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July 18, 2023 · 31 min read

Season 4, Ep. 17 – Founder to Founder: With Adit Jain, CEO and Founder, Leena AI

This week on Founder to Founder, Teja talks with Adit Jain, CEO and Founder of, a tool designed to improve onboarding and internal communications with their advanced virtual assistants. They talk about the ins and outs of growing a global workplace culture, the future of AI, and empowering employees to do their very bet work.


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Teja (00:05):

Yo, what’s up guys? Today, we have a cool conversation with Adit Jain. He has a company that he and his two other friends have started and have scaled to over 400 people. Super impressive company, super impressive founders. I learned a lot. I think you guys will too. It’s with Adit Jain of Leena AI and go send them a shout out. Find them on LinkedIn, find them on the interwebs, ‘cause I think you guys will like this one. (THE FRONTIER THEME ENDS)

Teja (00:46):

Okay. Awesome man

Adit (00:48):

Absolutely, Teja.

Teja (00:49):

Tell me a little bit about yourself, man. How’d you kind of get into building your company, entrepreneurship? Like, what’s your background?

Adit (00:57):

There are three founders of Leena AI: Mayank, Anand, and myself. We’ve been, you know, we’ve known each other for the last 13 years now, so it’s been quite a crazy journey. We were in the same wing in IIT Delhi, so it was like, you know, being in a hostel means like, you know, it’s like you know, IITs have these hostels where people are generally put in and they’re like, you know, very old school, you know, very limited amenities there, you know. It’s not probably the best of cases, but you make the best friendships for life, right, and that’s where, you know, I became friends with these guys. We used to do a lot of projects together. We took a lot of courses together, and, you know, over a period of four years we kind of had that friendship and that trust in each other’s abilities and how we complimented each other, that we said, you know, while we had great job offers, we said, you know, “Let’s just try and, you know, do something of our own.” (Teja: Yeah.) We had to go and convince one of the parents <laugh>. (Teja: Of course.) In India, you still have to do that, right? And I remember how we begged <laugh>.

Teja (02:12):

<Laugh>. So, that’s so interesting. Yeah, because, you know, in our culture, it’s like, you kind of become a doctor or something very consistent that you can kind of build a family very easily through. So what was that process like? Like, how did you, what was the pitch that you made to convince somebody?

Adit (02:31):

So one of the things that, you know, IITs provide you is a good safety net, right? (Teja: Right.) So you can say that, hey, if you’re gonna fail in six months, you know, probably you will have a job waiting. (Teja: <Laugh>.) So that’s probably, and because, you know, you said it rightly, right? So while we were chatting, you said that, you know, India is growing. (Teja: Right.) So for good people, there’s so many opportunities that it’s just crazy, right? Even in this downturn that the U.S., North America, Europe is, you know, Indian engineers are still getting five offers each <laugh>. (Teja: Right.) So, you know, we have that safety net, that confidence, and you know, after that, it’s just begging, right <laugh>?

Teja (03:13):

So, in your family, or like, let’s say in the founders’ families, is there like, a history of entrepreneurship, or are you kind of the first generation of entrepreneurs?

Adit (03:22):

So my dad has run his own company, a software company, for like, 15 years, right? So school is, yeah. So for me, it was easy for me, right? I had it easy. For the other two, one’s parents are doctors. The other ones, you know, had a government job <laugh>, so they had it tough. Yes. We had to convince them a lot.

Teja (03:44):

Got it. Did your dad help, or was it mostly just like, you were just like, we have to figure out how to do this?

Adit (03:51):

So, you know, it did not come to that. I just needed, if it would’ve taken much more time or effort than maybe we would’ve involved him, but yeah. Their parents also agreed. I think I had it fairly easily <laugh>.

Teja (04:04):

Yeah. That’s cool. I’m sure you’re persuasive, (Adit: Yeah.) and like, there’s a positive role model there, so it’s like, cool to see that, hey, okay, there’s gonna be some guidance. Okay, so that’s awesome. So IIT, but then you guys went to YC, got tier one investment from Bessemer Venture Partners. So how did you guys get connected to basically get to like, the most prestigious set of financiers in the U.S.? You know, that’s so cool.

