The recent lawsuit filed by the Chicago Tribune against Perplexity AI has ignited debates across the startup and tech worlds, touching on copyright law, AI practices, and the responsibilities of digital platforms. As a female founder and seasoned entrepreneur who actively bridges the educational and tech sectors, I find this case particularly striking. It isn’t just about legal dynamics; the lawsuit reflects wider implications for startups, especially those leveraging advanced technologies like AI.
Let’s unpack the matter and examine what it teaches entrepreneurs, particularly us bootstrapped founders, in navigating innovation ethically and sustainably.
The Basics of This Legal Clash
On December 4, 2025, the Chicago Tribune initiated legal action against Perplexity AI in a New York federal court. The main accusation? Perplexity AI allegedly infringed on copyright by reproducing Tribune content through its products, including its AI-enabled Comet browser. The claims go beyond simply pulling public data; they accuse Perplexity of bypassing the Tribune’s paywall and offering detailed content summaries without user visits to the site.
This isn’t just noise targeting one company. It’s part of a larger wave: Tribune and its parent company, MediaNews Group, aren’t strangers to lawsuits in the AI space. Previously, they also targeted OpenAI and Microsoft for training their models on proprietary media content.
Yet, this case with Perplexity touches on a relatively unexplored area. It questions not only how AI models are trained but also how they use and present real-time data. This shifts the focus from historical data usage to everyday functionality.
Lessons for Female Entrepreneurs Competing in Advanced Tech
As someone who has worked extensively to advance women in STEM through initiatives like the Fe/male Switch startup game, I believe litigation trends like this should ring alarm bells for all founders in AI or digital media. Here’s what we can gather from the ongoing case:
1. Understand Intellectual Property Limits
Startups often cite “fair use” as a magical buffer for their product development. But as this lawsuit shows, scraping, reproducing, or imitating content, even with minor tweaks, can be legally precarious. Tech like Retrieval Augmented Generation (RAG), while useful for ensuring factual outputs, also poses new copyright complications, especially if it bypasses pay models.
Practical tip: Educate yourself and your team about copyright laws and their complexities. For example, read the official explanation from WIPO on fair use vs. infringement in AI models. Engaging with experts familiar with both technology and intellectual property can save costly legal disputes later.
2. Transparency is No Longer Optional
Perplexity claimed their AI models were not trained on the Tribune’s content. That sounds like compliance on the surface, but the lawsuit suggests otherwise, bringing up RAG-powered summaries. This hints at the importance of being fully transparent about both training and how your algorithms currently operate.
Practical tip: Show your users and clients the pipeline of your model's input. Tools like documentation, transparency notes, or even audits (voluntary or required) deliver trust. More founders should integrate ethics early into product development, not as an afterthought.
3. Don’t Alienate Important Ecosystem Players
One of the startups I co-founded, CADChain, deeply emphasized cooperation with industry partners, including legacy players wary of new tech. Perplexity’s approach, as described by the Tribune, feels adversarial: bypassing paywalls and using phrases like “skip the links” as part of a product marketing tactic seems more combative than collaborative.
Practical tip: If your tech impacts another business sector directly (like media, finance, or healthcare), build dialogue early. Reach partnerships where possible. For instance, look into agreements similar to publisher licensing partnerships, already embraced by companies like Google.
The Broader Trends: Female Entrepreneurs Take Note
The Tribune lawsuit reminds us that the tech shakeups of the modern world don't exist in a vacuum. AI developers and legacy industries like print media are more likely to collide in courts as new business models disrupt traditional ones. How do we, as female leaders, start learning from these tensions rather than blindly chasing innovation?
Common Mistakes to Avoid When Scaling Tech Startups:
- Failing to diversify your funding sources: Don’t let eventual legal scares (or any risks) paralyze cash flow. Bootstrapped founders must work extra hard at reliable revenue models not built on precarious growth.
- Ignoring “soft trust” work until too late: If media companies feel exploited by your platform, even without direct infringement, this creates public perception risks as much as legal ones.
- Under-prioritizing ethical design: Show users and clients you care about navigating complicated boundaries responsibly. Document early decision points, this doubles as proof if anyone questions your methods later.
Useful Tools and Resources for Navigating Legal Risks in AI as a Startup Founder:
- Use open-access legal libraries like Harvard’s CopyrightX and guides shared by Creative Commons.
- Build your compliance knowledge via AI-focused online courses. For instance, futurelearn.com offers free and moderately priced legal literacy courses for creators.
What Can Entrepreneurs Actually Do with Lessons Like These?
