Go for Stupid with Steve Sims

February 7, 2023
James Whittaker

Check out this episode on the Win the Day Podcast

You miss 100% of the shots you don't take.”

Wayne Gretzky

Steve Sims is a master at making the extraordinary happen.

Growing up in East London, Steve began his career as a bricklayer for his family’s construction company, but grew tired of the long hours and low salary. He committed to surrounding himself with people who had more money, and were having more fun, and that’s exactly what he did.

As his network expanded, Steve went on to start his own luxury concierge company, Bluefish, that made once in a lifetime experiences happen for the rich and famous. He’s organized private dinner parties at museums in Florence with Andrea Boccelli as the guest tenor, sent people down to the wreck of the Titanic, and brought guests on a private tour of SpaceX led by its legendary founder, Elon Musk.

As a speaker, Steve has presented to Harvard and the Pentagon. He’s also worked with an eclectic mix of leaders and changemakers, from Elton John and Richard Branson to Donald Trump and Sting. He’s also the author of multiple bestselling books, including his latest book Go for Stupid.

In fact, it’s that ‘Go for Stupid’ mentality that’s underpinned ALL the success he’s had today.

In this episode:

  • Steve’s journey from bricklayer and bouncer to becoming friends with mega celebrities.
  • How he’s been able to make these unique – and seemingly impossible – experiences happen.
  • A step by step guide to connecting with influential people and industry experts; and
  • How you can use the ‘Go for Stupid’ mentality to big success in your relationships and your career.

Before we begin, the right bit of inspiration can completely change the trajectory of someone’s life, so if there’s a friend or loved one who needs to hear this episode or could use some help to Win the Day, share it with them right now.

Let’s WIN THE DAY with Steve Sims!

James Whittaker:
Steve, great to see you. Thanks for coming on the show.

Steve Sims:
It's a pleasure. Thanks for having me.

Was that all you got on your résumé!? You couldn't have done a bit more in your life?

Pretty shit, isn't it!? I like being lazy.

What was the mindset around entrepreneurship in your household growing up?

It didn't exist. I was a '66 baby, so my parents came from parents who had just suffered the war. So the mindset was basically get a job, work your way up and then retire. That was it.

Back in the '70s, '80s and '90s, if you were an ‘entrepreneur,’ that was code for the fact that you couldn't get a real job and you were probably selling stolen car stereos out of the back of your car. Entrepreneurism was not an endeavor that garnished any respect. Now they're bloody rock stars. But back then it didn't exist. If you were an entrepreneur, something was wrong with you.

And so my parents were very much of the, get a job, settle down, work your way through, get a pension, basically everything that their parents had told them. But entrepreneurs, we're a little bit different.
I was aggravated, and I was pissed off. And that's what entrepreneurs do. We just get aggravated until we find something. Then we find a solution and we find other people who have got that problem and sell that solution to them. That's what an entrepreneur does.

So I don't think it's a case of, when did you discover... You were always an entrepreneur or you weren't? And I came from a big family with cousins and stuff like that, and I was the only person that really had that aggravation. The rest of them just wanted to sell.

A huge turning point for me was when I moved from Brisbane, Australia, where I grew up for the first 28 years of my life, over to Boston, Massachusetts, about as far away from Brisbane as you could get. That is where I first saw entrepreneurs, people who were my age and younger, who were doing cool things, they were pitching ideas, they were raising money.

Because I had a traditional path in mind as a result of the city I grew up in, ‘entrepreneurship’ was not something I’d really seriously considered before.

When did you first gain access to real entrepreneurs and when did you believe that route was actually possible for you?

When we look for something, we see it. You left Brisbane and you came over here to Los Angeles and all of a sudden your eyes were opened up to something. But you traveled that far to find it. I wouldn't be surprised if it was all around you in Brisbane, but you just weren't open to seeing it. But it took that to move.

Same thing happened for me. I left the UK, I had a job in Hong Kong and I literally went that far, failed at a job. But now, because my mind was open to it, that's all I saw. I actually wrote an article in my new book Go for Stupid on the color of the car. Have you ever been in a car park or in a dealership and there's a car there and it's a funky color, it's an orange, it's a blue, a purple, whatever. 

You walk past it and you go, “That's a weird arse car. I haven't seen that color before.” Then you get in your car and you drive home and on the highway, what's the only color of a car you can see!? When your mind is open to something, that is literally all you can see.

When your mind is open to something, that is literally all you can see.

Now, you came all the way over here, going, “I want to find this” and ta-da, it appeared. I think things happen when we actually search for them. For me, it was that aggravation. I had to find something.

I'm sure as shit there were successful people around me, but I wasn't one of them. I had to get out of that sandpit. I had to go out and find it. And I found it by starting off in Hong Kong. 

But for people out there thinking, “Oh my God, do I have to leave my country?” No, maybe you just have to open up your mind to be able to see what you're looking for.

Yeah, it's so true.

I was traveling back and forth a lot, but one trip back home to Brisbane I noticed and became immersed in this massive entrepreneurial culture bubbling under the surface. Previously, I just hadn’t been aware that it even existed, until my mind was finally open to it, like you said.

We've got to be open to it. We've got to see what we can see.

I remember a friend of mine – he's departed, but will never leave – Dr. Sean Stephenson. He used to turn around everything that ever happened to him. The lad had a body that was busted up, sitting in a wheelchair all his life. He had every reason to complain, but was one of the funniest, sharpest dudes on the planet. Whatever happened, he would go, "Was this done to me or was this done for me?" Just having your head question that allows you to use the ability to go, oh, this was good.

