Episode 94 / December 6, 2020

Inside the mind of Ashwini Asokan, Founder & CEO, Mad Street Den

hr min

Episode 94 / December 6, 2020

Inside the mind of Ashwini Asokan, Founder & CEO, Mad Street Den

hr min
Listen on

In this episode of 100xEntrepreneur Podcast, we take you through the journey of Ashwini Asokan, Founder & CEO, Mad Street Den.

During the conversation, Ashwini shares how she built the processes for scale while building the team, delivering the best value prop to customers, and more.

Listen to this podcast to learn about:

00:59 – Serendipity, luck, or intent? What initiated her journey in the creative field of AI?

03:11 – Influence of Carnegie Mellon University on her career

05:16 – Initial days of Mad Street Den

07:51 – Challenges while building an AI startup in India

08:08 – Lauching after 3 years of deep-research

11:42 – Essence of storytelling in positioning their offerings

14:28 – Building the team to scale to $1 Mn ARR

24:32 – Getting Sequoia India, Exfinity, GrowX, and FalconEdge on board

27:41 – Building processes to reach from $1 Mn to $10 Mn ARR

35:31 – Learnings/Advice to early-stage SaaS founders

38:18 – Early-stage founders comparing their journey vs some other founders’

46:19 – Has her “Why” behind starting Mad Street Den changed during her journey?

Read the full transcript here:

Siddhartha Ahluwalia 0:00

Hi, this is Siddhartha Ahluwalia. Welcome to the 100x entrepreneur podcast. Today I have with me Ashwini Asokan, founder and chief executive officer at Mad Street Den, an AI and computer vision startup based in Chennai. Ashwini returned to India from the United States after more than a decade to bootstrapped Mad Street Den, which she founded with her neuroscientist husband, Anand Chandrasekaran, in 2013. An alumnus of Carnegie Mellon University, Pennsylvania, Asokan graduated with a master’s degree in product design. She went on to work with Intel in California, where she led a team working on improving the user experience for mobile products. Welcome Ashwini to the podcast.


Ashwini 0:42

Thanks for having me, Siddhartha.


Siddhartha Ahluwalia 0:43

Ashwini, I have summarized your journey, but would love to know from you, you know, you were an aspiring dancer, then, you know, a product designer. And now one of the most vivid AI entrepreneurs in India, how does this journey happen? What was serendipity? The role of you know, intention, luck.


Ashwini 1:03

Haha. Okay. So, you know, I still remember being in high school and undergrad and swearing that I was not going to get into any computer related fields. So, and also any, you know, basic sciences in hardcore academic-related fields, because I come from a family of really, really highly accomplished folks, like my brother is a director of the gene therapy Institute at Duke in the US, he’s a professor, my husband is a neuroscientist, my sister in laws are physicists and toxicologists. So, I come from a family of either professors or just like hardcore geeks and computer scientists, right, this is my family. And the minute I decided I was going to be a dancer, it was, you know, everybody was like, fine, I think, you know, the personality lends itself very well to the creative fields more than anything else. I definitely was a bit of a rebel growing up, and, and just refuse to kind of do what everybody else was doing and had very, very, very supportive family as well, that was kind of nurturing of whatever I wanted to do. undergrad because I wanted to sustain my dance, and music careers, I decided I would just go and do my, you know, undergrad in Visual Communication, because it was again, kind of the creative arts and creative design. And, you know, all of that kind of changed. And I met Anand and he went to the US to pursue his PhD in neuroscience. And I decided to kind of pretty much abandon everything I was doing here in India and follow him to the US. And so my degree in Carnegie Mellon was almost a function of me trying to go be right next to Anand, rather than, you know, a journey that was all about me, you know, trying to create a career for myself in product design, or design or AI or anything for that matter. But Carnegie Mellon definitely changed a lot of things for me, I think my pretty much set the bar for the next chapter in my life. And I fell in love with the idea of product design, product development, and the role of technology. I mean, CMU is really, really well known for robotics and HCI. And, you know, it’s been much of my work with the, you know, I did a lot of work with the robotics team with the HCI team. And when I graduated, again, almost all my peers ended up going to, you know, Google Twitter, your classic kind of ideal design, classic kind of spaces that people were going with something very interesting happened to me in that Intel was hiring. You know, Intel was basically trying to become a platform company in the early 2000s. And they were hiring people from all different types of fields, right. And I mean, you know, anthropologists, designers, HCI people, ai people, machine learning, your vision, image processing, NLP, all kinds of people to kind of come in and, you know, bootstrap a lot of different types of efforts to becoming that platform company. And I had this opportunity to work with, you know, hundreds of people during that period, very, very multidisciplinary organization. And that journey of 10 years at Intel, and my mentors there, I’d argue pretty much gave me the blueprint for the kind of startup that I wanted to have. And, you know, during my course, at Intel, I think, you know, Anand and I already had started talking for years before, you know, we actually decided to leave California, but the kind of company we would do, and, you know, the kind of the reason why we would build these companies, so on and so forth. And, you know, 2012 2013 we found a very opportunistic time when Anand had finished his postdoc at Stanford, and he was kind of consulting. He chose not to become a professor. And we were just kind of preparing in some ways, which is like starting this company. And we just decided something just hit us. And you know, we just decided we were going to move to India, we made the decision. And in about three, four days, we moved to India. It was very abrupt, right? And, but that’s broadly how Anand and I function. We are very, very impulsive people. And once we make a decision, we kind of see it through. And so we came back to India to start this company. And what really drove us to start this company was, you know, we were surrounded in a world. And I don’t think a lot of this is faint to date, by the way. But we were living in a world where, you know, people are building AI for the sake of the technology, pushing the boundaries on the underlying technology, the infrastructure, the hardware, the software. And there was entirely the human component of AI was entirely missing in the conversation, right. And that had been something that I had been kind of harping about for years that, you know, trying to find meaningful applications of AI that can change both industry as well as consumer lifestyle in a meaningful way, we still don’t have too many of those. And, you know, it was one of those things where I would say, we just took it upon ourselves to say, we are going to go and figure this out. We don’t know how and why we had some hypotheses about how we wanted to do it, we wanted to build a, you know, we want to start off by building an AI platform. And we wanted to build a platform in a way that was, you know, very directed towards meaningful applications. We had a couple of ideas about verticals. So, it was a fairly blind jump. And it’s almost exactly like Reid Hoffman says, you know, we jumped and then we figured out how to put that parachute together with a plane together so that we could land fairly smoothly. And that pretty much summarizes my journey. So it was a bit of luck, it was a bit of serendipity. It was a bit of just being, I think, you know, constantly someone who was open to new experiences, I never limited myself to one thing, I was constantly learning something new, I can tell you my 20s were completely a journey of just discovering new things, taking new parts. You know, being a designer for a couple of years, being an anthropologist for a couple of years and being you know, product developer Program Manager, I took on many, many different hats, because it allowed me to learn several different aspects of the business. So you could almost say that my 10 years, my decade-plus at Intel was kind of like an apprenticeship getting me ready for this journey. So yeah,


