Arjun Pillai On Selling A Company To Zoom.info And Raising $20 Million To Build An AI Sales Engineer To Maximize Go-To-Market Efficiency

Arjun Pillai’s journey from a small village in Kerala, India, to becoming a successful serial entrepreneur in Silicon Valley is nothing short of remarkable.

With a deep passion for problem-solving and an unyielding entrepreneurial spirit, Arjun has built and sold multiple companies, navigating the challenges of bootstrapping, fundraising, and acquisitions along the way.

His latest company, Docketai, has attracted funding from top-tier investors like Mayfield Fund and Foundation Capital.

In this episode, you will learn:

• Arjun Pillai’s entrepreneurial journey began at 23, with multiple failed products leading to eventual success.
• Arjun’s first venture thrived on a lean budget, with a $200 monthly salary in India sustaining his early efforts.
• Arjun’s first successful product launch happened by chance, demonstrating the power of organic growth and unexpected opportunities.
• Arjun learned the hard way that securing investor commitments requires written agreements and strategic timing.
• Knowing how investors think can significantly improve your fundraising process.
• Arjun advises entrepreneurs to prioritize long-term business growth over planning for an exit.
• Both of Arjun’s successful company exits were driven by organic interest rather than a deliberate process.

 

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About Arjun Pillai:

Arjun Pillai’s work experience includes being the Co-founder & CEO of Docket Inc. since August 2023.

Arjun is also an Investor & Advisor at Chi AI (Techstars ’23), Produx AI (Techstars Seattle ’23), Siemba, EventHQ, Greenikk, and Bluehour, with roles starting in various months of 2023 and 2022.

Additionally, Arjun has been an Investor at Factors.AI, Pupilfirst, and Inflection.io since 2022 and 2021, respectively.

Arjun Pillai received their Higher Secondary School Leaving Certificate from Good Shepherd Public School from 2004 to 2006.

Arjun then went on to pursue a B.Tech degree in Electronics and Communication Engineering from Cochin University of Science and Technology from 2006 to 2010.

Additionally, Arjun has obtained certifications, including being a Graduate of Startup Chile from Corfo in 2014, a Graduate of the Blackbox Connect Program from Blackbox Accelerator, LLC in 2013, and a Graduate of Microsoft Ventures Accelerator from Microsoft in 2013.

Connect with Arjun Pillai:

• LinkedIn
• TheOrg
• Crunchbase
• F6S

Read the Full Transcription of the Interview:

Alejandro Cremades: All righty. Hello, everyone, and welcome to The Deal Maker Show. So today we have a very exciting founder that they you know is joining us.

Arjun Pillai: Thanks a lot Alejandro for having me. Excited to get this going.

Alejandro Cremades: He’s a founder that has done it multiple times, you know a founder that really understands what he means to scale and to build something from nothing, and then also to get it all the way to an exit.

Arjun Pillai: Yeah, I’m originally from Kerala, India.

Alejandro Cremades: We’re going to be talking about all of that good stuff you know from the first round you know experience that he had to going through you know through the motions of going through several acquisitions

Arjun Pillai: it’s ah I grew up in kind of a village. It was a pretty agricultural place. I mean, it was my childhood was a lot of games. you know I played a lot of cricket, which is normal in India ah for people who are unaware of the game cricket.

Alejandro Cremades: ah for his previous companies, and right now he’s on a rocket ship. So without further ado, let’s welcome our guest today, Arjun Pji.

Arjun Pillai: um Yeah, a lot of cricket, a little bit of studies. I was decent at studies.

Alejandro Cremades: Welcome to the show.

Arjun Pillai: Nothing big happened, right? I come from a middle-class Indian family. I have an elder brother and me.

Alejandro Cremades: So originally born in Kerala, there in India.

Arjun Pillai: to to people in the family, to kids in the family, then grew up ah without, you know i when I look back, the only thing that I have learned in that process is you know how to be frugal, how to be another, how a middle-class family person would grow up in India, that’s exactly how I grew up.

Alejandro Cremades: So give us a walk through memory lane. How was life growing up?

Arjun Pillai: So the memory lane is a bunch of happy memories of being in the family.

