Tech Brew Ride Home — (BNS) Jennifer Hyman Of Rent The Runway

Date: October 13, 2025
Guest: Jennifer Hyman (Co-founder & CEO, Rent the Runway)
Host: Morning Brew

Episode Overview

In this episode, Jennifer Hyman shares the founding journey of Rent the Runway, diving into what it takes to build a disruptive company in a space where key industry players may initially be antagonistic. She explores her formative experiences, challenges in gaining product-market fit—both with consumers and brands—and reflects on the evolution of entrepreneurship, especially in New York City’s tech scene.

Key Discussion Points & Insights

Early Influences and Entrepreneurial Spirit

• Entrepreneurial Roots & Internet Upbringing (01:09–04:24)
  • Jennifer credits her father’s resilience and risk-taking as formative, though her family wasn’t plugged into tech.
  • “The spirit of having a crazy idea and going after it and having the resilience comes from him.” — Jennifer Hyman (01:32)
  • Grew up with early exposure to computers, owing to tech-involved uncles and a "computer room" at home.
  • Reminisces about her AOL screen name ‘Broadway Jen’ and being among the early Facebook invitees while at Starwood Hotels.

Learning Across Industries (04:47–09:57)

• Gaining Skills in Disrupted Fields

  • Jennifer’s early interest in travel post-9/11 primed her to embrace innovation during industry turmoil.
  • Pitched and helped launch the first honeymoon registry for Starwood, enabling couples to let guests fund their honeymoon experiences.
  • Takeaway: “All that entrepreneurship is really is having a big idea, then corralling and getting a team…to get excited about that idea cross functionally and help you implement it.” (06:13)

• No Early “Entrepreneur” Label

  • In the early 2000s, “entrepreneur” wasn’t an aspirational or mainstream path—finance and consulting reigned.
  • “Entrepreneurs are sort of the rock stars now these days. There was no model for that… If you wanted to get rich…you go to Wall Street or something.” — Host (09:25)

Shifts in Career Ideals & Company Culture (09:57–13:10)

• Prestige Paths and Changing Attitudes
  • Jennifer recalls Harvard grads flocking to “strategic planning programs” over startups.
  • Now, she views “strategy” as a red flag:
    • “If I see that word on anyone’s resume, I won’t hire them. It’s like the worst thing you could be is in strategy—it means you do nothing.” — Jennifer Hyman (11:48)
  • Notes a cultural evolution: “There was no notion that you could invent a career for yourself…Now…people are dreaming big for what they want to do with their lives.” (12:20)

Pre-Rent the Runway: Career Arc (13:10–16:16)

• IMG & Discovering Fashion’s Flaws
  • Experience at IMG exposed her to the unglamorous realities for most designers—struggling to turn a profit.
  • Valued the importance of company culture after surviving a toxic environment at IMG.
• Business School & Seeing the Light
  • Interned at McKinsey—landmark for prestige, not passion.
    • “McKinsey…is where smart people go to die. Like, this is the opposite and antithesis of my soul…” — Jennifer Hyman (15:16)
  • The realization pushed her into entrepreneurship.
  • Thanksgiving break: sparks the Rent the Runway idea after her sister’s wardrobe dilemma.

The Birth of Rent the Runway (18:35–22:45)

• Founding Idea: Social Media & Fashion Needs

  • Sister’s $4,000 dress purchase (and Facebook’s “outfit fatigue”) exposes the need for wardrobe variety without financial strain.
  • Jennifer saw rental as an affordable middle ground between fast fashion and high-end brands.

• Fast Action & Cold Outreach

  • Within days, Jennifer and co-founder Jenny Fleiss pitch Diane von Furstenberg—who is initially resistant.
    • “She actually hated the idea and said it would cannibalize her sales and ruin her brand and who the hell was I…” — Jennifer Hyman (19:56)
  • In conversation, DVF reveals her real customer base is older than the brand's image—offering a potential win-win for relevance and reach.

