we have more time or more space, more resources, more clarity.
And Ree was on a cattle ranch in the middle of Oklahoma with no running water for a period of time with four kids. And she just picked up a camera and started writing. And it wasn't because the conditions were right.
It was because she needed somewhere to put all of her thoughts. I think about the times that I've told myself, oh, I can't start yet because I don't have the right setup or the right location or the right moment.
If I was on video right now, you would see that I'm sitting in my six year old daughter's closet, recording this as I speak. I don't have the right setup. I'm just doing it every single week.
Well, then I think about Ree Drummond hauling water on a ranch in the middle of Oklahoma and starting a blog because she wanted to stay in touch with her friends. And I think, okay, yeah, no more excuses.
Her friends called her The Pioneer Woman as a joke. And she took the joke and built a freaking empire out of it because she knew who she was and she wasn't embarrassed about it. And she just kept showing up.
So here is what I want to leave you with.
12:14
Embrace Your Reality
I want you to think about what is the one thing in your life that just feels like the plan didn't happen. Maybe it was the path that you were supposed to be on that maybe it went somewhere else.
Because I wonder sometimes if that detour or the one that maybe you thought was a loss at the time, maybe that's the whole story. Maybe the thing that you were supposed to build was never in Chicago.
Maybe it was right there on the ranch and you just had to start writing about it. Ree's friend called her The Pioneer Woman and she just took it. She didn't fight it.
She didn't feel embarrassed by it. She didn't try to rebrand into something that sounded more serious. She just said, yeah, okay, that's me.
And then went on to build a freaking amazing business around it. There is something so freeing about that, about just accepting where you actually are and what your life actually looks like right now.
Even when it's not how you planned or even if it's kind of a joke and you just start from there. Reed didn't wait until she had a strategy.
She didn't wait until the ranch felt less remote or the situation felt less overwhelming or the plan made more sense. She just started writing about where she was, and 20 million people a month showed up to read it. Thanks for being here.
I'll see you next week.
Sources & Disclaimer
• The Pioneer Woman — thepioneerwoman.com
• Wikipedia — Ree Drummond entry
• Food Network — The Pioneer Woman show page
• The New York Times — various profiles
• People Magazine — Ree Drummond features and interviews
• Tulsa World — The Mercantile and Pawhuska coverage
• Ree Drummond — The Pioneer Woman: Black Heels to Tractor Wheels (William Morrow, 2011)
All facts shared in this episode are based on information available at the time of recording. Any personal reflections, interpretations, or opinions are my own. If anything is found to be inaccurate, I’m happy to issue a correction
