Fund-Build-Scale / Fund-Build-Scale

Fund/Build/Scale: Evergreen Advice from Two Iconic Founders (Transcript)

Here is the full transcript of the conversation between Fund/Build/Scale podcast host Walter Thompson and Dheeraj Pandey, CEO and Co-founder of DevRev, & Manish Chandra, CEO and Co-founder of Poshmark.

Walter Thompson

The average failure rate for a tech startup is 90%. Around one-fifth of them will flame out in their first year, but most of the ones that make it past that mark will never be acquired or go public. It’s brutal.

Manish Chandra

I think the worst feeling in the world as an entrepreneur is that you’re all alone, and the answer to that is that you’re not alone. There’s many people going through that same journey, many people who are on that same path. And by thinking that you’re part of a whole system, you can actually start to overcome some of the mental challenges.

Dheeraj Pandey

I think finding people who have hunger and humility together, like fierce resolve and humility, has always been hard, because, you know, these are paradoxical values, fierce resolve and humility. I think it was a great challenge and an opportunity to find people who actually had both.

Walter Thompson

That was Poshmark CEO Manish Chandra and Dheeraj Pandey, CEO of DevRev. Poshmark is a pure consumer play, and DevRev sells enterprise software, but because Dheeraj and Manish are repeat founders who’ve taken startups from Day Zero to IPOs, they were an excellent choice for the final episode of season 1.

They shared some of the strategies they’ve developed over time for recruiting, fostering early adopters, driving growth, and transitioning across industries. Manish and Dheeraj also unpacked some of the strategic decisions that propelled their companies forward and spoke openly about some of the mental and emotional challenges they faced along the way.

I’m Walter Thompson. This is Fund/Build/Scale.

I’m here today at Mayfield in Palo Alto, and I’m talking with Poshmark CEO Manish Chandra and DevRev CEO Dheeraj Pandey. Thanks very much for both of you being here today, I appreciate it.

Manish Chandra

Thank you for having us.

Walter Thompson

So the topic today we’re talking about enduring strategies for inception-stage founders and investors. From your perspective, you’re both repeat founders, multiple founders, what was the biggest problem for you? Beyond getting funding? What was the biggest kind of curveball, I suppose, when you started your journey?

Dheeraj Pandey 

I guess the hardest thing was to really find the innovators and the early adopters who are a rebel with a cause, who are not having the conventional wisdom saying, “Don’t do it.” It’s like the San Francisco Golden Gate Bridge. You know, most people said, “It should not be built, and it will never be built.” And you find 80-90% of the people to be like that. “Oh, it’s been done before, or there’s already so much incumbency.” So finding this 10-15% of the people who are these folks who want to get promoted, want to do things differently, who do not accept the tyranny of the status quo. I think those are the people that you need to listen to, because if you try to average it across across 100 such interviews, you’ll probably start to really muffle the voices of this 10 or 15 in the minority that you need initially to adopt a product. I think trying to be all things to all people is the toughest thing to actually shun, because you need to be all things to this small set of people, the innovators and the early adopters, who basically have been saying that, look, I don’t believe in the status quo. I think that’s the thing that I had to take away in my first company, because at Nutanix, most people early on said, in 2010, 2011: “Don’t do this, because you’re trying to bring two things together.” There’s a life cycle of the first thing and life cycle of the second thing. And talking to very large companies early on, because they’re paid to mitigate risks. They’re not paid to take risks, you know, and the fear of messing up is way bigger in these companies than the fear of missing out, which is actually true for this 10-15%, so getting that right was probably the hardest thing.

Walter Thompson

Manish, what was it for you? What was your biggest, most dangerous attachment?

Manish Chandra

I was transitioning industries, so I’d been in enterprise software when I started my first company, Kaboodle, and the idea that I had was in the consumer space. So for many months, I just kept saying, “I’m not the right guy to do this idea,” because I had no consumer background. So for me, I was trying to build a team for a consumer industry, trying to surround myself with people who understood the consumer business. And this was 2003, 2004, so consumer as a space in Silicon Valley was very embryonic overall, and, you know, putting together the right team, etc. And even when we first started the company, the people who signed up were all enterprise, and we actually left a portion of the equity to recruit a consumer person, because a lot of the consumer people I had recruited early on didn’t believe in the idea and didn’t believe that this would actually succeed. So I think finally, the guy who came in, who was the consumer person, was someone I recruited through cold calls on LinkedIn, and we were sitting in Silicon Valley in Santa Clara, California. And this first guy joined me from Utah, Provo, Utah. And for the first many, many, first couple of years, he would commute from Utah every week and go back to his family because he wanted to be with family. And it was kind of an interesting experience, because it’s very hard to get believers early on, especially if you’re not considered to be absolutely the expert and the smartest person in it. But we ended up creating something which became, you know, in the early days, had a cult following with the consumers.

Walter Thompson

So let’s get into that. Because I think team building is the first step, one of the first steps, so to me, you know, if you’re, I’ve been one of the first employees in many startups. And the analogy I would use, it’s kind of like you’re looking for people who are willing to get into a very small rowboat with you and then row away from land into deep water. How do you get top talent to quit something safe and take a risk on your crazy idea? What were the tactics you used?

Manish Chandra

For me? You know, I started by volunteering with local organizations. There’s an organization called TiE, which is focused on the South Asian entrepreneurship community. I started to volunteer there. I saw that they didn’t have a focus back in 2002 and 2003 in the consumer space. So I created a consumer special interest group, and then just had the courage to go talk to some of the more interesting people at that time in the consumer space. You know, people that we know now as very, very like household names, but at that time, they were still emerging, people like Reid Hoffman, James Currier, and I recruited them into a special interest group and started to sort of get myself immersed into the world of consumer. Put together a consumer conference, and so that was sort of part of the thing. And one of the best pieces of advice I had was in terms of transitioning from enterprise to consumer business was enterprise business is a lot about productivity. It’s about, how do you do something faster, better, easier? Consumer is about emotion. Reed talks about, you know, the seven cardinal sins and how consumers think. That was a big mental shift for me, especially coming from India and sort of not necessarily being, you know, completely immersed in the pop culture. That was another thing I had to do in terms of transitioning my landscape. But the early team you know that I recruited actually came from some of the personal networks I had. In fact, one of my co-founders I recruited, I met him at my daughter’s preschool, somebody I had worked with before, and said, “Hey, come on over.” And then rest is history. Now we have founded two companies together.

Dheeraj Pandey

I think finding people who have hunger and humility together, like fierce resolve and humility, has always been hard, because, you know, these are paradoxical values, fierce resolve and humility. I think it was a great challenge and an opportunity to find people who actually had both. Because on one hand, you do want people who are convicted, who, like, really have a level of conviction. And if they don’t, they have a sense of focus about the micro things they do that can actually affect a company, rather than worrying too much about the rejections that you get early on, because there’s so many rejections. And that’s nature’s way of saying, “Look, if you really believe in your idea, you have to walk on fire with 98% no’s before you get two yeses.” So finding those people who are not, you know, basically wayward in the way they think, and the fact that they have to manage their emotions every day. It’s interesting. The word Manish used also about emotions. I think it’s finding people who actually bring a level of emotional stability where the craft matters a lot, because if they care for the craft, they’ll not worry about a lot of these rejections early on. And if they can find the endorphins and the dopamine in the craft, they know that this is the way to change the world. I think finding those people is the hardest thing. And then going on walks. I remember I would go on walks with a lot of people because, you know, it’s like now that you’ve shaken hands and their employees with you and and they’re like, “Wow, we’re getting all these rejections. What do we do about it?” Normalizing those rejections, knowing that that is the test that the world is giving you, because most people flail and they give up. They’re like: it looks like it’s not worth it. You know that, to me, is the toughest test of entrepreneurship, where you know, the world is pushing and you’re pushing back. You know, we talked about iron sharpening iron, the world is that iron that’s really pushing back on you. And unless you really use that to actually think better, design, better, reduce friction. I mean, simplify your messaging. Find the .11% of the market that you have to go after, as opposed to being all things to all people. I think finding those people is the hardest thing.

