Brands, Discovery and the New Toll Booths

Gary Vaynerchuk is an entrepreneur, investor, and one of the earliest pioneers of the social media economy. His career has been defined by his ability to spot major shifts in technology and culture long before they become obvious. In this conversation, Gary and I debate whether we may be at the beginning of the end of the social media era as we know it, and how artificial intelligence is already cracking the current value proposition of today’s platforms. We explore the contrast between the emerging data showing that specifically Gen Alpha are spending more time offline and then what the future looks like with AI-generated content, voice-first technology, and the rise of augmented reality. We also dive into what this means for creators and brands and how people can start positioning themselves now for the massive shifts ahead. Follow Gary: https://www.instagram.com/garyvee/?hl=en Get his latest book: https://www.amazon.com/Day-Trading-Attention-Actually-Social/dp/0063317591 Timestamps: 00:00 – Are We at the Beginning of the End of Social Media? 02:40 – How AI Changes the Psychology of Posting and Attention 07:30 – Voice Technology, Smart Glasses, and the Next Distribution Shift 11:50 – Why New Technologies Always Start Clumsy Before Transforming Everything 14:40 – Data on People Spending Less Time Online and Gen Alpha’s Changing Habits 18:30 – Authenticity in the Age of AI and Technology 26:00 – A Future Where AI Agents Handle Everyday Decisions 30:40 – How Brands and Creators Break Through in an AI-Driven Economy 38:30 – Tech Incumbents, Consolidation, and Signals of Change 41:30 – The Future of Entertainment and Immersive Experiences 42:10 – What Creators Should Be Doing Right Now to Prepare

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