Arjun Pillai: Yeah, in in India, we have this joke that goes around that everybody becomes an engineer and then they figure out what to do with their life. um in In India, everybody wants to become an engineer or a doctor.

Arjun Pillai: In my case, what happened is when I was studying in my eighth, ninth and tenth standard, I went to what you call as a technical school. It just meant that on top of all the usual subjects that we were learning,

Alejandro Cremades: So i guess I guess where does the um the whole idea i mean the the whole idea of becoming an engineer, where does that come from?

Arjun Pillai: We also had electronics and computer science as to additional and electrical engineering, I guess. So three different subjects that usually you don’t learn during your school time.

Alejandro Cremades: Where does the um the love from problem solving you know come from?

Arjun Pillai: um I grew very, very passionate about generally, I have always been excited about physics. And then when I saw electronics, I saw electrical, I grew very attached to electronics. So around that 8, 9, 10 time I started becoming here, I want to be an engineer because that’s what I love. So there was a little bit of that. And then on top of that, my brother was an engineer. So there was somebody in the family itself who just became an engineer. So I could look up to and say, oh, OK, you know what? and Being engineer is a good potential career choice.

Arjun Pillai: um And yeah, that’s how we decided to become an engineer. And then, you know, thankfully the ranks and steps came together. So I ended up joining a college not too far from my home. It was like, you know, in eight miles away from my home. So that also worked out.

Arjun Pillai: Yeah, so the first I started my first company when I was 23. At that age, right what I call is you are young and stupid, so you don’t necessarily know what you are getting into.

Alejandro Cremades: So then tell us about you know really becoming an entrepreneur because you were there for a couple of years, but then you know eventually you decided to brownshot into entrepreneurship, but you did it in a very interesting way, you know in a way in which you were just like testing stuff until you know one thing you know came together which ended up being profoundness, but it was not the first try.

Arjun Pillai: And you don’t have the kind of family and kids to take care of. And financial freedom is kind of there because you just came out, so you ah you don’t have mortgages. And thankfully, I didn’t have student loans and things like that.

Arjun Pillai: So it was fairly easy for me to make a plunge into doing something of my own. um i During my engineering time and post that, I always wanted to do something of my own.

Alejandro Cremades: So walk us through that.

Arjun Pillai: Didn’t really know what that meant back in the in the day. Then I was with Infosys. It is an IT services organization for about one and a half years. During that time, three of my batch mates back in college and I, we kind of planned, hey, let’s do a company.

Arjun Pillai: and That’s how the idea of a company came together. and In 2012, I resigned and started this company. To your point, the first company was a lot of ups and downs. um We built like four products in the first two years. All of them successfully failed. We would build one company or one product every six months. It was all under the same company, the legal entity. We were also bootstrapped because that’s all we knew back in the day. We didn’t know that there was something called as investors. We didn’t know that they could put money into the company.

Arjun Pillai: So the only way we knew was to bootstrap the company, which was how by like taking projects, outsource projects, and then doing it, taking that money, and then you know trying to build a product out of it. Since we were also super young, we didn’t need a lot of money to live. So my salary for about, I think, two and a half, three years in the first three years of the journey as an entrepreneur was $200 a month.

Arjun Pillai: Again, $200 in India goes a little bit further than $200 here in the US, but it still was a little lower for even even India. But we were happy. you know It was almost like ah an extension of men’s hostel for us. So it was fun. We didn’t think of it as a failing, right? We just thought, okay, next one, next one, next one. And the fifth product became a sales intelligence tool.

Arjun Pillai: ah for listeners who are aware of this company called Clearbit or Zoominfo. It was kind of like those two companies, but ours was before Clearbit. This was 2013. So that’s how we ended up in that product, and that product kind of became successful.

Arjun Pillai: Yeah, it ah it was interesting. are That product launched, it was accidentally launched. The story goes like um we were sitting inside our apartment. All of everybody lived in the same apartment because we didn’t have money, so everyone was sharing.

Arjun Pillai: 8.35 PM, we saw that the traffic on our website was going up. And the website was in such a really bad, atrocious state. Nobody would understand what we what we were doing by looking at the website.

Alejandro Cremades: So at what point do you guys realize, hey, I think that out of all the ones that we’ve tested, this one you know really makes sense to to go at it with.