Walter Thompson

But for both of you, how hard would you work to recruit someone who seems skeptical around the fence? What do you want? Do you want people who are ready and really get it? Or are you willing to hire someone who needs work, as far as being convinced of your vision?

Manish Chandra

I think you have to do both. You have to do both, but you have to be able to have those authentic conversations. So if somebody is just not listening to you and is skeptical, that’s one thing, but if somebody is listening to you and is skeptical, that’s another thing. So, you know, we’re talking about this guy who I recruited from Utah. You know, he took interest. He read our documents, and he said, you know, we did have that much money in the company. He said, “I’m going to fly on my own dime, right? But I don’t know if I can join you guys,” right? He comes in, the three of us who had co-founded the company are sitting, and he walks in, and the first thing he goes is “Guys, you know, I just have to say one thing: that if you by default, keep all your pages” — which was sort of the core unit — “private, I’m just leaving, I’m taking the flight back, but you have to make them public.” I’m like, “Who’s this guy who first comes in and completely wants to change our product strategy?” But that was a very authentic comment, because that’s what he felt. And it ended up becoming a very endearing comment. And we had a pretty major discussion, but he was very skeptical about how we were thinking about the product. And he was right. We had to shift. We didn’t know it. And so I feel like if you can have that genuine conversation with the person, it’s very powerful just building on that. You know, as we were recruiting and three of us were about to take this journey together, one of the things I asked the co-founders, I said, “You know, we’re about to take this journey. We don’t know if we’ll get funded. We don’t know how long we’ll have to do this without funding. Let’s share our bank balances. Let’s figure out what our bank balances are, what our monthly burden is, so we know how long we can be on this journey together.” And it was a little awkward early on, because, you know, we were professionals and all of that. But by doing that, we were able to create that commitment. We were lucky. We got, you know, some level of funding in the first six months, but could have taken a year, and we sort of said, “let’s commit to a year, you know, 9-10, months, we can start to look for a job.” But we needed that commitment, and so we needed, you know, some level of resources to be able to do that. And that awkwardness led to a level of authenticity which allowed us to partner for a long time together.

Walter Thompson

That sounds almost like a trust exercise.

Manish Chandra

Yes, yes, very much so.

Dheeraj Pandey

So yeah. I mean this idea of a funnel where you’re actually getting this initial skepticism and how every day, every before even they sign up, because I think it’s a great exercise. It’s like they need to learn from you, and you need to learn from them as well. But along the way, you don’t need people who are flip-flopping, because what happens is, after they’ve signed up, there’s many people who can’t keep that “one step forward, two step backwards” kind of emotion look, I think building a startup is a mental game more than anything else, and if you find people who are willing to be at war in this, you know, underserved market, they need to actually bring the same level of commitment. And when I say commitment, commitment to their own emotions, more than commitment to the company, that if this has to be done, it is us, and if you have to spend a lot of energy and time on them. I think, as I said, you know, in the initial months of maybe weeks and months of an early employee, they’re like, probably like, “Wow, did I do the right thing?” So you got to spend time with these people. They’re also your customers. You know, it’s not just your end customers. These are also people. And you know that if you did this right, even if it slows you down a little bit early on. But if you did this right, you found more apostles who can actually go do this. It’s the perfect thing to actually commit to in terms of time as well.

Walter Thompson

Is it fair to say that the early recruiting process actually helps you, or helped you refine your value proposition? Because you were kind of trying to prove it over and over again to people you’re trying to attract?

Dheeraj Pandey

Absolutely and, by the way, you’re listening to yourself. Because, I mean, I do this a lot. Personally, when I listen to myself, I know if I’m BSing, or is this authentic? And along the way, it forces us to think about the real user, the real buyer. Because, you know, you can think of a customer. There’s no one customer, right? There’s like, so many segments of the customer within the market segment, you actually have different buyers, and then their users, and the different kinds of users, they’re lurkers, they’re consumers, the producers. There’s so many ways to actually skin this, you know. So listening to yourself will definitely help as well.

Manish Chandra

And the ability to sell, right? The idea in the early days is part of the journey of you as an entrepreneur, of refining it so convincing these co-founders and the early employees is very key. And you have to as D is saying, you have to listen to yourself. You refine that, but you have refined and get that clear. And I was reading somewhere in an article that Gokul [Rajaram] had written where he said, you know, the failure to recruit a team is often the fact that the entrepreneur doesn’t have a clear vision yet of their business. And so that process of refinement is very critical. And I think, you know, you can do it in different ways. I call it this process of “kitchen sink cabinet formation,” where you’re getting people, you’re refining the idea. And people are not yet convinced. They’re just participating a little bit, but as you build that conviction, they can really start to jump in. And it’s almost like then they become the evangelist for you, and you know, and then it sort of propagates, and it changes, it evolves, but it cannot stay too far away in the early days, which means you have to have that crisper and crisper over time. And sometimes, if you don’t have it, and you’re having trouble attracting it, sometimes you think, you know, “I don’t have the network. I don’t have this.” But I always believe that the thing you can do is work on yourself. So you could work on that vision, you can work on that speech, you can work on that sales pitch, and that’s how you get the people coming together.

Dheeraj Pandey

And by the way, it’s a real tightrope walk, because if you try. To show too much resolve and not enough humility, then people are like, “Well, then where is my voice?”

Walter Thompson

I call this “CEO syndrome,” with the great leader pointing off into the distance.

Dheeraj Pandey

And what people are looking for, I use this analogy of tropical fruits. You know, they’re hard at the core, but they’re flexible at the periphery. What does it mean for people to see the two sides of you? Because that no is a currency when you say no, we’ve got to be on this path. You know, it’s not like we can just go veer away simply because we heard one person say this. So how you use the nos and how you actually be flexible at the periphery with, you know, with your own people as you listen to them is the only way you can retain them as well.

Walter Thompson

Let’s shift gears a little bit and talk about value proposition and kind of developing your unique offering. Manish, if you can go first, what was the specific moment or key insight that helped you realize that Poshmark was the right company for the right moment?

Manish Chandra

It was probably a series of three things that happened. One was, you know, in 2010 when I was thinking about what to do, I knew I’d come from building a company. You know, the company got acquired, and it was in the fashion space. But it was sort of an accidental journey to get into fashion. But once I was in that space, I realized there’s many unsolved problems, and I wanted to sort of solve something there. So that was sort of the macro thing. And I was starting to recruit a team that understood fashion, understood technology, so that was sort of the formation of it. But then in September of ‘10, I was on a vacation right here in the Bay Area. And my friend took a photo of a bird on his iPhone 4 device and instantly published it on Facebook. And I was on my SLR camera trying to take this photo of a bird, and it was just, you know, going to be a process of taking the photo, processing it, putting on an SD card, putting in a laptop, uploading it, I said, “This phone is something, you know, crazy.” And so that was the second moment of inspiration. And then started to ideate on how this, this thing, can really transform in terms of the different ideas. The third piece that happened was my school’s my son’s homecoming game, and the homecoming queen in 2010 was wearing this beautiful yellow dress, and we were talking to her mom, and she said, “Well, she thrifted that dress.”  And so a bunch of these things then reconnected. And I said, “We can reinvent how people buy and sell fashion,” and that’s how sort of the pieces came together to start Poshmark. And we bet, the big bet we made was, is going to be social, is going to be something that any at that time, any woman, any girl, can use, and it’s going to be 100% on mobile. That 100% on a mobile was a big bet, you know, challenging conventional wisdom, but it was sort of one of the right bets that we made at that time.

