Silicon Valley VC Shares Insider Tips for Tech Founders & Other Investors

Special guest Divya Raghavan is a venture capitalist at Hitachi Ventures in Palo Alto, California. She shares details with Trevor & Rob about her route into the profession, and what the key success factors are in today's dramatically different tech investment world.  You will also learn why she thinks Canada's tech startups and scaleups are such attractive investments now.  This episode of High Octane Friends is a must listen for all aspiring VC, ambitious tech founders and everyone else supporting them to grow.

The High Octane Friends podcast is where Rob McMullan & Trevor McKee discuss a variety of subjects in an authentic and unvarnished way. 

Rob McMullan LinkedIn
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High Octane Friends website
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Transcript

SPEAKER_04 0:00

Now? Oh, perfect. Hi. Hi out there in Hi Octane Friendslands. I can't even say the name of our podcast properly because I'm so high in medications and these are illegal anti-histogene.

SPEAKER_05 0:14

Prescription, prescription medication.

SPEAKER_04 0:15

Prescription in my hand. I didn't know we were starting recording. So to show you all the many hordes of listeners while I'm speaking again into the future, that we really have minimal prep here. And it is all to kind of you know show you this is just who we are. So great things are gonna bubble up today because we have someone really special and out of Silicon Valley, no less. And I'm gonna attempt to pronounce your name right. Diviya, I believe, is the pronunciation of your first name, right? But then Rai Kavan, you got it right. Oh, there you go. So who is with Hitachi Ventures? My my son thinks I'm so pretentious because I lived in Japan a long time, and so I feel like I have to pronounce it the right way.

SPEAKER_00 1:05

I know I learned it as well after joining. It's uh Hitachi, not Hitachi.

SPEAKER_04 1:13

Yeah, which is obviously part of a huge, I guess you could say, conglomerate. And you are it's a pretty big fund, I think. Uh Hitachi Ventures, isn't it?

SPEAKER_03 1:23

Yeah, close to one billion in the UN.

SPEAKER_04 1:25

There you go. Well, so we're we're gonna get into your backstory and whatnot, and just to remind everybody. So another, oh gee whiz, we have two MIT years and a Harvard dropout. As I was joking today, so Harvard dropout that's equivalent to like MIT masters or PhD, right? Or still I like to kid myself anyway. Um, my missbent youth, Trevor. Gee, it's been a while, eh, buddy, since this morning when we did our event.

SPEAKER_06 1:54

Yes, it's true. Yeah, yeah, yeah. Well, and then before that, well, it's it's just been a busy couple of weeks. So uh I just came back from New York Tech Week, which was uh being run by uh 16c, yeah. And uh and a lot of a lot of like places we couldn't get into or like we we were waitlisted, and then some that we got into, and then others that friends got into and just told us where it was, and we just showed up. So oh, there you go.

SPEAKER_02 2:21

That's the best way to do it.

SPEAKER_06 2:23

Yeah, yeah. Well, we we we had one one year where they actually they did like a two-factor authentication. You had to have the have the wrist strap and the badge. And so then so then we just had uh we had a line of of of our we had one extra wristband and badge, and then we would sneak it out. We'd sneak well well, we we'd bring it to the back fence, pass it over the back fence to the other guy, and then they would come in and then they pass it over the media.

SPEAKER_04 2:56

That's that's the IQ test, right? Yeah, like it was actually all by design. They they they're just putting this in to you know, let you show your your your metal.

SPEAKER_06 3:06

How do you keep uh entrepreneurs out of places you don't? You just uh you just account you just account for the loss, right? You just account for the loss.

SPEAKER_04 3:17

Like if we they weren't like that, if we weren't like that, then you wouldn't have the likes of Uber, which like really shouldn't legally exist in many cases.

SPEAKER_06 3:26

Right, right, right, right, right. Yeah, yeah. It's better to ask forgiveness than permission, right?

SPEAKER_04 3:32

So yeah, so I'm gonna just randomly ask you a question, Divya, and because like every single one, it's it's almost like uh roulette here. Completely random question. Do you like the color forest green?

SPEAKER_03 3:48

Forest green, okay.

SPEAKER_04 3:50

Uh metal oh let me be more specific. Do you like metallic forest green? Feel free to say no, it's awful.

SPEAKER_03 4:00

Uh maybe not on a wall, but it depends on where it's applied. Like, you know, would you if it's like if you're asking me for a forest green jacket, maybe not. No. Uh, but I'm I'm trying to think of in what context might make sense.

SPEAKER_04 4:13

How about honorable?

SPEAKER_03 4:14

No, I would say I'll just go with no. I'll just go with no.

unknown 4:17

No.

SPEAKER_04 4:17

It's the simple one. It's the simple one. So this is really just a way to you know introduce you or let you introduce yourself. Tell us your story a little bit. What excites you? What do you really like? And maybe even what do you really not like? What do you avoid, whether it's work or you know, anywhere, any other sphere of your life?

