GaryVee is a serial entrepreneur, serving as the Chairman of VaynerX and CEO of VaynerMedia. He’s built his career recognizing what’s up-and-coming in culture. And it all started in 1998 – when he pivoted his father’s liquor store into one of the world’s premier alcohol e-commerce platforms.

Today, GaryVee helps brands leverage consumer attention through his full-service advertising agency, VaynerMedia. And he acts as a prolific angel investor with companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber on his portfolio.

But his personal brand is where he gets the most attention. Its straightforward, no-bull style has made him one of the most famous faces on the internet (with over 3M subscribers on YouTube alone).

A few weeks back, we sat down with GaryVee at Playbook 2021, this year’s biggest event in small business, for a candid Q+A on what the most successful startups all have in common. And in typical GaryVee fashion, his answers were insightful, direct, and cutting edge.  

👉 Want to watch the full interview? You can access all the Playbook 2021 sessions, including this one, on-demand now. Get the replays.

1. They’ve built their brand

As far as GaryVee is concerned, building your brand is everything. But he doesn’t just mean growing your follower count. He means creating content that provides real value and draws awareness around your expertise in your niche.

To do this, GaryVee advises the companies he works with to consistently publish content on social media and establish their online presence. But most people don’t want to put in the work it takes to be consistent.  

“People want to stop at the point that’s convenient for them,” GaryVee shared. “[Building a brand online] is real, actual work. And for some reason, people genuinely want to find a way out of it.”

But it’s one of the few things in life where there’s only one way to do it. You need to create a lot of content, publish on a predictable schedule, and engage with followers in the comments.

And it’s not going to happen overnight. GaryVee started building his YouTube following in 2007, almost 15 years ago. Since then, he’s posted a new video to the platform every Monday, Wednesday, and Friday, collecting nearly 300M views across them all.

But he doesn’t put all his attention on one platform. He also posts on LinkedIn, Twitter, and Instagram daily (sometimes even multiples times a day).

And if you’re just starting to build your brand on social, GaryVee suggests focusing on a mature and unexpected platform: LinkedIn. In his opinion, most people are using the platform all wrong, leaving the biggest opportunity to get it right.

“People use LinkedIn as a sales spam channel instead of a content channel,” he explained. And that means if you use the platform correctly and publish quality content, your brand will stand out among the rest.

In other words, stop using LinkedIn to send templated messages and react to other people’s content. Instead, use LinkedIn like GaryVee. Meaning, publish articles, share videos, and start thoughtful conversations. On GaryVee’s LinkedIn, you can find a daily question, quote, or article that prompts his network to engage, keeping him top-of-mind.

Admittedly, when you post this much, you run the risk of contributing to the noise. So, to determine which posts are signals worth sending out, GaryVee reverse engineers who he is online.

In other words, he starts with the end goal first (to establish himself as an expert in his industry and personal interests) and works backward. Then, every time he posts or leaves a comment, he crafts the content to contribute to that end goal.

“People who run a company genuinely need to ask themselves if they’re up for posting on social consistently. And there’s nothing wrong with not being up for it, but that’s what it takes to build a brand.”
<blockquoteauthor>Gary Vaynerchuk, VaynerMedia<blockquoteauthor>

2. Their culture thrives off candor

If building your brand is the top priority, nurturing a culture built on honesty, openness, and vulnerability is a close second. Because, according to GaryVee, candor is a vital ingredient to every company culture.

“The first hundred people need to be pure entrepreneurship, pure family, pure fire, and pure offense,” GaryVee explained. They’ve got to be equally passionate about the startup. And they need to know where they stand with you (from honest, open conversations).

That way, everyone on your team genuinely believes in your company’s mission. And they know what you expect of them and what challenges might be coming next. As a result, employees are more invested, more productive, and more willing to learn along the way.

“When an organization has a ton of politics, everyone’s slow because they’re thinking about every move,” GaryVee told us. But when you incorporate candor or openness, your employees are more likely to move fast and break things (and that’s how you learn to really run your business).

In his most recent book, Twelve And A Half, GaryVee dives deeper into how candor can benefit your business. But it wasn’t until recently that GaryVee realized it was his (and most business leaders’) greatest weakness.

“I realized [recently that] my lack of candor was creating [a culture of] fear because people didn’t know where they stood. I could high-five you Friday and by Monday call you into the office to say you’re out,” GaryVee admitted to us.

But now, GaryVee focuses on laying it all out on the line. He gives honest feedback to everyone on his team, even when it toes the line with criticism. He openly shares the upcoming challenges his team might face. And he’s focused on doing everything with empathy by understanding his employees’ perspectives and situations before initiating each interaction.

“Now that I’m focused on candor, my team has even more confidence in me. They feel safer with me. And we’re having more fruitful conversations.”

