My Meeting with Gary Vaynerchuk: Content vs. Context


Take home message: context is everything.

Last night I spent an hour catching up with Gary Vaynerchuk. As promised, I showed up wearing my Jets winter hat, purchased special for the occasion. Without question, last night’s hour with Gary V. was one of the most thought-provoking and enjoyable conversations I’ve had in a very long time, and from which I’m grateful to have learned a tremendous amount.

By way of background, I asked Gary to meet to discuss our shared trifecta interest: leveraging passion, product, and social media to build and develop businesses. In this respect, Gary is as exceptional as they come. We talked about the shared fire we get from making impact through our writing and engagement with people, and Gary was as candid and thoughtful as anyone I’ve met, and just as exceptional personally as he is professionally.

Gary directed the conversation by asking me if I had 100 points to divvy up, what percentage I would give to creating a legacy and impact and what percentage would I assign to money and fame.

Based on my honest answer of being heavily skewed toward the former, the conversation became one of my most special to date. Gary’s a pay-it-forward guy, and he couldn’t have been more engaged or engaging.

Gary and I share a similar cadence to our manner of conversation: fast-paced and super blunt. As a tennis player, I felt as thought I was smacking the ball around with Nadal, and every so often Gary and I each would pause, look to the other after going miles and minute, and say, “you with me, yes, good.” Gary was giving me tremendous advice on how to turn my passion and skill-set for writing, branding, and speaking into an enterprise. Prior to our conversation I hadn’t used the word “enterprise” when discussing these topics. That’s why I love Gary; because for him, it wasn’t about if, it was about here’s how to do it and here’s why it will work. It’s this type of thinking by Gary that leaves me no doubt that he will own the Jets one day.

The thesis of our conversation revolved around the notion of content vs. context. We discussed my blogging and desire to leave a true legacy through my work and writing, and Gary taught me the following key lesson:

Context is Everything: providing content through a blog isn’t enough. Period. Social media is so diluted with blogs and articles, that simply firing a blog out there (i.e.: content) is the equivalent bringing sand to the beach. I won’t get the necessary traction that way.

Instead, the key is forming connections within social media to people with common interests on a particular blog topic and then engaging with them. Once I post this particular blog about my meeting with Gary, Gary suggested sharing this blog with people who are engaging with him on Twitter. What this does is obvious: it finds a captive audience on the subject matter I’m writing about and shares my own work with them, thereby creating a connection and context. And what does it take? Perseverance, time, and patience. And importantly, for any response to my writing, it’s critical to always engage back with a note of thanks or respond to any and all questions. Engagement creates context.

For those who know Gary, thematic to everything he says involves the hustle. This means no matter how hard one works, it’s time to kick it up times ten. I took significant pride in his commentary that my foundation is strong and that I’m making the right moves, but even more, I appreciated his suggestions of how to scale my model to truly create the legacy and impact that gets my blood flowing. Bust my ass to speak at events, even for free. Blog every day. Guest blog for various publications. And keep on trucking.

I left the meeting having been “Gary V’d” – which is to say, I felt incredibly inspired and capable to take the big swings. And over time, these swings will equate to big hits.

Gary, I’m grateful for the meeting and your excellent advice, but even more, I’m grateful for your friendship.


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