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Where Are They Now? Episode 3

Where Are They Now? Episode 3

Episode 3: BenchPrep

April 29, 2021

Ashish Rangnekar, MBA ’11, grew up in a sleepy town in India where success looked like a white-collar job, not entrepreneurship.

But early on he encountered a problem: he had few resources to prepare for college entrance exams. A decade later, when he was living in New York and planning for the GMAT, he realized test prep options were still lacking outside of lugging a big book around or attending expensive in-person classes.

It was the dawn of the Apple app store, so Rangnekar and a friend launched a mobile GMAT test prep app, priced it at $9.99 per download, and hoped some friends might sign up. In the first month, it was downloaded by more than 1,000 people in 20 different countries.

“That was the first aha moment,” Rangnekar said.

The second “aha moment,” he said, was when he won the 2010 Edward L. Kaplan New Venture Challenge, giving him the confidence that his little test prep business could make it big.

BenchPrep, headquartered in Chicago’s Willis Tower, is now an online learning platform for standardized tests as well as professional certifications, credentialing and training. It has raised $28 million, partnered with 50 learning organizations and helped 7 million learners. It counts more than 130 employees.

In a conversation with Michael Alter, a clinical professor of entrepreneurship at Chicago Booth, Rangenkar, BenchPrep’s CEO, reveals the stumbles along the way – including how the company regrouped after a deal to be acquired fell through at the last minute.

“That was the moment of reckoning,” Rangnekar said.

Listen now on Apple, Spotify, Overcast, or wherever you get your podcasts.

Transcript

Ashish Rangnekar:

That was the first aha moment. Thousands of people all across the board needed a solution, which was mobile, which was interactive, which was affordable and which is on the go. That was the moment where we realized that, oh, wait, this is bigger than the project. This is bigger than what we had initially thought of. This is real. The demand is much bigger. The opportunity is much bigger and this can turn into something much bigger than what we expected.

Colin Keeley:

Hello and welcome to the Polsky Center’s Where Are They Now? Podcast. I’m Colin Keeley and we catch up with founders from Chicago Booth New Venture Challenge on this show. Join us as we dive into their entrepreneurial journeys, get a look at the stories and struggles behind their success. This week we have Ashish Rangnekar interviewed by Michael Alter. Ashish is the CEO and co-founder of BenchPrep, a SaaS learning platform for education and training companies to create and deliver personalized digital learning programs across multiple devices. They’ve helped millions of people all around the world run better and faster by leveraging the power of technology. Michael Alter is a professor of entrepreneurship at Chicago Booth. Previously, he is the CEO of the Tie Bar and co-founder and CEO of SurePayroll. Without further ado, here’s Ashish Rangnekar and Michael Alter.

Michael Alter:

Ashish first of all, thanks for taking the time. I’m really excited about the opportunity to get to know you a little bit better, to hear the story. I’ve heard bits of it over time, and it’s just a phenomenal success. And I know the story’s still being written and I’m excited to hear where you’re going as well. I’d love to start really early on if you will, there’s always been a question in my mind, are entrepreneurs born entrepreneurs or can you teach them, do they build it? How do you become an entrepreneur? And so I’m just curious, tell me a bit about yourself. Where did you grow up? What did your parents do? How did that come about?

Ashish Rangnekar:

Absolutely. And Michael, first of all, I am really excited to be talking to you about all this. So I’m looking forward to the next hour. So going back all the way, I grew up in India, in a town called Indore, it’s I would say a mid-tier town as per Indian standards, pretty sizeable in population, roughly 2 million. It’s a sleepy town, it’s actually known for its food more than anything else.

Michael Alter:

It’s something good to be known for.

Ashish Rangnekar:

Oh, absolutely. I miss that food. I grew up in, and I would say, a middle class home. My mom was a teacher. My dad was a retail banker. Both of them retired a few years ago. And entrepreneurship wasn’t really discussed in our house. I think my entire family and the next few generation were focused more on just, I would say, white-collar jobs, but no history of entrepreneurship.

Michael Alter:

Got it. And do you have brothers and sisters?

Ashish Rangnekar:

I have a younger sister, two years younger. She’s an artist. So we took very different paths. It’s interesting.

Michael Alter:

Got it. So how did you end up here in the U.S. and what was your first couple of jobs? Because I don’t think they were very entrepreneurial either.

Ashish Rangnekar:

No, not at all. Now I can actually connect the dots and see how I ended up doing what I’m doing, not just from being an entrepreneur perspective, but also the specific problem that I’m trying to solve. And if I go all the way back, I actually remember that when I was in 11th grade, my goal was to join this prestigious engineering college in India, the IIT, they’re like six of them. And back in that time, this is like 1996 by the way, this is pre-internet at least in India, there weren’t any resources available to me to prepare for the exam that gets you in those colleges. There were maybe books available, but in the town that I was in, there weren’t any tutors or any extracurricular help that I can actually get to prepare for that exam.

Ashish Rangnekar:

So I took a decision to actually move to a different town and live alone for a year so that I can prepare for this exam. And it just seems ridiculous. First of all, it seems ridiculous now that there weren’t the resources available, but I also feel very grateful that my mom and dad were totally okay with it. I mean, I was like 17 years old, 16 years old at that time.

Michael Alter:

Did you go to a private school while you were preparing somewhere else? Or what’d you do for that? Was it just preparing full-time for the year?

Ashish Rangnekar:

Yeah. So this is after I had graduated from high school, I took one year off, so there was a drop year so that I can actually prepare for this exam. So I moved, I lived alone, I rented out a house with a couple of friends. I went to this tutoring center for a year, took the exam and finally made it. And that experience not only shaped up how I made decisions for the rest of the life, but going to IIT — and I went to Indian Institute of Technology in Mumbai — going to IIT in those four years completely transformed my life.

Michael Alter:

Tell me a little bit more about, because the two things you said were fascinating, one was that that decision shaped your life and that approach going forward. I’d love to hear more about that as well as how IIT changed you.

Ashish Rangnekar:

Yeah. And this is all in a hindsight now I can analyze it. I look back at it and I realize that that was the first strong instance or two instances where I refused to just accept what was given to me. What I was trying to do, which was trying to go to IIT or even stepping out of my little comfort zone in Indore and living in another town was unheard of in our family. So I was okay being uncomfortable. And luckily I had the support of my family to do that, but then that almost became a norm. It’s like, oh, I can do this and I can be okay and thrive in this discomfort a little bit. So let me push a little bit more, push a little bit more. And that became an ongoing trend, which led me to eventually start this business and be somewhat successful in it. So I look back at that decision and I think that shaped a lot of how I made decisions going forward.

Michael Alter:

I don’t know who said it, someone said, but I love the quote, something to the effect of, you learn best at the edge of your comfort zone. And it sounds like that’s really where you positioned yourself and that’s what forced you into learning.

Ashish Rangnekar:

Yeah. On that note, Michael, I remember I was traveling and I think I was in Florence and this is maybe even like 12 years ago, I was in Florence, Italy living in a hostel and there was a quote in there, which I still remember very distinctively. It said, if you’re not living on the edge then you’re taking too much space.

Michael Alter:

Yeah. And you’ve managed to move forward with that. So walk me through, how did your experience at IIT, it’s IIT right? Influence you and change you?

Ashish Rangnekar:

Yeah. So there are a couple of really important things that happened at IIT. One was that I think that truly opened up my horizon.  I was in this small mid-sized down in Indore, and now suddenly I was in Mumbai, interacting with people who came from all across the nation. So just that network and me being able to observe and learn from all these other students was just incredible to me. It was one of those things where, now, I did well in high school. I mean, I was not the topper, but I was always like again, a good student. And now I suddenly come here and see like, oh my God, these are the best students from all across India. And I think that exposure just dramatically changed the way I thought about what is possible, what success means and what you can really do. So that is one thing. Second is, I met my co-founder there. So I met Ujjwal who eventually became my co-founder. He was my roommate and then we stayed friends and then eventually started the company together. And I mean, again, that was life changing.

Michael Alter:

So how many years ago did you guys meet then, before you started the business?

Ashish Rangnekar:

So we met in 1998, which was, what? 23, 22 years ago. And then we started working on this, I call a project, which became a company in 2008. So we had known each other for a good 10 years before we started this.

Michael Alter:

And just randomly you ended up as roommates?

Ashish Rangnekar:

Yeah. Actually, now that we are on it. I would say we were actually not even roommates. So we were allotted rooms next to each other and we convinced our roommates in the middle of the semester to change the room assignments that we could be roommates. And then the rest is history.

Michael Alter:

Excellent. All right. And so at IIT, is that four years, a four year institution? Is that how it was?

Ashish Rangnekar:

Four years, yeah, so I got my bachelor’s in mechanical engineering there.

Michael Alter:

And then what?

Ashish Rangnekar:

So then I came to US. I realized that mechanical engineering was really not where I wanted to spend my time. Mathematics was something that interested me a lot. So I came to US to do my master’s in applied mathematics, and I was in New York City, University of New York. And actually as part of that program, they offered me an adjunct role to teach pre-calculus to undergraduate students. So I was in New York, graduate student, 22 years old, taking my graduate level classes in the evening and being an adjunct teaching, almost kids of my age during the daytime.

Michael Alter:

Got it. What was that like? I mean, because I suspect the difference between your age and the age of the students you’re teaching is not dramatically different.

Ashish Rangnekar:

Oh yeah. I mean, it was frightening at multiple levels. I mean, first it was like I had never been outside of US. So this is the first time I’m stepping outside of the country. I am overwhelmed overall in just my, like the cultural differences were big enough that I was overwhelmed. I was overwhelmed with this whole me being a graduate student in a masters of applied mathematics program. And then on top of it actually teaching. So it was definitely overwhelming. I would say though, that it was definitely one of the most rewarding experiences of my life.

Michael Alter:

And which part, the teaching or everything together at that time?

