How do the best founders learn faster, think deeper, and turn that mindset into companies that endure for decades?
In this episode, host David Politis sits down with Nikhil Basu Trivedi, Co-Founder of Footwork, one of Silicon Valley’s most respected early-stage investors. Nikhil’s career spans both sides of the table, from co-founding Artsy, the groundbreaking online art platform, to investing in category-defining companies like Canva, Lattice, Frame.io, and The Farmer’s Dog.
Nikhil shares how he evaluates founders, why the “slope of learning” is the most important quality he looks for, and how he builds long-term partnerships based on trust, curiosity, and shared ambition. He also opens up about the changing venture landscape, the hype and opportunity of AI, and what it means to be an investor who has truly walked in a founder’s shoes.
Understanding the Importance of Learning: Nikhil emphasized the significance of the “slope of learning” in evaluating founders. This refers to a founder’s ability to quickly learn and adapt to evolving market conditions, especially in the fast-paced AI era.
Making a Lasting First Impression: According to Nikhil, the first few minutes with a potential investor are critical. Whether it’s 15 or 30 minutes, founders must capture the investor’s attention and highlight their vision’s potential.
Pitching with Conviction: Nikhil advised founders to clearly articulate why their business has the potential to be massive. It’s crucial to strike a balance between ambition and grounded reality.
Value of Ongoing Communication: Post-investment, Nikhil stressed the importance of maintaining regular communication between founders and investors.
Leveraging AI for Better Investments: Footwork has been proactive in using AI to manage and analyze portfolio companies, allowing them to track company progress and trends efficiently.
Empathy from Experience: As a former operator and founder, Nikhil shared his belief that empathy is crucial in the investor-founder relationship. Understanding the challenges founders face allows investors like Nikhil to be better partners, offering thoughtful guidance rather than prescriptive advice.
Quote of the Show:
“In the first 30 minutes with a founder, I’m trying to assess their slope of learning… We invest in slope, not just smarts. How fast a founder learns matters more than what they know on day one.” - Nikhil Basu Trivedi
Links:
LinkedIn: https://www.linkedin.com/in/nikhilbt/
Website: https://www.footwork.vc/
Ways to Tune In:
Substack:
Spotify:
Apple Podcasts:
Transistor: https://podcast.notanotherceo.com/
#NotAnotherCEO #BusinessSuccess #Footwork
Chapters:
00:00 Intro
01:27 Key Traits in Founders: The Slope of Learning
04:59 The Importance of First Impressions in Pitching
13:48 Evaluating and Supporting Portfolio Companies
19:44 The Impact of AI on Venture Capital
24:04 The Value of Thought Partnership
31:10 Reflections on Missed Opportunities and Career Choices
36:30 Future Aspirations for Footwork
38.25 Outro
Transcript:
Nikhil: [00:00:00] I think that very specific thing for venture investors is, how this business becomes really, really, really big.
David: Today’s guest is Nikhil Basu Trivedi, one of the most thoughtful and well-respected early stage investors in Silicon Valley, unlike the majority of venture capitalists, Nikhil started his career as an operator. He was one of the founders of artsy the online art platform that changed how the world discovers and collects art.
And he’s already had an impressive career in venture spending time at Insight Partners and Shasta [00:01:00] Ventures before co-founding footwork in 2021. Over the course of his career, he’s invested in companies like Canva, frame.io Lattice, the Farmer’s Dog, and Honeydew Health, just to name a few. When I asked one of his founders to describe him, they said he’s a mensch who sees through the noise, focuses on what matters, and always thinks from first principles.
I couldn’t describe him better myself. Please welcome Nikhil.
Nikhil: Thanks, Eric. Great to be here with you.
David: I am excited to do this. Um, okay, so we’re gonna jump right into a first question I ask every investor. What is the one thing that you look for in founders or companies that you invest in?
Nikhil: I think right now the characteristic that my partner, Mike, and I. most hone in on, when we’re evaluating founders is their slope of learning. And, so what I, mean by that is, how quickly can a founder learn, are they sort of constantly curious [00:02:00] about their business and, what could evolve in their business? Are they showing that slope of learning in just. their, decision making, how quickly they move on a potential opportunity. And it feels like that characteristic is just more important than ever in this AI era where, so much is changing so quickly. And so I think since we started footwork four and a half years ago to today, our emphasis on that slope of learning quality has kind of continuously increased. And now is sort of the focal point. if you press me on like the one thing that we look for in founders, it’s the focal point of our evaluation.
