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  1. The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
  2. 20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded
20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · Feb 12, 2026

Atlassian's Mike Cannon-Brooks joins 20VC to debate if SaaS is dead, Anthropic's massive projections, Harvey's $11B valuation, and AI's impact.

AI Revenue Is Inflated by "Margin Stacking" Through the Tech Stack

Revenue figures for AI companies can be misleading. The same dollar is often counted multiple times as it moves from the end customer through a SaaS provider and a cloud platform before reaching the model provider, creating a "margin stacking" effect that obscures the true net revenue.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

Engineering & Product Teams Are an "Island of Stability" Amidst AI-Driven Headcount Reduction

While AI threatens to reduce software seats in support and sales, it's having the opposite effect on engineering and product. AI tools are increasing developer output, leading to the creation of more software and stabilizing team sizes, making them a resilient customer segment for SaaS.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

The Public SaaS Growth Average Is Artificially Low Due to a Stalled IPO Market

The perceived slowdown in public SaaS growth is misleading. The metric is skewed because no new, high-growth companies are going public. The current average only reflects the natural deceleration of older companies without the offsetting effect of fast-growing IPOs that historically lifted the median.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

AI Agents Are Shifting Corporate Documentation's Focus from Human Readability to Machine Consumption

The rise of AI support agents is changing the purpose of internal documentation. Knowledge bases are now being written less for human readers and more for AI agents to consume. This leads to more structured, procedural content designed to be parsed by a machine to answer questions accurately.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

AI Giants' Revenue Projections Bet on Eating the $1T Consulting Market, Not Just Software

Anthropic's and OpenAI's massive revenue forecasts ($300B+ combined) aren't about displacing existing software spend. The core bet is that AI will capture a large portion of the trillion-dollar consulting and services budget, dramatically expanding the total addressable market for technology.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

Atlassian's Founder Calls the "Death of Software" Narrative Ludicrous

Atlassian co-founder Mike Cannon-Brookes dismisses the "death of software" narrative. He argues the current AI shift is a typical tech cycle of creative destruction where some companies fail but the overall category thrives. Businesses will always find value in buying efficient, pre-built solutions.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

AI's Impact Depends on Whether a Domain Is Input-Constrained or Creation-Constrained

Atlassian's founder suggests a model for AI's impact. In "input-constrained" fields like legal or support, AI drives efficiency on a finite set of tasks. In "creation-constrained" fields like software development, AI amplifies output on an infinite roadmap, leading to market expansion.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

Public SaaS CEOs Must Balance Investor Demands for Profit with Essential Long-Term AI Investment

Public company CEOs are caught between short-term investor pressure for profitability and the long-term strategic necessity of investing heavily in AI. The challenge is to manage capital allocation to satisfy quarterly expectations while simultaneously funding the fundamental R&D required to compete in the AI era.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

Hyper-Growth in AI Startups Obliterates Traditional TAM Analysis

For AI companies experiencing explosive growth like Harvey (tripling ARR in a year), traditional TAM analysis is an obstacle, not a tool. Such growth signals the company is capturing a new budget pool (e.g., labor costs) that dwarfs the existing software market. In these cases, the revenue trajectory itself becomes the best indicator of the true TAM.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

Anthropic's Super Bowl Ad Was a $5M Signal to Silicon Valley Talent, Not Consumers

The seemingly bizarre Super Bowl ad from Anthropic, which targeted a product it doesn't have, wasn't for the mass market. It was an expensive signal directed at a niche audience: potential engineering hires and enterprise buyers in Silicon Valley, positioning itself as the "good guy" enterprise alternative to OpenAI.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

Customer Support Software Is a "Trojan Horse" to Deploy Horizontal Enterprise AI Agents

The intense investment in customer support AI isn't just about solving support tickets. It's a strategic entry point. A support agent can become the primary AI interface for a company, creating a "Trojan horse" to expand into other functions like sales, marketing, and research, ultimately becoming a horizontal enterprise platform.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago

Venture Capital Abandons Contrarianism for a Consensus-Driven "Winner-Take-All" Strategy

The venture market has shifted from seeking contrarian bets to piling capital into consensus winners, even at extreme valuations. The new logic resembles the old adage "you can't get fired for buying IBM," where investing in a perceived leader with a 1x preference is deemed a safer, more defensible capital allocation decision.

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded thumbnail

20VC: Anthropic's Superbowl Ad: Who Won - Who Lost | Harvey Raises $200M at $11BN Valuation | Sierra Hits $150M in ARR: Is Customer Support Too Crowded

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·7 days ago