When I reflect on my experiences designing AI-focused startup methodologies, including the initiatives at Fe/male Switch, a recurring insight emerges: being strategically cautious doesn’t mean avoiding risk completely. It means knowing where both opportunity and limits lie. Entrepreneurs, especially women entering experimental areas without vast legal budgets, should be proactive in staying informed (not defensive), especially when regulation follows innovation.
Litigation frightens startups because it stretches already-tight resources. But if more founders build safeguards like transparency, ethical decision points, and adaptable business models, disputes may become manageable, even avoidable.
The lawsuit between the Chicago Tribune and Perplexity AI is one of many cases shaping the interaction between media and AI development. Whether you are building an AI-based product or bootstrapping a tech niche, understanding such conflicts equips you to move strategically. Don’t wait for these battles to escalate; proactively align your methods with your market before disputes arise.
For more updates on legal and ethical lessons for tech startups from an entrepreneurial perspective, stick around or explore Fe/male Switch, where we empower women founders to succeed confidently, ethically, and smartly.
FAQ
1. What prompted the Chicago Tribune's lawsuit against Perplexity AI?
The Chicago Tribune alleges that Perplexity AI infringed on its copyright by bypassing paywalls and using its content in AI-enabled tools like the Comet browser without authorization. Read the original TechCrunch report
2. What legal claims does the lawsuit include?
The lawsuit accuses Perplexity AI of three counts of copyright infringement, trademark dilution, false designation, and unauthorized use of content. Learn more about the case
3. Why does Retrieval Augmented Generation (RAG) play a key role in the lawsuit?
RAG technologies, used by Perplexity AI, are capable of retrieving and presenting paywalled or protected content, which the lawsuit challenges as an unauthorized practice. Check out the Yahoo article on RAG and the lawsuit
4. How has the Chicago Tribune responded to Perplexity's claim that it didn’t train its AI models on Tribune content?
The Chicago Tribune insists Perplexity’s tools utilize verbatim content from its platform, despite claims to the contrary by the company. Engadget outlines this legal challenge
5. Is this lawsuit unique, or are there similar cases against AI companies?
The case is part of a growing trend, with media organizations like Dow Jones, Reddit, and others filing similar lawsuits against AI companies over content usage. Discover related legal battles in the American Bazaar article
6. Does Perplexity AI have other relationships with publishers?
Unlike collaborative agreements like Google’s publisher partnerships, the Tribune alleges Perplexity kept its interactions adversarial, raising concerns about responsible AI use. Review Bloomberg’s detailed analysis
7. What is Perplexity AI’s stance on bypassing paywalls?
Perplexity claims its tools generate summaries rather than verbatim reproductions, but the lawsuit suggests paywalls were bypassed for detailed content delivery. Explore insights from the Chicago Tribune’s case summary
8. What other lawsuits is Perplexity AI facing?
In addition to the Tribune case, Perplexity has faced legal challenges from Reddit and Dow Jones for similar copyright infringement allegations. Check out related legal coverage on CNBC
9. How could AI product design be affected by cases like these?
Litigation focusing on AI's use of RAG and paywalled content may prompt stricter guidelines for digital platform design, balancing utility with copyright laws. Explore design implications in Publishers Weekly
10. What steps can startups take to avoid legal risks in AI implementation?
Startups can focus on transparent processes, ethical frameworks, and early partnership models to mitigate copyright and content use disputes. Learn more about a female entrepreneur’s perspective via Fe/male Switch
About the Author
Violetta Bonenkamp, also known as MeanCEO, is an experienced startup founder with an impressive educational background including an MBA and four other higher education degrees. She has over 20 years of work experience across multiple countries, including 5 years as a solopreneur and serial entrepreneur. Throughout her startup experience she has applied for multiple startup grants at the EU level, in the Netherlands and Malta, and her startups received quite a few of those. She’s been living, studying and working in many countries around the globe and her extensive multicultural experience has influenced her immensely.
Violetta Bonenkamp's expertise in CAD sector, IP protection and blockchain
Violetta Bonenkamp is recognized as a multidisciplinary expert with significant achievements in the CAD sector, intellectual property (IP) protection, and blockchain technology.
CAD Sector:
- Violetta is the CEO and co-founder of CADChain, a deep tech startup focused on developing IP management software specifically for CAD (Computer-Aided Design) data. CADChain addresses the lack of industry standards for CAD data protection and sharing, using innovative technology to secure and manage design data.
- She has led the company since its inception in 2018, overseeing R&D, PR, and business development, and driving the creation of products for platforms such as Autodesk Inventor, Blender, and SolidWorks.
