Caren Merrick of The Virginia Ready Initiative: “Build more pools of mentors who commit to women entrepreneurs”

Build more pools of mentors who commit to women entrepreneurs — this is part of the model we use at NextGen Venture Partners. Women founders need mentors from the earliest of stages to build and refine ideas, pitch to prospective investors, build boards and advisory boards, recruit and lead teams of product developers, sales, marketing. As a […]

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Build more pools of mentors who commit to women entrepreneurs — this is part of the model we use at NextGen Venture Partners. Women founders need mentors from the earliest of stages to build and refine ideas, pitch to prospective investors, build boards and advisory boards, recruit and lead teams of product developers, sales, marketing.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Caren Merrick.

Caren Merrick is the CEO of the Virginia Ready Initiative (VA Ready), a business-led public-private partnership with the mission to rapidly reskill Virginians whose employment has been disrupted for in-demand jobs in resilient industries. Merrick is a technology entrepreneur, executive, investor, and board director with over 25 years of experience in growth companies. She has served on corporate boards with combined assets of $12b and revenue of $3B, including boards of the Metropolitan Washington Airports Authority, WashingtonFirst Bankshares, and currently serves on the boards of the Gladstone Companies funds, where she serves as Chairman of the Valuations Committee and is a member of the Audit Committee.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

My parents were quite young when they married and had four children right away. They had a strong work ethic and taught us to take on a lot of responsibilities from an early age. Those two things — teaching and modeling a work ethic, and setting high expectations for us, were gifts that keep on giving. All four of their children became entrepreneurs and I believe they laid the foundation for that progression.

My mother chose not to go to college so she could be home to raise her four children and she worked as a secretary at our local high school so her schedule would align with ours. My father went to college at night on the GI bill and eventually earned his MBA. I am the first woman in my family to earn a college degree and I worked my way through college, which took courage and sacrifice and gave me a lot of insight into what I was capable of. On the day I graduated from UCLA, I realized that setting and achieving big goals, overcoming barriers, and pushing past the fears standing in my way energizes me.

Can you share the most interesting story that happened to you since you began your career?

There have been so many generous mentors and investors over the years. Yet I would have to say that the day of the initial public offering of the first company I co-founded, webMethods, was unforgettable and made history as the most successful software IPO in history at the time. We had founded the company four years earlier, had been rejected by all but one venture fund, and at our lowest point had no more than $33 left in our bank account. But we had excellent ideas, products, and people, and the support of the first venture capital firm who chose to invest and who believed in us and our vision, which is all we needed. We wanted to be successful, and it never occurred to us we would make history.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I was in a packed auditorium at a TED Talk near the Bay Area in Northern California some years ago, sitting five or six rows back from the main stage with a great view. There was a guy in a t-shirt and jeans next to me who kept hogging the arms on both sides of his chair, including the one on my right, which we shared. When I gently tried to rest my elbow on my half of the chair arm, he wouldn’t let me, and I sat there fuming at how rude he was. At the end of the session, just as I was leaving, my husband came up and asked me if I knew who had been sitting next to me, and when I said no, he told me it was Sergy Brin, co-founder of Google! I laughed as I told my husband that he had been hogging the arm of our chair the whole session, but what I learned was not to be afraid to start a conversation with a stranger, even if you find that person annoying. He may not even realize it, and if handled correctly, it could be the beginning of a good acquaintance. Plus, at the time, we had some things in common in the tech world, and now I’ll never know if we could have been friends!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’ve learned that even if you have had some success, you are always learning, growing and can benefit from the insights of others to fulfill your potential. In my early career, there were countless men and women who offered candid advice, feedback, and encouragement that helped me get to where I am now. In 2014, after several years as an angel investor, I was introduced to Loretta Penn, former president of Spherion Staffing. She had run a $2 billion business and was now coaching leaders. Loretta has become a trusted mentor, and her questions, feedback, and insights have encouraged me in the latest chapter of my career, during which I launched a mobile app business from 2014 to 2018. Even now, as I lead a public-private partnership to help people reskill for resilient, in-demand jobs and help define the future of work, her mentorship has remained invaluable. Loretta’s experiences as a black woman who has done the work in leadership have been a precious gift, as she has so much wisdom, clarity, courage, and a generosity of spirit. I actively look for ways to work with Loretta and she is currently chairman of our board at the Virginia Ready Initiative.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I listen to a lot of books on Audible and read as much as I can, and one book that has continued to inform and inspire me throughout the years is A More Beautiful Question by Warren Berger. I believe this is a must-read for any entrepreneur or leader, and actually for everyone. It highlights the power and importance of questions that are the foundation for success in relationships, companies, work, and life. Asking questions implies a kind of humility that acknowledges you don’t know everything and is one of the most underappreciated relationship skills in life. It shows regard for other people, it shows you care enough to listen and sparks our minds, imagination, and creativity to solve long-held problems. It is how the founders of every start-up I’ve created or invested in has begun their journey — by asking, what if this problem could be solved? What if we tried to solve the problem this way? How have others tried to solve the problem? What happened when they did? What worked, what didn’t?

