Episode 13 - Disrupt Yourself or Be Disrupted: The Challenge for Every Enterprise w/ Rudina Seseri of Glasswing



Episode 13 - Disrupt Yourself, or Be Disrupted: The Challenge for Every Enterprise w/ Rudina Seseri of Glasswing Ventures


Dave Knox:                         I'm your host Dave Knox and this is Predicting The Turn, a show that helps business leaders meet their industries inevitable disruption head on.

Dave Knox:                         Welcome to another episode of Predicting The Turn. Today I'm joined with my good friend, Rudina Seseri, who is the managing partner of Glasswing Ventures. Rudina, welcome to the show.

Rudina Seseri:                   Thank you Dave, I'm excited to be here.

Dave Knox:                         Thank you. I'd love to start with talking a little bit about your journey that your career has taken. Moving from investment banking to corporate development at Microsoft, and then ultimately into the world of venture capital with Fairhaven and now with Glasswing Ventures. What led you down to the path of where you are today?

Rudina Seseri:                   It's been an interesting journey and as careers go, I can tell you that this was the path I had laid out for myself, but it has been a wonderful and rewarding path. And if you look at it, the common theme across my various roles, honestly starting from the day I graduated Wellesley and worked on Wall Street is technology. I joined the technology group at Credit Suisse at the time as a young college graduate. While finance and investment banking was all great, the passion that truly emerged was around tech and the transformative impact that technology was having.

Rudina Seseri:                   After business school, I joined Microsoft, focused on their acquisitions and some investments and then from there, moved onto the venture world. So with every step I've taken, I've gotten closer and closer to, sort of fulfilling what has turned out to be a deep desire around driving transformation through innovation and technology. So that's really the reason behind the path that has taken shape.

Dave Knox:                         Perfect. And we first met because of your involvement in SAS marketing technology, some great startups like crowdTwist and SocialFlow and Celtra, those investments gave you a front row seat in how the marketing industry is changing. What did these entrepreneurs and you as an investor see in terms of the future of things like loyalty marketing and advertising, creative and social publishing.

Rudina Seseri:                   Yeah, I'm gonna now date myself a bit, but a number of these investments are now six, seven, eight years old. So we're truly looking sort of in the 2010 timeframe, and what was fundamental about that period and the investment that I made was the fact that digital was changing everything. And brands at the highest level, particularly consumer facing brands, had a new opportunity that had been previously unfathomable in that they could get direct access to their consumers. I mean, let's go back a bit, could any given brand that didn't have a direct retail store they owned ever have disturbed chain and their relationships with retailers to try to get access to the consumers? Absolutely not.

Rudina Seseri:                   Yet with the advent of digital, an entirely new marketing opportunity and a new opportunity to establish direct relationships with consumers were created, the result of that has been multifaceted. In today's world, we really think of it as cloud marketing and that's all encompassing of anything from the distribution where programmatic has taken over, I.e. powered by data, to loyalty as another mechanism for honestly getting a 360 view of a consumer, not just on digital including mobile, whether it's app or mobile web, desktop, physical and a brick and mortar. Loyalty is one of the mechanisms and one of the more differentiated mechanisms to get a full 360 view.

Rudina Seseri:                   And you mentioned CrowdTwists, a portfolio company that focuses in that area, but all the way from that to the delivery has been worked out to how do you intelligently deliver the creative, the last bit in this world of what can you automate and drive by data. So I would say that whole learning experience has been very interesting and it has evolved and changed, initially just the access to consumers now a lot more leveraging intelligence and machine learning to deliver what, in Glasswing we would coin this term around personalization and hyper-personalization at scale. You build it once but you make it highly personable to any given consumer, and again we're seeing that even more around new plays.

Rudina Seseri:                   I have a company called Zilo Tech in the CDP, customer data platform markets. So a whole new category of fairly noisy category with large budgets but big opportunities for transformation of how brands and consumers interact with each other.