Arjun Pillai: Then what we saw from Google Analytics is that people are coming from this website called as Product Hunt. So what happened behind us um There is an investor called Dave Ambrose in Silicon Valley. I have never met the person. He somehow stumbled onto our website. And on the website, there was a slider between $2 to $30. Basically, my team asked me, how should we price this? And I said, I have no idea how to price this. So let’s put a slider between $2 to $30, let people pull it wherever they want, and then click on Pay and just pay for the product.

Arjun Pillai: you know it’s probably a bad idea but they felt that it was an interesting pricing strategy and so he posted it on twitter saying that hey startup is trying out a new pricing strategy here or pricing you know analysis or experiment here Rand Hoover, who was the co-creator of Product Hunt, saw that tweet. He came to the website, and he saw that the product was interesting. So he went back to Dave on Twitter and said that, hey, Dave, the product is also interesting. Why don’t you post it on Product Hunt? We didn’t know any of this, and Dave posted it on Product Hunt, and we got launched.

Arjun Pillai: So that’s how we got accidentally launched. But in the next 30, 36 hours, we onboarded 2,000 people came to the website. We kind of manually using chat onboarded 800 of them. And out of those 800, there were like a few PR people, ah you know writers. They wrote about the product in CNET, GigaWomb, LifeHacker, LifeHacker Russia. And kind of in the next two, three weeks, we went up from 800 users to 4,000 users.

Arjun Pillai: So to answer specifically to your point, right when that organic pull happens from the market, which never happened with our previous products, this was the time we were like, okay, we are probably onto to something here.

Arjun Pillai: Yeah, so two and a half years we were bootstrapped and then we decided, okay, you know, it’s time. Let’s go out and try something. I made a bunch of mistakes. The first mistake that I did was I started racing in October timeframe, October, November timeframe, which is probably not the best time to start raising because of the vacation, December, et cetera come through.

Alejandro Cremades: So I know that, they obviously, to to to to support that growth, you know you guys looked at, the as well as raising money.

Arjun Pillai: I got two investors to, I was planning to raise $400,000.

Alejandro Cremades: And I know that the first time, you know the first rodeo was a not a walk full of roses.

Arjun Pillai: I got two investors to commit 150 and 150 each. And I was like, OK, I’m at 300 K.

Alejandro Cremades: So what happened during the the fundraising efforts here?

Arjun Pillai: Let me find a few more value added angels and I’ll close the round. But the mistake that I did was. um I didn’t make them sign a safe or a convertible note. And December went through, January came, and they were both like, oh, we didn’t commit. We were just seeing that we are interested. So my 300k soft commit went to zero. But even before that, I had to go through 65 people. 65 people said no to me. you know They would take a call. They’ll be like, yeah, this is interesting. Let’s do another call. So I went through like 65 meetings, and all 65 were no.

Arjun Pillai: The 66th person said yes. And then this commit went back to zero. And then I had to restart. And we ended up raising $380,000. And that was enough for us at that time. ah So the first rodeo was certainly not a cave walk, but learned quite a bit.

Arjun Pillai: Yeah, simple things like when somebody is committing, make them commit on a piece of paper, right? You should know the instrument that you are looking at. And then once you have somebody saying, yes, I am interested, I am hard committing some some number, use your instrument. Could be safe, could be a convertible note, whatever you are using.

Arjun Pillai: Just make sure that you get it on a piece of paper. The second thing is if you are doing your fundraise, do it in a statistical way where you have everybody coming at pretty much the same timeline.

Alejandro Cremades: What is the biggest lesson, your biggest takeaway you know from that besides you know timing and seasonality and all of that good stuff?

Arjun Pillai: You shouldn’t be serializing the conversations, right? You should be like, OK, let me talk to person one, then person two, then person three. It should be more like I’m bringing everybody to the table almost at the same timelines.

Arjun Pillai: The more people that there are on the table, the better deal I will get. You know, The third important thing, which probably is over a period of time I learned this, it’s very important for entrepreneurs to understand the math that investors are doing in their head, the pattern matching that investors are doing in their head, and where they are coming from. If you can get into their shoes, then your fundraising process is way easier.

