Glasswing Ventures Rudina Seseri on frontier tech, the KPI's Glasswing uses to measure their value-add to founders, and why diversity is central to their investing ethos

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

Today, we have the great pleasure of chatting with Rudina Seseri, Founder of Glasswing Ventures, an early-stage venture capital firm investing in AI-powered software companies. With over 17 years of investing and related experience, Rudina has led investments in companies such as Celtra, Crowdtwist, ChaosSearch, Plannuh, Reprise, Inrupt, and Zylotech (recently acquired by Terminus).

Prior to moving into venture capital, Rudina was a Senior Manager in the Corporate Development Group at Microsoft Corporation and started her career as an investment banker at Credit Suisse. Rudina was appointed by the Dean of the Harvard Business School (HBS) for four consecutive years to serve as Entrepreneur-In-Residence for the Business School and has most recently been named to the HBS inaugural group of Rock Venture Capital Partners.

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In this episode we discuss:

01:01 What inspired Rudina to become a full-time investor and what was her early investing philosophy

03:06 The firm’s structure and methodology

05:42 Learnings from the first fundraise

08:35 Frontier tech investing

12:13 What type of frontier tech companies the firm looks for

14:11 How Glasswing specifically evaluates companies

21:01 How they thoughtfully built the team at Glasswing to drive unique support to their founders

25:03 Preserving ownership in companies during the current market conditions without having to substantially increase fund size

28:36 Deciding on when to make an exception on valuation or ownership

30:44 How the firm deals with unconscious bias and group think when evaluating investments

34:50 Using diversity of thought to drive better decision making

38:55 The most counterintuitive lesson Rudina has learned as a VC

40:52 The investing miss that taught her a lesson

42:13 The investor she most admires

Mentioned in this episode:Glasswing Ventures

I’d love to know what you took away from this conversation with Rudina. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.

Transcript:

Samir Kaji:

Hi, I'm Samir Kaji, welcome to another episode of Venture Unlocked, the podcast that takes you behind the scenes of the business of venture capital. Today, we have the great pleasure of chatting with Rudina Seseri, founder of Glasswing Ventures, an early stage venture firm investing in AI power technology companies. With over 17 years of investing in transactional experience, Rudina has led investments in companies such as Celtra, CrowdTwist, Talla, and Zylotech. During our discussion, we talked about her view of what frontier tech means to them, the KPIs that Glasswing uses when measuring value add services to founders, and why diversity is so central to their investing ethos. Now, let's get into the episode to hear all of them and more. Rudina, it's great to see you and thanks for being on the show.

Rudina Seseri:

Hello, Samir, happy summer and thank you for having me.

Samir Kaji:

Now, let's get into your start into venture capital. You had a myriad of other roles before you became a full-time investor. What inspired you to be a full-time investor? What was the opportunity you saw and what type of investment philosophy did you have?

Rudina Seseri:

I had been in investment banking as a little low analyst. Remember those? 120-hour weeks. And I was in tech investment banking. So I joke that after three years of investment banking, I was done with the banking hours, but I had permanently caught the tech bug. So and this was the early 2000s, both the bubble and the burr. So both sides of that equation, but really became hooked and was excited by the innovation and the transformation and that passion. So, I knew I wanted to do tech of some sort and VC sounded very, very sexy. Have you met an MBA that doesn't love VC? So, I went to HBS to get my MBA and there I met Rick Grinnell, who was already a VC, and not coincidentally today my co-founder and partner at Glasswing Ventures.

Rudina Seseri:

We launched the firm together, but Rick was already a VC. And as a student, I actually did a few projects with him, particularly one around the mobile landscape. Mobile and smartphones were going to be a big thing. This is 2003 and 2004. And then I went on to join Microsoft, always with an idea that four or five years down the road, I would come back to venture and the notion of balancing sort of the passionate for tech and the background in M&A and financing, et cetera, with operational experience at Microsoft. It happened sooner than I expected under two years because Rick and our old firm were raising a new fund and they were building the team, so they poached me, but that was sort of the genesis of my coming onto venture. Put differently, on a good day, I thank Rick. On a bad day, I blame Rick for my venturing experience.

Samir Kaji:

I think it can be a little bit of a roller coaster for sure. And the two of you did launch Glasswing in 2016, you're effectively a lift out. Tell us a little bit about Glasswing itself and what really catalyzed the start of that firm.

Rudina Seseri:

So the idea was that while we were in our old firm, we kept seeing opportunities around sort of the evolution, if you will, of frontier tech, particularly having crossed the chasm from advanced analytics to something else, which became really AI and narrow AI and applied AI these days. But we kept evolving our thesis in that regard and we're seeing the impact because we're end market investors, so we look at enterprise security platforms but with an angle around frontier tech and this is going back really to the sort of 2012 through '14 timeframe.

Rudina Seseri:

We were particularly seeing that emerge out of academia with deep learning. And some of the emergence of that wave and making its way into academics and, fundamentally, all our thesis and the investments we had made were telling us that it was going to become all pervasive. It may sound strange today in 2021, but there were a lot of nonbelievers. I mean, when we did the spinout to have this focus around frontier tech with their AI and applied AI being a driver, I had many, many, many questions around, was AI really a thing? Was it really a wave? So you look back and you're like, "oh, my gosh. Now, it's an entirely forgotten conclusion." But from the perspective of the time, we really thought there was a big, big market opportunity for a focused strategy. And so far, so good, knock on wood, but it has panned out quite nicely.

Samir Kaji:

There's a number of ways that people start their own firms. It's usually with a few backgrounds. They were an angel investor and decided to be a full-time investor. Somebody that was an entrepreneur, an operator that decided to be a full-time investor. And then sometimes, it's coming out of another shop and starting really your own firm. And the latter is kind of where you and Rick were. The two of you had worked together for almost a decade investing, started Glasswing in 2016 as a newly formed firm. But a lot of people asked me the question when I have people that are effectively spinouts, do…