Grammarly’s $1B Round, Brain Computers, and NYT Licenses To Amazon | E2133

This Week in StartupsAbout 7 min readJun 3, 2025Watch original
THE SUMMARYAI-generated

Key Concepts

AI, Brain-Computer Interfaces (BCI), Copyright Infringement, Image Rights, Music Licensing, Name Image and Likeness (NIL), Venture Capital, Software as a Service (SaaS), Initial Public Offering (IPO), Liquidity, Social Media Addiction, Ethical Technology Design.

AI and Intellectual Property

Voice Cloning and Image Rights

  • Main Point: The increasing sophistication of AI voice cloning technology raises concerns about the unauthorized use of celebrity voices and likenesses in advertising and other commercial contexts.
  • Example: A Google video featured an AI avatar using Jason Calacanis's voice, prompting a discussion about the legal and ethical implications of such technology.
  • Legal Framework: The "right of publicity" is a state-level legal right that allows individuals to control the commercial use of their likeness, name, and other identifying characteristics.
  • Notable Quote: "If this was a real thing...and somebody actually used this in an ad like it would be quite actionable." - Jason Calacanis
  • Real-World Applications: Instances of celebrities like Joe Rogan and Elon Musk being used in cryptocurrency scams highlight the potential for misuse.

AI Music Generation and Copyright

  • Main Point: AI music generation companies like Udio and Suno are facing copyright challenges from the music industry due to the potential infringement of existing artists' rights.
  • Industry Dynamics: The music industry is highly coordinated, with various groups owning mechanical rights, lyrics, songwriting, and performance rights.
  • Settlement Terms: Settlements often involve significant payments and equity stakes for the music labels.
  • Example: Peloton faced a painful settlement for using unlicensed music in the background of its classes.
  • Workarounds: Using royalty-free stock music or prompting AI with generic descriptions (e.g., "blues" or "fingerpicking guitars") can help avoid copyright issues.
  • Equity Stakes: Music labels may demand equity in AI music generation companies as part of licensing agreements, similar to Spotify's early deals.
  • Google Trends Data: Interest in Udio and Suno has remained relatively stable in 2024, suggesting sustained interest despite licensing challenges.
  • Future Implications: The discussion raises questions about whether AI-generated music inspired by specific artists should result in royalties for those artists or their labels.

New York Times and Amazon AI Deal

  • Main Point: The New York Times has entered into a licensing agreement with Amazon to provide summaries of its content for Amazon products and to train Amazon's proprietary foundation models.
  • Strategic Rationale: The deal allows the NYT to demonstrate the value of its content to language models and potentially negotiate better terms with other AI companies like OpenAI.
  • Financial Impact: The deal could significantly increase the NYT's revenue from affiliate licensing, potentially reaching a double-digit percentage of their total revenue.
  • Amazon's AI Models: Amazon has a range of in-house AI models under the "Nova" name, including Nova Micro, Nova Light, Nova Pro, Nova Premiere, Nova Canvas, and Nova Real.
  • Subscriber Base: The NYT has 11.66 million subscribers across all platforms as of Q1 2024.
  • Notable Quote: "This is a way for them to say to Open AI look this is the value that you stole from us amazon is willing to give us this level of deal and you just took it." - Jason Calacanis

Venture Capital and SaaS

Grammarly and General Catalyst

  • Main Point: Grammarly received a $1 billion investment from General Catalyst's "customer value fund," a revenue-based financing model that provides capital without taking an equity stake.
  • Strategic Rationale: The investment aims to fuel Grammarly's growth and product development, particularly in building an AI-powered writing platform.
  • Financial Performance: Grammarly has annualized revenue of over $700 million and is profitable.
  • GC's Perspective: GC benefits by increasing the value of its existing equity stake in Grammarly without diluting its ownership.
  • SaaS Market Dynamics: The discussion touches on the challenges faced by SaaS companies due to layoffs and static team sizes, which can impact per-seat revenue.
  • Alternative Pricing Models: SaaS companies may need to move away from per-seat pricing and adopt consumption-based models.
  • Liquidity and Returns: The revenue-based financing model could provide faster returns to GC's limited partners (LPs).

