Eswar Priyadarshan On Selling 3 Companies For $575 Million And Working With Steve Jobs

Unmessable Podcast

Born in Bangalore, India, Eswar dedicated ninety-five percent of his time growing up playing cricket, and didn’t apply himself much to school. His parents, both English professors weren’t overly concerned because he did one thing consistently: read. Eswar was fascinated with military history books and read vivaciously about the topic. In many ways, military history played an influential part in how Eswar viewed leadership. Fast-forward to his college days, something triggered in Eswar when he came to the US to study and realized that he’d been given a tremendous opportunity to do something special with his life. During his Corporate America career, he got to launch some epic products including the Adobe PDF search function, which is probably still using his code today.

More impressive though, is his track record as an entrepreneur. His first company, m-Qube, where he led all the technology development and research was acquired by VeriSign for $275 Million and his second company, Quattro Wireless, was acquired by Apple for $275 Million. Once the deal was inked and Quattro Wireless officially joined the Apple conglomerate, Eswar directly reported to Steve Jobs for years before his illness progressed. Throughout his professional journey and particularly in working Steve Jobs, he learned a great deal and shared some key leadership insights on the Unmessable show.

In this episode you will learn about:

• • • Working with Steve Jobs
    • Leadership: CTO versus CEO
    • Building a company
    • Exiting a company
    • Managing and scaling a team
    • Raising capital
    • Effective Communication

About Eswar Priyadarshan:

Prior to founding BotCentral (acquired by LivePerson), Eswar was Senior Director at Apple Inc., where he held product and engineering leadership positions on Apple iAd, iTunes Radio and Apple TV.

Eswar co-founded Quattro Wireless, which was acquired by Apple in 2010 for $275 million. He subsequently led the technical integration and transformation of the Quattro platform into the iAd platform.

Prior to Quattro, Eswar was the co-Founder and CTO of m-Qube, Inc. While at m-Qube, Eswar was the leader of all technology research and development. m-Qube was acquired by VeriSign for $250 million in April of 2006.

Prior to m-Qube, Eswar was VP Engineering at Open Market Inc. Before Open Market Eswar was the Technical Lead for Adobe Acrobat. Eswar held various engineering positions at Sun Microsystems prior to Adobe. Eswar holds Bachelors and Masters degrees in Computer Science from Boston University.

Connect with Eswar Priyadarshan:

Linkedin
Twitter

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Full Transcription:

Eswar: I was born in Bangalore, India back when it was a sleepy garden city, very different and exciting these days. As a kid, I probably spent 95% of my life playing cricket, went to a great school, St. Joseph’s Boys’ High School, and I was the fat kid in the class.

Tanya: That’s Eswar Priyadarshan, serial entrepreneur who sold two companies for a combined value north of a half a billion dollars, and one of his acquirers being Apple where Steve Jobs himself endorsed the deal.

Eswar: I grew up being teased and having a label attached to me, and it’s been a thing that’s been with me throughout my life. I guess in some ways has made me a little bit of an outsider inside. I never felt like I completely fit because of the way kids can be when you’re growing up.

Tanya: Very mean, yes, I remember.

Eswar: Yes, yeah, and then the other thing is, apparently, I was very easygoing, didn’t do very well grades-wise. Both my parents were English professors, and so the thing that my father kept saying about me to my mother was, “Don’t worry. He reads a lot. He’ll be okay.” From an early age, I just devoured everything. Somewhere early, early on, it’s going to sound strange but I started to read a lot of military history. I was very interested in history in general, military history, and that love continues to this day. In some ways there’s leadership – my leadership textbooks in some ways have been a lot from the military history side.

Tanya: Wow! That’s super interesting. Just out of curiosity, what subjects were you not great at in school? That totally shocked me, to be honest. I mean, I would think that you would be a total whiz.

Eswar: Yeah, I was bored.

Tanya: That’s it, yeah.

