How Jimmy ‘Velvet Suit’ Valentine Taught Me the Secret to Selling to the Rich

The first rule of selling to the ultra-wealthy? Don’t get caught selling. The affluent are hypersensitive to hard pitches and overt marketing—they can sniff out desperation like sharks smell blood in the water. If your strategy is too obvious, you’ve already lost.

In today’s episode, I take you behind the scenes of selling to the 1% with a story about one of my most unforgettable clients: Jimmy “Velvet Suit” Valentine. Picture this: a serial entrepreneur with a flair for the dramatic, striding into rooms in bespoke velvet blazers that shimmered like a Technicolor dream. Jimmy was the king of big ideas, some brilliant, others…well, let’s just say luxury dog spas weren’t his finest moment.

What Jimmy lacked in restraint, he made up for in confidence—and he gave me a front-row seat to the real way the rich make decisions. Spoiler alert: it’s all about subtlety, influence, and making them feel like the idea was theirs all along.

In This Episode, You’ll Discover:

• Why the ultra-wealthy hate obvious sales pitches.
• How to plant an idea so seamlessly, they’ll think it’s their own.
• The biggest mistakes salespeople make when targeting affluent clients.
• How Jimmy’s velvet-suited confidence both inspired and taught me what NOT to do.

If you’ve ever wondered how to crack the code on selling to the elite—or just want to hear about Jimmy’s colorful escapades—you won’t want to miss this one.

Click play and find out how to sell without selling!

Luxury isn’t just about products; it’s about the emotions they evoke. The dream of exclusivity isn’t about practicality—it’s about power, status, and the intoxicating feeling of being untouchable. A luxury home isn’t just a place to live; it’s a symbol, a stage, and a declaration of "I’ve arrived."

In this episode, we delve into the psychology behind selling luxury and how exclusivity fuels desire. From terraces with million-dollar views to the subtle art of making a product feel unattainable, we’ll uncover what truly drives people to pursue the extraordinary.

We discuss:

• Why exclusivity is the ultimate selling point in the luxury market.
• How emotions, not practicality, drive high-end purchases.
• Strategies to create irresistible allure around your luxury offerings.
• The role of symbolism in selling dreams of wealth and status.

Whether you’re marketing high-end real estate, luxury goods, or premium services, this episode is a masterclass in crafting desire and selling the unsellable.

Tune in now to learn how to make your clients feel untouchable—and willing to pay for it.

Benny, a financial savant who sees spreadsheets as poetry, has a simple philosophy: money is logical; people are not. But in the world of luxury marketing and wealth management, understanding people—messy, emotional, and unpredictable as they are—is just as critical as understanding numbers.

In this episode, we unpack the nuanced reality of the wealthy: how they differ from the rest of us in lifestyle, yet share the same emotional undercurrents that drive decision-making. Benny’s struggle with the human side of wealth offers a lens into the challenges of serving affluent clients who often defy logical expectations.

We explore:

• Why the wealthy aren’t as “different” as you might think—and how they are.
• The emotional factors that influence big-ticket decisions.
• How to bridge the gap between financial precision and human unpredictability.
• Lessons from Benny’s approach to numbers—and his blind spots with people.

If you’re in the business of selling to or serving affluent clients, this episode will give you the insights you need to navigate their world with both strategy and empathy.

Listen now to discover the human side of wealth and what it means for your business.

Meet "Velvet Vicky," the unstoppable force of luxury real estate whose presence is as commanding as her sales pitch. From her Gucci tote to her air of unshakable confidence, Vicky Strauss built an empire selling fantasies. But what happens when the fantasies stop selling?

In this episode, we peel back the layers of Vicky’s approach to marketing the extraordinary and how even the most dazzling personal brands face challenges in today’s competitive luxury market. With her signature boldness, Vicky tasked me with one mission: to make her a legend.

We explore:

• How personal branding fuels the art of selling dreams.
• The secret to transforming real estate into irresistible fantasies.
• What to do when your tried-and-true strategies stop working.
• Why energy, charm, and exclusivity are non-negotiable in luxury markets.

If you’re navigating the high-stakes world of selling to the affluent—or just want to learn how to stand out in your own field—this episode will inspire and challenge you.

Tune in now to discover what it takes to reignite the dream machine and turn problems into profits.

In this episode, we dive into the fascinating challenge of marketing to the unsellable elite. Meet "Banker Benny," a billionaire whose tailored suit could pay off a year of mortgages but whose presence in a room full of millionaires was shockingly forgettable.

From his glass-and-chrome fortress on the 52nd floor, Benny reveals a critical issue facing high-level financial services: the invisibility crisis. As the ultra-luxury boutiques swoop in with their bespoke personal touch and mega-brands dominate the top tiers, where does that leave the "middle-ground" billionaires trying to stay relevant?

We explore:

• Why even billionaires need a strong personal brand.
• The war between bespoke boutiques and corporate powerhouses.
• How to craft a message that resonates with the world’s wealthiest clients.

This episode is packed with insights into breaking through the noise, building exclusivity, and standing out in the crowded marketplace of the ultra-affluent. Whether you’re in luxury real estate, financial services, or high-end consulting, this is a conversation you can’t afford to miss.

Subscribe now to learn how to sell dreams to those who seem unsellable.

Are you ready to stop selling like a door-to-door salesman and start selling like the VIP concierge of your dreams? Buckle up—it’s time to ditch the dull sales talk and embrace the glitz, glamour, and (let’s face it) ridiculous quirks of marketing to the ultra-wealthy.

In this first episode of The Velvet Rope Playbook, we roll out the red carpet and dive into:

• What’s Behind the Velvet Rope: Is it a literal barrier? A metaphor for exclusivity? Or just the place where all the champagne is? (Hint: It’s all three.)
• Our Backstage Pass: A sneak peek into how our host became the go-to marketing maven for the rich and fabulous. Spoiler alert: It wasn’t by clipping coupons.
• The Secret Sauce: Why exclusivity works, how to wield it, and why you definitely shouldn’t try selling yachts with memes.

What You’ll Learn (and Laugh About):

• How to use exclusivity like a velvet-clad ninja (yes, that’s a thing).
• The weird and wonderful psychology of wealthy buyers—because they’re not like everyone else, and that’s kind of the point.
• Why selling luxury doesn’t mean sucking up—it means showing up as someone they actually want to deal with.

Get In on the Action:

Got a crazy story about selling to the wealthy? Or just dying to know why your marketing strategy isn’t working? Send a message, and don’t forget to hit subscribe.

Let’s pop some champagne, crank up the charm, and have some fun while we master the fine art of selling luxury. After all, behind every velvet rope is where the magic happens. Cheers!