Because I guarantee you, anyone who’s listening to this podcast, especially us, we've been through the shitter, we've been laughed at, sued, ripped off, poked fun at, it's just what happens to entrepreneurs.

Whatever happened, he would go, "Was this done to me or was this done for me?"

And in every single one of those moments we go, oh my God, this is terrible. Until a week later when you go, that was actually probably the best thing that ever happened to me. I know of contracts that I lost, that I cried myself on that first night, only a week later to go, “I’m bloody glad I dodged a bullet with that one,” or “I’m Glad I didn't get into a relationship with that fella.”

All of these things happen. It's that ability to reframe what goes on before it happens or after it happens, that actually enables you to take the gold out of it.

So true. Stop judging events as they happen.

Oh yeah.

The trouble is how you react to it is how you are going to dictate what is received. So if you look at something as a bad scenario, guess what it's going to be? If you believe you can't, you're right.

So you've really got to start opening up your mind to what is possible and plausible.

What's the best way for you to learn? If there's a new skill you want to develop or knowledge that you want to have, what do you do to understand that concept and to make sure you acquire that mastery?

So it's the classic, if you don't use it, you lose it. And your brain is a muscle. And if you don't feed it and get it working, it's just going to fall into a sequence of, oh, this is what's normal. I'm going to handle this life because it doesn't ask much of me.

And I wanted more of it. So I was always pushing myself, how could I do it? Now the funny thing is, we dream and we're curious as kids, and then it's beaten out of us as teenagers.

Have you got kids?

Yes, I’ve got two. A three year old and a one year old.

Three and one. All right.

So up until the age of five, they're going to strap a towel around their neck and they're going to jump around the room going, “I'm a superhero, dad!” And I've got three kids. As a parent, you go, yes you are. What superhero are you? I'm Space Boy. Good for you!

And they get to 12 and they're doing that, we tell them to grow up, don't be stupid. We stifle the creativity, we stifle the curiosity, we stifle the imagination. But if we don't, that's where the real power is. So you've got to start retraining your mind back to being a five-year-old. My wife always says I'm a 55-year-old five-year-old, which is really good because I'm 56 now. But that's what she always said.

You've got to start retraining your mind back to being a five-year-old.

Because I'll always look at it like a child. I'll always look at it with curiosity. And some of the most impactful people that I've been able to work with and communicate with – Larry Page, Bill Gates, Elon Musk especially, Richard Branson, John Paul DeJoria – they are all curious kids. They want to know how that works and want to pull the back off of it to see what it's doing, and they've got that curiosity.

So one of the ways I got that back was to start acting like a child. The name of the book, Go for Stupid, that was a terminology that we used 18 years ago. Someone would come to us going, “Hey, I want two front row tickets at a concert.” We'd say okay, then we'd sit down around the table with all the crew and we'd go, how can we make that request stupid? How can we get silly with it?

Now here's the funny thing. If I say to you, all right, I want to do this, and we turn around and go, how can we make that impossible? How can we make the impossible possible? We're going to break through that. And then I turn around and I look at this and I go, well, how can we make that stupid? How can we actually make this ridiculous?

Now here's the thing, when I spoke to you about being impossible, do you know what you did? You gritted your teeth. You do this, you tense up, you constrict. But when I say to you, let's make it stupid, you go, ah yeah.

Every time I play that with someone, they do the same. When we actually have a goal and we make it a stupid, ridiculous, audacious goal, we smile and then the new ones click in, we become a kid. Wow, we're going to have fun with this. What can we disrupt? And that's what happens.

So the way to actually train your mind, and it's really easy. Anyone that's got one of those web tuners for radio stations, pick a different country, a different type of music, listen to it for an hour. When you're driving home and you turn right, turn left, go through the back road and then find that little street that you never saw before.

And here's a classic one. When you go out for dinner, we always buy the first one or two appetizers that we're used to having. We love potato skins, we love spring rolls. Pick something you've never had before. So what we used to do, we used to pick an appetizer that we knew and we liked and something we had no idea of. I was gambling on $3, $4, $5 of an appetizer.

Now I can tell you, especially if you've traveled to Japan, you'll have some of the weirdest things in the world.

You’re like, “Don't even tell me what it is!”

Yes! I have eaten things before and gone, oh my God, how is that a food group? But the trouble is your mind gets used to it, so we do things differently now. 

I remember my kids always used to complain, “Why can't we just get the usual two that we like?” Now they're in their teens and their 20s, they're, “Well I get to pick. That's weird, I'm getting that!”

And it trains you to accept different things. Again, just like your travel, when your mind subtly starts listening to different radio stations, be prepared that you're going to turn left rather than right. Go and watch a movie that you have no normal relevance to whatsoever. And eat something you never would've normally. Your head goes, whoa, it does things differently now.

And it's like that purple car, wherever you travel, it suddenly starts going right, well we are the kind of mind that looks for opportunity now. Where is it? And when you're open to opportunity, what's the only thing you see?


Check out the YouTube or podcast version where Steve Sims does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


I think one of the best things about having kids is it gives you a blank canvas, a clean slate all over again for you to appreciate all these amazing things that are happening in the world.