Eswar: I think that was it, and it actually kicked in when I came to the US and realized I had been gifted a golden opportunity to make something of myself. I switched overnight from being total slacker to being all As across the board. In some ways, I guess it’s good in that I feel like I have plenty of time to goof off. I’m very good at goofing off. I’ve had plenty of time to goof off. I’ve tried all varieties of extracurricular activities. It’s good, I think, in some ways to have been young and responsible when you’re young and irresponsible.

Tanya: You certainly made up for it. That’s for sure. You’ve had a significant corporate America career where you’ve launched incredible products. What are some of the most notable products that you built and brought to market?

Eswar: I’d say the biggest one is probably Adobe Acrobat on the web so Acrobat 1.0. I joined the team at Adobe for Acrobat 1.0, worked on search in Acrobat, so when you find something in a PDF file, you can think about me. That’s probably my code running there. Then I really kicked in for making sure that PDF integrated with the web browser and progressive download. Specific patent that I – it gives me goosebumps to this day is, when you download a PDF file and you notice how the text shimmers into – it’s almost like it draws once, and then it draws again. That was an example of some technology we put in to draw the characters the right width to start with and then to get the real font and to redraw them. It’s ways to make PDF work on slow network connections.

Tanya: I mean, that’s unbelievable. Everybody uses PDFs. I use it several times a day, Acrobat. That’s an amazing product to have worked on, and I’m sure you learned a ton. What is your gift or core skill that you really, really excel in?

Eswar: It is a skill and a dangerous thing in that I can listen to many, many points of view and bring perspectives together. It’s dangerous in that people could get spooked in the sense of did he take my idea or not? I’ve actually tried to work very hard to prevent – to provide credit to people wherever possible. I have gotten a lot of patents to my name, and if you look them up, you’ll find a lot of co-authors to every patent. I try very hard to distribute the credit because it does take a lot of people to pull together. Even the idea that I just talked about, a lot of technology, a lot of smart people have to come together.

I’m the person that can listen to a conversation from you and ten other people, and then move the ball forward based on things I’ve heard from different perspectives. An example of that would be I demonstrated the PDF file running in the Netscape Navigator window to the original Netscape team, Marc Andreessen and the original Netscape team when I worked at Adobe. Then I was asked the question how are we going to make this work in the real world? I pulled together a demo. I knew all about Photoshop plugins, so I said what Netscape needs to do, the browser needs to do is support plugins or extensions. It’s a case of me picking up something that we already did at Adobe and bringing it to bear to solve a problem for a small company at that time, Netscape, and moving the ball along. Absent me, would it have happened (probably)? Did I help make it go faster (probably)?

Tanya: That’s super interesting. It’s like Elon Musk where he takes – he goes deep on many different verticals, and then he knowledge transfers. He applies one concept to the next, and somehow, it works brilliantly.

Eswar: That’s very flattering, but yes, something like that.

Tanya: In working to corporate America to your transition to entrepreneurship, how did that happen? What was the prompt?

Eswar: The prompt was I was running our 250 person team at a public company called Open Market. We had a lot of dotcom customers. We were an ecommerce platform. The crash was happening all around, and I just could see that it was – in some ways, if there is – it was a time of great change, good or bad, just great change. I had been noodling with mobile as the next frontier for about a year at that same time. This was 2000, 2001. I thought why don’t I – I mean, I was getting well paid as a public company, but it was like let’s – it’s time to shed the old skin and get out of my comfort zone and see if I could start with a blank piece of paper in the mobile domain given that it was super early. You couldn’t even send a text message from a Sprint phone to an AT&T phone, for example, so it was nutty to even think that that could happen.

I thought, hey, come on. It’s time to get in. I always admired the people who get in – like the super early MS-DOS people or the super early UNIX people, you want to be in there on the ground floor, and stumble around and make mistakes, and be part of the journey of the overall ecosystem. Not just join later on. It was a combination of things, me wanting to get into mobile, me wanting to start with a blank sheet of paper and try my hands at being an entrepreneur, and then a VC firm general catalyst who is seeking almost like an entrepreneur and residence type person to help them with the mobile idea.