SPEAKER_03 4:39

Sure. That's a I I see two questions. One, I'm going to take the chance to introduce myself, just give a little backstory, and then I'll go into your second part, which was about what I like, what I don't like, and I'll try to keep it venture, startup, world-specific, but again, we all bring our full selves to work, right? So you might see some personal elements as well there. So my backstory. So I grew up in India. So my story in the US is the classic immigrant story. So I came here for my education. And before I kind of delve into my the you know, adult life, I think a big part of my growing up in India was the household which I grew up in. My father was a first-generation entrepreneur, and this was back in the 1980s when it was almost a taboo for someone in India to start a company or even think about starting a company. So he and his co-founders, who were there were three other co-founders, decided to. So they were at this organization called Larson and True Tubun, which was at that point in time one of the engineering powerhouses. Like, you know, so they used, they were working there and then decided to, you know, start something of their own, which is in the manufacturing space. So I've seen the personal side of entrepreneurship growing up as a child and how much it can kind of you know move the needle of one's life. And that has kind of been a big element of my entire adult life. Like, you know, so I've always done things or seek to do things which where I can bring my own entrepreneur hat. And you know, also again, so that's my backstory growing up in India, and of course, did my undergrad, everything in India, and moved here for my master's. So I went to University of Florida, Gainesville. Uh, if you're familiar with the US could uh football scene, it's one of the you know go-to schools for that. Of course, I didn't go there for the partying or the football association. I thought football was a one-hour game, like you know, but I didn't realize the clocks get stopped, like, you know, for four hours. But anyway, so did my master's in computer science at University of Florida and then took the path of working in Silicon Valley for a few different companies. Started off uh on the engineering, software engineering side with Citrix, where I built and shipped products, what is today called the you know, desktop virtualization as well as mobile device management offerings. And of course, uh Citrix is one of those rare companies that was in the core enterprise infrastructure layer, like you know, a lot of the VPN virtualization, et cetera. So I kind of developed a sense of infrastructure software during my time building code and building and writing code at Citrix. But at the same time, I always had a curiosity of why are we doing this? What's the you know value of the in the market, et cetera? So that curiosity kind of led me down the path of what is called product management, which is at the intersection of engineering and commercial uh sense, right? So did product management for a few years. I was with a venture-backed startup called Sugar CRM, where I led a lot of the developer-facing care, you know, capabilities, and then took a break to go to business school. So I went to MIT Sloan. I always joke that uh course 15, as it's known within the MIT ecosystem, is like the black sheep uh within the MIT.

SPEAKER_00 8:02

I'm sorry?

SPEAKER_06 8:04

Well, that's the course course 15 is is the degree program for management. So each each each course courses mean course means degree program at MIT, and each course has a number unless you're grad only, in which case you have letters. So when I was there, I started out as course as as as BEH, Bioengineering and Environmental Health. And then when I after I left, it became a full graduate and undergraduate course and was became course 20. So yeah, yeah. Okay.

SPEAKER_04 8:36

I yeah, because I I took some courses at MIT, even though I was down the street, and they were yeah, 15 something, 1500 something.

SPEAKER_03 8:44

So it's true, so that's the management school, which is kind of an anomaly in you know, in a school like MIT, which specializes in uh you know engineering, core engineering, yes.

SPEAKER_00 8:55

So that's why I call us the black sheep of the MIT uh list of courses.

SPEAKER_06 8:59

But there was did you ever go to the Muddy Charles pub?

SPEAKER_02 9:04

Yes, I do, yeah, yeah, yeah, yeah.

SPEAKER_06 9:06

So the number of the number of startups that have emerged from the Muddy Charles pub, given that it was sort of equidistant from the engineering school and from the business school. Yep. Yeah, I mean in the middle, literally.

SPEAKER_03 9:21

Exactly, exactly, exactly. But fun times, like you know, so uh went to MIT Sloan, and also then once during my time at Sloan, it was a little bit of an exploration of what I wanted to do. I think like any classic business school. At the same time, I started working with a bunch of startups, like helping them think through, you know, take getting my product management hat. And I really enjoyed working with early stage companies, just thinking about, you know, how do you think about your strategy, how do you think about early commercialization, etc. And in the process, I kind of stumbled with a couple of VC internships. Like so, my path into VC was mainly through a bunch of internships, and I really enjoyed the thousand feet overview of landscape that you get sitting in the VC ecosystem, also your ability to roll out, roll up your sleeves and you know help out early stage companies. At the same time, like you're part of like, you know, the investing muscle is a relatively new one. I didn't get into VC because of like, you know, hey, I wanted to invest in startups. It was mainly out of a curiosity to work with early stage companies. And one thing led to another, and I joined NGP Capital, which is an early growth fund focused on series B's and beyond. Did a bunch of investments, including Coda, which is you know, got acquired by Grammili and Immuta, which is in the data governance space, and a bunch of others. And at the same time, wanted to go earlier and earlier and uh decided to join the Hitachi Ventures team, which is more focused on seed and series A's, again, investing in early stage companies that have you know more of a software flavor to it. I think we're all questioning what software means, especially with this whole code gen and likes. But at the same time, I do feel that we are at a unique point in time where the entire interface of software and how we of how humans interact with software is gonna shift dramatically, right? So that continues to excite me from an investing lens standpoint, and yeah, that's uh just about my background. Um, that's awesome.

SPEAKER_04 11:24

That's wonderful. I think that's the best best introduction we've had yet. Okay, thank you.

SPEAKER_06 11:31

Yeah, um, and so and so you said you worked so you worked both with startups and then internships with VCs?

SPEAKER_05 11:40

VCs?

SPEAKER_06 11:40

Yeah, I mean, maybe maybe I can ask what was different about those two experiences, right? Like I guess the VC, you're looking at it more from a due diligence perspective versus startup, you're actually working on whatever problem you're you're wanting to solve, something like that.

SPEAKER_03 11:55

Yeah, something of that. Like, I mean, uh again, with startups, it's more of like, hey, this is an operational challenge that you need to address. Like it and and largely, again, in my capacity, I was mainly like helping think through positioning, right? Like, you know, how do you kind of think about positioning, right? But at the same time, on the VC side, of course, I think uh maybe a funny story to share here. So the first like VC conversation that I had, like I had no idea what this whole field was about. I just showed up. And one thing I learned early in my career, when you show up to these unstructured, you don't know what to expect, type of uh work situations. It's nice to kind of come with a, you know, come with your own structure so that you can control the narrative, control the conversation in some shape or the other. So I did this entire like a mini deep dive into this enterprise chatbot space. This was back in 2019, 2017, 2018 time frame where chatbots were a big thing. And this was incidentally with a VC fund in New York that had all the finance muscle of how to think about investments, but they didn't have the technical muscle of how do you kind of assess technology, right? Like, you know, or what's good. So I kind of went with my own flavor of hey, this is how you kind of you should be thinking about it from a technical standpoint, and then try to marry it from a you know high-level strategy. And I think that kind of impressed the folks on the other side, like you know, and that's how I I mean basically I was right.

