Inspirational Woman Interview: Gail Gilbert Ball


Gail Gilbert Ball is a fintech executive and the Founder and Managing Director of Chestnut Street Ventures, an alumni venture fund at the University of Pennsylvania that invests in Penn alumni-led companies. Previously, Gail has held executive positions at The Bancorp Bank, PNC Bank, Chase, Capital One, and NCO Financial Systems. In addition, Gail headed the Payments Studies Group at the Richmond Federal Reserve and was also a Board Member and Risk Committee Chair at Kompanion, one of Central Asia’s largest microfinance institutions. She started her career at Mellon Bank in corporate development, where she identified and led mergers and acquisitions transactions. Gail has a Bachelor of Science in Economics with concentrations in Finance and Statistics from the Wharton School of the University of Pennsylvania. She is a member of multiple entrepreneurial, venture capital, and financial interest groups, including On Startups and Global Financial Markets.

Can you tell us about your work as Managing Director of Chestnut Street Ventures and how you came to found it?

Gail Gilbert Ball: Chestnut Street Ventures is a community of Penn alums who want to foster the Penn entrepreneurial ecosystem. As Managing Partner (MP), I have created and lead a community to help accredited alumni investors intelligently add venture capital and other hard-to-access alternative investments to their portfolios. That involves driving fundraising, investing, and community relations. Essentially, I spend my days learning from, being inspired by, and serving entrepreneurial Penn grads.

I am a poster child for the LinkedIn job offer engine. One day I got a routine ‘We have 10 jobs for you’ LinkedIn message. That day, I opened the email and found that Launch Angels, an umbrella organization that manages a series of sibling alumni venture funds, was looking for an MP for Chestnut Street Ventures.

What are some opportunities Chestnut Street Ventures provides for investors?

Gail Gilbert Ball: Investors in Chestnut Street Ventures funds enjoy many opportunities. Most fundamentally, we provide investors exposure to a key but hard-to-access asset class, helping them create a venture portfolio of 15-25 diverse companies. Beyond that, we invite investors to participate as portfolio company mentors, deal consultants, and deal referral sources. One step further is our Investment Committee, consisting of about a dozen of our investors. This group of experienced business professionals advises us on deals, lending their expertise and judgment to our deal evaluation meetings.

Can you tell us about some of Chestnut Street Ventures’ portfolio companies and co-investment deals?

Gail Gilbert Ball: It’s still very early in our fund’s life, but we have already started building a portfolio. We have invested in a company founded by two Penn grads, Better View, a SaaS company leveraging drones, image management, and machine learning to provide unique services for the commercial insurance industry. Chestnut Street Ventures also participated in one of our sibling fund’s investments in Domo, a clear market leader in the business intelligence category with a world-class solution and deep traction with blue chip customers.

In your view, what are the main areas of need and challenges facing fintech going forward?

Gail Gilbert Ball: I continue to believe that as we apply new technologies to legacy financial business processes, we create gaps between how we perceive financial transactions are settled and how they are in fact settled. Information flows at one pace and funds at a much different pace, creating risks that are not well measured, monitored, or mitigated for all parties in the value chain. The application of technology to building new business processes and settlement systems has been much slower than the great strides in user interfaces and underwriting/decision making for both deposit and credit products.

What are some of the biggest challenges you’ve faced in your work and how did you overcome them?

Gail Gilbert Ball: The success of all work — whether performed as a sole contributor, a team member, or a team leader — and all workplaces depend in great measure on relationships with and understanding of others. Whether relationship building seems like an obstacle to overcome or a benefit to be sustained, I always rely on my version of the three R’s:

  1. Respect: If you don’t know enough to ‘put yourself in the other person’s shoes’, then you don’t know enough to be respectful of their perspective.
  2. Resourcefulness: If you haven’t offered something that you have (knowledge, access, tools), then the relationship doesn’t have access to all the resources it should know it has to get the work done.
  3. Resilience: If you haven’t been relentless in planning, then it will be harder than need be to keep progressing after an unexpected outcome.

Can you talk about one woman who has impacted your life?

Gail Gilbert Ball: I am a constant reader and many women authors have been a source of inspiration for me. My family has also had a huge impact. I am very proud of my mother who first followed the standard of her time — getting married while in college and leaving school — then went back for her degree and later found herself in the workplace out of necessity. In short order, she rose to roles integral to the mergers of today’s top domestic banks. But as I reflect, the woman who has most impacted my life by modeling and achieving work/life balance and the pursuit of justice is my paternal grandmother. She was an award-winning teacher, a much-honored civic leader, and a national volunteer leader in social justice causes —including assisting Jews resettling in the US before, during, and after World War II.

What is your advice for individuals interested in pursuing banking and corporate finance careers?

Gail Gilbert Ball: For these roles and others, especially in finance and banking, develop these four qualities to succeed:

  • very strong numeracy (which can show up as math, accounting, coding, data analytics)
  • a sense of personal accountability and urgency
  • unwavering honesty
  • and making it a joy for others to come to work with you because there are tough problems to negotiate and solve every day!

What are your favorite books, films, websites and resources related to finance and technology?

Gail Gilbert Ball: Every day, I read the New York Times and Bloomberg View. On Bloomberg View, I devour every word that Matt Levine and Noah Feldman write — and every day, I learn new things from reading both of them.

I read a lot of non-fiction, and I recommend everything by Michael Lewis. I continue to be fascinated by Flash Boys because the story is still playing out.  I have loved behavioral economics since I read The Selfish Gene in 1976 and I find current work by Adam Grant, Dan Ariely, Richard Thaler, and Cass Sunstein, plus Michael Lewis’ recent book The Undoing Project, chronicling the work of Twersky and Kahneman, to  be very thought provoking and actionable.

Much of today’s technology advances rely on quantum mechanics and physics, and I love to read layperson’s books in this space. My favorite is Absolute Zero and the Conquest of Cold by Tom Schachtman, and my second favorite is The Elegant Universe by Brian Greene.

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