Gary Vaynerchuk on entrepreneurship, NFTs, and self-belief at Art Basel Miami

Executive overview

Most people stay stuck because they over-index on other people's opinions — strangers, bosses, family — until it stops them before they start. The antidote is gratitude-fuelled self-reliance and the willingness to lose publicly.

Gary Vaynerchuk spends a packed day at Art Basel Miami across business meetings, a fireside chat with the mayor, a VFriends activation, and fan Q&A sessions. The recurring thread: build from genuine care, not external validation.

Caring deeply about your idea — and ignoring the crowd — is the only sustainable engine.

On entrepreneurship and self-awareness

• Many people who think they want entrepreneurship actually need a job they like more.
• Start with honest self-assessment before quitting anything.
• Posting one piece of content on LinkedIn about your actual expertise can generate inbound job offers within six to twelve months.
• The cheering and the booing should feel the same — fear of public failure is the main blocker.
• Nobody who initially liked the things that worked out for Gary remembered that they didn't.

On gratitude and energy

• Gratitude is described as the most powerful force for sustained energy — but only when it's genuine, not performative.
• Valuing strangers' opinions is the root cause of most stalled ambitions.
• Kindness and competitiveness are not in conflict; there is no scenario where being unkind is the correct move.
• When something goes wrong, the leader's job is to absorb the pressure, not amplify it.

On VFriends, characters, and NFTs

• VFriends characters are each built around a genuine human value Gary cares about — Accountable Ant, the Forthright Flamingo — not clever branding exercises.
• The smart contract's permanent, programmable utility was always the point of NFTs; the 2021 bubble happened when operators stopped building and just flipped assets.
• Physical or experiential utility tied to NFTs brings value back; the best operators know how to use the technology to confirm ownership and trigger benefits.
• The Forthright Flamingo collaboration with Vintage Frames started before Reebok and Starter; nine months of work landed at Basel as an in-store activation.
• Every collaboration is evaluated against a clear "why, what, how" framework tied to a specific character value.

On fashion as a storytelling medium

• Fashion, like music and religion, is one of the most foundational human experiences.
• NFTs made sense long-term to Gary partly because of fashion: people communicate identity through what they buy.
• The goal of character-driven collaborations (sneakers, glasses, children's books, toys with QR codes) is to embed values into culture over the next 47 years.
• Candor — "forthright" — has caused Gary real struggle; the flamingo is his way of story-telling that tension into something useful for others.

On art collecting and learning curves

• Gary is early in his physical art journey, beginning with a Warhol purchase after the VFriends Christie's auction.
• He will not buy art he doesn't yet understand; he expects 2023–24 to be when he goes deep.
• Entrepreneurship is closer to art than to business: drawing outside the lines, seeing needs before they exist.

On content and platform dynamics

• Instagram is in a reset; a post that performed well previously can flop on a near-identical reshare days later.
• Finding a piece of content that does poorly is treated as interesting data, not failure.
• TikTok has become the number one channel for causes like the children's hospital art programme featured at Basel.
• Gary is reconsidering his TikTok positioning — he does not want to be defined as "the garage sale guy" by an entire generation.