Episode 41: Insights on Winning from 2019 Kentucky Derby Winner Owner, Guinness McFadden

Podcast interview (March 2024) with Guinness McFadden Jr., owner of Blackwood Stables, reflecting on winning the 2019 Kentucky Derby with home-bred Country House, his training philosophy, running a private Kentucky training center, and lessons about preparation, luck, and reputation in the thoroughbred industry. The host (Larry Weidel) asks about the Derby experience, farm background, networking with high-net-worth owners, and approaches to developing young horses.
Welcome to this episode of the Million Dollar Mastermind. I'm Larry Weidel, and let's get started. All right, if you're. I know you're a fan of winning if you listen to this podcast, but if you're, in addition to that, a big fan of horses and you love them like I do, you're going to really enjoy this session because today we've got an incredible treat. We've got Guinness McFadden Jr. And actually, Guinness has the horse and the farm that it's where the Kentucky Derby winner from last year came from. And what was unique about it, the second highest odds of any Kentucky Derby winner, 65 to 1. And the. I think he can correct me on this, but I think maybe the only homegrown and local farm that produced a Kentucky Derby winner, most of the time these horses come from all over, but had a local, local hero for the Kentucky Derby. So kind of it's an amazingly big deal. And Guinness got hooked on Racing in 1996 when his aunt and uncle took him to Belmont Park. And he's always a huge sports fan. In fact, he's actually worked out at Northstar Ski Resort when he was growing up. And I know he's a big skier because that's where I met him out in Aspen. But he found where his love was racing and handicapping and those of y' all that have been to horse races, it can be very addictive and very exciting. So he lives in Lexington with his wife Lisa, his daughter Olivia, son Tripp, and has, you know, a really wonderful life he's put together for himself and running Blackwood stables there on 350 acres, and showed me a picture of his lovely daughter there with playing. Not every young girl has a Kentucky Derby winner to play with when she comes home from school, but I don't know if she writes him. But anyway, thanks so much, Guinness, for taking the time out and so welcome.
Thank you. Thank you, Larry. It's happy to be here.
Yeah. And what. Let's do this. Tell, tell everybody what, you know, your takeaway from that experience. And, you know, maybe we get into that one and some other, you know, we start with that one. But other things that you've incredible achievements you've had a chance to accomplish during your life and how you went about doing that. But what, what was that experience about winning the Kentucky Derby?
Well, I think first and foremost, it was. It was a really humbling experience. It's not something everybody gets to do, but it is something that everybody in the horse industry on some Level is trying to do. And I don't want to say we backed into it because we're trying to raise good horses, but, you know, everything just fell into place and we got really, really lucky. Country house, you know, was a home bred of my uncle's who unfortunately passed and then it was up to my aunt and I to continue rolling. So, yeah, it was. I think humbling is the best word. So these to describe it.
These horses run as two year olds and he, your uncle passed in October of 2018, and the race was like six months later in May of 2019. Right. So he passed six months earlier. So he. What a legacy he left you, huh?
Yeah, he. He actually made his country house, made his first start a few days before my uncle passed. So, you know, he was around when he raced, but I don't know if, if he truly could have enjoyed it. But yeah, he had braced one time while he was alive and then, then it all happened.
What. Being around a horse of that caliber and going through that experience, what. How have you noticed that's made a difference in how you go about things? Or has.
Really hasn't. It hasn't changed how I go about things. You know, I think expectations were never that high to begin with and I don't expect that to ever happen again. You know, it's worth trying to do, but expectations really haven't changed. I would, you know, I'm just trying to get another good horse on some level and yeah, hopefully we get another country house. That would be pretty great.
Well, Guinness, I got to remind you of when Bubba Watson won the Masters. They said to him, you know, is this a childhood dream? And of course, he was out of his mind. You know, he had just won it. And he said, you know, the great thing about Bubba is he's so honest. That's also the bad thing about him sometimes. But anyway, he was just smiling as big as he could smile. He said, no, I never could dream this big, you know, but I'd like to remind you that he came back and won it again. So don't rule yourself out, man. The.
I think that's real similar for me because I never would have. That wasn't. That wasn't. I like, you know, it's always nice to set goals that you think may be a little bit out of reach. But I mean, they're, you know, Sheikh Mohammed, the ruler of Dubai, has been trying to win that race for, you know, 40 years. And he's got, you know, billions and billions of dollars invested and hadn't been able to do it. So I wasn't naive enough to think that I would be able to.
