Ep. #10, Feat. Array Venture’s Shruti Gandhi

Peter Chapman: Okay Shruti, welcome to Venture Confidential.

Shruti Gandhi: Thanks for having me.

Peter: I'm so thrilled you're here. We start all these the same way which is with your own story and how you got into venture.

Shruti: Obviously my story is I didn't think about venture and just got into it.

Peter: You just stumbled into it, that's common.

Shruti: So my story is I didn't know what venture capital really was until I started a company and when I wasn't sure what to do to run different parts of a company outside of the technical problem solving required, I started digging more into venture capital. I realized that I should spend a little bit more time learning about how the venture business really works to build a venture backed company.

And so I can then go back and start another company after that so that's how my inception of me being in venture capital really happened. And then I spend a lot of time working at firms like Bank and High-Bar and others as an intern. But after that I started working full time in venture at Samsung and after that at True and two years ago I started my fund at Array Ventures.

Peter: We haven't spoken to anyone who's done corporate venture yet, what was that Samsung experience like?

Shruti: Frankly speaking

There's a taboo around corporate venture but as someone starting out in the industry it was an amazing platform.

To be able to just go and do what I wanted to do frankly like at a bigger firm when you're a junior, you have this hierarchy, you know. Your partner does deals and you're assisting your partner but at a corporate venture I was lucky enough to work and have the lever to just you know, source my deals, be on the boards and then fortunately early on I experienced my companies being acquired by Apple, McGraw-Hill, Samsung, things like that.

So I think that was, while all the people only talk about the negatives, as a junior person in venture it was an amazing platform 'because from there on I was not a junior person, right and you could go to another firm and elevate yourself a little bit more.

Peter: What were some of those early wins?

Shruti: A company called Engrade that got acquired by McGraw-Hill and a company called LearnSprout that was acquired by Apple and one of my companies in the security space called Imperium has just raised a serious deal with SoftBank and I can keep going. It was pretty amazing because I was able to source these companies and be a board member and all the things you're required to do when you're a senior partner institutional fund.

Peter: How are you sourcing such great companies as a sort of junior person at Samsung?

Shruti: Good question. I would say

I'm very thesis driven so oftentimes I like to go after problems from a perspective of "let's study the industry." It almost becomes a learning mode. It's like taking a class at university on education at EdTech.

And then just going to school every day and talking to folks, reading as much white paper, whatever it is in the industry, talking to the experts, talking to the investors and creating a point of view so that's as an engineer, for me that's the most logical way to structure my work. And from there on I start creating a point of view on where I think there's a need and then I start talking to people about "hey, do you know of a company that solves this."

And obviously when I'm reading if I find something I'll reach out. People assume venture is just inbound but it's not, it's also a lot of outbound. If you have a clear thesis on what you want to do, that's what I tend to do.

Peter: Could you walk me through an early thesis that you built?

Shruti: Yeah, I think I guess the education one would be a good one. Samsung was trying to solve a problem around how do we have these tablets in classrooms. This is around 2012, 2013 timeframe. So how do we have these tablets and classrooms and Apple iPads were everywhere and so I started talking to teachers, I started talking to principals, school districts, just kind of understanding what they love about iPad and I started realizing that the biggest missing piece was content.

So people would say, "I like these iPads but we have to figure out what to do with these iPads." You know and then the other things are more hardware like we have to charge them often and we have these little trolleys we charge them and so once you figure out the problems and you start sorting them so I had a little distribute, a little two by two.

If I remember correctly, one was content, one was marketplaces, one was data and one was more backup plumbing and that was in K12 so that's what I did and I started to see where there were open gaps around all the companies trying to solve these problems. And then from there on who was solving it and who's in the best position to solve these problems.

And I ended up investing a lot in the data and personalization category because that is my strength as a software data engineer for 11 years. And pairing that with the tablets would have been an awesome strategy to then go to schools and say, "We have everything for you, here's a one stop solution," so that's what we were trying to solve at that time.

Peter: Awesome so as far as I can tell before you got into venture, you had very little exposure to EdTech.

Shruti: Yeah, I just went to a lot of schools. I'm Indian.

Peter: Oh, sure, sure. So tell me about this educational process. How do you do this original outreach? Did you just blindly introduce yourself to a bunch of principals?

Shruti: Yeah.