So reframing that word ‘impossible’ to ‘stupid,’ something that you can actually have fun with, makes possibility come true. You're almost connecting more dots from a blank canvas to elevate your idea of what's possible and gives you the best chance of being able to execute on that.

Yeah. You can actually steal from your kids, which is great because you can see that innocence, you can see that ignorance and you can go, I'm having that. Why am I doing it like this? Oh, I know why I'm doing it like this, because my parents and the guy that used to employ me when I was 17, he always told me that's how it had to be. And then you realize it doesn't have to be that way.

I was up in Tesla with Elon Musk and he said, “We never look at the problem. We understand why the situation's there in the beginning to create that problem.” Everyone is out there throwing oil on the squeaky wheel of a wheelbarrow that they don't use. Instead of replacing the wheel, lose the wheelbarrow.

Everyone is out there throwing oil on the squeaky wheel of a wheelbarrow that they don't use. Instead of replacing the wheel, lose the wheelbarrow.

So there's a different context and parameter of the way you can reframe things. And it does take a little bit of effort, but then it becomes a habit. When you start getting into it, when you start eating healthier, when you start living better, when you start demanding more, then all of a sudden your life starts changing.

You go, well hang on a minute, I like this. And so it's a great habit to get into.

Was there a tipping point for you with that go for stupid mentality, where you were, wow, I cannot believe the momentum I'm establishing with this, I've got to step it up and see where it takes me?

There was no stepping it up, because I was always ignorant. 

See, you've got to understand, I never wanted to launch a concierge firm, dumbest idea on the planet. If podcasts had been around in the '80s and the '90s, shit, I'd have gone down that route.

But I knew that having a conversation with a poor fellow at the bar was useless. Because I was poor and I knew those conversations never got anywhere. So I didn't want to talk to a poor person, why would I? I wanted to talk to a billionaire. 

I wanted to talk to a billionaire and go, how come you're a billionaire? I'll get up at 4:00 in the morning, I'll go to bed at 1:00 in the morning. I'll do anything. How come you are a billionaire and I'm not?

I knew that having a conversation with a poor fellow at the bar was useless. Because I was poor and I knew those conversations never got anywhere.

I wanted to have those conversations. So I always used to say I was not in the business I was in. The business I was in was to have a conversation with affluent people. And I've had conversations with people that own things like countries and that was my business. Hey, if you want a drum lesson with Guns N' Roses, if you want to go and see the Titanic, if you want me to shut down a museum in Florence, to get Andrea Bocelli to serenade you while you're munching your pasta, so be it. But then in two days time, me and you are going to sit down and we're going to have a conversation.

That was the business I was in. I wanted to find out why that was going on. Entrepreneurs, we're always defensive, aren't we? We leave a 40-hour job with regular weekly pay, to working 200 hours a week with irregular pay. We're not smart, but we need to be in control. And you find yourself being defensive. 

I would always say to Clare, my wife, and we've been together since we were 16 and 17, who never panicked, I'd say to her, don't worry, I'm doing this, so I'm going to have one of these and then I'm going to get a real job. And I was about eight years into it, and I got this deal with this little-known car company called Ferrari, in Monaco for the Formula 1 Grand Prix.

And I said to Claire, don't worry, everything's going well. Once I'm over this event, once I've done this, once I finish with this place, then I'll get a real job. And I said this to her and she turned around and she said, “You know you've had a real job for eight years now. You are the go-to guy for billionaires all over the planet. We've never missed a rent payment. We fly around the planet in first class. You do understand that you created the job that you actually looking for?”

And I was like, oh, I didn't realize that. And of course when that happens, all of a sudden you do what all entrepreneurs do with a good thing, you screw it up! I started thinking, “Oh, I better look a certain way. I better speak a certain way.”

And so you took away the child mentality and you moved to more of the adult one?

You do. So I completely and utterly ballsed it up. 

I spent a good 18 months screwing up everything that was good. And then I got it all back again, thankfully, and got back to the innocence and the ignorance of asking the questions and going forward.

But that was really it, really understanding that once I'd got to where it was, then it was a case of, well okay, now where can we go? And I remember, when my client wanted a dining experience in Florence and that's all he asked me. And I ended up shutting down the Accademia Galleria, which is the world famous museum that houses Michelangelo's David.

And at nine o'clock at night, setting up a table of six at the feet of David and then halfway through having Andrea Bocelli coming in and serenading. A big deal, bloody cool. And I pulled all of this off and I was in Rome at the time. I'd gone down to Florence, I only had two days to pull this off. So everything just landed. And when you push yourself, it's amazing what happens.

So in two days I pulled this thing off. And I sat there on the Wednesday night, it's about 7:00 in the evening and I'm next to Andrea Bocelli in my own museum. No one else in the museum apart from us. And I'm just chatting away to him. His wife Veronica was there as well. And literally, I can't overstress it, my body just went into a cold sweat. I just literally went, oh…

You know when they always say someone's walked over your grave? It just went through me. I was shoulder to shoulder with Andrea and he is blind. And he could feel me move. And he said something to Veronica and Veronica leaned in, and she went, “Are you okay?” It just suddenly occurred to me where I was, and who I sat next to, for what purpose, and I can't believe it.

It was that little kid in East London going, “Look at this!” I've always tried to stop and smell the roses and to look around. But I've been in situations before and I'm just, how the hell is this happening?

