For my entire career in tech and startups, Fred Wilson has been like the god-level VC in the New York City ecosystem. Fred got his start investing before the dotcom bubble, rode the bubble investing in the earliest internet companies to great success, and then turned Union Square Ventures into the premier venture capital firm on the east coast. Hear the story of Fred’s investments in Geocities, Etsy, Coinbase, MongoDB among others. When I first started this podcast almost 12 years ago, Fred was one of the top 5 people I wanted to talk to.

11:08 Fred Wilson's Journey into Venture Capital

21:34 The Rise of New York's Tech Scene

34:53 Founding Union Square Ventures

48:00 The Evolution of Web 2.0

57:16 Current Technological Intersections and Future Outlook

Fred Wilson transitioned from naval engineering to venture capital due to a passion for technology and finance.

The New York tech scene began to emerge in the early 90s with digital media and online services.

Flatiron Partners was founded to focus on internet investments during the dot-com boom.

Investing in companies like GeoCities and Etsy showcased the potential of the internet.

The dot-com crash taught valuable lessons about sustainable business models.

Union Square Ventures was founded during a challenging economic period, emphasizing the importance of the application layer of the internet.

The rise of social media and user engagement became central to investment strategies in the 2000s.

Fred's blog became a platform for sharing ideas and attracting founders to his firm.

Current technological advancements are driven by the convergence of AI, biology, energy, and crypto.

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