Women + Risk: A Conversation with Entrepreneur and Author Deborah Perry Piscione

BettyConfidential is thrilled to introduce a new series that shares stories of risk among some of the industries most successful women around, starting with our own CEO, Deborah Perry Piscione.
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Men are said to be great risk-takers as a whole, but it’s our belief that women tend to do more extreme risk-taking. BettyConfidential is thrilled to introduce a new series that shares stories of risk among some of the industries most successful women around. It’s about taking risks and getting what you want. Learn from the experts how to take big risks and achieve even bigger rewards.
Deborah Perry Piscione
BettyConfidential’s CEO Deborah Perry Piscione is a seasoned Silicon Valley entrepreneur; a national bestselling author of Secrets of Silicon Valley: What Everyone Else Can Learn from the Innovation Capital of the World; and the founder to Alley to the Valley, an organization that networks the most influential women for deal-making, and co-founder of Chump Genius, an educational gaming company for kids. She’ll be helming this series going forward, but to start, we want to share Deborah’s own experience and thoughts on risk, as it’s these experiences that inspired the idea of taking a closer look at women and risk. Here’s the conversation we had with Deborah, which will serve as the foundation our future conversations with other fearless women:

Betty: What is your definition of risk?

Deborah Perry Piscione: Taking yourself out of your comfort zone, putting yourself on a fundamentally different path, and living a life of extraordinary rather than ordinary.

Betty: In your professional career, can you tell us a time when you had to take a big risk? What was the outcome and if the chance, would you do anything differently?

Deborah Perry Piscione:  I had a thriving career in Washington, DC, having worked in national politics and media, and then one day my husband came home and said, “I got a job opportunity and we’re moving to somewhere in California.” I had to completely re-invent myself and figure out how I take my DC career path and transcend it into Silicon Valley.  I remember being on my bike a few months after we moved, still unclear on what I was going to do, and just wondering when I was going to have the answers. It was such a scary time, but when I look back, there was something incredibly romantic about it. I was learning to live without the direct path and with a degree of chaos.

I really had to jettison my previous 18 years of experience and I opted to become an entrepreneur, and learned that I was pretty damn good at it. Entrepreneurship allows you maximize the best of the left and right side of your brain. While on the surface it does appear that running a company is about being great operationally or have a deft of knowledge about technology, but in fact, it is highly creative, as you have to constantly be tweaking your vision, putting the right team together, and constantly motivating people – it emits incredible energy and I’ve been amazed by the level of people and companies that have identified with the brand of BettyConfidential or Alley to the Valley.

Betty: Do you think that women are encouraged to be risk-takers, as much as men are?

Deborah Perry Piscione: I don’t…I believe that women are raised to play it safe, because girls learn how to be communicators at a very young age so they learn how to talk everything out. Yet, many of the women I meet in Silicon Valley are a breed onto themselves, and have been extraordinary risk-takers. They have postponed or sacrificed various elements of their life for their educational and career advancement, for the greater good, etc. One of the companies I advise, Homemade, is comprised of two female co-founders from Stanford University who have more degrees between them (MD, JD, MBA, Fulbright Scholars, etc) then a collection of a dozen people.

Regardless of the postponement or sacrifice, for most everyone, it seems to have worked out.

Betty: What are the consequences of risk in your industry?

Deborah Perry Piscione: We are living in a period of exponential times, so it is difficult to survive if you are not incredibly nimble and able to move on a dime.

Betty: What’s something you know now that you wish you knew 10 years ago?

Deborah Perry Piscione: That your education will dictate a majority of your path in life, and while there are exceptions to every rule, you have to work that much harder to prove your value.  My parents didn’t realize the value of education and truly raised me to be married rather than recognize my gifts and interests in math and science.  I was only given one option for school throughout my K-12 and undergraduate experience, and don’t remember ever being asked, “What do you want to do when you grow up?”  Once I was able to be independent is when I realized my love for learning and put myself in an education environment for graduate school where I could thrive and beinspired – thank you Georgetown University.

Betty: Who are some of your role models / heroes?

Deborah Perry Piscione: I am attracted to those bold risk-takers in flight and space (such as Amelia Earhart and the Apollo astronauts); people who have made a difference in civil and human rights (such as Lucretia Mott and Elizabeth Cady Stanton, Martin Luther King and Mandela Nelson); and just people who have just gone places where they have not been before (such as Jackie Robinson, Danica Patrick and Diana Nyad, of course).

Betty: Are there influences in your life that encourage you to take more risk, such as age, money, a competitive spirit?

Deborah Perry Piscione: Well, obviously, the more money you have, the more risk you can take.

My mother took a personal risk after 41 years of marriage. She left my father and later met the love of her life. She and my stepdad now live a life that everyone should live in their later years – they travel constantly, have adopted each other’s hobbies, and just adore being around one another.  I admire my mother for that (although she claims she got the courage to leave my dad from me).

Betty: What thought-process occurs when you decide the level of risk to take?

Deborah Perry Piscione: Perhaps none, which is where that fearless gene kicks in.  If it feels right, I just go for it.

Betty: Do you believe that risk-taking is critical in order to achieve success?

Deborah Perry Piscione: 100%. Without risk-taking, you are not doing anything and wasting life away.

Betty: Do you tend to be more risk averse in your personal life vs. your professional life?

Deborah Perry Piscione: I didn’t get married until my mid-thirties so I was able to take a lot of personal and professional risk, but once I had children, I grounded myself slightly more. I still travel with my kids internationally, but perhaps, I am not on the fringe of extreme sports or running through the streets of Cairo (like I once did) with three young children in tow.

Betty: Does having a family make you more cautious when it comes to risk-taking?

Deborah Perry Piscione: It depends … In some respects, I have become more of a risk-taker professionally, and introduce smart risk-taking to my children.

Betty: Do you think anyone would ask a man that question?

Deborah Perry Piscione: Yes.  I think most people, men and women as a whole, become more risk adverse once they have that mortgage and children to take care of.

Betty: What’s the best advice you’ve ever received?

Deborah Perry Piscione: Brad Raymond, Soledad O’Brien’s husband, once said to me, “Business is not personal … remember that.” It has always stuck with me.

Betty: What advice would you give to others about risk-taking?

Deborah Perry Piscione: You only have one life to live – what do you want it to be…ordinary or extraordinary?


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