Win Today

#215 | The Beauty of "Failure" | A Key To Winning

• Ryan A. Cass • Season 5

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Failure might be the most misunderstood concept in our success-obsessed culture. The world’s best innovators—from Booking.com to Jeff Bezos to Michael Jordan—have shown that failure isn’t something to avoid, it’s the very foundation of success. In this episode, I unpack powerful stories that reveal why doubling your rate of “unsuccessful attempts” might be the most important move you make toward growth.

Key Takeaways:

  • Failure and success are inseparable twins—every miss is a step closer to the breakthrough.
  • The world’s most successful people and companies deliberately create space for failure to accelerate growth.
  • By reframing setbacks as opportunities, you can transform failure into your greatest competitive advantage.

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Speaker 1:

I believe that we are the best place in the world to fail. We have plenty of practice. Failure and invention are inseparable twins, so what that says is on the other side of failure are the things, the greatest innovations, the things that, oh man, because we messed this up, now our eyes are opening to this completely new concept that we would have never thought of had we not gone down this route. Some of the greatest business leaders and companies that we look at today are a result of a quote, failure or someone saying this is never going to work. You can't do this. 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 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. Let's dig in. I'm thinking about a new business idea, a new product, and it's either going to be a shirt or a sticker, something that says I heart failure. I love failure. Where are we going with this? I've long said that failure equals opportunities, and through recent conversations and studies and books that I've been reading lately, the topic of reframing failure and the importance of that continues to come up, and so I'm bringing this up as a reminder, as reinforcements, that this is how you reframe and use failure as a positive force. Because, with the exception of the word simply creating context, that's really the only reason why I believe the word is useful is so that it creates context, because I personally don't even call it that. It's an opportunity. But for the case that it challenges this norm, or maybe what we see out in the world today, that failure is a bad thing and that there are shortcuts to success, in that there are ways in which we can go from zero to 99 without going through 30, through 50, and we can just move all the way up to the top, maybe something that social media is falsely encouraging. I'm not sure, but this is how we develop a stronger relationship with the concept of failure. This came apparent to me again this week as I was listening to the diary of a CEO the 33 business laws. So this is the book version, not the podcast diary of a CEO highly recommend that. But the book version that Stephen Bartlett wrote I highly recommend that. But the book version that Stephen Bartlett wrote, the Diary of a CEO 33 Business Laws that Can Change your Life, and I believe it's law number 21. And it's double your rate of failure.

Speaker 1:

There was a story about bookingcom. Maybe you've used bookingcom, maybe you haven't, but when I heard about how bookingcom has become what it is today, it almost makes me want to start using them, simply because of what is ingrained in their DNA, which is, hey, failure is a good thing and we're going to fail often. The more that we are failing quote failing the more successful that we will be. Bookingcom today is a roughly $24 billion company with about 24,000 employees as of 2024. 10 years ago they were about a $10 billion company with, I believe, 4,000 to 5,000 employees, so they've really grown into a powerful force in the travel industry. But what really stood out to me about Bookingcom is that they createda role called the Director of Experimentation, and this role was simply intended for Bookingcom to run hundreds and thousands of experiments as to what works well, what gets more people onto the site and booking their trips, their hotels, their rental cars, their flights on there versus what doesn't. So think about this. Hundreds, and now thousands, and multiply this out over the years, tens of thousands of beta tests to stand out as a force to get people to use their site over Kayak or Priceline or Expedia. And they made a rule that they knew was going to create a lot of context failures. Let that sink in for a minute. Let that sink in for a minute. It's not often that we can think about a role, especially in the corporate world, in doing well while creating dozens, if not thousands, of failures, unsuccessful attempts, and I shared before that this has been a key enabler in them doubling their revenue. What does this say? If it's not clear yet that failure is a good thing and failure is not really failure, there's step number one in life, then we must increase by two to three to four times the amount of failure that we are experiencing.

Speaker 1:

You may have heard the quote from Michael Jordan that he has missed thousands of shots. He's been counted on to hit the game winning shot and he has missed it. He has and I'm going to pull up the quote because I believe it's. I believe it is, it is more powerful. You may have heard the Michael Jordan quote. I've missed more than 9,000 shots in my career. I've lost almost 300 games. 26 times I've been trusted to take the game winning shot and missed. I've failed over and over again in my life and that is why I succeed. Folks, if we're not creating unsuccessful attempts, rate of unsuccessful attempts by a large figure.