SPEAKER_04 13:21

I'm bet you I'm betting a lot of them couldn't do it, they didn't understand the technical aspect.

SPEAKER_03 13:25

That's the that's that's what I recognize. I mean, again, I got lucky there. I don't know uh if there was any science to it, but I just recognized, you know, recognized the audience in the room, and I know that these people were, you know, investment bankers. And again, this was because I was in New York City and I had the proximity of you know dealing. I I knew that these investment bankers essentially didn't, uh or consulting background folks didn't have the muscle to be able to understand, hey, this open source technology could disrupt XYZ or whatever, right? Like, you know, so just use that, because I this was something which I knew intimately well, so I just used that, you know, unique whatever uh value add I could bring to the table to land an internship. Like so great.

SPEAKER_04 14:05

So I have a question. So now that you're Hitachi Ventures, I mean you you were more growth stage, and now I think you said you're you're pre seed or seed to series A. So anyway, earlier stage, especially when you're at like the seed and pre-seed stages, how do you find these companies? Like, do you just kind of ask them by net or do you have to go and look in specific spots? Like I I don't want to leave your answer, but how do you do that? How do you find these duals?

SPEAKER_03 14:37

Yeah, so I'm gonna share my, I mean, firstly, like just some macro background in terms of when I started in VC, right? So, firstly, I started in the 2020 timeframe. And between 2020 and 2026, the last six years, actually the VC landscape has gone through a tremendous shift in many different directions. This wasn't, I mean, the pace at which things have shifted in the last six years is much more than what happened in the last, you know, in the 2010 to 2020 decade or you know, even before. So let me kind of elaborate what I mean by that. Firstly, I think in the 2021 time frame, because of COVID-accelerated digital transformation, there was a tremendous amount of capital that flew into or came into the VC space. So just to kind of give you it almost increased 5x in the between 2020 and 2021. And we saw a lot of crazy deal making. I was see seeing this, you know, firsthand, I could feel this, you know, in my first two years of VC. Like, you know, there's so much deal making that uh traditionally you as an investor, you kind of take time, you know, you do your due diligence, you know what you're getting into, but that wasn't the case where the whole Tiger Global uh led uh you know deal making pace, right? So that was one big change. And then of course in 2023, 20 early 2024, there was the big, you know, Chat GPT uh and the whole AI landscape kind of shifted, and you know, now we are in the midst of an AI revolution. So I think these were two different macro incidents that happened even in my short span of six years or you know, in VC, which have kind of played a tremendous role in terms of how I have been personally experiencing and thinking about investing as such. So, Rob, to your question about how do you find early stage companies. Initially, when I started out, I think it was a general knowledge or general attempt, at least if you're at a slightly growth stage, but I would say series B's, you did took a very thematic approach or a thesis-driven approach. So you studied the landscape, you went and met every different companies, developed a sense of what a good, better, best looked like, and then kind of you know invested in one, right? That was the initial, and I still continue to you know uh do thesis building and you know, but also the tech has become so fluid, like you know, even in within if you just take the AI landscape, like things are shifting so quickly that it almost becomes a huge challenge to think about uh you know, what will you build if you build a thesis today? It is going to get outdated within the next month or two, right? Like, you know, so what does this mean? So I think uh myself and the broader industry as a whole has kind of shifted to a very, very network-driven. Like, you know, let's find the best founders, best you know, talent very, very early on in the cycle. Invest in a relationship. So I typically invest in CD and CDZs, so I do want to kind of have some head start in terms of you know relationship building. But at the same time, like I do know of uh plenty of other funds who just kind of you know invest just in the talent. Like if they just see uh X OpenAI or X-anthropic, they're okay to kind of write checks, right? So I think it's become very, very network-driven. I think every VC fund out there is soaking in sourcing and soaking, I mean, like soaking in, you know, or rather not soaking in, but rather want to kind of source aggressively. And again, I think what has this actually reminds me of Charlie Munger's one of axioms, Charlie Munger, that the job of an entrepreneur is to weave a web of seamless, well-deserved trust, right? So similarly, for a job of a VC is kind of become, you know, you have to weave uh weave your own web of well-deserved trust, and then your natural deal exchanges starts happening from that. Okay, so that's what's you know, that's to your question. How do you find like I'm trying to weave my own web of trust, which includes working with you know high-quality founders, working with you know industry leaders and working with you know folks generally within my network and trying to place them in interesting companies, which I think are rocket ships, and that I'm hoping would create like a seamless web of trust, which in turn you know be turns into a sourcing funnel in some ways.

SPEAKER_04 19:00

Yes. Okay. Well, I'm gonna I'm gonna give you a minute to speak, Trevor, because like usually I'm not short of speaking, but I'm a little normal today, given my uh Divi.

SPEAKER_06 19:12

We've we've talked about the concept of the uh the speaking stick. And so you you pass the speaking stick over, and then it's it's a little harder virtually.

SPEAKER_05 19:21

Yeah.

