It can be scary telling people your goals, especially on the internet, but I’m throwing it out there because, hey, why not. You don’t know if you don’t ask. As someone who is a big fan of the startup scene and supporting entrepreneurs, I would love to one day be in a position to support them financially by becoming either a VC (Venture Capitalist) or Angel Investor.
Karen Swyszcz 0:00
You’re listening to The Bacon Bits ‘n’ Bytes Podcast, and I’m your host, Karen Swyszcz. This is the podcast where a bit of business and a byte of technology come together.
Hi everyone and welcome to another episode of The Bacon Bits ‘n’ Bytes Podcast and today I’m chatting with Nitya Rajendran. Nitya is a senior associate at Tribeca Venture Partners. She leads sourcing and diligence and serves as a board observer for ACV Auctions, Domio, Porter Road and Vivvi and prior to joining the firm Nitya was an investment banking analyst at Lazard where she received the André Meier Fellowship. She graduated magna cum laude from Georgetown University with a B.A. in Classics and a Minor in Economics. She serves on the Trinity Alumni Women’s Committee and as a board member for Off the Record, an organization that creates curated forums for founders. And in addition, actually, earlier this year, you were part of the list for the 2020 Venture Capital Journal 40 Rising Stars, congrats on that.
Nitya Rajendran 1:19
Karen Swyszcz 1:20
Yeah. So welcome to the show. And I’m curious to know, like, we could start a little bit with your background. So you grew up on the Upper West Side, and you’re gonna laugh at me because every time I hear like, Upper West Side, Upper East Side, I automatically think like Gossip Girl.
Nitya Rajendran 1:33
(laughs) I get that a lot. So.
Karen Swyszcz 1:37
That’s all I know. So I’m curious to know, like growing up at the upper west, on the Upper West Side of New York, what was that like?
Nitya Rajendran 1:43
Well, I can assure you that my life was nothing like what you saw and as a girl. So I’ll say that I loved growing up in New York in general. You know, I’m a die-hard New Yorker and, you know, there’s just so much diversity here.
You get exposure to so many different life experiences and so many different kinds of people and cultures. So I loved it specifically that my side was like an amazing place to grow up. It really has a neighbourhood, you almost feel like it’s a small town in a way. I went to school a mile away from my house. And so basically that one-mile stretch is where I like, did everything. So it almost had the vibe where like you would run into people, you know, on a random weekend at the movie theatre, and it was embarrassing or fun or whatever.
You know, like some of my favorite memories from growing up are going to the grocery store Fairway, which now might be closing, which is very sad. I remember going out with my dad every Sunday and it was I mean, I don’t know if you’ve ever been there Karen but like, if you go to the West Side before the Fairway closes you should go. That grocery store has so much energy and it’s always bustling. And like to me it just epitomizes all the although a kind of crazy, amazing energy that New York has to offer. So I just I love the Upper West Side.
Karen Swyszcz 3:01
Yeah, it’s actually been quite some time since I’ve been to New York. The last time I’ve gone was in 2011. That was my second time and I feel every time I go I don’t cover enough ground like you were saying there’s so many different neighborhoods and yeah, I think maybe I’m like overdue for a visit. I should go back.
Nitya Rajendran 3:19
Yeah, nine years is a long time. I feel like you should come back. We can like come up with like a hit list of like.
Karen Swyszcz 3:25
Like your recommendations. All right. So I always ask people about their their career backgrounds. And I want to know what made you decide to become a VC because I feel like it’s not something that you know, people talk like, or when you’re a kid, we say, what do you want to be when you grow up in the mean, I’m highly doubt or maybe you did you say like, I want to be VC or like, even like high school, when did that idea come about?
Nitya Rajendran 3:48
Yeah, it’s a great question. So I would say I really started very seriously considering venture as a career. when I was doing banking at Lazard. So you know about probably a year and a half into banking. I was thinking about what did I want to do next. I thought I had learned a ton of banking. And I wanted to keep learning. And I wanted to find something that I was really, truly passionate about.