Peter: And once you've got this thesis like "I think there's a play around data on school owned iPads," how do you then source companies that fit that niche?

Shruti: As I said just reading a lot, talking to a lot of folks, talking to experts. I was talking at that time to connecting with like Kevin Johnson, I think mayor of Sacramento and Adrian Fenty who was ex-mayor of D.C. and also working at Andreas on education initiatives so you know basically just talking to folks who know a lot, not just investors but industry folks and seeing what the gaps are at different levels of the need the industry has.

Peter: Okay, so you spent two years at Samsung, you realized early on you're a thesis driven investor, you're coming up with hypotheses on what the market needs and you're doing a whole bunch of research. Let's fast forward a handful of years, it's time for you to start your own fund. What was the impetus for starting your own fund?

Shruti: So when I was starting my company I realized that a lot of the help I need was around go to market. You know strong technical founders, my co-founder and I met at Columbia. We knew what we needed to do to solve the problem technically but we didn't know what it meant to make money off of something and I think having a good set of folks to help you think through that would have been helpful and I started scanning the market and I realized that a lot of the firms were equipped to help founders at a more later stage.

They tend to be the Hendersons of the world with the big army and big checks. So when I was exploring that I realized that

There are many founders who are really technically savvy but don't have the know how beyond building the company from the technical perspective, especially the first time founder to get up and going, running.

But the paradox is when you're a small fund, how do you manage as Heavybit you know, how do you manage the cost and the infrastructure to help founders and give them the support they need and at the same time you know, go for returns and get enough ownership and all that. I mean how do you scale your business basically? So to solve that problem I started Array.

And the goal for Array is to help founder from the early days of inception to help them think through their go to market strategy, to help them think through how they get their second wave of customers. So usually when an enterprise founder leaves their job they have a few friends willing to try their product out. But then getting from that two or three customers to the fifth and the 10th customer often is very difficult as you get immersed in product building and that's what Array helps you think through.

How do you build your second wave of customers, how do you grow your revenue from zero to a million in 12 to 14 months and we are programming our workshops, events, everything is catered around go to market strategy and doing that more just on enterprise companies and scaling it just for that not consumer but enterprise companies allows you to scale that in addition to using a lot of technology on the backend which is what we do.

Peter: So enterprise only, early stage. How early does Array invest?

Shruti: I would call any round that's half a million to two million dollars in an appropriate round for Array to participate in. But we call ourselves an enterprise early deep tech fund.

Peter: I like that, enterprise early deep tech fund. What are some of the common tips you find yourself handing to founders as they think about building that second wave of customers?

Shruti: So here's a common story. Peter is a high paid executive at Google and Peter is agitated about the tools that Peter's forced to use at his company. I call it agitated workforce and then Peter from thereon goes and says, "Well let me see if someone's making this outside, if I can buy their product as a customer." And then Peter scans the market and finds nothing so then Peter's still frustrated having to use these old tools inside Google or wherever else and Peter's drinking with his friends and goes, "I think this needs to be solved."

And Peter's friends go, "If you build it, I'll buy it," so Peter's like, "Really Tom?" and then Tom one, Tom two, Tom three all give Peter this validation but now what Peter forgot to ask Tom is how much will you pay? And oftentimes the mistakes founders make is doing that math of is it worth my time to go build this and is it big enough of a market so if Peter builds it for Tom, I mean is Tom going to just pay $5 a seat in his company.

Is he going to pay maybe $50 per month. Is that worth the founders time to go build a company around it but often founders or technical founders are very uncomfortable or maybe they're not uncomfortable, then they forget to ask or make that link.

So that's our diligence, understanding what an average contract value would look like, is this repeatable, can the founders do this 10 times in the next 10 months and is this scalable, is this a real need?

So those are commonly the questions I often tend to ask founders around what exactly did your friend promise and can you find less former connections to sell this to and build a big business around it.

Peter: What are some early indications that businesses can in fact turn into billion dollar businesses? What are some positive signals you look for?

Shruti: Usually it's a team. Once I do this problem solving and it's a real enough need and I can do this homework around, okay I think there's a need for this problem and from thereon, I think this team is the right team to build it and then this team has the right contacts and contacts in the category that they're solving the problem in. I think those are the three big things I look for to then make it potentially a large billion dollar business. This is such an early business that I can't predict. If I was able to predict I should be a billionaire myself by now.

