SEATTLE, WA – This interview is part leadership playbook, part global memoir. Karen Cone shares sharp, unfiltered advice for women founders from the pitch mistake that costs them investor confidence, to why learning to delegate is key to scaling. Along the way, she reflects on growing up between Cold War capitals, helping IBM and Microsoft expand globally, and why she’s now channeling that experience into backing underestimated innovators at Mastersfund.

Nhã Vuong: I am delighted to introduce you, Karen Topping Cone, to the Mastersfund community. Tell us a bit about growing up as one of Audrey and Seymour Topping’s daughters and how that affected your early career. 

Karen Cone: I was what is often called a third-culture kid.  This is a child of ex-pat’s who was raised abroad.  My Dad, Seymour Topping, was a US citizen, foreign correspondent and editor, who spent most of his career with The New York Times.  I am one of five daughters born in four different countries.   I was born in London and traveled to many countries.  Our primary posts included Berlin, Germany, just before the Wall went up, Moscow during the Soviet era and Hong Kong when my father covered the American Vietnam War and other major events in Southeast Asia. 

Meanwhile, my mother was an amazing photojournalist who covered major global events.  Her photographs of Soviet Premier Khrushchev were published on the cover of The New York Times immediately after the Cuban Missile Crisis.  Her photographs and stories on China and Chinese leadership were on publications that included National Geographic, Time, Newsweek and Life.  Both my parents are authors and have published multiple books.  We moved to the US when I was in high school after my father was promoted to editorial roles at The New York Times. 

All this had a major impact on me.  I learned to respect and work with many different cultures and appreciate many world views without judgement.  My mother taught me that it is possible to have a career while raising five children and supporting her husband – she was and, fortunately still is my superpower.  Due to my years living in the Soviet Union I learned to speak Russian. In college I majored in Sino-Soviet Studies.  Everyone thought it was a ridiculous major and I would never get a job.  However, at the time I was graduating from college global trade opportunities were opening.  I was impressed with the stated vision of IBM World Trade, “World Peace through World Trade”.  And so, I began my career journey playing a role in opening IBM’s first offices in Russia and later in China, during a time of historic global transformation

Nhã: You have had quite a career with top brand technology companies.  What motivated you; what are you most proud of during this journey?

Karen: After working in multiple countries and with people of all kinds of backgrounds and cultures, I came to realize that democratizing access to technology is key to unlocking innovation, opportunity and progress.  I became quite passionate about expanding global access to technology, ensuring that enterprises, entrepreneurs, and underserved communities can harness its power to drive meaningful change.

Creating meaningful change is not a one-time event; it’s a way of life. Sometimes this meant expanding global access. For example, I was a Director on the Gartner International Board, where we expanded into 100 countries, providing important research and expertise.  Other times democratizing access meant sharing knowledge in catastrophic times.  On 9/11, I was the General Manager of gartner.com.  There was a desperate need for expert advice on disaster back-up and recovery.  So, we opened the website providing complete access to Gartner’s proprietary disaster recovery research – no need to be a client.  The goal was to ensure that businesses and communities had the knowledge they needed in a time of crisis.

When I joined Microsoft, with responsibility for the Worldwide Financial Services Industry, the Cloud was in the early stages of revolutionizing technology. It was becoming affordable, scalable and globally accessible to individuals and organizations of all sizes.  At Microsoft, we recognized how essential it was for financial institutions to have access to a platform that accelerated innovation and could power emerging technologies like AI and big data analytics without requiring deep technical expertise or massive investment.  Cloud made it possible for the largest financial institutions to lead the way to initiatives such as Open Banking, which empowers consumers, encourages innovation and promotes financial inclusion. However, financial institutions explained that the regulatory response to the 2007- 2008 financial crisis stopped them from moving to the Cloud. The hesitancy of financial institutions and regulators to embrace the Cloud threatened innovation, progress and the ability to compete in a changing financial services landscape. So, we launched the Financial Services Cloud Advisory Council, bringing together 14 of the Global Systemically Important Financial Institutions, aka the “Too Big to Fail” banks and insurers. With support from Microsoft product, legal and corporate affairs teams, and my amazing CTO and ally, Sean Foley, we provided objective education and expertise on how cloud computing can enhance security, scalability, and accessibility. We worked with the financial institutions to define requirements and safe access.  The financial institutions shared this knowledge with regulators, and we provided the regulators with expert assurances on how to leverage Cloud safely within the required boundaries.  This led to global regulatory updates that enabled financial institutions, both large and small, to adopt cloud technologies. Our efforts helped democratize financial innovation and accelerated many initiatives, such as digital banking, e-trading and cyber-security.

Nhã: What motivated you to join Mastersfund?

