Podcast Summary: Investing in the Next Generation of Brands
Your Next Move is a compelling podcast series produced by Inc. Magazine in partnership with Capital One Business, featuring in-depth conversations with innovative entrepreneurs and business leaders. In the August 6, 2024 episode titled "Investing in the Next Generation of Brands," host Beatrice Dixon engages in a profound dialogue with Jenny Fleiss—co-founder of Rent the Runway, head of Walmart's incubator Jet Black, and venture partner at Volition Capital. This episode delves into Jenny’s entrepreneurial journey, her strategies for overcoming challenges, and her insights on investing in emerging brands.
1. The Founding Story of Rent the Runway
The conversation opens with Jenny recounting the inception of Rent the Runway, a pioneering service addressing the dilemma of attending multiple events without an overflowing wardrobe or endless budget. The idea germinated from a personal anecdote shared by her co-founder, Jennifer Hyman, highlighting the need for accessible designer attire.
Notable Quote:
"We started with a lunch conversation about my sister Becky buying a $2,000 dress despite financial constraints and the feeling that existing dresses were ‘dead to her’ due to social media." [02:06]
Jenny and Jennifer, both business school students, saw an opportunity to meld their complementary skills to solve a genuine consumer pain point. Their vision was to create a platform that benefits both designers and consumers, moving beyond the limitations of fast fashion by offering a sustainable, stylish alternative.
2. Navigating Rejection and Building Resilience
A pivotal moment in Jenny’s entrepreneurial journey was her initial meeting with designer Diane von Furstenberg. Contrary to their hopes, Diane was unimpressed with the Rent the Runway concept, delivering harsh feedback that left Jenny feeling demoralized.
Notable Quote:
"She hated the concept and that was incredibly demoralizing… It was one of those moments where you really value having a co-founder there." [05:54]
Despite the setback, Jenny emphasizes the importance of having a supportive co-founder. Jennifer’s encouragement to pivot and refine their pitch was instrumental in transforming adversity into an opportunity for growth. This experience underscored the necessity of resilience and adaptability in the face of entrepreneurial challenges.
3. Persistence in Building Designer Relationships
Securing partnerships with designers was neither quick nor easy. Jenny highlights the relentless effort required to gain trust and collaboration from high-profile designers, often necessitating numerous meetings and demonstrations of their commitment.
Notable Quote:
"No doesn't mean no. It means not right now." [08:37]
This mantra underscores the importance of persistence. Jenny and her team averaged ten meetings per designer before securing a partnership, showcasing their unwavering dedication to building Rent the Runway's network. This approach was crucial in establishing credibility and fostering long-term relationships within the fashion industry.
4. Investing in Brand and Customer Experience
Jenny discusses the strategic investments Rent the Runway made in brand building and customer experience, which were pivotal in differentiating the company from competitors. By aligning their brand with values such as female empowerment and sustainability, they cultivated a loyal customer base driven by word-of-mouth marketing.
Notable Quote:
"Make sure that you have a brand that resonates with your core customer base." [12:09]
Rent the Runway focused on creating an aspirational brand that women wanted to talk about, leveraging the power of personal storytelling and shared values. This focus not only enhanced customer loyalty but also positioned the company as a leader in sustainable fashion.
5. Transitioning from Startup to Corporate and Investing
Jenny's transition from founder to corporate leadership at Walmart’s Jet Black and her role as a venture partner at Volition Capital illustrate her versatility and strategic acumen. She brings a unique perspective by bridging the agility of startups with the structured environment of large corporations.
Notable Quote:
"Blend of understanding the world of corporate but also know what it is to be a scrappy entrepreneur." [26:03]
At Walmart's Jet Black, Jenny was tasked with steering the company into the digital age, leveraging her entrepreneurial mindset to innovate within a traditionally corporate framework. Her multifaceted experience enhances her ability to identify and invest in promising startups with potential for significant impact.
6. Strategies for Motivating Teams Across Environments
Balancing startup dynamism with corporate structure requires nuanced leadership. Jenny shares her strategies for motivating teams and fostering alignment across different organizational cultures.
Notable Quote:
"Finding ways to bridge the traditional corporate mindset with the innovative spirit of startups is critical." [26:19]
She emphasizes the importance of creating a cohesive team culture that values both innovation and operational efficiency, ensuring that employees remain engaged and motivated regardless of the organizational context.
7. Advice for Entrepreneurs Seeking Venture Capital
When discussing venture capital, Jenny provides actionable advice for entrepreneurs preparing to approach investors. She stresses the importance of validating the business concept with real customers and leveraging trusted introductions to break through the noise.
Notable Quote:
"Show that you've got the hustle... and find the right way into the right investor." [34:41]
Jenny advocates for a hands-on approach—demonstrating traction through customer engagement and utilizing networks to secure introductions from reputable sources. This strategy not only builds credibility but also increases the likelihood of securing investment.
8. Supporting Female Founders and Mentorship
A significant portion of the conversation focuses on Jenny’s commitment to empowering female entrepreneurs. She highlights the systemic challenges women face in the investment landscape and the importance of mentorship and support networks.
Notable Quote:
"I am more inclined to try to mentor and advise and be helpful to women... because I was given so much of that help." [46:42]
Through initiatives like the Rent the Runway Foundation and partnerships with organizations like UBS, Jenny actively works to create opportunities for female founders, providing mentorship, resources, and access to capital.
9. The Future: Supporting the Next Generation of Entrepreneurs
Concluding the conversation, Jenny expresses her dedication to fostering the growth of future entrepreneurs. Her vision encompasses not only financial investment but also strategic guidance and mentorship, ensuring that the next wave of brands is well-equipped to thrive in a rapidly evolving market.
Notable Quote:
"My next move is and continues to be just helping to support this next generation of entrepreneurs." [47:16]
Jenny's commitment to nurturing new talent underscores her role as a catalyst for innovation and growth within the entrepreneurial ecosystem.
Conclusion
The episode "Investing in the Next Generation of Brands" provides a rich narrative of Jenny Fleiss's journey from co-founding Rent the Runway to leading corporate innovation at Walmart and investing in emerging startups. Her insights on resilience, strategic investment, and the importance of supporting female entrepreneurs offer valuable lessons for aspiring founders and investors alike. Jenny’s balanced perspective, blending entrepreneurial grit with corporate strategy, positions her as a formidable leader and mentor in the business world.
Notable Quotes Recap:
- "No doesn't mean no. It means not right now." [08:37]
- "Make sure that you have a brand that resonates with your core customer base." [12:09]
- "Blend of understanding the world of corporate but also know what it is to be a scrappy entrepreneur." [26:03]
- "Show that you've got the hustle... and find the right way into the right investor." [34:41]
- "I am more inclined to try to mentor and advise and be helpful to women... because I was given so much of that help." [46:42]
- "My next move is and continues to be just helping to support this next generation of entrepreneurs." [47:16]
This structured and detailed summary captures the essence of Jenny Fleiss’s experiences and insights shared during the podcast, providing a comprehensive overview for listeners and non-listeners alike.