Navigating Venture Capital: Strategic Considerations for Entrepreneurs

Today, Eric is joined by Contrary general partner Kyle Harrison for a candid conversation on how the venture landscape looks from the founder’s perspective in 2025. Kyle breaks down the structural shifts reshaping the VC ecosystem — from the hollowing out of mid-sized firms to the growing divide between capital agglomerators and specialist funds — and what it all means for entrepreneurs raising today.

They discuss how larger venture firms’ need for outsized returns shapes their approach to competition, ownership, and ambition, and why smaller funds are often better aligned with founders looking to build more deliberate, less capital-intensive businesses. Kyle also shares advice on how founders should evaluate prospective investors — not just on marketing or personality, but on fund dynamics and long-term incentives.

We also covered Airbnb’s new services and app redesign, Anthropic’s upcoming Claude models, Perplexity’s move into agentic commerce with PayPal, and Zepto’s launch of a real-time insights platform for consumer brands in India.