And all entrepreneurs, we all get that imposter syndrome, don't we? Kids don't, kids couldn't give a shit. You introduce a child to Elon Musk, he's just going to go, “Hello, show me a rocket!” He ain't going to give a shit. Show a 40-year-old guy trying to grow his business to Elon Musk, he's going to crap his pants.

So I've always tried to be that childlike mentality with things. And I often joke with my wife that I'll grow up one day and she knows I'm lying.

One of my favorite quotes is, “Action is the real measure of intelligence.” It's a Napoleon Hill quote. It goes very much hand in hand with the Wayne Gretzky quote, “You miss 100% of the shots you don't take.”

When you hear those quotes and you think about that mentality, what comes to mind?

I always used to say, I get an automatic ‘no’ for every question I don't ask. And then I heard the Wayne Gretzky one and I'm thinking, shit, everyone's probably thinking I'm stealing his!

I've got a friend of mine, he actually lives not far from here. I'm sure you've heard of him. Jay Abraham. Cool ass dude, Jay, lovely boy. And Jay said to me many, many years ago, “Do you know you've got a greater ‘I can’ than an ‘IQ’?” And I really liked that.

Jay said to me many, many years ago, “Do you know you've got a greater ‘I can’ than an ‘IQ’?” And I really liked that.

You can have an incredible idea, that's going to save the planet, but without action it’s a waste of time. And then we all know half-assed ideas with action have become billion-dollar businesses.

So it's not the intelligence behind it, it's the action. It's the movement, it's the momentum. And when it goes wrong and it goes to shit, that's the education. And then you refine that and then that becomes the new intent based on education combined with experience. You're now credible, and that makes things your success.

Yeah, it's so true. 

I get very frustrated when I hear someone say how many ideas they’ve got. Who cares!? What are you going to do about it, is the real question.

Show me one that works.

Relationships have been everything for me. They've been everything for you in your career as well. What's the best route that you have found to be able to connect with influential high-level people as quickly as possible?

Purpose and value. 

People ask me that question, how do you get these relationships? How do you maintain them? How do you look after them? And I say, I play a barbecue game. This Saturday night I'm having a barbecue. And I tell you you’ve got to come over to my barbecue. And you go, yeah, I'm going to be there. And I said, great. 

What's your first question? Now, guys are shit at this. So whenever I'm in a room, I always try to pick on a guy. I always go, who wants to play my barbecue game? You hear the guys and the girls. Okay, I'm not picking on the girls, because you get it right every single time. Never had a girl get it wrong once. Guys, can be embarrassing.

I did it with Brandon Turner, famous guy from BiggerPockets. I love Brandon. Love you, Brandon. But he got on to about eight questions on this. And you say to people, what's your first question about this barbecue? They go, where is it? Great question. If you don't know where it is, you can't come. What's your next question? What shall I wear? Great, okay, we're going to keep it casual.

Oh, can I take photographs? Yeah, if you're not bothering people. Okay, what time should I be there? And there's all these questions and then eventually when the guys get tired of questions, they go, oh, what can I bring? And I go, great. It took eight selfish questions to get one that helps me.

And that's how people enter into relationships. You see Elon Musk, you see Elton John, you see Richard Branson and you go, “That person can help me.”

I'm a selfish, self-centered bitch, I really am. I don't move without purpose. And the older you get, you get more selfish. I don't give my time up lightly. I don't give up my energy lightly. I don't give my knowledge up lightly. If someone's going to do something with it, I'm all in. But I'm not just going to leave it on a bench.

So I say to people, you've got to look at relationships like a barbecue. What can you bring to their party? You know that they're going to help you. And good – why get into a relationship that sucks? Why get into a relationship that doesn't grow or challenge you. Now that that relationship with X is going to be good for you? How can YOU make it wonderful for THEM?

See the old saying about getting a foot in the door. But that’s not the trick. The trick is bringing so much value that they lock the door behind you. That's the key.

The trick is bringing so much value that they lock the door behind you.

Let's say, I don't know you, and I want to have a relationship with you. And I look at you and I go, well hang on a minute, he's got a great podcast, he's got great distribution, I've got a book, I want to be on his show, because it benefits me.

Now some people out there are going, well that's very selfish. Yeah it is. But how can I make you desire me? And I go, well, hang on a minute, I've got a network. Hey James, you've got a great podcast. How would you feel if I distributed it to my 100s of 1,000s of followers? How would you feel if you were on my show talking about what it took you to travel from one side of the world to another? Would that help get your story out there? Hey, you've got a show. I know some really cool cats. How would you feel if I'd brought them over to you as guests?

Now I'm giving you a value library. Now you're going, all right Steve. Yeah, how can I help you Steve? Well, funny you should ask that actually, I've got this book. So you've got to think of it as value. And everyone I've ever worked with, I've always looked at them and gone, okay, I know you can help me, how can I help you? And I play the barbecue game. Just keep it simple. How can I increase the value of your life?

People love to default to money every single time. But if you want to see someone with money run away, ask how you can prostitute them. “How much is it going to cost?” Are you kidding? Money only attracts people who don't have any. Anyone that's got much of it, it's not a deciding factor anymore. Wealthy people don't want to talk about money, they want to talk about impact. So you've got to look at the value.

We did a deal years ago, had a client of mine that wanted to meet up with Oprah Winfrey and we contacted them and they were not doing any meet-and-greets in America because of a contractual detail. I think this was before she went and did her own show. She could do group settings and speaking, but not one-on-one.

