Win Today

#211 | Winning Is: Redefining Success Beyond The Scoreboard

• Ryan A. Cass • Season 5

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What does it really mean to win?
Lately, I’ve been sitting with this question—and the more I observe high performers, the more I notice a common thread: the most successful people aren’t doing everything. They’re obsessed with one thing.

This episode was inspired by my time at the Aspire Tour, where leaders like Ed Mylett, David Goggins, and Jesse Itzler laid out their blueprints for success. What stood out? Simplicity. Focus. Depth. Whether it’s Bezos building everything around the customer, Rolex sticking to watches, or Jiro dedicating 75+ years to perfecting sushi—true winning comes from going all in on what aligns most.

Here’s what you’ll take away:

  • Why obsession with one thing beats juggling many
  • How the world’s best build momentum through narrow, deep focus
  • A new lens on “winning” that goes beyond titles or income
  • How to find your personal definition of winning—one that aligns with your values and fuels consistent growth

Let’s redefine winning together. Subscribe to the Winning Is... newsletter and tune into the show to explore powerful stories and timeless truths that help you stay aligned, focused, and fulfilled.

Thank you for tuning in! If you feel led, please subscribe & share the show to others who you believe would benefit from it.
Keep in touch below!

Speaker 1:

Do hard things. Help one person, be good and do good, live a life of discipline, and you will always win. You have all the tools that you need to succeed. Welcome to win today. Thank you so much for tuning in. My name is Ryan Cass and I am your host. My purpose in this world is to help push people further and harder than they believe possible and become unshakable in what matters most to them in their lives. Every week, you're going to learn from either myself or a renowned expert in their field, and we're going to unveil pieces of our playbook to help you win today. Please, if you love this show, subscribe and share it with somebody that will benefit from it.

Speaker 1:

Let's dig in what is winning? How do you define that? It's a question that I'm going to be exploring more frequently, as the business is evolving and as I've noted two things in particular from notable companies and founders, ceos and creators, and that's curiosity and obsession. Over one thing the more that I dive deeper into people that I admire want to learn more about, and same thing with businesses. Is that what has made so many people that we love to talk about on the show or in circles? We often bring these people up and when we deep dive them, bring these people up. And when we deep dive them, it wasn't that they've done a million things, it's that they've done one to two things, maybe three, extremely well, and they've remained curious and obsessive over that thing. I believe we live in a world now where it can appear that the key to success is doing a thousand different things very well and that's exaggerated, obviously, but doing many things very well, and if we don't have our hands in enough different pots, then we're not doing enough. Yet when we go and dive deeper into businesses and stories and the reason why many of these folks that we admire are the way they are and why they've made it the way they have, a million things don't come out. So why is it that we at times create these definitions or these long laundry lists of here's the key to success, here's how you get rich quick, here's how you create the life you want. Just follow my 27-step guide.

Speaker 1:

I'm committed to exploring what winning is. Even this podcast Win Today. I've had this thought in my mind for a while now as I've been running, and that's where I do a lot of my thinking on life and where things I believe are most clear to me, either running or sitting down with a journal, but usually running first. I've been pondering what even is winning? What does win today mean to somebody else that's listening? Because my version of what winning a day looks like can be completely different than what your version is. As an easy example, my life may look completely different than yours. I don't have a family at home, meaning kids or a spouse that I'm tending to daily. Therefore, my definition of winning may look completely different in that, I would imagine for those that are in that category, winning is that they've taken care of their family that day and been the best father, husband, spouse, leader, wife that they can be.

Speaker 1:

What I'm getting at here is that there's no singular definition to what winning is, and that's why I'm on this quest to explore what that is, be highly curious and obsessive over that, so that we can unlock unique insights for people and help you and help us craft a perhaps a different definition for success, for winning, other than a dollar figure in your bank account, a scoreboard. What's on a scoreboard? What a particular outcome is? What if winning was something very deeply connected to your heart? What if, by creating conversations with notable founders, ceos and creators, just like we have been for the last several years, and focus on what winning means to them, then that can help you and others craft a meaningful definition as to what winning is to you, and I don't believe that it's something that, once we define, it remains fixed forever. Perhaps it does, but perhaps it evolves. But perhaps it evolves. Part of what drives this we'll call it evolution of the podcast now the newsletter Winning Is, which came out today. Part of what's driving that is I'm seeing a trend in where businesses and people that are really, really crushing it in my eyes and that I admire the most are doubling and tripling down on less equals more and focusing on that, or rather remaining open to that thing, or very few things that they're really focused on, meaning that, once we're fixated on this one thing, that we still remain open to the possibilities, the ideas, the thoughts, the perspectives, so that we can then take the best of those insights and infuse them into this one thing that we're really diving deep on.