David: And like how fast can you assess that in someone? Or maybe how do you assess that in someone?
Nikhil: your question of how fast in the first 30 [00:03:00] minutes I spend with a founder, I’m trying to. Assess that, to decide, am I gonna spend another several hours with that founder or
that Team? Am I gonna really dive into the business tonight? And so I try to make a call on it in that first meeting, to assess it. I’m trying to pick up on, you know, how that thinking on the business has evolved.
I’ll ask questions such as, take me through some of the highlights in the game film between when you started the business or when you had the idea for the business to where you are today. Just to see like what they pick up on in their own journey as they reflect on it. and what were some of the key learning moments to try to assess? Is there slope in their thinking, in sort of their actions over time? I think you get a [00:04:00] sense for it in the back and forth that you have with the founder, but then to get to a final investment decision beyond that first 30 minutes, it’s a back and forth that we have, you know, over the course of a week or a couple weeks, however long the process ends up being. where we’re really trying to assess that slope of learning and more.
So examples where, in the case of honeydew, for example, a mutual investment of ours, David Futoran the founder, CEO, and I. Chatted on an almost daily basis for like a couple week period. and so like, you know, text back and forth, quick calls to, try to really understand his thinking. And in that case just got more and more excited about his slope of learning as a founder the qualities we saw in him that led to us making the investment.
David: It is interesting ‘cause actually, as you’re saying this, now I’m thinking back to some of my investors at BetterCloud who would do one of them. I [00:05:00] got a warm intro and he said, Dave, I’ll do a 15 minute call with you and if I like you after the 15 minutes, I’ll fly to New York to meet with you. And I said to everyone, I’m like, that’s kind of crazy.
Like, is he gonna know in 15 minutes? You know, is it worth spending time with me? But as I’ve now started seeing a much higher volume of companies, you do realize that there’s something, there’s something pretty quickly. Maybe it’s not 15, maybe it’s 30 minutes like you said, but there’s something that you very quickly get a sense for how someone thinks about their business, how they describe the business, how excited they are.
And that happens in a pretty short period of time.
Nikhil: For sure. That’s why I think that. The takeaway I would encourage founders to have from this is whether it’s 15 minutes or 30 minutes. What you have when you meet a potential investor is the first five minutes to really capture someone’s attention and to get them to lean in for 10 more [00:06:00] minutes,
for 25 More minutes, to get them thinking they have to go fly to, meet
me next week To spend more time. And so I always encourage founders to think about what they wanna say very carefully in that first five minute window that they have in every new meeting with a potential investor, because that’s your opportunity to really hook someone in.
David: You’ve invested, obviously in a lot of amazing companies. I, I could have mentioned many more than I did in the intro. When you invest really early, which you, which you now do very early stage, how often is the idea that they end up. Kind of building a real big business around how often is that idea the same one
Nikhil: Hmm.
David: They came to you with in that first meeting?
Nikhil: You know my personal bias. Has been towards companies that do have some early signs of product market fit at the time at which we invest.
David: Hmm.
Nikhil: And so there’s, there’s typically something there that’s, that’s just started to work. It [00:07:00] was Canva, six months post-launch. Um, you know, uh, the farmer’s dog with of dogs as customers.
Um, uh, I think about a year post-launch. so. I have been more focused at that stage where typically idea evolve and pivot into something else, um, versus at the pure founder and idea stage where of course it does. Um, and so yeah, I have a few examples of companies in that, in that other bucket, a company called Ellis, for example, which is today has merged with a company called Camu in Healthcare. Um, company valued at $6 billion. It started off in blood diagnostic testing and today it’s in revenue cycle management and, uh, and software for healthcare. Um, so it’s, it’s [00:08:00] taken a bunch of twists and turns to get there
David: Hmm.
Nikhil: You know, that initial round you know, I, I was lucky to be one of the early investors and really based that investment position on the founders more than anything else.
Uh,
David: Hmm.
Nikhil: But the vast majority of the investments that I’ve made in my career, you know, the idea I invested in, the thing that I got excited about ended up being, you know, the, the thing that they worked on the whole, uh, duration of the business.
David: Hmm.
Nikhil: So hopefully that makes sense.