So I was kind of thinking back on my experiences throughout life and I said, What am I really enjoying? What have I felt passionate about? And one thing I had done during my undergrad at Georgetown is there was a fund called The Social Innovation Public Service Fund. And that was a $1.5 billion fund out of Georgetown. And we would invest money into student entrepreneurs and alumni entrepreneurs and I’ve been the director of operations there. So it had been my role to basically vet these entrepreneurs and then actually work with them once we made an investment. And as I was thinking back, you know, that was one of the most rewarding things I had done up until that point in my life, like actually working so closely with these entrepreneurs, helping them build something helping them realize their dreams was so fulfilling.
So as I was thinking about where I wanted my career to go next, I was like, Okay, I needed to do something where I’m working with entrepreneurs. And I’m like actually moving the needle in some way. So that plus the financial skills that I gained, at Lazard sort of led me to venture which is a good marriage between that passion for entrepreneurship and finance. So that’s why I decided to get into venture and then actually getting into that was a whole other thing.
But that was what made me realize I really wanted to pursue venture.
Karen Swyszcz 5:25
I think that’s why a lot of people kind of want to get into that ecosystem is just this, you know, getting involved or like seeing everyone build cool things and really want to be a part of the like, helping support them and build build their dream. So I’m assuming like with any job like any start of your career, do you mind sharing it? You know, if you encountered any obstacles and how did you overcome them during the start of your career?
Nitya Rajendran 5:49
Yeah, absolutely. So, so basically decided I wanted to go into venture and I was like, Okay, cool. I’m a very, like, goal-oriented person. So I was like, once I decided this, how am I gonna go do it? So I did so much reading on the internet. I mean, the great thing is there are tons and tons of blog posts out there about how to get a job in ventures, generally, industry. So I did a lot of that work. And basically, every blog post I was finding was like, use your network, leverage your network, and I was like, I don’t have a network. I’m 23 years old. I, you know, I was working, you know, crazy hours, I didn’t have time to go to networking events. I was that to me was my first roadblock where I was like, hmm, I don’t know how I’m gonna get past this one.
So what I did was, instead of going to all the networking events, which I literally I could not do at my current job is I emailed a bunch of people in venture who had also gone to Georgetown, and I wrote like a very, you know, kind of short and sweet emails had my resume explain why I was really passionate about venture. And you know, about a third to a half of those people actually responded, and I was able to get coffees with them or talk to them on the phone and they were so helpful. They, you know, explained more to me about the tech ecosystem and the VC ecosystem. Some of them even sent me job postings. So that was, you know, really valuable for me. So I always do try to pay it forward now, because I know all those people really helped me. And but the end of the day, you know, I actually ended up I came up with like a list of my dream firms where I wanted to work and Tribeca was on that list. And luckily enough for me six months later, they published a job posting, so I ended up actually just applying through their website.
Karen Swyszcz 7:33
Cool. So it’s kind of like you, you manifested it, you just like wrote it down, and then all of a sudden, the job ends up popping up.
Nitya Rajendran 7:39
(laughs) I guess so.
Karen Swyszcz 7:44
What kind of skills would you say are needed to become a successful investment associate?
Nitya Rajendran 7:49
That’s a great question. You know, I will say it really depends on the kind of firm that you’re going to. So you know, if you’re a later stage versus an earlier stage firm, where the emphasis of your role will be different.
But I would say like high-level, the couple of things that will always be necessary are, I think, strong analytical skills. So are you able to assess, you know, the market opportunity for our company? Are you able to, you know, dive deep into the weeds of the way the company operates, but then also be able to take a step back and understand the bigger picture of things.
Are you able to communicate those thoughts specifically, like so much of a VC’s job is talking to their firm and like trying to, you know, make a case for why that’s a good company, but also being able to be flexible with your thoughts. So like, in our investment committee meetings when we’re arguing at deals like respectfully but you know, we all have really strong opinions, but you have to be able to like to roll, roll with the punches and be flexible and to internalize what people are saying and maybe, you know, change your opinion. That’s okay. And I think the really important one is founder empathy. So much of my job is talking to founders and working with them closely. And so being able to empathize with how hard it is to be a founder and all the, you know, things that they’re on their plate, especially in those early days when they don’t have a big team. I think founder empathy is really crucial.