Adit (04:31):

Twenty-fifteen, when we completed our undergrad, we loved AI, right, because we had done some, you know, courses and projects in face recognition, in natural language processing, automatic content summarization, right? (Teja: Right.) So we were like, we wanted to do something in AI, for sure. So we decided to kind of explore NLP, and at that time, you know, Facebook just released their API for, you know, chat bots. So that was pretty interesting, because we thought, okay, with AI, and with this platform, which people can access, and it kind of changes things. And I think, at the same time, telegram had also opened their API, right? So we thought, you know, this makes total sense, in terms of, you know, allowing customer support automation, marketing, sales, you know, you can just do things. So the WeChat thing in China could actually hit the other parts of the world as well, right?

Adit (05:20):

So we said, “Okay, let’s build a platform.” It’s currently, you know, it’s still alive. We call it ChatterOn. So ChatterOn is a, like a horizonal platform that enables anyone to create chatbots without writing a single line of code. So it’s like, yeah, you know, you can come in, it’s a DIY platform, and you can, you know, build a website, Facebook Messenger, or Twitter chat bot for customer support marketing or sales automation like, without any coding or very little API, you know, usage, but like, almost zero coding, right? (Teja: That’s cool.) So that’s where we started off. That kind of blew completely, blew up completely. It went from zero to over 30,000 developers, companies, you know, people using it to build chatbots for their, you know, different portals. And you know, that was amazing. It was encouraging, you know, wide ranging use cases. We had a freemium model from a subscription standpoint. So the problem was that we were charging after a particular chat bot had over 10,000 messages processed, right? (Teja: Yeah.) And, you know, it’s crazy, Teja, but our 30,000, only 20 people ended up paying us, right?

Teja (06:36):

Yes. I see. I see. Yeah.

Adit (06:40):

So now this is a huge problem, because, in two years, we had scaled well, but we were not able to monetize, and we started to diagnose what’s happening, and we realized that we had made the classic rookie entrepreneurship mistake of trying to be everything for everyone, (Teja: Yes.) but ending up nothing for nobody, right?

Teja (06:57):

Yes, yes, yes.

Adit (06:58):

It’s like, the classic-est, you know, mistake you can make as a first time entrepreneur, (Teja: Yes.) and we made it. The good thing is when we looked at those 20 customers in detail, Teja, we realized that out of those 20, around 16 of them were actually using ChatterOn to build internal HR and IT chatbots. And we had zero professional experience, by the way, and nobody teaches you what they do in HR, what they do in IIT undergrad, even across the world, right?

Teja (07:30):

Yeah. You don’t know what they are. You’re just like, yeah, for sure <laugh>.

Adit (07:34):

And we were like, you know, “Okay, what are these guys doing?” You know, people are like, they would request like, “Okay, I want to access, you know, Adobe Pro. What is my league balance? And you know, it’s crazy, right? (Teja: <Laugh>.) So we called up those guys, all 16 of them, and we said, “Okay, why are you doing this?” And then, you know like, three months in, we spend three months doing this, and we realized that the problem is access to information, right? So as organizations grow, there’s so many different systems, people, applications, departments, that finding the right information to do your job, is a huge time suck. That’s essentially what we wanted to solve with Leena AI with our vision being building J.A.R.V.I.S. for every employee in an enterprise, right?

Teja (08:19):

That’s cool.

Adit (08:20):

And we’ve stayed true to that, you know, goal, to that vision, ever since. You know, we don’t want to do customer support chatbots. We don’t wanna do marketing sales chatbots. We only build employee-facing virtual assistance. That’s what Leena AI is, right? Post that, we went to YC in summer 2018, raised the 2 million dollar seed round, after that, and then, you know, 2019 was a great year of growth for us. Twenty-twenty, even with Covid hitting and, you know, it had its own silver lining for us where you know, we actually were able to see a lot of revenue growth, because suddenly companies were remote, right? So supporting employees became really challenging remotely, right? Because you could have found an IT person, an HR person, like, two desks away, but that’s not happening now, right? So they had to automate. So we had that super growth happen, and you know, at that time, we raised a Series A led by Greycroft, so it was an inbound. So one of the analysts at Greycroft, you know, just wrote us an email. We happened to respond to it, and you know, I think we are one of the few deals that ever happened with the cold reach outs from analysts, right <laugh>?

