Startup Playbook: success through failure

Top 10 PROVEN Business Lessons from Jenn Hyman, Co-founder of Rent the Runway, That Entrepreneurs Must Know in 2025

Top 10 PROVEN Business Lessons from Jenn Hyman, Co-founder of Rent the Runway, That Entrepreneurs Must Know in 2025

In the ever-evolving world of fashion and technology, Jenn Hyman has emerged as one of the most influential leaders. As the co-founder of Rent the Runway, she has disrupted not just the retail industry but also the very way people think about ownership, sustainability, and access to luxury. From starting a subscription-based clothing rental company alongside Jennifer Fleiss in 2009 to taking her company public, Hyman's entrepreneurial journey is filled with lessons that every business owner and startup founder can apply in 2025.
Try our AI Grant Finder and Application Writer to quickly find an EU grant that is right for your startup, and have it write a draft of your application.
This article delves into 10 proven lessons from Hyman’s leadership journey, offering actionable insights, common mistakes to avoid, and tools to optimize your strategy. Whether you're scaling a startup, navigating a challenging growth phase, or brainstorming your next big idea, these lessons are your must-have blueprint for success.

Why Jenn Hyman's Leadership Is Relevant in 2025

Jenn Hyman didn’t just revolutionize how people approach fashion; she created an entirely new consumer behavior. In an era where sustainability and experiential services are at the forefront, Rent the Runway's model aligns perfectly with global trends. According to recent studies, 75% of Gen Z consumers prefer access over ownership, a shift Hyman identified and capitalized on years ago.
Her lessons aren't limited to the fashion industry. From fundraising and scaling to team management and customer obsession, Hyman’s strategies offer invaluable takeaways for businesses across industries.

Top 10 Proven Lessons from Jenn Hyman

1. Leverage Customer Insights to Solve Real Problems

When Jenn Hyman first conceived Rent the Runway, it was based on a conversation she had with her sister, who lamented having nothing to wear to a wedding despite owning a closet full of clothes. This "aha moment" sparked the idea for a subscription rental service that filled a genuine need in the market.
Entrepreneur Tip: Use customer insights directly to shape your product or service. One innovative tool to extract and analyze insights is the F/MS YouTube Transcript Generator. It allows you to easily extract transcripts from customer feedback videos, panel discussions, or trend forecasts. You can even translate content into 125+ languages and leverage AI prompts to summarize data for actionable insights.

2. Build a Business Model Around Accessibility and Affordability

Rent the Runway made luxury affordable. Their business model gives customers access to high-end fashion at a fraction of the cost. As of 2025, their rental and subscription services cater to a diverse audience, proving that accessibility is key to scalability.

3. Fundraising as a Relationship-Building Process

Hyman raised multiple funding rounds by pitching her revolutionary concept and building trust with investors. From partnering with top VCs like Kleiner Perkins to achieving a valuation of over $1 billion, her fundraising journey reflects perseverance and strategy.
👩‍💻 Did You Know? Access detailed funding timelines for companies like Rent the Runway on platforms like Crunchbase.

4. Sustainability Isn’t Optional

Hyman positioned Rent the Runway as a pioneer in sustainable fashion. By promoting a "shared economy" model, she highlighted the environmental benefits of reducing unnecessary clothing production.
📊 Statistic: The apparel rental market is projected to grow at 10.6% CAGR from 2023 to 2028, fueled by consumer demand for greener choices. Entrepreneurs in 2025 must integrate such consumer expectations into their business models.

5. Create a Scalable Tech Infrastructure

Rent the Runway excels due to its tech platform, which manages inventory, logistics, and customer data seamlessly. Hyman’s focus on operational efficiency through technology has been a game-changer.

6. Customer Obsession Drives Loyalty

From offering dry cleaning to seamless returns, Rent the Runway has always prioritized the customer's experience. Their "Unlimited" subscription program is a testament to customer-centricity, providing users with an abundance of options.

7. Adaptability in the Face of Challenges

Rent the Runway faced significant challenges during the pandemic as demand for occasion wear plummeted. Hyman quickly pivoted, focusing on casual and work-from-home attire rentals. Flexibility saved the business.

8. Diversity Builds Stronger Teams

As CEO, Jenn Hyman prioritized making Rent the Runway one of the first subscription-based companies to offer flexible and comprehensive parental leave, highlighting her commitment to inclusivity.
🤝 Entrepreneur Action: Build diverse teams and inclusive workplaces. Consider implementing employee-first policies like flexible schedules and gender-neutral parental leave programs.

9. Invest in Your Brand's Storytelling

Rent the Runway thrives not just because of its services but also due to its strong brand story. Consumers engage with the brand because they align with its mission of sustainability, inclusivity, and luxury accessibility.

