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20VC: Why VC Today is Worse Than 2021 | Why Vertical SaaS is a Bad Investment Today | Why We Are Deluding Ourselves on Growth Expectations | Revolut Raises $3BN at a $75BN Valuation | Benchmark Adds Their Newest General Partner

The podcast delves into the evolving landscape of venture capital, spotlighting strategic shifts driven by AI, ballooning valuations, and changing investment dynamics. With Benchmark adding a new general partner, the conversation sets the stage for a deeper exploration of how VC firms are adapting to an increasingly complex and capital-intensive environment.
The discussion examines how rising AI infrastructure demands and inflated private market valuations—exemplified by Revolut’s $75B valuation—are reshaping venture capital. Over-optimism in narrow markets like legal SaaS risks massive write-downs, as total addressable markets fail to support sky-high growth assumptions. Vertical SaaS faces headwinds due to limited scalability and high customer acquisition costs, while the era of small contracts no longer suffices; companies must push for $10K+ minimums to achieve meaningful revenue. The concentration of compute power among giants like OpenAI and Anthropic is forcing startups to build proprietary models and infrastructure, increasing capital intensity. Despite strong paper returns, VC has underperformed public markets, with long fund cycles and distribution delays undermining investor confidence. The current environment, marked by aggressive funding and speculative enthusiasm, mirrors past hype cycles, suggesting a future correction. Sustainable success will favor disciplined, focused strategies over blind bets on AI-driven growth.
07:15
07:15
One speaker's 2017 fund is expected to hit five X on paper by year-end after many years of no returns.
10:19
10:19
The best wins start with a small niche market and expand addressable market later.
31:01
31:01
VCs may lose 80% of AI B2B investments due to ignored TAM limits
34:32
34:32
The legal sector is attractive for vertical SaaS due to high-value contracts with IP law firms.
41:07
41:07
OpenAI offloads balance-sheet risk to investors while keeping upside rewards
53:16
53:16
Over-investment in AI capacity, not tech failure, risks a future bust
1:00:03
1:00:03
Venture returns in the last five years have been much lower than public market returns
1:09:29
1:09:29
Content moderation at ChatGPT will be one of the hardest jobs in tech over the next five years.