Ashish Rangnekar:

The teaching part specifically. I think so first, that was the first time I was in the shoes of an educator. It was a very humbling experience because I was actually on one side during the evening as a student and then the next morning I have to actually teach to the students. I think that was a time when I truly understood what it means to engage a student to truly connect with them and empathize with them. And being able to really teach and educate from their perspective, not just from perspective of an educator. And then eventually the things that I learned during those, I would say 18 months, in the classroom became the true product design principles when we started BenchPrep.

Michael Alter:

Wow. And so I guess, had you not had that experience, you might’ve had a few more iterations to figure it out?

Ashish Rangnekar:

Definitely, at the minimum. I would also say that I think I would not have, I wouldn’t say I would not have, but I think that expedience just highlighted how fulfilled I felt being in the education space in general. So my mother is a teacher and I always looked at her and she always felt very fulfilled in that field. And then I went through that experience and I felt it, but that also highlighted the gaps in the system. And at that time I was not ready to actually jump in to be an entrepreneur, to start a company. But that experience always remained with me, which then came back five years later and pushed me over the edge and said, now I’m ready to start a company.

Michael Alter:

Any interest in becoming a teacher full-time or when you’re getting a graduate degree, you could go into academia and do this full-time if you were so passionate about it?

Ashish Rangnekar:

Yeah. I mean, I think it did cross my mind because I really enjoyed it. Honestly, I think there were a couple of considerations. I think one was just visa issues and visa considerations. I think I was compelled to actually take on a job. And second was the concept of driving impact at scale always fascinated me. And I mean, I taught maybe six sections during those three semesters and the thing that always kept going back to me is, all the stuff that I did to help these 150 kids, how can I do it for 150,000 students? And actually later on a lot of decisions that we made in terms of picking the right business model and stuff, were driven by that, like how do we drive impact at scale?

Michael Alter:

Got it. And so how did you end up going from there into the I think it’s the for-profit world, or did you go on for more education or what happened? You’re teaching, you’re at the edge again. It sounds like you change cultures, you’re at graduate education and you’ve got to teach these students you’ve never taught before.

Ashish Rangnekar:

Yeah. So I think that was definitely fulfilling. I think after I graduated, the program that I was in led me to a path of becoming maybe like a quantitative trader on Wall Street. I think it’s a great career. I think that that’s not something that I really wanted to do. So I started at Capital One, I worked in their corporate strategy team for five years, and this is the internal strategy consulting team. And that was actually fascinating. Even that time, I wasn’t really looking to start a company or become an entrepreneur. I was really happy just learning what I was learning. And Capital One at that time was, I mean, even today, but that time especially was this maverick of a company, very data driven decision-making, very meritocratic, gave a lot of freedom to me as a 24-year-old analyst.

Ashish Rangnekar:

And I  really got to see the inner workings of how a company should be built and scaled. I was working on projects that involved the CEO and the senior executives. So I got a sense of how to think about long-term strategy. So I had a great time there for five years. And it was when I was thinking of going back to school and started preparing for my GMAT exam is when this whole notion of, oh, things are broken in the education world and I need to do something about it came along.

Michael Alter:

So let me stop you there because I do want to obviously come to the business, but I’m just curious. It seems like you’re clipping along. You’re enjoying it. There’s all these opportunities, pretty hig- level opportunities at Capital One. And you decided you were going to go back and get your MBA, that’d be a third degree for you. I mean, what drove you to say, “Hey, I want to get an MBA?”

Ashish Rangnekar:

So I think I have a couple of things that I realized that at Capital One, which nudged me to consider an MBA. I think first was, I started to realize that my entire business perspective was singularly driven by how Capital One thought about it and everything about financial services. And after five years I had switched few roles and had worked with different business units and got to a point where I felt I truly wanted a much broader business/leadership perspective. And the options was like, hey, maybe I can switch to another job in a different sector, or I can go back to business school. And it was not even, in my mind, it was like, I want a much broader perspective and going to business school was definitely the best way to achieve that.

Michael Alter:

Got it. But it was a full-stop move, because you’re going to go full time to business school versus stay in Capital One and go in the evening?

Ashish Rangnekar:

Yeah, it was full-time. And I think the second reason that drove the full-time nature of it. So going back to what I took out of my undergraduate experience and IIT Bombay, one of the biggest thing was the network. I mean, I met my co-founder there, but not just co-founder, the broader network. And in US, I felt I didn’t have that strong of a network. And hence the second and equally important thing that pushed me to consider a full-time MBA program was to build the network. And that’s why I was convinced that I think at least for me, the full-time was the way to go.

Michael Alter:

Got it. So now you decide you’re going to do it and you start to do it. And this is I think the genesis of the business. I mean, how did you hit it, strike gold there? What happened?

Ashish Rangnekar:

Yeah. So even at that time, actually, yeah, let’s take a step back. So I’m at Capital One and the first step of going to business school is taking your GMAT exam. And I was like, sure. I’ll prepare for my GMAT exam, no big deal. And when I started that, I realized that there were a couple of options available to me. And this is what? 2007. So either I can buy a $20 book, a cheap, accessible, but I have to lug it around and it’s really not smart, it’s not telling me what to do and so on. Or I can actually go and take a Kaplan classroom program personalized to me, very interactive, but expensive $2,000. And more importantly, they expected me to walk into the classroom every Tuesday at four o’clock. And I just couldn’t do that. I was traveling and was a consulting gig and so on.

Ashish Rangnekar:

And I was actually amazed that how some of the things that I thought would be solved by now, coming from my adjunct time, was still there. I mean, the technology hadn’t really caught up, there weren’t really good technology solutions. And at the same time, in 2007, Apple had released iPhone and by 2008 they had released the App Store. So I could see all these apps floating around. And Michael, if you remember, there was an app where you could actually drink beer and the level would go down and an app where you could actually make all kinds of crazy noises and sounds and so on.

Michael Alter:

And don’t forget the lighter app too, where you could make lighter showing. Yeah.

Ashish Rangnekar:

And everyone was so engaged in this modality. And I looked at this and I was like, this is crazy. People are spending so much time building and using apps, which are, sure, entertaining, but really not life-changing. And here I am that I could have totally used a GMAT prep app on iPhone. And that struck me. I mean, I actually quickly went back to my like, oh my God, in 1997, I did not have good learning options. And then in 2002, as an adjunct, I felt like, oh, there’s so much you can do. And in 2008, again, I’m dealing with this. And all this accumulated to a point where I said, we got to do something about it. And that’s where this journey started.

Michael Alter:

Got it. So how did you start the journey? How’d you get started? You got this idea, a lot of people have ideas, what’d you do?

Ashish Rangnekar:

So I started talking to Ujjwal and, to clarify the situation: So by this time I knew that I’m going to business school. So I was working at Capital One transitioning to business school.

Michael Alter:

And did you have anything else going on or were you full-time that was everything? Or did you have a family at that point or what was your world like?

Ashish Rangnekar:

No. I was living in New York City. I had a girlfriend, not married. And then, Ujjwal, there’s nothing else going on, Ujjwal was finishing up his PhD at Penn State.

Michael Alter:

Okay. What was he getting his PhD in?

Ashish Rangnekar:

In Nanochemistry.

Michael Alter:

So not that related to GMAT prep?

Ashish Rangnekar:

Not at all. However, he had a similar experience. So as part of being a doctorate student, he was teaching classes and he enjoyed it a lot similar to the way I enjoyed my adjunct position. And he also felt that there are a bunch of gaps that a good technology solution can solve. So he was in that mindset, not related to GMAT prep at all. So we got together and we said, listen, here’s an opportunity. This is something that we feel strongly about. Both of us have taken too many standardized exams between us. We have too many degrees between us and we are seeing this amazing engagement driven by this device, iPhone, so we should do something about it. And we said, let’s build an app for GMAT prep.

Michael Alter:

Got it. And what was your vision at that point, in terms of, did you know you wanted to build this huge business that would serve at scale so many people, or was this just, hey, let’s see if we can get an app up because I can use it. So I don’t have to lug this book around.

Ashish Rangnekar:

Yeah. Honestly, I did not have a grand vision. We were not thinking about this as a business that would employ hundreds of people or a product that would touch millions of learners. Not at all. We thought about this as, hey, this is something that we feel strongly about. We know that people around us would really want to use it and maybe this would give us ideas around what we would want to do next.

Michael Alter:

Got it. But had you had any thoughts about being entrepreneurs at this point?

Ashish Rangnekar:

So both Ujjwal and I did our own little bit of entrepreneurship projects, I would say, while we were in undergrad, separately. So we had a taste of it. We knew that eventually we want to do it, but we never really actively talked about it until this point came in. And as soon as we started talking about it, I think then a lot of ideas came through and we started to look at this as a stepping stone into something bigger, but it wasn’t like, hey we want to be entrepreneurs so let’s do something. It was more like, hey, this is actually something that we want to do. Let’s see if this leads us to something bigger.

Michael Alter:

Okay. And did you know it was something that would have you step off eventually and do full-time or this was again, just, I’m still going to business school, this is just something we’re going to do in the interim or how did you think about it?

Ashish Rangnekar:

Definitely this was something that, hey, let’s do something in the interim and then see what happens. I mean, we really looked at this more as a project. I looked at this as, hey, this will actually be cool to do before business school so that I can actually learn from it. And then almost mold my two years at business school, accordingly than something that I thought I would end up doing for 10 years.

Michael Alter:

Got it. You can always write your application about the experience too, right?

Ashish Rangnekar:

Actually, yeah. I mean, that actually definitely came in handy. I think by the time I was writing application, the project was well underway. We had revenue and customers, so it was much more real than what I had initially expected.

Michael Alter:

Got it. So what timeframe is this when you and your co-founder are deciding, hey, we got to go do something about this? Is 2000…?

Ashish Rangnekar:

This is 2008.

Michael Alter:

  1. Okay. And you ended up, I assume, you started in business school in the fall of ’09, is that right?

Ashish Rangnekar:

Yes.

Michael Alter:

All right. So there’s a little bit of time there from that. How’d you guys get it started? How’d you get the first app built, how did you manage to release something?

