She-VC: Rudina Seseri on System Thinking and Mental Model for Investing in Frontier Techs in AI

Rudina Seseri is Founder and Managing Partner of Glasswing Ventures, leading the firm’s investments in Artificial Intelligence (AI) enabled enterprise software as a service (SaaS), cloud, Information Technology (IT) software, and vertical markets. Rudina has led investments and held Board of Directors roles at ChaosSearch, CloudTruth, inrupt, Navigant (acquired by Veritas), Plannuh, Reprise, Talla, Verusen, Zylotech, Celtra, CrowdTwist (acquired by Oracle), and SocialFlow.

Rudina has 17 years of investing and operational experience in high growth companies in IT software, cloud and enterprise SaaS. Previously, Rudina was a Senior Manager in the Corporate Development Group at Microsoft Corporation. In this role, she led a number of successful acquisitions including iView Multimedia, Massive Interactive, Bungie Studios restructuring (creator of the Halo franchise), Deep Metrix, and Lionhead Studios. Prior to Microsoft, she was an investment banker in the Technology Group at Credit Suisse responsible for multibillion-dollar acquisitions and financings.

Rudina has been appointed by the Dean of the Harvard Business School (HBS) for five consecutive years to serve as Entrepreneur-In-Residence for the Business School and is an HBS inaugural member of Rock Venture Capital Partners. She is also a Member of the Business Leadership Council of Wellesley College and was previously an Advisor for GSK Consumer.

Previously, Rudina has served as Chair of the Board of Overseers for the FutureM, a conference with 2,500 technology innovators and digital executives. Her philanthropic work includes serving on the Philanthropy Board for Boston Children’s Hospital as Vice-Chairwoman.

Entrepreneur Magazine has named Rudina Seseri to their 2019 100 Powerful Women list. She is a Boston Business Journal Power 50: Newsmaker, a Women to Watch honoree by Mass High Tech and a Boston Business Journal 40-under-40 honoree — recognized for her professional accomplishments and community involvement. Rudina has been published in TechCrunch, Forbes, Quartz, VentureBeat, GigaOm, and other leading business publications. She graduated magna cum laude from Wellesley College with a BA in Economics and International Relations and holds an MBA from HBS. She is a member of Phi Beta Kappa and Omicron Delta Epsilon honor societies.

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Here are the She-VC Questions:

1. You have invested in some of the most innovative AI startups that includes Inrupt by Sir Tim Burners Lee. Considering the threat that we are living in right now how do you think AI can help us better prepare for the next invasion? Why did you decide to focus on specifically frontier technologies in AI?

2. VC is a very hard industry to prepare for. There is no MBA or coursework that prepares you for early stage investing. You came into this country as an immigrant from Albania and rose to a Partner role and then you founded your own AI fund Glasswing Ventures . Tell me about how your past experiences helped you to start your own AI fund.

3. It is said that the venture capital is all about identifying patterns in time. Yet we are seeing how our policy leaders have failed to recognize the patterns of other infected countries and now we are all in this to flatten the curve. Unpredictability is a pattern of our life now.

Bigger Innovative ideas are unpredictable and sometimes challenging to many people. Sometimes those investment decisions can be non-consensus among Partners. To invest in such unpredictable big ideas one has to learn and see things differently, analyze markets that others are finding it non-sexy to invest in. What kind of system thinking and mental models do you approach to back such investments.

4. Once the pandemic settles, can you elaborate about the new market opportunities for deep tech investment globally and the importance of AI in such endeavors?

5. How do you think Coronavirus affects your AI portfolio startups? How do you think they should embrace these sudden changes?

6. You are the first woman founder of an AI venture capital fund. Maybe in the world.

Venture Capital is one industry that has not been disrupted. As we are seeing more people bringing movement into this industry, how do you see biases and prejudices that played in the past come in effect for people like you who are catalysts for change.

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