SPEAKER_06 19:23

No, that's really, really interesting, you know. So I I think I think I love the concept of sort of this of this growing ecosystem, you know, and I think that's actually something that we struggle with in Canada, is we end up losing for one or more reasons. Usually the reasons are fairly straightforward. There's more money money in Silicon Valley. If you're raising above a certain amount, you're gonna need to go down there. And so we do have a lot, a bit of a one-way ticket of companies that start up here that raise up to a certain amount and then that go down to Silicon Valley or New York or Boston or you know, one of the hubs and continue to sort of raise funds. And I mean, like to to the extent that my my startup was in New York this past week and just we just participated in the pitch last night. So you know, so so what do you do have any recommendations when it comes to you know trying to encourage people to stay, let's say, in Canada, uh, you know, despite the the I don't know if it's challenges or opportunity, just despite other opportunities that exist elsewhere. And you know, to to to sort of try and offset that brain drain that that we are subject to.

SPEAKER_03 20:50

So if I've understood your question correctly, so what are some ways to kind of keep the startup in Canada, but at the same time, you know, c continue executing, or what are some Yes, yes.

SPEAKER_06 21:03

Like we still we we still want to, I mean there's a bunch of questions in here that I could ask, you know, but I think I I think the the the two that I think about the most are are are sort of people and talent and you know and and and and sort of growing the ecosystem. You know, I think I think I think there are there are a shall there's a small list of unicorns that have formed and stayed in Canada, right? Uh Shopify is is one that pops to mind, right? There's a few others, well simple, I think. Um you know uh there's a few small ones that are not small.

SPEAKER_03 21:44

Cohere for that cohere for that matter, coherence.

SPEAKER_06 21:47

Yes, no, absolutely. And so and so there are but you know, but we we're we're what's the way to say it? We're punching below our weight class. You know, we we have we could have A bigger infrastructure. You know, we we we could have a bigger economic infrastructure here for startups specifically. We could be sub there's certainly lots of things we could be doing. We could be supporting startups more, we could be supporting startup founders more, but but the the the one thing you know that people keep referring to, you know, and I I don't know if I've heard it so much from from the policymakers, but certainly, certainly from, you know, I mean, even Rob, right? Uh Tech To. We had a we had a tech, there's a there's a Toronto-based tech scene, and and there's a there's a sort of non-profit company called Tech Tio that runs like a monthly event, has been running it for about 10 years now. That's just a get-together of of different people. And and one of the recent ones was you know, getting your company prepared for Y Combinator. And there was a big there was a big controversy that came up where they said they were they would not accept any more, they they wouldn't accept companies that were incorporated in uh outside, you know, outside of the US, yeah.

SPEAKER_04 23:11

Yeah, this was Gary Tan, right? Who's the CEO? Yes, who incidentally, as you may know, Dibby, is actually a Canadian, so frankly, she's I did not know that.

SPEAKER_02 23:19

Okay, okay. Okay, okay, okay.

SPEAKER_06 23:22

So, so and and so it caused it caused sort of a you know a small tempest within the teapot here of like, oh my god, you know, and and and and then to the point where they actually uh went back on it and they took they uh rescinded whatever the the thing was, but it's still the case that you know that that we do end up losing a lot of comp companies south of the border, and that hurts for two reasons. One is that you know, of course, that revenue goes away, but more importantly, the the those talented you know serial founders, right, sort of also leave. And I think I think that's what we lack in Canada, at least outside of maybe fintech, not as much, because there's more fintech companies up here, because at least in Toronto, because it's financial capital. But but you know, like there there there there is a gap. There's there's there's a definite gap. And you know, what are your thoughts as to maybe some ways of of combating that?

SPEAKER_03 24:23

Sure. So let me share my perspective, and again, I want to caveat saying that I have lived uh uh you know and worked primarily in the US, so you know, so and but I've also kind of lived in a few different places to be able to observe the differences. And so I've lived in the valley and I've also lived in New York City and Boston, right? And even within these three places, which you know, to a certain extent there is startup concentration in all of these different places, I I feel like the Silicon Valley ecosystem is almost 10 to 20x you know on steroids than you know what New York or Boston is, right? And I used to joke that it is Silicon Alley in New York versus Silicon Valley, right? And and that's not and then that's not a dig on you know the tech capabilities of New York or Boston, or Canada for that matter, right? Right. I think where I mean, I'm sure you know this, but there is a network effect that kind of sits here in the valley, which is almost impossible to replicate anywhere else. And it's the same in some ways that Wall Street, you see this network effect of people, you know, bankers chatting in a bar and you know, talking about deals and talking about pricing, etc. The same thing happens here in the valley where people are talking about code or what's the next best thing. And it's not a you know one-to-one comparison on the quality of the technology in any shape or form, it's just that that natural ecosystem of sharing and you know, knowledge sharing that and people kind of willing to participate in that ecosystem development that's very hard to replicate anywhere outside the valley. And if someone is able to replicate that, that's good. Like, but that's kind of becomes organically here in the valley, and and it's just probably a function of how things are set up here, right?

SPEAKER_05 26:13

Like you know, right.