Arjun Pillai: But most of the entrepreneurs don’t know that. And again, first time entrepreneur as an entrepreneur, I also made that mistake. If you get a chance to sit down with an experienced deal maker, then ask them, hey, what does that rationale look like? What does that thesis look like? Why do people care about ownership percentage? Things like that. So those are some of the learnings.

Arjun Pillai: Yeah, so we were in the process of building out the company. We started as four people grew to seven, 12, 32, 52, 72. So the company was kind of scaling pretty well. We became profitable. I think we were about 39 people when we became profitable. And then we were like, yeah, we have money. We will grow. So we will kind of started burning a little bit more.

Arjun Pillai: um I got a fully committed pre-series term sheet for the company. At that time, Full Contact who was an existing strategic partner who was buying data from us.

Alejandro Cremades: So at what point does a full contact they come knocking?

Arjun Pillai: They were like, hey, we want to buy out the company because the combined entity has a lot of value. And back in the day, Full Contact was doing extremely good. they had raised um At that time, I think they had raised about $30 million dollars or something so far, and they were just going to close their CDC for about $25 million. dollars Again, CDC in 2016, $25 million is pretty good. ah So they had a lot of traction behind, and they were doubling revenue almost on a yearly basis. So it totally made sense to sell the company. And this happened in 2016. So we ran that company for four and a half years.

Arjun Pillai: And while I sold the company, i later I realized that that was the first product exit in the history of my state. It had never happened before. So you can imagine the nacency of the ecosystem. But it became kind of like a milestone event um in the in the in the state. It was not a big outcome. It was single digit million. It’s a legally undisclosed thing. So I cannot tell the numbers, honestly. But ah yeah, the outcome kind of changed our lives, the founders, but also the larger ecosystem.

Arjun Pillai: yeah

Arjun Pillai: Between full contact and Incent, there is nine months where I was actually consulting. um I consulted for a bunch of sales tech companies, smart tech companies, data tech companies.

Alejandro Cremades: That’s amazing. So then obviously in this case, you guys say they did the transition, the vesting and resting in full contact for a little over a year.

Arjun Pillai: up wanted to kind of learn the trick of the trade of consulting, wanted to do better in sales.

Alejandro Cremades: And then eventually the idea of ah basically Incent the AI comes also to you.

Arjun Pillai: So did that. And during that journey is when I realized the real time conversations in B2B was becoming more and more apparent to me.

Alejandro Cremades: Once an entrepreneur, always an entrepreneur. So tell us about how you know did you think about this next day you know chapter you know and and why you thought it would make sense to go at it again with Incent.ai.

Arjun Pillai: And I was like, there is certainly a better way to do real time conversations. That’s where Incent, the name comes from intent and consent of the buyer. So the whole idea was a buyer wants to get information from a B2B company. It is very difficult today. They don’t want to submit a form and then wait for you know five days to get information. So we wanted to build a B2B account-based buyer-centric conversational experience for companies. That’s what we did. um and There was drift.com.

Arjun Pillai: um was kind of, they had a conversational platform which was more chatbot oriented back in the day. And we were there and there’s another company which is still around doing good, Qualified.com. ah So three of us were kind of in that realm of account based marketing advanced B2B chat application. ah That’s how Incent came together end of 2018.

Arjun Pillai: It was a B2B SaaS model. So it was based on, there was a platform pricing for the underlying conversational platform, which included the integrations, setting up of the process onboarding and all of that.

Arjun Pillai: And then there was a per seat pricing. I think ah there was 10 seats that were baked into the basic platform fee. And then if you wanted to have more seats, then you would obviously pay more money.

Arjun Pillai: that’s ah that was the It was true SaaS simple model.

Alejandro Cremades: So they tell us about the um the monetization strategy here.

Arjun Pillai: There was no pro services or things like that.

Alejandro Cremades: What was the business model? How did you guys end up making money here with Incent.ai?

Arjun Pillai: Yeah, so the second company, we actually didn’t raise 4 million, we in total raised 2.7 million, but you’re right that the fundraising process was way more easier.

Alejandro Cremades: Now this time around, you guys were ah quite successful in raising money.

Arjun Pillai: The first round, when I said that I’m starting the company, my previous investors who all made good outcome with my first company, they all wrote a check almost immediately.

