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The Headline That Made Gary Vaynerchuk's Head Explode Entrepreneur spoke with the VaynerMedia CEO on the day of a big announcement about his brand, Empathy Wine.

By Dan Bova

Empathy Wine

"Constellation Brands Buys Gary Vaynerchuk's Empathy Wines"

That was the headline of a Wine Spectator story that ran on July 1, 2020, and as Gary Vaynerchuk told Entrepreneur, "I literally just read it like seven times, over and over. I'm just like, "What would my 16-year-old self say? I used to read Wine Spectator in science class as a junior in high school! That headline really dropped me."

As many of Vaynerchuk's followers know, in 2019, he partnered John Troutman and Nate Scherotterr, both former VaynerMedia executives, to launch the wine brand, Empathy. Sold direct-to-customer, the brand's most powerful strength, Vaynerchuk says, is how it is "massively over-delivering on quality for the $20 a bottle price point we set."

Related: Gary Vaynerchuk: Entrepreneurial Success Isn't What You Think

On the day of the sale announcement, Vaynerchuk spoke with Entrepreneur to break down the success of the brand, and to offer his thoughts on the vital things all businesses must be doing right now to survive the current economic climate. Here are some of the takeaways from that conversation.

On the fast launch and sale of Empathy Wine

"I have that family-owned-in-perpetuity DNA, so if you and I were buddies betting on it and you asked, "Do you think this will sell in five years?' I would have taken the over. I would have lost that bet. But this was a situation that I call 1 + 1 = 11. And what I mean by that is that when two parties come together and it's disproportionately impactful for both sides."

Quality is king

"I'm very passionate about Empathy becoming the greatest $20 wine in the world. And so I think what most people are going to miss out of this whole process is that we won in a very limited time not because I'm Kylie Jenner. I'm not 1/100,000th of Kylie Jenner. This is not an influencer brand. This was a brand that delivered on its promise — ridiculous quality for the price point — which consumers responded to, and a brand run by individuals that disproportionately understand marketing in 2020."

Related: 7 Game-Changing Social Media Tips From Gary Vaynerchuk

Your best business is the one you know

"I grew up in this business. I've been around wine since I was 15 years old. I was stocking shelves for my dad's liquor store and ran the business from 22 to 35, so that led to things like understanding how good the fruit is in Lodi, for example. People who do great things know the actual value of things. So they understand the arbitrage of quality versus price. I mean, if I started a fashion brand, I'd get murdered. I couldn't even begin to think about whether to spend extra on buttons — I just don't know! But there are a lot of people on this earth who know how to make a $65 shirt or blouse or jacket that I'd probably spend $290 to make, and mine would suck compared to theirs."

DTC or die

"You need to be DTC at this moment, at this second. I've been yelling about its importance for 20 years, and I think the hundreds of thousands of messages and emails I've gotten over the last hundred days is a testament to that. A lot of people are telling me they regret not listening or not executing on something they've heard out of my mouth for a long time. Those are the most difficult emails to read, just devastating. I've been listening to you for 11 years and I don't know why I didn't listen. My business was good, who could have thought of something like this could happen? And I reply that there's no crying in baseball and there's definitely no crying in business. And so let's not spend any more minutes dwelling on what you should have done, and take action now. I feel no happiness about being historically correct. I'm focused on saying, "Please now use that as a data point to get serious about it right now.'"

Related: What Gary Vaynerchuk Learned by Experimenting on Himself

It can always be better

"One of the best things that has worked for me is that I try to put myself out of business before somebody else does it. As soon as something is going well, I'm trying to think about what can be better. That can happen two minutes after we do some sort of tactic or execution, or it can be 12 years, but never sit on it and say, "Well, it's good enough.'"

Take action now

"The debating period is over. Dwelling and debating is a zero-sum game. It's like pushups — you can't read about it. You can't just wish you'd been doing them for the last six months. If you want to do something about it, let's get on the ground and do some pushups. I understand that a lot of business owners have insecurities because they did not grow up with technology, but I try to remind my fellow 40-to-50, 60-to-70-year-old entrepreneurs: You figured out much more complex things. You didn't know how to balance your checkbook either. You didn't know how to pay taxes either. You didn't know how to do a lot of things, but you figured them out. It might not come naturally, but I know that in 25 hours of watching YouTube videos and researching on Google, you'll get there. And I really want to encourage people to think about that."

Dan Bova

Entrepreneur Staff

VP of Special Projects

Dan Bova is the VP of Special Projects at He previously worked at Jimmy Kimmel Live, Maxim, and Spy magazine. His latest books for kids include This Day in History, Car and Driver's Trivia ZoneRoad & Track Crew's Big & Fast Cars, The Big Little Book of Awesome Stuff, and Wendell the Werewolf

Read his humor column This Should Be Fun if you want to feel better about yourself.

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