Karen Swyszcz 9:15
Since we’re on the topic of founders, do you think they make good VCs? Because as we were talking about prior to recording this conversation, it seems like a lot of people who founded companies, they also end up investing in other companies as well.
Nitya Rajendran 9:30
Yeah, I mean, I think it’s like always tough to generalize. But I would say a high level I completely understand why a former entrepreneur would make a great venture capitalist.
I think, you know, going back to that point about founder empathy. No one will understand more what a founder’s going through than a former founder themselves. So you know, I think when you’re in a board meeting, and everyone is telling you, hey, you should really try to fix these like 12 things before our next board meeting in two months, that can be really tough versus maybe a former operator to say, Hey, I know we just gave you those 12 things here, are the real two like that you should actually prioritize. I think there can be more founder empathy there. But, you know, I honestly don’t have an operating background. And I don’t think I don’t necessarily think that not having operating experience is a bad thing either. But I can see why it would make you a good venture capitalist as well.
Karen Swyszcz 10:21
So there are different types of investment firms such as we’re talking about, like early-stage company, I’m sorry, investment firms that invest in early-stage companies, and then later stage companies as well. So if you were to start off on your like VC journey, like how would you decide as to which type of firm would be the best fit for you?
Nitya Rajendran 10:40
Yeah, that’s a great question. It’s something that I thought about a lot when I was trying to figure out, you know, what firm I would want to join. I would say it depends on a couple of things. One is like, honestly, what excites you the most, these companies have different levels like a seed-stage company, versus a Series D Stage Company. They’re all very different and working with them requires different things. They have different struggles and different needs.
But like, if you want to be a really, really early-stage investor, like typically, the teams are between, you know, three and twenty people. So there’s probably more heavy lifting for you to do. And like, that’s when the company is trying to figure out product-market fit. Or if they have a product-market fit, like, they still need to scale like crazy. And so there’s maybe more hands-on work. And that way, if you want to be a later stage investor, you know, hopefully by then the company is really rocking and rolling there. They’ve scaled already and like they just need help scale even more, but things are generally working. So at that point, you’re kind of optimizing. So it’s a different kind of work.
But then from the junior investor perspective, I think, you know, the emphasis of your responsibilities will be different too. So this is a huge generalization, but generally, you know, if you’re at an earlier stage firm, there tends to be more of an emphasis on sourcing. So trying to find tons of great startups for your firm to invest in, vs at a later stage investment firm you might be more focused on doing diligence for those companies. That also kind of depends on how you like to spend time. I love, where we invest, we do Series A deals, which is pretty early stage, but not like seed stage, which is super early. So things that companies have typically found product-market fit, but there’s still like a lot to do from our end. So it’s kind of a fun combination of sourcing intelligence.
Karen Swyszcz 12:22
So for myself, and I’m sure a lot of the other listeners are curious to know, what is the difference between Seed Stage Funding and Series A?
Nitya Rajendran 12:32
Yeah, it’s actually you know, even internally, we don’t really like to use these sort of like names for rounds, because I think it’s become so fluid and there are seeds, Seed Twos, Superseeds, so many things now. So I mean, I’ll say that since I joined Tribeca three years ago, I have seen these names change. So I would imagine I’m sure the ecosystem has really changed. I would say like high-level, a seed round like is maybe you built the product out, you’re just starting to get it to market like it’s very early days. But the threshold for a seed-stage deal has sort of shifted from like pre-product like probably having product. And in Series A where we like to invest high level is when a company has found product-market fit, things are working, and they just really need capital to scale like crazy. So that’s high level, how I think about the distinction between the two.
Karen Swyszcz 13:29
Okay, awesome. Thank you. So I’m sure given that New York has a huge startup community. And I’m sure that your investment firm, they get a lot of pitches. So how do you decide whether or not you feel a startup would be a good investment for your particular firm? Like, what kind of things do you look for?