David: Yeah, makes sense. And then when, when people come in to pitch you, I’ll speak for myself first time founder, pitching a well-known investor, you’re pretty nervous. You’re pretty, you know, you don’t, um, it’s, it’s, it can be challenging. Um, when you think of the best founders that have ever pitched you, what is it in that pitch?
You’re looking for the slope of learning, but what is it in the actual pitch of how they tell the story that really makes them. Stand out to you or get you [00:09:00] excited because this is one of the learnings I’ve definitely had recently is as I’ve spent more time with venture investors, they’re looking for something very specific.
There’s other ways to go and raise money. There’s other, but specifically venture capital investors are looking for something very specific. Like, what, what is that in your eyes when someone’s coming to present?
Nikhil: I think that very specific thing for venture investors is how this business becomes really, really, really big and. I think the founders that are the best fundraisers and storytellers, um, get to the heart of that very quickly, like why this is such a massive opportunity, why it may not be a massive opportunity today, but why it will be a massive opportunity tomorrow. Perhaps a unique insight that they have that others don’t [00:10:00] have, for, for why that will be the case. Um, and so I think there are some fundamental characteristics of the best companies, uh, that I’ve seen over time, which is, uh, as I said earlier, they hook you in the first five minutes. Uh, the founders are able to do that as they tell the story of the business. Um, they have unique insights that other people don’t have. You almost feel as an investor, like you’re learning from them. You, you, you picked up on something. Um, that you didn’t realize, uh, again, in a, in a pretty short window in that, in that initial meeting. And then as you sort of unpack it in your head as an investor as well, um, and then you, you, you come out of the conversation feeling like, wow, could be one of the ones. ‘cause what we’re seeking in our business of venture, is a company that 30 years from now [00:11:00] is. Uh, is is still going and compounding even at, at massive scale. Uh, that’s one of the measuring sticks that I have for my career is, I wanna have a handful of companies 20, 30 years from now I’m still holding onto as an investor where I was lucky enough to be a partner to that company at the c, the series A and, and so. It’s just different to, you know, you can make a great investment by investing in, you know, uh, a restaurant business that, uh, you know, may, may still be around in 30 years, but isn’t compounding at, uh, the rate at which, you know, an s and p 500 company is compounding. and so that’s, uh, that, that, that sort of articulation for why this can
be Very, very big tomorrow. And what’s changing in the market to enable that [00:12:00] or what is currently changing in the market to enable that? I think that’s the very unique thing that we seek out as venture investors.
David: So I had, I had someone pitch me earlier today and it was a great idea and that thing that you’re saying. Was 20 minutes into the pitch and I told him, I said, I felt the, the way you’re describing this is literally how I felt this morning. I said, oh my God, I’m learning something that I about the SRE space that I had no idea about.
I said, this is amazing. Why don’t you start with the end, you know, and tell me upfront how big this thing. He says, well, I’m scared that investors are gonna think that’s too big. I am scared they’re gonna think I’m like Adam Neuman or something, you know, pitching WeWork, like, what is your take on that? You know, in terms of does it come across like that, you know, or, or is that really because of what the venture business is?
You need to see that and, and hear that.
Nikhil: I think the best pitches are ones that seem like they can [00:13:00] be very big. That the comp that the founders have, you know, serious ambition, but that, that ambition is not delusional. it’s grounded in some factor reality or, or, or something that they are already seeing show up in the product, in the business. Um, something that’s, a, a real unfair advantage around doing versus anyone else. So. that’s the nuance, right, is you, you can’t tell that really big idea and vision and have it seem credible unless there’s something, uh, that you have as a foundation for why that will actually happen.
David: Hmm, Hmm. That makes sense. Um, in terms of once you’ve made an investment and you’ve actually gone through with that, you’re, again, you are early, but you’re not an inception stage. You’re, you’re kind of, they have some product market [00:14:00] fit, they’ve got a business going. How do you like to work with a founder specifically?