Walter Thompson

And that’s still the central idea of Poshmark.

Manish Chandra

Yes. Really hasn’t changed that much still.

Walter Thompson

And for you, like, what, what was your kind of inciting moment? When helped you realize it all kind of fell into place that devrev was the right company for the right moment?

Dheeraj Pandey

DevRev is three years old, but my previous company, which I’ve been talking about since 2009 is Nutanix. And I ran Nutanix for 12 years. And then I started DevRev in 2021, January. And I think this idea that, and I was growing with this, you know, this device next to me, which is the Apple iOS, and the fact that we were going after a pretty stodgy market, which is data center software, you know. And this everybody was actually saying how complicated and how fragmented it is and how siloed it is, but nobody had a good answer. I was always a believer that the whole is bigger than the sum of the parts. And by the way, that’s exactly what I’m doing at DevRev as well. I’m trying to be looking at business software and saying it’s completely fragmented and nobody understands the customer nor the product build. So there is a big opportunity to really prove that the whole is bigger than some of the parts. Just so happens that AI helps to converge a lot of these things too. But I think going back to 2010-2011 I think one thing that was happening around us was the emergence of Apple in the consumer space that we’re like, “What can we learn from that to apply to the enterprise space, in a really boring market called data centers, you know? And can we bring software to really converge a lot of these silos into one?” I think, 2012, 2011, 2012, the first two VMWares, you know. So VMware was the larger, like big daddy of software virtualization, and we were actually sitting on top of them as an app, in some sense. And we’re taking big hardware and putting it pure software running on top of VMware. The feedback that we got in the first two conferences, the Best of VMworld Awards, basically told us that we’re doing something right. And then Edward Snowden happened, leaking of a lot of data. And we had found a couple of people in the US federal space who were actually sellers at VMware, but they were sort of disillusioned about the way that company was going, and we had hired them a little bit ahead of time. We didn’t know. But like, “these are great people. We don’t know whether we should go into US federal space right now. I mean, most people are like, “Why would you go into US Fed in 2011-2012?” and we said, “No, no, but these are really good people.” So we became a little opportunistic in hiring them. And then obviously, serendipity happens. You know, the fact that US fed decides that no laptops ever leave the building anymore.

Walter Thompson

So this is a post-Snowden decision?

Dheeraj Pandey

Yes, 2012-2013, this is happening as we speak. They’re like, “All personal computers must stay in the cloud in their own data centers,” in some sense. So now, all of a sudden, the two worlds of a laptop and our data center server are converging, because you’re now streaming a laptop or Windows experience from a data center, as opposed to giving people physical laptops. This idea was called virtual desktops, and we pushed back on the market because VMware and Citrix were trying hard for seven, eight years and real struggles. Most people said, “Look, it’s never going to work. It’s dead on arrival.” A lot of investors said, “iI’s dead on arrival, this idea that you’d stream a laptop experience, a Windows experience, from somewhere else,” but we stuck on to it, a very contrarian viewpoint, because we said, “If the world thinks it’s dead, that there’s something in here,” and most people in 2011 said Windows is dead because iOS is here. And we said, “What about all these enterprise apps? What about Excel? What about PowerPoint? I mean, these are things that are not going away anywhere.” So going against the wind as a way to make money was a pretty important step for us, it was probably high risk. But then when fed became a big vertical for us in 2012-2013 — extremely contrarian to go with US Federal as the first segment, a big segment. It used to be 70-80% of our business in the first two, three years.

Walter Thompson 

But it sounds as though Snowden and WikiLeaks kind of validated your unique selling proposition.

Dheeraj Pandey

Yes.

Walter Thompson

That was why you didn’t need to go out and get a lot of social and market proof. It was kind of like, “Look at this headline!”

Dheeraj Pandey

Yes, absolutely.

Walter Thompson

So Manish, what was it like for you? How did you validate the thesis behind Poshmark for investors, and for yourself?

Manish Chandra

So a few things happened. I think one thing is, we had a certain thesis about how we wanted to build the app, and half of them came true, but half of the tech was not ready. So at that time — this is back in 2010 — we wanted instant background removal, which now is feasible and possible, but at that time, we tried, tried, tried, we couldn’t do it. And so one of the team members said, “Why don’t we just go with whatever background we have? Just do a little, just do a little filter on it.” And that’s how we built the app. In three, four months, we kind of got the first version of the app ready, but there were a couple of problems. Most people didn’t own an iPhone at that time, and our product was built for an iPhone. And the second thing was, if you can believe it, in 2010-2011, people didn’t take photos as often, you know, which is so hard to believe today, because we take photos by the second, the notion of the selfie had not yet been born. And so we had this huge road ahead on how to get people to use the app to create listings. So we came up with this idea of trying to get women — because it’s really focused on women — in the evening, at five o’clock, with five pieces of clothing, to take photos. And we started to do these small physical events that we were working on. And that became a thing. People would come and we would start to work with them. But to do that, we had to actually buy 100 video iPods and hand it to people with preloaded apps because they didn’t have a phone, the phones that they had were not usable, and so we were literally giving out pieces of hardware to people to use, but they started to use it, right? And but the usage was still slow and sort of spotty in the process, and we hadn’t built any of the logistics of the payment process, we were done. Payment processes were done by our community manager who would literally collect cash and then hand out bags to people, kind of like a little, you know, undercover deal that was happening. But that’s sort of how we were testing it out. And then there was some sort of a real-time DJ app that came out where people were being asked to do DJ. I forget what it called. Anyway, people were doing real-time DJ with something else, some turntable.fm, turntable, something like that. I think it was. And so I was looking at and I said, “You know, why not simulate a virtual, real time event in the app?” And that started the notion of our first concept called “posh party.” And what we did was we literally would just announce that at seven o’clock we’ll have a posh party. There’s no software support. Just come list, and the theme would be dresses or hats. And that really started to get the seller activation going by just everyone being there, and being able to shop. It became really easy. And so then we just said, “This is the magical clue, and this is really the product-market fit,” where it can get buyer-seller matching happening in real time. And the only reason it could happen was because a mobile phone, the web guys couldn’t do it, because you’re not going to carry a laptop. But here you could be in a bar, you could be in a restaurant, you could just participate in the party, you know, quickly, share and do all of that. So that was sort of our big moment to see that this was happening. But took another six months to kind of build the product, and because there was no we were building something completely with no real, real world sort of out there. So it took a lot of struggle to build that piece of the app, and then we launched it. And then the first thing we saw was that usage was still small, because, you know, there were no distribution engines, but every user was coming, was spending 15 to 20 minutes in the app, and that gave us a lot of confidence that this product could work. Because one of the things I think about consumer apps is you can buy growth, you can create monetization, but you can’t buy love. You can’t buy engagement. You’ve got to build it inherently. So if you get love and engagement, that’s the foundation of every good consumer app.

Walter Thompson

Did you spend a lot of time doing traditional customer discovery for Poshmark, or did you just start building it?