Siddhartha Ahluwalia 7:39

What an amazing journey. It’s an amazing combo of co-founders, you have, you know, expertise in Human-Centered Design. And Anand has expertise in artificial intelligence. And you both combine it together to build AI, which is more human in nature. So, tell us more about the problems you’re solving currently. And at what scale are you solving?


Ashwini 8:06

So today, in the company, we have well known for our first vertical was actually launched a few years after we started the company, the first couple of years of the company, we were pretty much building out our platform, right? We were building out the underlying pieces of technology, our vision stack, our language-based NLP stack, or, you know, basically system architecture, putting the different pieces together, doing a lot of experiments to see if the underlying tech itself was usable, workable, I think was pretty much what we were doing for about two, two years or so. And then it was only at the end of it that we said, okay, let’s launch this vertical, the business part of it actually started only after we had spent a bit of time building out the core components, because you know, especially in the space of AI, we were strong believers that picking up off the shelf components was not necessarily very helpful all the time. Because, you know, they built for scale for generic problems, they don’t necessarily solve specific problems very well. And I’m talking 2014 15 timeframe. And so in 2016, we decided we were going to double down with the retail segment and we launched And we decided this would be the first vertical and we would first solve for this and learn how to build these applications, learn how to sell AI, learn how to go to market with AI, how to say these types of stories demonstrate value, and then we would kind of go into subsequent verticals like you know, any of the other verticals that are out there, whether it’s education or health care, or whatever else it is. So I would say 2016 end to 2020 now, three and a half years roughly has been completely focused on you know, the retail vertical, and now we’re at that point where things are looking great. And you know, the companies had a fairly rapid growth and vertical as well. And we are starting to very quietly, slowly start moving into adjacent verticals, which is a story for another day.



And, you know, you have some fantastic retail customers like Tata, mercadolibre. And Macy’s, how did you acquire such big clients?



See, the number one thing that I tell almost everybody that I typically work with, or people that I talk to is, you know, what is AI? AI is basically the, you know, anything to do with AI is about data, right? It’s about fixing cleaning data is about using data in a way that it can actually add value to a business in some form, or it’s using data to provide a fantastic customer experience. So it’s all purpose driven by the AI part is almost, you know, it’s taken me a few years to kind of get to this point where like half the companies or people around the world don’t care, you have an AI enabled phone. So what, like nobody cares. But if you have something that’s going to take a picture of you 10 times your selfies, like hundred times better than it ever will be, or, you know, if you can use automated speakers of say, like your snapchats, and your Instagrams of the world where you have all of these, you know, filters and stuff that can allow you to mess with them and play with them and all the ARs. That is what people care about. People don’t care that there’s AI in your phone, right?