How do you want to be. Communicated with, once that deal has closed,
Nikhil: I think, um. Especially in the early days after making an investment, regular communication to develop trust for an investor, to develop context on the
business Is really important. regular investor updates, whether we do that monthly, it’s awesome to get like a written investor update, every month from a founder. and then perhaps to do a quick call to chat through a few of the key topics that surface there, or a few of the key questions that a founder is wrestling with. and, to not just do an, update call to rehash what’s in the email to actually go into like some discussion around a couple of
key topics That’s, pretty typical [00:15:00] cadence that we have with the founders that we invest in. It doesn’t have to be every month, but, some sort of regular cadence. of updates, calls to develop context, frequent text back and forths, that are typically for us as investors pulled from the founders versus us pushing things under the
David: Hmm.
Nikhil: Founders.
Uh, we, you know, we don’t want to be a nuisance and a time burden for the founders that we invest in, but, but there’s lots of questions that, you know, you have as you build your business that come up that I think thought partnership is valuable for. And
David: Hmm.
Nikhil: Try to, to try to be that thought partner and to develop that trust and develop a regular cadence. so we have context, especially in the early days of a new working relationship and a new investment.
David: I don’t think I’ve ever asked an investor this question, but I, I’m curious, you’ve made a lot of investments, um, you know, and it’s a lot of things to keep in your brain about all the different businesses. Do you have [00:16:00] some system to, to keep all. I have a hard time keeping track. I’m not, I’m not even a professional investor.
I have a hard time keeping track of the companies I’ve invested in advising. Like how, how do you do that at scale?
Nikhil: Yeah, you know. A lot of this has just lived in my brain for the last 15 years, I get older, I think I need to have more system and process. ritual that we have at footwork is Mike and I and with our broader team, talk about every single portfolio company every week. we don’t just, know, uh, talk about. Updates on the companies that we, you know, maybe had a board meeting with in the prior week or where, you know, something came up over text. actually go down the list and we talk about every single portfolio company. Um, now for us, right now, that’s 23 companies, so it’s not a huge end, but it’s still enough that it, it takes a little bit of time. The reason for that ritual is we think it’s really [00:17:00] important for us to have shared context on. Any data points that we have that are going on with every single one of our portfolio companies, so that if them walked into our office, uh, today, everyone on our team would have a sense for what’s going on with that founder. Um, so that, you know, if we hear about a great, talented person who’s looking for their next opportunity, it doesn’t matter who heard about that person, we can all. We all have enough context to try to figure out, oh, that person could be a really great fit for this company because we know this company’s looking for a designer right now.
And you know, or like, these are the three companies that will actually hire like a business generalist right now in our portfolio because growing very quickly. They have that need. Their chief of staff isn’t working out that well, you know, whatever it is. Um, so that’s one ritual that we have. And then the other thing I’ll say about this is. I do think there’s a lot of areas in [00:18:00] which AI can really add value to us as venture investors, and I
David: Hmm.
Nikhil: One of them. And so, you know, at footwork we’re building a system where, uh, every one of our portfolio, company updates, every board deck that we get, every email update we get is in a single uh, uh, uh, database.
David: Repository. Yeah.
Nikhil: And where we can query that with large language models to a look at, you know, what, what it found to say they were gonna do versus what they did. What was some of the key challenges and areas we talked about before and now what are they, how’s, how’s the business evolving as a result? so we have kind of a pre-read every time we go into an update chat with a, a founder that sort of breaks down some of the things that would be interesting to talk about based on the history. Um. By the way, what’s, what’s happening in the broader market as well, and not just in the context of that company. Uh, and I think that that is only [00:19:00] going to improve as a capability for us as these models get better.
David: That’s a cool, that’s, that’s cool. And you’d be able to see trends across them and see kind of that’s cool.
Nikhil: you know, if. Uh, and I think it’s very important for actually any company, uh, a venture firm in our case, or you know, a startup or frankly a big company, to, to do this exercise, which is sheet of paper. If you restarted the firm today, what would you do? it’s pretty obvious that if we restart footwork right now, we’d be building as an AI native firm. And so we’ve tried to embrace that this year uh, it’s obviously an ongoing journey for us. Uh, hopefully I just give you a peek into some of the.
David: Yeah. Yeah. That’s cool. So you’ve, you’ve invested through multiple different trends, cycles, you know, new technologies. What, what is your view on where we are right now with ai? Like as we’re talking, do you think we’re at the peak of this hype [00:20:00] cycle? Does, is there still more to go? Is it not even a hype cycle?
You know what? What do you feel, and you’ve seen a lot of this in your career.
