Stop Waiting, Start Asking: The Bold Approach to Winning in Luxury Sales

If you don’t ask, you don’t get. That couldn't ring any truer when it comes to sales in the luxury world, high-ticket, and big-stakes deals.

In fact, you’ll find that it’s one of the biggest differences between those who "make it" in this world and those who don’t. One side takes the risk and asks, the other sits waiting.

Until they have the right connections.

Until the right doors open.

Until they have the pretty website.

Until they’re given permission.

But none of those things are going to help you not just break into this world but break into it and make it. You’ve got to be brave enough and bold enough to just ask for what it is you want.

In my first business, I knew I didn’t want to do what competitors around me were doing. I knew that I wanted to be on the luxury side of the coin AND I wanted to work with the B2B, not B2C, section. I had zero contacts, zero experience in pitching, and no website.

So I could either sit around waiting OR I could knock open the doors... I chose the latter.

I sent cold pitches to generic email addresses asking for exactly what I wanted. Out of 10 of these, I had three replies, and one ended up in a seven-figure closed contract.

I could share a million stories like this, where I dared to ask, where clients dared to ask, and by asking, got what we wanted. So if you really want to make it in this world, be bold and quit waiting.

If you don’t have connections, go get some. Yes, if you can be introduced by others, that’s awesome, but if you don’t have any connections, don’t sit waiting. Find somewhere that you can get a handful of connections yourself initially. It could be online, it could be offline, it could be at an event, or even your local golf club. Even if you think there’s no one in your current network who could help you... ask anyway. You don’t know everyone in your network and who they’re connected with. So ask.

If you see an opportunity you want in on, go ask. Once upon a time, I saw a press release about an asset sale I really wanted to be part of. I didn’t know anyone on the selling side, I had no previous experience with them, but I wanted to be part of it, and I knew I could contribute. So I found a few contact details and got pitching. The result? I didn’t get to be part of that particular asset sale, but they came to me with something much, much, much bigger just a few months later, and I did get to be part of that.

Another time, I had a client who was interested in purchasing a particular high-value asset, but they didn’t think they had the right access. Instead of waiting for an invitation, we reached out directly, navigated the right connections, and within weeks, they were sitting at the table closing the deal. That’s the power of asking.

Ask for the sale. I lose count of the number of sales coaching clients who’ve come to work with me saying they want high-ticket/big-stake sales, and yet when we get down to the nitty-gritty of "how often are they actually selling," you find the answer is very little. Because they’re waiting for permission or some other myth they’ve developed around sales. Ask for the sale. Daily. Let the world know, let your ideal clients know. You have to be asking for the sale—quit sitting, waiting for permission from the world.

If you’re serious about making it in the luxury, high-ticket, and big-stakes world, you can’t afford to sit on the sidelines waiting. The ones who win in this space aren’t necessarily the most experienced, the most connected, or the ones with the prettiest branding. They’re the ones who have the guts to ask, the confidence to put themselves in the right rooms, and the persistence to turn a "no" into a "not yet."

So, are you going to keep waiting, or are you going to start asking? If you’re ready to break into this world and start closing the kinds of deals that change everything, reach out. Let’s make it happen.