Speaker 1:

What followed that part in the book was a quote from Jeff Bezos in a shareholder letter to Amazon, and this is in the earlier days of Amazon. It is this. One area where I believe we are especially distinctive is failure. I believe that we are the best place in the world to fail. We have plenty of practice. Failure and invention are inseparable twins. So what that says is on the other side of failure are the things, the greatest innovations, the things that oh man, because we messed this up. Now our eyes are opening to this completely new concept that we would have never thought of had we not gone down this route. Some of the greatest business leaders and companies that we look at today are a result of a quote failure. Someone saying this is never going to work. You can't do this.

Speaker 1:

I've been also studying recently Raisin Canes. You may have gone to Raisin Canes. That is a fast food store and they only sell chicken fingers and they've now are worth almost four billion dollars. Think about that four billion dollars off of one item chicken fingers. And their founder was recently interviewed on the school of hard knocks and he remembers sharing this business plan in college in an entrepreneurship class that he was going to create a chain that only sold chicken fingers, had a great business plan, great model, and the professor actually gave him a failing grade because he simply didn't view the idea as worthy and strong and there's no way that you're going to be able to sell that many chicken fingers. So he failed the, the course failed, the project almost sacked a four billion dollar franchise and, excuse me, I believe they produced four billion dollars in annual revenues. I could, I could have that mistaken, but $4 billion selling chicken fingers.

Speaker 1:

One thing arose from somebody giving a failing grade and saying you can't do this, there's no way. One thing that I'm rolling out in my mastermind group, the Unshakeable Community tomorrow and we've been working together for the entire year is our failure rate and our weekly scoreboard of scary actions that we are taking that we are taking, reason being is that failure is a muscle that we can build. The more that we are told no or attempt to do something and it doesn't go our way, or met with a circumstance that we could have never expected, the more likely we are to eventually then arrive at the destination that we've ultimately envisioned, or the more likely that we are then to actually create and live in our dreams dreams. So the scary action scoreboard is rolling out tomorrow and one thing I'm personally committing to is that I'm going to be taking action of all the attempts that I'm making between this podcast securing bigger and more iconic guests and I know and look forward to the not right nows that I receive, because I'm already saying it's not a no, it's just not right now, but that will happen the amount of newsletter sponsorship actions that I'm taking, the amount of podcast sponsorship actions and requests that I'm making, the amount of people and the amount of attempts that I make pitching the Unshakable Mastermind and coaching, and same thing for the amount of pitches that I'm making to give keynote speeches to schools and organizations over the year, over the coming year. I look forward to the people and the organizations that are going to tell me no, and some will tell me no just because they don't believe in it. Some it might not be in alignment right now, some may say follow up later, but every time that that happens, what that is doing is it's building this resilience muscle, it's building this. Okay. You know what? Sure, maybe we got punched a little bit, but we're so strong now that the punches just roll right off and we keep moving forward. The higher our rate of quote failure, the higher our rate of success.

Speaker 1:

Next week we have a really exciting guest on the podcast, dr Sindra Kampoff, and she is a mental performance coach. She has worked with the Minnesota Vikings, usa track and field, and there was one question that her dad used to ask her as a kid and it was this how did you fail today? How did you fail today? And Cintra went off to become a D1 track athlete and at the time she was one of the best runners in the state of Iowa, used to winning all the time, but from a young age. In her household, her father is posing the question how did you fail? And, as a positive force too, I couldn't imagine at the time. I grew up, and I don't fault my parents for not doing this, but I couldn't imagine coming home talking about how did I fail that day? Now, I believe there was a conversation around that it was related to sports Like, okay, hey, I struck out twice at the plate or I got beat in PE class. Okay. My dad especially said okay, well, as long as you're giving your best effort, you'll learn and you'll get up.

Speaker 1:

Now, if it was, how did you fail? Because I wasn't the best student and didn't really care too much for school at the time, that would not have gone very well, but it made me make a mental note that that is something that I certainly want to infuse into my family at some point in time and, god willing, kiddos at some point in time that, hey, it's okay if things don't go your way, as long as you're not carrying that weight for an extended period of time, and you can quickly look at what it's giving you and how it's making you better. And you train yourself to instantly ask those questions and look that way. So the more reps you're making, the more no's you're receiving, the stronger you are becoming and the more destined for success you are. For success you are. I'll give a couple examples of one time where I felt like the biggest failure ever, and this wasn't necessarily as a result of putting in reps, but more so. Hey, there will be times where maybe you feel like you're worthless or you haven't figured it out yet. Therefore, you suck.

