Entrepreneurial lessons from a serial entrepreneur, CEO, investor, and best-selling author

This article is part of Tech in Asia’s partnership with The Jay Kim Show where we publish the revised transcripts from the show’s podcast interviews with top entrepreneurs. This is heavily revised from the original show transcripts. For the full interview, go here.

Gary Vee is one of those natural-born entrepreneurs. He was hustling at the age of five, setting up lemonade stands, and selling baseball cards, making thousands of dollars a week. He then took his family’s wine business from three million dollars in annual revenue to 60 million dollars in just five years. Now, he runs VaynerMedia, which is one of the world’s hottest digital and social media marketing agencies.

He is also a prolific angel investor investing in companies like Facebook, Twitter, Tumblr, and Uber. He is a New York Times best-selling author of four books, popular podcaster, inspirational public speaker, and all-around entrepreneurial giant.

I’m a huge fan of Gary’s. If you know him or follow any of the content that he pumps out on a daily basis, you will know that he’s a very busy guy. He talks about the most important aspect of being an entrepreneur. He also talks about where he thinks attention will be in 2017. Let’s jump right in. Get ready for some gold.

So why don’t you just run us real quick through your story?

“I was born in the Soviet Union, so obviously a different version of communism especially in the seventies. […] We got out there luckily in the late seventies when I was a kid. We came to America. We were super poor. […] My dad used to drive from Queens to New Jersey to get paid two bucks an hour to be a stock boy in a liquor store. I was an entrepreneur from the get-go. You know lemonade stands, baseball cards, that kind of stuff. When I was 10, 11, 12, I was making hundreds of dollars, if not thousands of dollars, a weekend selling baseball cards in the malls in New Jersey. So I kind of knew I had it from a very, very, very young age.”

“My dad dragged me to the liquor store when I was 14 that he now owned. I fell in love with wine collecting and the culture of wine. I thought I could build a big business in 1996. At 21 years old, I launched one of the first ecommerce wine businesses in America. From 1998 to 2003, in that five-year window, I grew my dad’s business from a three to a 60 million dollar business using modern digital tactics, email marketing, ecommerce, Google AdWords, and blogger outreach. YouTube came along and I started a wine show. That was right around the time Twitter and Facebook were doing their thing as well. I used those platforms to build my brand and became an investor in Facebook, Twitter, and Tumblr.”

“In my entire high school career, I got four A’s, all in gym. I was far from a scholar. I think that it was tough. I went from being my own boss making US$800 a weekend, US$1,400 a weekend, to making US$30 a weekend, bagging ice for 15 hours a day in a liquor store. At the same token, I just kind of wanted to support my family’s thing, and was willing to pay my dues, and was thankful for my parents for coming to this country. Even at that age, I knew what they did was special and wanted to support our thing.”

“When I realized that I didn’t want to sell beer and liquor, but realized there was a culture around wine and wine collecting, I saw the storytelling, I saw the creativity. I saw the marketing and I really ran with that.”

So you go from there and now you’re an investor and you’re running a multi-million dollar digital marketing agency. How do you manage?

“By realizing there’s no option, right? I’ve made my bed, now I have to sleep in it.”

“You know what the real answer is? Because I want to. How do I stay current? Because I want to. Like when you want to do anything, you figure it out. You’re giving up something else because I’m not watching this, or playing that, or meeting this, or doing that. So I do what I want to.”

“I want to watch the New York Jets every weekend, and so I do that. That takes out of family time and it takes out of business time, but that’s my escapism; that’s my release point. I want to see my family more and so now, starting this fall, I’ve cut out Friday nights, which used to be very, very effective for me. It’s a time where I’d get four to six hours of meetings that I couldn’t fit in the rest of the week gone. That will mean less business results because I want to see Meisha, Zander, and Lizzy more. It’s choices, right? How am I current and how am I at the forefront? Because I want to be.”

You are a born entrepreneur. Some people are like that. Can entrepreneurs be made so to speak?

“Not all basketball players are born LeBron, Carmelo, and Durant, right? I definitely believe that I was gifted more on the entrepreneurial upside than most people, no question. I mean, I just don’t know what else to say. […] It’s not ego, it’s 35 years of history. I sold more lemonade than everybody, I made more money on baseball cards than everybody, I built a bigger liquor store than everybody, and I built a personal brand bigger than most. I’ve, in four minutes, built one of the biggest social digital agencies and in the most competitive space. I’ve done it, so yeah I’ve got it.”

“Everybody’s got a cap. I think my cap is multi-billions. I think other people’s caps are several hundreds of thousands. [What’s better?] Making US$187,000 a year as an executive and not being that happy, or making a buck twenty-seven as an entrepreneur and being super happy? That’s an interesting debate. […] What’s the happiness line versus the money line? I think all of us have different lines. I leave lots of money on the table for happiness every day, and other people do as well. So yes, I do not think that all entrepreneurs are built equally.”

There’s a lot of weird stuff going on in the online space. What are you most afraid of right now when you see these guys on Instagram, flashing dollars, and actually making money off of it?

Why don’t you tell us where you think the attention will be in 2017?

What is the single most important trait to become a successful entrepreneur?