Hustler Words – Veteran investor Kevin Rose, known for his early bets on Peloton, Ring, and Fitbit, employs a rather direct method for evaluating AI hardware: would you instinctively want to punch someone wearing it? This blunt assessment highlights a growing concern about the social acceptability and potential privacy violations of the latest wave of AI wearables.
Rose, a general partner at True Ventures, has largely avoided the rush to invest in AI hardware, observing that many startups are repeating past mistakes. He believes that the "always-on, always-listening" nature of many AI devices infringes upon fundamental social constructs surrounding privacy.
Speaking at Hustler Words Disrupt, Rose emphasized the importance of emotional resonance and social acceptance, alongside technical capability. He questions the healthiness of devices constantly striving to be the smartest in the room, noting that the emotional impact on both the user and those around them is often overlooked.

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Rose’s skepticism stems from personal experience. He recounted an incident involving a failed AI pendant where he attempted to use its logs to win an argument with his wife. This experience solidified his belief that such devices can be detrimental to healthy relationships and social interactions.
He also criticized the tendency to "bolt AI onto everything," citing examples like photo apps that allow users to erase elements from the background, potentially altering memories and creating a false sense of reality.
Rose worries that we are in a similar phase with AI as we were in the early days of social media, making decisions that may seem harmless now but could have negative consequences in the future. He uses the example of his children asking about puppies they saw in a video generated by OpenAI’s Sora, forcing him to explain the concept of AI-generated realities.
Despite his reservations about certain applications of AI, Rose remains optimistic about its potential to transform entrepreneurship. He notes that the barriers to entry for entrepreneurs are shrinking rapidly, citing an example of a colleague who built and deployed an entire app using AI coding tools during a single car ride.
Rose predicts that AI will continue to democratize entrepreneurship, enabling high school students to build billion-dollar businesses. This shift will also impact the venture capital industry, as entrepreneurs can delay or even forgo fundraising.
He believes that the value proposition for VCs will shift towards providing emotional support and long-term partnership to founders, rather than simply offering technical expertise.
Rose seeks founders with a "healthy disregard for the impossible," those who are pursuing bold ideas that others dismiss as crazy. He values the minds of these innovators and is willing to back them even if their initial ventures fail.








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