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5 things I learnt from having lunch with #GaryVee

Yes, the headline of this blog is a deliberate attempt to make myself look popular. #SorryNotSorry.

I was, however, lucky enough to be invited to an intimate lunch (intimate as in ‘a small group of people’, not ‘candle lights and truffles’) with Gary Vaynerchuk (AKA Gary Vee) hosted at Facebook’s offices in London.

Gary has become a social media heavyweight in recent years. He is a five-time New York Times bestselling author, CEO of VaynerMedia, a prolific angel investor with early investments in companies such as Facebook, Twitter and Uber and is followed by millions across his social channels.

With the success, however, comes the criticism and Gary has had his fair share of it. I’ve seen many industry blogs that have taken swipes at his content, as well as more educated approaches such as Mark Ritson’s latest Marketing Week column entitled ‘Gary Vaynerchuk is wrong, wrong, wrong, wrong, wrong about media’.

Today, I’d like to focus purely on all the positives to see what we can all learn from the five things I gleaned from meeting the man himself:

  1. The key to an engaging public speech, is finding your comfort zone

Gary spoke over lunch and then I sat and watched his London keynote talk. No notes, no slides, no obvious structure – Gary has developed a conversational style and uses multiple rhetorical questions to make you feel part of a natural dialog.

He has found his comfort zone – informal, conversational, thought-provoking and captivatingly unpredictable.

So often we try and rehearse talks to make us sound like professional speakers. Instead of reading your notes and following your slides, why not take a leaf out of Gary’s book and spend your time trying to find your comfortable conversational zone, and work on bringing the audience into your world of ideas and opinions?

  1. You learn through doing

Through his multi-million pound wine business, Gary made a fortune investing in Google ads before many companies even knew what Google ads were. We had a great conversation around the table about how senior marketers who also run side businesses/hustles tend to learn more about the nuts and bolts of marketing through their side projects than they ever did through their day jobs or in the classroom.

I would wholeheartedly support this view – running my Hack Yourself business has taught me real (and often tough) lessons about pricing, distribution and social media. In particular, when it’s your own money that you are spending on digital adverts, you make damn sure you get the ROI right.

Side businesses could be the very thing that helps upskill and motivate your workforce, so look for ways to embrace your employees’ interests outside of work.

  1. Be valuable first, then sell

Not once did Gary sell his services, even though there were senior client-side brand people in the room.

He focused on being helpful, valuable and insightful.

How many conferences have you been to where the person presenting is just selling and not sharing? Gary focuses on what people need, in order to get their attention. When you get attention, and build a connection, sales will follow.

  1. Capture everything

Gary’s team were recording everything. Multiple photographers and videographers were on hand to capture everything from his talk over lunch, to us chatting, to me scoffing my face with the free smoked salmon. I assume the content will be chopped up, re-purposed and used as engaging pieces later down the line (see Gary’s impressive content strategy here). Let’s hope me and the smoked salmon end up on the cutting room floor.

He sets the standard – whatever you do for your business, whether it’s holding a conference, speaking to clients or out visiting customers, you always have the opportunity to capture something that will be useful for your content strategy.

  1. Have an opinion

Let’s be fair, Gary isn’t short of an opinion or two. He even insulted Facebook briefly, and we were sat in their offices! That’s what makes his content interesting to watch. Although some people may disagree with some of what he says, many others are obsessed with his content because it has a stance, a point of view, and a huge dollop of passion.

I think Ritson’s piece (see link above) is a positive outcome of Gary’s opinionated work. I think it’s healthy that we can read both sides, and help people form new opinions in this ever-changing landscape.

The next time you speak in public, perhaps think about how you can share a strong opinion to challenge people and open up a healthy debate. It might make your talk a little less dull too!

I left the lunch (after slipping Gary a copy of my book, obviously), and watched Gary hold a crowd of around 200 in the palm of his hand. He stood tip toe on the edge of the stage, giving the perception that he would rather be sat with us, debating the topics he is so passionate about.

Finally, meeting and seeing Gary present made me realise this – if you ever speak at an event or a conference, don’t ever, ever go on after Gary Vaynerchuk! Not unless, of course, you are prepared to be just as passionate, interesting and energetic.


Jack is author and founder of Hack Yourself. Read more about it here.

His one-day courses use modern hacking mentality and techniques to enable individuals to become the best leader they can be, no matter what their job title or responsibilities.


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