Here’s What the Next 5 Years Will Actually Look Like

Gstaad Guy opens by describing Gary Vee as someone who sees trends early and places bets before they become obvious, citing Gary’s early investment in his office and podcasts. Gary says this is deliberate: he studies consumer behavior, human psychology, and emotional intelligence, then uses intuition and pattern recognition to distinguish a one-day fad from an emerging norm. He describes himself as a cultural anthropologist, human strategist, and consumer scientist who applies those observations to investments, personal branding, and companies. He says his favorite puzzle is identifying what is happening before the rest of the world recognizes it.

Gary recalls being called a “whiz kid” during his twenties, when newspapers covered his family’s internet wine business, and says he now enjoys becoming “unk” and eventually “grandpa to the universe.” He explains that a meaningful part of aging is gaining the ability to encourage younger people. Gstaad Guy recalls having fewer than 100,000 followers when Gary messaged him encouragement; he immediately called his friend Logan, who said Gary did not do that for many people and must believe he was onto something. Gary is visibly moved that a brief message from him had supplied someone else with fuel.

Gstaad Guy says getting over the fear of being cringe was one of his most consequential decisions. Gary responds with his phrase “judge the judger,” describing a business interaction in which someone cited several critics’ opinions; Gary asked what those people had actually accomplished professionally. He argues that people should be thoughtful about whose judgment they accept and should examine the motives behind it. Much criticism, he says, is insecurity being imposed on someone else—for example, people who fear being mocked for making videos may discourage others from posting. A few words from the right person can outweigh a much louder stream of discouragement.

Gstaad Guy recounts a former boss noticing that he had asked his family, two friends, and then her for advice about a woman he liked. She told him he was not seeking truth but confirmation, or “enablement.” Gary agrees that people often use newer terms such as toxic positivity or imposter syndrome for this behavior, and admits that his own optimism made him enable loved ones’ bad conduct. He says that over the last five to seven years he has become more candid, telling insecure people when their behavior hurts others or could get them fired. Love and positive reinforcement help, but they must be paired with direct accountability.

Gary says his willingness to bet on people is intuitive and comes partly from not fearing that they will let him down. He is drawn both to pure self-confidence and to insecurity, which he now sees as opposite sides of the same issue; earlier in his career he tried to compensate for insecure people’s lack of love, but sometimes enabled them. He also looks for curiosity, optimism, and an expansive sense of “maybe” rather than cynicism. Optimism must include practicality: Lady Gaga combined belief with work, whereas people who merely predict fame without doing the work are delusional.

Gstaad Guy distinguishes genuine nostalgia from romanticizing the past to demonize the present, observing that some people reflexively say every new restaurant, trend, or era was better before. Gary agrees and says this posture is often a way to feel superior, though it makes people less impressive. He is not enthusiastic about every aspect of AI, but refuses to become delusional about technological change: humans previously feared electricity, automobiles, airplanes, and medicine. He argues that complaining about AI will not stop it, especially when jobs are threatened, and that time spent learning to use it is more productive than repeatedly criticizing it.

Gary calls AI as significant as the internet and says the next five years may feel more like 2050 than 2031 because change will accelerate. At the same time, he expects a countertrend toward “1950 behavior”: suburban neighborhoods may organize communal barbecues, and people may spend more time at sporting events, festivals, conventions, food gatherings, meditation retreats, and wellness events. He predicts that AI-driven efficiency could eventually support a four-day workweek, leaving three-day weekends for real-world activities. He describes the present as the pre-dawn of actual unplugging, not merely posting about taking a hike while remaining digitally engaged.

Gstaad Guy worries that tools such as Shopify may free entrepreneurs’ time only for some to spend it doom-scrolling, while attention spans shrink and digital temptations intensify. Gary compares this with alcohol: society had to learn how to manage and educate around it rather than simply ban it. He says his own major vulnerability is processed sugar, and argues that parents must actively set rules for children’s phone use. Adults must also stop blaming platforms for every lapse—his missed workout was not caused by the weather, his phone, or Instagram. He says society has become better at pointing fingers than “pointing thumbs” and needs more personal accountability.

Asked what he wants in teams as specialization becomes less necessary, Gary says the near-term threat is not AI taking jobs but people who use AI taking jobs, which he already sees happening. He wants optimism, curiosity, adaptability, creativity, and practical skill. He describes how he asked ChatGPT to analyze the rise of men wearing charm bracelets, including its historical references, brands, and likely durability, using AI as a thinking partner rather than a search engine. He predicts agents may buy routine items such as deodorant, carrots, and shoes within 24–36 months. He coins “COP”: a curious, optimistic, practical person willing to practice.

In the closing game, Gary puts fear-based personal brands and people who tear down others to make their own “building” look taller “in the trash.” He wants to celebrate people who build businesses without needing to diminish competitors, and group dinners of seven to ten people conducted as one conversation rather than scattered side chats. His final advice is aimed at wealthy, well-connected listeners: do not fear losing friends you once dreamed of having if they no longer bring emotional value. Keep some superficial “dessert,” but spend most time with people who genuinely care, including kind people within elite circles rather than merely those who provide access.