Tanya: The first company that you launched was m-Qube, correct?

Eswar: Yes.

Tanya: Okay, so can you talk a little bit about that?

Eswar: M-Qube at its peak was a content – we connected brands to the brand new mobile channel so brands for like Deal or No Deal, the TV voting. A TV show where you could vote on the suitcase or whatever it was started at 49 cents a vote. They bumped it up to 99 cents a vote, and we doubled the traffic. It’s crazy. We had a ton of content providers. It was back in the days of ringtones, so I’ll confess to that as well, ringtones, wallpapers, a ton of mobile content. A good 40% of Singular’s data revenue was going through our pipes. There were a few trusted aggregators in the market. We were called the aggregators, and we were one of them.

In many ways, we were a super-scalable billing platform because a lot of this content would be billed on your carrier bill. The one thing that we did that I’m particularly proud of was to this day, I believe, when you send money to the Red Cross, whatever, using text messaging, that was something we originated with Hurricane Katrina. It was so amazing to watch all the wireless operators in one day – I kid you not. In 24 hours, we lit up this program in the US and Canada where you could – yeah. It was just an idea. It started as an idea in the morning, a watercooler conversation. A lady in our marketing team was saying, “Wouldn’t it be great if people could send money using text messaging?” I knew someone on the carrier side in Verizon. I made a phone call, and before you know it, by that night we were on a conference call letting it all throughout North America.

Tanya: Wow! Do you have any idea how much money has been transacted using that software to date?

Eswar: I know the person who does. It’s called the Mobile Giving Foundation. There’s a ton of charities on that website, and I’m sure my friend, Jim Manus, knows the answer to that question. There’s a lot of money that’s gone through that platform. It’s a very viable – it’s a good thing.

Tanya: Oh, absolutely, the impact that you had by facilitating that ease to donate is unbelievable. Your entrepreneurial path has been really fascinating. You built m-Qube, which got acquired by Verisign for 275 million. Then your next venture, Quattro Wireless, got acquired by Apple for the same amount, separate company 275 million, which seems to be your real sweet spot. Then what was so fascinating about the Quattro deal was that – and really, a lifetime experience. Steve Jobs was directly involved in acquiring your company, and then once the deal was inked, you reported directly to Steve Jobs. When you were meeting with Steve pre-acquisition and going through the M&A process, what were you thinking? What was your mindset at that point?

Eswar: The interesting thing was I was – we were very confident that we knew what we were talking about with mobile advertising. That was the good part. We had met a lot of ad developers that needed revenue. We already thought of ourselves as a little Robin Hood. We would take money from the rich brands that wanted to advertise and run ads on all kinds of tiny little apps, including my neighbor’s Jewish day school app. That’s what we were there for.

I think we walked in with that perspective. Our first conversation with Scott Forstall I recall was we had a whole presentation and everything. Scott just looked at us and said, “Tell me what’s going on,” and we just shut down our PCs. We used PCs back then, pre-Mac. That’s a whole other story. We just talked about it. We talked about the app ecosystem. We talk about how brands wanted to get onboard and take advantage of this new channel.

I mean, I think I’m almost doing the same play again and again. You take brands. You take the mobile channel. As it grows up from SMS to apps, etc., etc., you just make it possible for that cool content to show up on your devices. It was a very open, free conversation all the way where we had not the main expertise but just the confidence that we were on the right track, and I think that really helped and starting the conversation with Steve. Of course, once you start talking to him, everything goes out the window because he had a unique perspective on just about everything.

Tanya: How did you prep for that meeting? How do you even get yourself in the mental state to walk in confidently? I mean, you might have a real handle on your product, which it sounds like you did. Is there anything else outside of just the know-how of your product that you did, that you practiced, that you – any exercises that you followed?

