Deborah Jackson | Founder & CEO of Plum Alley

For the last several years, Deborah has been prominent in the New York start-up community. She founded her company Plum Alley in 2012 to increase the economic strength of female founded companies and to provide greater access to capital. She co-founded the Women Innovate Mobile Accelerator for women building new mobile first technology. She has made several early stage investments in technology, mobile and health related, and is a Limited Partner of the Golden Seeds Fund 2. Her expertise comes from a two decade long career raising capital for companies, governments and other issuers in both the public and private markets starting at Goldman Sachs in 1980.
 
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My Future Dreams And Ambitions | My long term goal is for Plum Alley to be the destination site where women entrepreneurs and creators can access funding and supporters. When women have the chance and the tools to build products and companies, they do so with a desire to tackle the biggest social problems and make a difference in the world. They create complex and meaningful products that matter. I can only imagine what the world would look like if lots of women built things and started companies.

How I Use My Mind | If you train your mind to see the world as a place that you can change, you will see opportunities everywhere around you. Plum Alley arose from a need I saw in the market for women to raise money, and my belief that most women have a deep and real desire to make the world better when they found companies.
I am determined to find a way in my company to encourage and foster more women to dream and build. With the power of the internet, new things are possible for women and women will make opportunities happen. Even with small amounts of capital, big things can be done.


I Am Driven By | I work just as hard now as I did as an investment banker but I do it because I am blessed to be able to have a company and make a difference. What I build is my own and there is so much freedom, confidence and satisfaction that comes with that.
After a first career in a male dominated industry, I could not be happier thinking about innovation, technology and the future and women conquering it all. I believe that women and their talent are under-utilized in the world. I saw it on Wall Street.  I see it in academia, in media, in government–everywhere. We need women to be in more leadership positions because they have different skills, values, interests and perspectives to bring to the table. If women hold positions of power in all sectors, I truly believe the world will be a better place.


I Am Inspired By | I never really had one. I mostly saw examples of women in situations and thought, ‘I don’t want to be there, I don’t want to emulate that.’ One example is growing up in a family of five children, where my mother chose to be a homemaker.  My grandmother was a successful business owner but my mother chose not to work outside of the home.  Seeing my mom endlessly cooking, cleaning and folding laundry made me think I wanted to earn my own money and hire help for those chores.  I knew growing up I wanted to have a profession and career. I hope this generation has more women role models and I hope to be one for my own daughters and for other women.  I want to show women that you can continue to evolve over your whole life and learn and grow at any age.


Deborah-Jackson_P1The Characteristics Of Success | Embracing disruption. I have disrupted myself many times again by changing my physical location and also my career path. After college, I moved to Boston because I wanted to move to an urban area. I had one friend and about $50 to my name. I found a job at a Chinese restaurant and lived with my friend. Moving somewhere new forces you to grow and adapt rapidly. You have to start over, make new friends, learn a new city, find your way. You have a clean slate. My first jobs out of college were in government and I wanted to do something else. Another disruption was changing my career and life direction by moving to New York City and going to Columbia Business School. I switched careers again when I became an entrepreneur after 20 years as an investment banker. In this era, people must evolve to keep abreast of the changing times and they need to embrace disruption because it will happen anyway.


My Highlights | There are three distinct memories that come to mind. The first is leaving Goldman Sachs after a decade with a group of colleagues to start a boutique firm. It took two years and lots of soul searching and evaluation to leave an established and secure position to found a firm.
The second was when my company sponsored the first all-women hackathon. It was a transformational experience for me. Eighteen women voluntarily gave up a weekend to build something new. What was conceptualized and built over 48 hours was a fully functional, interactive game to prevent sex trafficking.  Not one of the women had any real knowledge about sex trafficking before that weekend, yet they researched the topic, conceptualized a product, and delegated tasks to create something important and innovative. What these women built–a decision tree based interactive game that can be played 1 billion different ways, was nothing short of brilliant.
Last but not least of course, is founding Plum Alley, and I am continuing to build out my dream.


Advice On Building Wealth | Work hard, have good values and principles, and care about what you do.


Lessons I Have Learnt | Invest in yourself.  Women tend to take care of others and put themselves last.  This is not healthy or good for the world.  There are things you can do to invest in yourself.  Take a class to learn something new.  Join a book club. Exercise to keep your mind and body nimble.
Take risks with your money if you could afford it. Not crazy outsized ones, but I believe you should invest in the change that you want to see in this world.


Deborah-Jackson_P3On Inspiring Others | The way to gain influence and find others who believe in you and your mission is to communicate and share your ideas and wisdom. No one can sign on if you don’t put out your beliefs and reasons. Then you must be true to what you believe in. You must be an example and live a way that is consistent with what you believe in.
I also believe that there are 3 crucial elements that anyone should provide to their team members: authority, autonomy, and mobility. I have found that this allows individuals to be satisfied and challenged.


A Key Talent | Specifically as an entrepreneur, what I have learned over the years is that if you find what matters to you most, you will discover huge energy to live with purpose and to move forward with what you believe in. Others will be drawn to your energy and your wisdom and you will then have a chance to do more for your company.


Dealing With Doubt | Optimism and passion. Founding a company for me was as much of a calling as a business choice. Being an entrepreneur is not glamorous, and it is not for people who like to work with structure
and predictability. It is very risky and very hard. I have times when I wake up at night wrestling with a decision: “Why didn’t that work? Should we change course? Should we ramp up or slow down? Maybe not that many people care about this. Maybe the model is wrong.”
But to pursue my mission, I had to move forward and be an example of a female founder. I realized that having my own company and working in the trenches of the technology start-up ecosystem in New York City would increase my impact. I wanted to innovate and to contribute by being a role model and inspiration. And most of all, I was optimistic about what women could achieve in their own companies, away from traditional
corporate America. My passion and mission became clear– to see more women create new companies and products and to build their own wealth because with wealth, women have a greater ability to influence the world and create lasting change for the better.