This isn't a traditional desk job, and we don't care where you went to college—or whether you went at all. I'm looking for an unusually capable, ambitious and resourceful person to become my full-time right hand. You'll work directly alongside an entrepreneur and attorney and help manage a fast-moving mix of business and personal life. On any given day, that could mean coordinating travel, managing appointments and reservations, running errands, handling purchases and returns, researching something I need, solving a last-minute problem, organizing logistics, working on a business project, or traveling with me. You must be extremely comfortable with AI. I use ChatGPT and Claude constantly, and I'm looking for someone who already knows how to use these tools at a high level—not just asking basic questions, but writing strong prompts, researching and synthesizing information, working through complex problems, creating documents and plans, and using AI to accomplish in 30 minutes what might otherwise take several hours. If you're constantly experimenting with AI and finding new ways to use it, you'll fit well here. I'm not looking for someone who needs a detailed set of instructions for every task. I'm looking for someone who hears, "I need this handled," figures out how to make it happen, uses every tool available to them, and comes back with a solution. No college degree is required. Experience as a personal assistant is not required. Intelligence, judgment, hustle, discretion, organization, technological ability and reliability matter much more to me than credentials. This position is in-person and based in the Chicago area , with regular availability to travel. The schedule will not always be 9-5, so flexibility is important. You must have reliable transportation, a valid driver's license, and the ability to travel domestically and internationally. For the right person, this is an opportunity to take on significant responsibility, work closely with me across multiple businesses and investments, travel, learn quickly, and grow into a much larger role over time. If you naturally figure things out, move quickly, take ownership, are unusually good with AI, and hate letting things fall through the cracks, I want to hear from you.

Pay:

$50,000.00 - $65,000.00 per year

Benefits:

Health insurance

Work Location:

In person