Alejandro Cremades: You know, if you were to compare with the first rodeo, you raised the a little over 4 million bucks, you know, and that was an ultimate same thing. You know, you have um another player swimming for coming knocking here.

Arjun Pillai: I told them I don’t even know what I’m doing, but they were still happy about it. We put a cap on a safe and then they wrote like, I think it was a 4 million cap back in the day.

Alejandro Cremades: Obviously you at this point, you are very familiar with the acquisition process.

Arjun Pillai: They just wrote a check and like, here you go with $300,000.

Alejandro Cremades: So how did you go about things differently, you know, this time around?

Arjun Pillai: And then we also went through Techstars. They put in an additional 120K. So in total, we started the company with 420K. Then ah coming out of Techstars, there was $380,000 that organically came through mentors inside Techstars. We didn’t try to raise. We had that. And then we did a seed round ah led by Emergent Ventures. ah That was $1.9 million.

Arjun Pillai: So that was the total fundraising at the company. It was way easier to raise the second time around. The big acquisition, again, wasn’t planned. The first time also it wasn’t planned. Second time also I was never planning to sell. I was just continuously focused on the business and how to grow the business.

Arjun Pillai: I had a almost a commitment to my CDC. I had advanced discussions with ah series a a really good investor here in the Bay Area, and I was supposed to come to the Bay Area to meet the investor. um But at that time, Henry Schuck, the CEO of ZoomInfo, who I had known for some time,

Arjun Pillai: I have this habit, it’s probably interesting to the listeners how that conversation, how the acquisition inbound came. I sent an email, I have this habit of when an industry thing is happening, which I feel is relevant, let’s say Alejandro for you, something is very relevant for you. I’ll drop a quick two, three sentence to you saying, hey, did you see this news? It’s very interesting for you.

Arjun Pillai: right or I believe it is interesting for you. So I sent such an email to Henry when I saw some industry news, which I felt was relevant to Zoom in for as a company. He responded back saying, Hey Arjun, that is interesting, but what you’re doing is more interesting. Let’s catch up.

Arjun Pillai: So that is what got the first conversation actually going. And I had received other acquisition offers, but I didn’t entertain any of them. But Henry was different. Zoom info was different. So I took the call. He was very explicit that, hey, you know this is a space that I want to do an M and&A.

Arjun Pillai: um And then it went cold for a little bit. We so we talked October 2020, I believe. It went cold for a little bit of time, and I didn’t push because I wasn’t trying to sell. Then in February, when my CDSA was coming together, ah again, interestingly, I was sitting at my desk doing the work. I got a notification from my product saying someone from Zoom info is on your website. And I said, hey, great to have you from Zoom info. And well hey, Arjun, this is Henry Shaq from Zoom info.

Arjun Pillai: ah the product is very interesting, we should catch up. That restarted the conversation. At that time, it went super fast. In about two months, three months down, the the whole thing was done. That’s how the second acquisition kind of came about.

Arjun Pillai: Yeah, a few things. First of all, don’t build a company to exit. It is fine to have exit as one of your options, but build the company as if you want to build for long term.

Arjun Pillai: I always believe that the best deals come to you, whether it is from investors, whether it is from acquirers, they come to you when you build a solid business.

Alejandro Cremades: That’s in incredible.

Alejandro Cremades: That’s amazing.

Arjun Pillai: So I would put all the focus on building a strong business and funding coming through or acquisitions coming through.

Alejandro Cremades: So how what have you learned about acquisitions? What’s your biggest take? You know, like for the people that are listening that maybe are thinking about, you know, doing M on&A and and getting a bigger player to acquire them.

Arjun Pillai: In all of these cases, I have never ran a process.

Alejandro Cremades: I mean, what do you have to tell them?

Arjun Pillai: I’ve never run a process for fundraising. I have never run a process for acquisition. It always come organically to me. That has been my experience. Focus on the business, good things will happen. The second experience is if you are going through the acquisition process, make sure that you get the right kind of support.

Arjun Pillai: whether it is legal side, tax side, you need to make sure that you have the right support if you’re going through that process. First time I made a lot of mistakes because it was happening for the first time. I didn’t have the right legal support. I didn’t have the right tax support. I probably paid about, I don’t know, $300,000 in taxes to the government, which was which we could have easily saved if I had a good tax person assisting us.