Eswar: They had a five-hour prep session, which was, with all apologies to those who prepped us, completely useless when it came to Steve because he went off in a completely different direction. It was actually the thing that I didn’t do that almost bit me in the first five minutes, which is I didn’t rehearse at nauseum running our ads on the bad Wi-Fi 3G environment in that infinitely one conference room that we were going to meet it, and so Steve wanted a demo. I sat next to him. I started working, showing him the demo, and just, honestly, I think my thumb was in the way because probably subconsciously I was trying to make up for the fact that the darn thing was so slow. Then Steve said something unpredictable about moving my thumb out of the way, and that’s where we began. I’m still alive. I kid you not.

Yeah, that’s how it goes, right? If I look back I say what was I thinking? Why didn’t I just obsess over every aspect of exactly that? I mean, it’s Steve Jobs. You should be rehearsing your demo and know exactly where to go, what to do, what to show, what to showcase. Go figure. Yeah, maybe it was – maybe we were just over prepared with all this other stuff, which is the basics.

Tanya: Yeah, that’s usually what happens. One of the things that – the saying goes build a company once and sell it. That’s lucky. You’ve done it twice and started several companies, so there’s something about your approach, about your touch, about your involvement that’s different. What has been at the source of your success?

Eswar: I have a very good sense, I guess, over time. It takes some time. Just as part of the ability to integrate different points of view is to understand what the buyer is looking for. Deep down inside, I know culturally, philosophically what the buyer be it a customer or an acquirer is interested in doing to advance their cause. I think that’s what I bring to the table that is different than, yeah, I guess just technology, or banking, or business skills. It’s just that innate feel for – even that LivePerson acquiring my last company, BotCentral, it’s the same thing. I just have a very good sense.

I guess I take the time. I take the time to understand what I’m dealing with, the people specifically, very, very specifically, the people. I don’t know if you are like this. When I visit a new company’s website like if I’m doing M&A or looking up a customer, I always go to the About page and look at the biographies of them. I can visualize their career, where they went to school, where they came from. That’s where my mind gravitates towards, the story. What is their story? How can I help make them fulfill or shape their story?

Tanya: When you start a company, do you have the exit in mind?

Eswar: No, I usually have a space in mind, like a big space, and some notion of wouldn’t it be cool if we pulled that off, like some version of a moon shot in that space. It’s got to be appropriately difficult, I guess. I don’t know how we’re going to get there. It really needs to feel like I don’t know how we’re going to get there. Then it’s fun.

Tanya: That’s amazing. Just to focus on Quattro Wireless for just a second, you had 120 employees at the time of its acquisition, right?

Eswar: Yeah.

Tanya: You got 30% of your company, which was between Boston and New York to move to California with you and their families.

Eswar: Yes.

Tanya: How on earth did you navigate that conversation?

Eswar: That was easy. It was Apple. It was Steve. Peter Oppenheimer, the CFO of Apple, came and visited us in our office. We kept it secret until Peter showed up and talked to everyone, and he was great. “I’m Peter Oppenheimer, CFO of Apple. I’m here to explain how Apple makes money, how you’ll fit into the ecosystem. Will you please come? It will be great if you guys could move to California.”

He said it was going to be 30 days from closing the deal. Will you please keep quiet about it? At least 10 of those 40 that I know of didn’t even tell their spouse for 30 days.

Tanya: Wow!

Eswar: Yeah, these are people who moved. It was a very exciting opportunity. I think everyone believed and to this day that this was some magical thing that had happened to us, and so we should just keep our mouth shut and do whatever needed to be done to get over the finish line.

Tanya: That’s amazing, and so you moved 40 families out. Was everybody of the 120 employees that you had at the time invited to move?

Eswar: There was a New York sales team. Our ad sales needs to be in Madison Avenue, New York City, so we didn’t press hard on that.