Nikhil: Yeah. What I feel is, I think it’s the most exciting time, perhaps in my whole 15 year career to be an investor, uh, and also one of the most scary times. And so let me unpack that. Why. Why do I think it’s so exciting? I mean, we’re seeing companies grow at a faster rate than ever before, and I think there’s a lot of public stories now around, companies that have gone from zero to $2 million in revenue run rate in 10 days.
We actually have a company in our portfolio that this happened to. Um, but beyond just those, you know, uh, those sort of crazy headline type numbers, the market pull for a set of businesses is unlike anything I’ve seen in my venture career. You see that in GPT, right? Getting to, I think now close to a billion active users [00:21:00] in than three years since it launched. Um, that is remarkable. Uh, you know, I don’t think we’ve ever seen, we’ve never seen music growth, uh, at that level and to that level of scale. Short period of time and you’re seeing, uh, user growth in their case, revenue growth in their case, and revenue growth in a set of businesses case that that’s unprecedented. Um, more broadly speaking, I just think, uh, AI will be the technology market going forward and, and so, you know, it, it will just be one and the same thing. and I think, you know, every business is reevaluating its stack with AI that leads to a lot of new opportunity. I think, uh, it, it impacts almost every business and industry.
And so it’s, [00:22:00] it’s um, an incredibly exciting time. Why is it also a scary time? I think we just have a lot of dollars in our market of venture, and so, um. It, it, it absolutely feels like a hype cycle in a bubble right now as well because, um, the, the types of, uh, rounds being raised at, at valuations relative to the fundamental progress seem absurd. for, for some companies, it, it will work out fabulously well because they’ll build enormous businesses. But I do think there will be pain. Um, and there’ll just be a set of stuff that that doesn’t work out just like in every other era. But you know, am I overall Absolutely. Like do I think be a set of just amazing businesses get that get built, uh, know, over the next five to 10 years?
[00:23:00] Absolutely.
David: Hmm. Yeah, it’s interesting, you know, for me, I’ve kind of seen this, uh, very closely. You watched and worked through the rise of SaaS and, you know, the adoption of SaaS. We started measuring it in 2012, and if you look at that adoption curve up until 21, which was the peak, you know, it took time, but it was, it was growing very, very quickly and then of course peaked in 21 in terms of the number of SaaS apps that people were using and how they were buying it.
I feel like I’ve seen in. Four, like 24 months. The same type of thing for ai that took 10 years basically for SaaS. And you could argue the same for SaaS. It changed everything, changed every company, everyone became technology company, all this stuff and, and with ai, it’s happened so fast. And just like SAS came back down, the question is, you know, kind of where’s the peak, where’s it gonna come down?
But it doesn’t mean that there’s not gonna be a whole set of new companies that are there forever, you know, for, to your point, in 30 [00:24:00] years we’ll still be there.
Nikhil: Totally. Mm-hmm.
David: Um, in terms of the value that you bring to the table through something like, like a movement, like that’s happening with ai, you’ve got these companies, you’re investing, where do you.
Add the most value. Um, and I’m curious if that value you add is different from some of the other firms you’ve worked with, like worked at in the past.
Nikhil: Yeah, I think where we at footwork really shine is being a thought partner in. A handful of really important moments that inevitably come up, every year for a company. and so by, by being a lead investor at Cedar A by having the type of context on the business that I tried to describe earlier with the [00:25:00] regular cadence of updates early in our relationship, um, can hopefully show up as, uh. A really valuable thought upon it in, a key hiring decision uh, new fundraise um, a big strategic question on, the product footprint. And, you know, uh, do we prioritize this next right now versus do we double down on the thing that is already. Uh, launched and, and and working. same thing on the go to market front.
You know, do we prioritize this one channel that’s working really
David: Hm.
Nikhil: We actually go run a bunch of experiments in this moment in time to figure out other channels that could work? Almost every company I’ve worked with, you know, goes through, um, a handful of these moments every year [00:26:00] and a handful of these big decisions and, uh, think we. Where we show up relative to other firms, uh, that I’ve worked at that I’ve worked with, um, is that we really invest the time to think about these decisions alongside the founders. try to not be prescriptive. We try to not just take the pattern recognition we’ve seen from other companies and say, Hey, this worked at other companies, so I think this is what you should do.