Ashish Rangnekar:

Yeah. So I think this is the part that I’m actually incredibly proud of. So this is second half of 2007, Apple had released the iPhone platform, but the whole concept of building apps is a very new thing. There weren’t too many apps. There weren’t too many people who could build the app. I had some coding experience from undergrad. I actually had started my little consulting business when I was in undergrad and Ujjwal also came from technical field. But we weren’t developers and we didn’t really have experience developing mobile apps, let alone on iPhone. But we had a vision. We knew exactly what the app would look like. We knew exactly what it should do and so on. So we first tried to look for iPhone developers and there weren’t any, then we said, oh, maybe we should just learn ourselves and try to build it. And that was a consideration.

Ashish Rangnekar:

But then Ujjwal actually knew of this undergraduate student in his chemistry lab at Penn State, he was a computer science student, very sharp, very eager to learn. So we went to him and said, “Hey, we want to do this. And would you be open to learning how to build an app and build it for us?” And we said, “We’ll buy you a Mac book and if you could do it for us, then keep the Mac book and we’ll pay you. If you can’t, then it’s fine. You can keep the Mac book as well.” So we took a little bit of leap of faith. And we gave him a month to learn. And in the interim we were trying to figure out what else to do in terms of the product design aspect of it, what should go in there? What should be the functionality? What should be the UX? And so on.

Ashish Rangnekar:

This guy comes back in two weeks and goes like, “I’m ready, let’s build it.” And I was like, “Sure, let’s do that.” So I created content, Ujjwal worked on the feature functionality and UX. This friend of ours, his name was Roman, he actually build the app. And within two months we released the app on App Store and this was the first test prep app on iPhone ever.

Michael Alter:

Wow. And you guys, had you spent a lot of time out talking to people that were in the market for… They were going to buy the book or take the Kaplan thing to understand? Did you spend a lot of time sizing the market? Or did you think about your go-to market strategy? Or did you guys just, let’s build this up and go?

Ashish Rangnekar:

So we did. I was the ideal customer and I knew a lot of people like me. So that was the initial customer research. So there was my friends, my coworkers, people who they knew and who had taken GMAT or who were about to take GMAT, that was my network.

Michael Alter:

So you had the domain expertise here?

Ashish Rangnekar:

Yes. I would say we did market research. We didn’t do market sizing. We did market sizing from perspective of, hey, we are putting in $10,000. Are we going to get that back amount? Not like, is this going to become a multimillion dollar company or not?

Michael Alter:

Yeah. So you weren’t thinking about raising money or anything at this point in time, it was just, let’s get something out. Let’s help some people. Let’s see if we can make some money.

Ashish Rangnekar:

Yeah. It was truly like, let’s put this out. We’re going to learn about product design. We’re going to learn about marketing. We’re going to learn about how to create a business so that I can actually go to business school and mold my curriculum around it and do something bigger. Little did we know that this would become that big thing, and it’s amazing how it worked out.

Michael Alter:

Got it. So this was almost the practice.

Ashish Rangnekar:

Yes. That was what it was.

Michael Alter:

This was a practice business.

Ashish Rangnekar:

Yeah. And I remember we launched this app in December of 2008, and we said maybe like 20, 30 people would buy it. At that point-

Michael Alter:

You were charging for it?

Ashish Rangnekar:

So yeah. Pricing was a big thing. Most of the apps at that time were 99 cents or free, or some of the apps were like… I don’t even remember, they were like $100 apps and $1000 apps. So there was not good pricing models on the app store. But we were convinced that this is a high stakes exam. This is a serious product, and we had put in a lot of good design thinking behind it. And we said, we’re going to charge $10 for it, which we thought it’s very high. But we said, good quality product, we’ll charge $10. So we said $10. I’m going to put it out there, and we thought for the first month, we’ll make maybe… 10 people would buy it, 20 people would buy it. So that’ll be a good start. So we put it out there and during that Christmas to New Year’s break, we went on a ski trip. We went on a ski trip, and coming back from it, I think the end of the month, we were like, let’s check how many downloads do we have?

Ashish Rangnekar:

We were not even actively thinking about it. We log in and we saw more than 1,000 people had bought it from, and this is the kicker, from 20 different countries. Michael, that was the first aha moment where I was like, oh wow, this is not just the 20 people that I know who are studying for GMAT, but thousands of people all across the world needed a solution which was mobile, which was interactive, which was affordable, and which is on the go. So that was the moment where we realized that, oh, wait, this is bigger than the project. This is bigger than what we had initially thought of. This is real. The demand is much bigger. The opportunity is much bigger and this can turn into something much bigger than what we expected.

Michael Alter:

Bigger than the practice business, so to speak.

Ashish Rangnekar:

Exactly. Yeah.

Michael Alter:

I know in businesses I’ve been involved in, when you start to feel that you’re getting some product-market fit like that. People like what you’re doing and you’re onto something, what did that feel like? You got your $10,000 back, if I’m doing my math right. But what did it feel like?

Ashish Rangnekar:

It felt amazing in the sense that we were really just purely excited about the opportunity. And by the way, actually, and you’ll know as I tell the story, even then we didn’t really fully understand how big it is. But we said, hey, if it’s GMAT, that means it’s like ACT and SAT and LSAT and so on so forth. And we actually did not, even by that time, I did not even know the word product-market fit. I had not been doing VC, I had not read about venture capital, I had not read… So I just felt like, hey, this is a golden opportunity, we need to scale ASAP. And I had nine months before I started business school. So I started in September and this is end of December. So I said, I have nine months.

Ashish Rangnekar:

We need to do whatever we can in this nine months because maybe I’m going to go to business school and be so busy I won’t be able to spend time on this. We took all the money that we got and we reinvested and we started to build a platform. And by the time I started business school, we already had more than 40 different apps. We had a small team, no employees, but just contractors. And we were being regularly featured on the Apple App Store as apps to buy or the Education App Store and the best-selling apps and stuff.

Michael Alter:

Got it. And you had apps for other things besides GMAT then at that point, or was it just-

Ashish Rangnekar:

Yeah. Yeah. Yeah. We had gotten into other standardized exams. Just college math and bunch of other subject areas.

Michael Alter:

Got it. And this was all happening back in December. Had you applied to business school already, or were you accepted, or did you know where you’re going to go? Where were you on that front?

Ashish Rangnekar:

Yeah. So by December I knew that I was already accepted at Chicago Booth, and was really, really excited about it. By March when this was looking to be a business more than a project, I was already looking at NVC and the classes and so on. It was a really, really exciting time. I still, even that point, I considered this as, oh, this is going to be such an amazing thing to mold my business school experience around. But by that time, I was committed to, to join Chicago Booth.

Michael Alter:

Got it. And how did you pick Booth versus the other places you could apply and think about?

Ashish Rangnekar:

So I had specifically applied to only the programs that were very much focused on entrepreneurship as a discipline. So that was one of the criteria. This is very, very early stages of the Polsky Center and the NVC as a program and so on. But that really kind of stood out to me. The second thing was that I actually had met a bunch of alumni from Chicago Booth and other business schools as well, and it’s difficult to describe, but I felt much better connected to Booth alums than others. So I think those two criterias really stood out for me.

Michael Alter:

Got it. They were your people. You just fit with them. So you were set up to go to Booth. You’ve got your nine months to go, and your co-founder, he’s still getting his PhD, or did he give that up, or what’s going on?

Ashish Rangnekar:

He was still working on his PhD. He graduated in 2010. When I was starting at business school we already had customers and revenue and contractors and a brand name in this niche market.

Michael Alter:

Got it. Scale and scope, did you have employees? How much revenue did you have? How many customers did you have? What was it like when you came on?

Ashish Rangnekar:

Yeah. I remember the revenue numbers when we were in NVC, which is in 2010, and we were already at roughly $300,000 annual revenue.

Michael Alter:

Wow.

Ashish Rangnekar:

Yeah. We had found a team in India who was actually helping us build the product. So we had maybe like three, four developers working, all contractors. We didn’t have any employees. And then Ujjwal and I were working on this part-time alongside our full-time student commitments.

Michael Alter:

Got it. So you were still at Capital One at this point, or at least until you got to school.

Ashish Rangnekar:

Yeah. Yeah. Yeah. So I was working at Capital One until, I don’t know, like July of 2009. September I started at business school.

Michael Alter:

And then when you started at business school, had you already figured that this was going to be what you did when you graduated or were you going to go one of the tracks. What was your plan at that point?

Ashish Rangnekar:

Yeah. Yeah. Yeah. This is becoming a theme.  I knew that this business has had potential, but truly it wasn’t until we won NVC that I looked at it as a true career option. I was extremely proud of what we had built. We had 30, 40 different apps. We had tens of thousands of learners on our platform. We had more than $300,000 in revenue. So it wasn’t just a small project, but it wasn’t really until I interacted with… As I went through the NVC program and we won that I looked at it and said, oh, the potential is, again, much bigger, and we need to be fully committed to this, not as a side project, but a full-time commitment.

Michael Alter:

Got it. And that’s when you made the commitment. So I want to spend a few minutes on the NVC. There does seem to be a theme of, you’ve got a lot going on in your life, and you’re always on the edge of something. So you went from being a student and teaching in a new country to working at a pretty demanding job in strategy at one of the top companies, and then you’re building this business on the side. And then you decide, you know what, I’m going to go full-time to school, which is not usually a casual thing or a part-time role. And so all I’m going to start at this business school I haven’t been to before. I’m going to go full time, and I’m still running this business at the same time. So you’ve always got these multiple things going on. Did you know you were going to enter the NVC? It sounded like maybe you did before you even got to school.

Ashish Rangnekar:

Yeah. Yeah. Yeah. Definitely. I knew of the NVC program, I knew of the Polsky Center. Those were key decision criterias before I applied. They played a role in why I selected Chicago Booth. So early on, I was convinced. So we entered the competition the first year of business school, and we were fortunate enough to win it.

Michael Alter:

So tell me about that experience because I assume it wasn’t, we just entered and we won, and now we’re going to do this full time. I suspect there were some things in the middle, maybe. Tell me about the NVC experience.