Peter: I'm assuming you're still thesis driven.

Shruti: Very thesis driven.

Peter: What's a current thesis that you're looking for a company to fit.

Shruti: Health, I would stay I'm looking at a venture health. There's also blockchain. My first job as a developer was in the crypto-security group and then a couple years ago I developed a thesis in blockchain world but I concluded it was a little early for us to invest in early stage and now I'm back at it because I think the markets are ready, our customers are ready. I would say I'm still looking for a lifelong learning education investment category.

And my bread and butter is security deals. I love anything in that or the plumbing business of data. So I want something in the Edge Computing category so I can keep going but I have a lot of point of views on all of these.

Peter: Yeah that was plenty. I'd love to deep dive into just one and it's come up a lot recently so we're going to pick blockchain. What's the next blockchain company going to look like? What do you think we should be looking for?

Shruti: I'm sure there are other folks, more experts to kind of have a stronger point of view there but I think for me, I'm looking for something in the enterprise play which would be around smart contracts. I think fraud or storage of records is very important. I keep thinking about the Equifax attack that keeps me up at night frankly and how something, there are ways to solve that problem and how we sort our records so those are the kind of things I look for.

Peter: Let's say that you've done your diligence and you feel good about the market, you feel great about the team, you feel good about what that total contract value can look like for this product and you sign a company. Oh actually I should have asked, how much do you invest? You said that rounds are between half a million and two million.

Shruti: When I'm leading, it will be either full rounds, half a million or so or I can put in a smaller check depending on if someone else is leading.

Peter: Do you have a preference for whether or not you lead?

Shruti: If it's an industry I know well I want to lead.

Peter: Cool, and I know that you've invested across a wide range of enterprise plays, is there sort of a Shruti playbook that you find yourself applying to companies after they've joined your portfolio.

Shruti: Yes, so it's the same things we do during diligence which is understanding who their fourth, fifth or 10th customer is and then once we invest we really get them into motion which is helping them think through how they're going to get in front of those customers if they already haven't and helping them with the resources that they need to get there.

Peter: One of the things our portfolio struggles with a lot can be marketing. You know, often the products they're selling are super specific or very niche and figuring out what the right channels are to reach those audiences can be a challenge. How do you go about figuring out what the right forum for these companies to talk about themselves in is?

Shruti: I think marketing on the enterprise level is a little different. Often the marketing that enterprise companies that we invest in is not the Facebook marketing, it's more going in front of the customer, spending the time understanding what they need and so it's more sales, less marketing and then once they do do that then marketing evolves more of creating thought leadership, putting block posts out, distributing it to their customers and potential customers at the right time.

Being on top of mind because enterprise sales cycle are longer and there's a lot more touchpoints required. So that's what marketing really involves but oftentimes marketing is very much, "hey, here's a customer and here's our product is used by this customer." And so it's developing case studies and as I said, more thought leadership. It's different than like a consumer marketing so that's how we help them think through that.

Peter: And do you help them distribute this content?

Shruti: No, that's not what we do. We have firms we work closely with but we don't distribute the content for them.

Peter: Earlier you sort of offhandedly mentioned Array's like workshops and seminars and I was sort of taken aback because I figured it was a one person shop, you'd just be spending all your time working with companies and have very little bandwidth to actually produce stuff. What are some of the things that you produce for your companies?

Shruti:

We don't produce anything for our companies but what we put together is workshops around solving problems.

So if a company is looking to solve problems around how I do hire my first sales executive or you know if there's something in the SMB market but they need to figure out how does an enterprise sales cycle look. Or what does PR look like now that I'm a little mature or do I spend more on marketing or do I spend more on sales so we get industry experts.

We had a marketing workshop with VP Engineering who was ex VP Engineering of HubSpot so we have folks like that who come in, really talk to our companies and really give coaching in a small, one to many forum so that's the workshops and then we also connect them one on one with the right folks at the right time when needed.

Peter: Do you publish any of this stuff?

Shruti: We try to when we can but oftentimes it's also very, you know if you want real help, you have to be more open to sharing your dirty laundry and you're not going to do that if it's being recorded at the early stages. So the founders are not comfortable with that so we really take our time to figure out.

