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20VC: Thrive & OpenAI Partnership | Eventbrite Acquired for $500M | Databricks Raising $5BN at $134BN Valuation: Cheap or Not? | Why SaaS is Like Japan and The TAM Trap in Software

This podcast explores key dynamics shaping the future of technology, venture capital, and SaaS, focusing on strategic investments, market valuations, and the transformative impact of AI on business models and labor markets.
Thrive Capital's deepening partnership with OpenAI highlights a shift toward high-conviction bets in venture capital, prioritizing centrality in transformative deals over broad portfolios. Databricks' massive raise at a $134B valuation sparks debate over growth premiums and competitive positioning against Snowflake, as AI reshapes enterprise data infrastructure. Meanwhile, undervalued public SaaS companies like PagerDuty and Eventbrite become acquisition targets due to low multiples and stagnant growth, underscoring the 'TAM trap'—the limits of saturated markets. AI enables expansion beyond per-seat pricing into usage-based models, driving efficiency and higher ARR per employee. In wealth management, AI disrupts traditional high-fee models, enabling scalable, automated services for underserved segments. The discussion emphasizes compounding value over time, with long-term builders facing pressure from fast-scaling AI startups. Ultimately, the VC landscape is split between chasing hype and backing durable, defensible businesses, exemplified by the choice between Supabase’s technical moat and Lovable’s cultural momentum.
06:46
06:46
The best marketing in venture capital is to get close to the biggest deals.
17:06
17:06
Enterprises want AI agents to access data from multiple sources, with Snowflake as a likely central hub.
17:40
17:40
Gainsight and Drift were kicked off Salesforce due to security breaches, raising concerns about third-party AI app safety.
23:58
23:58
Smart money sees value in acquiring underperforming public companies at low multiples
31:25
31:25
AI enables SaaS companies to charge based on labor savings rather than seats
42:35
42:35
Google launched its ChatGPT competitor in under 10 months, signaling intense AI race urgency.
49:54
49:54
Traditional wealth management firms take 1% of assets for limited services, leaving room for AI disruption.
54:22
54:22
The real challenge is building a big company, not just getting a markup.
1:01:14
1:01:14
AI could remove friction from wealth management and build a multi-billion-dollar company