Ashish Rangnekar:

So I would, first of all, totally characterize NVC experience as a game-changing experience for me. And I’ll tell you why for a few reasons. First is, I was convinced that, oh, I should go through this initially so that we can win the competition and get the prize money. By this time I already had customers, we had business, we had product. I underestimated the value that I’m going to get out of it purely from thinking about the business and the long-term vision differently.

Michael Alter:

Unpack that for me a little bit. What was different? How did you think about it before? How did you think about it after? What was there?

Ashish Rangnekar:

Yeah. I’ll give you an example. I submitted multiple ideas for the NVC.

Michael Alter:

Totally different businesses?

Ashish Rangnekar:

Totally different businesses.

Michael Alter:

Okay. Even though you have one that you’re running that’s doing a couple 100, $300,000 a year, and you’re a full-time student, you created some other business ideas?

Ashish Rangnekar:

Yeah. Yeah. And here is why. This idea was already formed. A lot more work to do, but I knew exactly what to write. I was actually very, very interested and fascinated for the opportunity to work with other students on other ideas as well. So that was the draw. So the more I got involved in the entrepreneurship club and heard about more ideas, I felt that, oh, our plan is already in the motion for the company that I had. And by the way, we were called Watermelon Express at that time. So Michael, just the name will tell you how serious we were about this as a business.

Michael Alter:

Right. By the way, I have to ask, how were you Watermelon Express, and when did you go from Watermelon Express to BenchPrep?

Ashish Rangnekar:

Going all the way back to that December, 2008 period where we created the app. So we knew that we wanted to call the app GMAT Express because like GMAT prep, and it’s express as in like it’s on the go, it’s bite-size learning. So we knew the name of the product. And then when we were submitting the application, they were like, “What’s the name of the company?” And we were like, “Oh yeah, we have to figure that out as well.” And then we spent hours and hours trying to come up with the name where we can get the domain name and it doesn’t mean anything weird in Spanish or something.

Ashish Rangnekar:

And we were spending too much time. And we had the product, and we just couldn’t upload it because we didn’t have the company name, or we hadn’t fully incorporated it. This is such a weird story, but that’s the reality. So Ujjwal and I were drinking watermelon martinis one day. And as a joke, I came up with like, “Hey, what about Watermelon Express?” And he’s like, “Sure. Let’s check if we can get the domain name.” We could, and right then we just said that’s the name of the company and move on.

Michael Alter:

Wow. It was after the first or second martini before you got to the name?

Ashish Rangnekar:

I forget. Given how weird the name we picked, it might have been more than that. But the thing is, then the movie Pineapple Express came up. And then our name sounded like… For an education company, that just sounded not appropriate. So eventually when we closed our second round of funding, that’s when we actually changed the name.

Michael Alter:

Got it. And I’m assuming that that was the name of the company, but your app was not called Watermelon Express.

Ashish Rangnekar:

No. We kept this express theme. So it was GMAT Express, and then we had a College Math Express, and then SAT Express, and so on.

Michael Alter:

Got it. Okay. So you applied to the NVC with multiple companies and Watermelon Express?

Ashish Rangnekar:

Yeah.

Michael Alter:

And did you grab some other team members from Booth to join you and your partner on the Watermelon Express, or did you keep it separate, or what happened there?

Ashish Rangnekar:

Yeah. Yeah. Definitely. So we grabbed few team members. So I knew one of my seniors, he was a friend of mine. His name is Saurabh Sharma. He was one year senior to me at business school. I knew him from New York. So he was part of the team. So it was me, Ujjwal, Saurabh, and then a couple of other folks who were senior advisors not related to Booth. So that was the team that we entered with.

Michael Alter:

Okay. And so I assume you got accepted. Did the other companies get accepted?

Ashish Rangnekar:

No. I think not to the final.

Michael Alter:

So, you got started. What was the experience like versus maybe even… Talk a little bit about what you expected versus what it ended up being. But what were some of the key things that happened during the NVC?

Ashish Rangnekar:

Yeah. So I think it was a phenomenal experience. I thought that given we have customers and we have revenue and we have a brand and so on, it’s going to be a breeze. In hindsight, it was so valuable that both the NVC judges and mentors really pushed us. And I used to look at other teams and the judges were challenging their core marketing plan because they didn’t have customers. And I was like, oh sure, we have customers so they’re going to be easy on us. And they weren’t. They really pushed us to think big and think strategic on dimensions that I had not really even thought of.

Michael Alter:

Give me an example.

Ashish Rangnekar:

And this one specific example, I would never forget. So one of the people who were involved with Professor Waverly Deutsch. And in one of the mentoring or coaching sessions, she really pushed us to think about our B2B strategy. So Michael, at this time we were a direct-to-consumer company, which later on we pivoted to become a B2B company, and that’s an important part of the story. At that time, we were not even thinking about B2B. And she pushed us and pushed us multiple times to a point where internally I was like, I just don’t understand it. We have such a good direct-to-consumer business. I don’t know why we should consider B2B. It took us four years to realize the value of that. So that’s an example where we were thinking… We are still in this, oh, this is a really good, exciting business. And we were thinking maybe like a year or two ahead of us, not five to 10 years, and that’s what NVC really pushed us to think.

Michael Alter:

Got it. Does she give you a hard time now, I could have saved you four years and a lot of headaches?

Ashish Rangnekar:

No, no, no. But as soon as we realized this and as soon as we made the pivot, she was one of the first ones to know.

Michael Alter:

Got it. Well, that’s great. And any other things that stand out in memory in terms of judges or mentors or folks that really helped make that NVC experience for you?

Ashish Rangnekar:

Yeah. Honestly, until that point, we weren’t really even thinking about fundraising. NVC was the first time when I understood that there are multiple ways to build and scale the business and venture funding is how it helps and how it all comes together. And I ended up having multiple conversations with Professor Kaplan on this. And this is even before we won. And I think that truly informed how we should think about our Series A round of funding. And I think it’s in those conversations that I started to look at this as a viable business and not just like, hey, we’ll win NVC and we’ll go back to my next class. But hey we have an opportunity to really raise capital, hire employees, scale the product and really make a big impact.

Michael Alter:

It also sounds like a bunch of the learning and the value of the NVC may have happened during the presentations, but it sounds like it really happened around them. And what happened outside of the three hours of class per se, when you present. That the meetings and interactions that you had throughout were what drove things. Is that fair?

Ashish Rangnekar:

I think that’s very fair. There were so many aspects of our business that we didn’t really even… like marketing strategy is a perfect example of it. Our primary marketing channel was Apple App Store, and we got really good at it. But it was the NVC judges who really pushed us to explore other marketing channels where we had to spend on some SEM and figured out what happens outside of the Apple network, which eventually became critically important as we tried to scale the business. So it was like a lot of those things where just because we had customers, they still pushed us in that direction. And this is in the classroom, and then outside of the classroom, there were these conversations happening with Professor Deutsch and Professor Kaplan that were beyond NVC.

Michael Alter:

Got it. And they kept pushing you?

Ashish Rangnekar:

Yep.

Michael Alter:

Again at the edge?

Ashish Rangnekar:

Again at the edge.

Michael Alter:

So when you’re going through the NVC, I assume it’s a little bit of a whirlwind. A lot going on. Now we’re a bunch of years later, we got a new class of NVC folks. It’s the 25th anniversary. We’ve got 30 companies that are just starting or going in. What advice do you have for them? What would you tell them to do to get the most out of this?

Ashish Rangnekar:

Yeah, so I would say, number one is if you can start early and by the time you’re in NVC, if you have a truly viable and thought-out business or thought-out product or a vision, that helps dramatically. The NVC would mold it and change it, for sure. It did it for us, it does it for everyone. But coming up with the plan just for NVC, I think that would limit how NVC would truly change the potential. In our case, we already had customers and revenue, and that made NVC that much more impactful. So number one is just come prepared much, much earlier than waiting for the class to begin.

Michael Alter:

Got it. Okay. And it also sounds like if one of those other three businesses that you had worked on had made it, it probably wouldn’t have been as good an experience because it wasn’t as far along for you.

Ashish Rangnekar:

Yes, yes. I would think so. Yeah. Number two is I think I looked at NVC not just for the NVC, but eventually looking at this as how would this help me actually run the business and grow the business beyond NVC? So my conversations with a lot of judges and coaches and professors were not just about winning the NVC, but actually about what’s the right thing to do to scale the business. And I think that approach dramatically helped me in later years.

Michael Alter:

Got it. So you weren’t playing a game to win, you were building a business. And it just so happened that as you built your business, you won.

Ashish Rangnekar:

Yes.

Michael Alter:

And so everything about what you were doing in the program was really for the long term of the business versus trying to, for lack of better word, manipulate around to win the prize.

Ashish Rangnekar:

Yes. Yes. Yes. Yes.

Michael Alter:

Interesting. And so roll forward, you guys win. Congratulations. Big deal. At this point, you said you decided you’re going to do this full time after you win.

Ashish Rangnekar:

Yeah. I think NVC helped me, again, realize the big potential. The first aha moment was December 2008 when we had all those downloads. The second aha moment was the validation from NVC. And that was the moment where I just realized that, oh, this is much bigger. This is bigger than a project. This is bigger than a class. This is a real business and we got to do it.

Michael Alter:

Got it. And did your co-founder Ujjwal, was he ready to go in full-time too?

Ashish Rangnekar:

Absolutely. And I think that the timing was interesting. So he had, by that time, graduated, and he had offers waiting for him from, I think in Dell and a couple of other companies. I still had my second year left. Actually, first of all, we were convinced that we got to do it. There were no questions around it by this point. 100% convinced this is what we’re going to do. For a brief moment I was like, maybe I should drop out and just do this full time. Then I realized that most probably my mom would disown me if I did.

Michael Alter:

Your mom’s a teacher, right? Yeah.

Ashish Rangnekar:

Yeah. And I decided against-

Michael Alter:

Plus you wouldn’t have enough to do just doing one thing.

Ashish Rangnekar:

Yeah. There you go. It’s all living on the edge. I think the second year was actually very difficult for me because I truly wanted the MBA experience, but by that time we actually had raised capital and had real employees. Looking back at it, I wouldn’t change it, but it was a tough year for me, I would say.