Nitya Rajendran 13:49
Yeah, I think that’s a really important question. So there are two big things. The first is that there has to be a huge market opportunity. And the thing is, it has to be the right founder to tackle that. We won’t move forward with any company, if they don’t at least check those two boxes. So if you’re a founder and you walk into a VCs office, you should be prepared to explain why this is a massive market opportunity that you’re tackling, and what makes you the best person to tackle it? So those are kind of like the most important things that we think about. And then besides those two things, we like, you know, like I said, once the company has one product-market fit, and we’ll really dig around the data to understand, you know, if they have that conviction around those things.
Karen Swyszcz 14:35
And your current portfolio, do you have like a few startups that you’d like to talk about, like some startups that you feel are rising stars?
Nitya Rajendran 14:42
Yeah, sure. Um, well, having they’re all rising stars, I’ll talk about one is this company called ACV Options. It’s a mobile app for car dealers to facilitate wholesale vehicle options. This is not an industry that I actually do anything about before, but it’s one of those classic like antiquated industries that needed to be brought into the 21st century. So I guess the way whole, like used car sales, people would typically buy their inventories, they would go to a physical auction and not really be able to see the car they were purchasing. And they would do it. ACV auctions as they put all of this info into an app. So you can actually get all the information about the car. And then from your desk, you don’t even have to go anywhere. And this company has grown massively since we first invested in four years ago, and they recently were valued at $1.5 billion. So that’s been really exciting to be part of that journey.
Another company that I work closely with a company called Domio. They lease upscale buildings and floors of buildings as a long term tenant and then they monetize and operate them as short term rentals. So think about all of those, you know, AirBnBs, you’ve gone to they’re like, not what you expected them to be. Domio you basically provides a consistent like high end branded experience, but it’s able to operate much more efficiently than a hotel because it doesn’t have all the overhead. So we led their Series A in 2018 and GGV (Capital) just led their Series B this past summer. So another one. That’s very exciting.
Karen Swyszcz 16:14
That does sound exciting. So speaking of investments are continuing along the conversation, was there ever a time where you made an investment where you just went with your gut, you’re like, I know, this is going to be, you know, a really good investment.
Nitya Rajendran 16:29
You know, to some extent, I think there’s always a gut instinct when you like a founder and the company and it just clicks and you feel like this could be huge. You have to have that kind of excitement in your belly. But I never invest purely on gut. I think there has to be that good gut feeling for you to want to go forward and dive into the data but I do you know, I do always end up sort of diving into to more of the details there to corroborate how I’m feeling only at that point where I feel comfortable investing.
Karen Swyszcz 16:58
Mm-hmm. So with Tribeca, I understand that your company only invests in companies within the US. So I’m curious to know, do you know of any potential plans to expand outside of the US? I’m just thinking, because I’m based in Canada, and I’m relatively close to like Toronto, and Waterloo, and both of them are like huge tech startup communities.
Nitya Rajendran 17:19
Yeah, I think we’re open to it. Our main focus has always been on New York, like you said, the East Coast of the US more broadly, but we’re open to it.
Karen Swyszcz 17:27
Okay, cool. So I also know that one of your achievements was that recently you were a contributing author for the FinTech chapter and the newly released book called Finding Genius. Can you explain to us number one, what is the book in general that and also what is your chapter about?
Nitya Rajendran 17:44
Absolutely. So the book is a very interesting idea. Another investor in the ecosystem Kunal Mehta. It was his idea, and he’s going to kind of put the book together. But basically the promise of it is that the first half of the book is he interviewed a bunch of really prominent venture capitalists and thought their advice around what do they think makes a great offer? How do you succeed in this business? So he collected all that and put them into these really great chapters in the first half of the book. And then in the second half of the book, he basically asked a bunch of his friends in the VC ecosystem, me being one of them to write chapters on the various industries that we focus on.