In my current role, we invite questions and feedback and listen regularly, and we also formalize it in quarterly reviews: In this past quarter, what worked? What didn’t? Why? What would become possible for us if we … fill in the blank. At the end of each day, I ask myself: what energized me today?

I think of questions as the secret sauce to a well-rounded, successful life.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

I love this question because I am a quote geek and collect quotes about everything. So it’s really hard to pick just one, yet I do find myself thinking often of these three:

If I don’t know what to do next, or if I want to get to know someone better, connect with someone, or if I’ve been presented with a problem, I think of this simple phrase: — “Ask a question”. And it always it opens things up for better information, decisions, and relationships.

The second is from Marcus Aurelius and is especially good for managing complex, difficult situations — “The first thing is to keep an untroubled spirit, the second is to look things in the face and know them for what they are.”

And the last is from Maya Angelou — “All great achievements require time.” The work we are doing with the Virginia Ready Initiative is helping people rapidly gain new skills for resilient, family-supporting jobs with good career paths. It is a 10-month-old start-up that has already helped nearly 2,000 people gain new skills. Ms. Angelou’s words inspire our team to keep at it so we can achieve our vision of helping tens of thousands of people.

How have you used your success to make the world a better place?

When my co-founder and I started our first business together, we had many discussions to identify and articulate our aspirations for the business. One was to avoid making management mistakes that we’d experienced in previous jobs. The other was that, if successful, we wanted to use those resources to become good citizens in the community where we worked and did business. The year our company went public, we set aside 10% of our shares to form a private foundation in the company’s name. We used it as a platform to make investments in social entrepreneurs who were on the front lines helping low-income families achieve an education. We had the opportunity to invest in several dozen nonprofits, including a nonprofit that has helped over 50,000 children in the Washington, DC area, another that helped women remove themselves from domestic violence and gave them job training and employment, as well as provided education and mentoring for youth and families toward a better future.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

Confidence, role models, mentoring, and tactical knowledge. Women are often reluctant to pursue entrepreneurial roles because so many of us are conditioned from the start of life to be risk-averse. We hesitate or think we have to ask permission, instead of taking charge of trying something new or that we find interesting. Starting a business from the bottom-up means putting faith in yourself and your team that you can do this. Oftentimes risk comes with failure, but with failure comes a great deal of learning.

Women may also be hesitant to become entrepreneurs because they haven’t seen enough other women do it before. From a young age, we learn through imitation. When a young girl sees a doctor or successful businesswoman that looks like her, she thinks to herself, “Hey, I can do that too”. If we model it out for more young women, more and more people will believe that a similar career is possible for themselves too. And once they have that vision, they’ll pursue more learning opportunities that align with their goals.

Can you share with our readers what you are doing to help empower women to become founders?

I’m a venture partner in NextGen Venture Partners, which has invested in several women-led businesses like Framebridge and I’ve also served as a panelist judging business plans and pitches for Vinetta, a women-led organization focusing on women founders.

This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

Women comprise more than half of the population! Their ideas, ingenuity, energy, problem-solving ability, communication skills, and immense capacity to build and lead teams have been underrepresented since the beginning. We must continue to identify the barriers and generate solutions.

Ok super. Here is the main question of our interview. Can you please share 5 things that can be done or should be done to help empower more women to become founders? If you can, please share an example or story for each.

  1. Early education and experience in entrepreneurship — Beginning in grade school, we need to encourage girls to start, launch, run, refine, innovate ideas so it becomes part of their life experience. Do what my parents did and expect more from kids!
  2. Teach middle and high schoolers how to start and run things with a bottom line by showing them how to gather, analyze and make decisions using data.
  3. Provide more opportunities for young women to work in entrepreneurial environments
  4. Increase private funding — make it a goal to invest in women entrepreneurs, as has been done with Steve Case’s Revolution Fund.
  5. Build more pools of mentors who commit to women entrepreneurs — this is part of the model we use at NextGen Venture Partners. Women founders need mentors from the earliest of stages to build and refine ideas, pitch to prospective investors, build boards and advisory boards, recruit and lead teams of product developers, sales, marketing.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

At this moment in our country, I am motivated to find solutions and to find hope and positive, productive ways forward. I’m skeptical of those that conclude that there is no hope because I believe centuries of science, philosophy, education, business, and art prove otherwise. I’m looking for ways to articulate a better future by identifying and celebrating the many things that work well, identifying and fixing things that are wrong, and casting a vision for a better future.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Sara Blakely, founder of Spanx, and Thomas Sowell, a remarkable Stanford economist.

How can our readers further follow your work online?

My blog at (which I’m in the process of redesigning!), on LinkedIn, and at

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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