Tanya: Great, so the other thing that I wanted to know, you shifted between CTO and co-founder and CEO. That’s a shift in mindset. How did you approach that shift in mindset, and what were some specific experiences that you struggled with and learned from in your leadership approach?

Eswar: CTO, it turns out that you can provide a lot of cultural guidance without having the target on you. You can be the cultural visionary. It’s the co-founder in you is like – so Andy and I or Jeff Glass and I in those cases. When you’re CEO, you both are responsible for the culture as well as being the symbol of the company externally. There’s no break. You don’t get a break. As CTO, sometimes employees who are having trouble on the business side would come over and talk to me or the engineers would come and talk to me, and I could be the good guy. In some ways, it’s like you have to be both the good cop and the bad cop when you’re CEO. When you’re CTO, you can be the good cop and push it on to sales or CEO for all the unsavory things or the unpleasant thing that needs to be done to make a business grow fast, if that makes sense.

Tanya: It does. What was an example that you really struggled with that you realized that you had a lot of growing to do in your leadership approach?

Eswar: I’d say when we started to do this company called Tasteful, which was a healthy eating app. We brought on a bunch of folks who were from the healthy nutrition eating. Not tech people by any means. Folks you could consider almost as junior influencers in the social media world on our team. It is so important for them on a daily basis to feel like they’re connected to a good mission, and you have to spend a considerable amount of your time as a leader making sure that happens. I really admire leaders of consumer companies who can run the business by day and also spend time constantly reinforcing the values of the company and the mission of the company, and so that’s one area that I felt that I had to learn on the job and probably could do a lot more if I wanted to step back into that role.

Tanya: What were some of the ways that you enforced the values and the mission and the purpose of the organization in the everyday life?

Eswar: My natural way is to think that if I embody it in every conversation and how we talk to partners, etc., that things will take care of themselves. I found that I needed to be more overt in pulling together a mission statement, an exclusive mission statement, getting people to buy into it. Also, the hardest part was when having disagreements, when disagreements take place, using our mission and vision as a vehicle to inform how to adjudicate these disagreements to be – it always harkened back to this is what we’re all about. Therefore, we’re going to do X. Especially since I had some folks that had worked with me before, they knew me as the prior CTO type person, and then you have these new folks who wanted more of a visionary mission driven leader. I had to not just bridge different points of view but also my own transition from one role to another, but then stand true to what we are all agreeing we were all about.

Tanya: What was your process in crafting that mission and that culture that you wanted to really lead from?

Eswar: We brought in a consultant who spent some time with us as a leadership team to do it. Yes, I went off and did that. We wrote it down. We disseminated it. We got people to participate. Everyone seemed to be onboard, but I wonder if I could’ve been more decisive. Is there something else I could’ve done to take it up a notch beyond having it be a shared document?

Tanya: It’s interesting. People hire my company, my consulting company to do this, exactly this, and we work with huge companies. One of the things that we highly encourage our clients to do and something that I practiced in my own business, so built a business and exited it last year, is create a charter and what we stand for, who we are with our customers and with ourselves and pretty much every stakeholder. Be who we want to be being. We used that at the beginning of every all hands on meeting every week and read it together. It somehow brought us back to that moment, and not only that, we gave our employees an opportunity to acknowledge somebody on the team for whatever had happened the previous week that embodied what we strive for as a culture. People really felt empowered with that.

Eswar: Yeah, something like that. I think there was – the battle is won, as you know, in the trenches, in those moments, those decision moments. It’s not in the piece of paper or everyone’s standing around on Friday afternoon and toasting each other. It’s when you have to make those decisions. Yeah, so this is my continual self-evaluation process. What could I have done during those moments? I wonder sometimes if I was too interested in getting a consensus opinion versus just being myself and trusting that I was going to do the right thing.

Tanya: What’s the answer to that, if you have one?

Eswar: I believe I did too much consensus.

