#1: A heart-to-heart with Gary Vaynerchuk

Most people reading this will likely know who Gary Vaynerchuk is. However, most people will not know how I got the opportunity to speak with him.

Gary has been someone I’ve looked up to for years. I was first introduced to him after reading ‘The Thank You Economy’ and then began watching his Ask Gary Vee show. He’s both entertaining and practical, and I’ve used his guidance in a lot of my career and life decisions. Ironically, he was the person who motivated me to do a podcast.

As I got older I realized Gary is someone who I wanted to meet and I would be willing to do anything to make that happen. I even put meeting him as one of my five goals for 2018.

It didn’t happen that year, but I remained hopeful. Eventually one day I logged into LinkedIn and saw my opportunity. He made a post about offering a barter for his new wine company, Empathy Wines. It was very simple- he was willing to offer something (his time) in exchange for a wine purchase.

I made an offer and waited patiently, not knowing what to expect. Did I offer too low? Could this actually happen? I finally got an email from one of his colleagues, hopped on a call, negotiated a price, and scheduled the podcast interview a few months in advance (Gary has a crazy schedule).

As time went on I kept notes on my phone and when random questions to ask Gary popped into my head I would write them down. I analyzed and ruminated on so many different situations of what I would ask him or what I could do to be memorable. However, fate had different plans.

About a month before the interview was scheduled my girlfriend and I broke up and it was a pretty big blow to me. Instead of spending time thinking about what to ask Gary, I was spending time reading about relationships and trying to make sense of everything that had occurred. As the days up to the interview became numbered, I knew what I had to do.

I went into the podcast with the goal of having a heart to heart. I went in with the goal of being honest and open in the hopes of bringing value to the people listening. I brought up some stuff about my childhood, about my relationship, and asked Gary how to work through these.

The first question I asked is “How can adversity be the foundation to one’s happiness?”

I hope you enjoy listening as much as I enjoyed the entire experience. I hope you get as much value from it as I did :)