Well, talk about, share with people a little bit more of the context. When you go to the museum, I encourage everybody to go to that museum. They have their. Usually museum is boring, but. But if you go to the Thoroughbred racing museum, they have at Churchill Downs as just mind blowingly interesting and fascinating. And one of the things they have there is all of the zillions of thoroughbreds that are born fold every year. And then it went through the elimination process of how that comes down to one, like 20 on an average, 22 of them will race in the Kentucky Derby. Then one will win. But it showed how many. I don't know if it was a million or hundreds of thousands or. But the odds are just staggering, aren't they?
Yeah, I'm not sure the full crop changes every year, but I think you can kind of come somewhere around 25,000 and then, you know, through attrition, you're left with, you know, 20 starters usually for the Derby. So yeah, you get 25,000 down to 20 and then from there you're down to one. So. And it's not, I mean, there's a lot of good, there's a lot of really fantastic horses that have never made it in the Kentucky Derby starting gate for a myriad of reasons, whether it's injury or timing or, you know, whatever it may be, it's not the best horse that wins the race. It's the best horse on the first Saturday in May. And that is the hardest part is getting your horse, regardless of the trainer, getting your horse the best it can be on that one day of the year. It's incredibly difficult. And luck, anybody who tells you that luck doesn't play a huge role in it is kidding themselves.
Well, one thing is how fragile they are, how young they are. And if just like all youngsters are very fragile, you know, they have it a long way from developing, like show jumpers, you know, you start training them heavier when you're, you know, five or something, you know, for those bones to solidify and everything. But bugs can come in and they could. Anything can go wrong at any time, but you can. It's kind of the way life is in the sense that doing great things is always going to be a long shot. And that's no reason not to go for it. But when you do, you've got to make a serious effort. And it's like you've told me before this was, you go about your business in a serious first class way where you can take and stack those odds as much as you can in favor of, you know, the hitting the moon hit, making that, that, that once in a lifetime thing happen. But if you cut corners, it's not going to happen. And you learn. Where did you learn that lesson early on and how did you get that in your head in the horse racing world?
So when I first moved to Kentucky, I started working at Three Chimneys and that, that was just how everybody operated there. It was always if it's worth doing, it's worth doing well. And I think, you know, that's how things have been for me for a long time. Just in general in life is I think the attitude. But I really saw it firsthand there because there's any number of ways you could cut corners raising horses, but you know, you're just better off not doing it. And so I saw it early on at Three Chimneys. You know, reputation is a huge deal in the horse industry. That was always really important to me and part of it is doing the right thing when nobody's watching. So yeah, I think it started there. Robert Clay, the owner of Three Chimneys, set the tone. And you know, no one ever said it like this, but I felt like I was expected to follow and not let him down.
Yeah. And I ask you, you know, the Derby experience is like, if they give you a green jacket like they do at the Masters, but you said unfortunately.
No, no, they, they give you a pretty cool trophy though. So I think I'll take the trophy over the green jacket.
Yeah.
And where, where's I get to, I get to keep the trophy. You know, you win the Masters, you got to leave, you get to wear your jacket for that year, but then you got to leave it in the clubhouse. So. Yeah, but we get to trophy.
Now where do you, where do you have the trophy on display?
We, I have it in my house.
Uh huh. Yeah. And one thing about taking things serious, if you in the horse racing business, you got lots of people that invest that you, they'll invest in the horses, you'll train for them and for them, like you say, you know, there's a lot of high level people putting a lot of high dollars into this and they're not going to, there's just no secrets. They're not going to continue to support you at the top. Most of these people can kind of smell anything. That's if people are trying to take shortcuts. But they can also tell if they're dealing with a quality individual and as a result you pretty, I'M imagining your world. You and I hadn't had a chance to talk about it, but I imagine in your world you've had the opportunity to develop quite a network of real high achievers that kind of working in that circle kind of informs you and helps you stay sharp and notice things that you can improve on. Talk about operating in a business where you have the people with unlimited wealth, like The Arabians and CEOs and entrepreneurs, hedge fund guys. What's it like to operate in that world?