SPEAKER_03 26:14

So I think what does this mean for startups who are emerging out of Canada? I think there are two things here. One is you have to kind of separate out fundraising from startup building, right? I think you can't conflate the two together. And I've seen this in plenty of cross-border founders who've done this successfully, say coming out of the Indian ecosystem, India cross India US cross-border or Israel US cross-border, which is like, you know, and then you know, even with some Canadian startups. I think for the management team, at least in the early days, it's recommended that you stay close to the geo for which you're uh the market that you're building the market, you know, product for, right? So building first. So that's certainly there. But then from a fundraising standpoint, I've also seen founders kind of you know decouple the startup building. They can go build the startup anywhere, whether it's in Canada, whether it's in uh you know India or Israel or so. But you know, from a fundraising standpoint, I think it just makes a lot of sense to kind of be participate in this valley ecosystem, just because these connections, this the fundraising tends to kind of work in a little bit of a warm introduction, organic way. Of course, your VC, early VCs can help you and people can intro, but you know, but for someone as an outsider to kind of get started with the fundraising, you have to kind of spend time in this ecosystem and you know get to know people. And that's where like the giving aspect of Silicon Valley starts playing into, you know, coming into play, where people are very uh forthcoming in terms of introductions, etc. etc. So I think as a general you know lens of viewing Canadian companies as a VC, I don't think I would hold it against them that they're geographically in Canada, hence I wouldn't invest. Actually, it's a geographical advantage that you're not in the valley, especially from a you know valuation perspective, entry price, et cetera, et cetera. Still look for the fundamentals, which is how is the founder in terms of you know how he or she is thinking about you know the product, the go-to-market lens, and how how you know astute they are in terms of being able to navigate the uncertainties. That's of course, and then of course, uh you know, given the type of companies that I invest in, I always look for deeply technical talent that you know how and how they're able to surround that. That can that's true whether you're from Stanford or whether you're from you know uh the Canadian Waterloo ecosystem, like you know, so but and of course, there's the early commercialization, how are they like you know, how what are customers thinking about so though those fundamentals remain the same and it's not uh influenced by you know the geographical location of the startup. But there's another element which I do evaluate in founders, which is like their ability to go fundraise because I don't want to be the only VC who's funding them because I'm constrained in terms of you know how much capital I can deploy. So, what is the fundraising? And that's a skill that you can kind of develop by staying in this valley ecosystem, you know, along and you kind of pick it up, like you know, yeah.

SPEAKER_04 29:11

Is it a matter of just doing a lot more pitches primarily to learn that sort of skill, you think, as an entrepreneur, as a founder?

SPEAKER_03 29:19

So it's not just about pitching, there's a lot that goes behind that. Like, you know, you need to be able to kind of read the room, manage timelines because each VC is working with their own timelines. I have, you know, as much as I would like to give white glove service to each and every founder that I'm uh you know I'm interested in moving forward. But at the same time, you know, given the volume of startups that have kind of exploded, it's it's you know, there are 10 other companies in my pipeline itself. So then it kind of from a founder's perspective, they need to know how to kind of run a process that is it's a skill that you learn along. So syndicate construction and fundraising is a very intense, you know, game of poker, if I may say, both on the VC and more importantly on the founder's side. Like I do empathize how hard it is, but you know, this is a game that you have to learn at the end of the day.

SPEAKER_06 30:09

Yes, yes, yes, yes. Yeah. Yeah, interesting, interesting. Yeah, no, I I think that's that's actually quite helpful. I think that the one thing I took away from that is that learning how to fundraise, right? Is a critical skill that doesn't require geography, but that does require kind of and and and so you know it yeah, it it requires you learning the language, essentially, right?

SPEAKER_03 30:42

So and and how do you learn the language? So that's where I'm my uh my advice of you know spending time in the Valley Cosmo because you just organically bump into other founders who and one thing I've observed as on the founder side is there's there's an in in there's an unsaid brotherhood slash sisterhood where like everyone's supporting each other, like you know, so and and you learn this along the way, like you know.

SPEAKER_06 31:03

So no, no, yeah, I think I think definitely there's there's a you know a look of knowledge, you know, when you're speaking with other founders in terms of okay, you've you've been through the you've been through this and you learn that, yeah, yeah.

SPEAKER_00 31:19

And and and a shared sympathy, yeah, shared sympathy, like I can also deserve some sympathy, but I'm sure you know sympathy for the for the founder and for their spouses, they're very patient spouses.

SPEAKER_05 31:36

Exactly, exactly.

SPEAKER_06 31:38

When they are married, yeah.

SPEAKER_04 31:40

Uh yeah. So Divya, what like would would this week that you just perhaps completed largely, if not fully, would would this week be a typical sort of week for you? Can you explain what a sort of typical week might be for someone like you? That's a good question. So is it always changing?

