Gary Vaynerchuk’s 5 Essential Secrets of Success

Gary Vaynerchuk, the unusually outspoken and forthcoming entrepreneurial sensei, would love to be your mentor, at least in a virtual sense.

He’s built a career out of serving up no-nonsense advice, and the man is on a wicked roll right now.

His advertising and social media consultancy, VaynerMedia, is growing at hyperspeed. He just launched a sports agency and a tech investment fund, and he’s about to cohost a new Shark Tank-inspired reality show for Apple called Planet of the Apps.

Meanwhile, his #DailyVee and #AskGaryVee shows on YouTube have nearly 500,000 subscribers, and he still makes time to write, give talks, and occasionally reprise his role on Wine Library TV — one of the earliest YouTube success stories.

Sound like a guy you’d like to follow around for a while?

I did, shadowing Vaynerchuk for several days. I watched him make a TV appearance in New York, eavesdropped on meetings with clients, chatted up his staff, and tried to keep up as he navigated the insanity of the Consumer Electronics Show in Vegas with steely focus.

It didn’t take long for me to see why he’s so successful.

Here are five of Gary Vaynerchuk’s secrets that you can apply to your business today.

Secret #1: To find the most creative solution, look at the problem from different altitudes

Vaynerchuk constantly encourages his team to “bend the lines” around a problem — in other words, change the way they’re looking at it to expand the range of possible remedies.

“You can tinker with the parameters in ways people didn’t think were possible,” he says.

For example, if you’re decorating a room, you don’t just look at paint samples and shop for lamps. You also ask whether you need walls in the first place. I saw him execute this with clients, and their faces brightened the minute they realized other routes could lead to strategic solutions.

Secret #2: Being brutally honest about what’s possible will help you achieve the seemingly impossible

There are times when expectations are patently unachievable. “People often get caught up trying to solve a problem that they absolutely 100 percent cannot solve,” Vaynerchuk says. “So you have to defuse the chance of failure by using the truth. Just say there’s no way to achieve it.”

At the wine store years ago, Vaynerchuk’s father thought he could sell 1,000 cases of a specific wine in one month. “I said it was impossible,” he says, “that we could at most move 480 cases in two months.”

The dose of reality helped the company focus on what was actually possible, even with the aggressive new marketing and sales tactics Vaynerchuk had introduced — and as a result, grow annual revenue from $1 million to $50 million in six years.

Ready to improve your habits and level up your life? Download our FREE Ultimate Guide To Habits below.

When you signup, I'm also going to send you my newsletter full of my best money advice for free.

Secret #3: The best answer is often a question

Watch enough episodes of #AskGaryVee and you’ll start to see a pattern in his approach to answering questions, one I saw him deploy repeatedly with his staff and clients.

He cuts straight to the heart of the question and what it says about the asker — their motivations, their fundamental assumptions, and what their real question should actually be.

When a viewer asks, say, why his social media strategy isn’t working, Vaynerchuk might respond with, “How do you know it’s not working?” or “Do the conventional rules of social media marketing apply in your case?”

This is something Vaynerchuk has taken to more consciously: He recently converted the show to a call-in format, which allows him to more precisely unpack the viewer’s question and get to its real core.

He has seemingly pitch-perfect judgment — something that’s difficult to conjure up on your own, of course. But you can hone your ability to dig deeper into the specific challenges facing a client or employee and suss out the real problem.

Secret #4: The most successful companies, old or new, think like startups

Many of Vaynerchuk’s clients are large, established companies — Toyota, Nike, General Electric — with long histories, rather than the scrappy startups you’d think would gravitate to him. But once you get to know him, this makes sense. He has a unique ability to leverage innovative solutions to solve legacy problems.

“We’re one of the most valuable brands in the world, but he taught us how to behave like a startup,” says Linda Boff, GE’s chief marketing officer. “Gary and his team were really essential in helping us think through the right way to behave on social media — in short, to act as a person would, rather than a company.”

Learn from the experienced masters, Vaynerchuk exhorts, but maintain an upstart’s enthusiasm and open-mindedness.

Secret #5: The best leaders know when to fool their employees

One of Vaynerchuk’s most consistently impactful leadership strategies is to instill in his employees a presumption of success.

“Sometimes tricking people into thinking they’re better than they are — by building up their self-esteem — can work wonders,” he says. “I’m an HR-driven CEO, and while we don’t know a lot about the brain, we do know that a funny thing happens when you actually think you can do something. So I rule with positivity.”

A quick spin through VaynerMedia’s office validates this completely. His employees look happy, engaged, and thoroughly inspired to succeed.

Want to capture the same kind of energy? Head to YouTube. Your mentor is waiting.

Ready to take control of your finances (without tedious budgeting?) Get the first chapter of Ramit Sethi's NYT Bestselling Book below.

When you signup, I'm also going to send you my newsletter full of my best money advice for free.