Former Polyvore CEO Launches Joyus, Raises $7.9M Series A

sukhinder.jpg

By Sukhinder Singh Cassidy (Founder & Chairman, Joyus) Eleven years after founding my first company, I've discovered that embracing my inner entrepreneur again is more difficult than I had imagined it would be. This whole experience leading up to the soft launch of Joyus has made me think a lot about why women don't start companies at the rate men do -- and why, despite the trend, here I am on my second startup.

One thing I know for sure: It helps if entrepreneurialism is in the blood. My parents, both doctors, ran a medical practice for over 30 years. My father loved running a small business. From the age of 11, I was doing his taxes. I was taught to work for myself. And it's stayed with me. My experience supports the data out there that entrepreneurship runs in the family and is fostered in families.

That said, there are a few other things I've learned about entrepreneurial success since I've been on my own and in the game:

Face up to ego risk.

When I started my first company, Yodlee, at 29, the risk facing me was in material/financial terms. Today the biggest risk -- the thing that could have inhibited me from starting a company -- is ego risk. That's much more intangible that financial risk, but it's powerful emotionally. I think to myself, what if I fail? What if I don't figure it out? Will others judge me for choosing this path over the expected "executive" role? While I know male identities are also tied up in their work, I wonder if women take failure and all its implications more personally.

If not now, when?

When I left Google in 2009, I wanted get back to my passion for building companies and find my higher purpose and impact. I left three months pregnant with my third child. Today, with two of my three children age five and under, I sometimes think that maybe there's a better time to be taking this kind of endeavor. But as we grow older and time grows scarce, I am seeking my highest potential, and there's no better time than now to find it.

Embrace your grand vision.

Giving myself permission to be visionary has been harder than giving it to others. I'm not sure why, because for many years, vision and energy have been essential parts of my leadership style in scaling large teams. Perhaps it's because in the world of technology, you're either labeled an "executive/operator" or a "product visionary." As if it's impossible to be both. But there's little upside to not embracing your grand vision for your company. As Reid Hoffman, the founder of LinkedIn (LNKD) and an investor in some of today's hottest startups, says, it takes as much energy to think big as it does to think small, so why think small?

Know that you're a slave and master too.

As an executive or an entrepreneur of great ambition, you are deeply tied to your work--and all the more so when you're the one keeping the lights on. All the women on my management team want to win--badly--and work incredible hours day and night. For women who occupy dual titles of CEO and CHO (chief household officer), the entrepreneurial life is daunting. In our family, Simon, my husband, runs his own money management firm and is pretty involved--and we have an amazing nanny. But with children who are 11, five and one, it still takes all our effort to juggle schedules. Not that building my own company will be easy in any way, but I can be the master of my calendar. Having the choice to not commute cross-country (or across countries) is meaningful. So is being able to spend two hours with my children before they go to bed and answer emails and phone calls afterwards.

Permit yourself to be irrational.

In some ways, there is no rationality in being an entrepreneur. You are trading direct and perhaps major impact in a job you currently do for potential greater impact, but the statistical probability is that you will fail. I love data and have been trained in data-driven cultures all my life. But by choosing to start a company again, I've had to come to peace with allowing both sides of my brain -- the creative and the analytical--to participate in the process. And after two decades inside entrepreneurial companies, here is the most valuable lesson I've learned in deciding whether or not to take the plunge: The greatest risk lies in not giving yourself the full chance to make it.

This post was originally posted at Ex-Google exec Singh Cassidy on Joyus and facing her "inner entrepreneur".

Editor's note: Got a question for our guest blogger? Leave a message in the comments below. About the guest blogger: Sukhinder Cassidy Singh is Founder & Chairman of Joyus, the web's first video commerce experience, launched July 2011. Prior to Joyus, Sukhinder was CEO at Polyvore. Previously, she was President, APAC and Latam at Google, which she scaled to a multi-billion dollar business over 5+ years, and Founder and SVP of Business Development at Yodlee, a leading online financial software company. Sukhinder is a current advisor to Twitter, on the board of Women's Nation, and a former board member of J.Crew. Follow her on Twitter at @sukhindersingh.