Diary / Justbobbi / Sep 26, 2022

Talking with Gary Vee

Written by: Sara Bliss

If you haven’t had a chance to experience Gary Vaynerchuk, AKA Gary Vee, immediately go and listen to his podcast The Gary Vaynerchuk Audio Experience, check out his online Q&A show #AskGaryVee, or watch him on YouTube. His musings on life, happiness, failure, and how to succeed in business are riveting thanks to a combination of his no bullshit, tell-it-like-it-is perspective, digital marketing wizardry, and out-of-the-box approach to achieving success. The co-founder of VaynerMedia, a full-service digital agency and publishing company and VaynerSports, not to mention sneaker designer for K-Swiss, Gary is on the move. He stopped for a bit to talk about what leads to happy, what mistakes most people are making, and why patience is the key.

Big Break:

There’s three parts to my start: One is the earliest lemonade stands and baseball cards—I was a natural entrepreneur. Number two was being dragged into my Dad’s liquor store at 14 and learning the craft of the wine and spirits business, and taking it from a three to a sixty-million-dollar business during my eight-year run there. It was a combination of taking the business into E-commerce, launching a website, and a really start marketing strategy that had a mix of digital, traditional, direct mail, email and Google AdWords. Number three was me starting a YouTube show in 2006 which really took off and opened up my imagination to what was possible on the internet. That led me down a rabbit hole of investing in Facebook and Twitter, and writing books about opportunities, and speaking, and ultimately leading to me building Vayner Media with my brother A.J.

Current Mantra:

Give more than you take. I think that leads to happy. I like the mental leverage of having relationships where I’m providing more than I am asking for. I think a lot of people give with expectation. I don’t. I think my parents really raised me well and put me in a great mental position. I just watched them never ask for anything and never complain. That really set the tone.


I am driven by ambition for my legacy and this mix between gratitude and guilt. I worked for everything I had. I’ve given up a lot of leisure and a lot of things people are attracted to, but its made me happy because I love the process more than the stuff.


I am far more attracted to the stories that are not covered. I have the luxury of getting 100 to 150 DMs and emails a day, so I am getting some stories that are pretty intense. I am inspired by people who email me that they are terminally ill, but steadfast on producing content to inspire and help people. I am inspired by the everyday person who is dealing with a ton of adversity and has the ability to employ optimism in a situation that the masses would deem as extremely difficult. I am fascinated by the world where some people complain about being out of skim milk at their favorite coffee shop and others who have lost their child are optimistic.

Strength training:

What makes me mentally strong is my upbringing for sure. I think when you are an immigrant and a terrible student, the world tells you that you are a loser. I actually think if you have love in the house and a support system around you, then that is an incredibly good thing to happen to you because you are dealing with adversity really early on which doesn’t make it scary. I am so comfortable in losing and I think most parents coddle their children and try to keep them from losing and creating fake victories which doesn’t prepare kids for adversity. What makes me physically strong is every day my daily workout regimen. I work out for an hour and Jordan, my trainer, makes sure I put in the work. The mental part I put in very early in my life and the physical I put in much later, but both are awfully rewarding.

Beauty from the inside out:

I am a big vegetable eater so that has really helped me. I don’t have any extreme diet, but I try to stay disciplined on that. I am extremely strong at keeping things in perspective. My life is very binary. I woke up this morning and the six or seven people I love the most are still alive and that puts me in a good mood. I deal with a lot of stress and headaches every day, but I am able to put them into work vs real life. I think I over excel in consistent, disciplined, thoughtful perspective, and that keeps me healthy, because it keeps me very happy.

Best advice:

To me it is have patience. If anything has stood out over the last decade, is that too many people are impatient which is leading to short term behavior which creates the vulnerability which doesn’t allow them to achieve what they are looking for. For me, patience really matters. Life is much longer than people realize. For me it is macro patience and micro speed, meaning work hard and fast day in and day out, but at the highest level be patient with your actions and understand what you are trying to achieve. It is unbelievable how many people are being defeated by lack of patience. When people want to buy a new car, or have a cool new apartment, or be able to tell their friends that they are a millionaire, they do too much borrowing, they do too much stretching themselves thin. They aren’t creating real relationships because they are trying to make a quick buck and all their behavior is predicated on this monetary short term win. If I was about short term thinking, I would really be the polar opposite of who I am.

Diary / Justbobbi / Sep 26, 2022

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