Then I heard she went to Canada, she was out of contract. She's now on Canadian soil. And you don’t want to go to someone like that who's got a lot of money and go, “Hey, how much will it cost?” So we went forward and we went, “Hey, I know you're supporting the development of these schools.” I think it was either Hewlett Packard or Dell. And we were like, “How would you feel if we put a new computer in every single one of those classrooms contractually for the next five years?”

We were appealing to something that benefited them. Now if you'd have wrapped the cost that it took for us to do that and walked over and gone, “Hey, would you do this for this cheque?” She'd have said no. But the fact that we went and said we are going to do this for something you love, everyone up there that you want to get involved in has a love and a passion. It could be the kids, it could be the school, it could be a charity, it could be adopted dogs, whatever. That may be a benefit to them to help them, to enable them to help you.

What Steve said there is the absolute blueprint of how I've been able to have every single relationship I have in my life today. You as well.

Do you know Keith Ferrazzi? He wrote Never Eat Alone.

Yeah.

Number one New York Times bestselling author, amazing guy, a very good friend of mine. He came on the show as well and he mentioned that you don't invite people into your mission, you invite people into their mission.

And it's exactly what you just spoke about there with the Oprah example. You're providing value for them to do their stuff, rather than thinking that because they’re a public figure they owe you something.

Or worse, thinking that you can act like a dick and – because you hand them a check – you still expect them to dance for you. It just doesn't work like that.

It absolutely does not.

Especially if you’re aiming for a long-term friendship, rather than a transaction. The aim should be to have a long-term friendship with someone.

That's the key.

And in today's world, we don't have a lot of friends. So, you've really got to move with purpose on those. And you said it's a blueprint. It absolutely is. And no disrespect, coming from two guys that action it and don't overthink it.

Wealthy people don't want to talk about money, they want to talk about impact.

See, I guarantee you now – and this is what's borderline criminal – there are people listening and watching this going, well that sounds too easy. It's not, but it is. But you've just got to try it. There'd be so many people that will literally talk themselves out of doing what we just spoke about. And we're sitting here with two examples now of people that actually did this and it worked. 

It ain't hard.

Another mutual friend of ours, Joe Polish, wrote What's In It for Them? Which, alongside yours, I referenced as my favorite books from 2022 on relationships. Joe talks about always leading with value.

And that's what I do, every time I'm sending an email to someone or an audio message, before you pull the trigger, have a quick look at it and just think about what you can do in terms of elevating the value of that. 

The results are just massive.

He's always been good on value.

And the thing that I've always loved about Joe is that he won't enter into a relationship unless he can bring his A game and his value team.

If he looks at someone and goes, “Well, I really want to be friends with them, but I've got nothing to bring,” he won't waste their time. So he really does focus on relationships and realize they are the currency.

You see, during the pandemic, your bank never phoned you up to find out how you were getting on, but your mates did. And then when the shit hits the fan, the bank's not going to phone you up to help you out, because they only give you money when you don't need it, but your friends will. 

So you've really got to realize that, today, relationships are the currency you want.

How did you overcome the mental battle, the imposter syndrome, the limiting beliefs, when you did start to connect with some of these really influential high-level people?

In the early stages, I never had any imposter syndrome because I had focus. When you're driving really, really fast and you're focusing on the road, you're not focusing on the speed dial.

So funnily enough, I wasn't intimidated. I do remember years ago, very, very early on, and I've always been a biker, and there was me and my two buddies and we'd pulled up at this pub just outside of London on these old motorcycles. We walked into the pub with our crash helmets in hand, just to try and look older than 18, to be able to buy a beer.

And so we walked in – and obviously we looked like idiots – but as we walked in, there was a guy in there who was the local Richard Branson. The guy literally owned the local supermarket and gas station. And as far as we were concerned, this was the Elon Musk of our town. The guy always drove around in a convertible, which is stupid in England, and he always had the hot girls. This was the icon of fame and success in our area.


Check out the YouTube or podcast version where Steve Sims does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


When we walked in there, I'd always heard his name, but one of my pals – and here's the dumb thing, I can't even remember his name now – said, “Oh, that's so-and-so.” I said, “Let's go and chat with him then.” And I went over to chat with him. I walked over and I went, “Hey, how are you doing? I'm Steve Sims, you don't know me, but I thought I'd just say hi. 

He looked at me and, bear in mind, I'm a big ugly fella. So when I'm coming at you, you can imagine some people would be like what the bloody hell's this guy want? And this guy looked at me a bit weary and he went, “Okay then, I was just buying a beer. Do you want a beer?” And he offered to buy me a beer.

Now this was in the days when I knew I could get maybe two or three beers max and then I was out of money. I'd just scored a free beer. I was happy with the result! And of course, looking after your mates, I turned around to my buddies to go, oh yeah, great. Do you want a beer, to get him to stump up for three beers?

I turned around to my mates, they couldn't have been leaned up against the wall any tighter if you'd have set a truck on them. They were literally the other side of the bar right up hard. And it seemed to be like a long stall. And I realized the difference between me and them. I saw, I went for it, I didn't have any fear. They saw and they ran away. They were literally pressed up against this bar.

I realized the difference between me and them. I saw, I went for it, I didn't have any fear. They saw and they ran away.