Teja (09:34):

Oh my gosh. Were you surprised by that? Or were you like…

Adit (09:39):

Now, I am. So by that time, you know, at that time, I didn’t know that it’s such a big thing that never happens. (Teja: <Laugh>.) Right now, after, you know, speaking to so many people, I realize nobody has cold reach outs from analysts. But, you know, amazing job.

Teja (09:55):

You’ve made that person’s career, probably. Like that will be a line in the resume until that person becomes partner. 

Adit (10:06):

Hopefully <laugh>.

Teja (10:07):

<Laugh>. So founded like, maybe 2015, 16, had one product, made a second product that hit, went to YC, went, you know, and got the seed and the Series A. That’s like, really fast growth, and so right now, your company is split, San Francisco, California, and New Delhi.

Adit (10:33):

Absolutely. So we have, in the U.S., we have people all across the U.S. We have a heavy population in California, New York, you know, Atlanta, and then we have other AEs and go-to-market folks across the U.S., because those are extremely localized markets, right? (Teja: Yeah.) And they’re like, very close groups of buyers, the CIOs and CHRs, you know, closed groups of buyers, so you have to have people on the ground. And we do enterprise deals. We do large teams, right? So now, apart from that, we have development centers in India, in New Delhi, Mumbai, and Bangalore, but we also have go-to-market teams in Southeast Asia, and in Europe, and Middle East.

Teja (11:13):

When you think about, kind of, business climates, is operating in these different markets, does that present unique challenges, or is it all pretty straightforward, and you got some compliance with all that stuff set up?

Adit (11:27):

No, absolutely. You’re bang on target. Like, I told you we raised our Aeries A, and then we raise a Series B next year. So we raised our Series B in 2021, 30 million dollars, (Teja: Oh, wow.) led by Bessemer, and we started opening geographies after this. We opened Europe and Middle East after that, and you know, I was shocked, because, you know, like, the completely different culture, especially Middle East, is a completely different culture. (Teja: Yes.) And for you to go in and…because you have to speak their tone, their voice, you know, their language. You have to understand their culture when you’re going into sell, and, you know, I’ll be honest, it’s been an…I’ve spent close to three months over the last two years in the Middle East, and you know, I can tell you I know much more about their culture, you know, and how it has evolved over the last 200 odd years, and you know, how do you actually go and sell to them, but by being there. But you can hurt that without, you know, being there.

Teja (12:25):

That’s so interesting. So what’s some of the idiosyncrasies? Like, what do you have to, how do you have to kinda position things in the Middle East?

Adit (12:34):

Absolutely. Language. So Arabic is an extremely important language. If you’re building a solution you know, if you’re a company, you are a startup, you want, customers in Dubai, in Abu Dhabi, in you know, KSA in Qatar, you need to have Arabic in the product. You need to have Arabic speakers who are doing sales, business development or customer success.

Teja (13:02):

Wow. Okay. And so will you guys even like, adjust the marketing site to basically be in Arabic, so when they land, wow. So not just the product. That’s crazy. Okay.

Adit (13:15):

You know, there are holidays, there are buying cycles, budgeting cycles, because, you know, we do $500,000 deals and a million dollar deals, $200,000 deals, generally last ticket items, right, and the ones that typically get approved at the top, most levels, even CFOs or CEOs, right? So when you do these large deals, you realize that, you know, you have to understand their process, because every company is unique, every region is unique, and within every region, every company is unique, and you know, just soaking all of that information into your sales process, your product, your marketing, everywhere, is extremely important for long-term success.

Teja (13:55):

So as like, the sort of LLM space has matured and maybe hit like, the consumer market over the past couple of years, how has that kind of impacted like, your company, and future outlook, and opportunities for growth?