So you know, there are chapters on AI, there are chapters on healthcare technology, there are chapters on blockchain or social media. And I wrote the chapter on FinTech. My chapter, it actually was pretty extensive. I chose to focus on the FinTech evolution that happened after the 2008 financial crisis. That was a really pivotal moment for FinTech in general, because, you know, a lot of the financial institutions either crumbled or had to retreat. And it created this opening for better customer experiences for more technology within the space. So my chapter sort of dives into that. And I’m able to interview a bunch of venture capitalists who have invested in predominantly in FinTech as well as a lot of really big name entrepreneurs who’ve done amazing things for FinTech such as David Klein from CommonBond, which is one of our portfolio companies, as well as like Sallie Krawcheck from Ellevest. So it was, it was a lot of work, but it was really fun.
Karen Swyszcz 19:23
Yeah, no, I can definitely relate because I also co-authored a book that recently came out, but yeah, no, that’s really cool. I actually added it to my reading list, but hopefully, I’ll get around to it soon. I’m that type of person who reads like three books at a time. (laughs) Constantly like adding like when somebody recommends a book, and I’m like oh yeah, I gotta add that to my list. Add that to my list. So…
Nitya Rajendran 19:43
And doesn’t it take so much longer to write a book than you thought it would?
Karen Swyszcz 19:46
Yeah, the thing is, it’s so funny, because they’re like, okay, it’s just gonna be a chapter but when you think about it never really is just a chapter like going through so many edits. And then I was like reading it over and over again, to the point where like, oh, Okay, I can’t read or edit this anymore. I need another set of eyes to take a look at it because I’m, you know, like when you’re looking at the same thing you can’t see it from a different perspective.
Nitya Rajendran 20:09
Oh, yeah, completely. I think I think you’re right. Like, you know, with Fintech in particular, there’s so many things you could really dive deep into, like all the regulatory changes. And I was like, you know, I, I don’t have time for this in the chapter. Or like, you know, I don’t know, in your book if you had to interview people, but transcribing interviews takes a surprising amount of time. I spent so many hours transcribing these conversations I had had, but you know, at the end of the day, it was so it was still a really fun process, and I’m so glad I was able to be a part of it.
Karen Swyszcz 20:41
Yeah, well, for the podcast alone, I also include show notes where it’s a transcription of the conversation so that I found it takes a little bit of time even though I am using like a tool otter.ai but obviously, it’s not perfect. So I have to do some edits. But I remember I have a blog, and for some of my blog posts, I actually recorded the interviews versus doing email interviews, which I find is so much easier. So once I recorded that, and then I realized, Oh, I’m I said I was going to put into a blog post, so yeah going through that blog post of the recording first and transcribing it into a blog post that took a lot of time. And that was before I knew transcription tools existed. (laughs). So it took like forever.
Nitya Rajendran 21:24
Yeah, I tried a couple of transcription tools. I couldn’t find one that worked for me. So next time, I have to do something. I’m gonna ask you for help on that.
Karen Swyszcz 21:32
No problem. So what would you say was the best piece of advice someone has given to you about building a career in venture capitalism?
Nitya Rajendran 21:40
That is a good question. Let me think about that. I think one of the really good pieces of advice I got was just to follow your intellectual curiosity. And I should have mentioned that also may it’s about what makes you a good venture capitalist, but I think intellectual curiosity is so important. There’s going to be like, I would say that When I’m trying to find interesting companies, one thing that I’ll do is like, I will just actually go down the internet rabbit holes. I will have, you know, a thought and then I’ll say why hasn’t anyone solved this or have they and then I’ll just start Googling and Googling and you end up reading things. But I think just sort of following that path and, you know, letting yourself indulge in that intellectual curiosity can be so important because you’re going to find random things that you wouldn’t have necessarily found before. And you know what, nothing might come of it. But something also might there have been times where I’ve done research and in all these things maybe two years ago, and then it happened to me a company that’s doing that exact thing. So I would say intellectual curiosity is you know, following that is the best advice I’ve gotten so far.
Karen Swyszcz 22:43
Mmm-hmm. So tying back into networking, so do you go to a lot of networking events where they have those pitch startup competitions?
Nitya Rajendran 22:50
Yes. Yes. Short answer is yes.
Karen Swyszcz 22:55
Cause I just like automatically think of you know, those two TV shows. For like on the Canadian side, Dragon’s Den and the US, there’s a Shark Tank.