Manish Chandra

No, we were doing customer discovery all the time. So, you know, we were talking to people in that demographic all the time. So we had recruited an advisor board of people who came from the fashion business. We were talking to fashion students. We were talking to thrifters. So this had started even before we, you know, formed the full team. So Tracy and I, Tracy is my co-founder. We were talking to these folks, and then we recruited Leanne, who’s our Head of Community. We were talking constantly, you know, to the folks. Part of it was that we went to fashion wholesale shows, retail shows, etc. And part of the thing was that what we were trying to do was not that it wasn’t happening in the industry, but the velocity and how we wanted to do it was not something that anybody believed. And second thing was we wanted to do it where items would ship directly from one consumer to the other without us touching and so to ensure quality, to ensure fit, to ensure sizing, there was a lot of disbelief that people would actually do that right. And a lot of people wanted to touch the items, process it. So for high-end items, it was happening, and our goal was that most people don’t have a lot of high-end items. They have day-to-day items. So how do you take this same value prop and take it to day-to-day so that whatever you’re wearing becomes sellable? And all of those things were really challenging, sort of many of the processes. And we also wanted to build a shipping system that was not done before, so that was another thing we had to hack and work through. So the discovery process had started literally in ‘10 and continues even, you know, ‘til today, talking to the customers all the time. But the belief that this could work was very much entrenched. So, you know, I think what Dheeraj was talking about, the fact that you’d got to have faith, that faith was there is a shared sort of value product between the four or five of us.

Walter Thompson

Actually, this is a question for both of you. Dheeraj, I’ll ask you first in DevRev and also for Nutanix, how much should you invest in developing customer personas? I hear that it’s a basic tenet that a lot of companies go through, and some companies even invest a lot of money and doing the research and doing it kind of a bottom-up approach. But how did you, how did you approach that?

Dheeraj Pandey

So I think the key thing that we were talking to a VMware administrator, they were the have-nots. You know, “we said we got to take something to the have-nots.” What was that thing? It was data. Now, they never managed data. They were managing servers and virtual machines. I mean stateless things, the things that didn’t have gravity, which was data. Data was being managed by, you know, those folks on the other side who were big honking hardware, five-year purchase cycles, and there was a lot of bureaucracy around shelling out storage and data. So these have-nots, the people who wanted to work at a different speed, needed to really take control of things in their own hands. And that’s what Nutanix really became, that look, when you buy servers, you get to manage data in as reliable, highly available, high performance a way as what you’ve actually seen from these big boxes that these legacy companies have been selling proprietary hardware, we are bringing you a Google-like architecture, Amazon-like architecture, Facebook-like architecture. The way consumer clouds will build is the way you can help build this. And you can start small and pay as you grow. So the persona that we picked was basically not the traditional data persona. We went after the persona that was the consumer of that data, which is application folks and virtualization folks and people who really manage servers, you know. And we spent a lot of time with them. We made them into heroes. We would not talk to the other side, if anything, we made the other thing look like an enemy. It’s very childish, but we used to put a crosshair and, you know, we call it the SAN [storage area network], and we’d have bullets all over it, because SAN was this, this, you know, thing from 20-25 years of mainframe, like thinking where storage was actually managed and data was kept, and we said, “You know, you just get rid of it.” And it was a very contrarian view as well, because people were like, “What do you mean? You get rid of the SAN. Where would I keep the data, then?” And that was a great conversation structure. It’s like the way Salesforce did in the early 2000s: no software. Like, what do you mean? No software. Well, this software, but we manage it for you. And the same thing happened in the data as well. We said, “You don’t need that SAN. That SAN is a multi-million dollar purchase. You got to provision it for five years. You don’t even use it for the first three years. How will you ever bring this level of velocity that you need as you go and really virtualize?” So this idea of no SAN was very, very helpful to us, because people leaned in and said, “I don’t know what you mean by that.” It’s the thing that [Nassim Nicholas Taleb] actually talks about is like, when you say something which is that provocative, a lot of people lean in, especially if it’s done in an authentic way. People lean in and say, “What do you mean by that?” And that used to be a great conversation structure for us.

Walter Thompson

For you, Manish, how important were personas in early development?

Manish Chandra

It was really important. But it was like that we were doing it in a very mathematical, systematic way. It was a pretty clear sort of focus for us. So we, you know, we said we wanted to help solve the problem for this 20- to 22-year-old girl who’s sitting in a dorm, coming out of a wedding, you know. So we had all these, you know, even today, we use that. We call it a dream day, you know, a day in the life of our customer. And we sort of visualize it. And as part of every product spec, every business spec, you know what’s happening? So Judy’s coming out of a wedding, and she’s got this dress, and how does she sell it? And we really wanted to make it fun for her, because we said, you know, one of our core philosophies is, over long term, love sustains. Money doesn’t. So if you’re just about money, it’s going to be hard to sustain, but has to be something that’s fun and joyful. So a lot of the focus for the customer was, how do you make it super simple, so that Julie is not being troubled, but at the same time, make it fun and easy. So we made several decisions. You know, Julie would not have to decide how to ship it. No matter what package she’s shipping, she can ship it using our simple system, which we do. She has to ship it herself, but she gets the whole system in her thing. She doesn’t have to onboard as a seller. So she’s just there. She’s just selling some clothes. It’s not a big deal. And the third thing is, make it so that she just receives positive validation on that. So in fact, for the first seven years of the company, or six years of the company, we didn’t even have product reviews. There were no reviews, which, you know, think of a marketplace. There’s no reviews. So we challenged many of these things in service of that customer persona, and we deliberately avoided going after places where people were already reselling or thrifting, and really went to places where people had never done this before and daft into an untapped market of people who wanted to discover the joy of fashion but didn’t want to think of themselves as resellers etc, out there, and unlocked a whole generation that was ready to sign on and do this in a simple and fun way.

Dheeraj Pandey

I will say that in the last 10 years and since Nutanix, I think at DevRev we do see a more evolved design thinking that has gone on in the enterprise space. We are going after Salesforce and Zendesk and all these support companies and CRM companies and so on. I feel like design forces you to also think hard about personas. That was not there 10-15 years ago. Design was supposed to be in the domain of what Manish was doing at Poshmark, but not probably as much in the enterprise space. We were probably one of the earliest companies 10-12 years ago to say, look, design is how we lead, and simplicity is how we’ll sell. We didn’t have all the bells and whistles of what neither the big storage guys had, or what VMware had, but it was so simple that the have-nots loved it. And I feel like in the last three years at DevRev, we’re seeing more and more of it. Today, we just made an announcement. We are getting one of the top shots at Airbnb to come and head design for us. And if anything, I think that’s been my biggest journey in this last 15 years of entrepreneurship, is: Do I understand what less equals better means? And it’s a struggle of a lifetime. And for all entrepreneurs, I’m sure. So Manish can talk about that too, but the idea that doing fewer things but better, and now with AI, you have to co convince the end user they should do fewer things but better, because they have to also let go of things that they thought they were good at, that machines can now do the chores the bottom the pyramid stuff. I think personas are getting more and more evolved. And if anything, in the last 9-12 months of the buzz of AI, I feel like we are again, the Silicon Valley way of saying, the agents, agents, agents. There’s many agents everywhere that is an interesting persona as well that’s emerging. Like, how do chatbots behave? And how do you really put them next to people who are human agents? So human agents and AI agents have talked to each other is going to be a fascinating journey in design.

