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Positivity and optimism have always been two of the big pillars of what Gary preaches in his content. You can see his passion for this conversation through his video “No one knew me 10 years ago.

Gary shows a side that most haven’t seen — a more vulnerable and sensitive side. He shows how everyone, including him, have had to make difficult decisions in life in order to achieve success and happiness.

Gary felt a lot of pressure to set a good example from his parents and younger siblings. This pressure built up a lot, since he wasn’t a good “role model” from an academic standpoint. But he was able to set an example by being a good, hardworking human being.

Even with high stakes (i.e. the outcome of his family’s business and being used as a “north star” for his siblings) he was comfortable in that adversity and even subconsciously created those situations for himself.

Listen to him talk about it in detail and with vulnerability at 7:51.

The kid who hated losing

16:03 Growing up, Gary was always the type of kid who was extremely competitive and hated losing. He was viewed as a “loser” because getting D’s and F’s in school were indicators of a complete failure to the people around him – but over time as entrepreneurial success became more accepted as a measurement of success in society, things changed.


At 9:58, he talked about crying as a kid when he lost in anything because he hated it so much .

But he didn’t let those outside voices get to him, and the word he uses to describe this feeling is discussed here at 16:50.

Starting over

28:36 When Gary started growing Wine Library rapidly, he started getting credit for a lot of the success behind the business. This created a pretty big point of contention between him and his dad, who owned the business.

He felt that he needed to take a leap and start over – one of the toughest decisions he had to make.

Listen to the podcast:

Watch the full interview: