6 Guidelines that will Help You as a CEO with Jennifer Hyman, Co-Founder and CEO of Rent the Runway

Have you ever wondered what it takes to be a successful CEO? Or how to make changes once you’ve realized your business idea isn’t working? In this post we address questions about iteration, hiring the right employees, and where to find inspiration.

Jennifer Hyman, Co-Founder and CEO of Rent the Runway recently shared her hard-earned knowledge at Project Entrepreneur 2016 Weekend Intensive. Here are six guidelines she has learned that will help you chart your company’s course.

1. Hire people you like.

When staffing your company, hire people that you actually like. Hyman says that in the early stages of Rent the Runway, she hired people she genuinely enjoyed being around. Those individuals then, in turn, hired people whom they liked. This fostered a supportive and trusting family-like culture within the company.

As the company grew, however, Hyman started to hire people who were smart and hardworking but weren’t necessarily people she enjoyed being around. She noticed over time that her happiness began to suffer and that the culture of the company had shifted. Eventually, Hyman had to refocus on her original mantra of hiring employees she liked.

Even as your company grows, Hyman strongly believes that you deserve to have chemistry with the people who work for you. It’s not a selfish desire. Your company and its employees will be better for it.

2. Iteration is unavoidable and is the expectation.

Hyman says, “None of your businesses today are going to be what is successful. None. You will be iterating dozens and dozens of times.” Don’t expect to get to your goal in a straight line. Have the expectation that whatever your business idea is, it’s likely going to fail. It’s what you do from there that is most important. Ask yourself “What elements of your business or product failed?” and “How do you make sure you are testing different variables on what failed in order to make it successful?”

You may need to pivot to a completely different idea altogether. Or you may pivot certain aspects of your current business. Hyman talks about how she initially launched her business as an accessory subscription service. After she saw the churn numbers a few months later, she realized that people weren’t using her accessory service.

Hyman reached out to her customers to find out what was wrong with the product and what she should iterate. During this process, she learned that it’s much better to ask these questions in person, rather than over the phone. People are more likely to be honest if you talk to them individually and in person. She also cautions against using focus groups because there is often the element of groupthink.

3. Be aware of the difference between iteration and versioning.

Hyman says “An iteration inherently implies that the thing you are iterating doesn’t work and you’re iterating it towards success.” Versioning, according to Hyman, is a very different concept. Versioning is taking an aspect of something that is already successful and trying to address a new segment of the population. Each different version is much more likely to be successful.

4. Have passion for your ideas.

Hyman credits the passion she feels for her product as the key to keeping her going even when others didn’t believe in it. Getting to that vision is crucial for every founder and CEO. Having an end goal that you truly believe in will help you to convince anyone of your idea’s value.  

5. Inspiration comes from unexpected places.

Hyman explains, “Iteration doesn’t take money. It takes people thinking about the problem, throwing up the problem against the wall, coming up with a million different solutions, 99% of which aren’t going to work and continuing to hear the solutions from the most unlikely of sources.”

Take the chance to talk to anyone you can about what you are trying to solve. Hyman says many of the answers to her most difficult problems haven’t come from her but from a junior member of staff, a customer, or someone completely unexpected. You never know who is going to give you a great idea.

6. One day at a time.

Hyman suggests that it can be really overwhelming to think about everything you need to do in the next year, or even in the next month. Don’t think about timing, just focus on getting through today.


Hyman’s advice comes from her #PEIntensive16 workshop, “The Art of Iteration,” along with Monique Woodard, Co-Founder of Black Founders and an investor at 500 Startups. Listen to the entire workshop on episode 9 of our podcast. For more expert inspiration, read 3 Tips To Developing Your Company’s Brand with Hilary Folger, CEO of Sparkfire, a branding company that specializes in early stage businesses.