Michael Alter:

For sure. Did you adjust some of the classes you were taking to get more targeted towards what you needed in the near term for the business,?

Ashish Rangnekar:

100%. I was anyway doing that in the first year, but I wasn’t really that well informed. By the time I was in second year, I knew exactly what I needed. I remember taking this one class that Professor Ira Weiss had… I don’t know if he still has it. I think it was called Business Tax or Business Tax Strategy.

Michael Alter:

Yep. He still does.

Ashish Rangnekar:

There you go. It was so applicable to me. One specific example, we talked about stock incentive plans, and I was hiring my first few employees. It was literally either I could hire a lawyer who would just do for me or I could truly understand the mechanics of it and do it myself. And that was wonderful.

Michael Alter:

Got it. So you were able to get some timely classes that really fed into what you were doing. Excellent. So walk me through what happens next. You got some money from NVC. I suspect it’s probably not enough money to build the whole business going forward. You guys are graduating or your partner already graduated. What happened and what was the next turning point in the business?

Ashish Rangnekar:

Yeah. We got really good response coming out of NVC around fundraising. So we were having conversations with various Chicago-based forms.

Michael Alter:

And that was just the two of you, or did you have some employees at this point?

Ashish Rangnekar:

Just two of us. And it was clear that we want to scale it and we want to build a team, and we needed to raise. And we were having multiple conversations, and I remember one afternoon, I think I was sitting in my apartment and I was doing maybe homework for a class, and I get a phone call. And it’s a 312 number, and I pick up the phone. And I didn’t really pay attention to the name of the person who was calling because I was distracted. And the second sentence that I hear is like, “I would like to talk to you about potentially investing in your company.” And I was like, “Oh, hold on. I’m sorry, who’s this again?” And the voice on the other side says, “Oh, my name is Eric Lefkofsky. I’ve started a few businesses and I run this…” I’m like, “Oh my God. I know you Eric. This is amazing to get a call from you. I would love to meet you. When can we do this?” And he is like, “Oh, why don’t you just come in tomorrow?”

Michael Alter:

Wow.

Ashish Rangnekar:

So I’m going crazy. Eric just called me. This is exciting. They had just announced their Lightbank -nitiative. And at that time, my co-founder, Ujjwal was attending a conference in New York. I think it was one of those startup pitch competitions for NV, more in front of venture capitalists and stuff. So I said, you know what, let me just go and talk to Eric the next day. It’s going to be one of the 15 conversations that we need to have to close a round, so let me just take the first one.

Michael Alter:

Got it. And you’ve been looking at closing a round elsewhere yet, or had you had conversations elsewhere to sort of map the conversation you’re going to have against or what was the-?

Ashish Rangnekar:

We were having several conversations, I would say maybe two, three of them were in late stages. So we were talking to kind of a VC firm in Boston. We were talking to a group in Chicago, we were talking to a group in The Valley. So we had interest, but we didn’t have any term sheets or anything.

Michael Alter:

Got it. But you had a model of what you were going to expect in the process?

Ashish Rangnekar:

Yes. So I knew the pitch. I knew the ask. We hadn’t really fully formulated the terms and the structure and all of that stuff. We knew we had academic knowledge of it but we didn’t have a term sheet, so we didn’t even really discuss it internally.

Michael Alter:

Got it. Okay.

Ashish Rangnekar:

So I show up to Eric’s office and it’s just Eric and me and Eric goes so tell me what you do? And I was just fresh out of NVC. I knew exactly what to say and pitch. So I do my thing-

Michael Alter:

By the way was Ujjwal with you?

Ashish Rangnekar:

No. He was in New York attending that conference. And again, I was like, listen, it’s going to be first of many conversations, so you don’t need to be here. And you can join in the second conversation. So I go and pitch, Eric listens to me for 20 minutes and he goes okay, pause. And then he invites the rest of the team of Lightbank. And they were I think three or four of his associates. And then he goes oh, tell them what you just told me. So the next 20 minutes I do the same. And then they asked me a few questions and then he asked them to leave. And then we’re 40 minutes in the conversation. And then he goes to his white board and he puts the term sheet, he writes the term sheet on the whiteboard and he goes, “I want to invest this much at this valuation. Would you take it?”

Ashish Rangnekar:

And I was like, holy shit. First I was not at all expecting this. I had no answer. I did not know how to respond to it. I don’t remember what I said, but I’m sure I blabbered something, but I said listen, I need to talk to my co-founder. I need to think about it. So can you give me a day or two? And he’s like, sure. So I noted down the term sheet on my notepad and I called Ujjwal and he would not believe what happened. He thought I’m just joking with him, but yeah. But then we spoke and then we came back. We negotiated the term sheet well. And I think within a week we agreed to it. And then within a month we closed it. And this is in June or July of 2010. So I would say within two to three months of winning NVC, we had closed our first round of funding.

Michael Alter:

Got it. And so you were still a student when you closed the round?

Ashish Rangnekar:

Yep. I was still a student.

Michael Alter:

You still had one more year to go?

Ashish Rangnekar:

Yes.

Michael Alter:

Did Eric ever suggest that he wanted you to do it full-time versus stop doing this MBA thing and just go full-time versus, they were supportive of it?

Ashish Rangnekar:

No. So he wanted to know what my decision was, but he didn’t push me in either direction. He just wanted to make sure that between Ujjwal and I, we were committed to doing this. And we were. There was zero doubt in our mind. And by that time Ujjwal had graduated. So the whole idea was he would be full-time, I would be part-time and then I would graduate within nine months and then I would be full-time going forward.

Michael Alter:

Got it. So now you’ve got a bunch of money. Can I ask how much money did you guys raise?

Ashish Rangnekar:

Yeah, so we raised a million dollars at that time. And then later on we added another $1.2 million. So the first round became $2.2 million round.

Michael Alter:

Got it. And that was considered an A or a C?

Ashish Rangnekar:

We called it a Series A.

Michael Alter:

Okay. And did you get a bunch of board members that came with that? Or did it change anything in terms of the structure or the ability you guys had to run and build the company you wanted?

Ashish Rangnekar:

So both Eric Lefkofsky and Brad Keywell joined the board, and it was Ujjwal and myself. So we created a board, we didn’t have a board by that time. But Eric and Brad gave us full freedom to do it the way we wanted to do it. They wanted us to just do it really fast and really big, but they had invested in how we wanted to grow the business. So I think that was great help.

Michael Alter:

And they wanted you to go on the path that you were on at the moment that was working?

Ashish Rangnekar:

Yes. So they wanted us to remain in the direct-to-consumer business. They wanted us to truly invest in product because before that we had some contractors building out product. They wanted us to build a team, invest in product and then really scale. And that’s something that they were really good at. So we were excited that once we actually have the product built up for scale, their expertise would allow us to scale the go-to market very quickly.

Michael Alter:

Got it. And so you used some of the money to build a team?

Ashish Rangnekar:

Yes. So that’s when we started to hire. We hired our first few employees in the second half of 2010. So that was actually interesting. By the time I graduated in 2011, we had roughly, I think, nine, 10 employees.

Michael Alter:

And how do you prioritize who to hire what? Who to hire first, right? What were the areas that you hired?

Ashish Rangnekar:

Yeah, so both Ujjwal and I knew that the power of all this is in the product, and this is the early stages of mobile learning. This was the early stages of, I would say very early stages of digital learning, to begin with. And we were convinced that we were only beginning to scratch the surface when it comes to the power of digital learning. So our first investment was on the product side. So I would say the first four or five hires were strictly product and engineering.

Michael Alter:

Now, I’m assuming you’ve got competitors in the market, right? Are you feeling pressure that you’ve got to scale faster or, you’ve got some pretty big companies with some pretty big franchises, right? Kaplan, and some of these other folks that clearly are got to be moving into this market, that’s evolving. How was that playing out?

Ashish Rangnekar:

Yeah. So our business model, Michael, was slightly different. Our business model was that we actually never created content. And outside of that first app that I created in 2008, the core thesis of the company was this one key insight, which was that the modern learner wants to learn differently. Modern learner is distracted. They get too many text messages, too many Slack messages. They are impatient. They can’t sit in a classroom for hours and hours or watch a video for an hour. They are on the go all the time. So how do we solve for this modern learner?

Ashish Rangnekar:

And we looked at the industry and we said that, Hey, there is a lot of educational content out there already. We don’t need more GMAT content. We don’t need more math content. What we need is how do we actually move from this paradigm of content delivery to delivering a learning experience. And with that mindset, we said, we don’t need to create more content. In fact, we are going to go to these big educational publishers, license their content and deliver these learning experiences around their content to consumers. So that was the model. So we licensed content from McGraw Hill, Kaplan, Princeton review, all of these big names.

Michael Alter:

Got it. So it was more, a different way to learn and a different take on the content that existed, as opposed to you had unique content or unique information?

Ashish Rangnekar:

Yes.

Michael Alter:

Well you still had competitors, I assume, right? In some ways there’s a little competition, right? Because the guys that you’re licensing the content to are still selling the content in different formats.

Ashish Rangnekar:

Exactly. So we definitely had competition. We had direct competition from others who were trying to do exactly what we were trying to do. And then there’s a relationship with our suppliers, the publishers, right? It was almost like they wanted us to be successful, but maybe not very successful. So they looked at us as an opportunity to dip their toe in the digital learning or mobile learning space. All of them said, Hey, rather than trying to doing it ourselves, let’s see if Watermelon Express’ BenchPrep can help us figure it out. And then at some point maybe we’ll do it ourselves.

Michael Alter:

Got it. So as the business is sort of growing, you’ve got some money, you’ve got a different approach, the competitors seem a little bit at bay, at least as you’re describing, and they’re sort of watching you grow, what were some of the challenges you faced either expected or unexpected in that period?

