Trailblazing Women: Dolly Singh, Founder & CEO of Thesis Couture

This interview is part of a series on Trailblazing Women role models (Entrepreneurs and Leaders) from around the world and first appeared on Global Invest Her. You have to see what you can be.

Dolly Singh, Founder & CEO, Thesis Couture
Dolly Singh, Founder & CEO, Thesis Couture
“Women, this is our time. We can finally change the world in very fundamental ways, in the next 20 years, at least in the developed world. Of all the generations of women before us, we get to be alive at the time when this changes. This is the time women can make the most impact we have ever had the capacity to make. Seize the day.”

Dolly Singh is the Founder and CEO of Thesis Couture; a fashion-tech company bringing together a remarkable team of technologists and experts from fashion, architecture, medicine and engineering to reinvent the iconic stiletto.

Dolly was formerly the Head of Talent at Oculus VR, a disruptive gaming and virtual reality technology company which was recently acquired by Facebook for $2B+. She worked directly with the company founders to help build a best in class team and talent practices to support the business in preparation for the launch of the revolutionary digital platform, the Oculus Rift.

Previously she was the Head of Talent Acquisition at SpaceX, where she was responsible for talent across all engineering (software, hardware, electronics, propulsion, structures, launch and test), operations, and business teams; and worked closely with the company CEO, Elon Musk, to grow the company from ~200 to almost 4000 in 5 years.

Prior to SpaceX, she was the owner and managing principal at a boutique consulting firm with Fortune 100 clients in the aerospace, defense, and biotechnology sectors. Her experience spans all aspects of human capital with an affinity for disruptive entrepreneurship models.

She is graduate of the University of California, Los Angeles, and currently resides in southern California with her husband and their four children.

Visit her website and follow her on Twitter @dollysingh @thesiscouture

If you would like to support Global Invest Her’s work in helping women entrepreneurs learn about funding, use the code #InvestHer when you purchase your first pair of the amazing Thesis Couture shoes here. Thank you!

Who is your role model as an entrepreneur? 

I think that’s an obvious one! I spent 6 years working for the world’s most remarkable entrepreneur, Elon Musk. If anyone wants to emulate someone who is good at making positive change in the world and making really big businesses while doing it, he’s the man. What inspires me most about him is the ability to speak into existence what you can see. He is as demi-God-like as any human being can be and is very good at what he does. Who else could change the automotive, aerospace and solar industries as a whole, look to change the terrestrial transport industry and now want to be the guy that makes sure AI is safe for humanity – who else can do that? I think he’s the greatest entrepreneur in the history of time.

What is your greatest achievement to date? 

From a life and personal standpoint, my 4 wonderful children and my wonderful husband are what I’m most proud of. Family is the thing I place the most importance on. From a business point of view, I am ambitious. Nothing I’ve done yet is what I want to be my crowning achievement. Through a combination of good fortune and making the right decisions, I have been able to work for 2 of the world’s most successful, billion dollar startups - Space X and Oculus VR and both changed the landscape of the industry they were in. They created an avenue that other people are now competing in, because they made it viable. Both were remarkable learning opportunities. To be able to learn from all the people around me who were significantly smarter than I was, has been fantastic.

Graduating from college was a big thing for me. I was the first person in my family to get a grant and pay my way through college. At the time that felt like the greatest achievement I could have done and I still hold on to that feeling. I think I’ve done some good things so far and am hoping to do even better things!

What has been your biggest challenge as a woman entrepreneur?

I’ve always been the girl that says, yes you have to work harder, but it makes you better. So I’ll take a system that works against me, because in the end I’m going to be smarter than you are. When it comes to raising money, there are so many people that fit into a specific demographic. If you’re not a white male between the ages of 23 and 38, it’s harder to get the money. You have to dance more and jump through more hoops. There are lots of non revenue-generating companies that raised millions of dollars and for us, raising $2 million has been a lot of work. I think we have to work much harder, not just women, but also minorities and anyone who doesn’t fit the specific, perceived, case study of ‘we know this worked, so let’s keep investing in that’.

I understand the bias. When you are an investor, you invest in things you understand, because by being able to add value, you reduce the risk on your money. You know you can make the idea better. When the ecosystem is very rich with people who have done things one way, they tend to look for people similar to themselves, because they know how to help them.

It takes time and individual people being willing to say they will work twice as hard. Now is a very unique time in history for women. It’s the first time that women control more than 50% of the wealth in the U.S., and that women are outpacing men in college and universities in every developed country on the planet. I think this is the generation of women that will finally be able to see a shift from patriarchy to a true partnership. We’ve fought long and hard and I think it’s going to pay off.

What in your opinion is the key to your company’s success? 

Based on the models I’ve seen, and I’ve been lucky enough to see good case studies – team is the only thing that matters. A soup is only as good as its ingredients! We have to do the same due diligence that I took to businesses where we were building much more complex products (VR headsets or rockets) and take that same robustness in the team, to shoes. So that you have that same multi-disciplinary thinking, a certain level of brilliance and high cognition in the room. Having super smart people work on a problem, is a good way to solve a problem. With rockets and VR it’s very easy to get super-technical people excited – with shoes, I wondered how I was going to do that. When you think about it like a body-centric engineering problem, they’re interested. Building the world’s tiniest bridge/stable prosthetic is what is basically involved. We had to speak to the engineers in their language. The asset that makes us important and significant, is our team.