Siddhartha Ahluwalia 11:21



Ashwini 11:21

And for us, I would say it’s broadly been that same kind of philosophy, right? Where, and we built almost all of our business stories around this, which is like, you know, you’re not selling AI to anyone, you’re selling a value proposition that has to do with making their business better. And the question is, how are you making that business better? And how would you say those stories, right, and so very early on, we ended up building very strong Product Marketing storytelling capabilities in the company that allow us to not just go to someone and say, Oh, I have a piece of AI. And it’s almost always met with so what, and I saw does 100 people, so do 100 people out there. And I think for us, it was very different. So we really focused on storytelling more than anything else. And showing value ROI very, very ROI driven AI and products, right. So but in terms of acquiring these customers, you know, there’s a saying in Tamil, which is, if you’re a young kind of, you know, cow, like a calf or an animal, you know no fear, right? Because you know, no better. And you just kind of go and do it, because you’ve never been told that it’s wrong, or it’s inappropriate, or whatever. And I would say, for us in the early days of, we just like called people or mail them or message them directly, and just kind of, you know, gotten away and said, Hey, just give me five minutes or 10 minutes and kind of really took the time to start networking with people and then got people to connect us, you know, and kind of brute force, right, that journey from zero to 1 million was hundred percent brute force, right. And, you know, there’s something about the lack of experience, which is just so you have no baggage, right? And as you continue to grow in your journey, you pick up a lot of baggage along the way. And you start questioning yourself doubting yourself asking the same question 100 times, you don’t have a lot of that when you’re starting the company. And I’d say, you know, for us, we were just we knew exactly what we wanted, we knew the kind of companies we wanted, we spent a lot of time really identifying just who we wanted to go behind why, and just kind of went at them, right with the stories. And it worked. I mean, you know, it’s not like everybody just opened the door and said, Yes, sure, come take whatever you want. But as it was about doing those early POCs. And during doing while we were doing this POC is you know, demonstrating the success metrics, showing that this has value, and then getting them to sign those massive contracts, right. So these are all journeys that we’ve gone through over a period of time. And having some early wins is always a fantastic way to kind of fuel growth, right. And so we ended up spending some time and this is where your Sequoia infinity, your board, right becomes very, very helpful, because they brought, you know, their network to the table as well, you know, and we had fantastic mentors who kind of, you know, helped us during that process. And so, early days of growth and GTM were just like a combination of just blindly jumping in and some help with, you know, from people that are in the network.


Siddhartha Ahluwalia 14:19

So, as of today, you know, you advice mentors on GTM. What was your thoughts on GTM when you started, listen, let’s take the first journey from zero to $1 million ARR. Did you like to focus on US India? Or How did you build that team to go from zero to 1 million ARR?


Ashwini 14:40

Yeah, you know, zero to 1 million ARR was me. The first 10 people were basically zero to 1 million ARR and, you know, I don’t think I knew what GTM was, I don’t think I knew what you know, customer success was all of those things. Now I know as terms and places and we kind of retrofitted them we now but we were doing all of this without even knowing that we were doing it right. So for us it was enterprise sales, you’re talking about few hundred thousand dollars for contracts, these are not your small 5$000 $10,000 deals. And so they’re very, very elaborate deals because yeah, that’s the nature of the product. And obviously, you know, I think obviously it required a lot of brute force, emailing people, calling people and getting in touch with the right people. And, you know, that journey was not I would say it was very chaotic, we didn’t necessarily know what we were doing, we didn’t spend any money on marketing, by the way, in those days, right, like no money at all, this was just email, LinkedIn calls, you know, calling people who knew people and just kind of, you know, getting folks to sign up and come and talk to us. So I would say GTM, for us was very, very people-driven in the early days, of course, it looks very different today. And when I mentor but it’s very different, right? Today, I have a lot of startups, you know, and founders, early stage founders talking to me, and, you know, I know better now, right? And so for me, like, you know, I always tell people make sure you have a product marketing person on day zero, right, especially if you’re a deep tech company, especially if you’re a b2b SaaS company, you really have to talk about the value of your product from a perspective of ROI and what meaning it has to have for the person on the other side, and why they should care. And those stories are not always very easily said by, you know, not everybody always has that skill set. And so having a group of people who can or even one person, right, who can write those emails, who can work with you, it really, really matters a lot. And it also matters because as you grow your team, you’ve got that original group of 10 people who have helped you say these stories, who can continue to grow and nurture the rest of their teams, right? So today, you know, I swear by the first 1020 people who are still there with us, many of whom are still there, and they still continue to play a very, very catalytic role in the company of growing the company right there. Like how do you spread that culture for years, five years, six years, seven years after the company’s been around, we’re almost 250. Today and across multiple geographies as a company, we’re in Japan, with us with Latin, in the Middle East, and people from very different backgrounds, cultures, were also not sitting in the same place. It’s important, you are a group of people that are constantly, you know, doing the rounds, continuing to nurture those skill sets and those stories. And so it’s not just a function externally in the ways I think that a lot that you end up hiring, you know, for the first few years, become very important and kind of spreading those stories over time as well, even inside the company. So, you know, today I tell people, you know, make sure you have a product marketer, everybody wants to hire your guy who’s gonna go spend your money on Google ads. But what are you spending the ads on? Right, like having the right people with you who can really, really, you know, put together those case studies in those early days, you know, really work with analysts in the early days. These are all things in hindsight, I would say done. But, you know, we have a really, really incredible team today, which I’m super proud of. So you know, better late than never,


Siddhartha Ahluwalia 18:16

Were your first 10 customers most from the US or India which geography where they’re from.


