Helping founders and salespeople raise capital and close $100K+ deals. $1B+ in B2C sales, including a $80M record deal. Award-winning startup mentor & salesman.
When you’re selling to high-net-worth individuals:
You need to digest this fact:
- They’ve already seen everything.
- They recognize “discovery questions” instantly.
- They’ve been through every scripted framework.
- They can feel when you’re trying to extract pain instead of understanding it.
At that level, technique stops working.
Because they’re not reacting to what you say…
They’re reacting to what you are signaling.
So you don’t “fish” for their problems or try to pull answers out of them.
You declare clarity.
You tell them what’s actually going on.
You articulate their situation in a way that feels uncomfortably accurate.
You show them you’ve already solved this exact pattern for people built like them.
And all of a sudden, resistance collapses in its entirety.
Not because you “handled objections”…
But because there’s nothing left to argue with.
At that level, authority isn’t built through questions.
It’s built through recognition.
And you’re not discovering the answer with them.
You’re demonstrating you already know it.
That sells the best.
Get the exact 5-step framework I use on every cold call:
- The 5 Silent Mistakes that make your sales calls fail with serious buyers
- Nudge Theory Explained: 7 emotional drivers (use these to increase the odds of the sale)
- The Status-Play Opening - why 99% of guru-preached sales openers destroy your credibility (and what to do instead)
Grab it here:
https://t.co/ugu1B2eUbX
"I've got no idea what I'm doing" is one of the most misunderstood moments on a sales call.
First thing your rep usually thinks is "lovely, easy sale" and he's got the wrong end of the stick.
If he dives straight into pitch mode, he’d turn a buying signal into a 35-minute demo nobody asked for.
So what should he do?
Ask one simple question first: "I'm assuming this is your first time doing this?"
Then the call splits two ways.
If it is his first time, ask: "Bit of a tough one, but picture three months from now. What needs to have happened for working with us to have been the right call?"
If it isn't, ask: "What happened last time?"
Then make him fight for it: "Surely you learned from that. Why not have another crack at it yourself?"
Watch him tell your rep exactly why he can't.
But why ask awkward questions when the prospect has basically said "help me"?
Because "help me" isn't a reason to buy. A consequence is.
Think about the last time you went to the GP feeling rough.
He didn't hear "I'm not well" and start scribbling a prescription.
He asked how long it's been going on, where it hurts and what happens when you press there.
If he'd handed you pills the second you sat down, you'd walk out thinking he hadn't got a clue.
And you'd probably never take them.
Your rep is that GP. Except right now he's handing out prescriptions in the waiting room.
That's what those questions fix.
The first-timer has to describe what "better" looks like before he's sold anything.
The one who's tried before has to relive what it cost him.
Both have to say out loud why this matters, in their own words.
And the ones who can't answer were never going to buy anyway.
No consequences, no sale.
I've built sales teams past 200 people.
The best reps I ever had asked fewer questions than the worst ones. Just harder ones.
No doubt your reps will hate asking these for the first couple of weeks.
But they'll love the commission cheques after that.
@CristianXIV Great process. And I'd add that every call should end with a clear commitment from both sides.
Even if they aren't ready for a meeting, agree on what they'll review or what info they need, and when you'll reconnect. Much better than leaving it open ended.
@AlexTuccori This is why I wouldn't treat an unanswered call as a definite no. There could be a dozen reasons they didn't pick up.
Follow up and give them a clear reason to respond.
@Whalberto The best bit is that they're the ones coming up with the number.
Makes the convo feel a lot more natural than throwing numbers at them and hoping they buy into it.
@breinnermo Harder a channel is to master, the less likely everyone is to compete on it.
And that creates the opportunity for people willing to put in the work.
The best sales techniques on the planet will never save a bad fit.
Salespeople graft way harder than they ever need to.
They spend every waking hour learning how to handle objections so they can convince, argue and "trap" prospects with clever little tricks.
Trouble is, half those tricks go straight out the window the second the prospect starts pushing back.
All that time and energy would be far better spent finding prospects who:
- know they've got the problem you fix
- know it's actually a problem
- and want some bloody help with it
The secret is to keep prospecting and bin the bad fits early, not keep running headfirst into a brick wall like a muppet.
Things I’d tell my 25-year-old self about closing deals:
- Your tone will carry more weight than any perfectly written script
- Rapport isn’t built through chatter, it’s built through proof and certainty
- The prospect who challenges you the most is often the closest to saying yes
- Every call resets to zero. No history, no carryover. Treat it like a clean slate
- Conviction closes. Any trace of doubt leaks through immediately
- You don’t “find confidence” and then perform, you perform until confidence becomes unavoidable
Most of the painful lessons only look obvious in hindsight.
Get the exact 5-step framework I use on every cold call:
- The 5 Silent Mistakes that make your sales calls fail with serious buyers
- Nudge Theory Explained: 7 emotional drivers (use these to increase the odds of the sale)
- The Status-Play Opening - why 99% of guru-preached sales openers destroy your credibility (and what to do instead)
Grab it here:
https://t.co/ugu1B2eUbX
@animal Omg defo don’t take everyone. And yes, promise to ‘get it’ quicker
But it’s wrong to say not realistic or emotionally mature. Quite the opposite I’d say
In saying all of this - you NEVER know until u put a phone in their hand
Never apologize for a cold call.
Reframe it instead.
A CEO once told me, on a cold call, that he doesn't take cold calls.
I said, "Neither do I. But we're here now, aren't we? Look, I appreciate it's not the most elegant delivery. But try to look at the value being delivered, not the method.”
“What do you mean??”
“If you met Sydney Sweeney in the supermarket, you wouldn't moan that you met her next to the lettuce. You'd just be glad you met Sydney Sweeney."
He laughed.
Then I went for the throat: "Your existing advisors haven't told you about this. Which means either they don't know about it, which is shit. Or they're not telling you, which is worse. You won't read about it in the paper. And as beautiful and clever as your missus is, she probably doesn't know about it either."
He burst out laughing again.
"So give me 240 seconds and I might just change your life."
"Go on then."
Closed that afternoon.
That's why I never let my reps apologise for picking up the phone.
You can also take a rep who gets hung up on all morning, teach him to reframe the delivery, and watch him book back-to-back appointments by the afternoon.
I've watched it happen more times than I can count.
It's why reframing the call matters more than perfecting the pitch.
I've closed over £1B, most of it from cold calls.
Trust me.
The objection is never about the call. And since your reps will hear it every day, train them for it first, every time.
Apologise for the call and you're a nuisance.
Reframe it and you're the opportunity.