Jenn’s Fashionpreneur Column: Best and Worst Advice She’s Received

In the latest installment of Jenn’s Fashionpreneur column on, she talks about the best and worst pieces of advice she’s received as an entrepreneur.



Rule number one of entrepreneurship is that the second you tell someone that you are thinking about starting a company, the floodgates of advice will open. Suddenly, friends, distant relatives and colleagues will frame themselves as experts on just about anything to create the opportunity to give you their opinion. This all stems from rule number one about people which is that they love to hear themselves talk (in fact, in any negotiation or interview, the person that speaks most believes that she has the upper hand). Since I had the idea for Rent the Runway nearly three years ago, my co-founder Jenny Fleiss and I have solicited and received lots of advice. The trick is the ability to decipher good advice from bad. So, in the efforts of saving all of you the trouble, I thought it best to list some of the very best and very worst advice I’ve received.


The Good


Find a partner. Starting a company is really, really hard. Not just from a workload or execution standpoint, but the emotional roller coaster is intense. Thank god that since day one, I have had an incredible partner to share the lows and incredible highs with. The day we launched (Nov 9, 2009), Rent the Runway was covered on the front page of the business section of the New York Times, an incredibly surprising and exciting moment. But, by far, the very best moment of that day was hugging, screaming and jumping up and down with Jenny when we came into the office. Every experience is better when it is shared!


Get your nails done. Yes, seriously! I was at a very important designer brand which shall forever
remain nameless, and the head of the brand pulled me aside after the meeting and said: “Jenn, I know you’re new to this industry so I want to tell you something very important. Your nails are RUDE and inappropriate.” (My three-day old manicure had a few chips). At first I was floored–like for real, the leader of one of the most prestigious brands ever is that superficial and has that little to do than to comment on my manicure?! But upon further reflection, I recognized and learned the lesson here: Know your audience and know your industry. The fashion industry is one where its leaders care a great deal for their personal brand – the clothes and makeup they use to present themselves to the world. If I’m going to play in their space, I have to play by their rules and respect what makes this industry fun, unique and slightly crazy :)


Sleep. One of my investors from Kleiner Perkins, Juliet de Baubigny, begins every conversation with me by asking how much sleep I got the night before. Not only is sleep important to stay healthy (and oh yes, to stay awake during intense days in the office) but the larger point is, create space for yourself to clear your mind. Some of my best ideas for how to grow Rent the Runway come when I’m not even thinking about the business – I may be at dinner with my boyfriend or at Physique or dreaming. Make time to sleep (and have a life) and the great ideas will come.


The Bad


Do not enter an industry where you have no experience. I believe that it is because Jenny and I didn’t have experience in the fashion industry that we’ve been able to rethink some fundamental assumptions about the way it works and create an entirely new category of rental. Coming from outside the industry gives you a certain degree of naivety that enables you to blindly reach for the stars. A few months after we had the idea for Rent the Runway, we were introduced to Andrew Rosen. At the time, we had little idea who he was, how Mr. Rosen almost single handedly has transformed contemporary fashion and how many brands he directs. Had we known this, we might have been too scared to take the meeting or pitch him our idea. Naivety led to a better meeting where Andrew gave us the idea for our stylist team who could educate our younger customers on what to wear to every occasion.


Write a business plan. This one is the stupidest of them all. There is no reason to write a business plan – EVER! Strategizing for months is a complete waste of time and will likely give competitors ample time to start whatever you thought was such a genius idea and beat you to the punch. The better strategy is to just go for it, make mistakes, analyze quickly and make the appropriate changes. You can learn a lot more from buying dresses at retail, running trunk shows on college campuses and testing whether women will rent dresses (they did!) than by ‘brainstorming’ or ‘market sizing’. Professors at Harvard Business School call this the minimum viable product approach. I just call it smart and way more fun.


You’ll find the best talent when you hire a recruiter and look beyond your own network. When I look at the amazing team at Rent the Runway, I am absolutely amazed by how many of our very best people came through connections (albeit, some of them quite loose). For example, we met our Vice President of Brand Marketing Lara Crystal through a woman who I had interned with the summer before at McKinsey. People from your broader network are often pre-vetted and may exhibit more passion for your concept because they also feel a deeper connection to you personally. If you’re starting a business, start first with people you trust. You’re going to spending a huge amount of time with your team so select people who speak the same language as you (figuratively, but I guess literally too!).


- Jenn