Speaker 1:

Going back to 2016, I thought that I had my life figured out. I was in the corporate world, had just moved out to St Louis Missouri to begin my career with the Boeing company, going to a Fortune 50 organization straight out of college, which was a dream of mine to be able to work for Boeing cool apartment. I've got the woman that I was dating at the time for the last two years of college and she was going into graduate school at Washington University, which is a great private institution for her master's degree and I feel like I've got the world at my hands. I've got the job. I'm going to move all the way up the chain in the corporate world At least I thought so at the time that that's what winning was and I don't have to worry about the dating games. I've got that figured out and this is what my future is going to be. And about a year and a half after being there and we had not long before this had just moved to a new place, adopted a dog, and again I'm more convinced that I've got life by the balls. Like this is it? The plan is all coming together.

Speaker 1:

Next thing, you know, in between her first and second year of graduate school, she goes and travels the world for about five weeks, and which was which is awesome and I, come home from work, had a bad gut feeling as to what was leading up that week, but anyway, me mr positive shrugged it off, came home from work thinking that maybe it'll just be a long conversation, and everything in the apartment was gone, all of her things cleared out, no conversation. I'm left speechless on my knees in the living room, with the dog of course, and crying, and I remember thinking how embarrassing I was, so embarrassed of myself and thinking how could this possibly happen to me? Not knowing that at the time. The question you are wanting to ask is how is this happening for me? It's what I know to be true now and what I've conditioned and what I encourage you to condition into your mind as well.

Speaker 1:

When something doesn't go your way, how is this happening for you? Or when you fail, how did this happen for you? So I remember thinking, man, I don't want to tell anyone about this, especially with how it happened. It was very traumatic and I'm thinking, man, am I really not a good person? And all these things. Now, what I wish I knew at the moment, and what I can clearly answer now, are these questions how did this make me better? What did I learn and what am I doing differently because of this? So what I can tell you now about that moment and something that didn't go my way is that I'm a 1,000 times better man leader, friend, family man, observer, everything and it made me better. It gave me more things to look out for and be more cognizant of for the future, for whenever that time comes, and be more cognizant of for the future, for whenever that time comes. It helped me dig deeper into myself and be able to reassure myself that, hey, here are all the great things I bring to the table. Not to dive too deeply into this, but when something isn't going your way or, as you're on this journey of embracing failure, when you get the no's or when the unexpected things happen, how did this make me better? What did I learn? What did I do or what will I do differently because of this famous story in the corporate world about a man that blew up a factory and got to keep his job.

Speaker 1:

You may be familiar with General Electric it's probably one of the light bulbs in your house very well may be a General Electric light bulb and Jack Welch was the legendary CEO of General Electric for several decades and he came out of school with a chemistry degree and he was working in one of the petroleum plants. Jack was mixing some compounds as a early career chemist and made a mistake and literally blew up one of the buildings. Literally blew up one of the buildings like through the roof and everything, because the compound that he mixed up clearly wasn't the right mixture. And he walked into at the time, the CEO's office and he was ready to give his badge up, give his computer, everything and be fired right there on the spot. And the CEO says hello, jack, why would I fire you? I just paid $16 million to train you. So that was a CEO that understood that, hey, it's okay to make mistakes. Now, jack wasn't being careless, he just was doing the best that he could and made a mistake, blew the roof off a building and now, well, at the time then became the CEO of General Electric and helped GE become one of the most powerful companies in the United States. So I'm wrapping it up with this Failure is a good thing.

Speaker 1:

By increasing your rate of failure, you become more resilient, you move closer towards your dreams, you discover things that you or rather, routes that you wouldn't have considered going down, and you become a better version of you. The best version of ourselves lies on the things that we don't want to do and the things that we're scared of doing. So take inventory. How is this growing you? How is this? What are you doing differently as a result, and how is this moving you closer towards your dream destination? So fail forward, fail fast, and that is what's going to allow you to win today. Thank you so much you.

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Ryan Cass

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