Adit (14:12):

So, you know, we got first introduced to LLMs with the word models. And of course, you know, we were also…I don’t know if you know this, but OpenAI, Sam Altman, you know, actually kind of had the first group of testers trying out GPT-2, 2.5, something like that, back in 2020, right? And, you know, it was open only to YC companies to, you know, come into, (Teja: Right.) yeah. And we are a YC company in this space, so we, you know, we raised our hand, and we got some access. So we’ve kind of known about this, you know, this thing is coming for quite a while. We’ve been working on it ourselves for quite a while, right? And I think one of the biggest things that has happened, especially with ChatGPT, is I can tell you that the technology that you see here, of course, it’s matured way more than what it was, even a year ago, right?

Adit (15:08):

The final product, right? For the final experience that you see today with ChatGPT, right? But it was able to do like, a good percentage, like 90% of what you see today, even a year ago, right? (Teja: Wow.) And at that time, when we used to, so we built our own. So we built our own LLM, called it WorkLM. It’s a 7 billion <unintelligible> model that we’ve, you know, kind of built, and we kind of, we used to show this to our customer back then, enterprise customers, and they’d shoo us away <laugh>. They were like, “Okay, you know what? You can’t be generating content. You <laugh> can’t be generating text on the fly, not in responses. You know, this is, this is some bull, right?” (Teja: <Laugh>.) So now, the good thing is with ChatGPT, you know, nobody asks those questions, right? (Teja: <Laugh>.)

Adit (15:54):

<Laugh>. But yeah, but you know, we’ve kind of known this is happening, this is gonna happen. But yeah, credit to the guys over at OpenAI, you know, to kind of finally bring it in a way that people can use and appreciate the technology. So yeah, it’s accelerated our business like crazy, to be very honest. (Teja: Yeah.) The growth has been, you know, 3x, and you know, I think especially with the backdrop of cost savings and, you know, efficiency plays across the U.S. and Europe, you know, because of the markets and high interest rates, it has been the perfect time for us, because people have more appreciation on the technology, and they wanna save costs. That’s exactly what we do, right? We help you automate tons of queries that keep coming in and suck up people’s time, doing same things again and again.

Adit (16:47):

And I guess, where they can spend that time in much more valuable things for the organization, right? So you know, IT help desk automation, HR help desk automation, finance help desk automation, many, many other use cases. You know, now we are able to, and they just sits well right now, ‘cause everybody’s talking cost saving and efficiencies, and everybody trusts the technology, automatic. I don’t need to get your trust. A year ago, on generative AI, you literally just say, you know, “You’re bullshitting, right?” (Teja: <Laugh>.) But now, you know it works. So like, both of the things that have happened for us are amazing and accelerated our business like crazy. Yeah.

Teja (17:29):

Yeah. Totally. I bet there’s so much less education required now. It’s like, it’s part of the overall understanding of, especially like, I think non-technical buyers too. They’re like, “Oh, okay. Like, we now have intuitively carved out some budget to do this,” (Adit: Yep.) “and accelerate our business.” That’s really cool. When you think about kind of scaling your company and hiring and building your team, like, how are you able to like, you know, you guys have AEs all across the U.S., probably go-to-market teams in Europe, in the Middle East. Like, how do you make sure all these, you know, engineers in India, how do you make sure all these cultures kind of are able to unify under like, Leena AI’s company culture? Is that something that you think about?

Adit (18:21):

Oh, absolutely, Teja. So there are a set of values that we have that are must-haves for people at Leena AI, right? After those set of values, we are pretty flexible in terms of letting people do whatever they want, right? Because there’s some things that are not acceptable, that are not at all acceptable at Leena AI. Some things that are very much promoted at Leena AI, and that you have to, you know, do like, respect your colleagues, for example, right? So there’s some, there’s a list of things you do, there’s a list of things that you don’t do, which is a part of the values and culture statement at Leena AI. So we make sure that those are met. After that, you know, we are open and appreciative of everything that anyone wants. So you know, people in the Middle East, or people in Europe, or people in the U.S., or people in Southeast Asia, all of them have different backgrounds, cultures, preferences, and we are open to everything. But the basic things of Leena like, don’t be an asshole, right?

Teja (19:25):

<Laugh>. I feel like that’s, maybe that’s intuitive, but to me, that seems not intuitive. Like, how did you come to that approach? Is that something you just grew up with, being very tolerant?