I know this is a market where everything is about sharing and the more you share and the more PR that's out there, there is more attention you get but we've solved for that by creating thought leadership around podcasts we put out there or blog posts we put that out there, we're very thoughtful of what we put out there which is all around enterprise deep tech.

Peter: You started Array two years ago. What's changed in that time?

Shruti: I would say when I started Array was the the peak of angel investing and I would tell angel investors to not invest because frankly speaking many people should not be doing this unless they want to lose their money. So I think that has kind of corrected itself in a way. Angel investors are investing but they are really from very prolific ones and there's still some trying to figure out to invest in two to five companies and then they retire.

They realize how hard it is, they don't have time and attention to give to the companies and then the ones that have done well end up starting little funds. So that's the shift that I've seen. If they've figured out, if they've done it 10 to 15 times, they end up then starting small funds. But I think pure angel investing unless you're just as tourist angel investors or tourist angel investors that are not from you know, the bay area are diminishing in some ways.

Peter: What about Array itself? Have you found yourself shifting focus or changing the way that you engage with companies at all?

Shruti: Shifting focus I think the storytelling has shifted a little bit because suddenly AI, the word has gotten so popular and I find myself really not, you know, as an engineer working on data and prediction and automation and all these problems for 17 years now and having a Masters in Computer Science at Columbia, AI is a buzzword that's really bothered me.

So I'll go talk to folks and I say I do deep tech and then they'll be like, so is it AI? And to me that you know, obviously is one aspect of it. So Array generally has evolved in the way that we talk about our story but the focus and what we do with at the front has always been the same which is helping enterprise founders at the early stage with the focus on deep tech.

Peter: You find the term AI distasteful because you think it's not new?

Shruti: It's not new and I think most people don't know what they're talking about.

Peter: Say more about that. What am I getting wrong when I talk about AI?

Shruti: I think it's most people who don't know anything about AI think about it as Hollywood and other people don't know the difference between open source software that enables AI to help you write applications on top of that open source software but they think as an extension they're an AI company which I don't think it's true. And then the third category of founders don't really have access to unique data and really defeats the purpose of currently the kinds of problems AI can solve.

so I think that's where I find people don't really open the hood or under the hood to understand what AI really means and I often find those conversations very frustrating. And I often find when a founder comes and pitches to me that they're an AI company, I don't want to be mean to them but to me I really want a clear definition of what AI means to you and how you're different.

Peter: What are the successful ingredients for maybe we should use the term machine intelligence?

Shruti: I don't think that's that better but yeah.

Peter: Okay, what's the right?

Shruti: I don't think there is a word.

Peter: You think that as a category, it's sort of illusory?

Shruti: Well I think there is you know, smart algorithms, better data, cleaner data, all of those things you can use as solving problems that can enable you to have a specific outcome. But in terms of AI as a company, I don't know that that means.

If you say you're an AI company I don't know what you're really doing. Array tends to think about this from the perspective of what are you solving for and exactly why are you technically different?

Just start there, right and so you know, when we invest in AI, we solve for problems like fraud detection, we solve for problems like plumbing, cleaning data. Half the data finders don't want to touch dirty data. If you don't have clean data to work with you're going to have no AI basically. So that's one of my companies Open Price solves that problem. One of my companies Simility solves a fraud detection problem with machine learning so that's how I look at AI and the kinds of problems the companies are solving and then their access to create or use data uniquely.

Peter: Can you tell me more about Open Price? You said that Open Price is involved in cleaning data and the plumbing of a data pipeline or data infrastructure. What are they doing?

Shruti: You know we call it garbage in, garbage out which is if you're creating bad entries in a sales force of a market or HubSpot or whatever any of these databases. And if you want to access that data today, marketers are afraid. You know people are spending thousands of dollars on legend but they all have these leads right within their own databases that they don't know how to access.

So this company solves simple problem of enabling you to use your own data for whatever problem you're trying to solve by cleaning it up and normalizing it and deduping in anything you need in terms of plumbing and you won't even know it's doing its job in the back and so we call it new MuleSoft with better workflow integration, things as such.

Peter: What did you like about the company?

Shruti: The founder, the problem it's solving and I could easily see how the company would grow from no revenue or very little revenue to you know, a million plus in 12 months and they have really surpassed it, they've been growing, they've been tripling their revenue every quarter.