SaaS Rollups and Vertical Integration

  • Main Point: There is growing interest in SaaS rollups, where multiple software companies are combined to share resources and increase efficiency.
  • Private Equity Style Takeovers: Venture capitalists with large funds are increasingly considering private equity-style takeovers of mature SaaS companies.
  • Vertical Integration: Some companies are pursuing vertical integration by acquiring both the software and the end-user businesses, applying AI and SaaS technologies to improve efficiency.
  • Example: A company making software for barber shops could buy barber shops and use its technology to improve their operations.
  • Challenges: Venture capital firms may lack the operational expertise to manage real-world businesses.
  • Historical Precedents: Barry Diller's rollups of travel companies (Expedia, etc.) and dating sites (Match.com) serve as examples of successful consolidation strategies.

Autopilot and Portfolio Tracking

  • Main Point: Autopilot, a company that allows users to mimic the portfolios of successful investors, has reached $750 million in assets under management (AUM).
  • Business Model: Autopilot charges quarterly or annual fees to track portfolios, with users' money remaining in their own brokerage accounts.
  • Market Share: Reaching $1 billion in AUM would be a significant milestone, indicating proven market demand.
  • Nancy Pelosi Tracker: Autopilot's tracking of Nancy Pelosi's trades has generated significant attention and customer acquisition.
  • Venture Backing: Autopilot is backed by firms like Incline Ventures, Group Nomad Ventures, and Craft.

Brain-Computer Interfaces (BCI)

BCI Advancements

  • Main Point: Several companies, including Neuralink, Precision Neuroscience, Synchron, and Paradomics, are making progress in the development of brain-computer interfaces.
  • Paradomics: Paradomics recently conducted its first insertion and removal of a brain computer implant in a patient undergoing brain surgery.
  • Neuralink Funding: Neuralink has raised $600 million at a $9 billion valuation.
  • Independent Usage: Data from Neuralink shows that users are independently using their brain implants for increasing hours per month.
  • Potential Applications: BCIs have the potential to help paralyzed individuals walk, restore sight to the blind, and treat neurological diseases.
  • Ethical Considerations: The discussion touches on the potential for BCIs to be used for purposes such as dream manipulation and experiencing virtual realities.
  • Strange Days: The movie "Strange Days" is referenced as an example of a fictional BCI technology that allows users to record and replay experiences.

IPO Market

Upcoming IPOs

  • Main Point: Chime, Circle, and Voyager Technologies are all expected to go public in the near future, potentially providing much-needed liquidity to the venture capital market.
  • Chime: Chime is targeting a $24-$26 per share price, valuing the company at $10.3-$11.1 billion.
  • Circle: Circle increased the size of its IPO and raised its price range to $27-$28 per share, valuing the company at $6.8-$6.9 billion.
  • Voyager Technologies: Voyager Technologies is expected to list at a $1.6 billion valuation.
  • Market Sentiment: The success of these IPOs could boost confidence in the market and encourage other companies to go public.

Ethical Technology Design

Lauren Powell Jobs and Jony Ive

  • Main Point: Lauren Powell Jobs and Jony Ive are discussing the ethical implications of technology and the need for devices that promote well-being and human connection.
  • Criticism of Social Media: They are critical of social media's addictive nature and its negative impact on mental health, particularly among young people.
  • Potential Device: They may be working on a device that uses AI to encourage users to make better use of their time and prioritize activities that promote well-being.
  • Apple's Approach: Apple's focus on health, creativity, and human connection is contrasted with the more addictive and data-driven approach of social media companies.
  • Puck Concerns: Jason expresses concerns about the privacy implications of devices that record people's daily lives.

Conclusion

The discussion covers a wide range of topics, from the legal and ethical challenges posed by AI to the dynamics of the venture capital market and the potential of brain-computer interfaces. Key takeaways include the need for responsible AI development, the importance of protecting intellectual property rights, and the potential for technology to both harm and improve human well-being. The upcoming IPOs of Chime, Circle, and Voyager Technologies could provide a much-needed boost to the venture capital market, while the ethical considerations raised by Lauren Powell Jobs and Jony Ive highlight the importance of designing technology that promotes human flourishing.

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