We try to think about each of these questions on first principles, um, because there’s nuance to the answer in every case. And, and so I think that that’s what you’re, that’s what you’re hiring us for as, a founder raising a seed or a series A deciding to work with footwork is. Um, you know, these, this is a, a small firm, an equal partnership firm. [00:27:00] I get this combination of investing and operating experience in my people there in, in, in Mike and Nick Hill today. Um, uh, only make a handful of investments every year and they care about, uh, this company that I work on as a result of that kind of concentrated approach. And, uh, and they’re gonna really. Be great thought partners in, in these moments that are for sure gonna come up in the course of my, my business building journey.
David: Do you think that your experience as a founder first. Impacts this approach.
Nikhil: You know, I think the empathy that have, having been a founder of a venture backed startup, and then also. That Mike and I have, having founded a venture firm together is, is really helpful [00:28:00] because it, you know, we start from a place where we, we know like really hard and these decisions are really always tough decisions and, um. It’s also lonely, uh, you know, making the decisions on your own. And so, um, yeah, you know, I think maybe subconsciously we try to be the, the, the type of partner that we wish we’d had, uh, in our own business building journeys, both Mike and me. Um, hopefully we show up with some greater level of empathy than someone who’s never started anything before, because I do think it’s just different. Um, one, one refrain I’ve had, I think I’ve tweeted this before, is, um, no one cares as much as the founder Kes. And I think unless you’ve actually started something, you don’t understand what that means. Like,
David: Hmm.
Nikhil: You know, [00:29:00] you think about it the time in a way that. No one else really does or ever will. Maybe you’re lucky, you know, you find, you hire somebody who, who somehow cares at the same level as you, it’s, it’s incredibly rare, right?
Like it’s so, so I do think there’s probably something there that enables us to show up, enables us to show up at, um, just a slightly different level than average vc.
David: Yeah, I think, I think at the stage that you’re investing, having somebody who’s been in the seat before, there are some amazing investors out there who’ve never operated, but at the stage that we’re talking about. It’s hard to know the pain. It’s, it’s actually very hard to know and recognize and empathize with the pain unless you’ve been through it like you said there.
There is no, this has been my biggest topic that I’ve been talking about, writing about, like the last couple of weeks, has just been [00:30:00] the challenge of being a founder, CEO and, and how lonely. That is and how hard it is. And I think having investors that, that can get that and come at it, like you said, from first principles and not say, well, 72 other companies did it this way, therefore you should do it this way.
When in reality there is something different about each company and the DNA and the market and the founder and the product and the customer. And, and so I really, I really, I I, I like that and I think, I just think it’s an important one for. For founders to hear that, because I think sometimes you can get enamored with this idea of like, oh, they’re gonna have this, and they, they help me with my recruiting and they help me with my in, in theory.
Of course. You, you said it before. You do that and you want to help and, but there’s something about just having the thought partner who’s kind of aligned with the, with the founder. We’re trying to build a successful business here. Let me help you, you know, and, and, uh, be there as your thought partner. I think I, I really think [00:31:00] it’s, uh.
I, I tell people a lot. I think the firm matters a lot less, in my opinion, than the person. Um, at this stage. At this stage. Um, what do you, what do you think of, of, um, you know, of all the deals that you’ve seen over the course of your career, um, what, what is the deal that you missed, the big, biggest deal that you missed?
Nikhil: Yeah. Uh, sadly have, have missed, uh, a bunch. And that, I think that’s the nature of, of venture investing is you, you end up, you know, your anti-portfolio of the stuff you didn’t do ends up. Almost always being better than, than the portfolio you do do. Um, a painful one for me is Robinhood, which I think is now, uh, you know, uh, trading at like a hundred billion dollar public company. I haven’t looked at the, the, uh, I do, you know, I do own the, the public stock at least. And so, [00:32:00] um, yeah, $117 billion as of today. I was really fortunate to meet, uh. V and Bei. Uh, in the early days, I went over to their office in Redwood Shores. Uh, had them come in and present to our team, uh, at my prior firm.