I just got a free beer. Didn't matter where the rest of the conversation went, I'd already got a result! But that was them and us. And I realized when I was young, they were terrified of having a conversation. I was terrified of being them. See, everyone moves with fear. We're frightened of being on stage, we're frightened of driving the car fast. We're frightened when we go past a bush and it rustles. We're frightened of launching a book, we're frightened of starting a podcast. We're frightened.

Fear can dictate your response, but how you respond to that fear is all that matters. You see, I was terrified of being a poor guy that couldn't afford many beers and here was an opportunity for me to get smart. I was terrified of always riding around on a shitty motorcycle. I was just appalled that I was always going to work on a rainy building site, that it just forced me to just run away to something better.

Fear pushed me to take those chances. So I didn't have the imposter syndrome in the early stages, because I was terrified of being my two clowns leaning up against a wall. And even now my life's pretty good. I don't ride shitty motorcycles. Now I can afford more beers than I care. But I am terrified of being in the exact same place today as I will be in six months time.

So between now and then, I have to try new things. I have to have conversations with new people, I have to push myself. And that's what I like to do. I do like to respond to fear in, as I class it, the appropriate way. So I didn't have space for fear. The doubt came in, and the imposter syndrome came in when my wife went, you've already got it. And that's when I sat there and went, oh, shit, now I'd better change.

And there was a two-year period where I was dressing up in new suits and fancy watches. I bought a car, which is unheard of for me. I bought a car. I just so badly wanted to impress you that I lost me. 

Luckily I went back to it. And now I don't have that imposter syndrome, because I'm not trying to impress you. I'll be the asset that you need when you need it. But other than that, I've got nothing to prove.

The placement of fear is really interesting. For everyone watching, listening, and reading this, you need to look at where your fear is placed when a potential opportunity arises. Make sure you’re not letting fear of the moment stop you from changing your future.

I'd like to find the jerk off who wrote that book – the book that says you shouldn't rock up to somewhere on your own. You shouldn't look like that. The amount of shit I get from having an eye piercing and showing up in a black T-shirt. And I get people coming to me and they go, you're going to that event looking like that!?

And do you know what the funny thing is? I'm going to the event, they're not. But now I'm supposed to listen to the opinion. I remember a friend of mine said most people that actually throw hate at them can't afford them. So why am I listening?

Never take advice from someone you wouldn't trade places with.

There’s lot of these rules out there. Don't turn up on your own, don't do this. Don't act a certain way. Be like this, be like that. If I said to you, okay, people don't turn up to a place on their own. Who said that? We all know it, we all hear of it, we all know it's a fear, but who was the person who said it?

I've got a profile picture. And we have sims.media, it's a media company we own, it's a branding thing. And I always tell people, be exactly the same person everywhere. And so on Facebook, there's a picture of me with an Old Fashioned in my hand, you go on LinkedIn and there's a picture of me with an Old Fashioned in my hand.

When I put that profile picture up there, I actually had people I don't know, came out the woodwork and they went, your profile picture shows you with an alcoholic drink.

And I went, yeah. Well it's not very business. What do you mean it's not very business? And they said, well it's not really the right kind of picture for LinkedIn. Where's the rules that say that? And she literally turned around and she went, it's LinkedIn. That was the response. She just went, it's LinkedIn. I'm like, I know you said that.

It's the dark thing that people have these parameters. Who put those parameters out there? And so I'm very forceful, to go, well okay, what's being said, but more importantly who's saying it? And on a normal day, would you listen to him? So why start now?

Yeah, there are people who actively seek out limitations and there are people who actively seek out opportunity. We had Dr. Mark Goulston who came on the show, amazing guy. And he spoke about people like Elon Musk, Steve Jobs, and Jeff Bezos, who look at life as an adventure to be lived. Whereas most people look at life and the world as a danger to be avoided.

I think that's so interesting.

Oh yeah.

It was Joe Polish who said this statement to me. He said the definition of hell is to meet the man or woman that you could have been if you'd tried.

I have one goal, and that goal is to die and then go up to, hopefully the pearly gates. And St. Peter is going to be there at the edge of the bar. He's going to toss me an Old Fashioned and he's going to say, well you had some fun, didn't you?

That's my goal, that's my end.

You mentioned branding earlier. What are the biggest mistakes that you see people make when it comes to becoming a personal brand and getting their message out there?

Oh, very easy. They try to be you.

They look at someone and they go, oh, I want to be really accepted, I'm going to be them.

All the Old Fashioned profile pictures come out then!

Yeah, everyone's going to be holding an Old Fashioned now!

The daft thing is that in branding everyone wants to be unique. They want to be impossible to misunderstand. They want to be easily identifiable as them. And yet the first thing they do is conform to every other parameter of what their industry says they got to look like.

If you're a doctor, a white coat. If you're in finance, a suit leaning up against a sports car. If you're a realtor, you've got to put a picture up there when you thought you were sexy. All of these kind of parameters that they put up, which when you meet them is a disconnect to the person that they are.

You see, what we've got today is a world of noise. And we've had it for quite a while now. People have become very, very intolerant to having to work too hard. We want to know the answer. How many movies now? It's been something that's happened in Hollywood. How many times do you see a movie or a program that within the first 30 seconds the person dies and then they go, three weeks earlier. And then it goes into the story.