- Her leadership has been instrumental in scaling CADChain from a small team to a significant player in the deeptech space, with a diverse, international team.
IP Protection:
- Violetta has built deep expertise in intellectual property, combining academic training with practical startup experience. She has taken specialized courses in IP from institutions like WIPO and the EU IPO.
- She is known for sharing actionable strategies for startup IP protection, leveraging both legal and technological approaches, and has published guides and content on this topic for the entrepreneurial community.
- Her work at CADChain directly addresses the need for robust IP protection in the engineering and design industries, integrating cybersecurity and compliance measures to safeguard digital assets.
Blockchain:
- Violetta’s entry into the blockchain sector began with the founding of CADChain, which uses blockchain as a core technology for securing and managing CAD data.
- She holds several certifications in blockchain and has participated in major hackathons and policy forums, such as the OECD Global Blockchain Policy Forum.
- Her expertise extends to applying blockchain for IP management, ensuring data integrity, traceability, and secure sharing in the CAD industry.
Violetta is a true multiple specialist who has built expertise in Linguistics, Education, Business Management, Blockchain, Entrepreneurship, Intellectual Property, Game Design, AI, SEO, Digital Marketing, cyber security and zero code automations. Her extensive educational journey includes a Master of Arts in Linguistics and Education, an Advanced Master in Linguistics from Belgium (2006-2007), an MBA from Blekinge Institute of Technology in Sweden (2006-2008), and an Erasmus Mundus joint program European Master of Higher Education from universities in Norway, Finland, and Portugal (2009).
She is the founder of Fe/male Switch, a startup game that encourages women to enter STEM fields, and also leads CADChain, and multiple other projects like the Directory of 1,000 Startup Cities with a proprietary MeanCEO Index that ranks cities for female entrepreneurs. Violetta created the "gamepreneurship" methodology, which forms the scientific basis of her startup game. She also builds a lot of SEO tools for startups. Her achievements include being named one of the top 100 women in Europe by EU Startups in 2022 and being nominated for Impact Person of the year at the Dutch Blockchain Week. She is an author with Sifted and a speaker at different Universities. Recently she published a book on Startup Idea Validation the right way: from zero to first customers and beyond, launched a Directory of 1,500+ websites for startups to list themselves in order to gain traction and build backlinks and is building MELA AI to help local restaurants in Malta get more visibility online.
For the past several years Violetta has been living between the Netherlands and Malta, while also regularly traveling to different destinations around the globe, usually due to her entrepreneurial activities. This has led her to start writing about different locations and amenities from the POV of an entrepreneur. Here’s her recent article about the best hotels in Italy to work from.
About the Publication
Fe/male Switch is an innovative startup platform designed to empower women entrepreneurs through an immersive, game-like experience. Founded in 2020 during the pandemic "without any funding and without any code," this non-profit initiative has evolved into a comprehensive educational tool for aspiring female entrepreneurs.The platform was co-founded by Violetta Shishkina-Bonenkamp, who serves as CEO and one of the lead authors of the Startup News branch.
Mission and Purpose
Fe/male Switch Foundation was created to address the gender gap in the tech and entrepreneurship space. The platform aims to skill-up future female tech leaders and empower them to create resilient and innovative tech startups through what they call "gamepreneurship". By putting players in a virtual startup village where they must survive and thrive, the startup game allows women to test their entrepreneurial abilities without financial risk.
Key Features
The platform offers a unique blend of news, resources,learning, networking, and practical application within a supportive, female-focused environment:
- Skill Lab: Micro-modules covering essential startup skills
- Virtual Startup Building: Create or join startups and tackle real-world challenges
- AI Co-founder (PlayPal): Guides users through the startup process
- SANDBOX: A testing environment for idea validation before launch
- Wellness Integration: Virtual activities to balance work and self-care
- Marketplace: Buy or sell expert sessions and tutorials
Impact and Growth
Since its inception, Fe/male Switch has shown impressive growth:
- 5,000+ female entrepreneurs in the community
- 100+ startup tools built
- 5,000+ pieces of articles and news written
- 1,000 unique business ideas for women created
Partnerships
Fe/male Switch has formed strategic partnerships to enhance its offerings. In January 2022, it teamed up with global website builder Tilda to provide free access to website building tools and mentorship services for Fe/male Switch participants.
Recognition
Fe/male Switch has received media attention for its innovative approach to closing the gender gap in tech entrepreneurship. The platform has been featured in various publications highlighting its unique "play to learn and earn" model.
