“Fear in business has never been a variable for me, and here’s why…”

Gary Vaynerchuk is a social media superstar, entrepreneurial phenom, and all-around good guy. And given that the world is going though somewhat of a funk these days (what with the global pandemic and all), we thought we’d get his take on a few things.

We sat down with GaryVee as part of the Esquire Q&A Podcast series, where we get to talk to some of the brightest minds on the planet.

This week, we wanted to know a bit more about how Vaynerchuk is handling his business during the pandemic, what advice he would give to those who have just started a business in 2020, as well as why fear in business is just counterproductive.

You can watch/listen to the whole podcast right here (and you can read a transcript of our favourite part below).



When it comes to business, people need to have a better relationship with fear and losing.

In general, people need to recalibrate it in their minds. I am not saying that because we are currently in an extremely challenging time, but it is something I have always believed in.

It is important for people to understand the risks that come with running a business, and should be wary of them. That said, by its very nature, a risk can have a potentially huge upside.

Over time I have become thoughtful enough to know when an investment has a good chance of succeeding or not.

An element of risk doesn’t put me off. In fact, it makes it more curious. I have a desire to try to taste it, to genuinely see it through—I am too curious to stop. Where the difference comes is that I feel no shame in that.

Even if something does fail, I get to use that knowledge and get to use it when I play again.  Here are a few examples from my own life.

Corked, my 2009 wine social media network failed. However, I always knew that it might do. I wasn’t running the business myself, and therefore there was a bigger element of risk. I bought it, and hired somebody else to run it because I was stretched too thin at the time with other ventures. I was aware that it might not work, and would lose me money. And that’s what happened.

I bought something called Lost Letterman— a sports media website which failed when I tried to integrate it into VaynerMedia years ago— but I wasn’t concerned about it because I learned  a lot of lessons from it  that ultimately led to  the acquisition of  PureWow.com that allowed me to start building a true media conglomerate.

VaynerLive and VaynerEvents failed twice. But I learnt a lot about live event marketing, and feel very confident now that  if (and when) I get into it  I will be in a good place.

Each of those were six- or seven-figure losses, but they didn’t put me out of business. Instead they taught me quite a bit.

It’s important to note that I have never done anything in business with the consequence that if it were to fail, I would have to remarkably change my lifestyle, or sell my home. But fear in business has never been a variable for me because I have never been scared to be humble. To humbly accept defeat, rather than blinding ploughing more time and effort into something that isn’t going to work, is one of the secrets to my success.

The truth is that things don’t always work out, but my experience has taught me to identify when I am in a potentially losing situation and embrace it.

A lot of people don’t take risks, or are fearful in business because they put too much stock in external opinions, worrying more about what everyone else will think about their wins or losses. I have an easy remedy for that; I put all the cheering and booing in the same pile.

It’s not positive or negative feedback, it’s just feedback. The trick is to not let it stop you from focusing on the goal.

So if you are afraid to take a risk based on what other people might think of you, don’t be.


Subscribe on YouTube

Esquire now has a newsletter – sign up to get it sent straight to your inbox.

Want up-to-the-minute entertainment news and features? Just hit ‘Like’ on our Esquire Facebook page and ‘Follow’ on our @esquiremiddleeast Instagram and Twitter account.

RELATED CONTENT