Ashwini 18:21

So for us, it was all mainly the US. It was not India, we did before we launched Yuria. We worked pretty extensively in India while we were building out the underlying tech. Yeah, but you know, is 2014-15 and nobody in India was paying for b2b tech at that point, especially enterprise deals like deep tech like us. And very quickly, we kind of you know, honed our products owned our underlying tech, and then we kind of launched in the US. So, you know, all of our work, zero to one mil journey, which lasted about 12 months. Yeah, so we went within 12 months, we went from zero to one, four bureau AI, and that journey almost completely happened in the US.


Siddhartha Ahluwalia 18:58

Fantastic. So, it must have involved you and Anand spending a lot of time there or it was from India,


Ashwini 19:03

it was a bit of both, I would say we definitely flew in once every two months or so, to the US. And you know, we still have our house there and stuff like that. And you know, so we were able to kind of set up two bases and go back and forth quite a bit. But it was a bit of both. It was not like we needed to be there all the time. The question is how much of that upfront you know, groundwork? Are you able to do that in person, right? Go there for three days, four days, really bond with the people there come back, continue the work, do the POC and then go back two months later, show the POC, right, and then come back and then you know, work on the contract and do the rest of it and remotely right so and the same 10-20 people who are you know, your customer success, your delivery, your product, your analytics and engagement focus spoke to the same 20 people that were all those hats right in the early days. And yeah,


Siddhartha Ahluwalia 19:59

I believe you’re talking about 2014-2015, it must have been really hard to hire AI talent in India.


Ashwini 20:07

No much to the contrary, actually my trip back to India was pretty much it happened because of the talent, I came back home. Chennai I love to say as a university town because it is obviously. We have more than 10 million people, it’s obviously not a town, but it just has so many universities such fantastic talent. And for me to be able to come back home was, was one of the main reasons I came back home. Because precisely because of the talent, right, you’re not going to compete with the Google in the valley, you are usually not going to be able to compete without, you know, 10 times 20 times the capital that you get to raise in India, right. So you have very different dynamics, and you have an amazing talent pool here you know, I think, if anything, the story of Mad Street Den is a story of its talent. And it’s been like I can say that hundred percent, right, like finding these people here. The team is what makes this company special. And the talent here and the skills here is what really makes the company very, very special. And they come in, they train for years, and we’ve continued to grow the leadership, the people that have been with us from Day Zero, make them managers groom the next group, right. So we’ve kind of been able to create this kind of, you know, a really well put together but also a continuous process is not a one-time thing, you can do this once and just stop. You got to keep nurturing it with the teams have to keep growing. And you know, you encounter different kinds of problems. zero to one is very different problems than one to 10. Right?


Siddhartha Ahluwalia 21:38



Ashwini 21:39

And, yeah, so it’s, I would say, this is the place for talent, India is the place for talent. I think every founder who wants to build anything, this is the place. I mean, India is definitely the place. So if anything, I think it’s the other way around.


Siddhartha Ahluwalia 21:54

Fantastic. And you credit all the success of Mad Street Den to the talent that you could attract, and help grow along the journey?


Ashwini 22:06

Absolutely. Absolutely. We think of this journey that we’re on as a journey where there are no paths, you know, how many AI first SaaS companies have been there out there in the world, right, that have succeeded or that have made it or that have models for growth? Not really, not really at all. And so we understand that these are, you know, first-time journeys, nobody’s built a path that everybody knows, we’re figuring it out, which means it requires a very particular kind of skill set that is extremely talented, but is also willing to suspend disbelief, right and able to experiment is able to go where we need to go work against all odds, and you have to believe that it’s possible. And so absolutely, it’s completely a product of the team.


Siddhartha Ahluwalia 22:51

And when was your first US hire in this journey?


Ashwini 22:54

Ah, so one of our co-founders has been in the US. But then I think, I mean, we didn’t grow our team or anything until 2016 we launched and 2017 was our first hire.


Siddhartha Ahluwalia 23:12

and definitely would have been, you know, growing the sales team there in the US.


Ashwini 23:17

Now, it’s a bit of both again, I mean, you think that, you know, you would think that But no, I think it’s always been a mix of, you know, a handful of people in the US and, you know, quite a big team sitting out of India. I mean, you know, you’d be surprised, especially now, I mean, of course, in the early days, it was very different. Because you still needed physical presence and people to go show up. And so we always had a couple of people in the US. But, you know, there are a lot of sale, especially today, right? Like boundaries mean nothing, like being in a different country means absolutely nothing. Everybody’s on the call. Right. And so we have people in India who are trained enough to do deals across the globe. So it’s been, it’s been a bit of a mix, right? Like the teams just work together constantly work together. While the sales teams are all sitting in the some of the members are sitting in the US all our solution engineers and sales engineers are all sitting in India. Right? So it has always been a bit of a tag team, cross globin. And the model has really worked out. I mean, I think place has a limitation now more than ever before has just disappeared.