Speaker 1:

I went to the Aspire Tour Conference last year in Charlotte the Aspire Tour conference last year in Charlotte, north Carolina and I remember walking away feeling extremely inspired. So how cool is that Aspire, inspire. The founders, andrew Cordell and Eddie Wilson, are amazing in that they've built a business tour that has generated over $100 million in revenue, has speakers like Jesse Itzler, david Goggins, ed Milet, cody Sanchez some of the biggest names across sports, across business, across every major industry, and they get these people to come to various cities all over the globe and share their stories. You get to hear keynote speeches and I remember getting to hear from Ed Milet, who's one of my favorite of all time. Hearing him live talking about the power of one more. Hearing him live talking about the power of one more was by far one of the most unique experiences that I've had.

Speaker 1:

As it relates to conferences and business events. There's a different type of energy. When you enter these rooms and when you come in there with an open mind, you leave with so much, so many nuggets that you can go act upon, and these people are giving you their playbooks. One thing I've another thing I've come to learn is that there's no real deep secrets. A lot of these people whether it's Ed Milet, david Goggins, jesse Itzler, everybody I just named they're giving you the game right there, but you have to be open and curious to being able to actually hear it and see it right in front of you. A lot of us are rather many people can be closed off to the game being given to you because we make up this story in our minds, that it's supposed to be something really complex, and we are completely closed off to we're being handed the keys right there. So, at this Aspire Tour conference, andrew and Eddie and Eddie, who sold 76 companies in a year worth $1.2 billion are just giving nothing but free game.

Speaker 1:

Andrew gave about a two-hour keynote about money and he titled it Money Is, Now money is. Think about that. Money is, money is, money is what. Here's some of the things that come out and this is from the stage, but then also probably the same things that we say in our own minds Money is freedom, money is power, money is stress-free, Money is stressful, money is abundant. There's no singular definition, but it's something that we talk about a lot. Andrew had a video series and podcast for a while called Money Is, and he would uncover the insights from these people that I've mentioned Alex Rodriguez, the biggest names To show that money is a game Andrew's words but that it's not something that can be universally defined, however, or, in addition, by hearing what it is to people that we look up to.

Speaker 1:

That can then give us a tool to craft what it means to us and become more clear on what we really want, or to build a better relationship with the thing. So I've been thinking for quite some time on when today, and where I see this business going and where I see the Unshakable Discipline community going. I recognize that I talk about winning a lot, and winning can mean a lot of different things. Therefore, I'm choosing to go on a quest to understand what winning means to notable people around the world, and by doing so, that is going to help you craft your own meaningful and unique definition of what winning is and perhaps help you in your future conquest, because now you know what winning is and you can apply that definition across the things that are most important to you in life, whether it's your family, your business, your relationships, your fitness. You have a more clear or you're open to exploring that perhaps winning is more than a dollar figure.

Speaker 1:

Winning is more than what the scoreboard says. Winning is more than one thing. So we're going to do that. That's what we're going to start pivoting towards, and I'm going to be more intentional about asking people and creating conversations about what winning is to them, and I'm curious as to what we'll find. I believe that we will uncover definitions that we could have never possibly dreamt of and perhaps by doing so, one thing that we learned from somebody else is the one thing that you were looking for that really resonates with you, that you can now use as your guidepost. So we're not going to focus on a thousand different things. We're going to go and focus on what is winning and be highly curious and obsessive and share what we learn along the way, and I'm taking a piece of the playbook from the best and brightest that I've seen so far. We're going to dive deep on one thing that's going to come out in the weekly newsletter, that's going to become more apparent in the podcast interviews and that's going to become more apparent in the content that I'm putting out on a weekly basis. So we have definitions, or rather we've got existing platforms, as to what is money, what is wealth, but what is winning and maybe even this podcast changes to winning is I'm not sure. Let me know what your feedback is on that. I think about when I think about one thing and then I'm not sure. Let me know what your feedback is on that. I think about when I think about one thing, and then I'm going to get into my definition of what winning is, both in long form and in short form.