10. Continuous Learning Is Key

As a Harvard alum, Jenn Hyman continually emphasizes the importance of learning and adapting. Rent the Runway’s evolution reflects a deep understanding of changing consumer behaviors and technological advancements.
Exclusive Resource: Want to keep up with tools that simplify business learning and adaptation? Try our F/MS AI Article Writer. It’s a game-changing tool designed to help entrepreneurs automate and optimize their business and SEO strategies by generating content that ranks not only on search engines but also within AI tools like ChatGPT.
Chat with your AI friend PlayPal, and experience a whole new level of companionship! Discover fun conversations, advice, and endless support—all at your fingertips! Chat with PlayPal NOW!

How to Apply Jenn Hyman’s Lessons

Step 1: Evaluate your business's alignment with current market trends like sustainability or shared economy models.
Step 2: Use customer insights and AI tools like the F/MS YouTube Transcript Generator to analyze market gaps.
Step 3: Build an operationally efficient tech platform to scale seamlessly.
Step 4: Focus on storytelling to connect deeper with your audience.
Step 5: Foster diversity and adaptability within your team.

Common Mistakes Entrepreneurs Must Avoid

  1. Ignoring Market Trends: Not aligning with consumer demand can quickly render a business irrelevant.
  2. Over-reliance on Short-Term Gains: Hyman’s success stems from long-term planning and adaptability.
  3. Neglecting Sustainable Practices: Consumers are increasingly aligning their buying decisions with their values - don’t miss that trend!

Wrapping Up

Jenn Hyman’s entrepreneurial journey offers a masterclass in building a business that solves real-world problems while embracing innovation and sustainability. Whether you’re a budding entrepreneur or an established founder, these 10 lessons from Jenn Hyman can help you optimize your operations, connect with customers, and scale smartly in 2025.
🔗 Bonus Tool: Ready to dominate search rankings and grow your business? Discover the F/MS AI Article Writer today and let AI with human oversight take your SEO efforts to the next level.
Dreaming of startup success but too scared to get started?

Join the Fe/male Switch women-first startup game and turn that dream into your reality. With tailored guidance, support networks, and a plethora of resources, we'll nurture your ascent to the startup stratosphere! And we have AI co-founders, PlayPals!

Join F/MS now.
Aspiring to disrupt industries might seem daunting, but with insights from leaders like Jenn Hyman and the right tools, you can navigate challenges and carve your own path to success.

FAQ on Top Business Lessons from Jenn Hyman

1. How did Jenn Hyman come up with the idea for Rent the Runway?
Jenn Hyman conceived Rent the Runway after a conversation with her sister, who lamented having nothing to wear for a wedding despite owning a closet full of clothes. This insight revealed a real consumer need for clothing rental services. Learn more about Jenn Hyman
2. Why is sustainability central to Rent the Runway's business model?
Sustainability is a core aspect of Rent the Runway, promoting shared economy practices to reduce overproduction and waste in fashion. The rental industry is aligned with growing consumer demand for eco-friendly choices. Explore Rent the Runway’s mission
3. What challenges did Jenn Hyman face during the pandemic?
During the pandemic, demand for occasion wear rentals declined sharply, but Jenn Hyman strategically pivoted the business to focus on casual and work-from-home attire, showcasing Rent the Runway’s adaptability. Discover Jenn Hyman’s leadership insights
4. How did Jenn Hyman approach fundraising for Rent the Runway?
Jenn Hyman built trust with investors through her innovative business model and persistence, securing funding from top venture capital firms, including Kleiner Perkins. Explore funding details on Crunchbase
5. Why is customer experience key to Rent the Runway’s success?
From dry cleaning services to seamless returns, Rent the Runway prioritizes customer convenience and loyalty, making client satisfaction a cornerstone of its value proposition. Learn more about Rent the Runway’s customer programs
6. How does Rent the Runway integrate technology into its operations?
The company leverages a scalable tech platform for inventory management, logistics, and customer data optimization, ensuring operational efficiency and continued growth. Explore Rent the Runway’s tech infrastructure
7. Can I use AI to write SEO-optimized articles that help my brand grow?
Most business owners don't understand how SEO works, let alone how to use AI for writing blog articles. That's why for busy business owners there's a great free tool that doesn't require much knowledge. Write articles for free
8. What role does diversity play in Jenn Hyman’s leadership?
Jenn Hyman championed inclusivity at Rent the Runway by implementing flexible parental leave policies and fostering an employee-first workplace culture. Learn more about Jenn Hyman on LinkedIn
9. Why is storytelling important for Rent the Runway’s brand?
Rent the Runway’s strong brand story emphasizes sustainability, inclusivity, and luxury accessibility, helping the company connect deeply with its target audience. Discover strategies for successful brand storytelling
10. What can entrepreneurs learn from Jenn Hyman’s journey?
Jenn Hyman’s trajectory teaches entrepreneurs to stay adaptable, leverage customer insights, and align business models with global trends like sustainability and accessibility. Explore Jenn Hyman’s entrepreneurial story

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.
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 and launched a Directory of 1,500+ websites for startups to list themselves in order to gain traction and build backlinks.
2025-04-22 15:33 Top Female Entrepreneurs