Adit (19:36):

So the basic fundamentals of who we want to work with, so, you know, we realized, and this kind of changed because, you know, I think the culture of the organization is very malleable, and it changes over time, right? (Teja: Right.) So when you’re small, it’s a family. It’s group of friends, family, or, you know, want to do something big and all of that, right? And then like, 50 people, and then suddenly, you know, it’s still a family, but a  larger, extended family, (Teja: Yes <laugh>.) and then, you know, basically aunts and uncles now <laugh>, (Teja: <Laugh>.) and then a hundred, alright, and then a hundred-fifty, two-hundred, three-hundred, you know. Four-hundred, which we are right now, you know, there have to be some set of things that we know make the world a better place, right? So for example, we know that we don’t want to, if you’re gonna spend 12 hours working, or 10 hours working, or eight hours working, however, number of hours work, 12 hours, somebody might work seven hours, whatever.

Adit (20:35):

But whatever number of hours you’ve spent working at Leena AI, you need to ensure that you’re enjoying it, right? And our basic set of values say that people don’t enjoy working with assholes, right? (Teja: Right.) So the values are basically making sure that everybody enjoys their time, and they want to spend time here, right? That’s the set. That’s it, it’s not like a long list of many things. It’s like, well, things on both sides, the “dos and don’ts”, right? (Teja: Yeah.) And everything else we are pretty accommodative of, as an organization.

Teja (21:12):

That’s cool. So, okay, so you work a lot like, 12 hours a day, probably six, seven days a week?

Adit (21:22):

Absolutely <laugh>.

Teja (21:23):

Okay. How do you feel if somebody in your organization doesn’t work that much? Are you okay with that? Like, how do you

Adit (21:32):


Teja (21:33):


Adit (21:34):

Yeah. We have 400 plus people at this point. Like, I understand and respect the fact that, you know, people, everybody does not, you know, want to just make or spend 14 hours with their colleagues or 12 hours with their colleagues, and that’s, that’s completely okay.

Teja (21:51):

Were you like that in the early days?

Adit (21:54):

No. (Teja: <Laugh>.) No <laugh>. So when we were 20 people, I would not like this at all.

Teja (22:02):

Really? So, okay. You are, you’re probably like, “Hey, if you’re not grinding 12 hours a day like, what are you doing?” Yeah.

Adit (22:10):

Absolutely. Yeah, yeah, yeah, 100%. Like, I used to hold myself to 14, 15 hours a day, seven days a week, and then everyone around me, very, very high bar, as well, the first two years, right? And then after you know, now we’ve grown a lot, right, and at different stages, different things work and, you know, and are needed for the organization. So leaders, founders, everyone has to change and understand that, as you grow.

Teja (22:40):

Mmm <affirmative>. That’s such a mature outlook. Like, how did you sort of develop that over time? Like, how did you realize like, okay, we need to have a different approach. I can’t just grind everybody 12, 14 hours a day. Like, how did you kind of realize that?

Adit (22:56):

Absolutely. One thing that, you know, I’m really proud of, and one thing that we, I think we do well at Leena AI at least, is we have strong opinions, but very loosely held, right? So, you know, let’s say we are growing, we are at that 100, 150 people mark, and you know, we are asking people to grind, grind, grind, and, you know, people are. Certainly there’s hydration, you know, you have that, you know, people talking about burnout and all of that, so, you know, once it happens once in surveys, it happens twice, and, you know, then you have to take a hard look. You cannot ignore things like these, and I think then you study the market, you understand what other people did, what other successful companies did throughout their journey.

Adit (23:38):

And what I’ve realized is, you know, nobody can ever, you know, keep doing this. You can’t have all of your 400 people grinding, right <laugh>? (Teja: <Laugh>. Yeah.) So yeah, once you realize that and you understand that, then that’s fine, right? So yeah, I think so we kind of just, actually pretty interesting thing in life. Love for you to hear it, and other people to hear it, as well. So what I, and what we at Leena AI, is that, if two people with the same goal, two intelligent people with the same goal, without egos, come to a conversation to make a decision, it is impossible that they arrive at different conclusions. (Teja: Mmm <affirmative. Mmm <affirmative>.) You have to say it “without egos”, and you have to say “with the same goal”. So the goal has to be the same, which is probably, in this case, take Leena AI forward, and you know, and you have to do it without your ego. It does not matter whose idea is this, who’s gonna benefit, whatever it is, right? If you take those two things, and you do them right in every decision, you’ll always arrive with the right one.