Walter Thompson 

The things you’re both talking about just made me think about how much early-stage CEOs must be focused on removing friction from every process. And whose job is that really, is that your job as CEO, or is it, it’s everyone’s job? But who really owns that? I suppose. Dheeraj, you —

Dheeraj Pandey 

Yeah, I mean, because on the inside, you want to make sure that people, I mean, you formed, you storm now you have to norm and perform. You know, I think this idea of going to form and storm is enough friction in it. “Norm and perform” means that the enemy is outside. You know, we can’t have this enemy within about, “So what do I own, and what’s my overall fiefdom,” which people start to really talk about over time? I think reducing friction in the inside is very important, but also on the outside, I think with the end users, for them to feel like they have been, you know, really given something that gives them something which is 10x faster, or, you know, they can do things with you take a week that can be done in an hour, or something like that. It’s very, very important, and it’s such an iterative process. I mean, you can get bored of this, but to chisel, chisel, chisel, chisel, chisel, and at the same time to deliver a new piece of software, especially in the last five, seven years, of delivering this to the cloud in a way that has actually some level of paradox built. And if you change too often, they’re like, “You’re changing too fast.” I just learned this thing in the last three months, and now you’re saying you ought to change this whole thing at the same time, you’ve got to give them something new that has less friction is, I would say, a big challenge and an opportunity.

Manish Chandra

I think another way to think about friction is, how intimate are you with everything that’s happening, and how intimate are you with the customer, sort of removing intermediation in different things and getting more and more people exposed to each other and to the consumer and to the customer? And in our case, you know, it happened a little bit organically, because one of the ways which we grew, and we still do a lot of them, we used to do physical events. So kind of like almost the opposite of the world we went to a few years back and was coming back, we would actually have customers come to our offices, and we would have events literally every week. So every week, you had an opportunity to talk to customers of your product and I think there’s just so much you learn when you’re actually talking to the customers and sitting side by side with them, and evolve. And even the persona growth, you know, where you’re going from a young woman to a different kind of a demographic, different backgrounds, different sort of needs. And our whole company was able to participate in it. So it wasn’t just, you know, one or two people, or just the community people, or just the CEO, engineers, technologists, you know, operations people were all sort of in that process, and even today, we try to do that as broadly as possible for that exposure. So you kind of have this real, physical vision of the person you’re serving, and physicality of what you’re doing and being a consumer product. Many of the people were actually users of the product as well. But sometimes when you’re yourself using it, you can have biases. But when you talk to 10 customers, you can remove that bias and look at, you know, not necessarily different personas, but different perspectives on that sort of problem. So I think that is very critical in the early days, that people have a shared sense of the customer as much as they are interested and they can, and if it’s a consumer product, it’s a little bit easier to sort of visualize, you know, how people are using it and what they’re using it for. The other thing, which is there is that very early on, you know, there’s not that much bureaucracy because you’re working through it, but as you get a little bit bigger, bureaucracy can keep up very quickly. So sort of thinking through how you disintermediate that bureaucracy, which is a form of removing friction. It’s very much there. The opposite side of it is, if you have no processes, the chaos can also cause friction. So starting to put some level of process and systems is critical at each stage. And then, of course, as you scale up, you have to do more things. There’s more compliance required, more other things required. But that process and thought of friction sort of permeates at every stage of growth, the harder problem in my mind is this disintermediation of intimacy with customers, intimacy with business problems — that gets harder as you scale. And keeping that in mind is really critical, because you start to get caught up in a lot of second-order problems, whereas, if you simplify, you can actually scale faster.

Dheeraj Pandey

By the way, the only job of a CEO over time is to go towards the fire. There’s a really good article The New York Times came up with, like, maybe five years ago, how to be a CEO by talking to 300 of them, and they said, “Look, they’re all obviously there’s a big diversity in the way these CEOs actually had grown and done their jobs well. But there’s three things that emerge. You know, one of them, one of the traits was they were very curious. They wanted to not just know the what, but the why and the how. Second was, they would actually go towards the fire.” So they would actually say, “Look, it’s my job to go towards the fire, which is akin to friction in some sense. How do you really go and embrace it and say, This is my problem.” As opposed to most people who run away from it because they want to avoid friction. And the third thing, of course, it also talked about how they did their current jobs rather than trying to aim for the next one, they did the current jobs really well. And in many ways the reverse psychology the world said, you deserve the next one. They’re like, “No, no, I don’t know if I do,” but the idea of really embracing fire as your problem is a very important one for entrepreneurs at large.

Walter Thompson

For both of you. I mean, at this stage, Poshmark is about 14 years in. Do you still take things to the product team and say, “I’m not sure about this,” or “I think this could be better?” Or are you not? Are you not that involved?

Manish Chandra

I do, unfortunately, to their chagrin, sometimes, but absolutely, I think, I think if you, if you stop thinking about the details, it’s there, you know, just to give you a sense, for the first year I was in the frontline customer support. You know, in the first six months, I answered every single customer service inquiry myself, and I still have a direct line to the customers who can contact me. It’s much less now that it was very little, and there’s a process around it and stuff like that. But I think not being able to look at the product and in detail, I feel like it’s an important thing. The second thing is, I think I have it. And I think a lot of I’d say every CEO, you have a direct line to many of your customers, right? So sometimes I’ll find that the site has a problem because some customer contacted me through Instagram, through text messages, through email, through something before my team sometimes knows it, and that, I think, is just the ability to keep connected. And when you start to feel very disconnected from your customer, that’s probably time for you to get somebody else to do your job.

Dheeraj Pandey

And honestly, this is your currency as well, because at some level, your developers, your designers, your product managers, they also want to feel like the founder, the entrepreneur, the CEO, actually cares for what I do. And it’s if you stop speaking that language, now you’re too high level. Now you have a corner office. Now you’re like, hey, it’s all about customer centricity. You know, we came up with this really good white paper, the essential methodology, and it basically talks about three pillars. Like most things in life, Power of Three: one is obviously being customer-centric. A lot of entrepreneurs, as they grow, they’re like, “oh, I just need to spend more time on the road and be more customer-centric.” But customers are talking about product too, so you’ve got to know about what’s happening in the product. So the second pillar is being product-led. You know, what does it mean to be product-led. Third, obviously, I think in the last three years, maybe two years more, so is being AI-native. What does it mean to not just AI-washed, but really get deeper into it? But product-led is as important as being customer centric. There are two sides of the same coin.

Walter Thompson

Marketing and branding in the very early stages: I know now you’ve got, you know, rigorous infrastructure for this, but at the very earliest stages, it’s kind of on you as a CEO/founder, to kind of articulate that, you know, here’s who we are. I think of it as, like, you know, the movie has, like, a log line at the bottom of the poster, kind of, that’s, that’s your job, but that’s pressure. And I don’t think most people are natural storytellers. So for each of you: do you think of yourself as a natural storyteller, and if not, how did you work that muscle, develop it?