Nitya Rajendran 23:05
Karen Swyszcz 23:05
Is it? Have you ever been a judge? Actually, on any of those? I’m curious to know.
Nitya Rajendran 23:09
I have I have. It’s hard. I think it’s so hard for founders when they do those, because a lot of times, they’re able to summarize their business in like, between two to five minutes. So I have so much empathy as they’re trying to go through that. And then it’s tough as a judge, because you’re like, I don’t really know how to fairly assess this business, because I only heard your pitch for two minutes. But you know what, I think whenever I’ve been in those situations, I do try I try. I do try and talk to entrepreneurs a little bit on the side to understand more, and then assess the best that you can. It’s also good for the audience to see what does it look like, you know, when you’re an entrepreneur, it’s kind of helpful, I think, to see, this is what entrepreneur, this is what other entrepreneurs pitches look like. And these are the kinds of questions that venture capitalists are gonna ask them so they can be more prepared when they go into a meeting.
Karen Swyszcz 23:55
Yeah, I’ve been to a couple of them and I you know, I give them props because I was I can’t even imagine like being up on stage and just you know, talking about your company with everybody like watching and you being judged. Actually, it’s interesting because an interview podcast interview I did recently, it was a pitch startup competition, but it was also cool and that you were given like play money and you can use it to like invest the play money in the startups that you thought were like deserving of your money. So I thought it was cool, kind of like pretending to be an investor (laughs).
Nitya Rajendran 24:26
Yeah, that’s a fun spin on it.
Karen Swyszcz 24:28
Yeah. Okay. So like the last question. It actually has nothing to do within venture capitalism or investing. But I saw on the company website that you love to sing and you’re really into musical theater. So I think that’s kind of cool. Like, how did you get into that? It’s great, because it’s a New York thing, right?
Nitya Rajendran 24:49
Yeah (laughs). You know, when I was a kid, I was always just running around the house and like making up songs and forcing makers to sit down and you know, tape whatever new song I’d come up with, oh, I think pretty early on, I think it was like six years old, they put me into singing classes to sort of, so I could use that creative energy if you will. So, you know, I started singing with musical theater, even just popular music. But yeah, I’ve always been a huge Broadway nerd, like, whenever we would take family road trips, we’d always be jamming out to whatever, you know, new Broadway musical whether that was like Rent or Phantom of the Opera, or, you know, we just, we jammed out hard.
I think singing has always been a really big important part of my life. I think I sang in high school and college and I worked so hard in my classes, I worked so so hard, but singing was a good outlet for me. You know, I needed to be able to sort of use my creative energy, but I think you know, it’s actually been really good for me now too. So I sort of stops singing. I mean, you never really stopped so you can only sing around the house, but I actually joined a local theater group last year and I realized it was important for me to sort of have those outside passions besides work. And I think it’s actually made me better at my job in some ways because it allows me to, you know, go and use the other side of my brain be able to sing and dance and use that sort of creative energy and then come back to my job feeling really fulfilled and like another different kind of way and be more focused in a way.
Karen Swyszcz 26:23
Yeah, as you were mentioning that I actually just had like a funny idea in my head for a musical that should be like one that focuses on like the startup community and like pitching and you know, being a VC. Would you be interested in that kind of thing?
Nitya Rajendran 26:37
You write it and I’ll star in it.
Karen Swyszcz 26:39
Alright, sounds good. If people wanted to get in touch with you and learn more about Tribeca Venture Partners, where can they find you online?
Nitya Rajendran 26:47
Yeah, you can always LinkedIn message me. I actually respond. Or you can always look at our website. I think we have an email address firstname.lastname@example.org. So either of those is good. Yeah, we actually do look at all those emails. I look at all my messages. So that’s probably the best way.
Karen Swyszcz 27:05
Awesome. So thank you so much for sharing your knowledge and expertise today.
Nitya Rajendran 27:08
Yeah, thank you for having me. This was awesome.
Karen Swyszcz 27:11
Thanks, everyone for tuning in and stay tuned for more episodes.
Transcribed by https://otter.ai