And there, in my mind was a lot to like about Robinhood. Uh, I was also in the, this was the stage at which they were, they had a, a beta of users. Um, they hadn’t fully launched yet. They had already raised a seed round. They were thinking about a series A. Um, and index ended up leading that series A round and, and that was a fabulous investment for them. Um, what unfolded with it? I think what I felt is mobile had really changed the game, uh, for what was possible with stock trading. And Robin Hood was perfectly into that. Um, and so, [00:33:00] you know, you kind of feel it was this magical experience to be able to trade stocks on your phone. To be able to do it for free. I thought that a lot of people are gonna resonate with that experience, at least in my generation. You know, this is back in 2015, I was 26 years old at the time. I was sort of a great ICP Robinhood customer. Now, where we got hung up as a firm and where we had a lot of debate is such as, is this what people should really be doing as investors? Um, I had a partner who felt people should really be investing in ETFs and then.
David: Hm.
Nikhil: In strategies like that versus, versus just trading individual stocks. A lot of people are gonna lose a lot of money doing that. my perspective was perhaps a bit more libertarian on that. Like, I, I, I, and I sort of felt it as an n of one customer.
Like, I just want the power to be able to do this. Um, and so, so anyway, you know, kudos to, to those guys and, and how they’ve executed on [00:34:00] the business. I think it’s pretty awesome that they’ve now built. Uh, seven or $800 million plus revenue businesses within Robinhood. So they’ve executed on multiple acts post, you know, free stock trading on, uh, the iPhone as the wedge.
David: why, why did you become an investor in the first place? Like why, why transition from an operator, founder to, to an investor?
Nikhil: I got my start in investing in Insight Partners out of New York, and I just ended up loving. Ability to have conversations with entrepreneurs as my day-to-day job. it’s really been about that love of the day-to-day and of getting to meet these incredible people every day who are building, uh, businesses that are going to be the future. Um. It’s kind of still amazing to me that that is my job. [00:35:00] Like I, you know, I get, I get to meet them, I get to evaluate them, and then if I’m really lucky, a handful of times every year I get to invest in them. And, and so way this job just satisfies my intellectual curiosity, um, you know, the, the sort of, it, it also plays into like my competitive nature.
Um, ‘cause you do have to obviously be able to mm-hmm. over the best founders as well. Um, and then I, I do get a lot of energy from just working closely with these founders once we invest. Um, and so, you know, the reason why Footwork has this approach of just making handful investments every year versus, you know, uh. Being a small, uh, investor in a lot of companies every year or, or a strategy like that is I just really value the human relationship we get to build with the entrepreneurs that we work with and trying to really [00:36:00] be there for them during the tougher times and, and being partner and pushing them even when things are going well. Uh, and so, you know, all of that is sort of. energy that I get from the day-to-day work and why I continue to love doing this. And it’s why I,
David: Hmm.
Nikhil: You know, I dipped my toes into it 15 years ago at Insight, uh, it’s why I just kept doing this now, uh, since that moment.
David: Where, last question for you. Where, where is footwork in 10 years from today?
Nikhil: I think our aspiration is to be of the handful of firms that. Uh, a wide set of founders, uh, thinks about as the, you know, as one of the five to 10 firms they go to for leading their C or their series A around. And so what we want to be [00:37:00] is, um, a world-class brand focused at the early stage. Investing in a small handful of companies every year.
This combination of investing and operating experience in our, in our partnership, um, we really love businesses that are a mix of both consumer and enterprise in their DNA. And so obviously OpenAI is a canonical example now, right? With chat GPT, but for consumers and used by businesses. Canva is another example where the business grow, grew organically amongst consumers and prosumers and then infiltrated the enterprise. If you think about the biggest companies in the world, most of them serve both consumers
David: Hmm.
Nikhil: And enterprises. From Google to Nvidia to Microsoft to um. Open AI and others coming up. And so our aspiration 10 years from now is to be one of the five to 10 firms that the, the most ambitious, the [00:38:00] the best founders, uh, are thinking they want to talk to for their C or their series A. And hopefully our work is sort of speaking for itself 10 years from now where we have already backed, uh, a handful of companies that feel like they’re on that trajectory too. ones that, uh, we all still wanna hold though to use from.
David: Hmm. Awesome. Nikhil. Um, thank you very much for doing this with me. I know you’re extremely busy. I’ve been looking forward to this conversation. So thank you a lot for founders to learn from this and, um. So thank you for doing this with me.
Nikhil: Really appreciate you having me here, Dave, and thanks for doing this for founders.
David: Awesome, awesome. Well, everyone who’s listening, I hope you enjoyed. If you did, please share this with your networks and, uh, we’ll see you for the next episode of not another CEO podcast.
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