Siddhartha Ahluwalia 24:21

In times of COVID. All physical boundaries have dissolved. Ashley, you mentioned in one of your interviews that you didn’t want to raise funds as the startup was bootstrapped, profitable. When did you decide and why did you decide to raise funds from VCs?


Ashwini 24:37

I think it was one of those journeys where we hadn’t really planned for a VCs or anything. We had come back, we were building our own thing. But you know Sequoia, being Sequoia found us before anybody found us we had registered the company, and they already found us. And, you know, yeah, people came people spoke You know, Exfinity, GrowX, they were all part of our early journey. And, you know, really early believers in the company in the deep tech, we didn’t even have a product, we didn’t have a vertical, we don’t have a business, nothing. So I’d say funding happened to us, we didn’t really go out there and raise funding. And, you know, a lot of them also ended up being a lot of customers to us, right? saying, okay, go experiment with this, like, here’s a company here is a healthcare company, here is a retail company and a lot of inbound kind of interest in connections to people. And as we started experimenting, and trying to understand where we wanted to take a platform, we said, okay, you know, we’ll just open up and go ahead, so very different than what it looks like today, right, our seed funding happened very, very different circumstances to people who were in a very different frame of mind, then the way seed funding or, you know, businesses become I feel like it’s become much more cut, copy paste today, like you have an idea, you pitch an early idea, you go to one of these accelerator programs, you know, it’s very prescribed, I think, today, it wasn’t the case in early days, when we had come back. And, we were also definitely, you know, clueless and people that had never worked in the startup community, or even in India, for that matter, it was definitely a bit of, we left the country when we were 18, 19, 20 in some form. And, you know, coming back with children and stuff was just very different experience for us completely. And so it took us a little while to get adjusted to everything going on here and set it down. And, and, you know, get the business going. But yeah, we have some very, very helpful people during that process, who’s guiding us every step of the way. And I keep telling people, right, but having the right kind of mentors around you is so important, so important. And today, there are so many founders who’ve already made it the second time, third time founders investors who’ve been investing for over a decade now, the talent pool in India, also on the founder and investment side is so much more mature it was than it was in early 2010 2013. That kind of timeframe. And there’s a lot of people out there who’ve really done it not just people who are claiming to be mentors and startup thought leaders, right, I’m not talking about people who’ve actually been there, done that. And who can truly provide help. And I constantly tell anyone that comes you know, and talks to me about this stuff is just like surround yourself with the right kind of people who can kind of remove roadblocks for you, right? It can help you show you your blind spots and stuff like that, as you grow in the early stage


Siddhartha Ahluwalia 27:29

So, Ashwini, I would love to know from you your journey from 1 million to 10 million ARR, what kind of processes you built in the company to reach that milestone.