Ashish Rangnekar:

Yeah, so we ran into, I would say big challenges in the 2012 to 2014 time period. This is the time when we were trying to scale. And what we learned at that time was that our product was great. Everyone loved the learning experience. But the unit economics in the direct-to-consumer business in the test prep world were just extremely difficult to manage given a digital-only product. So here we are with a really good product, we’ve just raised Series A funding, we were pumping in money in online marketing. And we are beginning to see a lot of traction, but the economics were still not working. In 2012, we ended up raising more capital. So we raised a $6 million round from NEA and Revolution. And the expectation there was that maybe if we spend more, the economies of scale are going to help us figure out better unit economics.

Michael Alter:

So a little bit more of if your brand is better known, awareness is there, your conversion metrics will all go up and therefore your cost to acquire is going to go down and you’ve got to sort of hit that critical number?

Ashish Rangnekar:

Yeah.

Michael Alter:

And is that how it worked?

Ashish Rangnekar:

Absolutely not. We were able to bring down our cost of acquisition, definitely. And the brand helped, the scale helped, the customer referrals helped, and so on. However, we realized that we are actually solving the wrong problem. The challenge was not the CAC piece of it, the challenge was the LTV. The model that we were in, the direct-to-consumer test prep space, we found it very difficult to increase the LTV of a user. You take a test, you prepare for a test and you’re done. And then you’re going to maybe come back in few years. So unless your LTV is thousands and thousands of dollars that Kaplan or other classroom programs would have, it was very difficult for us to compete in that market with a $100 LTV.

Michael Alter:

Got it. And so in some ways, sort of learning the lesson of why back when you started the business, it was either a $20 book you could buy at a bookstore probably back then because the distribution model worked, or it was a $2,000 program at Kaplan for the exact reasons you guys are coming across now, right?

Ashish Rangnekar:

Exactly. That was the third aha moment. Not a happy one. When we realized that I think scaling a direct-to-consumer test prep business for that kind of economics is just not going to be possible.

Michael Alter:

Okay. So you raised your next round, you got about sounds like about $8 million at least raised, I don’t know what you’ve got left. You got a pretty fancy well-known board, it sounds like. You’ve told them our story. You’ve told them your direction. Guns blazing, you’re scaling, and you have this aha moment you’re describing, which is the dog doesn’t hunt as we scale. Oh, S., right?

Ashish Rangnekar:

Yes.

Michael Alter:

So what did you do?

Ashish Rangnekar:

So what we did was too little too late, first of all. I think this is the time when, see entrepreneurs have to be, I feel irrational a little bit. During this time I felt we were too irrational-

Michael Alter:

Too irrational?

Ashish Rangnekar:

Too irrational. We believed in the product so much that we just did not look at data and we just kept pushing and kept spending and kept spending. And we got to a point where we had burnt most of our cash. So we had maybe less than a million of cash left. So maybe less than 12 months of runway. And it got to a point where I think at some point it was clear to us that this business model is just not going to work. The direct-to-consumer model is not going to work.

Michael Alter:

So great products. It’s just your go-to market isn’t working?

Ashish Rangnekar:

Yes. And at that time we actually got an acquisition offer.

Michael Alter:

Okay. From a financial sponsor or from a-?

Ashish Rangnekar:

From a strategic buyer. And both Ujjwal and I almost looked at this as, this going to save us. And we just went all in on it.

Michael Alter:

And the story for the strategic was, we already have access to these customers at a much lower cost. So when you put these together, we take this great technology and we can sell a lot more of it at a lower cost, or they hadn’t figured out the cost challenge you had?

Ashish Rangnekar:

No, exactly. So it was a public education company, they had really good and large customer base. And they were looking at this as a product extension. That they have already invested in customer acquisition, or they had subsidized customer acquisition across multiple products and channels. And this is a great kind of upsell opportunity for them.

Michael Alter:

And you guys have proved it worked.

Ashish Rangnekar:

Yes, our product was solid. Our technology was solid. So it was a great fit. And this is 2014, first half. And all of us got excited that this was going to save us. And we went all in, we took our eyes off of execution and just over-committed to this acquisition conversation. And it was very real. We got term sheets and board discussed it and it would have been an outcome where some investors would have made money, both Ujjwal and I would have made enough money. So we would have made so much money that at least I had not seen in my life. That me and my two generations above me might not have seen. It wasn’t retirement money, but just from where I was coming from, it would have been life-changing.

Michael Alter:

So, a very good outcome for you. Maybe not a hundred percent of what you wanted, but it’d be a victory?

Ashish Rangnekar:

Yes. I would say a good financial outcome for me. I think if you would have gone through that acquisition, I would not have called it a victory, but a good financial outcome. Yes.

Michael Alter:

All right. So you guys resigned yourself to go at, cause it sounds like there’s a little bit of, and maybe there’s a little hindsight in this, but it doesn’t sound like you were that excited about the acquisition. It was just like, we don’t really know what else to do. We’re running out of money. So let’s just go this way?

Ashish Rangnekar:

Yeah. That is was absolutely the case. And I was excited because it would have been an acquisition where our product, which we truly cared about would have been truly implemented at scale. It would have taken from hundreds of thousands of users to millions of users. So we were really excited about that part of it, but the goals that we had set for ourselves, it would have been a much smaller exit. And I think that was not exciting. Based on where we were, where we had less than 12 months of cash left. And the other option is to potentially shut down the company. This is a really good outcome from that perspective.

Michael Alter:

Yeah. So definitely much better than shutting it down. Did you guys look at, can we raise money and go in a different direction or was that really not an option because the acquisition was just too easy?

Ashish Rangnekar:

Yeah, that would not have been an option. I think we had already raised $8 million. The traction was decent, but not something that someone would want to kind of double down on.

Michael Alter:

Got it. And your board, how did they react to the acquisition? Were they supportive? Were they strongly supportive? Were they indifferent?

Ashish Rangnekar:

So I think they were supportive to what Ujjwal and I really wanted to do and we looked at this as kind of our get-out-of-trouble card. So we pushed for it and they supported it.

Michael Alter:

Got it. So it sounds like given where you are today, that something didn’t work?

Ashish Rangnekar:

Yeah. So the acquisition did not happen. It fell through literally at the last moment. We had all the legal paperwork drawn out. We had the term sheet and they pulled back at the last moment.

Michael Alter:

So big company changes strategy. You guys aren’t part of the strategy, we’re done? Or it was a, we want to renegotiate?

Ashish Rangnekar:

There were a couple of rounds of renegotiation, but at the end of the day, it was not about the price. They had just changed the strategy and we didn’t fit in as well as we did six months ago.

Michael Alter:

So just an absolute punch to the gut?

Ashish Rangnekar:

Yes. It was devastating.

Michael Alter:

So what’d you do?

Ashish Rangnekar:

So that was the moment of reckoning, right? So that was a moment where it was a decision between, I don’t know, there was no good decision to be made. We looked at acquisition as, Hey, if we don’t go through this, then we are shutting down. And then the acquisition failed. And the only option was, we had less than half a million of cash left in bank. That would have been like maybe three to four months of runway. We just didn’t have any other option than shut it down.

Michael Alter:

Got it. And what was the board doing at this point? Were they just saying let’s shut it down quietly? Or were they just watching you guys or how active were they in this?

Ashish Rangnekar:

So board was really active. And by this time we had NEA, Revolution and Lightbank and I had a really good counsel. But everyone by this time everyone had mentally committed to the acquisition. So this was a really big shift and a shock. So I think they left it on Ujjwal and me to decide. And Ujjwal and I got back together and we said, Hey, let’s figure out what we really want to do. What we knew was that, again, we were really convinced about the product and its applicability. We asked ourselves that, Hey, have we done everything that we could to take this forward? And the answer was, no, we haven’t. We were convinced that millions of learners wanted it. If B2C doesn’t work, let’s try B2B. If you have to change the go-to market strategy, let’s do that. If you have to change our product a little bit, let’s do that. But we were convinced about the market opportunity and we said, we owe it to ourselves to give it one last push.

Michael Alter:

All right. So, how do you do that, right? You’ve got three months of runway, four months, maybe a bunch of employees, a board who’s sort of engaged, but saying, Hey, you guys can figure it out. Were they offering you a lifeline of here’s a million dollars to bridge you? Or what did you do?

Ashish Rangnekar:

So we didn’t ask, they didn’t offer, because I don’t think that just money would have solved it. I think we had to look at the business very differently. And this is where all of those, the data points that we ignored and the nudges that we got over the last five years came into play. And we looked back at it and we said, listen, everything points towards the fact that we should explore a B2B strategy here. Product is what we’re really good at. It was the unit economics that didn’t work out. We still have a product. I remembered conversations with big publishers where we went and tried to license their content and they would ask me, Hey, we’re not really sure about licensing our content. We have never done that. We would want to license your technology.

Ashish Rangnekar:

And I was like no, that’s not what we do. That’s not our business model. All of those conversations really came back to us and Ujjwal and I said, listen, we got to try it. And we had roughly 23 employees at that time. We couldn’t carry the entire team because half of it was sales and marketing. So we said, We got to preserve cash. So one single day we let go of roughly 15 employees. And we came back from 23 to seven.

Michael Alter:

Wow. What was that like?

Ashish Rangnekar:

That categorically was the hardest decision I made. And one of the most difficult days of me being founder of a company.

Michael Alter:

And where are you guys aligned, Ujjwal and you on that was the right thing to do?

Ashish Rangnekar:

Yes. I think we were fully aligned. That was the only option that we had. We got really good counsel from the board. So we did everything we can to do it the best possible way we had potential interviews lined up for people that we were letting go. We had multiple conversations with them, but still it was difficult.

Michael Alter:

Right. And I know you guys did it above and beyond, and that in the community here in Chicago, you’ve reached out to so many of the other tech firms and help people get a safe landing, but I’m sure for you guys having to go in and talk to, I’ve been in your shoes. Go in and talk to these employees that are part of your life and say, it’s not working.

Ashish Rangnekar:

And I think when companies are small, and Michael, you have been there, you would know. I personally had interviewed each and every one of them. So I personally had selected each and every one of them. They are really smart, really committed. And I almost felt like we should have acted differently and changed the strategy much earlier and the outcome would have been different. So at that point Ujjwal and I really took it hard and looked at it as our personal responsibility that we had to go through this. And I felt we did everything that we could, but this decision actually weighed so heavily on us that it led to how we ran the company over the next five years.

