I am a salesman through and through. It’s not just what I do; it’s who I am. Sales is deeply ingrained in my DNA, a part of me since childhood.
Let me share a quick story to illustrate just how early this started…
Growing up on Teaberry Drive, we had the most wonderful neighbors – a retired couple with no children, living in a cozy ranch house right next to our townhouse. Their yard was always bursting with beautiful flowers. One day, at the tender age of five, an entrepreneurial idea sparked in my mind. I ventured into their garden, carefully plucked a handful of their vibrant blooms, bundled them together, and tidied them up a bit.
With my makeshift bouquet in hand, I confidently walked up to their front door, rang the bell, and with all the sincerity a five-year-old could muster, asked, “Would you like to buy some of these flowers?”
To my delight, they agreed to “buy” their own flowers back from me for a nickel. That five cents felt like an absolute fortune to me at the time. Fueled by this early success, the rest of that summer was spent scouring the neighborhood, “harvesting” flowers from various yards, and attempting to resell them to their rightful owners.
As I got a bit older, my sales arena shifted from flowers to baseball cards. Every weekend, I’d set up shop at trade shows, my eyes keenly observing passersby, constantly strategizing how to make my booth more appealing and stand out from the competition. By the time I was 13 or 14, I was pulling in thousands of dollars each weekend.
Even now, as the CEO of a company generating over $150 million annually, I still find myself drawn to garage sales on my weekends off. I love the thrill of discovering random items and flipping them on eBay.
Gary Vaynerchuk trash talking, highlighting his competitive and playful nature.
It’s not about the money; it’s the sheer love of the game.
Sales has been the cornerstone of my entire career. It’s the engine that powered the growth of my family’s liquor store and the force behind the expansion of my agency, VaynerMedia.
Understanding how to sell is the fundamental bedrock of any successful business.
Here’s a deeper dive into why I am so passionate about sales, coupled with some key mindset shifts that can help you become a more effective salesperson in the long run:
Sales is a Blast When You’re Passionate About Your Product
Selling shouldn’t be a daunting task.
What truly becomes challenging is attempting to sell something you lack belief in.
For me, sales is genuinely enjoyable. Whether it’s Vayner4Ds tickets, books, conference passes, VaynerMedia’s services for major corporations, or even sneakers, I dive in with enthusiasm.
However, when you’re pushing a product or service you don’t personally endorse, the process becomes significantly more uphill. I’ve been in countless meetings where it’s palpable that the person pitching isn’t truly convinced by what they’re selling – and it’s immediately evident. These individuals unconsciously undermine their own pitches with hesitation and lack of conviction, drastically diminishing their chances of securing clients.
Before I ever started discussing wine or launching WineLibraryTV, I dedicated considerable time to learning everything I could about wine. I needed to have genuine faith in what we were offering.
At Wine Library, our core belief was that we offered exceptional wines at prices lower than our competitors. We were providing real value and better deals to our customers. This conviction was a key factor in my aggressive sales approach, particularly through platforms like Google AdWords when it was still an underutilized and cost-effective marketing tool.
More recently, I ventured into creating another wine venture, Empathy Wines.
In a live stream on my birthday, reminiscent of a QVC-style call-in show, I engaged directly with people, answering their questions and selling Empathy Wines packages. My deep belief in Empathy Wines stems from our commitment to producing high-quality wine, comparable to $40 bottles, but making it accessible at a $20 price point – democratizing great wine for those without extravagant budgets.
It’s fundamentally easier, and far more rewarding, to sell when you are genuinely passionate and believe in the value of what you’re offering.
Branding: The Long-Game Sales Superpower
Some might misinterpret my advocacy for giving away free content as being anti-sales. However, the reality is that effective brand building is the most potent sales strategy in existence.
This is why, despite engaging in direct sales at times, my primary focus is to minimize it as much as possible.
My overarching goal is to cultivate long-term relationships. Anyone can achieve fleeting fame or amass a temporary following for a quick sale. But building a sustainable brand and nurturing enduring relationships with your audience over years – that’s a far more valuable and lasting achievement.
Whether you are a burgeoning small business or a massive multinational corporation, adopting a mindset that prioritizes business as a long-term relationship, rather than isolated transactions, is crucial.
For small businesses operating with limited resources, short-term sales metrics often take precedence. The immediate need for revenue can overshadow long-term branding efforts. I genuinely understand and empathize with this pressure.
However, the remarkable truth about brand building is this: a robust brand will consistently outperform any individual salesperson, any day of the week.
Ask Boldly, Expect Nothing: The Art of Detached Selling
Sales isn’t about aggressive tactics or forcing a “no” into a “yes.” True sales mastery lies in confidently asking, but remaining completely detached from the outcome, harboring zero expectations about the response.
It’s about making the offer, not about being pushy – a common misconception.
While I actively promote wine, sneakers, and books, my approach is rooted in offering these products to those who genuinely have an interest in them. I have no desire to persuade someone to buy if it doesn’t align with their needs or desires.
I am comfortable and confident in making the ask, but I operate without expectation. This detachment is a critical element in effective selling.
One of the most frequently overlooked aspects of sales is the reality that you cannot force a sale on someone who is fundamentally not interested or in need of your product or service. When I analyze why some individuals or businesses struggle in sales, it often boils down to self-imposed mental barriers. They might be overly fixated on partnering with a “prestige” brand or targeting a specific high-profile CEO.
The reality is, the business world doesn’t operate in such a romanticized or idealized manner. There are countless reasons why a particular company or executive might not choose to work with you, even if your offering is demonstrably superior to the competition.
They might be bound by long-term contracts with existing vendors.
They could have deeply entrenched relationships with competitors, or perhaps company investors have predetermined agendas influencing their decisions.
Naturally, VaynerMedia aspires to collaborate with every Fortune 100 company. However, market dynamics and intricate internal politics make this aspiration far more complex to achieve in practice. A pragmatic approach to sales is essential. You must be receptive to the opportunities that are immediately available.
I enter every business meeting with genuine optimism, believing there’s a strong possibility the other party will become a client. However, if I sense that a deal isn’t going to materialize, I mentally disengage and move on without dwelling on it. There’s no room for sentimentality in sales.
The same principle applies to Empathy Wines and my sneaker ventures. Countless individuals have built million-dollar businesses based on my advice and content, yet many haven’t purchased a single case of Empathy Wines or a pair of my sneakers. And honestly? It doesn’t bother me in the slightest.
I understand that many of them might not be regular wine or sneaker consumers, so there’s no point in trying to force a sale. For those who do purchase these types of products, there could be various other factors influencing their purchasing decisions.
Regardless of sales outcomes, I remain committed to consistently providing free, valuable content.
While I advocate for freely distributing content, let there be no misunderstanding – I am fundamentally a salesman at heart. This sales-centric perspective is precisely why I urge businesses to prioritize brand building from their inception.
Building a strong brand is unequivocally the most effective way to drive sales success over the long haul.
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