Ashwini 27:39

So, the one to 10 Million journey has completely been about people process. More than anything else, right, the company’s DNA is definitely tech-driven product. And that is something we seem to continue to do at an insane speed like we are at this point in the company’s journey where products are released, there are not enough GTM people to actually go create GTM for the features like the fact that gets released in the company, that’s the speed at which we build our stuff and deliver to customers. So that our DNA over there is just top-notch. But we’ve spent a lot of time in that one to 10 journey really, really being focused on people and process right so hiring the right kind of managers hiring the right kind of leadership team. We don’t do this whole people manager, thing at MSD at all, we only do people who are very actively producers or whatever, you know, and are responsible as independent contributors as well, right. And they’re all technical leaders in some form regardless of the field they’re in, whether it’s marketing, or sales or customer success, or, you know, AI or delivery or engineering or whatever it is, whichever field it is, you have to be an expert in that field, owning a chunk of the work by yourself. Right and it’s a way for us to kind of continue to nurture that, you know, this is not just someone who’s men managing a bunch of people, but it’s someone who’s actually setting the strategy very actively responsible for, you know, doing a lot of the things as well. And so for us, it’s really been about getting really good talent, but we’ve also grown a lot of talent internally, I’d say the majority of the leadership team we have today were all ingrown, like completely, you know, grown from within the company. And this is definitely something that I know and Anand and I am incredibly proud of. We’ve spent the last five years or so, working to kind of grow the right teams make sure the foundation is right, have a really strong scaffolding for nurturing that kind of growth and I think we’re there right like and that has been one of the top needs in this journey to make sure that the scaffolding is super strong. And I think we’re there right like and with most of the talent is having come from inside the company itself and some for some of those roles that are entirely missing. We have to go find people from outside and bring them in more recently, that’s the first thing, the second thing has been, you know, figuring out how to step back, I think as someone who’s been doing the sales, I’ve been doing a lot of the sales, myself marketing, the product, the customer engagements, these are all things, you know, as a founder in the early stages, do everything yourself, right. And when you bring a team in, it’s a bit of a shock that you will have to even step back. And this is one of those things, my board constantly tells me to step back, let them do it step back, let them do it. And, and that has been another really important thing, right, making sure that the system is sustainable, and is moving at the pace at which it moved when you know, let’s say Anand and I or, and Costa and a handful of others were kind of you know, doing a bunch of things, right. And that’s the second kind of goal that I’ve been focused on is building an organization, not just the leadership and the management and, and the managers and grooming people, but also making sure that the processes are in place, are fantastic, right. And where people come in. And you know, as you continue to grow to 1000 people, you know, people just know, there are processes in place, there’s documentation in place, there’s things that are set in their ways. And so that’s been a really important focus as well. Which kind of brings me to the third thing, which is a bit contrarian to one and two that is discussed, which is, you know, the knowledge that’s constantly in a tribal group, like just tribal knowledge, right? Yeah, is also detrimental to growth. But too much process is also detrimental to growth, right? Because it becomes very red tape at that point, right? Everything is bureaucratic, you can’t move, like, you know, everything needs time, everybody needs a meeting. And that’s my third point, I think we’ve tried to set up a lot of autonomous systems inside the company that can move very quickly, right, like, just move quickly, there’s no need to wait, there’s no need to kind of, you know, call 10 meetings and but at the same time, communicate right over-communicate, make sure everybody who’s responsible? Or is the stakeholders aware that you’re moving this fast so that they can look at it? Or if they have issues or objections or something to add to it? They can add. Right. So these are all things that I think we’ve been working very, very hard at in that kind of window. And, you know, I think I’m feeling very good about it. I mean, and there’s a lot of friction as well, right, as you start to build people from different cultures that speak different languages. And, and those kind of milestones start to happen, you know, again, that a lot of friction over there. And, you know, making sure that the team is able to work together with one unit, but also have the autonomy to work in terms of small autonomous units that are highly highly driven, I think kind of balancing those two has been very important. And almost, I would say, the primary kind of, you know, foundation of thoughts, that I believe is going to be helpful as we march to 100 million goal.


Siddhartha Ahluwalia 32:56

I’m looking forward to the large milestone of 100 mil ARR by Mark Street Den.


Ashwini 33:02

Me too, obviously,


Siddhartha Ahluwalia 33:06

It would be India’s first AI startup to reach that milestone and only one of the few SaaS focused companies. And I hope that in the next few years, there are companies who have crossed that milestone or they’re at a milestone, are going public. So definitely have my fingers crossed, you know, to Mad Street Den public in the coming years. Right? You have built a company so much right way, right? You are the first AI startup with 50% Women, the time you emphasize on doing building the right culture and also speaking about it in the right forum is phenomenal, Ashwini. Ashwini, tell me one thing, you know, if you go back in time, one thing which you would have changed, what would that thing be?


Ashwini 33:58

If I would change one thing, what would that be? That’s a really good question. And I’m not sure I have an answer for that, you know, I’m one of those people who is often blamed for being too positive. Yeah. Especially in recent times, I think I’ve had my share of ranting and stuff, but I do tend to kind of be very optimistic about everything. And when I look back, you know, I want to say no regrets. I really do. There are lots of mistakes that you know, we’ve made and there are lots of, you know, things that could have gone better and, you know, we could have done so many things for faster growth better, you know, but i but i think it’s it’s no regrets and if I had to go back into a couple of things and, and I would say hiring and firing faster, like that’s the one that comes to me over and over again, right, like, I think I’ve definitely delayed both some, you know, very important hires, as well as firing and I, would say if I had to go back and do it, I would probably have fired the people I, I let go of much faster than I did, and hire the replacements much faster than I did. So I think that that is something that I constantly think back to. And I know that it’s one of those things that follows me to a lot of places. So, I’ll probably leave you with that answer.


Siddhartha Ahluwalia 35:24

And, you know, just for the SaaS founders who are early-stage listening to this podcast, what would be some of the other mistakes, which you did, which you advise other SaaS founders to just avoid in their journey to, you know, let’s say, a Million or a $10 million ARR, that don’t do these things, they would delay you by a couple of years.