In fact, GaryVee believes business as a whole needs a rebrand that focuses on bringing kindness and compassion back into the workplace. He says most CEOs are driven by ego, which causes their team to work from a place of fear.

GaryVee challenges you, as a business leader, to put ego on the back burner and have confidence in your team. Meaning, drop any harsh management practices. And focus on making your employees feel safe by encouraging biased action and making mistakes. “You should always go softer in a world that goes harder,” he shared.

3. Efficiency is a top priority

GaryVee is a big believer in executing quickly, breaking things, and eliminating what doesn’t work or doesn’t matter. And this applies to every aspect of his business.

“When people say they don’t have time, I tell them: trust me, you do,” he explained. “It’s just that you’re not spending your time on smart stuff.” But that’s not to say that finding efficiency is easy. It’s a never-ending challenge.

“I am incredibly efficient. I have three full-time admins and a chief-of-staff. Yet every day when I go to sleep, I can think of 75 minutes of my day that made no sense,” GaryVee shared. And that’s after he cut hour-long meetings down to 30 minutes and half-hour meetings down to 15 minutes.

But efficiency doesn’t just mean protecting your time. It also means protecting your team’s time. One way to do this is by only having the most essential players at each meeting. So, for example, you don’t need your CEO and CMO in the same meeting about upcoming campaigns – just your CMO. That way, you can shave hours of wasted time across the company.

Another way he suggests is by taking the current labor market (where finding and keeping great candidates is difficult) at face value. According to GaryVee, business leaders need to “hire fast. Fire faster. Promote fastest.”

Because the reality is you’re taking a gamble every time you hire someone new. So, when you find someone you think is a great culture fit, bring that person on.

That way, you can get them in the trenches and see how they actually work. If it’s not a good match, admit your mistake and correct it by offboarding them immediately. Just be sure to do it with kindness, compassion, and empathy.

“Hiring is guessing. Even with an emotional radar as my superpower, the amount of times I’ve hired poorly is insane.”

4. They know the value of “and”

Most businesses look at decisions like this or that. But in most cases, they’re this and that. Per GaryVee, “[this need to settle] is our biggest problem in society right now. People are obsessed with ‘or.’ They ask themselves blue or red? But what about ‘and?’ What’s wrong with purple?”

By the time you’re choosing between two options, both should be fully vetted. And you should have the data showing that either would be a sound business decision.

For example, you may wonder if you should publish content as yourself or your business. Both would help build aspects of your brand. Really, business leaders should be doing both because people typically do business with people – not just the company. But they also want to know the company is legit.

“Every time you think you’re making a decision of or, challenge yourself to figure out if it could be a situation of and. If everybody does this one thing, it will change your business.”

The only exception to the “and” rule is when you don’t have the resources to do both. At that point, it’s a 50/50 shot at success (after all, you already vetted both options). So, according to GaryVee, “you might as well flip a coin because you don’t know what’s going to happen [after you implement that decision].”

This all gets us back to making efficiency a priority. Once you have your decision, go all-in on it immediately and invest all your effort into making it work. If and when it starts to break, then try the other option. That way, you waste little time making decisions and quickly learn what works and what doesn’t.

🔥 Tip: Document what worked and why, so your teams aren’t just reliving the same episode. Trainual puts all this documentation in one place, so your team can easily access it moving forward. Try for free.

5. Gratitude is their greatest motivator

What stands out most about GaryVee’s list of things that successful startups share is that most successful people, in general, share them as well. Perhaps the most obvious example is this last one. In GaryVee’s experience (first-hand and second-hand), gratitude is the ultimate driver of success.

“It’s not about money for me. Gratitude is actually the driver of GaryVee,” he shared. “I want to put out content because I’m grateful to my [entrepreneurial] community.”

To show that gratitude, GaryVee often shares his valuable insights with everyone on the internet. And, as a result, he helps more people and reaches more prospects.

“People don’t share [their knowledge] because they think they’ll help their competitors,” GaryVee resolved. “But no competitors are taking from me.” Even if someone takes his idea as their own and secures customers with those ideas, that’s still a win in his book because it’s proof that he’s the leading expert.

And as that expert, GaryVee believes he has enough knowledge and experience to share with everyone – even his competitors – without losing his advantage in the marketplace.

For example, he shares the same advice his media clients pay for on YouTube and LinkedIn for free. And he gets great engagement and viewership as a result (his posts regularly get thousands of views and comments, regardless of platform).

But being willing to do all this comes down to one crucial thing: mindset. Because at the end of the day, GaryVee believes success is a game of confidence, patience, and accountability. And when you operate from the mindset that you’re responsible for results, the ball stays in your court.

‍If there’s one online influencer who’s known for giving blunt business advice, it’s Gary Vaynerchuk – perhaps, better known as GaryVee.