#AskGaryVee in Person: What's Your 1 Question?


I’m more and more intrigued by a man who doesn’t believe in motivation or luck, only action. And if you’re a fan of the #AskGaryVee or #DailyVee YouTube shows, you won’t see a busier man run through meetings, conferences and airports like Gary Vaynerchuk.  

I spent the last of my grocery money to buy a pair of K-Swiss shoes for my son, when my son normally wears Vans. And I drove 45 minutes to Hollywood to go buy them so I could get a paper wristband to go see Gary Vaynerchuk.

Last year in Nashville, he was the keynote speaker for an event run by the company I work for. As a low ranking Production Assistant, I didn’t have the chance to ask him any questions or get a selfie.

But this past year I became a different person because I combined writing and my business into a side hustle. Soon, each vacation day that I took from work was spent on my business, and I began to take crazy risks to make it flourish. I didn’t feel like I missed out on anything. Instead, I felt more fulfillment through the daily process of putting in the work; it was like writing, or dancing, my 2 favorite passions, the daily practice is so difficult but once you’re done you can’t imagine spending time any other way. I was smelling the roses, or the process, while many people were burning out and giving up.

Gary wins at the game, hands down. And he wins through a few fundamental truths. So during the 30 seconds with Gary, in between taking a photo and getting his autograph, each person there had a chance to sneak in a question:


While waiting, I asked people what their one question for Gary would be (this is the compulsive journalist in me, always searching for the story). I was amazed at the number of people who didn’t have a question ready.

But this culture Gary Vee built had people driving for hours in Los Angeles traffic to come and say thank you. Look back on some episodes of #DailyVee, you’ll hear Gary talk about gratitude and start thinking about running the business as a golden opportunity by saying to yourself, “You GET to” run your business instead of “you HAVE to.”  

The Millennials

Gary is a champion for Millennials because at his core, Gary understands that people come first.

Q: How do you appeal to millennials?

A: Millennials want purpose, to feel like they can contribute to a greater purpose, or they want money. Find out what they want, and appeal to one or the other.

Now, anyone out there who tells millennials that they are selfish and entitled to want purpose or money in their careers, take a look back first. In my parents’ generation there were either hippies, (in my parents case, they were activists in the movement led by Cesar Chavez) and those who became the iconic mad men. In my generation, there were the social justice activists like me—in my ‘20s, speaking out against inequality, and the dotcommers. Has much changed and do the Millennials deserve these labels? Because Gary Vee didn’t label them this way.   

Self-Awareness Wins

Once I started to own my self-awareness, I doubled down on my strengths and accepted my weaknesses, and Gary was exactly right, I saw more potential in myself and my business.

I knew my strength and my true love was writing. It always will be, so I doubled down on getting better at my craft and wrote more than the average 500 words I disciplined myself to do every day. I knew my weakness was design. I’m horrible at it and I hate it, always will, so I asked for help and critique.

Once I increased my strengths in writing, I realized that I knew the craft of storytelling and I wasn’t limited to books and blogs, but I could use different platforms. So my one question for Gary:

Q: What’s the Future of storytelling?

His answer? Well, it’s my next big project set to launch next month.  

What’s your 1 question?

If you had the 30 second chance to ask Gary that one question, what would it be? Are you asking because you need to start? Or because you want to build bigger? Would it be for you, your team, or would you just say thank you because you became a different person?

Once you meet Gary, you start to realize that you could win. So follow Gary Vee’s best advice—go out and execute. THEN you’ll win.


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