Arjun Pillai: Second time around, I got the best legal support, best act support, and that that turned out to be a really good ah decision. The third and the biggest learning from me after acquisition is once you sell a company, it is not your company.

Arjun Pillai: founders have a difficult time getting this internalized. I also went through this mistake where once I sold my company to full contact, I had an emotional attachment to the company still. That is not the right way to do it. Once you sell the company, it is not your company. You should kind of emotionally and mentally move on from that and start looking at things objectively. So these are probably the three big ones that I can think of.

Arjun Pillai: Yeah, my time at Zoom info was very fruitful. um ah For me, I learned that ton.

Alejandro Cremades: So then obviously, you know, once this acquisition happened again, you know, you stay with Sumi for a little bit and and then, you know, pretty much the same thing, you know, docket.

Arjun Pillai: And in my perspective, even for the company, it was very fruitful, whatever I could do for the company, including launching a new product, doing things with the data side at Zoom info.

Alejandro Cremades: And so docket, obviously third time around, you know, I’m sure that you thought about, you know, things differently and and very much in depth, you know, before you actually pull the trigger, you know.

Arjun Pillai: um But at the same time, you know, and you mentioned this Alejandro, once an entrepreneur, he or she, they always have they always have this feeling of, hey, I want to go out and do this again.

Alejandro Cremades: So what what do you think, you know, like made it so, I don’t know, so appealing to you to to to go at it, you know, on this third chapter?

Arjun Pillai: And I still have the energy, right? I’m 35 now. I still have the energy to build a company. And this is probably the time I am the best networked. I have the most amount of energy.

Arjun Pillai: And with my second outcome, a second exit that happened financially, I’m taken care. I don’t have to work per se. But see but That all gives me a lot of cushion to kind of go out and swing for the fences. right So that’s what docket is all about. And AI was happening so thick and fast in the past couple of years. This is probably the biggest paradigm shift that we will experience in our lifetime. um I mean, we had a couple. right I was studying when SAS was happening, but I was around when mobile was happening.

Arjun Pillai: um I was kind of there when social was happening. But those were, I was still very young to kind of really get used to or make sense out of those trends. But AI is happening when I have the energy, I have the network and I believe it is the biggest paradigm shift that will happen in my lifetime. So it was too good of an option or ah too good of an opportunity to pass.

Arjun Pillai: And on top of all this, I found a problem statement that resonates with me that I understand deeply, and I wanted to solve that. And that’s where Docket comes in.

Arjun Pillai: Same thing. It’s a SaaS product. It’s a platform-based pricing. We have a platform price and a per seat price. Hopefully, over a period of time, the AI is going to enable us to evolve our pricing to something more like an outcome-based pricing or something like that. But today, it is true SaaS platform plus seat model.

Alejandro Cremades: And how are you guys making money a docket?

Arjun Pillai: Yeah.

Arjun Pillai: Yeah, absolutely. so Yes, it was easier this time than the last time. What my experience is, every time it gets easier up to a point, my second company, it was easy to raise my first couple of rounds, this time also the first couple of rounds.

Alejandro Cremades: So then in this regard, the you know you guys also went about it ah differently too on raising money because you’ve raised a quite a bit more than on the last day rodeos and and also from like super heavy, heavy weights.

Arjun Pillai: And I’m sure that as the company progresses, it will get slightly tougher. um When I started the company, the initial idea was, I don’t have to raise, I’m going to put 400, 500k and then run the company for a month and then we’ll see.

Alejandro Cremades: So I’m sure that now, you know having had two exits under your belt, it was it was easy stuff, raising money. you know So how did you go about doing it and why did you take the money from the people you did?

Arjun Pillai: But when I was catching up with my previous investors, all of them wanted to kind of chip back in. And four days after the incorporation, I was sitting on roughly $3 million, $3.5 million dollars in in soft commits.