Teja (24:47):

That’s tough.

Adit (24:47):

The decision might even be that, “Hey, both of the ideas are great.” (Teja: Right.) “Let’s do an A/B test, right? (Teja: Right.) Decision might even be that, but I’m saying you’ll always arrive with the right decision. So I think this has served us well, and this continues to serve us well, so maybe there’s something for the listeners to also, you know, ponder about, and try, and see if it works for them.

Teja (25:14):

Yeah, totally. And it takes some of the pressure off of needing to find the right answer all the time and making sure this is the way. Yeah, that’s so cool. So do you believe in burnout, personally? Like for yourself? Or do you not experience that?

Adit (25:30):

I generally don’t, because you know, I love what I do. I absolutely, I would not change a thing in my life at all. So yeah, nothing. So that’s why I just love what I do. So that’s why, you know, the badges, the golds, the greats, everything. So you know, like, I can keep doing this for another 10 years. I won’t complain. But I do realize that people need breaks, and that’s completely okay.

Teja (26:02):

Yeah. Have you thought about like, why you personally don’t need to? Like, what about you makes you like, able to sustain like, a very high pace?

Adit (26:14):

So, well, I kind of trained myself, not knowingly, but unknowingly kind of got trained on this. So if I look back for my JE preparation, for people who are listening and who are not from India, <unintelligible> exam, the JE is an exam to get into IITs prestigious technology institute in India. So, you know, there’s like, a million people who take that exam (Teja: <Laugh>.) and you know, you have acceptance at over 0.1%, something like that, (Teja: Yeah.) so like, it’s extremely competitive. It’s extremely tough to get in. Now, the fun fact here is my dad is from IIT Delhi, and you know, when your dad is from IIT Delhi, you know it, Teja, you know, what happens to the kids. (Teja: Yes.) So in 10th standard, you know, after I completed my 10th standard, 11th and 12th standards, or basically high school, was an all about cracking that exam, right? And I, you know, I’m not joking. I used to study 14 hours a day flat for like, 600 days. I studied, I’m not joking, I studied 14 to 16 hours a day, every freaking day, for more than 600 odd days. Yeah.

Teja (27:34):

<Laugh>. And then you probably got like, a positive reinforcement, ’cause you went to IIT, and so you’re like, okay, this is the way like, to do it. Like, if I wanna do anything, I have to do this.

Adit (27:49):

Yup. So that’s exactly what, you know, what you just said is exactly what I just told someone like, two hours ago, right? After you put in that much amount of effort, and it works, the positive reinforcement, you know, just makes you understand that if you should put your heart to a knee, do whatever, you know, you need to get done, or you get whatever you want. So, you know, that was great positive reinforcement, and that’s why I kind of got trained on this.

Teja (28:18):

Yeah, totally. So do you have any like, kind of personal habits? Do you take care of health, things like that? Or do you feel like the work itself kind of brings you energy and sustains you to do more?

Adit (28:35):

The world does sustain me. It gives me energy and sustainment. But yeah, I do like to, so one thing I’ve realized, I’m not a gym kind of a person. I’m also not a running kind of person, but I like to take up sports whenever I can, whatever I can, right? So be it, you know, football, be it cricket, squash, something I like, and of course, you know, you can’t do a lot of these when you’re working, you know, 12, 14 hours a day. So you kind of just figure out how to put them in your schedule, whenever you, and however much you can, and then you run with that.

Teja (29:11):

That’s awesome, man. Your parents must to be like, so proud of you. You know, this is like…

Adit (29:16):

I can only hope <laugh>.

Teja (29:18):

<Laugh>. I’m sure they have told you. You know, but our parents, they don’t say that sort of thing, (Adit: Yeah.) you know? Yeah. It’s just a thing. So that’s so cool. Do you keep in touch with your IIT classmates who, you know, maybe didn’t go the entrepreneurship route, and do you have an opportunity to work with them at Leena AI, maybe hire them, and that sort of thing?

