Startup Women Advisor, Nishika de Rosairo, Talks Fashion, Travel And Business

Nishika de Rosairo is an active member of this year’s Startup Women Advisory Board. As a CEO and Creative Director, she hopes to bridge the business world with the art world and make entrepreneurship more accessible for artists. She serves on the Advisory Board alongside Ling Wong, Amy Stursberg, Daymond John, Angela Benton, and Mary Grove.

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My father was a Chartered Mechanical Engineer on an expatriate assignment, so I was born in Zambia, a country that borders Zimbabwe and Angola. At the time, Zambia boasted the largest copper mines in the world, and as a result, contained a substantive expatriate community. My older sister and I grew up attending international schools governed by the British schooling system, and immersed in extra-curricular activities including ballet, tap dancing, gymnastics, piano, sewing and more. My mother, a true lover of fashion, would design and sew these beautiful, matching dresses for my sister and me. It was around the age of six that I vividly recall dreaming of becoming a fashion designer, with a label following my surname, de Rosairo. But my parents were of Sri Lankan descent and anything that was not along the lines of medicine, law, accounting or engineering was given the automatic kibosh. Later in life, I appreciated this perspective immensely.

“A part of me that was not yet fully discovered was starting to flourish. Entrepreneurialism felt very real.”

After eight years of my life spent in Zambia, my parents moved us to Sri Lanka for six years, followed by a move to New Zealand in my mid teens where I continued my high school and university education. By the time I reached my early twenties, my life was about to take a turn with an unplanned adventure. I received a scholarship to study as an exchange student in the MBA program at the University of Washington in Seattle. Even with 23 countries under my belt, the experience of studying in the US opened my mind on a whole different level. A part of me that was not yet fully discovered was starting to flourish. Entrepreneurialism felt very real. Upon completing my masters program, I returned back to New Zealand for a short period until I found myself back in Seattle on a work visa sponsored by Deloitte Consulting.

I spent nine years consulting and working for Fortune 500 and Silicon Valley companies including Deloitte Consulting, Apple, Cisco, Levi, Chevron, Salesforce and many others. The type of work and experience was phenomenal, especially because I actively played a role in uncovering the complexities of these large organizations, advising the senior leaders on their talent strategies, and transforming these companies to enable them to stay relevant and innovative in their current and new markets. It was all very fulfilling, but it still wasn’t enough for me. And through that deep desire for more, dE ROSAIRO was born. A childhood dream coupled with a strong business background was starting to become part of the fashion industry.

“This creative place became an escape for me”

Despite what seemed like a structured career, my soul frequently yearned towards things that were more intuitive and subjective. I spent most of my life sketching and having dressmakers sew what they referred to as complicated designs.  In my 20’s, I trained to become a Latin dancer, and soon after, I was performing, competing and teaching dance. At the same time, I also discovered a passion for abstract art, where I started to complete custom pieces and display my work at intimate art events. This creative place became an escape for me.  I was frequently amazed by the power of “movement” I experienced through creativity and expression.  I would spend countless hours with other creatives chatting about expression and what inspires each of us. Then my mind would sway back to the world of business that I also felt very passionately about, and I would wonder what the world would be like if we had no artists and creatives around us.

Re-imagining an iconic symbol of American culture

Ironically, dE ROSAIRO was born not because I wanted to launch a womenswear clothing brand (which was my ultimate childhood dream, which I waited 28 years to launch), but dE ROSAIRO came about because the timing was right. I reached a point in my life where I was armed with the business knowledge, resources, connections, and confidence to build my own dream. What differentiated me was “re-imagining” an iconic symbol of American culture- the hoodie,  yet for the modern woman, designed so that she is able to incorporate it into her professional and contemporary wardrobe. I started to reconstruct the fit, silhouette, and fabrics of this much-adorned symbol with a degree of finesse, and as part of a collection. This “re-imagined” hoodie has now become, and will continue to be, a symbol of brand identity for dE ROSAIRO.

“I questioned if my lack of experience in the industry would place me at a disadvantage”

During this entire time of entrepreneurial discovery, I questioned if my lack of experience in the industry would place me at a disadvantage. As I started carving roads, I soon realized quite the contrary, and just how much I was leveraging my business expertise to build and manage the dE ROSAIRO brand. I was able to lay a solid foundation, which included business processes, financial and inventory models, and supply chain methodology. I also discovered that there were far too many designers who either loved the industry so much that they were willing to run their businesses for what was almost free, based on very low and difficult margins, or they simply didn’t know how to manage the varying components of running a sourcing business, coupled with cash flow liquidity that needed to survive 18 months out. I’m still learning myself.

Startup Women Advisory Board

Now, as an Advisory Board Member for the Startup Women Initiative, designed to promote female entrepreneurship, my goal is to help Creative Entrepreneurs bridge the gap between left and right-side brain thinking. It’s important (yet sometimes difficult) to connect the creative process with business operations, where the real strength of being a Creative Entrepreneur lies. dE ROSAIRO is only eight months post industry launch, yet we’ve enjoyed strong sales and strategic partnerships simply because of the parallels we are able to draw from the business world and apply to the fashion world. We truly haven’t mastered the combination in any sense, but through a series of strategic trials and errors, our goal is that we will eventually take more steps in the right direction.