SPEAKER_03 32:00

It is changing, it's very cyclical, I would say. So I would say if I kind of just break down the three key or rather four key tasks that I have to kind of juggle, right? Like, you know, so one is of course sourcing, which is trying to find interesting companies, and tied to it is also what we call as thesis building, so having some view of where where to look for, where to hunt, etc. Sometimes it can be you know very intense in terms of thesis building where you're talking to folks, you're trying to gather insights. I think like VCs in some ways uh is a is uh you're shepherding insights, right? Like, you know, so that's so you have to kind of you put yourself out there, let people know that you're thinking within my own circle about what areas I'm hunting, and get, you know, hey, have you seen this? So I think sourcing and thesis building is kind of what two key aspects. Uh the third big aspect is okay, you've sourced, you've met like company meetings, is uh uh I at least meet like at least seven companies per uh per week, like you know, if not more. So I think evaluating those pictures and trying to see which of these makes sense to go to the next level, etc. So that that continues to happen regardless of the various phases. And the third phase I would say is the in the rabbit hole. So I like something, I sense a deal, I want to kind of build that conviction, and then kind of you know, so that's the you know, deal rabbit hole where there's a lot of different elements associated with it. One is, of course, once I like something, I'm kind of trying to kind of build a relationship with founder and try to see is this beyond liking a product or a market that they're building, like is this a founder that I can work with? So there's a lot of work that goes into that relationship building. Then there is the bigger piece here of you know, investment case. So where I have to kind of convince my team why this is a good company to go after, right? Like, you know, so there's a a lot of work that goes to the investment building case. And I think the part which isn't spoken, and that's just this goes to my comment of VCs deserve sympathy as well, is the winning phase, like you know, where of course, if it's a founder that you know you like, there's and and and the the market, the capital markets and the VC market is incredibly efficient. So I'm sure if I'm chasing the founder, there are other 10 other VCs who are chasing the founder as well. You know, so this is where the winning aspect kind of like the deal making aspect kind of comes into play, like you know, so where it's not just enough that I give a term sheet or I ask for a certain allocation. Uh, it's also important that I get what I ask for. Like, and and that's where like founders, as you're constructing around, like you know, you I sympathize that uh there's a tremendous amount of pressure in terms of managing that syndicate. You have to cut people down, like hey, someone asked for like seven million allocation, but you have to bring them down to two, and I need to on the other end be willing to kind of take that tool, like whereas I first pitched you for a seven and whatever, like you know, so there's a lot of song and dance that happens and as part of the deal making, which also takes up a significant amount of time, right? Like, and then that's where you know this is the competitor sport aspect of VC kind of comes into play. You have to kind of use every tool in your arsenal to kind of go get what you want in some ways, once you've made up your mind that you like something, like like a company, yes, like it, right? Like, you know, and then of course, like you know, there's a big part of which is also portfolio management. It's it's like a flywheel in some ways, right? So, okay, I've invested in the company, I can't leave them. You know, of course, you know, the best founders and companies, of course, you know, there's a lot of fires that you deal with, and you know, one part of you know, founder evaluation is how much of a fire can this person or the founding team handle on their own versus when you require outside intervention. But the best best VCs always uh serve as a sounding board. So, you know, whether it's uh a key talent hiring or some you know uh uh you know, next fundraising, how do you kind of tackle, you know, prepare your data room, et cetera, for your next round, or some positioning and you know, some recent product developments, and they want to help you think through some and and I will you know think through positioning or any some go-to-market uh this thing. So I think, and and of course, like there's also the implicit value add. I'm always looking out for my portfolio companies in terms of you know how I can help them, whether it's in my own capacity or by connecting them with the best folks that I know within my network who can be helpful to them. So that's the portfolio management aspect. So I think to Rob to your question, like every week kind of requires, you know 80% or rather 70% of one aspect of these different things that I described, like and the rest 30% is dedicated split between the rest of the you know, pie. So yeah, so every week is different, like you know, so it greatly depends. So at least this this last week.

SPEAKER_06 36:45

I guess it depends where in the cycle you're at.

SPEAKER_03 36:47

Where in the cycle you are, where in the cycle you are, yes.

SPEAKER_04 36:50

Yeah, and I was I was glad to meet you in Toronto. I'm glad that you're coming up for things like that. You I mean, clearly you you know about the Vector Institute, which is like a co-founded by Jeffrey Hinton, and people like that. So this is one of the premier, I think, AI institutes in the world. And yeah, but it's nice to have people like you recognize that and coming up here. And I dare say that it won't be too, too long before the administration south of the border changes such that we can all be friends again.

SPEAKER_01 37:21

I'm not gonna comment, yeah. I'm like you mentioned the outside of the outset of the podcast that you would edit stuff like the point that I'm trying to make is that we want to come closer together, right?

SPEAKER_04 37:35

Yeah, and so I I I'm happy that these sorts of things happen.

SPEAKER_06 37:40

Well, and and and there's still there's still a lot going on. Yeah, I think I think there's politics can only inject itself so much. And uh, exactly.

SPEAKER_03 37:49

I mean in yeah, you know, the again markets are incredibly efficient, like you know, so if and innovation, if like wherever it is, like if the dollars are gonna flow, dollars or you know, US or Canadian dollars is gonna flow, like in the stuff.

SPEAKER_04 38:02

Yes, of flows and and and the where and to whom to where you know you're you're from India originally. What about India? Because I know when we were talking about Canada before, it's like, oh, Canada experienced a brain drain, but of course we're not the only ones, we just happen to be your neighbors or one of your neighbors, but I think of India too, and there's so much talent there. Yeah, um, like can you tell us a little bit about what you think about India right now and Indian entrepreneurs in particular? Like, and and are there cases that you know of where maybe some Indian founders go to the US, they build maybe even they start building a company there, but they go back to India. Does that happen much? Have you seen that?

SPEAKER_03 38:47

A few instances. I think firstly, like I just want to acknowledge again, speaking of the administration or so, like you know, there so the way I came to the country was through a F1 visa, which is a student visa, and then I converted into what is called the H1B visa, which is the highly skilled worker visa, right? And as having gone through the rite of passage of H1B and the whole uh permanent residency process, etc. etc., I can I can certainly empathize the long waiting queues for H1B, which can kind of inhibit a lot of entrepreneurial dreams, right? Like, you know, so because your your H1 requires you to be sponsored by a stable, a stable employer, right? Like, and but of course, there are hacks these days to kind of uh you know get past that. If you really want to start something, like you know, you can always switch visa status, etc. But it is a huge you know risk that a lot of uh you know folks from India are taking, or rather on standby not taking the risk as well, like because of this you know visa issues. I think what we are going through right now is a little bit of the cleanup of the H1V system. There's a lot of repercussions that we're seeing right now, and I'm hoping that it would start settling soon and it'll continue to kind of you know revert back to the original intent of why this whole visa was created, which is to kind of attract the best of the talent from outside of the world, right?

SPEAKER_06 40:05

Yes, yes. I mean, like there there definitely are companies that are abusing the H1B system. Exactly, exactly. And there can be reforms made to it, and hopefully these reforms are on the right path towards you know getting back there. Yeah. I mean, uh there's a there's a Canadian skilled workers process as well, and um fraught with many of the same problems, you know, like you have to the company has to be around for a certain number of years before it can sponsor people, and and and and there's other rules. And so we're actually tackling this ourselves with our own employees and co-founders who are students who are on a student visa. And you know, so it's it's that's certainly not not not not just a can not just a US problem, not just a US thing problem. Yeah, it's it's it's a it's an everywhere problem, absolutely.