Ashwini 35:42

Um, I think this is the phase where you continuously, you know, I think if I had to equate building a startup till that, that that kind of a 10 mil milestone it’s really all about. It’s almost like building a product. Yeah, you’ve got to iterate, you got to have your scrums. You’ve got to have your monthly releases, you’ve got to have your right hires to make that happen. And, and I often look at organization building itself as product building, and think of it as very similar parlance, or, and I think, you know, not getting too stuck on one thing, it’s important to have strong principles, foundations, you know, thoughts on how things should and shouldn’t be done. But I think a lot changed. There are so many variables, right, like so many variables, while you’re building a business and anything can change, your market can change overnight, your customer can go bankrupt overnight, your your, you know, there are so many things that can get out of control, I think. And so in a way you’re optimizing continuously for those variables to make sure that you’re not dropping the ball on one thing, right. So you always have to react with the same time you have to march towards a long-term goal, right. And I think balancing between reacting to something happening around you versus, like keeping our eyes on that, you know, end goal, I think, is really hard. And I think that is something that people like that nothing is too holy in that zero to 10 phase like the idea is to cross that when you have to do whatever it takes to cross that. And whenever somebody puts you in a box for me, I would say the biggest lesson has been breaking the box, I put myself into more than anything else. I constantly created boxes for myself, it’s so funny because my career is nothing if anything is the exact opposite of me putting myself in a box. And yet this journey from zero to 10, it was always you know, so much peer pressure, so much going on around you so much. There’s always something better, that’s very hard, I think the stress is insanely high. And I would say today, with this current situation, to be honest with you, I’m in a great place in the sense that I’ve kind of withdrawn from a lot of the noise, and really learn to focus on the signals that matter. And I would say that’s important in that journey. Just like the other point that I would say, focus, like, doesn’t matter what who raised or doesn’t matter what other people are doing doesn’t matter what anyone else has to say about you. The only thing that matters is what your customers have to say about you. Nothing else matters. Right? And being able to deliver at the kind of speed that you need to grow your business really fast is all that really matters and find that from within as opposed to kind of constantly having to benchmark yourself against everybody else.


Siddhartha Ahluwalia 38:34

In the last seven years of Mad Street Den. What have you learned to let go?


Ashwini 38:40

That last point I would say, is definitely what it is. And I think you know, I would say this journey is more like three and a half, four years old, really it’s not seven, I mean, I came back to the country seven years ago, the first year, I spent just adjusting my life back. The second is where we registered the company. In the third year, we decided we will build the platform and the tech and it was only by year four by the time we, you know decided, Okay, we’re gonna launch This journey is more like about three and a half, four years old and then older. And I would say during that period for me, the last thing that I told you is probably the most important takeaway, right? Like, don’t put yourself in a box and I think I’ve worked myself out of that box I put myself in, right I didn’t start my journey, putting myself in a box, putting myself in a category and expecting to, you know, performance. Certainly, I think the internet is filled with hundreds of ways everybody has a say opinion about how you need to do your GTM how you need to build your product, how you need to build your team, everybody has an opinion, right? And I think as a founder, you intuitively know a lot of these things. Right? And you can read it’s important to read it’s like a book, right? It’s important to read, it’s important to learn, but the circumstances that each of us is entirely different, right. And I think each of us needs to find a way to make it and our definition of success is different. And, you know, I know my ambition and my need to run, I was always running faster in my head, then my body was actually able to follow, to be honest with you, right? I was always three years ahead. And it was frustrating not to be able to catch up to where my head was. And I think that actually hurt me more than it helped me. And, today, I mean, Roy from Sequoia has been like this, this kind of, I don’t know, I don’t know what I would have done if I didn’t have them. So make sure that every one of you has someone to call it 12 o’clock at night. Someone who can, who can be this coach who can get you in the right frame of mind, who can get you exactly where you need to go, when you go off of, you know, the track, I think it’s very important, someone who can show you a mirror so that you’re continuing to better yourself.


Siddhartha Ahluwalia 40:52

And Ashwini, any books, which have been really helpful in this journey.


Ashwini 40:57

You know, I read a lot of books, especially lately, I’ve been reading all kinds of books, and I think I’m not going to give you one book, that’s just something that, you know, I think all of your usual suspects, I’m not going to talk about your zero to one or like odd things about that. I’m going to skip all of that. Right. I’ve started reading more biographies. You know, I’ve been reading a lot about the Intel Co-Founders, I’m hearing a lot about, on simplicity on this book by Edward de Bono, that I’ve been reading a lot about just the idea of what it means for you to embrace simplicity in your process, right, and not complicate everything. There’s another book by Richard Kapha, called misbehaving. So I think I’ve lately been reading more and more books about personality and traits and human behavior and little lesser and lesser about, you know, your how to get your startup to 10 million. I’ve had enough of that. I’m just done with that. Like that, you know, I’m just done with that genre of startup books for I think I’ve had enough of it. And so I think, you know, it’s messed with me, if anything, so I’m, I’m gonna ask everybody listening to this podcast, just stay away from that crap. Like, you’re gonna find your journey, when you’re in doubt, you know, read a couple of blog posts that tell you to fix a very specific problem that you have, you know, there are lots of people that speak truth to their journeys, go understand that, right, you’re going to figure it out, if you’re willing. And if you’re driven to make your company happen, you’re gonna figure it out.


