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May 28, 2025 32 mins

What happens when a billion-dollar company can be built by a team of one, or just a few, thanks to AI? In this episode, we explore how artificial intelligence is revolutionizing work, mentorship, entrepreneurship, and organizational structure.

Our guest, a veteran tech entrepreneur Dave Sifry, shares hard-won lessons from scaling startups like Technorati, insights on company growth breakpoints, and candid reflections on how Gen Z and Gen X are navigating this new world. We unpack the socio-economic implications of AI, the dangers of centralized power, and the once-in-a-generation opportunity to build lean, impact-driven companies.

Whether you're starting out or reinventing yourself mid-career, this conversation is for anyone curious about the real future of work.

 

00:00 Introduction and Setting the Stage

02:03 Adapting to Technological Changes

02:15 The Role of AI in Mentorship and Learning

02:39 Human Connection and Societal Impacts of AI

03:34 Generational Differences and Career Reinvention

04:37 Sociological Implications of AI

06:17 Practical AI Applications in Career Growth

09:55 The Journey into Entrepreneurship

14:36 Building and Scaling Technorati

17:24 Leadership Challenges in Growing Companies

26:55 AI's Impact on Organizational Structure

30:43 Concluding Thoughts on AI and Business

Mark as Played

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