SPEAKER_04 40:57

And Canada grew Canada grew particularly quickly, particularly even during COVID and after COVID, because like we had a labor shortage in many of these industries. And unfortunately, the government, I don't know, through their wisdom or lack thereof, or just like it's just too hard a problem when you're bringing in people suddenly, but you don't plan to, or are not capable of building infrastructure around that, like housing for people, or you know, upgrading your your healthcare system, and then suddenly people you know cannot get a family doctor or any kind of service. And you know, one of the negative effects of you know not building that infrastructure to support new people coming in, so many people coming in the country that it's turned a country that until like maybe six or seven years ago was super pro, like pretty much everybody was pro-immigrant, and now you've got these really vociferous kind of people who are like frankly, it's it's very unfortunate. I uh and you know, you've got a rise of racism, I think here. You may see that in the US, a lot of countries, right? It's just I I I hope that we I think we are turning the corner on that, so those people can just kind of mean the negative voices, like shut up and and we'll deal with it. But like, you know, it's affected cities like Toronto, for example, as you may know well, having been here, very expensive. I was in Sydney last week, and it's even more expensive in Sydney, for goodness sake. And yeah, I think it is symptomatic of globalization in general. It's you know, like you said, the efficiency of capital will go, you know, whether those are individual retail flows of money and people investing their own money, or it's um, you know, people like yourself at venture capital P firms or Wall Street firms, that's gonna happen. But we need to sort of figure this out because otherwise it's kind of gonna rip away a lot of the great things that I think globalization has brought. The silver lining I see in a lot of the tumult, if you will, nowadays that's been happening is that I think you're you're gonna get some strengthening of alliances, like you'll look even from a defense standpoint, like NATO. NATO I think will be better for this in the next five or ten years, notwithstanding the government du jour, wherever.

SPEAKER_06 43:23

And I think just in terms of countries moving together, like I was gonna say, Europe, like well, Europe and Canada are talking about like extending cooperation and extending alliances, and that's that's relatively new, you know, and and there are other interesting things that have emerged as well. I think the one thought I had when it relates to this kind of stuff is just the silent majority. You know, I think we've talked about this before, Rob, right? There there is a silent majority of people that don't think immigrant immigration is bad that. think that and right and and and if you I mean I I was again there in the states and I am a US citizen and you're an immigrant you know I'm I'm a double immigrant so I'm I'm originally South African moved to Buffalo New York and then went to MIT and then came up to Toronto and and now I'm dual US Canadian citizen and you know it just I mean I was I was talking about this with friends this week or new friends that I just met and you know there's a lot more so there there's there's of course there's a vocal minority of anti-immigrant people that are supporting the Trump account very and but there is a much larger silent majority of people who are sons of immigrants and daughters of immigrants and immigrants themselves and you know it's not outside of the realm of possibility to say hey you know everyone who supports immigration why don't we get together and form our own political party or whatever it is and say we're enough of this enough of you know enough of these billionaires that are lay laying the blame of everything wrong with society on those poor hardworking immigrants that are actually helping this country you know like there's there anyway sorry it's it's it's it's a it's a bit of a it's a bit of a soapbox yeah well I didn't think we can solve for it in this opinion it's a bit of a soapbox but I think I think it it I think it raises it raises the point that maybe maybe we need to not be the not as silent majority. You know maybe we need to say that there is a good thing. I mean my my mom when she like so so again my family emigrated when I think when my dad was 40 uh when in 1990 and you know so so like I I have all of the respect in the world for for my parents you know picking up everything leaving everything they they knew coming to a new country starting over with like you know 13 and 10 year old kid and and and and I think it's you know as difficult a process as that was it it gives you a perspective on the country that you live in that's different from other people and it gives you you know and and and I mean like there's there's a reason right there's there's there's also a reason that many of the entrepreneurs that we know are immigrants because it's it's the same sort of thing. You're starting over you're starting new you have to kind of assemble together your own support system and your own thing and and and and you know like actually emigrating is something that that gives you at least the if not the skills then at least the the the knowledge that you can do it right the knowledge that you can do it.

SPEAKER_04 46:59

Trevor a a couple of things one is I think it's kind of like sink or swim right so you suddenly face with this and you learn through that and you succeed kind of one way or another you muddle through because you have to but secondly anybody who's willing to go to another country for a long time and I even would count to a lesser extent than you two myself like I went off and not knowing much about Anna I lived in Tokyo for five years but anybody who certainly goes and immigrates to a country I think it selects for a certain kind of person in many cases. That's a kind of a big risk unless like you're fleeing warrior a refugee from that then like you're just trying to survive but yeah but but but you've you've you've done enough to say I want to get out of here and you've made that happen as well.

SPEAKER_06 47:53

You know so yeah yeah yeah absolutely and and I mean like I I I was heartened by the number of Ukrainian refugees that have started companies you know like I saw a bunch of them last week like there's there's two that are and what one of them's a good friend of mine because he's he's a stand up comedian as well as a pod as well as a you know startup founder and and I am too very very very amateur nothing no none of my none of my sets are sort of worthy enough of putting out there but but you know like it's Oleg and and and he he's amazingly positive for all of the stuff he's been through you know and and just he's built putting together a company that helps other companies to to grow and and set up and establish.

