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

sukhinder

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.

  • http://Foodily Andrea Cutright

    Congratulations on doing it again. Very inspiring.

  • http://www.sophiaperl.com Sophia

    It sounds like you’re a busy person. Congratulations on the recent round of funding. I have some questions. How do go about seeking new opportunities when you have little time in the day? How do you know if an idea will be the next multi-million dollar idea? What questions do you ask to vet out new ideas? What one mistake have you made that you learned the most from? Do you have mostly men and/or women mentors and why? Thanks!

  • SS

    When you were 29 and launching your first company, did you have a child, and if so, how did you manage the work-life jugglery?

    You mentioned that the risk you faced back then was material/financial, so I imagine a terrific nanny was not easy to afford. I am interested in hearing how you pulled it off financially if you did have a nanny, and logistically if you didn’t have one. Thanks!

  • http://heyneighbor.com Barbara Pantuso

    Love this line: “there is no rationality in being an entrepreneur.” and your advice to do it anyway! I did and I agree with both statements.

    Thanks for sharing!

  • http://www.joyus.com Sukhinder Singh Cassidy

    Thanks for all the comments. A few responses:

    SS-when I was 29 you are right – I had no children, no husband, no nanny so my time was completely my own. I was able to take financial risk then because I had a lower expense base, had saved some money in my first 6 years of work that I was willing to whittle away by taking a lower salary, and we raised money quickly. If you are a mother at this age, you have a bigger expense base but I think the key is to recognize that its basically going to be work and your child and not a lot of time or money for anything else for a few years (but hopefully worth the sacrifice on both counts). If you can raise some VC funds early that will help pay yourself a small salary. If not you may need to incubate on the side and you will sacrifice a ton of sleep trying to do your day job, see your child and then work at night on your startup. You also need a darn supportive husband and/or family with whom you negotiate some help. Not easy certainly but good luck.

  • http://www.joyus.com Sukhinder Singh Cassidy

    Sophia – thanks for the great questions. I will be doing another blog post in the coming weeks on how I decided this idea was the One and vetted the ideas so as to be more helpful.

    In terms of mistakes I’ve learned from the most:
    dont compromise on the people you hire. Everyone says it but its so true. My business mistakes I’ve never regretted as much as mistakes in people decisions, for eg either hiring the wrong person for the job despite misgivings, or not dealing quickly enough with a situation that’s not working out. You do a disservice to that person, yourself as a leader and also the rest of your team who gets frustrated when the situation isnt acted upon/resolved/improved.

    Most of my mentors have been men; my father and several people I’ve worked for deeply who each taught me a skill/perspective I didn’t have. They also gave me a chance to grow/run with something despite my lack of experience in that area while being able to go to them for guidance. I believe that often your greatest mentors are people you work with closely that you can learn something from and who in turn know your strengths/weaknesses and your quality of work deeply.

  • http://www.Fashion-Ade.com Ella Dyer

    Dear Ms. Cassidy,

    As a big fan of both you and entrepreneurial efforts, I’m thrilled to see you back in the game via Joyus.

    We’ll have to compare notes sometime as we have a mutual friend and also an e-commerce experience (found at http://www.Fashion-Ade.com).

    Best,
    Ella