Peter: You've talked a little bit about how important a path to revenue is for you and the diligence you do around how much companies can sell their products for. I'd love to hear more about what you look for in founders.

Shruti: So I look for hustle. I look for something that the founder has a chip on the shoulder to prove something. I often find that people who are not given the chance all their life tend to be that personality so that funny enough ends up being a lot of women, minorities, immigrants. So I funny enough I'm all of the above. I think when you're not given the right platform, you want to prove something so first time founders tend to be that.

I know people have in the industry talk about second time founders and I love serial entrepreneurs as well but the hustle has to continue to stay. They always have to prove something to the world, to themselves, to their team and they're you know, good team builders and they have a very clear thought on where the world's going to be two years from now, five years from now, 10 years from now.

Peter: How do you test for hustle when you're talking.

Shruti: I don't test for anything, it's a conversation. I think it's more, I mean when you meet me, you know I'm a hustler. It's not something you asked me for, it's as simple as that. It's knowing the personality and knowing again, there is a difference between a hustler and someone who's just persistent and not willing to give up and not changing their hypothesis and not taking feedback.

So just sticking with their initial point of view and just sticking with that which there's a difference, so to me there's a minor difference between those people or hustlers who say, "alright, I got it," and they finish your sentence before you finish yours and from there on say, "okay, here's how I've changed my point of view after a conversation."

And they're more agile, they operate on the fly and they create hypothesis and they test it, they have the patience to test it and then they work backwards to say, "this is what we've learned and here's what has worked and hasn't worked." The other thing I've recently kind of created a point of view on is like

These kind of operators have a playbook. They know what's working and not working and they're able to document it.

It's not just something they just create on the fly and then aren't able to articulate it, they are and then they're able to create that playbook for the rest of the company as well so that everyone else can repeat and create that.

Peter: Can you give me an example of a playbook?

Shruti: A playbook is you know, "here's what we did and we spoke with customer X and customer X wanted this kind of features and that's why I've built all these features and here's why I haven't built all these other five features that they wanted and this is, the playbook told me how to pick these five versus the other five." And if I'm now an engineer, product manager, as I'm scaling this, I'm a marketer, this is my true norm that I'm going to use to define how we stay focused.

Peter: Okay so you're looking for agile hustlers, people that are thesis driven but that are also capable of adapting to changing information.

Shruti: Sure, I've not used my thesis from agile workforce to agile hustlers but I like it, let's keep going with it.

Peter: And you're working with them, you like to take board seats so I assume you're really involved.

Shruti: I actually don't take board seats.

Peter: Oh, sorry, you take the lead but you don't take a board seat.

Shruti: Right.

Peter: Oh, why don't you take board seats?

Shruti: That's the paradox we talked about.

When you're a smaller firm you have to scale with automation. I prefer to have coffee meetings more than board meetings.

And you know the founders are available, I'm available to the founders. So is our team and we actually have created a community of founders that can help each other out so we work as a family and operate as a community that you know is stronger by every founder we invest in.

Peter: You mentioned a team, who's the team?

Shruti: We have other folks that are not general partners but help us make all this work.

Peter: Cool, I'm interested in how you filled out the Array team. Like what are you what looking for and operating to do?

Shruti: Actually we have a whole network of folks that are all pretty valuable and so is our team but everyone comes with different expertise. Some folks that are experts in what you call AI and other folks who are experts in DevTools. And other folks who are experts in collaboration tools so it depends, we have a large set of folks who help our companies out.

Peter: I want to go back to this coffee over board meetings. It sounds like you're not voting on formal decisions but you're leveraging a sort of personal relationship with the founder to influence the direction of the company. Is that a fair summary?

Shruti: Sure, I think it also means I'm not waiting every quarter to get an update. We get a monthly update, we talk as needs arise. I don't want to create a barrier between the founders and their needs and waiting till you know, the quarterly updates. So it's more fluid and we want them to think of this as a family that they can reach out to as they need something.

Peter: What are your relationships with other investors like? Other folks that are invested in the companies you work with.

Shruti: Pretty collaborative. In fact that is how you scale the family, we work with a lot of other funds. You know later stage funds or early stage funds and I like funds whose style is very similar to ours which is why I love if we can find ways to work together with Heavybit. And you know understanding the level of involvement that other funds have is very helpful.