Dave Knox:                         Speaking of that, you mentioned Glasswing in that answer, and last year you announced the launch of Glasswing as the managing partner for the fund. With Glasswing your focus on early stage AI and complimentary frontier technology startups that are, as you say, enabling the rise of the intelligent enterprise. What led you to that focus of this area for your debut fund?

Rudina Seseri:                   So the funding, and we formed the firm in 2015, and I point that out because while today is speaking about AI, it's almost an overused term in certain regards. In 2015, I'm quite proud of the fact that we were visionary in what was happening around the rise of both deep learning as I would say, the impetus for the current, the wave and the current paradigm of narrow AI adoption and intelligence adoption as well as the amount, and the diversity of data that was being created given pervasive connectivity. So the processing power, the large amounts of data and the large, you know, the voracity and the diversity of data. And thirdly, the breakthroughs- you know, in machine learning, particularly around deep learning, those three driving forces created a trifecta that in our view was going to enable a new wave of disruption around AI.

Rudina Seseri:                   And we that impetus and with that sort of schematic view, we believe that it would be a transformative opportunity across the enterprise platform for [inaudible 00:07:16] the cyber security market. And that was the genesis of why we form GlassWing and launched the firm. And as I look back 18, 24 months now, the of the fund deployed, the potential- we've only scratched the surface while the term may be overused. The reality is that we've just gone from an era of data analytics to predictive, which is why, you know, there's a lot of discussion around predictive and yet at GlassWing, which will we believe that the real opportunity around the intelligence enterprise is not just to predict whats going to happen. We talked a bit about marketing, but we have investments around data infrastructure and Dev ops and other areas of the enterprise, it's not just about being able to tell in advance what's going to happen in an intelligent manner.

Rudina Seseri:                   We think about predictive. So in many ways I think we're still visionary and how we view the market shaping up in that, and by prescriptive I mean data informing us of what should happen to achieve optimal outcomes that we are seeking. So there's a lot of opportunity around that. But to come back to your question, there was the genesis of GlassWing and even more fundamentally the idea, again going back to your first question, of driving transformation and being part of shaping the wave around not just AI as a driving force, but of responsible AI. And GlassWing's roots, even the name it's a butterfly, so the idea of transformation within that butterfly, much like startups become large companies. And perhaps lastly is that, Joe, quite often I called the entrepreneurial bug and I and my partner, who would be Grinnell, we're ready to take on our own entrepreneurial your journey in that regard.

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Dave Knox:                         Yeah. So speaking of that entrepreneurial journey, this has been you launching your own business, you know everything that goes into it. What lessons have you learned in that journey of launching your own company alongside doing investing?

Rudina Seseri:                   I would say it's probably been the hardest undertaking and the most fulfilling undertaking I've ever done. I've never worked harder and I've never been happier and this because I think both in that kind of like a baby, you're shaping it and you're giving it life, but also the ability to shape culture and in the heavy burden at the same time to shift culture, to shave processes, to think about what will GlassWing stand for, what should our team look like and more core to our business, how do we add value for our founders or prospective founders. It's not just about, 'oh, we know the space, it's intelligence capital', no pun intended. It's about really being, especially for early stage, hand in hand with your founders. Yes, we take bore cts, yes were driving terms, but this is not an exercise in who's high and mighty on the broad of directors. This is an exercise of being an extension to the team and helping them, whether it is adding new team members, as the management team and beyond gets built out. Whether it is helping them land their first customers, whether it is focusing on pricing, you know, go to market, whatever it helped that might need.

Rudina Seseri:                   So as I think about our journey though, the core is perhaps, and most importantly, we relate to our funders at the most direct level. We know what it takes to get a company built from the ground up. We know what it takes to fundraise. We don't have the software or another solution to show. We had our track record, a successful track record, but nonetheless to use and to go and raise institutional capital as we did. so we know the hunger, the drive, and the unwavering commitment that's required to be a founder. And I think that makes us better investors.