Tanya: That’s a common misconception that I see in leaders where, yes, getting buy-in from the team and having everybody aligned and rowing in one direction is so critical to the output, the performance, but at the same time, if you concede too much on the original vision, production or performance is diminished.

Eswar: Vision or timing, right. Like listen, guys. We should just give ourselves three months to get this done. Let’s just bang it out, and we have plenty of runway. These are the kinds of conversations that I know that I had in the back of my mind, but I was holding back because I wanted it to be the team’s process to do it. To this day, I don’t know if they were looking to me to just do it. We get along fine, so it’s all been reasonably good after that. It’s a thing that I ask myself about.

Tanya: I mean, that’s a really great inquiry. I mean, I’m you’re going to – I’m sure you already have plans for what’s next, but in your next venture, what would you do differently?

Eswar: If I were to do another venture, I’d try not to – I’d try to have it generate revenue by itself. I think that’s another very good way to build culture. I think the venture capital oriented approach which I have been the fortunate beneficiary of gives you capital, gives you air cover, gives you time to go off and think about building a team and mission and vision and all that, which is good, but there’s an alternate path. Maybe it’s the truer path, which is to see if you can build it strictly on the backs of people who are willing to pay for the stuff, and that may have a much cleaner forcing function as to who we are and what we’re all about than – it’s not a theory anymore. You have to decide who you’re bringing in and what they’re going to work on and what you’re all about, strictly driven by demand.

Tanya: Yes, it requires another level of discipline that, when you have plenty of capital funding the business, you can be a little bit lax on.

Eswar: Yeah, so what happened was we pivoted out of Tasteful and switched to BotCentral, and the money was running out. We ran in scarcity mode for a long time, and believe it or not, decisions were much simpler.

Tanya: Really?

Eswar: It was a small team, six of us. I mean, there was an existential threat, but it was not existential stress. It’s interesting. There’s no stress when you know what the – you can login and look at the bank account. You got to get off your butt and go close deals.

Tanya: Yeah, there’s a runway, and if you make it at the end of the runway, you’re going to fall on your face, yeah.

Eswar: Yeah, what are you stressed about? You just have to get out there. It’s not much to – that’s why if, yeah, there is another venture, it would be probably to try this other model.

Tanya: That’s very interesting. Being able to fund your business with nothing else but the pure sales that are coming into it is something to be – is very powerful. Coming from the venture capital space as well is not something that is done very much.

Eswar: Yes, so I admire two kinds of leaders a lot, those who can lead, who can – so Satya Nadella at Microsoft shifting their culture to a learning culture, that’s hugely admirable to me and then leaders who can build their company strictly from customer demand and revenues.

Tanya: Yes, so who in your life was by far the best mentor and leader, and what about their approach with you really resonated?

Eswar: A couple people for different aspects of personality, I guess. My college professor, who turned out to be my boss, a gentleman named Kwabena Akufo was actually a pastor at this point. He did a startup, sold it, and then has become the head of the Ghanaian church in the Boston area.

Tanya: What a change.

Eswar: Pretty cool guy.

Tanya: Yeah.

Eswar: Yeah, pretty cool guy. As a professor, he would always tell me the customer is always right when I would go and complain to him about a grade or whatever. Then I went to work for him as a summer student, and not surprisingly, he was the same person. I learned a lot about how to make sure you always have the distance, almost like a professional distance between the customer. You are delivering to a customer, and you are not the customer. Their expectations are the only thing that matters. You have to live up to their expectations. If they’re unhappy, you got to go deal with it, and there is no complaining about it. There is no one to blame except yourself, so that was a good mindset.

