Should You Trust Your Gut Instinct?

Steve Jobs, Peter Thiel, Katy Perry, and others explain why they trust their gut instinct in major decisions. Garry Kasparov credits intuition in chess, while Ralph Lauren ignored a buyer's demands and followed his design instincts instead. Host Evan Carmichael frames gut feelings as a risk barometer that sharpens with experience.
Chapters
Absolutely trust your gut.
You're born with a gut.
Trust my instincts.
What do you feel like in your gut?
I've learned to trust my instincts.
Trust your gut.
Whatever my instincts are.
Have the guts to follow your belief.
Follow your gut.
Your instincts are very important to you.
Recently, I was with a bunch of other investors who I respect, and they brought me a deal, and I wanted to be part of it, but it didn't feel right. And I wrote millions of dollars on that one, and it just didn't feel right, and I lost it all within 2 years.
So, should investors trust their gut then?
Absolutely, trust your gut. But what about you said earlier, don't be emotional, and sometimes the gut is emotional. No, this is a barometer of risk. It's something internalized for an investor that says, I don't feel comfortable. It's not about emotion, it's just don't write that check. That was recently the first time I didn't listen to that, and I lost everything. So now my radar is up. I listen to my gut. It's not an emotion, it's an index of risk. And you get it as you age. You become a better investor every year. If only I could live to 200, I'd be really good.
I don't think that, that you're born with a gut. I think you're— the gut matures and, and gets better and better over time. And what The struggle that most people have, I think, is learning to listen to it and figuring out how to access it in some way. For me though, what I found was that even though I'm an engineer and an analytical person at heart, the most important decisions I've made had nothing to do with any of that. They were always based on intuition. And the Apple one is a prime example of that. I remember actually forming my list of pluses and minuses and I could not get the chart to work out the way I wanted it to. 'Cause I wanted something to say, you know, this says I should go to Apple, but it would not. Nothing financially would do that. I talked to people I trusted that knew me and they said, "This is not what you should do." It wasn't so easy and people said, "You know, you're just crazy. You're working for the top PC company in the world. How could you even think of doing this? You've lost your mind." And yet that voice said, "Go west, young man. Go west." And sometimes you just have to go for it.
There was a lot of encouragement to trust my instincts, you know, the instinct of use your presence, you know what I'm saying? Like in South Africa, you know, obviously I'm not South African, so I was really aware that, oh God, I'm going to walk into rooms where people have been, lived, seen, smelt, touched, felt Mr. Mandela in person, on radio, on television. And here I come as an outsider doing this, you know, portrayal of him. I was really aware it used to make me very nervous about, you know, if I'm going to do it right or not. And Justin encouraged me to stay with what my gut was. Just stay with that. Don't waver from it. Don't try to be their Mandela or the Mandela they think you should be. Be that guy we've discussed in all the rehearsals and all the script meetings, you know, be that guy, go with that thing. So that was great, actually. To Justin's credit, like, he really helped me sculpt and measure out that performance, you know.
For me, it was never about money and stuff like that. The last time I did something crazy—
Was it going to Idol to do that thing? I think that was a big—
Absolutely. I cannot tell you how many people tried to talk me out of that. Like, please don't do this. Like, this is the worst move you could ever make. And I was like— I was like, you know what? I don't think so. It feels right for my life right now. Like just had had the babies. They were just starting to walk and talk and really become, you know, fully functional people, you know? And, uh, and I just thought, you know what? They need stability. We've been traveling around at that time. Mark was, um, their dad was touring a lot and I was traveling and it was just like, you know what? This is gonna be a good thing for them. For me. I love the show and I just, you know, I just basically said to everybody, kind of overrode— I have to say Benny was kind of on my side. He was like, what do you feel like in your gut? I feel like business-wise, for these reasons, it could be good, but you have to feel good about it. And I said, I feel like it's going to be a good thing. I feel like I have something to contribute. I love music. I love talking about music. I love artists. That's, that's what I wanted. I think this could be a really nice thing. And by the way, we only signed on for one year, right? You know, it wasn't like a thing I was like, where I thought, oh God, I'm going to be here forever. I said, no, I'll do it for a year and we'll see what happens. I wound up loving it so much I did it for 2 years, right? You know, and they asked me back. I was like, okay.
When I went to Bloomingdale's, the buyer said, we like your ties, Ralph, but would you make them narrower? And would you, uh, we don't want to use your label, we want to use our own label, but we'll give you a really good order. Now here I was, no business, and hungry, and I said to the buyer, I said, my heart's in my throat, or whatever the expression is, I would love to sell Bloomingdale's. They were the hottest store, a young, hot store. I said, but I can't sell you. I'm closing my bag, and I'm not going to sell you. 6 months later, they called me back. And they said, Ralph, we can't find your ties anywhere, and we want to buy them. I might want to put a rack in, a rack of ties amongst the other ties. And that was it. The breakthrough was they bought it. The breakthrough for me is that I learned to trust my instincts. I learned to trust my own sense. Because the normal thing to do is say, I'll make it any way you want to. I mean, that's how the world was. I want to sell you the ties, you know, maybe I'll have a new fashion for you next year. "Let me buy it." My philosophy was that I love these ties, I made them. They were not just a business to me, they were my voice to myself.