Dave Knox:                         Yeah, without a doubt. I love that. So you're taking a slightly different tact with your time at Microsoft and your former venture fund, you were really helping corporations and their efforts around startup engagement. Why do you think it's important for large companies to be involved in the startup ecosystem, whether it is as an investor, acquirer, or a partner?

Rudina Seseri:                   Well, a couple of answers to that question. At the highest level, because any business no matter what vertical or market it's operating in, is a tech enabled business in this day and age. And the expectations of customers, whether they're, you know, enterprise customers or consumers are increasing. The responsiveness or time to responsiveness is getting shorter and shorter, at least from a customer's point of view. And the demands of the three constituents- so customers, employees, and perhaps regulators as an external force, are also changing. Regulators often lagging, but the employees are expecting just in time feedback, and especially with the rise of the millennials is a major force in the labor markets. They're expecting certain feedbacks are expecting tech savvy engagement customers as well. And the regulators are having to respond, especially when it comes to data privacy and other matters of importance. So with that changing, today's large incumbent may be tomorrow's fall on empire. It is not a coincidence that every large fortune 100, 500, whatever one wants to cut the data, has some major digital transformation effort under way.

Rudina Seseri:                   And it's interesting because in my view you ask 10 companies and enterprises what they mean by 'digital transformation' and you will get 10 different answer. What's common though is the fact that they recognize the need to change where technology data and more recently machine learning and AI, at times is a buzzword to be perfectly honest, are driving it- you know, are driving and critical components of the transformation. So to come back to your question, if that is happening, one way to do so and both remain relevant but also help transform oneself as a large enterprise is through the startup ecosystem and varying degrees of engagement in that ecosystem. Whatever forms they may take, as you outlined a couple of options, from my perspective as a VC, I think about it both in terms of helping large enterprises acquire cutting edge software. But also in my day role enabling my companies to land their first customers, those first critical logos. So I view it both as a contribution to the broader ecosystem and also as an opportunity to help and add value to our founders and portfolio companies.

Dave Knox:                         So speaking of engagement, you've really stayed actively involved in both of your Alma maters with Wellesley and with Harvard Business School. And with HBS in particular you served for the last five years as an Entrepreneur In Residence and had been involved with Rock VC. Why have you found important to prioritize this involvement with the educational community?

Rudina Seseri:                   I think both because a lot of what's happening in this space that we invest in, comes out of academia. I think about you know, machine learning and deep learning and in general this whole field of computing and AI will, you'd be hard pressed to find many individuals over the age of, I don't know, 45 that have training. In fact, if anything overall in the U.S., there is shortage of this capability and of the necessary training on what's happening around data sciences and albeit, I think it's a short term challenge because a lot of these higher ed institutions that are investing in the category. But if you are going to find the talent, oftentimes talent is coming out of the institutions. So for one very practical reason, I would be doing myself and ecosystem of disservice now that we have an ear to the ground. Secondly, because I think out of the HBS and actually for the broader university, much like my partners do at other schools, MIT and elsewhere, there's lots of new and entrepreneurial ideas coming out and then businesses being formed. So while we both want to add value and be helpful mentors as well as have an opportunity to learn about these upcoming ideas.

Rudina Seseri:                   And lastly, this pertains to both HBS but perhaps I have a bit of a softer spot for Wellesley, it's important to me personally to give back to both schools. But for Wellesley, in particular around the women focus and changing the dynamics around women in tech and women in venture capital. This need is, in my view, even more pressing when you think about AI and machine learning and how the neural nets and the algorithms are being built and wired. And as a woman and as a mother of a daughter, I do worry about AI being ethical, being fair, and not belonging to a given gender because the gender coded and built the algorithms. So I think anything I can do to help drive change in the ecosystem, I think it's important and it's important not only on a normative basis, 'Oh, I was right or wrong', it's important because it's good business.

Rudina Seseri:                   We are in the world of startups in the world of innovation. And the more creativity and the more diversity of thinking we have, the better the outcomes. And right now the percentages of women involvement and other minority involvement for that matter in our space, leaves much to be desired.