SPEAKER_04 48:43

So I'm I'm I'm so I don't have any real connection to Ukraine but I support them and it seems a bit weird to say this it's like a couple of days ago when I met this young woman I was telling like I'm super impressed like like super confident but just in general about like Ukrainians I'm I'm proud of them for standing up to like such a huge military and they're all in but I have a just as you mentioned it now last week when I was in Sydney because we all throw so the company I work for as you think you know it's it's a global growth advisory it's based out of Australia. So we all had our our offsite a lot of us kind of flew in from around the world to Sydney and that was a bucket list thing for me I'd never been to Australia so I was super happy about it. But the most amazing thing about that trip is that that I guess he's the he's the managing director for AMIA for us he's based in London Rob Jeffries and his like it's for someone coming like from Toronto for example or people came in from uh elsewhere in the US and all over the globe it's a long journey as you know but for Rob it was particularly long and he had just he came in via Ukraine and um it was a very long convoluted journey for him but he had spent two weeks there supporting his his girlfriend slash wife so I just think that's amazing and in fact they auto he was walking around and they basically automatically tried to conscript him into the army and so they like they I think they put him on on the on the truck and everything and luckily he was able to get out of it because he happened to be able to find his British passport but otherwise going like they were going to the front lines and like that's amazing like someone do that right this is what love will do you know leave there yeah that's that's insane yeah I was and then he's like how are you doing and he started telling us a story I'm like what yeah yeah yeah yeah it I don't know when you when you start asking people how their day is you should be prepared sometimes to find out wow it's it's not small talk all time right yes yes sometimes features for a download yeah yeah so so you know thank you so much for coming on our podcast divia this is really terrific and you know hopefully we can all meet up in your neck but you're in Palo Alto right so yes maybe we can go there we actually we speaking of going there so we just recently a guy I met last week again his name is I gotta get this right I've forgotten most of my Japanese uh for the Japanese in the onda in the audience anyway so Mitsu Ishigo san is our new partner for Japan because that's a big market for us but of course if you're at uh Tachi Ventures with the mothership being there so we might be in your neck of the woods soon so we'll maybe drop by and say hello but thank you so much for coming on our podcast this is an honor to have someone like you on here and I'm glad you guys didn't take the whole time and just like try to unsuccessfully it would be but to try and make me feel small because you know having two MIT years gang up on me which I which has happened before but you should go back and maybe and listen to one of our podcasts with our friend Nadine Miller who's fantastic and not only is she an MIT alum she's also U of T engineer and Oxford MBA.

SPEAKER_06 52:22

So and she's done fabulously well and she is we'll introduce you to her at some point because after I guess you know doing very well in my as a mining executive she's now how what would you term it Trevor and and and what's the name can we say the name of that even did she say yeah yeah it's Nanny Gill yeah no yeah so she's she's building a new she's started she's on a couple boards of mining companies um she had an article written about her the Empress of Mining which is a lot of fun to read she bought it she bought a Tierra a real Tierra with actual real Tierra with diamond I'm gonna look this up right after we hang up here.

SPEAKER_03 53:03

She's great and and but she started a company that's really grown out of an experience she had which is that her her father and her her partner's father are getting old and need uh support and so she's built this sort of smart house system that can keep keep keep her informed as to you know like that that everything's okay with with her dad or she has the ability to kind of check in on him when she's when he's living at home but like with her but she's traveling the world so yeah very interesting and definitely there's a lot going on in the whole aging tech yeah it's it's only yeah it's only gonna get bigger right there's there's it's only going to get bigger yeah there's uh I'm sure the MIT actually has a lab called the aging lab uh the aging and there's a yeah it's called the aging economy that's the book written by the so it's just interesting to see yes um all the research being done into different aspects of aging yes yes didn't they didn't they used am I getting this wrong didn't they used to call that gerontology or is gerontology not aging it's like you've already aged and then they're trying to it could be it sounds sounds vaguely familiar but yeah yeah okay yeah change anyway thank you thank you for having me Rob and Trevor uh it was great to kind of convert a serendipitous interaction with you Rob uh into an interesting podcast so I look forward to you know staying in touch and of course yeah do let me know if you're in the you know Palo Alto area or if I'm in Toronto.

SPEAKER_04 54:36

Please come back to Canada we we want more people yes absolutely I'm just waiting for the weather to you know get better right now no you would love to know I know it is yeah I'm sure I'm sure because even the even just a few weeks back when I was there like I I forgot that I'm from I mean coming from California I forgot my jacket that was increasingly yeah but before we go I gotta say you know like I I was on I was in Sunnyvale some years ago maybe this is six years ago um just before the pandemic and I was working for fintech at the time and we were we got into the plug and play tech center right so I was on the rooftop of the plug and play tech center there in Sunnyvale and I was meeting with a very important corporate VC and I had stupidly I just come I think it was like late February maybe early March and it it was cold in Toronto like it was definitely like freezing and but I just brought a a light jacket and I thought that would be sufficient and it's not like I hadn't been there in that neck of the woods before I had but I'm talking to this guy a very important conversation and I am not kidding I could not I was like almost violently shaking for the whole half hour and at the end I was saying I wonder if you notice I'm like so I thought oh I should apologize I apologize for like you know I've been shivering is like yeah I noticed you the whole time was like oh my god but that just makes you more human I guess right yeah yeah yeah I mean I think the the one thing which I at least I don't know about Toronto evening summer evenings but uh the one thing that I miss about Boston and New York for that matter is the warm summer evenings.

SPEAKER_06 56:16

Oh yeah in the Bay area it can get like very hot during the day and then like very cold in the night cold at night yeah yeah yeah we have the the coldest winter I ever spent was the summer in San Francisco.

SPEAKER_04 56:31

There was somebody told me it's an Oscar Wilde court but it's not an Oscar Wilde court but no no it's it's um it's it's uh Mark Twain Mark Twain Mark Twain okay oh is it I don't know if he's been okay I I okay never mind you might be right all right cool okay well on thank you and you know thank you to all our I like to say the hordes of Hayoc pain friends listener um temporally speaking you know time shifting here of course but our audience has been growing we've got uh a a several episode recordings that we've done recently and we've been busy so we have a little bit of a backlog so it might be a week or two before we get yours out divya but we'll let you know so again thank you and good night good day every good weekend