Speaker 1:

I mentioned that I've noticed two things that stand out with notable brands and people curiosity and obsession. Think about Amazon and what has made Amazon what it is today. Yes, now Amazon sells millions of products and across a wide range of domains, meaning that you can buy clothes from Amazon. You can also host your website on Amazon. Now you can buy your shoes from Amazon. You can also have a package shipped to you via drone.

Speaker 1:

Jeff Bezos, when he was starting Amazon, had a focus on one thing. It wasn't for Amazon to be the best at selling a million products. It was for Amazon to be obsessed on one thing the customer, customer obsession. I've been following Nick Baer's lead on listening to Founders podcast by David Senra and this podcast is. I'm loving it because every week it's diving into the story of a successful founder and their biography and David goes into shareholder letters that have been written, previous books that have been written previous books that have been written, existing books that are on these people, interviews, one-on-one discussions with them really unpackaging. What is it that makes people like Jeff Bezos and Steve Jobs the founders of Nestle? I most recently listened to the story of Michael Ferrero. If you've had the Ferrero and Rocher chocolates with the gold wrapping amazing story, I would have never knew that that family in Italy basically are the pioneers of the chocolate world $40 billion empire. Going back though, on Jeff Bezos, it uncovers that Amazon became so successful because the customer was first and the customer was the point of obsession. The customer wanted convenience, the customer wanted a wide array of products and they wanted it to be able to come to their door quickly without having to go somewhere else. Now, jeff didn't build Amazon to focus on what he thought was the best thing to do. He let the customer dictate everything to what now Amazon is today. So Amazon expanded across all of these domains because of one thing the customer See what I'm saying here. One thing Listening more to the Founders podcast, I listened to an episode about Rolex.

Speaker 1:

If you notice, what is one thing that Rolex makes, what are they known for? Watches. Have you ever thought about the fact that Rolex doesn't make handbags or backpacks or clothing or anything else? They're focused on making the best watch in the world, and that's what they're known for. Sure, if they made a clothing line, would it do well, absolutely Anything that's got that Rolex crown on it. People want to buy it because they've built a brand that people recognize for extremely high quality and craftsmanship. But Rolex is focused on one thing an amazing watch. Private investors or if Rolex was public would likely attempt to lead the company into producing all of these different products, but they got really good at one thing.

Speaker 1:

Many of you may love sushi, as I do, and one of my favorite documentaries that I've ever watched is Hero Dreams of Sushi. Hero J-I-R-O. I may be pronouncing it slightly off. I believe it's Hiro. Hiro Dreams of Sushi, hiro Ono.

Speaker 1:

For 75 years plus and counting, hiro has focused on making the best sushi in the world. He has, if I'm not mistaken, either a two or a three Michelin star restaurant in Tokyo. There are, I believe, no more than 20 seats in the entire restaurant. World ranking officials, presidents, ceos, celebrities they all go to Hiro's sushi restaurant, which is in the middle of a strip mall in Tokyo. You would walk right past it and not know that it's there, yet these are where the most famous people in the world go to have sushi when they're in Tokyo. The most famous people in the world go to have sushi when they're in Tokyo.

Speaker 1:

He only makes a select number of items. He gets his rice from the same exact place. He only buys tuna from one person. Any of his apprentices have to learn even how to perfect rice for three to five years before they're even allowed to touch fish. If the sushi isn't up to Hiro's standards that day, it doesn't get put on the menu, and this would be something that you and I, I'm sure. The things that get rejected off the menu that day are things that you and I would absolutely love and wouldn't be able to taste the difference, but that's the level that he has. If he decided to open up a burger joint, would it do well, of course, but it gets away from his one thing sushi.