Dheeraj Pandey

So I was always a history buff, and I have a really good memory recall, like I like in my brain. I don’t know how I put this, but it’s in shelves in decades and years and months. I know exactly what happened where. So there’s a visual thing that I have, and it helps me tell good stories. And I can do this in an instant, like this New York Times article, I just came up. I didn’t even remember it. I just came up in my head, so knowing your history well really helps. Yesterday, I was talking to somebody, and I brought in The Rise of the Ottomans from Netflix. Like, “Oh, we’ve got to talk about how Constantinople was taken,” you know, so it was focused and conviction and all this stuff. So history is good for founders too. I think it’s just a great way to tell stories from different walks of life. Bringing into company building is a way to say, look, if it happened there, it has to happen here. Eventually it is a war. You know, we are waging a war against incumbency in an underserved market. You know, on behalf of an underserved customer, and in some sense, so that, to me, has really given me the ability to really go and not just talk tech, tech, tech, and not just personas and users, but also life. Life is as important that you learn from Apple, you learn from Google. You learn from everything else around you as well. You learn from your children. I think the one thing we did well at Nutanix, but also doing even better at DevRev now, is the fact that you don’t dichotomize product design from the company brand, because it’s like, you know, these two things are fused. In many ways, the product is the heart. But now, as you build the whole body, you need to think about the brand and the character of everything is one. It’s not like, oh, I have a character of the product and I have a character of the company. So having a single design leader who can think about both, and even more so in the last 10 years, because now, even in business software where the website ends and where the product starts, the lines are blurred. You can do a sign up right then and there, especially in freemium products where there’s no need to talk to a salesperson. So it’s really important to think about one brand where the way your product looks and the way your website looks cannot be like it’s two different companies in many ways, you know, I think the tagline has always been a challenge. But, you know, you learn from others too, like, you know, I mean, Steve Jobs talked about this, about creativity. He said, Look, many a time you just have to look at other realms and copy it into your realm, and that is creativity, as opposed to inventing something from scratch. You know, we’ve been trying out this thing about “just don’t do it,” as a way to really enable more AI in whatever you do in your day-to-day life. So let the machine do it, as opposed to so obviously it’s a thing that will probably go away. But what is the consistency of your brand over the course of the next three to five years? I mean, to build an authentic brand which has many things that will keep changing in landing pages and campaigns and all those things that are at the periphery, but at the core, if people can relate with you, like I still relate with simple and even more so now: less, less is better. Hopefully, if you can keep this going, good things will happen.

Walter Thompson 

Fourteen years ago, you weren’t a fashionista as you are today, certainly. So how did you get the confidence to articulate your value proposition to people who were very much in this world when you were outside of it, Manish?

Manish Chandra

I believe leadership is community, right? So for me, a lot of my life is surrounding myself with people who are great, you know? So in this case, it was surrounding myself with Tracy, surrounding myself with Leanne, surrounding myself with people who can educate me and grow me, right? And for me, I’m just naturally very curious about things so that’s sort of one of the things that draws me to this space and fashion is, you know, always changing the other thing which was there is that I’m just curious about wherever I live. So if I live in America, I’m curious about America in California, California, and I also want to constantly rejuvenate my mind. So for example, one of the techniques I use is, you know, if you are a Spotify user, they give you every Friday some new songs that come out this morning, and they rank them. So you know, the first 10 songs are likely very pop culture. They’re probably at the red-hot center of what you like. But if you go to the bottom of their list and start listing from the bottom, you discover something new. And so part of what you know in the world I live in is constantly discovering where the world is, not just where it is, where it’s going, but where it could possibly go, and that has helped us, you know? So if you step back and think about marketing and branding, there are some eternal values that are going to be foundational for us. It is making things simple and fun in terms of buying and selling. But then there are also some things which are very relevant today, right? So, for example, Eclectic Grandpa style didn’t even exist a year back, right? But it’s very, very specific today. So that world is changing, and you have to be connected to it at the same time, people who define a whole culture, generation, who define an iconic sort of direction, are also emerging all the time, you know? And how do you sort of use that power, you sort of where the trends are going, and then combine that. So you have to make marketing very relevant to the current conversation, especially if you’re going to build something that’s an enduring process, and that requires concentrated education. So that is also drawing into people, you know. So how do you surround yourself with people? How do you expose yourself for the right people who can bring that back into that so I was very lucky that in the early days, Tracy Sun, who’s my co-founder, was part of the journey, who was able to articulate things way better than I am right then I was very lucky to have drawn in Leanne, who’s our SVP of community, who came in and just had an authentic sort of sense of where things were going, and using these partners for marketing and branding allowed us to sort of thrive in many ways early on. So I would say whatever you don’t have you can always find it in someone else.

Dheeraj Pandey

I think it also goes back to your question [about] personas a little bit, the idea that you know, who are you marketing to is very important, because you can abstract it so high level that nobody gets the message. Practitioners. What do the practitioners want? Who are these doers? Who are the rebels? And whether you break glass or whether you’re just trying to be sophisticated, I think these are all the things that I at least struggle with, continue to struggle with right now as well. Like, do you know when to break glass because you want the attention, versus when you start talking to sophisticated buyers, they’re like, why are you actually taking all this sort of breaking glass kind of approach when you can do something else?

Walter Thompson

Let’s pivot a bit to fundraising, because I know people are gonna have a lot of questions about that. When is it too early to raise money, Dheeraj?

Dheeraj Pandey

I mean, it’s someone else’s money, if you can do it on your dime, for as long as — until you get the conviction that you can manage someone else’s money, because obviously you have to do returns as well. I didn’t realize this, that there is another stakeholder, which is an invisible stakeholder that you don’t get to see every day, is the LPs [limited partners] of the VCs, and it’s their money. So until you really get ready for that, where you’re like, I have the conviction, I have the fact that I don’t have to go back to them and say, “Oops, I need to change direction in a big, big way.” Because the more and more money you actually raise, the less you can pivot now. It’s a big change. You have to go and really convince a whole lot more people, and it’s not that many of them won’t come with you for this change in direction. But most direction-changing is proportional to the amount of money you raise. You can probably change five degrees and 10 degrees when you have, let’s say, 100 million that you raised, as opposed to 180 degrees. You can change 180 degrees when you have less money that you’ve raised from others you know. So when you know that you have to go towards New York, and yes, I need to, actually, you know, change things a little bit here and there. But it’s five, 7, 10, degrees of micro-pivots along the way. You should keep raising more along the way. And if you feel like you don’t even know whether you should go to New York or to Cancun, you should not raise money.