Well, I've been really fortunate. My position at Three Chimneys. Initially, when I was director of sales, we sold horses commercially at public auction. And a lot of my job was to just sit there and watch people look at horses. I got to meet all kinds of different people who had come through the consignment and look at horses. And, yeah, every opportunity I got, I would always like to, you know, ask people questions. Why did you do this? Why did you do that? How did you do it this way? Yeah, and it's also really interesting to see just how. How different everybody's background was. You know, you. I don't. You mentioned hedge fund. I don't think I had one client that was a hedge fund person. It was the randomest things, from, you know, bookstore people to plastic clips on a bread roll to it. Just the most interesting people you're ever gonna meet are in the thoroughbred world. It's just the largest collection of characters I've ever come across playing flat out. It's a really interesting world. And I think, yeah, just a wonderful collection of characters.
When you. What's unique about. Tell people what's unique about Blackwood Stables and the fact Country House came out of a Kentucky horse farm and training operation.
Well, he was. He was actually born at Three Chimneys, which is about, oh, I don't know, half a mile from where Blackwood is, where we actually share a property line. So he was. He was raised his entire life, from when he was born at Three Chimneys to when he went to Lane's End, which is. I share a different property line with. Then he came to Blackwood. So he was, you know, within a. Shoot within a square mile pretty much his whole life, or a couple square of 2 square miles his whole life. He did some time in South Carolina before joining Bill Mott's string. But it, you know, I think what. What makes us unique is it's more of a. There's a few facilities like ours in the United States. Fair Hill would be closest. We're pretty much a private training center. And I think that's, that's what makes us unique is we only do training. Most farms in Kentucky are stallion farms, broodmares, mares, broodmares, stallions, yearlings, that kind of thing. And they're preparing horses for either public auction or to come to places like ours where we, you know, start and pre train them. So that's kind of what makes us unique from that standpoint. There's one or two other operations in central Kentucky like us, but the majority of farms that do what we do would be in South Carolina or Florida.
What can you learn? What, what are, are there any lessons, what, any kind of insights in training horses that you feel you think would people could learn from in terms of training new people for their organization, for peak performance? I remember when I was riding and competing and show jumping, it was like when you get, you know what? I wasn't the trainer. I just did what they told me. I was the dummy on the horseback, trying. I just tried to keep from screwing things up. You know, the trainer told us, told me, told me and the horse what to do. So it wasn't me, but it was like the goals always seem to be, make one specific step forward every day, and then once the horse got it one time, it's like straight to the barn, you know, that's it. Get it in his mind, let him go, quit while he's got that positive new move in his mind. And so how do you go about bringing along a young horse?
Well, most of it is going to be the mental aspect early on, making them comfortable, right, because we're predators. So I think in order for them to not look us at, look at us as predators, you have to get them mentally comfortable with everything they're doing. And then you're just trying to build from there. I like, we're just trying not to screw it up, really. You're just trying not to give the horse a bad experience and you're trying to just do a little bit more each day. And sometimes that's just going for a trail ride around the farm later on in the year. Obviously you get a lot of racetrack time, but keeping things new and different, you know, doing the same thing all the time every day, I don't think is beneficial for anybody. You listen to, you know, Arnold Schwarzenegger talk about lifting weights. It was always something different. He's always trying to do something to confuse the muscle. And I think we're trying to do that with horses, keep it new and interesting because, you know, going around in a, in a circle, making left turns all the time can get boring. And we're dealing with teenagers, you know, so we're constantly trying to build and let them, you know, let them grow on their own and not, not do anything to get in their way. You're always trying to help them move forward.
Okay, well, that's some really great insight. Well, Guinness, I can't thank you enough. This has really been fun and fascinating getting exposed to the behind the scenes of what goes on before and after being a Kentucky Derby winner. And your humility shines through. And you've given us a lot to think about. And I'm really looking forward to the next time we can do this because I really feel like this may have happened one time and may be a dream come true. But I get the idea. You're doing everything in your power to give yourself the best possible chance to do it again and again. And I'm not going to be surprised if it does happen going forward.
Yes, sir.
Thanks for listening to this episode of Million Dollar Mastermind with me, Larry Wydell. If I've helped you in any way, leave us a five star rating and review on Apple Podcasts. For more information like this, listen to our other Million Dollar Mastermind episodes and check out my Wydell Academy YouTube channel and visit us on widelawnwinning.com I'm the million Dollar Mastermind. And until next time, go, go, go.
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