Adit (29:41):

Yeah, so a lot of IIT folks are actually working with Leena AI. I think there are entrepreneurs here at Leena AI, because, you know, our VP of engineering is essentially our <unintelligible> from IIT. (Teja: Yeah.) You know, he actually started his own company with another person, who’s also leading one of our products, and you know, they were way ahead of their time in their startup. They’re doing something in VR analytics, right? (Teja: Wow.) Of course, VR did not take off, so VR analytics did not take off, right? (Teja: Right.) So they joined forces with us back then, and of course, they hold a lot of equity in like, ESOPs and Leena AI, as well. So yeah, I think they’re equal to us. They’re entrepreneurs and, you know, they have a good amount of say in Leena, and what we do here. So, yeah. And one of my junior leads are one of our regional sales teams as well. So we have a lot of IIT folks doing their own entrepreneurial journeys with us at Leena AI, itself.

Teja (30:43):

That’s cool. Yeah. So like, you know, so how do you create an opportunity at Leena AI to give, you know, these entrepreneurial, innovative minded folks and up like, kind of white space to go and create?

Adit (30:58):

I think what we do validly at Leena AI is align goals. Like, okay, you know, we need to build this product, for example, just making an example, and this is well…or wait, we align goals, which means we say, “We need to solve this problem for the customer. This is what the customers are saying, right? How can we solve it? Can we solve it? Should we solve it?” Right? And once we come to the fact that yes, should we solve it, yes. Should we solve this? After that, you know, it’s up to them, you know, the product engineering team, to decide how, you know? Then we don’t get in, and we always don’t try and, you know, dictate, “No, this is the product that you’re gonna build,” right? Then you can do whatever you need to do, or, you know, brainstorm goals, research on the internet, do whatever you need, go talk to more customers, create prototypes. We give them a lot of freedom to do whatever they think is right. Of course, it should meet the end goal of solving the customer’s problem.

Teja (32:03):

Mmm <affirmative>. So, when you guys think about like, you know, your seed round, your Series A, your Series B, typically that’s preceded by like, some revenue growth, but now you’re then ramping your expenses aggressively, right? Do you, as an entrepreneur, probably somebody that has, I would say maybe a thrifty and frugal mentality initially, how did you kind of shift to being venture backed CEO? Was that scary at all?

Adit (32:37):

No, absolutely. I think we were extremely a bit positive, before we did our you know, Series A, right? We ran the company almost like that from Series A through Series B, because it was like, a 10 months difference between October, 2020 is when we did our Series A, June, 2021, we did our Series B, right? Not even ten months less than that, right? Seven, eight months. So we had actually grown our revenue 3x between that time period, right? (Teja: Wow.) So I think there was definitely a shift, because we had certainly had 40 million dollars in the bank <laugh>. So but I do things, and for people who are gonna do this for the first time, right? It’s important to know that when you get that much amount of capital, you know, you shift your mind, and you kind of run toward the other end of the pendulum, where you probably start spending much more money, right, than needed.

Adit (33:30):

I think it’s important to be very, very frugal and run the business like that, at least for a few quarters after you do any large round, because it kind of keeps you grounded, it keeps you close to the reality, right? And especially, in an upmarket like 2021, 2022, early 2022, you know, it’s easy to get carried away that, you know, you can, you’re gonna get, anyway, everyone is raising money. So even if you grow 1x, you’ll not do 110% NRR, you’re gonna get money, right? So you kind of forget that, you know, you should focus on the better number, focus on profitability, you should focus on past growth, yes, but with those profitability metrics in mind, right? (Teja: Mmm <affirmative>.) So I think for the people who are gonna do this for the first time, you should raise money.

Adit (34:24):

There’s no question about it, right? If you wanna take a large chunk of a big market, you need cash from outside, right? But, you know, always remember that, you know, growth has to have, has to be coupled with the profitability mindset. You don’t need to be profitable. I’m not saying you have to be profitable from day one, but you know, you have to kind of have that in the mind, so you are at least tracking, we’re at least talking about it every month with the board and with everybody in the team, and everybody knows that that’s important. And we have to look at that, because that will, itself, you know, help you spend 20, 25% lesser and keep the business much healthier. One of the things that I’ve realized from my peer group, and thankfully we got saved at Leena, because we were more frugal than others, to be honest, but one thing that, you know, happened with a lot of, you know, my friends who raised a lot of money, you know, a hundred million, 150 million, it kind of, the money kind of changes your frugality.

