How I Built This with Guy Raz: Advice Line Featuring Jen Hyman of Rent the Runway

Release Date: March 13, 2025

In this engaging episode of How I Built This with Guy Raz, host Guy Raz reconnects with Jen Hyman, the co-founder and CEO of Rent the Runway. Celebrating the company's 15-year milestone, Jen shares invaluable insights on leadership, scaling a business, and navigating the challenges of running a publicly traded company. The episode delves into real-time advice as Jen and Guy tackle questions from budding entrepreneurs, offering actionable strategies grounded in Jen's extensive experience.

1. Celebrating 15 Years of Rent the Runway

Jen Hyman reflects on Rent the Runway's evolution from its inception to becoming a publicly traded company. Founded with the innovative idea of renting high-fashion designer clothing, the company has transformed the rental model to encompass everyday casual wear alongside special occasion attire.

Jen Hyman [04:10]: “It's honestly my favorite piece of media, my favorite podcast I've ever done. It's going to be the thing that I'm the proudest of my kids listening to someday.”

Jen proudly highlights Rent the Runway's historic move to go public, emphasizing that it was the first company to do so with a female CEO, COO, and CFO.

Jen Hyman [04:51]: “We were the first company in history to go public with a female CEO, COO and CFO. And it's amazing. Who would have thought?”

2. Adapting and Scaling the Business Model

As Rent the Runway enters its 15th year, Jen discusses the company's strategic pivots and the normalization of clothing rentals in mainstream culture. She explains how the business has expanded from catering to special events to integrating casual, everyday wear, thereby broadening its customer base.

Jen Hyman [05:37]: “Now rental has become so much more normalized... So I think we've reached a different point in the cycle from early adopters into more of a mainstream behavior.”

3. Leadership Lessons from a Public Company CEO

Navigating the complexities of a publicly traded company comes with its unique set of challenges. Jen candidly addresses the scrutiny that comes with fluctuating stock prices and the importance of maintaining a low ego in leadership.

Jen Hyman [08:18]: “Our stock price has only gone down. There's scrutiny, there are questions.”

Despite the pressure, Jen emphasizes her resilience and the advantage of having a low ego, which she attributes to the company's sustained growth.

Jen Hyman [09:15]: “I don't need that validation that I think a lot of CEOs need. And I think that that is my competitive advantage... my biggest belief over 15 years is the person who stays in the game the longest wins.”

4. The Advice Line: Supporting Emerging Entrepreneurs

Throughout the episode, Guy Raz and Jen Hyman engage with callers seeking advice on various business challenges. Their discussions offer deep dives into specific issues, blending practical strategies with motivational insights.

Caller 1: Sarah Bell of Esky Wright

Sarah Bell, co-founder of Esky Wright, seeks guidance on balancing artisanal production with scalability while maintaining product authenticity.

Jen Hyman [14:10]: “I think that using a PR head is tricky because you don't know whether people responded to that because you are founders that are based in Massachusetts, or whether the product itself was made and sourced locally.”

Jen advises Sarah to gather authentic customer feedback to determine if the local craftsmanship is a valued aspect of the product, emphasizing the importance of "small data" conversations over large surveys.

Jen Hyman [15:46]: “Sometimes it's the small data. It's the conversations with eight women at dinner that give you better insight than the surveys of millions.”

For scaling, Jen recommends exploring higher-margin product lines and leveraging community partnerships to drive volume.

Jen Hyman [19:52]: “My wife has that to put on.”

Caller 2: Carrie Sporer of Swear Hair

Carrie Sporer, founder of Swear Hair, a showerless shampoo, faces challenges in fundraising due to insufficient trailing revenue. She seeks strategies to bootstrap her way to a million dollars in sales without additional funding.

Jen Hyman [36:52]: “You have something here. Okay. $300,000 in sales is significant. You've got something. People like this product. You got to get it out there more.”

Jen emphasizes the importance of repeat customers and suggests diversifying revenue streams through community-oriented partnerships and leveraging existing customer bases through email marketing and subscriptions.

Jen Hyman [38:26]: “Don't ask permission. Why are you even bothering with the permission?”

She also highlights the power of free samples and grassroots marketing to build brand loyalty and drive sales growth.

Caller 3: Chabella Gomez of Chavella

Chabella Gomez, founder of Chavella, a sustainable women's wear brand, seeks advice on attracting angel investors in the capital-intensive apparel industry without a million dollars in trailing revenue.

Jen Hyman [44:13]: “What it is is it's very much relationship based... networking to figure out who those people are and to get in front of them is critical.”

Jen advises Chabella to engage with influential figures in the fashion industry, explore collaborations with established brands, and harness the power of social media platforms like TikTok to amplify brand visibility.

Jen Hyman [48:05]: “Like right now, any product can become a multi million dollar business overnight with the right kind of content.”

5. Key Takeaways and Final Insights

Throughout the episode, Jen Hyman imparts several key lessons for entrepreneurs:

• Resilience and Persistence: Staying committed to the business despite external challenges and skepticism.

  Jen Hyman [09:41]: “The person who stays in the game the longest wins.”

• Customer-Centric Approach: Prioritizing customer feedback and building products that resonate with the target audience.

• Strategic Scaling: Balancing growth with maintaining core values and product integrity.

• Networking and Relationships: Building meaningful connections within the industry to unlock opportunities and resources.

In closing, Jen reflects on her journey, offering aspirational advice to her younger self and emphasizing the importance of enjoying the entrepreneurial journey while documenting significant milestones.

Jen Hyman [50:29]: “Don't focus as much on the future. You're doing something that's so fun. Don't have anxiety about what's going to happen next quarter or next year. Enjoy today.”

Conclusion

This episode serves as a masterclass in leadership, resilience, and strategic growth. Jen Hyman's experiences with Rent the Runway provide a blueprint for entrepreneurs navigating the complexities of scaling a business while staying true to their foundational values. Through real-time advice and heartfelt reflections, listeners gain a deeper understanding of what it takes to build and sustain an iconic brand in today's dynamic market.