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The Monthly Interview: Gary Vaynerchuk

We speak to the founder, investor, author, speaker and internet personality about creative entrepreneurship, the underrated power of optimism, and why his agency will never – ever – go public

Gary Vaynerchuk isn’t one for small talk. Seconds into our meeting the conversation has vaulted from ‘how do you do?’ to a philosophical point about the importance of optimism. Pessimism is easy, he muses. Cynics can be explicit about their doubts, while hopeful people are prone to keeping their cheer under wraps for fear of being torn into.

Not him though – with so much negativity around, he feels a responsibility to use his voice to pump people up. I’m to learn that Vaynerchuk’s observations are panoramic. Our chat will cover off issues ranging from the troubled state of advertising, to whether companies might be better if they resembled monarchies. It’s big talk only.

Speaking of negativity, a quick glance at our surroundings doesn’t give much cause for it. The get-together is happening on a sun-blanched deck aboard the VaynerX yacht, which is moored in the French Riviera for the Cannes Lions Festival of Creativity. There is a bounteous spread of continental breakfast fare, and an implausibly tall bar offers a steady supply of coffee during the day, and cocktails at night. Team members float around clad in linen (of the quiet luxury variety).