• “That became the seed of—oh wait, this has not only a customer value prop, it has an industry value prop...” (21:18)

• MVPs and Testing Hypotheses:

  • Despite the 2008 recession, Jennifer and Jenny find inspiration from other HBS entrepreneurs (e.g., Gilt Groupe) and the retail industry’s crisis.
  • “It was the most interesting time to kind of come into this industry and disrupt because people are open to new business models because of how badly the traditional business model is doing.” (22:35)

Fundraising as Outsiders (22:45–25:12)

• Naivete and the Unfamiliar Startup Ecosystem
  • Had no real understanding of VC culture—chose Bain Capital Ventures over Benchmark simply for name familiarity.
    • “We ended up going with Bain Capital Ventures because I had never heard of Benchmark…and we’d heard of Bain because all the smartest people at HBS had worked for Bain.” (24:13)

Iterative Product Development & Customer Fit (25:22–27:55)

• MVP Experiments
  • Pop-ups at Harvard and Yale to test consumer willingness to rent dresses, with and without try-ons, and then as a virtual PDF “catalog.”
  • Introduced key features (like sending a second size for free) based on prototype performance.
  • “That MVP testing helped us figure out what conversion might end up being and what features we needed to launch with...” (26:52)

Winning Over Brands & Building an Ecosystem (28:43–38:33)

• Building Designer Partnerships

  • Persistent relationship-building, repeated meetings.
  • Leveraged introductions and mentorship from NYC’s early startup ecosystem: Gilt Groupe, Bonobos, Zappos, Thrillist, etc.
    • “In every single meeting, we would always ask the person we were meeting with, who else should we be meeting with?” (29:03)

• Shaping New York’s Startup Scene

  • Early tenant in Hudson Square among rising DTC brands and tech companies, contributing to the neighborhood’s transformation.
  • Benefited from informal founder networks: “We were all friends. We would all meet up for drinks and lunches and dinners and share ideas.” (35:41)
  • Shared hiring, marketing, and company-building knowledge with other consumer startup leaders; female founder networks formed lasting partnerships and friendships.

The Unique Advantages of NYC for Startups (38:33–end)

• Why New York City?
  • Rent the Runway’s success was rooted in proximity to fashion, media, and other non-engineering talent pools.
  • “You never could have built Rent the Runway in any city beyond New York…Not every business had to be, like, hardcore technical…I was actually building a fashion company that was supported by technology and logistics.” — Jennifer Hyman (39:11)

Notable Quotes & Memorable Moments

• "All that entrepreneurship is really is having a big idea, then corralling and kind of getting a whole team of people…to get excited about that idea (and) help you implement it." — Jennifer Hyman (06:13)

• "If I see that word on anyone’s resume, I won’t hire them. It’s like the worst thing you could be is in strategy—it means you do nothing." — Jennifer Hyman (11:48)

• “McKinsey…is where smart people go to die. Like, this is the opposite and antithesis of my soul, my personality.” — Jennifer Hyman (15:16)

• “She actually hated the idea and said it would cannibalize her sales and ruin her brand and who the hell was I…” (19:56)

• Yet, insight came when DVF revealed: “…If you could build a business that made me relevant to anyone under the age of 50, that might be interesting to me and I might work with you.” (20:40)

• “That MVP testing helped us figure out what conversion might end up being and what features we needed to launch with…” (26:52)

• “We ended up going with Bain Capital Ventures because I had never heard of Benchmark before and neither had Jenny…” (24:13)

• “You needed to have the competency in fashion and merchandising and be near the industry. But think about, like, you’re starting a startup in media—like, there’s no better place to do it than the center of media. You’re starting a fintech company—oh, you’re in the financial capital of the world…” — Jennifer Hyman (39:00)

Timestamps for Important Segments

| Timestamp | Segment | |-----------|----------------------------------------------------------------------------------------| | 01:09 | Jennifer’s entrepreneurial family & early web experiences | | 06:13 | What entrepreneurship really means in practice | | 09:57 | Early 2000s: No mainstream startup/entrepreneurial path | | 13:10 | Transition from Starwood --> Wedding Channel --> IMG | | 15:16 | Realization that consulting isn’t for her; McKinsey reflection | | 18:35 | The “aha” moment that inspired Rent the Runway | | 19:56 | First pitch to Diane von Furstenberg; initial rejection and insight | | 25:22 | MVP development: pop-ups, PDF “catalog,” introducing the second-size feature | | 28:43 | Persuading brands and building designer relationships | | 35:41 | The rise of NYC’s DTC/startup ecosystem | | 38:33 | Why NYC is uniquely suited for fashion, media, and other startups | | 39:00 | Final reflection: "You never could have built Rent the Runway anywhere but New York…" |

Takeaways

• Resilience, naivete, and rapid execution can be superpowers for entrepreneurs if paired with relentless experimentation.
• Startup ecosystems thrive on open knowledge-sharing and supportive peer networks, highlighted by the collaborative NYC startup scene.
• Disruptive ideas must often win over both customers and industry incumbents; relationship-building and adaptability are critical.
• Company culture and choice of location matter deeply, shaping not just talent pipelines but also how a founder’s vision takes root.