My experience and the fact I’ve been part of the process of building amazing teams before, helps me think about the problem that most people in this $40 billion/ year industry haven’t done yet. In this entire ecosystem, there is no engineering and R&D entity – that’s ridiculous and doesn’t make sense! When you are making something worth $40 billion a year, you don’t think anything is broken! Fashion has an antiquated and archaic way of doing things and now it’s being hit on all sides by technology. I honor the things that are precious from the past, like the leather and the artisan’s capability with the stitching. Everything in the upper part of the shoe is precious, because that’s what makes the shoe sexy. At one of the factories we work with, the artisan that worked with Christian Dior and Roger Vivier to invent the first stilettos, was his father. He is now helping us with this next generation shoe. The former did something remarkable for their day, it’s just that since the days of Ferragamo, we haven’t really seen somebody in footwear who’s really an architect. I know how to build engineering and innovation team and that’s what I’m bringing to shake up this industry. The fashion industry is basically made up of design houses and factories that make the product. There is no R&D in the supply chain. Having R&D and innovation as part of the product design team, and thinking of the product holistically, inside to out, you get a very different set of solutions, when you think about the problem that way. The shank that holds up a stiletto is not very structurally sound. I want to build a business that is a fully vertically integrated business, like Nike (controlling all aspects of the process) but in the fashion space.

If you could do 1 thing differently, what would it be?

That’s a hard question, here’s why. I screw things up all the time, so there are plenty of things I should do differently. I just have a philosophy that I never screw the same thing up twice! I think I would probably go to Italy sooner, and am not even sure about that. I intentionally blinded myself about not knowing too much about the footwear industry and how they do it now, because I didn’t want that to constrain us. I wanted to start with a clean sheet of paper and figure out, how do we make an amazing stiletto, and what’s the most structurally sound way to do that, while managing all the outside lines. Keeping a sexy silhouette is essential in a shoe – one tenth of a millimetre left or right, will take that thing from sexy to either slutty or start to look orthopedic. Each one of those millimetres matters. When we eventually did get to Italy, it took around 8 months to get the assembly line the way we wanted it. I do wonder would it have been smarter to go there sooner, or I could also say that then we might not have come up with the solution, because we would have said that’s too hard. Maybe I would have done that differently but am not sure.

The other thing I would change, is when I first started raising money, I was too focused on hearing what I wanted to hear, and that came back to bite me. I think I could have done a few things smarter, earlier on in the fundraising process that would have saved me some heartache and time. Now I know better.

What would you say to others to encourage them to become entrepreneurs?

Stock your liquor cabinet! (laughing). There’s a freedom to doing what you love, and on the other side of the coin, there’s also a greater emotional attachment, which can be both good and bad. Women in particular should be entrepreneurs, because if we don’t step up, the system doesn’t change. Take one for the team, even if you’re scared! Go do it, whatever it is. Understand that women are now the most powerful customer in the world. As a women, you understand them. You can help serve that customer in a way that men never can. There are thousands of businesses worth billions of dollars that you could go out and be engaged with! Go do something that feels important to you, where you can get up every morning and have fun. Who wouldn’t want to do that?

On the flip side, entrepreneurship is not for the faint hearted. It’s super stressful, it puts you to the test. You hear entrepreneurs say this and you don’t ever get it, until you’ve been there yourself. Elon Musk had a quote a long time ago, about ‘chewing glass and staring into the abyss’. That’s how it felt when both of his companies were about to die. There’s an intense need to really be committed. I also think that optimism and not knowing how hard it is, is the best thing. If I had known how hard it is, three years ago, I may have accepted one of those nice corporate opportunities! You have to really think about it and really want it. If you do, it’s certainly more exhilarating that building somebody else’s dream. Your ignorance is your greatest gift. The fact that I knew nothing about shoes, was why I could think about making shoes in a different way. You could look at not knowing something as a deficit or an advantage – it’s all a matter of perspective.

How would you describe your leadership style?

I’d like to believe that I build an honest and open relationship with each of my team members, where you can say the things that sometimes go unsaid in corporate businesses. What I hated about corporate businesses, was the politics. Our office is a house, and it’s part of a philosophy. At a start-up you are like a family, and having that family approach has worked well for me so far. I’ll be very candid in saying that I have very high expectations, I’m super demanding and am not an easy person to work for. If you want an easy job, there are lots of other people to work for. I try to be very honest and supportive and want to hire people where our lives will be intertwined – not just working together, we are part of a unit working on something important together. We are a team. I grew up playing basketball and the team is very important to me. At the end of the day, everyone understands what their parameters are. It’s enough to have some order and respect for each other. To some extent, even though I’m demanding and expect a lot from everyone on my team, I expect them to hold me to the same standards. I’m very assertive and I like to hire people who are also assertive, so nobody is licking their wounds in a corner, rather we are all challenging each other to be better.

What advice would you give to your younger self?

Hindsight, when you look back, is always 20/20. I try not to look back at what I would have done differently, because the journey got me here. The things that are most important to me from a family point of view, I already have, so I’m winning before I even leave the house. I wouldn’t want to change where I am today in any way. I would definitely work harder sooner. In my 20’s I worked hard and had fun, graduated with honours. Yet I wasn’t thinking about getting the most high-powered internships at the time. I don’t know that I’d change my journey that much, other to tell myself the things that would encourage me in the times when I was in the valleys. I would tell my younger self that there are peaks and valleys in life, and that when the valleys come, the peaks are never far behind. There should be an alcoholics anonymous for entrepreneurs, an Entrepreneurs Anonymous where you feel supported when you feel like jumping off that metaphorical cliff and someone tells you it’s going to be ok. Because entrepreneurship takes so much out of you, you have to remember that, it is still a tier two problem.

What would you like to achieve in the next 5 years? 

I’d like to build a billion dollar company! Let’s see what the universe has in store. The universe is with you if you’re hustling. You definitely have to be in the right place at the right time sometimes too.

3 key words to describe yourself?

  • Ambitious
  • Caring
  • Driven

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