If you’re telling me how great you are, how you did this or that, what you own, where you’ve been…my eyes start to roll into the back of my head. That’s how you tell someone is an amateur, if they don’t stop telling you how great they are.

You’ll know this if you ever encounter those at the top. Who are typically more warm and gentle than those at the bottom. Their accomplishments speak for them. If you’re a public figure and you’re telling us what you’ve achieved, you’re just demonstrating your insecurity. You think you’re winning, but you’re not.

I know that the music business, many businesses, are based on salesmanship, but you have to know when to sell and how. If you’re a full-force bundle of energy your words bounce right off others, they stop listening. First and foremost people want to know who you are, that you’re likable, that you’re interested in them. Want someone to be your friend? Ask them questions, listen to them. And this does not only work in business, the number one complaint of women TikTok daters is the guy only talked about himself, that he didn’t ask them a single question. Doesn’t matter how good-looking they are, how much money they’ve got, they don’t want to go on another date.

If you’re telling someone you know this person or know that person to embellish your image, you’re losing. Unless asked, hold this information back. Or maybe add an anecdote about the third party that further illuminates the conversation. There’s a podcaster who can’t stop telling us that she knows this or that tech person, that she just spoke to them yesterday. I thought it was only me, but my nephew says he refuses to listen to any podcast she hosts, because she’s intolerable. And the amazing thing is she doesn’t seem to know this.

Once you’ve made it, don’t keep reminding us that you’ve done so. We know. Or we’re not worth impressing in the first place.

And you’ve got to know, how ever much money you’ve got, wherever you think you’ve been, there are people who have more and have done more… Don’t try to compete, it makes you look small. Makes you look like you play in a backwater where this works. However, don’t be a sycophant. Those who’ve achieved can smell this, and they stay away. Or lose respect. Those at the top can hear a contrary opinion more than those at the bottom, because they’ve already made it, and they know that to continue to be on top they’ve got to constantly learn, adjust and take risks. So, if you can add insight, they treasure it. If someone is shouting your opinion down, that means they’re not really in control, not really a player, they’re too uptight about their place in the firmament.

Where you went to school… Who your parents are… Especially in the music business, no one cares. It’s a fluid society wherein a CV means ever less. Sure, an Ivy League degree might help you on Wall Street, in consulting, at Procter & Gamble, but it’s actually a turn-off in the music business. Because if you bring it up it demonstrates that you think you’re better and entitled, when in truth everybody starts from the same line. Look at the music business, MBAs are scarce, certainly compared to other industries. And have respect for those who’ve been doing it. It might look easy to you, yet it’s anything but. You want to be a concert promoter. Are you familiar with building rebates? Without them you almost definitely won’t turn a profit. Don’t think you know more. Which is different from offering insight, analysis.

If you’re backstage, if you meet someone by chance, and you start telling them what you’ve achieved, they tune out, go on autopilot, ask themselves how long they have to stand there until they can move on. Oftentimes they brush you off. If the person you want to impress is silent, you’re in trouble. You may think they’re listening, but usually they’re judging, negatively.

Be secure in your achievements. And know if you’ve got none, odds are no one is interested in listening to what you have to say. And rather than go up and introduce yourself, have someone else do so, someone the object of your affection already knows, already respects.

If you meet a rock star don’t tell them how much you love their music, or maybe just employ a line, but then ask them about their hobby, what they’re interested in. If you’re that much of a fan, you know what that is. They love to wax rhapsodic on these non-music topics, because no one ever asks them about them, or cares what they really have to say about them. And ask deeper questions, to show you are listening. If you are listening you are one step ahead, then someone can see you as a friend, and they have to see you as a friend before they see you as a possible business partner.

And certainly don’t waste anybody’s time. If the big muckety-muck has been talking to you for a while, excuse them, let them off the hook, let them go. They respect this. Because you demonstrate understanding of their position. The bigger the person, the more time-challenged they are. You do not want to use up more than your allotted time. If you’re dominating the person, not letting them go, they’ll never want to talk with you again. And you’d be surprised how well people remember those who are friendly and express interest. Much more than the salesman trying to push something upon them.

So, you own a flashy car. They might own five.

You might have flown private. They own a plane. And then there was that article in the “Times” saying not to boast about your jet, because someone else might have five. Yes, there’s always someone further up the totem pole, be wary of trying to impress them with what you’ve got.

And also learn to say no. If they invite you somewhere, offer to include you, give them an out. It shows respect. If they really want you, of course you’ll come. And even though they’re rich, offer to pay, they’re never going to let you, but it shows you understand the game, they’re sick of being ripped-off, always opening their wallet. Then again, if they’re on an expense account everybody knows they’re not really paying anyway.

Learning how to interact with the rich and famous and powerful is a skill unto itself. You can learn it, but you have to be open to it. I know people who refuse to bring certain others to meetings because they won’t shut up. You don’t want to be excluded, you want to be included.

Subtlety pays dividends. Leave the boasting to the acts, but even that’s  a bad look in most cases. But if you’re behind the scenes, in business, you’ve got a career too. You want to ingratiate yourself, be a member of the club, and by selling yourself for inclusion 24/7 you’ll end up out.