Some funds can say we invest and we disappear and that's okay but that's good to know so yeah, it depends on what the founder needs at the time and how we put together is indicative of investors that can be most helpful to the company.

Peter: Cool, okay, so we've talked a lot about what you look for in founders and what you look for in companies. I'd love to hear a little bit more about your own relationship to investing. What do you find exciting about being an investor?

Shruti: Fulfilling people's dreams. I love that because when you're thinking, the moment you decided you're going to quit your job and solve this problem, you're full of ideas and I think often people just need a little nudge and direction.

We at Array, tend to solve that problem of helping you think through and create your wavy path, whatever your path is to accomplish the dreams and the problems you're solving, to help you make that happen. So I don't think I would be doing this if I don't work with smart people and seeing a lot of these founders do this again and again and us being small part of making that happen.

Peter: What's challenging for you?

Shruti: As building a fund?

Peter: Yeah.

Shruti: So building a fund as glamorous as it looks requires many pieces to it which any venture investor I know will joke that if you want to be making money or if you want a little easier life, you shouldn't be a venture capitalist. So it's not particularly challenging as it's many opportunities of where you go and start a fund that's different enough in the market where founders want to work with you.

So keeping and staying relevant there is the most exciting thing but also it requires a lot of work to you know, entice a founder to take your capital over someone else's capital.

Peter: You're not the first person on this podcast who said that winning a deal is not trivial and I realize it's a complicated process, there's not a single golden rule for it. What are some things you find helpful in courting founders?

Shruti: Actually we don't have to do anything other than what we're doing today during the diligence like talking through industry expertise, helping founders think through their customers go to market really helps you establish a point of view and a strong expertise and it demonstrates to the founder that you know something more than just another check that's coming through.

So that helps us really win deals in the industry and so there are few founders that we've not been able to invest in just because of other reasons which is the round dynamics and capital, minimum capital required, you know all of those other things, that's the reason otherwise it's usually what we do so there's no different thing we have to do which is awesome.

Peter: I've heard a handful of venture capitalists say that they find themselves struggling to compete against what they think of as dumb money. Like I'm a real expert in this space and I just can't compete against this enormous but sort of uneducated fund. Is that an obstacle for you?

Shruti: Maybe it's a space we're playing in and we're the only money in the round but if there is a decision that the founder has to make between dumb money if you want to call it or tourist money or retail money, I would say more people who don't know the industry well versus you, we tend to win those sales pretty easily.

Peter: Why do you think that is?

Shruti: I mean we invest in founders that are not consumer founders, they're not looking for valuation. They're looking to solve big problems and they know that this journey's hard so founders tend to be humble because they know it's not easy to get a six figure contract from a Sales Force or Google or whoever.

And any help that they can get there will get them across the finish line and so working with a fund that has demonstrated that they can help them do that is more valuable than just getting any money. That's basically how we win deals.

Peter: So I end all of these the same way which is to ask you what you wish you knew going into this? What advice would you have for someone who's just starting out?

Shruti: I mean how long it takes. You know, you think that you'll do some of these things right and things will happen overnight and it's not again, not a consumer company where you can spend a bunch and get more users, it's actually you have to grind it out and every big enterprise contract is just a few days away. And you blink and suddenly a couple years are gone and you still think that it's a good business but there is no true market validation you've received.

And you know I often find it's very hard to really think through what you're building and are you getting the right momentum to keep going and the same thing is true for a fund. So I would say that it's a long journey but

You have to constantly revaluate if you are needed in the market. With the next new fund being started, are you still relevant and why does a founder need your capital over someone else's?

And how can you return 10x plus for your investors because that's also very important.

Peter: Shruti, thank you so much for joining us.

Shruti: Thanks so much for having me here.

Peter: It's been a real pleasure. Where can our listeners find you?

Shruti: We have a podcast called Array. You can find it on iTunes or SoundCloud or wherever your preferred medium to find your podcast. And on Twitter, I am @atshruti. And then we also put a lot of content out there on medium Linkedin and other places so follow us and yeah, we'd love to have a conversation with you virtually.

Peter: Especially if you're involved in smart contracts and fraud detection.

Shruti: Yes and anything nerdy, technical, geeky.

Peter: Thanks so much Shruti.

Shruti: Thanks for having me.