Manish Chandra

So of course, I agree with what Dheeraj is saying, but let me, let me give a slightly different sort of perspective at the very early on in the process, which will kind of help tie to what Dheeraj was saying. I think in the early days, you’re just, you know, you need the money so you want to be closing, small, big, etc. But there’s a second dimension of money when you actually start to use it, right? And so as you’re getting the money, it doesn’t mean that you have to immediately start to burn through that money. So you should be closing when you get that opportunity. So if I go back to my first company, which was a much harder process, as you go through a second company, it gets a little easier, as we all know, we closed very small amounts of money. A couple of them are from small angels, etc. And when I went to actually close the checks, everyone made their amounts half of what they wanted to. So suddenly the amount shrunk, right? But we closed it, but I told my team that we won’t start payroll till we have this critical mass of money. So we closed it, we put it in the bank. But just waited. Waited, waited, and we were lucky enough to sort of, you know, raise it to a point which we had decided, which was about a million dollars. And we were able to do that, but we didn’t really trigger the true spend till we started to sort of hit that. So that’s the other piece of the system. So I think when we think about, you know, raising money, you got to raise it, whatever and however you can. And I have this phrase, you know, “Beggars are not choosers, and choosers are not beggars.” At some point, when you have choices, that’s great. You can choose whether you want this kind of money, this amount, et cetera. But a lot of times you don’t have choice. You just take what you’re getting. And sometimes you know, it may be that it’s needed to hit the next milestone. The second thing, which is there, is that we are in capital-intensive businesses. I’m assuming many of your listeners are in a place with it’s not going to become quickly profitable. You have to, you know, keep raising. So in that what, what DJ was saying, is very critical that whatever you’re raising, there’s a next race coming, and you got to hit that milestone. You got to know that you’re going towards Cancun, you can’t be going towards New York. And if you’re pivoting, you run into it, which means, if that’s happening, then obviously you still need the money. Then the question becomes, how do you use the money that you have before you figure it out? So you can raise the next money. And when you hit these things called the in-between milestones, and you sort of have to raise money, that’s when the going gets very hard. So that first round is the foundation for the second round is the foundation for the third round, et cetera. So you’re perpetually raising but the strategy has to be about what’s the next milestone. And a lot of times you forget, because once you raise money, you feel like you’re a victor, and you sort of feel like, okay, I’ve won some sort of a victory lap. But the thing is, thinking about that next round and what are sort of the things you have to do in the milestones you have to hit is a psychology that takes muscles that take some training, and as an early-stage CEO, that training sometimes is missing, you know, as you go further in the journey, I’m sure Dheeraj thinks that way, I think that way, like, “What’s the next piece until you get to a place where you’re really self sufficient?” And even then, there could be times where that self-sufficiency gets challenged, you know, along the way. So that financial sort of thinking is very much there, but the mindset I would advise to an early-stage founder is “always be closing,” because money can disappear very quickly. And so if it’s there, you gotta take it. Another thing is how much to raise. And, you know, sometimes, you know, raise a little bit more. One of my mentors said, “You know, if the cookie tray is being passed around, make sure you take one-and-a-half cookies or two cookies, as long as you don’t starve somebody else, because that cookie tray may never come back to you.” Right kind of a thing for a while. So those are things to keep in mind, particularly at the early stage. You know, later stage fundraising gets much more sophisticated, and lots of different complexities come, suddenly a new channel of distribution came — Facebook — and we started to spend money, and we were growing like we grew 10x, but in that sort of rush to spend, we had overspent the money. And right at that time, the entire market dynamics was changing away from us, so we had to now cut down the spend pretty dramatically, which for a venture funded company trying to grow when you’re growing faster, you cut down spend. It’s very, very knee-jerk. And then we went to a phase where we had to raise a bridge round to go through that process. So sometimes you’re able to control that journey. Sometimes you just have to improvise along the way, and that’s where your partners matter. So for example, Mayfield and Menlo, who were both our partners at that time, both decided to bridge us and stepped up. And that, I think, is part of how your partnership is. Who are you surrounded with? Et cetera. In my previous company, there was a point in time I literally had to go around Silicon Valley and collect $15,000 checks to make the payroll right. And that was sort of a very rough time, because we were just at this specific place where we could see the world, but we were at a point where we didn’t have the world. A few months later we would raise a big round, but in that timeframe you needed sort of that small checks to kind of make it. And it literally went to two, three angels’ houses and then a couple of people’s offices to collect very small checks to make the payroll. You know that was happening. So I think funding is something that you know, when you see a company thriving, you may not realize that you’ve gone through some trauma, and at later stages, sometimes you have to kind of say that, ”Can you get the destiny and control hand?” This room where we are sitting in Walter right now, I remember sitting here with Navin [Chaddha] in the journey of Poshmark. And we were at a point in time, right before COVID struck, where we hit this cash point. And we didn’t know COVID was happening. So we didn’t know what was going on. And Navin looked at us and said, me and my CFO were sitting there, and said, “You guys got to become profitable.” And lo and behold, we have to do certain things. And within 60 days, we were profitable. We’d set a one-year target, because we had that much of a runway. We were able to do that. But that’s where you need that much mentorship advice. What’s the next sort of thing you need to do? So I think at different points in time, very early on, later on, money is never a question that completely goes out of the picture, because the bets you’re making are bigger, the expenses are bigger, the leverage is bigger around the book.

Dheeraj Pandey

I think my learnings have been about keeping the balance sheet in your head all the time, all the time. Again, it’s a visual piece of artifact that needs to be in your head. The sooner founders learn about what a balance sheet is, and also what a P&L income statement looks like, you know, many of them actually don’t appreciate what you know, what gross margin is, what remaining performance obligations is, what revenue recognition is. So I think it’s the adjacency of money is saying, “Look, I think I can have an educated discussion with my CFO and my with my VCs, and in my own head, I actually understand burn better than anybody else,” because, you know, you are the most schizophrenic chair is that of an entrepreneur. You know, one day, you’re optimistic, next year, you know, really paranoid, and the only way to balance it is to actually get the love and the attention, the delight from the users and the customers and the high fives that you’re getting from them. But then you also have to keep the balance sheet in mind like, you know, I need to know that I have 12 to 18 months of runway. Things have changed. Obviously, we are a result of the environment around us. I mean, my first company, I raised almost $2 billion and it was a low interest rate environment. So it’s like, oh, spend, spend, spend, grow, grow, grow. We were the fastest to a billion in like, six, seven years. I went public in seven years, since founding the company, seven years, you know. And then I think in this one, you know, the interest rates are high. So you’ve got to realize that even the VCs are hurting, because at the end of the day, their LPs are saying, “I can get 5,6,7, percent risk-free on the other side.” So people should also normalize rejection saying, look, it is not your idea that really is problematic. And the fact that you’re seeing more rejections now, and the only piece that’s getting funded is AI, which is also a hype. By the way, there’s a froth in this just like it was during the dot-com time. But I think the reason why I mention all this stuff around money is that people should actually say, “Look, this environment is just not friendly. And so how do I really live to fight another day?” I think this idea of living to fight another day is very, very important. Otherwise, when you run out of it and you’re looking at the precipice, it’s probably just the wrong place at the wrong time.

Manish Chandra

You know, I would say that that is a really good thing to keep in mind, living to fight another day. I think just knowing that time is your friend and your enemy at the same time is I think it’s very well, said the rich,

Walter Thompson

That makes total sense. It seems, though it’s, it’s tricky though, Silicon Valley, it seems that the people how do I say it exactly? Nobody wants to throw in the towel. Nobody wants to be seen failing or being perceived as a failure, right? So knowing when to say, “How do you know when to you know not what? How do you tap out? As far as, like, “Okay, I’m done with this fight. And moving on to the next one.” Is that something you had to me, to kind of have, both of you had moments like this, where you had to reach those moments, and kind of fight for those moments, as far as this is not the right moment, I want to move on?

Dheeraj Pandey

When you stop giving energy to others and now you’re expecting energy from others around you is the time when you know that this is done. You know, I think, because one of the key jobs of entrepreneurs early on is to give energy to others, and it has to keep happening. Because, I mean, it’s the energy to the market, the end users, to the angry customer. There’s a lot of apologies and thank-yous and all this stuff as well, but your employees are looking for energy from you, and in many ways, it is like walking in a fog. You just have to keep walking. But the more you walk, the more visibility you get. You can’t expect the sunlight to just come and break all the fog, and you have visibility for the next, you know, mile, or something like that. So I think the day you know that you don’t feel like walking in the fog, it’s time to actually do something else.

Walter Thompson

Last couple of questions here, I want to talk about personal development, the actual work of being a founder. I think people conceptually understand, but I think the emotional labor, it’s probably not well understood. One of the things that’s come through for me in this conversation is the humility. You have to have a tremendous amount of humility, and you can’t be too ego-invested, because you’ll get, you know, creamed, I would think. Fair?

Dheeraj Pandey

Yeah.

Manish Chandra

Of course.

Walter Thompson

So stepping back a second, work-life balance, I hear a lot of talk about work-life balance in Silicon Valley. Half my entire life I’ve worked here. It’s not really a question, it’s really more of a personal statement: I don’t think work-life balance is an achievable goal for an early-stage CEO. Do you agree?

