Aug 7, 2017 · 54m · how-i-built-this
Rent The Runway: Jenn Hyman
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of How I Built This, Rent the Runway co-founder Jenn Hyman details how she transformed a disruptive fashion-rental concept into a hundred-million-dollar powerhouse while navigating startup hurdles, venture capital sexism, and executive leadership challenges.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 27% of the talking time here. How this is scored →
Guy as informed peer 3.1 Guest teaching 5.1 Guest disagreement 1.3 Guy pushing back 2.1
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 47:21 Reframing paper wealth versus reality
Jenn immediately pushes back against Guy's framing that she is a rich person, noting that paper valuation is fundamentally different from realized wealth and redirecting the conversation to the company's core mission.
Hardest push from Guy ▶ 41:23 Pressing on negative press and leadership cultureGuy refuses to let the interview remain solely a success story, directly confronting Jenn with public reporting from 2015 that labeled the company culture mean and criticized her management.
Biggest teaching moment ▶ 36:00 Exposing systemic gender bias in VC evaluationsJenn educates Guy and the audience on the subtle dynamics of venture capital, contrasting how male founders are routinely praised as brilliant visionaries and forgiven mistakes while female founders receive far less leeway.
Guy holds their own ▶ 7:20 Challenging the necessity of business schoolGuy draws on his extensive knowledge interviewing hundreds of founders to challenge why Jenn needed business school given that top entrepreneurs rarely attend and she already possessed strong momentum.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Early Career at Starwood and Overcoming Workplace Bias | 4 | 3 | 1 | 3 | Guy questions Jenn on why she decided to attend business school when she was already thriving and entrepreneurial at Starwood. Jenn explains her early career battles, including receiving sexist feedback from a female boss and wanting space to clarify her long-term goals. | |
| Finding a Co-Founder and the Closet Epiphany | 2 | 4 | 0 | 1 | Guy prompts Jenn on how she met Jenny Fleiss and conceived the idea for Rent the Runway. Jenn walks through the serendipitous Post-it introduction and the pivotal Thanksgiving epiphany when her sister refused to re-wear a dress photographed on Facebook. | |
| Pitching Diane von Furstenberg and Crashing the Office | 2 | 5 | 1 | 2 | Jenn narrates cold pitching Diane von Furstenberg and brazenly crashing her office after her assistant attempted to cancel. Guy expresses astonishment at her audacity in turning a cancellation into an in-person pitch. | |
| Validating the Rental Concept with Harvard Pop-Ups | 4 | 6 | 1 | 2 | Guy asks about consumer psychology around outfit repetition and how they validated customer demand. Jenn explains the emotional power of fashion and self-expression, recounting their empirical pop-up trials with Harvard undergraduates. | |
| Seed Funding, Craigslist Photoshoots, and Viral NYT Growth | 3 | 4 | 1 | 2 | Guy asks why Rent the Runway opted for venture capital instead of bootstrapping like Spanx or Clif Bar. Jenn explains the capital intensity of high-end inventory and describes their early viral PR stunt at a local dry cleaner. | |
| Confronting Sexism and Harassment in Venture Capital | 3 | 6 | 2 | 2 | Jenn details the condescension and overt sexual harassment she experienced from venture capitalists, deconstructing common dismissals and recounting how an investor attempted to undermine her with a board member after she rejected his advances. | |
| Board Transparency and Navigating Structural Gender Bias | 3 | 7 | 2 | 1 | Jenn explains how her board backed her against the harassing investor and expands on the insidious structural biases female founders face, noting how male founders are labeled 'visionaries' and given repeated second chances while women face strict one-strike standards. | |
| Scaling Leadership and Weathering Public Scrutiny | 3 | 6 | 2 | 3 | Guy presses Jenn on negative press in 2015 regarding high turnover and accusations of a harsh corporate culture. Jenn responds openly, detailing the double standards female leaders confront when making necessary executive termination decisions. | |
| Personal Milestones, Profitability, and Empowering Women | 4 | 5 | 2 | 3 | Guy notes that Rent the Runway has reached profitability and asserts that Jenn is now rich. Jenn pushes back on equating paper valuation with real wealth, pivoting to discuss her foundation and long-term commitment to female entrepreneurship. |
Statements from this episode (14)
Hyman: Young consumers prioritize the experience of wearing fashion over ownership
“I realized I was having a conversation with my sister about the experience of wearing an amazing dress, of walking into a party feeling self-confident and feeling beautiful, and that's what she cared about. And she didn't care about the actual ownership of the…”
Hyman: Rent the Runway originally pitched powering rentals on DVF.com
“The initial idea, actually, which, you know, we've never really told, the initial idea was, what if we could rent the dresses that she is selling on her website, so what if we powered rental for her on DVF.com?”
Hyman: Always schedule the second meeting during the first meeting
“I've always learned, you know, when you're in the first meeting, schedule the second meeting.”
Hyman: Retail's dirty secret is extremely high dress return rates
“Yeah, it's kind of the dirty secret of retail. The return rate especially of dresses and special occasion attire is extremely high.”
NYT article drove RTR's entire first-year sales projection in three weeks
“So because of hustling to get this story and the luck of ending up on the front page of the New York Times, we met our first year sales projections in three weeks”
Male VCs told Hyman they needed to consult their wives or admins
“That wasn't one investor, that was most. Let me talk to my wife, my daughter, or my admin. Those were the three, you know, target customers that we would hear.”
Jenn Hyman: One investor sexually harassed her while building Rent the Runway
“I, through the process of building Rent the Runway, was sexually harassed by one individual, and I'm happy to share that experience. However, I will say that I've had interactions with dozens and dozens of venture capitalists at dozens of firms, and this was j…”
Hyman: Harasser called Rent the Runway board member claiming CEO unresponsiveness
“And then this person decided to call one of my board members up on the phone and say, you know, Jen never responds to me. And I think that this is a real problem, and She's a really unresponsive CEO, and she's probably, if she's doing this to me, she's probabl…”
Hyman: Rent the Runway cut ties with an investor after harassment
“I proceeded to tell everyone else on my board, as well as some key executives who were working with me at Rent the Runway at the time, and the board was unbelievably supportive, and we decided that we were not going to do business anymore with this individual …”
Hyman: Society is uncomfortable describing female entrepreneurs as visionaries
“We as
A society feel uncomfortable using the words visionary or brilliant to describe women.”
Rent the Runway employs hundreds of engineers but only ten fashion staff
“You know, Rent the Runway is primarily a technology and logistics company. We have 1200 employees. 10 employees are in my fashion department. And, you know, hundreds are in my logistics department. Hundreds are in my engineering department.”
Hyman: Rent the Runway will become a multi-billion dollar company
“I was always confident that I would turn Rent the Runway into a consumer behavior that millions of people did, and that I would build a, you know, I still believe we're going to build a multi-billion dollar company.”