Ask yourself the right questions

I don’t think all designers require a solid understanding of business to survive in today’s world, but I do believe that having a business background is what makes a difference in a very complex and fragmented supply chain and costing model. There are many successful designers who have built multi-million dollar global brands without any sort of business background. I do believe, however, that the industry has changed, and what worked even a few years back does not necessarily work today. Consumer spending habits influenced by social media, eCommerce models, and consumer choices have shaken up the entire industry, which is why the question we have to ask ourselves today as Creative Entrepreneurs is not “how do I launch a fashion brand?” but instead “how do I launch a fashion brand with a view to longevity?” Those are two fundamentally different questions, and the answer to the latter question is where I believe success in the industry lives.

Utrip's Director of Biz Dev on Why Being An Entrepreneur Doesn't Have To Mean Being A Founder

This article is written by, Lewis Krell, a Canadian ex-pat currently stealing jobs from hard working Americans. In his spare time, Lewis enjoys planning trips on Utrip, allocating capital to its most productive use and dispensing advice despite being severely under-qualified to do so.


I believe that entrepreneurship and capitalism are two of the most positive forces on the planet. I believe that Shark Tank is one of the best shows on television. I also believe that too many bright, entrepreneurial minds are currently working in finance, accounting and consulting because they have narrowly defined views of what being an entrepreneur can be. The reality is that we can’t all be founders and CEO’s but one can be extremely entrepreneurial without being the entrepreneur.

After working for five years at an established, traditional Investment Consulting firm, I decided to pack my bags and join a promising travel technology start-up, Utrip, as the Director of Business Development. Despite my affinity for entrepreneurship, I didn’t leave my corporate confines to start up my own venture, but rather, I left to work directly under the guy who left his own corporate prison to start a successful company. I think of myself as a modern day ‘Hand of the King’.

There is no industry that suffers more from survivorship bias then entrepreneurship and it shows due to the plethora of articles about quitting your job to become an entrepreneur. If you are lucky enough to write an article giving advice about why you should start your own company that means one of two things:

• Your journey has just begun so success nor failure has happened yet

• Things have gone, at the very least, moderately well for you

You seldom see the article about people who tried and failed to make it on their own and then went back to their old careers. Failed entrepreneurs are much more common than successful ones and you can be sure that they are much less likely to write advice columns. I mention this because I find that the connective tissue of all stories about cubicle jockeys working for a big company daydreaming of making it on their own is exactly that – they go out on their own.

This can be a dangerous thought. Not everyone is meant to be a CEO and even if you are meant to be a CEO and start your own business, maybe the time isn’t right for you right now. Too many people get discouraged from leaving their traditional jobs because they think the path you have to take is to go ahead alone, or at most, with a cofounder, and start your own venture. Too many people equate entrepreneurship with being the founder of a new company.

Many would-be entrepreneurs stay in their comfy 9-5’s because they don’t think they have found the idea yet. The billion dollar idea that will lead you to a life of yacht parties and space exploration if you’re a fun person, or bequeathing millions to your pets and having your mistress record your horribly racist opinions if you are a terrible person. However, as the morbid expression goes:

There are many ways to skin a cat and there are also many ways to be entrepreneurial.

So what’s it like going from Finance to the Startup world? It’s not for everyone but for me it is a great fit. I find it liberating and not only because I really enjoy not shaving. To work for a company that you truly are passionate about, and where your success is perfectly aligned with the company’s success, more than makes up for the fact that I’m pretty sure our office furniture was purchased at a prison auction. Although it’s great having no websites blocked at work and I certainly am saving money on dry-cleaning bills, the thing I enjoy the most is that my impact on the company is tangible.

Every phone call I make can lead to something good for the company as opposed to my old firm where I was just another handsome, young cog in a well-oiled machine. A cog that worked to make the older, richer cogs in the machine… even richer. Please note that this arrangement doesn’t bother me. Those old, rich cogs worked hard to build the machine I was lucky enough to work in but I didn’t want to wait 15 years to become one of them. I knew the moment I handed in my resignation letter that the wheels were already turning to replace me. In a short period of time things would be running along smoothly again, just as they had before I got there, and just as they will long after I’m gone.

‘They say our generation has no patience and no loyalty but what we really have is no defined benefit plans’

They say – if you don’t want your boss’s job then you are in the wrong job. Although I wouldn’t have minded my boss’ paycheck or his ability to delegate work, I never once wanted his job. I knew I didn’t want to get too comfortable where I was and forsake my entrepreneurial inclination. Luckily, I had a great work/life balance so I was able to spend time exploring some of my ideas further. I filed for patents and I had prototypes built, but I never actually made the leap to fully commit myself to any of these endeavors.

The opportunity to work for Utrip presented itself mainly because some of the ideas and thoughts I had while working meshed with what the company was creating. I was able to pitch ideas to the CEO I never would have had if I tried to start my own venture years before. By being patient and realistic I was able to find a great opportunity to see some of my ideas come to life, and to finally take the plunge to become an entrepreneur.

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It’s important to note that I have no illusions about my role in the company. I get to work on and help with some of the most exciting parts of being an entrepreneur like fundraising, product discussions, strategy discussions, hiring and of course, selling. Having said that, my sweat and tears (and minimal blood) that will go into this business – if it’s successful as we hope – will never be on the same level as Utrip’s CEO, Gilad Berenstein. Gilad started Utrip at age 23 and as much as I thought I would make a kick-ass CEO at age 23, the reality is that I was probably not mature, motivated or sober enough to be running a company where people’s livelihoods depended on me.

Not jumping half-heartedly into trying to start my own venture, as I almost did, was one of the best decisions of my life. Every day I come to work and find creative solutions to solving problems as I attempt to turn our wonderful product, Utrip, into a market-leading business. My life is very entrepreneurial, but I am not the entrepreneur. And I couldn’t be happier with the arrangement.