In this Business Brain episode, Dave Hamilton celebrates the 20th anniversary of his first podcast, Mac Geek Gab, reflecting on how a direct email to Steve Jobs led to Apple featuring his show on the launch day of their iTunes podcast directory. This moment serves as a springboard for a broader discussion with Shannon Jean about the importance of building relationships with decision-makers early—before you need them. Shannon shares a similar story from his time selling on Poshmark, where connecting with the company’s executives via LinkedIn eventually led to major promotional support. The takeaway: establish valuable connections in advance, and don’t hesitate to reach out directly—it’s often the “third door” to opportunity.

The second half dives into emerging uses of AI as personal assistants. Shannon shares a powerful case study from Nick Hulinski, who uses Claude (an AI model) to streamline his calendar, email, and weekly planning—essentially replacing the need for a human assistant. Dave and Shannon express interest in building a similar setup and lament Apple’s slower pace of integrating these AI tools in a privacy-conscious way. They also touch on how tools like Claude and ChatGPT are helping users build personal operating systems and frameworks for decision-making. The episode wraps with an invitation to connect, watch the live stream, and engage with the hosts directly through LinkedIn or email.

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