Or you watch a trailer of this happening, that crap, and you've seen the highlights. Okay, because we don't want to get in... We don't like to wait now, we need the answers. How many people buy a book and they skip to the last few pages to know how it's going to end before they go forward?
That's the temperature of the room that we're in today. People want to know one thing: can you help me? So when you brand, anti brand, and I mean that. Forget all of the prettiness, this is you, this is what you do, and this is the solution you provide. Those are the elements.

People want to know one thing: can you help me? 

I'll give everyone an example here. Get a desktop. This can't be done on a mobile platform. Get a desktop, get a laptop. Open up your favorite social pages that you are on, your Facebook, your LinkedIn, your Twitter, TikTok, whatever. Open them up, different browsers. And then ask yourself, is it the same person in every picture?

Because as I say, on LinkedIn, you'll be leaning up against a bunch of books that you've never read. You get over to Facebook and you've got my tie on and it's Girls Gone Wild. A completely different kind of theme.

But now open up Apple’s social pages. Is Apple different? Is Ford different? Is Nike different? No, your brand is you. So be you in every single picture. Be a current you, on every single picture.

And then the bios. Is the bio the exact same everywhere? Are you a speaker on LinkedIn, but you're a podcast host on Facebook? And you're an investor and entrepreneur on Twitter. How can you be different people? Don't confuse me. 

I remember, I was looking at a house near Topanga. And I'd seen this house and I really liked it and I found the agent that was selling it. There was a picture of her. Attractive, blonde lady. And I called up. I'm married with three kids, I want to buy a house, I don't want to date her. I want to buy the house.

So I phoned her up and she turned up. There was a good 40 years between her and that picture. And she turned up in this Mercedes, very well put together, very attractive, mature woman. But I felt frauded. She got out of this car and I'm like, who the hell are you? And I looked at her and I thought, if you are okay to lie about what you look like, what else are you going to lie about once you start showing me this house?

So anyway, we went through the house and we spoke, a great woman, ended up buying the house. And afterwards I said to her, I said, your picture, I've seen your picture and I noticed, with respect, couple of years difference between then and now. She went, oh, I love that picture. I had it done 35 years ago or something like that.

And I went, well, just to let you know my feeling, when I saw you, I felt you'd lied to me before you even spoke to me. She went, oh no, people don't think that. And I thought, hang on a minute, you're now telling me what I'm thinking. And even today she still uses that picture. I saw her on a bench the other day and I'm thinking it's incredible.

Today with branding, you've got an anti brand. No one wants to date you, okay?

They want you to solve their problem.

The result.

They do.

So don't go and get some fancy copywriter. Speak from your heart. I don't care if it's got bad grammar, I fix this, great. I need it fixed. You've allowed me to be able to make a decision easily.

Stop complicating shit. We actually openly say that we are there to create clarity in your brand.

Your new book is a great read, Go for Stupid. Highly practical. You've got some great stories in there.

Who is the book written for and who do you want those people to be after they're finished reading it?

Great question.

It's for anyone that's aggravated with what they're going to accept in their standards. We're all being dictated to by people that we shouldn't care about. So I want you to start having conversations with everyone in your world that you want to work with, but also the conversation with yourself.

Joking aside, I ride motorcycles. If you had a camera inside my helmet, you'd see me talking to myself. I literally ride down the motorway going, okay Steve, what are we going to do tomorrow? We're going to do this, because we've all got those little devils on our shoulder. Imagine if everyone's working together, your imposter syndrome, your doubt, the little devil. If you're all working for the same thing, you're now a little mini army and you can go and get.

So the conversations you've got to have, are both outside of your head and inside. But it's those standards. What are you willing to accept? And when you can start adjusting those, people gravitate towards your standards. And what's going to happen to people once they've read the book, they're going to have a new line, a new line in the sand of what they will tolerate, what they will do, why they are doing it. They're moving with purpose.

It's your standards. What are you willing to accept? And when you can start adjusting those, people gravitate towards your standards. 

Do you remember those two and a half years you lost during COVID? Let's start the clock again. So you're now going to learn what you will tolerate, what you will accept, what your standards will be, and how to create impact.

You cannot create more time, but you can focus on the impact you can handle with the time you've got.

Being memorable without needing to have a big financial outlay was another big takeaway I got from that.

Some of the thoughtful strategies of showing that you actually care about people, is the way that you can level the playing field rather than rocking up to a billionaire's house and trying to bring a fancy bottle of wine.

Impact has nothing to do with expense.

Think about when you're driving down the road and a song comes on the radio and it reminds you of when you had your first kiss with your wife, okay? That's just a song being played. So that favorite meal, that glass of wine that takes you back to a moment. Thought is irreplaceable.

And that's what you should be doing. Just try and find something that someone likes and then what can you get that will amplify the love of that. And just focus on the impact. Impact is everything.

This journey that you've been on, is there a particularly dark day that stands out?

There was the time when I had the Ferrari deal and it was very well-documented in my first book, Bluefishing, when my wife actually pointed out, not only did we have a successful business, that went all crap. 

Because I've always been in a black T-shirt and jeans, even back then. And someone actually said to me, oh, you are going to the Ferrari event? I said, well, I'm actually handling most of it. And they went, you're going like that!? And I went, why not? And they went, these are some of the most powerful... You're turning up like that.

And I went out and I bought a couple of tailor-made suits and I bought a watch that was basically the price of a Range Rover at the time. And I turned up at this party in Monaco and I'm on this yacht with Sylvester Stallone. This was in 1997. So it was the Rambo Terminator period. These were the two biggest action stars of the time.