Years later, my CEO from m-Qube, Jeff Glass, who really taught me how to go raise money and close deals, he was the one who taught me it’s all trash until you see the cash so this idea that you have these great meetings, and then you’ll never hear from people again. You have to be on during the meeting, but when you walk out, don’t expect anything. You have to be properly dispassionate about the – given everything you have, try and get the best outcome possible, but it’s possible that these people will never call back for whatever reason. I think Jeff has been a good mentor for how to think about the fundraising process, how to go get – how to get deals done. Then my other partner at Quattro, Andy Miller, who was one of those people who could look at – who still to this day could look at any spreadsheet and tell you what this problem is, even when the numbers look good. He’s always thinking about the model.

What do we think we’re trying to do here? What are the numbers telling us about what we’re trying to do? There could be a lot of false positives, and so Andy is very good at that. It’s like these are aspects of my personality that I didn’t have necessarily to start with. You work with people long enough, and then you acquire some of those traits.

Tanya: It sounds like you had the unbelievable fortune of working with people that were able to teach you a great deal.

Eswar: Yes, anything meaningful is much bigger than, obviously, each one of us can do and so to the extent that you can really listen to everyone’s point of view but also just absorb what’s this – their strengths and to the extent that you can incorporate some of them into how you go about your day-to-day life. That’s very valuable.

Tanya: This is something that I always talk about with executives, transparency, and everybody falls differently depending on their experience and their company culture. What was your leadership style on being transparent with your employees?

Eswar: I’m the biggest blabbermouth in the world. I will talk to customers, partners, employees completely openly to the extent that I’ve been told to not show up. Don’t do that thing you do, but I just love what I do, right? It’s enthusiasm. I love telling the story, so yeah, if people can’t come along for the ride, then sorry. Yes, of course, there’s Apple secrecy. Yes, Apple taught me how to not bring up stuff that is secret. I’ve completely gone to that school for five years.

Outside of that, this is my own company. It’s a startup or whatever. I try to be as open as possible and teach to the extent that I can not just tell people what’s going on but try and explain the context for what’s going on.

Tanya: You would share your runway and all of the numbers and full transparency? Where did you draw the line?

Eswar: I don’t want to freak people out with precise bank account, but I can tell them how many months we had left given our current runway, etc. People have families and houses and all that. My job is to go make sure that they continue to have houses and all that. That is my job. Revealing that to them, all that does is freak them out, and that’s not their job. It’s my job. What I can is, hey, listen. This is important. We have this much time to go. We got this deal. We got to bring this deal in because it’ll buy us another couple of months, that kind of stuff.

Tanya: What were some of the things that you did when, let’s say, your companies weren’t doing so well that you used to boost morale or really infuse the company culture with a little energy?

Eswar: The energy, I think what I find is involving anyone in the company with customers is a great dose of energy. I think it’s a privilege for any company to have customers, especially if it’s a global customer base. I always tell people we’re a shitty little startup, and no one should care about us until they should start caring about us. I find the right group of anyone in the team reacts with the utmost rigor, energy when you can connect them with a customer use case, someone, a specific – an opportunity or whatever it might be. That’s always been my MO is to bring the team in and talk about what’s going on with different customers. Almost inevitably, I find that people are back at it and really don’t need that much rah, rah beyond that.

Tanya: I love what you said about assume that nobody gives a shit about your company and about you until they do. A lot of people that I know begin with the premise that they’re important, and then they go out in the world. Then they hit the market, and the market doesn’t care. It’s like a cold bucket of water right in the face and a major wakeup call. It’s interesting. It switches the context upon which, really, you go out there, and you seek product-market fit.

Eswar: Yes, and especially in the Valley. I mean, the other thing I say when I go to a café with my team is we’re talking about X. There’s five other tables where they’re talking about X, and they’re six months ahead of us. We’re already in sixth place.

Tanya: Yeah, that’s awesome. Yeah, run! Go make it happen. Yeah, that’s amazing. What are some of – if you take a look at some of the most important lessons that your parents gave you, what would those be?