Karen: Shortly after retiring from Microsoft, I attended the University of Washington Foster School of Business Women Board Directors Development Program.  I had served on a couple of Boards but wanted to learn more.   There I met an amazing woman, Gillian Muessig.  Gillian told me that, along with her colleague, Anne Kennedy, she was preparing to launch a venture fund focused on funding and advising women founders at the seed level.  I learned that women entrepreneurs were receiving only 2% of venture capital. I was shocked. There were statistics demonstrating consistently greater success of women-led businesses, but apparently this was not enough to drive the confidence investors needed to have in women founders.  Gillian asked me if I would like to join the Mastersfund launch team.

I had just spent over four decades primarily in two industries: Technology and Financial Services.  Most of the time, I was the only woman in the room.  Between spending a career in male-dominated industries and working in many different cultures, I realized I had learned strategies and approaches that I could share to help women, as well other underrepresented communities, break through barriers, so we could all benefit from their innovations.  I gladly accepted Gillian and Anne’s offer to join the team.

Nhã: As a mentor and board director, please share some of the challenges faced by founders with whom you have worked, and  how you guided them.

Karen: Answering this question briefly is tough; the stories would fill a book.  So, I will just share a few thoughts.

As mentioned earlier, it is a real challenge for women founders to raise capital. Among other things, venture and private equity investors need to have confidence in the entrepreneur’s leadership and ability to execute. When exploring potential portfolio companies, investors frequently consider the profiles of previous successful founders with powerful exits and rely on references from people they know and trust. There is a much larger history of early-stage growth companies led by men than women, so the profile of success leans strongly toward men.  Additionally, most of the venture and private equity investors are white men, frequently from Ivy League universities.  As a result, trusted referral sources are often men who are typically more experienced with and comfortable with the leadership style and success profile of other men.  Undiversified experience and references create unconscious bias.

How I guide women entrepreneurs raising capital depends on their needs. That said, in any situation, it is important to know your audience.  In my experience, men focus first on the What and Why.  They want to be confident in the entrepreneur’s vision and the potential of the BHAG (Big, Hairy Audacious Goal).  Women tend to focus on sharing the detail of How they will execute.  When much of the pitch is based on the HOW, investors, both male and female, often get the impression that the woman founder is a worker bee, not a leader.  I counsel founders to focus more on the Why and What, and be brief on the How details, just enough that the investor is aware that the founder has such knowledge.  Put the How details into an Appendix and wait until asked to share the details.

Another common challenge for women entrepreneurs is the ability to delegate – to let go.  Women are often raised to be doers, rather than delegators.  We are used to proving ourselves by doing it all. Often, I see women both wanting and struggling to keep personal control over much of their company. They strain their own physical limitations, and their success is limited by the number of hours in a day. As many also are the primary caregivers to families, the path to success is even further limited.

All leaders need to recognize their strengths and their gaps.  They need to find a way to surround themselves with team members and advisors who fill the gaps.  Founders must learn very early to delegate. They must bring a trusted team on board that can provide a full suite of skills. The founder or founders may know their product better than anyone, but a standard sign of scale for investors is the ability of someone who is not the founder(s) to sell the company’s product.  Scaling a business requires focus on creating and delivering on the company strategy.  Investors need to see that the founding team can scale, and potential customers need to see a team, not a solo entrepreneur, behind the product they are considering purchasing.  Of course, resources are limited, so it is important to manage those limited resources and put optimal teams in place.

Nhã: What is bringing you satisfaction these days?

Karen: I get great satisfaction by continuing to drive change in support of women entrepreneurs who are launching and scaling groundbreaking companies. One such company is Fyrii, an early-stage company accelerating Open Banking adoption through highly secure API orchestration and integration, thus significantly reducing costs and time-to-market, and opening doors to further financial services innovation. Another example is Looped Solutions, a leader in clandestine, secure mobile communication. Their primary market comprises victims of domestic violence and people suffering from addiction. Organizations providing help and rescue services use Looped Solutions to safely, securely and privately communicate with the people they serve.

By expanding access to technology and empowering the next generation of entrepreneurs, we are proving that innovation thrives when more voices and perspectives are included. Technologies such as AI are transforming industries and how we work.  We need these new voices and to democratize access to technology if we are going to successfully harness the combined potential of the world’s human population with artificial intelligence.  Yes, AI will replace many of today’s jobs; it will also create many new opportunities and jobs.  We need the power of both humans and technology to unlock our toughest problems and address essential questions we never even knew to ask. 

This is why I believe in bringing new and unrecognized voices to the forefront, through investors like Mastersfund, as well as building strong alliances and partnerships that create industry-wide collaborations to scale opportunities, ensure sustainability, and promote inclusive growth.