Dave Knox:                         Yup, no, those are great points. I love that combination of it's good business to really think about how do you tie it in and help make sure the change is being changed in the right way versus not thinking it through all the ways there.

Rudina Seseri:                   Absolutely- [crosstalk 00:19:12] no, go ahead.

Dave Knox:                         So one of the things I'd love to touch upon is, you know, you're spending your time on frontier technology and that by nature is putting you on the very bleeding edge of what's taking place in a lot of different spaces and industries. What are you doing to, you know, think about your own personal development, to stay ahead of these technology trends and these industry trends because you're looking at companies that it's very much at the early stages. So how do you keep yourself being on top of those things as you evaluate investments?

Rudina Seseri:                   I will start by saying it's an existential challenge that I'm constantly working on. It comes in many, many forms. It comes in, 'what do I read? What moods am I taking online?', who I surround myself with at the highest level, as you share and you know, at GlassWings invests in BDB companies that leverage machine learning and AI. And you know, my part, one of my partners [inaudible 00:20:14] Grinnell specializes in cyber security. I have another partner who is more on the digital side of things. I specialize in enterprise. So one area I'll focus this perpetually there if you will, is the enterprise focus.

Rudina Seseri:                   So you're not for the last 15 years that driving forces in the market dynamics in the various areas of enterprise have become second nature. The question often is, and then, 'okay, what technology is going to drive the next wave of disruption and and how will the market respond? Which verticals'- if it's a vertical play or which platforms will win. And there I think it's both. Like I said, I'm constantly reading but also surrounding myself externally with advisors who are either in academia or in industry at the cutting edge for every area that I know there is someone out there that can go a lot more deeply. So my goal is one, to have access to those people and two, to educate myself as much as I can, such as I can in turn add value to my own portfolio companies.

Dave Knox:                         And the way- [crosstalk 00:21:26]

Rudina Seseri:                   If I make them [inaudible 00:21:28] to that, and you know this from your personal experience, but we have actually what I just shared with you, formalize that view, and we have 33 advisors out of academia and industry and the startup ecosystem who work with GlassWing exclusively in part to address that very need. And I mentioned the fact that it's exclusive because these individuals are not just big names and a website and you check the box. These are individuals who commit a certain amount of time and truly play a fundamental role in adding value to our overall portfolio and fund, including the facets we've just covered.

Dave Knox:                         Without a doubt. And you mentioned that you've got those industry leaders involved. What do you think industry leaders need to do to reapply the principal and the mindset that you have to keep themselves on kind of that forefront of where change is going, given that industry change is happening kind of at an unprecedented pace these days?

Rudina Seseri:                   I mean, I think at the highest level of willingness to disrupt themselves because if they don't, someone else will, another company will. And that may come in the form of reinventing one business, taking risks that may even negatively impact existing revenue streams and cash flows, which is a very hard thing to do. How do you transform, if you have Wall Street expectations and broader market shareholder expectations, yet you know for a fact that if you don't do something about the present day challenges, 5 to 10 years from now you may cease to exist. So balancing those and having that sense of urgency, I think it's fundamentally important. And and then getting to the 'how', first grappling grabs, but then you know, internalizing the 'what' of what needs to happen and then focusing on the 'how' and if the timeframe for something [inaudible 00:23:37] of transformation is 'x', knowing that someone else somewhere else is doing it in half the time.

Dave Knox:                         That's perfect. Well thank you so much Rudina it's always an amazing conversation that has my, my wheels spinning at the end of it. So thank you for taking the time and telling the story of GlassWing.

Rudina Seseri:                   My pleasure and thank you for having me and I so enjoy working together. This has just been a joy. Thank you.

Dave Knox:                         Thank you, and if somebody wants to find out about GlassWing, what's the best way to learn more?

Rudina Seseri:                   GlassWing.VC, for venture capital.

Dave Knox:                         Perfect. Well thank you again, and I look forward to talking again real soon.

Rudina Seseri:                   As do I, thank you.