Adit (35:22):

You forget the frugality, and you start spending, and you go to such a high burn that it’s tough to come back down when, or you have a very small runway left at the end of it, right? So I think people should just be like, people who are gonna do this for the first time, should keep that in mind and then, you know, always have that profitability or a better number in front of you, so that, you know, you should scale, you should spend money, you should hire people, you should scale 100%, but keep that number in mind while doing all of this.

Teja (35:57):

What’s something that you like, what are a couple of things rather, that you wish you kind of knew maybe back in 2016, 2015, when you guys went to YC, that you now understand today?

Adit (36:09):

One thing that I wish, you know, I knew back then, was definitely the fact that, you know, I need to spend more and more of my time in people management and hiring, right? And then leaders will have to do that, and like, easily, you know, when I’m telling you this easily, that culture needs to change as you grow, right? If I knew that five, six years ago, and if I knew that, you know, hiring is gonna take up a lot of time, and you should keep talking to people all the time to find the best folks. I think, you know, when that time comes for the transition, because you certainly raise around, and you have to, of course, hire a few folks, right? What happens is, it takes time to switch gears, right? It takes time to switch.

Adit (36:56):

And nobody likes interviews, taking too much interviews, right? I hate taking interviews, so I don’t hate it, but like, if they become more than, you know, three a day, then you know, I don’t like it, right? And I think that’s extremely important from you know from an understanding perspective. You know that you have to spend this much amount of time with people solving their problems and in hiring, you know, for engineers, specifically. It seems like a time suck when they start doing it, but it is going to take time as you grow as a company,

Teja (37:26):

Hiring is so important, and it takes time, but you get like, two interviews, and you’re like, fuck it. Like, let’s just do it. You know? I just, that’s how I am. It’s…

Adit (37:37):

Absolutely. And so, you lose patience, and you have bad hires, (Teja: Yes.) and they’re not culturally fit. Sometimes they’re not even, and when you do blitzscaling, when you do a large round, and then you wanna, you know, hire like, 200 people, there’s so many wrong hires, and we’ve done that. Like, I’ll be honest, like, we’ve made bad hires ourselves at Leena AI, and just because, you know, people are just, they’re taking 18 interviews a day.

Teja (38:02):

Yes, totally. You just get fatigued, you know, you’re not picking up on tells that you would, if you’re doing one interview a day, maybe two. Yeah, that’s totally true. Awesome, man. Well, dude, thank you so much for your time. This was a great conversation, and you know, we just did our Series A last year, so for me, I’m like, learning so much from this conversation, so it’s been awesome.

Adit (38:27):

Absolutely, Teja. Thank you so much for having me, and I hope this was useful.

Teja (38:32):

Where could people find you and your company on the internet? You’re gonna get a lot of info, I’m sure.

Adit (38:38):

Oh, absolutely. And you can find me on LinkedIn. I go by my name, Adit Jain, and you can just put in “Adit Jain, Leena AI”, and you’ll find me on LinkedIn, and our website is of course http://www.LeenaAI. (THE FRONTIER THEME FADES IN)

Teja (38:52):

Adit, next time I’m in Delhi, hopefully soon, I gotta come find you guys, and maybe we’ll go hiking in the Himalayas, if you can get a spare day or a weekend, I’d love to do that.

Adit (39:03):

Yeah. Or in California.

Teja (39:05):

Or California, yeah. Heck yeah. (Adit: Yeah.) Totally. Awesome.

Faith, via previous recording (39:09):

Thanks for listening to the Frontier Podcast, powered by We drop two episodes per week, so if you like this episode, be sure to subscribe on your platform of choice, and come hang out with us again next week, and bring all your internet friends. If you have questions or recommendations, just shoot us a Twitter DM @the FrontierPod, and we’ll see you next week. (THE FRONTIER THEME ENDS)

Teja (39:40):

Edit it, cut things up, chop it up, that sort of thing so you can be casual.

Adit (39:45):