Rent the Runway cofounder Jenny Fleiss joins Volition Capital

After launching unicorn clothing-rental startup Rent the Runway out of Harvard Enterprise Faculty with cofounder Jennifer Hyman and launching private procuring service Jetblack out of Walmart’s retail incubator and funding arm, Jenny Fleiss is coming into a brand new chapter. Beginning tomorrow, she will likely be becoming a member of Boston-based progress fairness agency Volition Capital as a enterprise associate.

We caught up together with her to speak retail traits, what she appears for in a founder, and leveling the enterprise capital taking part in discipline for ladies and minorities.

The interview has been edited and condensed.


Quick Firm: You based Rent the Runway in 2009 with present CEO Jennifer Hyman. How did you divide the work?

Jenny Fleiss: Throughout the first few years, Jenn and I actually divided and conquered. [We] every wore a number of hats. For the first three to 4 years, she did loads of the exterior work, like [forging] designer relationships, consumer-facing gross sales, and advertising. I did loads of the back-of-house work like dealing with logistics, know-how, investor relations, and getting an HR and authorized system arrange. Jenn is [good at] huge strategic visionary excited about the place’s the puck going 5 years from now. And I’m like: Let’s break this down. What are we doing this week? Our talent units fell into these sorts of patterns. Now it’s one thing that I search for once I spend money on founding groups.

FC: You left Rent the Runway for Walmart in 2018, the place you finally ran experimental private procuring service Jetblack. When did you resolve it was the proper time to depart?

JF: I used to be nonetheless itching for that early-stage entrepreneurial vitality that I felt in the early days of Rent the Runway. I felt it once I was making an attempt to study dry cleansing and establishing our warehouse. I felt it once I was testing subscriptions. Jenn knew this about me. Leaving was simpler as a result of we’ve all the time been so direct and we had some trustworthy discussions about it.

FC: You point out lacking a scrappy setting, however Walmart is an enormous, well-established firm. What attracted you to the position?

JF: Going to a Fortune One retailer and leveraging my entrepreneurial talent set at a second when Walmart was making digital commerce a precedence and placing main belongings and sources towards it was an enormous draw. They have been leaning in and had simply purchased Jet for 3.3 billion. As an entrepreneur, you actually wish to have influence, so the capability to have influence at such an enormous scale was actually thrilling. And financing was taken care of, in addition to the authorized, HR, and monetary techniques. You might skip over lots and simply get to the meat of the venture.

FC: What have been a few of the challenges you confronted at Walmart?


JF: I needed to get buy-in from the a number of stakeholders. That basically nonetheless does matter in an enormous firm. For those who’re asking for an enormous finances and making an attempt to leverage issues like the provide chain of Walmart as a result of it’s an amazing asset, it’s worthwhile to construct these relationships. I feel the common tenure at Walmart is like 10 or 15 years, so loads of them didn’t [start] on this second when digital is a precedence. And most digital companies are much less worthwhile.

Constructing that respect, assembly them, and studying different components of the enterprise was actually essential. After which recruiting the finest expertise: You possibly can’t arrange fairness in the similar means you may at a startup. [But] there’s a entire pool of expertise you may get that may’t essentially afford the danger of a startup that will tank, however is entrepreneurial. So we have been making an attempt to strike that candy spot saying, “You get to do entrepreneurial issues however with a a lot larger security web, however there’s not compensation on the fairness facet.”

FC: You left Walmart in 2020, and now you’re becoming a member of progress fairness agency Volition Capital. When do you know it was time to make the soar?

JF: I went there to be an entrepreneur, and a part of the success metric was if the enterprise will get absorbed into the broader firm. So [Walmart] used the know-how platform that we constructed to allow conversational commerce, beginning with texts.

FC: COVID-19 has modified the means we store. What traits have you ever seen in the retail house this previous yr?

JF: The main theme that I noticed is that companies that had an omni-channel technique have been the companies that have been finest ready. [An omni-channel retail strategy] offers you the rapid capability to leverage the bodily retailer as a warehouse if it’s worthwhile to, or to purchase on-line and decide up in retailer. Anybody who didn’t have a digital bone of their enterprise needed to change.

One other factor that’s been fairly attention-grabbing is considering how purchasing for discretionary gadgets has advanced. Purchasing is a social exercise. You’ve began to see issues like video commerce—traits that have been explosive in Asia—now are actually taking off right here. There’s additionally loads of entrepreneurial spirit. So many individuals began facet hustles due to COVID-19-related wants. You may have Instagram influencers selling new merchandise. It’s nearly again to the Avon mannequin of years in the past, with folks treating

like a job and making a residing off of it.

FC: Have any corporations impressed you with the means they’ve dealt with the pandemic?

JF: Peloton’s capability to scale on this second at that tempo as a comparatively younger firm is unbelievable. It’s a well-oiled machine. I’m additionally impressed with companies that it’s been powerful for. This has been a tough second for a enterprise like Rent the Runway, the place you can by no means have predicted that there could be some extent when folks didn’t want to decorate up. Seeing management that is ready to navigate a pivot, or add components to their enterprise and rally a crew and maintain their spirits excessive and regulate rapidly is a extremely good instance to me.

FC: What attracted you to Volition Capital?

JF: One is the measurement of the agency itself and that [it’s] like lower than 30 folks—it’s nonetheless lean. After which the folks to me are the most essential: It’s how I’ve made each profession choice. As a lot as I used to be making an attempt to make essential/nice-to-have career-decision matrix, the folks have been like numbers one, two, and three.


Then I used to be excited that it’s a progress fairness agency. At this second, the place valuations specifically are very excessive, it’s refreshing to discover a agency that’s centered on marrying excessive progress, huge market alternatives with the fundamentals of investing. I’ve an working background. There isn’t any one at Volition who had an working background, in order that’s one thing I may add.

FC: What are the foremost elements you consider if you resolve whether or not to spend money on a enterprise?

JF: To me, it’s all about the crew. Usually there’s nothing aside from the particular person or folks and a deck. My desire is to nonetheless vote for the folks and the crew. You’ll by no means be capable of assemble the type of ardour and monetary incentive that you simply had for that preliminary founder once more. I additionally like investing in cofounders. I discussed that Jenn and I married big-picture considering with operations considering. It is vitally uncommon to seek out each of these issues in a single particular person as a result of, to me, they’re persona traits that usually are simply fairly totally different. However there are particular person founders who can handle each.

FC: You’re considered one of 5% of girls traders. And there are different dismaying statistics: Black ladies have entry to only lower than 1% of all enterprise capital. How do you suppose the panorama will be improved?

JF: After I was at Rent the Runway, generally we have been pitching a room stuffed with 50- or 60-year-old white males and it was powerful getting them to narrate to our enterprise, which was oriented towards ladies of their 20s and 30s. However ladies affect greater than 80% of buy choices. In order an investor should you aren’t referring to that finish shopper, I don’t suppose you’ll be able to essentially have the finest portfolio or see all the alternatives or ask all the proper questions.

Change like this doesn’t occur in a single day. The extra you have got ladies on boards and in investing roles, the extra you have got corporations which can be open-minded to totally different backgrounds. Then that step by step breeds into extra ladies getting enthusiastic about working in enterprise or beginning companies after which going and dealing in enterprise the means I did.