Arjun Pillai: They were like, yes, we want to invest this money. And I was like, OK, there is good interest here. So let me actually go ahead and do a proper race here. um At that time, Foundation Capital, Ashu Garg and Jaya Gupta, they reached out ah to me out of the blue, actually. I took a call. Ashu and I hit it off very quickly on a call. So the first call was supposed to be 30 minutes. We spoke for 55. And then in 20 days, from nothing to the deal done in 20 days happened with Foundation. So Foundation led the round for five

Arjun Pillai: The total round was $5.3 million. dollars um Founder’s co-op in Seattle, ah Henry Shaq, a CEO, ah Jeff Lunsford, CEO of Telium, Anu Parathwaj, at last same president, Viral, CTO of Six Cents. A bunch of really amazing angels came together to do the 5.3.

Arjun Pillai: Then we found a few pilots, design partners, started to build out the product, delivered the product. We started generating early revenues. ah Mayfield and I have had a pretty long ah relationship. I’ve known Rajiv Batra from Mayfield for a long time, Navin for a long time. That conversation kind of very quickly, I was catching up with Navin and then that conversation very quickly evolved into a CDC conversation.

Arjun Pillai: And I think they moved fast. Patrick ah is my partner at Mayfield. Patrick was amazing. He moved so fast in about three to four weeks time, did all the due diligence and work on on their side. um And then, you know, CDC happened. We raised $15 million, dollars led by ah Mayfield and and Foundation joined in.

Arjun Pillai: The future or with docket fully established would mean that docket has become an AI sales engineer in the organizations where it is assisting the existing sales engineers and existing account executors to a point where the go-to-market efficiency in those companies is so good.

Alejandro Cremades: So obviously, vision is a really big deal here, and it’s something that day I’m sure those guys were banking on, those guys and gals.

Arjun Pillai: Docket is joining the calls, answering the questions, taking the demos, being a full teammate through the companies, and making sure that the B2B companies are operating at super high efficiency.

Alejandro Cremades: So I guess a question for you. If you were to go to sleep tonight and you wake up in a world where the vision of Docket is fully realized, what does that world look like?

Arjun Pillai: that’s ah That’s what the goal would look like in terms of a vertically fully integrated AI sales engineer.

Arjun Pillai: My first advice would be learn validation and validate everything that you want to do really, really deeply.

Alejandro Cremades: so then So then here we’re talking about the future. I want to talk about the past, ah but with a lens of reflection.

Arjun Pillai: The first four products that I failed, the commonality was I did not do proper customer market validation before I built the product.

Alejandro Cremades: So let’s say I was to take you back in time. you know Maybe I take you back in time to that moment where you were you know now thinking about going at it on your own, you know building your own business, you know let’s say maybe 2012.

Arjun Pillai: So today, even even before writing the first line of code, I will do a bunch of validation with the right people.

Alejandro Cremades: And let’s say you have the opportunity of having a chat with that younger Arjun.

Arjun Pillai: So like validation, do validate ah everything that you are looking to do.

Alejandro Cremades: And give you that younger Arjun one piece of advice for launching a business.

Arjun Pillai: So that would be the first advice that I would give.

Alejandro Cremades: What would that be and why, given what you know now?

Arjun Pillai: The second advice is probably. Everybody who you meet, they are smart, take feedback from them, but don’t think that everybody you meet no more than you, which might be true for a very small percentage of the people, but for most people, especially in your business, right, I’m not talking everything. I’m talking about your business. You are thinking about it 24 by 7 all the time. So about that, there is a significant chance that you have a view that is probably right than most of the people that you meet. So here everybody’s input, take that as your input as a founder to process through. Don’t make other others take decisions for you. So I thought

Arjun Pillai: Yeah, I could have done better um you know in in the second one, second point that I just… So these are probably the two.

Arjun Pillai: LinkedIn is probably the best. Just search for Arjun Pillai, and that you should be able to find me. I’m pretty active on LinkedIn. I’m also on Twitter. ah But LinkedIn is probably the best place. And um you can also learn more about Docket at docketai.com or just search for docketai on Google. ah So those would be the two places where you can reach me, learn more.

Alejandro Cremades: I love it. So Arjun, for the people that are listening that would love to reach out and say hi, what is the best way for them to do so?

Arjun Pillai: Likewise, I had a blast. Thanks a lot for having me.

Alejandro Cremades: Amazing. Well, hey, Arjun, thank you so much for being on The Dealmaker Show. It has been an absolute honor to have you with us today.

*****

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