I had Sylvester Stallone and Arnold Schwarzenegger and me in the middle at a bar. And I was all, I'm Billy Big Balls. Look at me. I have got the event with Ferrari, with the A-list celebrities. I got back home to my house, I was living in Switzerland at the time. Do you remember when you used to get the roll of film, put it in an envelope, send it off, and then sometime in the next three years you'd get your photographs back?

They had dictated and fueled my self-doubt. But worse, I had listened.

And I got these photographs back and I was sitting in the office and I'm looking through these photographs and I am proud as punch, this bricklayer, from laying stone, riding around on his shitty motorbike, is now hanging around in Monte Carlo with A-list.

I'm flicking through these photographs and I suddenly realized I wasn't in the photo, it was this prick with a suit and a fancy watch. He was in the photograph, but not me. And I suddenly realized it was the best party on the planet that I never actually went to. And it sent me into a slump. 

I started drinking that afternoon. And I didn't stop. I locked the door of the office, wife was trying to get into the office, she called some friends, they kicked the door down and slapped me around and cleaned me up a little bit. I just could not believe I had sold myself out. 

I had listened to someone that wasn't even invited to the party and they had dictated my depression. They had dictated and fueled my self-doubt. But worse, I had listened. And I went, that's never happening again. And I was violent. That is never happening again. You don't like me. Hey, that's fine. You love me, that's fine. But you'll never be confused. You'll never be on the fence. 

I am impossible to misunderstand. You'll love me or hate me and that's fine either way. But I am not going to be moving around based on your perception of me.

So I got rid of the car, I got rid of the watch. It was an Audemars Piguet Royal Oak Offshore. So every time I see the advert, I still think about that day. We get triggers. And I got rid of the suits and I realized that if I can't turn up on a motorcycle and a black T-shirt…

Not your crowd.

Maybe I shouldn't be turning up.

You're a parent to three kids. What are you doing to make sure that your kids have the same open-minded outlook that you had?

So a friend of mine, Carson Haslam, they've got younger kids and mine are all teenagers or left home now. And he said, have you got any tips? And I said, yeah, just ignore them, because they're only going to grow up to hate you in any case! And that was my parenting tip.

By dressing them all in black T-shirts and jeans, the whole family!

It's funny, because I'm in business with my eldest son. And my youngest son actually helps me with the Speakeasy Mastermind Events. So they're in the business. The only one that's not is my daughter. So who knows when that'll be.

But my son could see the ups and downs of being an entrepreneur. One minute you got a million, the next minute you broke. Next minute you're being sued. Next minute you're being laughed at. Then you got a million again. It's a hell of a rollercoaster. And he was, I'm never touching that. That's weird.

But you can't change your spots. And he now works with me. And it's a constant education to go look, hang on, the problem you're seeing is you. This is happening because of you. So there's a constant education to try and help them find their way. But then there's also that moment where you've literally got to love them enough to let them get hurt.

One minute you got a million, the next minute you broke. Next minute you're being sued. Next minute you're being laughed at. Then you got a million again.

Now I've said that you make a million, then you lose a million, then you get sued. Every entrepreneur I know has got lied to, ripped off, patents stolen, client bank stolen, had their business replicated. I had a friend of mine that actually did whatever it was he was building. And then one of his team actually patented his product and he had to end up buying it off of her.

So we've all been through these, what we call injustices. And that terrible kick in the ball sack moment that you just wonder, will you ever get over again? And you sit there on a Tuesday night going it's payroll on Friday and I don't have the money. How do I get by? But you know what happens? Monday comes around and you pulled it off. And you go, oh, I did that. And the next time it comes around, you go, it'll happen, it'll be done. Why? Because I've done it before.


Check out the YouTube or podcast version where Steve Sims does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


And you become empowered. The good thing about making money and then losing money, is you know how to make money. And so when you make money you lose money and you go, well that worked. I'll do that again, but I'll avoid that a little bit, because that's what put me in the shitter. You become empowered.

So with kids you've almost got to set them examples and tests. Knowing that they're going to get a smack in their nose, just to prove to them that their guard's not tight enough. So you've got to allow them to get empowered. I don't molly-coddle my kids. I treat them like human beings.

And I treat them as responsible human beings, that should be susceptible to their own decisions, and they need to own it. And if you screw up, you screw up. So that's what I hope to do.

Am I doing it right? I don't know. I have a very funny relationship with my kids. We never say nice things about each other, because that's just the thing. But the other day my son made a cardinal mistake. He made an earth-shattering, no coming back from this, complete major capital F-UP, mistake. He went online and said about how proud he was of his dad with the new book, Go for Stupid. And of course I saw it and I screenshot it and I shared it with everyone.

And I went, no kids ever say anything nice about their parents, but I've now got photographic evidence, and he didn't come back from that.

I took the liberty of reporting your post to spam, son!

He was hysterical. So he's, oh my god, it was a weak moment.

On your best day, what's an affirmation that you would write on a flashcard, that you could show yourself on your worst day?

There was a quote that came from John Paul DeJoria, which I absolutely fell in love with. He said, “It'll work out in the end and, if it hasn't worked out, it ain't the end.”

That's so good.

I love that. He's a smart guy.

Mate, thanks so much for coming on the show.

It's been an absolute pleasure. Time flew. Thanks, pal.


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Resources / links mentioned:

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