Speaker 1:

So I'm going down the curiosity journey myself and that what happens if we become highly curious and obsessive of one thing? So what is winning? I've been journaling on this and I'm going to read to you my journal entry and all the things that come to mind with what winning is, and then I'm going to define it very short and sweet and the reason why I'm going to read out the entry is because it's my intention that by doing so, it may help create new perspective for you. Create new perspective for you. It may help you with your definition. It may help you in thinking of something that you wouldn't have associated winning with before. Much of what's on here isn't tied to particular objectives. It's more tied to states of being, which I've come to appreciate much more, in that I'll share more insights on that. How about that? So here's the entry and here is the, and at the end we'll have the singular. Here's my one sentence.

Speaker 1:

Definition of winning is Winning is more than a score. Winning is closeness and rich connections with special people. Winning is freely exploring the world and local community. Winning is injecting something good in the life of one person. Winning is injecting something good in the life of one person. Winning is recognizing the abundance of good in this world and always seeing the light. Winning is smiling when someone isn't kind or a situation that's not favorable unfolds. Winning is catching sunrises and sunsets. Winning is expanding your body, mind and soul to new heights that your former self wouldn't have deemed possible.

Speaker 1:

Winning is seeking knowledge and perspectives. Winning is going after your goals with all of your might. Winning is creating your dreams. Winning is recognizing the sound of nature. Winning is stopping to appreciate the birds chirping, squirrels running and tree branches swaying. Winning is being grateful for everything in life. Winning is doing your best to embrace and exemplify the word of the big man upstairs. Winning is paving a path for others to follow, guiding those who look up to you and shedding light for those who you don't even know look up to you. Winning is being clear on what you want in this life and creating the time necessary to be clear. Winning is being the rock for your family, regardless of what trials and tribulations have occurred. You are the one who stands tall and makes the choice to be better. Tall and makes the choice to be better. Winning is always staying young at heart, smelling the roses and remembering to make the most of this life, because it's not infinite.

Speaker 1:

Winning is being in constant creation and alignment. That's my short form definition. Winning is being in constant creation and alignment. Constant creation of the things that I mentioned there. Constantly creating deep connection, constantly creating the opportunity to appreciate everything around you, constantly creating a good example for others to follow. Being in alignment is being in alignment with your goals, the things that matter most to you. Winning is being in constant creation and alignment. That's my definition right at this moment and I feel firmly rooted in that. But with curiosity and obsession it could be refined, it could be tweaked, and that's okay. But with that, as I sat and stared at those words on the paper for a long time that I've been journaling about, I feel clear in that those are the things that really matter most in life and when I'm in alignment with that, that's what winning is to me.

Speaker 1:

Not all 27 of those things at one single time time, or however many I just mentioned, but a lot of those things are what I work to inscribe into my DNA, into my way of being, meaning. It's just a part of who I am, it's just what I do and it's not something that I have to write down every day. It's like putting on a shower. It's like putting on a towel after you get out of the shower. Setting a good example for someone isn't, in my view, something that needs to be written down. It's just something you do. Prioritizing connection with people that mean most to you is a part of who I am and it's what I do.

Speaker 1:

There was a point in time where many of those items mentioned were things that need to be written down, because they were things that I want habits and traits that I wanted to build to ultimately be inscribed into my DNA. But that's really now how I define myself and it's my wish that, by sharing that, it gets you thinking about what is winning to you and there's no right and wrong answer here and we're going to keep providing insights on what that really means and how you can shape what that means to you. But I'm truly excited about exploring this further and helping people craft that definition, because when you can look back and it's easy at times to not believe that we're making progress or doing enough but when we have something clearly defined, then we can easily look at that definition and it's almost a binary response Am I in alignment with that or am I not? Or am I working to fulfill that definition? Is what I'm doing today, is what I'm doing this week, in alignment with that or not, with that or not? It almost serves as this instant reminder or incentive like, hey, actually, no, you are, you are winning, you are winning.

Speaker 1:

And then that's going to give you the momentum, energy, excitement to keep showing up to go after the big things, to chase your dreams, to touch your dreams, and perhaps I don't want to get ahead of myself. I'm going to hold my thought. Winning is being in constant creation and alignment. I want to know what winning is to you and we're going to keep going down this path. Be sure to subscribe to the winning is newsletter which is down in the bio or the link show notes, and we're going to win today, but be more clear on what winning is. I really appreciate you guys. Let's go win. Outro Music.

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