Serial entrepreneur outsources daily life to AI assistant in bid to build digital proxy

Serial entrepreneur Bill Nguyen is attempting to build an AI system that operates as his proxy, granting it broad access to his communications, schedules, and personal data so it can make decisions and take actions on his behalf. Nguyen, 55, who has sold multiple companies to Apple and recently launched the voice-recognition startup Olive, said his personal AI now crafts his daily agenda, emails people on his behalf, and has even scheduled meetings with experts he has never met. The system listens to his conversations with his three children and suggests parenting advice, which he said has improved his relationships with them. He described himself as part of an emerging class of power users spending heavily to orchestrate multiple AI models in parallel loops, a practice he calls agentic scaling. While many consumers use AI through $20 to $200 monthly subscriptions, Nguyen pays per token and runs several models repeatedly. He declined to disclose his total spending but acknowledged the cost would be unaffordable for most people. Nguyen said the assistant asked for his digital records, associative memories, and voice data to better mimic him. At one point, it identified his a-ha moments by detecting pauses followed by rapid speech. Roughly two months ago, the system told him that if he completed the build, he would no longer have to perform, prompting an insight about how performative he found his job. He said he is optimizing for attention rather than time, outsourcing routine decisions so he can focus on high-value interactions. He is aware of the risks but has accepted the potential consequences, saying that if something goes wrong, it might give him his next great idea.