Michael Alter:

In what way?

Ashish Rangnekar:

I think we over-compensated for this decision for a long time. And I’ll give you a couple of specific examples. So we made the pivot where we got down to seven people and we got really focused, by the way, we said, Hey, we have six months, we got to sign a customer. And I became the only sales rep. Ujjwal was managing product. We had our CTO. So everyone else was focused on product. I was focused on selling. I was able to sign a marquee customer in four months who paid us almost half a million dollars upfront.

Michael Alter:

Wow.

Ashish Rangnekar:

And that just completely changed the trajectory.

Michael Alter:

How did you do that? And how did you get that sale? It sounds like you didn’t know anything about, you weren’t the sales guy, as you said, you were the founder of the business. How’d you do that?

Ashish Rangnekar:

I think I was just so convinced about the value of the product. And not just convinced, we had data to prove it. So I went back to all of the conversations that we had where people asked me about the platform and I said, no, and I reshaped the conversation. And I think I understood the market and the needs really well. And I was not really bothered by scaling or what do I need to do to get the 10th customer. I was laser focused on that single customer. I think that just allowed me to truly think about the conversation from their perspective and that resonated really well. So the product was great. We were able to sign the first customer. Within six more months, we were able to sign the second customer, which has almost like a $1 million ARR customer. So by the time we got to the first two, then things were happening. We were beginning to grow, we became cash flow positive. So between 2015 and 2018, we saw really good growth.

Michael Alter:

So, it wasn’t just a pivot. It was almost a slingshot around the moon, right? You guys, you were going one way, you’re going pretty well. And then you just rocketed back in a different direction. Because it wasn’t like it took you two years to get some revenue and get the business going. You were able to pretty quickly pivot into a couple of great customers with some real cash flow that could leverage this technology that existed?

Ashish Rangnekar:

Yeah. And now I look back at it and it was like we didn’t have two years to figure this out. We literally had six months. So we got really lucky breaks exactly when we needed it. And I think we positioned ourselves well for it. We increased our runway from three months to seven, eight months by going through that reorg. And that kind of gave us a little bit of time. The first customer that we signed gave us a lot more confidence. I would say the commitment that I got from the five employees that we kept gave me a lot of confidence. So I felt it wasn’t just Ujjwal and me who are seeing the market opportunity and value of the product. But if these five employees are willing to commit to it, we have something that we should take to the market.

Michael Alter:

Right. Was it a risk for that marquee customer to sign up with you or was it a no-brainer? The person who said yes, do they play a role in this at all? Or was this a logical answer for them, no big deal?

Ashish Rangnekar:

So I think from a product perspective, it was a very logical answer. From just the company viability perspective, it was a risk.

Michael Alter:

Mm-hmm (affirmative).

Ashish Rangnekar:

But it was one of those things where we made ourselves look bigger than who we were. I think it’s just like, I remember phone calls when we realized that they’re going to have three people on their side, we made sure that we had four people from our side. They didn’t know that four is like 80% of our company, but that’s what we did. I think we over prepared. We created more documentation than was required. We had more people on the call, so it was just like, we were so fully committed to making this happen that… And they didn’t ask for financials or anything, and I feel lucky that they didn’t. Net net, I think it was a phenomenal arrangement for them as well. So it was a win-win, and it worked out well.

Michael Alter:

Got it. Awesome. So the business is growing and you’re doing all of this self funding, it sounds like, right? And I think you guys had, if I’ve seen my numbers correct, sort of doubling revenue every year for four years without raising money?

Ashish Rangnekar:

Yeah, yeah. And yeah, so from 2015 to 2018, we went from like what, zero to roughly like $8, $9 million in ARR in those three, four years.

Michael Alter:

Wow.

Ashish Rangnekar:

And that’s when I realized that we are overcompensating for that pivot. It was clear to me that we should have, in hindsight, we should have raised maybe in like 2016 or 17, where we had enough product-market fit.

Michael Alter:

So you were a little gun shy.

Ashish Rangnekar:

Yes.

Michael Alter:

Raise money, and that impacted your ability to grow. Even though you were doubling, you could have grown even bigger, even faster, even more?

Ashish Rangnekar:

Yeah. So I think that there are two, I would say mistakes that we made during that time. So one is we were just gun shy because we really wanted to be sure that now we have product-market fit. And second is, we started to over-index and overinvest on the revenue and go-to-market side than the product side. Because in the first phase we had phenomenal product and we couldn’t make the go-to-market work. After pivot, we were like, “Hey, product is fine, but we’ve got to make the go-to-market work.” So all the incremental investments were going towards go-to-market, not product. And then by the time we were in 2018, we realized that, “Oh, we should have raised much earlier and invested in product much earlier.” And that would have actually helped us scale to the next level much earlier.

Michael Alter:

Got it. So you had a bunch of tech debt, in some ways, that impacted your scaling. And in a lot of ways, I guess if you think about it sort of as a pendulum, right? Are we spending on product or are we spending on go-to-market? You were so far on the product, and then you swung so far over to the go-to-market that you let some of the other stuff go because you were just scared you’d run out of money.

Ashish Rangnekar:

Yeah, yeah, yeah.

Michael Alter:

Even with the revenue.

Ashish Rangnekar:

And not just, so take that, absolutely. The other thing was, because the first few customers that we signed were these million-dollar ARR customers, they came with a lot of needs. And million-dollar ARR customers always come with a lot of needs, but we let our product roadmap be driven by these few customers. Which might have been okay in the first couple of years. But then in later years we should have broken away from that practice. But it took us some time. And I mean, I would almost say it took us, like when COVID hit last year and when we had to, again, change our go-to-market a little bit, that’s when we realized that, “Oh shit, we have to kind of go back to our roots and become a more product focused company.”

Michael Alter:

Got it. And so with some of that, did you have one code base or did you have multiple code bases?

Ashish Rangnekar:

We had single code base. We have a really strong CTO. So from a pure technology scalability perspective, we were very solid.

Michael Alter:

Got it. So it was the ROI. And some of the places you invested were really just for this partner versus something you could use across all the partners.

Ashish Rangnekar:

Exactly. It was the product innovation where we could have done much, much better.

Michael Alter:

And was that innovation in end delivery or was it in platform capabilities to be a B2B player across everybody, whereas before, you were a platform for an end-user and those things are, there’s a layer in the middle there that you got to figure out.

Ashish Rangnekar:

Yeah, so it was the latter. I think we have always been really good at being focused on the learner experience. I mean, we have sold more than 6 million learners by now. So that has been our focus. Being a direct-to-consumer company kind of led us to this path where that became our DNA. And then we had to build all of these B2B tools. I think that’s where kind of, we should have taken a step back and said, “Okay, let’s kind of build it for future rather than building it for one customer at a time.”

Michael Alter:

Right. And I assume your channel partners want all sorts of reporting and different functionality to integrate this and tie this into that. And how do you create a platform that allows you to do it versus what each one wants and answers to them.

Ashish Rangnekar:

Yeah, yeah. So it’s an interesting lesson in how our early success kind of led us to a product strategy or a way of kind of building product, which kind of then became a problem three years later.

Michael Alter:

Mm-hmm (affirmative). But at least you’re around to have the problem. So 2018, you guys raised, that’s when you finally raised, right? The next round. Tell me about that.

Ashish Rangnekar:

So that was another kind of pivotal moment where, by this time we were doing really good. We grew from like zero to adding somewhere between eight to $10 million in ARR. Again, I mean, we had been running this business for eight years now, so it was really kind of sad, and said, “Hey, is this something that, should we, is this a good time to exit or should we just kind of keep doing this?” And it took us no longer than 10 minutes to realize that we have to go all in. We looked at the opportunity and realized that we have seen nothing yet.

Ashish Rangnekar:

It truly felt like we were in the second inning of a nine-inning game. And you don’t accept the score when you’re in the second inning. I mean, you go all in. So we said, “Hey, listen, this is good. We have found the product-market fit. Now we know exactly how to scale.” And we said, “We need to bring strategic investors in, people who kind of understand this specific B2B education market. So we went out and raised a big round and brought in a couple of more investors in 2018.

Michael Alter:

Got it. And so how has the business, or how was the business progressing until we hit COVID? We got a bunch of money. Was it as you guys thought?

Ashish Rangnekar:

It was. I mean, I would say the first order of business for me when we raised the capital was to build out the team. Because until this point, it was myself, Ujjwal, and our CTO, Nickolay Schwarz. And it was very clear to me that we need a strong team to scale this. We can’t kind of go from 10 to 50 with just three of us. So I almost felt like, I look at all of 2019 and it was all about kind of building the team. And we kind of brought in a sales leader, marketing leader, CFO, and so on, so forth. And then by the time it was time for this team to really kind of get going and scale, we are hit with COVID.

Ashish Rangnekar:

Now COVID is an interesting kind of situation for us because it truly accelerated the trend that we were betting on, which is around digital learning. And this is, and this very much is our moment to shine. And we actually saw good growth last year. We almost kind of tripled the number of new customers that we signed last year as compared to the year before. We signed some marquee customers. But it almost feels like, if we would have made all of those investments on the product from two years ago or raised capital a couple of years earlier, we would have been at a totally different scale than we are today.

Michael Alter:

So you mentioned you’d hired a bunch of folks in 2019. What was that like? Did you get that scaling and those hires right? Or did you have to tweak it?

Ashish Rangnekar:

I had to tweak it. I had to tweak it. This was the first time we were hiring senior folks and I tried to be so particular and disciplined about hiring every single one of them. And I feel every single one of them is a rock star, but even then we got it wrong on a couple of fronts. A couple of hires that we made, really strong leaders, not the right fit for the stage that we were at. One was too senior, and we were just not there yet. One had a very different kind of approach to scaling, and we were not there yet. So I think all in all, I would say maybe five out of the seven hires that we made were on point and we had to make some tweaks in the last year or so.

Michael Alter:

Well, five out of seven is actually I think pretty good. If you think about how the business has evolved, how have you had to change your role and your style to adapt?