Siddhartha Ahluwalia 42:45

The one point, I really appreciate which you put it, that entrepreneurs or people in general also put themselves in so many boxes, for example, let’s take a journey of a SaaS entrepreneur. So he would say, hey, Ashwini, you did your zero to one Mil in one year? You know, it’s been three years for me, but I have not reached that milestone, but it’s so much subjective, you know, it’s all about the domain, which you’re putting in, it’s about how much time has gone in preparation for that like you mentioned, it was approximately three to four years that you put into. So, you consider the MSD journey from 2016 17. And not from 2013. When you came to India, right? Really appreciate you putting forward that way, because we are trying to fix you know, as a solution as a society, or as an ecosystem startup everything into boxes, hey, zero to 1 million should be in X amount of years, one to 10 should be X amount of years. If not, you’re not doing something right


Ashwini 43:48

And I think those guidelines, I think they’re helpful, right? As for me, the way I think about it is the minute we launched The first 12 months for us going from zero to one mil the minute we figured that part of it out, we’re gonna do it was important for us. But that’s different, right. But for us, the journey prior to that we hadn’t even raised money. We were fully bootstrapped and we were building our tech, we came to India saying we are going to build our infrastructure and our platform and our tech and make it proprietary. And we didn’t compromise on that at all. Right? Like we refused to start the business side of things until we actually got. Up to date. I’ll tell you we could have cut down a year or a few months, like that. But today, the pace at which we’re able to scale a platform into other verticals even quietly. It’s because we put in that time, right early on and we did it on our own terms. And I think it’s so yeah, I think you know, you just have to decide because I mean VCs, at the end of the day, are in the business of making money and so if you’re taking VC money, you better go by the rules. And if you want to be bootstrapped and you don’t want to be you know, bothered by anyone, no worries at all. That’s a part as well, but I feel like this whole like there’s no one way.


Siddhartha Ahluwalia 45:02

So you don’t believe in you know, your zero to one should be so much amount of time. When you talk to the your mentees or one to 10, it’s so much amount of time with so many resources.


Ashwini 45:12

No, I tell them that if they’re going to go raise a seed round of like one and a half million, 2 million, 3 million, and if they’re going to go make a pitch, then you are bound by like, like you decided to go a certain way, right? And it might not always happen. The point is, it might not always happen when you have the right kind of board they understand no one’s gonna like screw you over within like, you know, the first and not give you a chance at survival. I don’t think that’s the case at all the especially now more than ever before. India, my God, everybody who’s anybody is raising money at insane prices. So if anything, I think it’s a founder market right now. Absolutely a founder market right now. So, you know, some of the stuff that you know, you typically went through the early 2010s or late 2000s, I think we don’t see much of that anymore, I’d argue. Right. And, and it is a founder market. So, but if you do have taking VC money, and you have a plan and blah, blah, blah, you can be putzing around, right, there’s also that side of it, right? So you know why you’re starting the company? And starting the company, even though I mean, the number of proposals I get like even when the company started, you’re like, Oh, I’m going for you know, I’m going to raise money, and you’re like, Do you even have a business proposal? What are you raising money for? Right? Like I encounter that a lot. So, I just think that, you know, VC, No VC, decide what your goal is, you need to have a goal. You need to be otherwise you’re there’s no company company is meaningless otherwise,


Siddhartha Ahluwalia 46:42

for me, I didn’t get ask it earlier in the podcast. But I want to ask right now, why did you started MSD? and has that wide change over a period of time?


Ashwini 46:52

And no, it’s not. Anand and I are on a 30 year journey, 25-30 year journey. We believe our road leads to a lot of places, we have a vision for where we want to be 10s of years in the future. And this is just, you know, a first step towards that. And why I started MSD I would say, you know, I am one of those people that truly believes that it is important for as much of the world to participate in creating AI and being AI illiterate, and being AI native. And I think MSD is a journey for me in building really really large scale businesses that actively employ and empower people into becoming part of this AI ecosystem.


Siddhartha Ahluwalia 47:46

And why is AI ecosystem important to you? Your education has been different, your background has been different from that,


Ashwini 47:55

Because I see the world in the future being completely AI filled. And I think if we all don’t figure out how to get people to be a part of that AI future, then you’re just going to be you know, having a handful of people who are going to be dictating what you consume, what you do, everything is going to be dictated by a handful of people. Right? And in order to make the future much more equitable. It’s important more and more people are part of that and are getting ready for it right now. Right now. Right? And if and it’s absolutely and I believe that industry and large scale industry is one way to continue to get people into that AI economy. Right. And to me, MSD is absolutely an endeavor towards that. And not only do we skill people grow with people here inside the company, we’re also able to bring these kinds of tools and productivity tools and AI based systems to people in other companies and our customers who are able to work with it. And everybody is kind of I think it’s a both in inside MSD teams perspective, but also inside customer orgs and their team’s perspective, I think it’s an effort to get everybody part of that AI community of AI future. And that to me is you know, MSD is a way for me to make that happen. And scale is extremely important, because not enough, If a handful of people are part of that, for me, it’s a really, really large industry that I hope to go over 10s of years with, with the nod of lot of people that can be a part of that.


Siddhartha Ahluwalia 49:26

Thank you so much Ashwini for your wisdom, insights and experience that you shared on the podcast. It’s been a pleasure.


Ashwini 49:34

Thanks for having me, Siddhartha.


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