We should learn how to trust our gut, intuition. Because in most of the stories I looked at, and in most of the quotes I collected, I didn't see people picking up intuition as the crucial element. Of the success. While in my profession, in chess, intuition is virtually everything. Because chess, some people don't recognize it, is a mathematically infinite game. The number of moves in the game of chess, all the moves, contains 120 zeros, which is more than the number of seconds since the moment the Big Bang created the universe. So how can you find your way, you know, in this ocean of possibilities? And of course, how a man can fight a machine that could calculate tens and tens of millions of positions per second? Intuition. Because it's all about decision-making process, and we never employ calculation as the main tool. It's 1% of calculation, even less, and 99% of our understanding, of our ability to find intuitive ways. To compare incompatible, material versus quality, time versus material. So intuition plays a key role, and we have to trust our intuition, our instincts, because in life also we have many opportunities where we cannot foresee all the consequences, and there's only one choice, is just to trust your gut.
I've stayed pretty true to whatever my instincts are as an artist. Sometimes, for worse at first, because I think when you do something that's out of the norm, you have to keep doing it for a little while to make it your own norm. So it's an exciting idea to me that I could be putting a record out and being able to be my own person, to not have to think about what I can't say or can't do because I don't want to lose people's understanding of what I do as a convention, you know. So I'm really excited about the idea of people going, "Oh no, that's him. That's him," you know.
I am amazed at how few people have a belief system. What do they actually believe in? Um, I— and, and yeah, it's okay to offend you guys. Uh, 90% of you will do what's expected of you as opposed to what you want to do. And, you know, I even, when I come to an event like this, say, why am I here? Why would I even bother to take an hour of my valuable time? No, it's true. I have to have a purpose. My goal is very simple. If I can convert one of you— there's probably 400, 500 people here— if I can convert one of you to follow your belief and have the guts to follow your belief, I'll have— I'll think of the hour as well spent. But so I will say, what am I trying to do and why? I don't speak because somebody, you know, will write nice things about it. I always sort of have a purpose, but I have a belief system. And most people, even successful companies, and have big beef with Fortune 500 CEOs I can talk about. There's very little leadership there. Don't have an internal compass of what they believe in. It's what do others expect. You know, when I graduated, I went into entrepreneurship. Nobody went into entrepreneurship out of the business school, and people said, why wouldn't you work for Goldman or McKinsey? I said, why would you? Like, I couldn't fathom why you would want to do that job, right? I still can't, by the way. For those of you going to those places, and I'm sure there's plenty, I'm probably not the right person to talk to you. I frankly don't even care to talk to you. All of you others. I think there's something wrong with anybody who fundamentally wants to go work for one of the consultants or the investment banks today in this part. They don't understand how the world is going to work in the future. But my point again is have a belief system, follow that compass, and I'm overstating it a bit, so there may be some hope for those of you going there, but It's only a little bit of an exaggeration. Let me go back to this issue of Fortune 500 CEOs. I've talked to many over the years. If a New York Times writer writes an article, they want to change their strategy, they want to respond. How silly is that, that some English major who's never had a business job can determine the strategy of a Fortune 500 company? Why? Because they care about what's written, not what their belief system is. Do you know what Elon Musk would say to that writer? Go get a real job. All right. What Jeff Bezos would say? That's leadership. Having a belief system, knowing what's driving you to do what you do, not you fitting in to do career enhancement or making it look good to somebody else. Whether it's to your friends or to your boss or to shareholders. And frankly, you look at all the companies that are languishing in the Valley, the older companies, they generally don't have a belief system. They're generally trying to meet some quarterly target without saying, here's how we will be different and here's how we'll do it. Apple did it languished for 10, 15 years, and then Steve Jobs came in with a point of view and created the most valuable company in the world. He did irrational things. If you go back to January of 2007, January 1st, everybody was saying nobody wants a phone without a keyboard. Nobody wants a phone that costs $699. I can go on with the litany. Those were all English majors writing articles, I have this beef against English majors. Not all English majors are bad, but the majority of them at Stanford are undirected and don't have a goal or a purpose. Sorry. And that's not to say among them there isn't 20% that are really good. They just didn't get the right guidance and ended up in the wrong place. I like purposeful education.
Sometimes in life, to be successful, oftentimes, most of the time, you have to follow your instincts. You have to follow your gut. You have to. Your parents may say wrong, your whoever may say wrong, but you have to do it.
He just affirmed to me that instincts is really important in business. You know, I didn't go to any proper business school or any read any super— follow any manuals like the Record Business 101 or anything like that. I just pretty much followed my instincts, and he just reaffirmed that for me, that, you know, your instincts are very important to you.
Thank you guys so much for watching. I hope you enjoyed. I'd love to know which of the clips meant the most to you and what kind of change you're gonna make in your life or your business as a result. Are you going to trust your gut more? More or not? Leave it in the comments below. I'm really curious to find out. Thank you guys for watching. Continue to believe, and I'll see you soon.
More from Evan

How the Biggest Mistake in History Created A Trillion-Dollar Empire | Sergey Brin

9 Machiavelli Principles That Force People To Respect You | Machiavellian Philosophy

The First 10 Words That Instantly Ruin A Sales Conversation | Vanessa Van Edwards

The Top 1% Mindset Behind The First $5 Trillion Company | Jensen Huang (Nvidia)