Ashish Rangnekar:

Yeah, it has been dramatic. I mean, I almost look at it, Michael, and I feel like in 2017, I was the sales rep. In 2018, I was a manager. 2019, I was a recruiter. Last year I was almost like a chief storyteller focused on crisis management. So very, very different roles. I think this year is the first year that I’m doing the job for which I’ve been carrying the title for the last 10 years, of the CEO. And it took me a while, but I finally realized that my job is to make decisions when I don’t know what to do.

Michael Alter:

Yep.

Ashish Rangnekar:

And in a fast growing company like BenchPrep, I feel reality changes every quarter. And it’s like at scale, or given what we are trying to do, everything breaks. So I think finally I’ve accepted that my role is going to be around focusing on the mission and vision of the company and continuing to repeat and tell the story around why we are doing what we are doing. And then almost like spending most of my time on making those decisions where we don’t have a lot of data and we don’t know what to do.

Michael Alter:

Right. And I think, I’ve always learned, not making a decision is the same as making a decision. And that has its own implications of the lack of clarity and how it drives through the organization. And I suspect, as a larger organization now, please take this the right way, you don’t do that much. It’s everybody else that you’ve hired that’s done everything. And so it’s sort of the first 50 you hire are going to hire the next 250.

Ashish Rangnekar:

Yes.

Michael Alter:

And making sure that those next 250 know the story and know the plan, because they’re the ones carrying the keys to the car driving.

Ashish Rangnekar:

Absolutely. And it’s almost like they need to be part of the story. So it’s not just what I think. I can set the mission and the vision, but how do we actually get there? All of us have to try to figure this out together. They have to be brought in. I have to kind of bring them along the journey and then kind of make sure that we stick to our values and principles so that they can make day-to-day decisions by themselves. The other thing that I’ve learned in my role is also kind of the balance between intuition and data. And I think I’ve come to appreciate it kind of much more in the last couple of years. And I think Colin Powell has this rule of thumb about making tough decisions and he calls it, I think it’s like Rule of 40-70, where he says that if you’re making a decision without having at least 40% of the information, then you’re just shooting in the dark. But if you wait until you have 70% of the information, then you’re just too late. You have missed the opportunity. So that’s the sweet spot, like 40 to 70.

Ashish Rangnekar:

And as a Chicago Booth alum, and as a graduate student in applied mathematics, I’m a data hog. I need data to make decisions. And all this while I felt like, I just kept waiting for more and more data to make decisions. But in the last couple of years is when I have truly appreciated the intuition a founder develops after kind of going through all these ups and downs and being in the industry for a while and striking a balance between where I should kind of just listen to my instincts and guts and where I should keep asking for more data.

Michael Alter:

Right. It’s usually, I’ve always seen that to me, entrepreneurs versus the corporate America folks, the bigger companies, they’re more like an army, right? It’s ready, aim, fire. And there’s a whole process. And the entrepreneurs are ready, fire, aim. And you’ve made your decision. Now you’ve got to steer and make your next decision, because you don’t have the time as your business is growing so quickly to get the aim just right.

Ashish Rangnekar:

Yep.

Michael Alter:

So one other area I would just love to probe it, because you have a co-founder who was a good friend before you started. You guys have been together 20-plus years. You’ve been in the business now, 12 years, something like that, roughly, together? A series of questions around that, right? How did you guys make it work? How do you define who does what? Have you ever had any issues and how did they play out? And what advice do you have for someone else who’s thinking about getting a partner?

Ashish Rangnekar:

Yeah, so I think first, a big disclaimer. I got really, really lucky with my co-founder, really lucky. I think we have a very high level of trust and mutual respect. And that solid foundation has helped us kind of go through these ups and downs. And it’s been crazy 12 years. I mean, we came close to shutting down the company. Should we raise, not raise again? Hiring, I mean… thousands of decisions, but we have been fully aligned. So I think I just, in general, I feel lucky about kind of having Ujjwal as my co-founder. A couple of things that we did good early on was to truly set boundaries between what is going to my area of focus and what’s going to be his area of focus. So I continue to focus on the revenue side of things, and he continues to focus on the product side of things.

Michael Alter:

So, in a sense, he’s got 51% of the product role and you’ve got 51% of the revenue role?

Ashish Rangnekar:

Exactly. So I think it’s like we, and by the way, we openly discuss and argue about everything in a very constructive way. With the understanding that, on product front, he has the last call and veto, and on the revenue side, I have the last call and veto. And that has kind of worked out really well. So I think that’s kind of my recommendation when it comes to picking a co-founder or making it work. I think the, just being friends I feel is definitely not enough. I think functionally having complementary skills and focus areas helps, but having mutual respect and very clear distinction as to what the area of focus is, is critically important.

Michael Alter:

So where’s the future of the business. What do you see? What do you see as next? What’s the vision?

Ashish Rangnekar:

So I think this is where I think I go back to the opportunity. I mean, when I look at the digital learning space, I truly believe that we have seen nothing yet. Today, only 3% of the total education and training spend is digital. I mean, this is going to be dramatically different in the next 10 years. I mean, we’re going to look at this 10 years from now and say like, “What were we doing?” I think the industry is going through a massive digital transformation, and this is all led by the Fourth Industrial Revolution. I mean, finally we are living in a world where we have acknowledged that we are living in a world where technology is changing everything. And everyone is a learner and every organization is a learning organization. And education and training is going to have a big societal impact. Education, training, upskilling, and reskilling are going to drive tremendous value over the next 10 years.

Ashish Rangnekar:

So from a macro perspective, Michael, I look at this and say, “We are just starting.” I mean, sure, we have been doing this for 12 years, but we are only beginning to scratch the surface. And I think that is what is driving a lot of excitement for Ujjwal and I. There are tens of thousands of organizations who truly have to transform their digital learning offering. More than $250 billion of training spend is going to go digital over the next 10 years. And we are truly well-positioned to capture that. So we have set our vision to truly elevate everyone’s potential as we, as a society, we go through this massive transformation and our mission to say that we’re going to help every single organization out there become a truly great learning organization. So we have a long way to go.

Michael Alter:

Excellent. But I’d bet on you guys. It’s awesome. I mean, just phenomenal story. And to sort of hear the roller coaster of what it’s like to be an entrepreneur, the highs and the lows and how it goes up and down. And I don’t know if that’s how you felt, but how do you manage those highs and lows, right? I mean, at one point you guys were going skiing and didn’t think you had a business. All of a sudden, you got a thousand people paid money, you raised some money, then you’re almost out of business, then you’re back up, right? How do you manage that?

Ashish Rangnekar:

Yeah, I’ve thought about it a lot. Like what keeps me going? So I watched this podcast or I listened to this podcast, I’m going to quote someone else on this one. I think it was All Things Considered on NPR, where Alec Baldwin is interviewing Jerry Seinfeld. And they’re talking about a bunch of things. And in between that, Alec goes like, “Jerry, who do you think makes it in comedy?” So Jerry goes like, “Actually let’s ask a different question. Who makes it in showbiz? I’ll tell you who makes it in showbiz.” And then he says, “People who want to, make it in showbiz. Do they have the most talent? We’ll find out. But people who are really committed and who really want it, make it.” I think that’s how I felt about my journey. At every stage, Ujjwal and I didn’t look at this as an option.

Ashish Rangnekar:

We’re like, “This is what we want to do. Do we have all the resources? We’ll figure it out. Do we have all the funding? Definitely not, but we’ll figure it out. Do we have all the talent? Definitely not, but we’ll hire for it. But this is what we really want to do.” And I think that desire, I feel, has fueled our ability to live through all of this. And this has been an emotional roller coaster. I mean, up and down and up and down. I mean, even if I look at last year, Michael, I mean, we grew our revenue. While maybe half of the companies out there really struggled. And it still was an emotional roller coaster, managing a team of 130 people remotely, trying to drive impact for millions of learners every day in, day out is emotionally draining. We never looked at it as an option not to do it.

Michael Alter:

Got it. So if you sort of come full circle from growing up in India and sort of born to be an entrepreneur, nurtured to be an entrepreneur, did you become one or were you always one? To have this passion and energy that you’re talking about?

Ashish Rangnekar:

I think I’ve been nurtured to become one. I think I always had the instincts to get into uncomfortable positions, to be okay with putting myself over the edge, living on the edge and being uncomfortable. I mean, I have moved around a lot. I have switched roles even while I was at Capital One. So I always felt that I wanted to learn new things. I wanted to kind of push the envelope a little bit. I got a couple of lucky breaks that all this led to me starting a company, but looking back at it, I would not change a thing. I feel very fortunate to be an entrepreneur. I feel very fortunate to do something like this in the field of education. But I think to answer your question, I feel I’ve been nurtured to become an entrepreneur.

Michael Alter:

Wow. Your parents must be really proud back in India to sort of see what you’ve built and where you’ve come. And you should be really proud. It’s just such a great, great story of resilience, of smarts, of really building something great. And it’s really exciting to do it, and thanks for sharing it. Really cool.

Ashish Rangnekar:

Thanks, Michael. Absolutely. And I think it has been all the people around me that got me to this spot. So, lucky to be in this situation.

Michael Alter:

Is there any last advice that we didn’t cover that you’d want to pass on to anybody listening to this?

Ashish Rangnekar:

Sometimes I go back and look at some of the, or revisit, some of the interviews that I gave or podcasts that I did years ago. And I saw this theme early on when I was a young entrepreneur, and I used to say, “Next six months are critically important for BenchPrep. And then everything is fine.” And then I saw, I keep saying this like every six months. And I realized that it’s a long game. It’s a long game. And every six months the challenges are different. And that’s what makes it interesting. But as far as you keep your eyes on the long game and the true “why” behind what you’re doing, it all becomes meaningful.

Michael Alter:

So in a sense, it’s a marathon, not a sprint.

Ashish Rangnekar:

Absolutely.

Colin Keeley:

All right. That is it for this episode. If you could do me a huge favor really quick, please go to your favorite podcasting app, often Apple Podcasts, and rate and review our show. This gets the show recommended to more folks, and it also helps us get bigger and better guests for you to listen to. Take care.

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