Industry Insight From a Self-Made Fashion Mogul

Not familiar with Natalie Massenet by name? If you’ve ever shopped online, you’re sure to have encountered her influence. She founded global fashion retailer Net-a-Porter—the premiere content and commerce destination for lovers of contemporary and designer labels—and grew it into a multimillion dollar business with a household name. Currently, Massenet is a partner and co-founder at Imaginary Ventures, a venture capital firm that’s backed cool-kid brands like Glossier, Reformation, and even Good American. In short, she’s a powerhouse entrepreneur, tech visionary, and style maven—not to mention a devoted wife and mother. As you can imagine, she’s a gold mine of sage career wisdom. In this exclusive interview with Good Times, she shares personal anecdotes and inspiring advice on paving a road to success—a must-read for any aspiring CEOs.

What were some of your earliest career aspirations, and how did those change as your professional journey began?

I loved photography, movies and writing which led me to fashion journalism. I started at Women’s Wear Daily in the Los Angeles office writing and styling shoots for both the paper and for W Magazine and fell in love with fashion media. I set my sights on wanting to be the editor of a fashion magazine in New York one day. I worked as a an editor for four years, eventually landing in London at Tatler Magazine. I had every intention of carrying on in fashion journalism when I left Tatler, but I felt like a square peg in a round hole.

That time I had, stepping back, was incredible because that’s when I started playing around on the internet and fell in love with the possibilities and how fashion could be part of this seismic shift. I never thought I would start my own company, let alone grow a business to the size it became, but if I think about it, the internet really allowed me to play with all the skills I had developed in my previous aspirations. It's all story telling, both visually and verbally, and entertainment. The retail bit really just felt like an extension of editing because as a fashion editor, I always felt like I was selecting trends and products to write about that ultimately someone would buy.

Ultimately all my aspirations and skills linked together, and still are today with Imaginary. As I see it, investing in great companies is very similar to being an editor or retailer. You have to follow your instincts, identify great trends and products, and then take a risk on them when you bet on whether it's something other people will like as well.

What would you tell women who want to follow in your footsteps? What should they do in college and beyond?

My daughter is just starting at UCLA. We have been having conversations about how to set your life up so that you can become who you are becoming and lay the best possible foundation for your future. I have advised her to:

-Take a broad view of education and to learn how to communicate as a top priority. Learning how to write is key, especially today when so much of our interaction with people is no longer in person. How you write can define you and can also inspire and educate others.

-Learning what came before is very important. Study the history of the industry you like, be it art, film, retail, politics etc. You have to know the past in order to innovate while building on the best of what came before, you can also avoid mistakes by learning about them. In the end so many industries are cyclical and referential to the past even when they are being revolutionized. I also believe you have to understand the “why” something happened/works/evolved because with today’s innovation the “what” and the “how” are changing, but the “why,” which is rooted in basic human psychology and patterns, tends to stay the same.

-Take psychology and human behavior classes. In the end, learning what makes people tick is the most important technical knowledge.

-Intern as often as you can in many different companies and fields to find out what you are made of and what the work actually entails. Take entry level jobs and make yourself indispensable. Everyone has to start somewhere, and it’s usually not at the top.

-Make friends with the nicest, smartest, brightest and funniest people in your school, office or social circle. These people will inspire you and push you forward for the rest of your life. Having friends that achieve in life makes you achieve as well. Don’t be intimidated by extraordinary people. Befriend them and become one.

-Be nice to everyone on your way up, you will see them on your way down, and sideways and back again. It’s inevitable.

-Do what you love and push yourself to be the best you can be.

-If you have an idea of something you would like to do, do it. You certainly will never achieve your goal if you don’t do it. It’s basic but key.

-Set big goals and work hard that way you will definitely land in a better place than when you started. Believe in yourself, stay positive and read and practice “Creative Visualization."

-Be yourself and create a business that is as unique as you are. If you do what already exists the world doesn’t need you.

-Don’t think you have to be good at everything. Specialize and surround yourself with people with complementary skills. That’s how you build a team.

-Remember that overnight success takes years.

-Enjoy life. This is it!

What have you learned about effectively communicating and advocating for yourself in your career?

Advocating for yourself starts with your own attitude and behavior. Actions speak louder than words - behave and follow through in a manner that reflects how you want to be seen and treated. In business learn that your relationships and communications there are not personal.

What have you learned about your own resilience as a woman throughout your professional journey?

The saying “this too shall pass,” I mostly apply to my understanding of the cycle of ups and downs in life and success but also to my perception of how difficult a task is emotionally, physically or intellectually. I have learned that you can work like crazy for spurts at a time. When delivering on a project I'II always think, I can sleep next week! I find that my motivation for getting things done right outweighs taking it easy but I am also equally aware that it’s not sustainable in long stretches. I really need to recharge, either through lots of sleep, being with friends, or disconnecting. As a woman I have learned that I can compartmentalize as well; be a mom and a business woman. I don’t have to do both at the same time, just do them each well when I am doing them. And I am very comfortable with asking for help and letting my guard down. I don’t have to be seen as superhuman; I am comfortable with my own limitations and take emotional strength from my friends and family.

Ultimately, I have learned that I am basically a positive person and this helps me move forward always. I can always see the bright side, the opportunity, the challenge that leads to learning and improving, the road block that leads to another better journey.

What were the most challenging or unexpected aspects of building Net-a-Porter and now Imaginary ventures?

In both cases I didn’t have prior experience and had to learn everything from A-Z which is not easy or advisable, but this was and is a blessing as much as a hindrance. I do wish I had started Net-a-porter with encyclopedic knowledge of retail and tech and business and management so that I didn’t have to make lots of mistakes. Similarly, I wish I had 20 years of venture finance under my belt to apply to Imaginary, but in both cases I also feel that the inexperience is also an opportunity to really think about the approach and what needs to be done and stay open minded.

At Imaginary Ventures, what are some of the things you look for before investing in a business?

The concept, brand or business model has to appeal to me from the consumer perspective. Would I buy that? Tell my friends about it? Recommend it? Then the team has to be exceptional. They are the ones who have to deliver.

You have your finger on the pulse of what’s new in the fashion and tech space—what is something you’re really excited about?

I am excited by the consumer-centric approach of today’s entrepreneurs - be it in service or in product, for example making fashion in sizes for all women is so obvious but companies simply didn’t do it before. I love the men’s space! They are an underserved customer segment that is stuck in a self-fulfilling loop. The industry has categorized the men’s space as a fraction of the size of women’s but that’s also where the focus has been. We are going to see an explosion in men’s brands from shoes, to ready to wear, to beauty to wellness. And I am excited about all the opportunities in to develop strong specialist brands. In the past brands had to be all things to all people in order to grow, but today, thanks to digital brands, can do one thing really well and still have a huge business through the global reach that the internet allow.

Who is a woman in the fashion, beauty or tech space who is really inspiring you at the moment?

Lorraine Twohill and Ruth Porat at Google are two extraordinary and inspiring women who I have had the honor of spending time with. As CMO and CFO respectively, they are rock stars in every way. And at Imaginary, we have backed quite a few female led businesses including Good American, Glossier, Daily Harvest, Reformation, Clare Paints, and more. These inspiring founders generally don’t take no for an answer and are building great consumer businesses. They are the future!

Learn more about Imaginary here and follow Natalie on Instagram.