Dheeraj Pandey

You know, I look at it as mind and body, and you can’t distinguish, so work and life have to be weaved in. I feel like, you know, there has to be peace at home. Can’t have war at home and war outside, you know, because you’re already at a war, you know, where nobody wants you to succeed, you know, except for your customers and your employees, you have no friends outside, so you need to have friends on the inside, at least, you know. So friends matter a lot in that sense.

Walter Thompson

Really quickly: what percentage of your friends work in tech?

Dheeraj Pandey

Probably 95%.

Walter Thompson

Manish?

Manish Chandra

Yeah, 80-90%.

Dheeraj Pandey

And so coming back to work, work-life balance, I feel like quality or quantity. You know? I mean in the last 13 years, we had three kids, and I feel like when I’m with them, I need to keep my phone away. Like being mindful. I’m a big fan of Simon Sinek that he talks about you can’t keep your phone on the table. You’ve got to keep your phone in the pocket. In fact, I try to keep it away as much as possible. I mean taking three, four vacations with them, where you don’t get to see the email and Slack channels during the course of the day when you’re on a vacation, only in the nights when they’re asleep is when you get to sneak in and do all that really important. But I think you know, again, you are on the front lines, and there’s a lot of blood bath. There is no such thing as life other than saving your life and saving your friend’s life around you and so on, you know? So I think people who are in this journey, including employees, they’ve got to realize that it’s it’s mind and body, and what I do is I celebrate three words: sleep, breathe and smile. So you got to sleep more. That’s the only way to get out of this momentary trough that you might have gone through because of rejection or loss or whatever else, you know, a customer deal, an employee, whatever it is. I think breathing is really important. I mean, as Paul Ekman talks about, you know, breath is an important piece of the puzzle. I mean, it helps you really connect mind and body, which is work and life. In meetings, when you think things are getting heated, you just need to figure out a way to breathe better and, finally, smile more, because you know your employees are also looking at you as a pilot in a cockpit, and they’re like, “What’s happening here? Is there turbulence?” And if you, if it’s turbulent, which many a time, you actually go through unexpected turbulence, your visage the way you actually have your face, not in a very authentic way. You know, of course, you have to share as well, but how much you share also matters.

Walter Thompson

I mean, you’ve been on this journey for 14 years. So how was your work-life balance early on, and how does it compare to 14 years later?

Manish Chandra

I agree with you that work-life balance in a theory, is very hard for an early-stage founder to fully get, so you have to prioritize and say, “These are the couple of things I’m going to do.” One of the things you have to do is to build your support system. So you know, if you have a family, your family is not supportive of your journey, it’s going to always create tension for you. If you are in a relationship and your relationship is not supportive, it can create tension for you. And many times, people have a vision of what it takes that’s helpful. You know, if you’ve seen entrepreneurship in your life, it’s helpful. But if you haven’t, it can be quite traumatic, right? Being in Silicon Valley is a little easier because people do understand a founder’s journey, and sometimes founders actually get undue respect even though they’ve done nothing. Yet in other parts of the world, it’s harder you know, the fact that you’ve left a secure job from a prestigious company, etc., can be misunderstood in that in that process, you have to sort of start to disconnect your ego a little bit in that, in that sense, the day-to-day sort of practices can sometimes happen, sometimes not. Sometimes you’re just stressed out. I remember in 2013, we were going through ups and downs, and I was going through a set of situations, and I didn’t really feel like I had anybody to turn to as I was walking around this building in our offices are outside, and I was just crying to myself because I was just like, feeling very frustrated. There were so many different pressures that were happening. So it’s okay to cry sometimes, too if you’re going through this process. I think everything that you’re going through, you just have to accept that’s a natural part of the journey. As a founder, there’s lots of ups and downs, and no matter what people look from the outside, they’re going through an “oh shit” moment every few days in their heart and minds at every stage, right? Because building a business is hard. I think that’s why co-founders are important, because they can actually be places where you can share something, but even with them, you can’t share everything. Sometimes, with your board members, you can share a lot, but you can share everything, sometimes with your spouse or your partner. You can share certain things. So you need different sources and forms. You know, as I’ve gone through this journey, I’ve had different mentors. They were mentors who were very powerful and good for me at a certain point in time, at some point, they felt like they were not providing me value, and I had to kind of find different partners. More in sort of the later parts of the journey, ‘15, ‘16, 2015, 16, which is like about six, eight years back, I joined some peer groups, peer groups of CEOs. We were CEOs on similar journeys at different stages. And that became a very, you know, done in a very structured way. It became one of the best peer mentorship groups, because we were all on journeys in chartered lands, where there’s very few people who have gone before, it’s hard to get their time right. So if Dheeraj wanted my time, I wanted Dheeraj’s time. It’s hard to get because we’re all so busy. But by giving your time to this group, you were able to get time from this group, and you got some of the best advice, not just advice about you, but hearing advice that was being given to them allowed me to learn about my own self. And the funny thing that I discovered in that process was a lot of times when you’re going through a particular point in time, a particular emotion. There’s many people because of the circumstances of the world, who are going through similar kinds of things, employee challenges, partnership challenges, financial challenges. And so that can give you both insights and to some degree comfort that you’re not alone. I think the worst feeling in the world, as an entrepreneur, is that you’re all alone, and the answer to that is that you’re not alone. There’s many people going through that same journey, many people who are on that same path. And by thinking that you’re part of a whole system, you can actually start to overcome some of the mental challenges.

Walter Thompson

Excellent. My final question for each of you, actually, if you were found yourself, hypothetically speaking, interviewing for a job with an early-stage startup, you’re talking to the CEO the interview, what would be one question you would want to ask before you accepted a job offer?

Dheeraj Pandey 

It’s a profound one. I haven’t thought about it, but Manish, why don’t you go ahead and I’ll think.

Manish Chandra

I would want to know what the CEO’s vision and motivation is for this company, not just the problem they are solving, but why they are on this journey. And that’s sort of something I would like to understand, is it, you know, and really try to see how authentically the CEO can answer that question at that point, and particularly in the early start. You know, if I’m meeting a third-time entrepreneur, why are they doing this? A lot of times, people are not sure. That’s where things fail, because they don’t know why they are on this journey, right? And it’s not that they can’t be successful, but they lose interest. They go in different things, if you’re so knowing the why is always very important to me and everyone that I partner with, and everyone I want to partner with. So I would think that that would be an important question, but I haven’t interviewed for an early-stage startup in 20 years, so I can’t be fully authentic about that question. That’s what I would want someone to ask me.

Dheeraj Pandey

I think, “How flat is the organization?” Because then you get to cross-pollinate on many other things and learn faster than were to be in a large company. Because what an early-stage startup really give you is like this breadth of exposure to every function, every department, you know, all sorts of people. So if I’m joining an early-startup, and it is actually very top-down and it’s very siloed, I think it’s the worst of everything.

Walter Thompson

Dheeraj, Manish, thank you so much for your time. This has been a great conversation today. I appreciate it.

Dheeraj Pandey

Thank you for having us.

Manish Chandra

Thanks.

Walter Thompson

I’ll be right back with some show notes.

Fund/Build/Scale is sponsored by Mayfield. If you have a fundable idea for an AI-first startup at the cognitive plumbing layer, email aistart@mayfield.com. The podcast is also sponsored by Securiti, pioneer of the Data Command Center, a centralized platform that enables the safe use of data and Gen AI. To learn more, visit securiti.ai.

Thank you very much for listening to season 1 of Fund/Build/Scale.

Across 10 episodes, I explored how founders and investors are getting AI startups off the ground. Next season, I’m expanding that focus to include all tech verticals.

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And thanks very much to Michelle for the love and support.

Thanks very much for listening. I’ll talk to you again soon.

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