Eswar: They taught me to be a citizen of the world. I am insatiably curious about everyone’s culture. If I could, I would flip this around and ask you all about you from exactly the way you did about me, and then I would go read up about all the places you said you were from. That’s one thing. Then the second is I still almost sometimes to an extent – I don’t think of myself as a pure engineer. You know when Steve Jobs said we stand at the intersection of technology and the liberal arts? I said, oh, shit, he exactly described it. That is who I think I am, and I think the liberal arts came from there. It’s that world view, liberal arts.

Then we grow up in a – we weren’t wealthy. I mean, they’re English teachers. As an open door, at home, we maintain to this day an open door policy of anyone is welcome, kids, dogs, whatever it might be. That atmosphere is what I picked up from them and, hopefully, will carry on to the next generation as well.

Tanya: Probably your love for reading came from them.

Eswar: Yes, absolutely.

Tanya: Which is a huge source of your learning and your mindset.

Eswar: Yes, it’s my constant sustenance through really pressing terms.

Tanya: What was one thing that you learned when you were working with Steve Jobs?

Eswar: I am actually pretty good at fashion as it turns out.

Tanya: Fashion?

Eswar: Fashion, you ask my wife. You ask my nieces. You ask my daughter. They’ll tell you it’s weird, but the guy is pretty good.

Tanya: Unexpected, very unexpected.

Eswar: Yes, I’m horrible. What I learned was to be brutal about, no, it makes you look like an X. He had this immediate visceral reaction to everything. For some strange reason, when it comes to something visual like fashion, I am – it’s something I picked up probably from being shredded by him a few times.

Tanya: He was actually commenting on the way you were dressing?

Eswar: Not dressing but the font you used in a presentation, everything, colors, fonts, pixel perfection, everything, and we were doing advertising. Obviously, Pixar was an ad company, so he actually knew quite a bit about advertising as it turns out, as we learned. There was a lot of cultural, visual stuff that he was constantly processing when looking at our work. He’d become trained – it’s like watching an art critic at work, and after a while, especially since he’s critiquing your art, you learn to look at it before you walk in. For example, iTunes Radio, the UI, I got to design it. Apple let me do that, and I survived the Apple human interface team’s review because I had gone through – I knew how to think about the stuff and how to throw out 99% of it and keep what’s left, very super simple. It’s a skill. Yeah, you’re asking, unexpected skill for a backhand Java developer type person. That’s what it is.

Tanya: Wow! Where do you think – in seeing Steve Jobs lead, where do you think he failed in something that you took note of and influenced your way of thinking about leadership?

Eswar: He was 100% convinced that every brand would pay a million dollars for the ads. That was the opening – actually, it was $10 million when it started off, and so he was not reading the market. The advertising market through Google and Facebook has become a lot more savvy about getting a return on investment. We came in at the beginning of that wave, and we mistimed our entry. For someone so aware and connected as him, I’m surprised. I mean, Eric Schmidt was on his board, etc., etc. This is something that he should have known was happening.

We were, as a scrappy startup, of course, all about an ROI. Then we go to Apple, and Apple’s like, no, screw it. They’ll pay anything. Trust us. We’re like, okay, it’s Steve Jobs, and he knows [44:15]. He had Pepsi and so Robert Iger at Disney. Of course, they’ll pay if he says they should pay, and they did pay because they’re not fools. They want to see return on investment.

Part of it is no matter how much of a market position you occupy, you cannot believe – it goes back to the shitty little startup story. Every new venture is in some ways that shitty little startup, right? You can’t assume you’re just going to walk in and win. You have to start. The fundamentals are the fundamentals, especially these days when it’s so competitive.

Tanya: Yes, and really, not to get egotistic and let that drive the show.

Eswar: Yeah, I think it felt – there was an element of ego driving it that I found myself having to defend with some ad buyers, and it was uncomfortable. It was a good lesson, which is you can’t just walk in and throw your weight around.

Tanya: It’s a powerful lesson to learn, especially when you’re at one of the largest companies in the world, most successful companies in the world.

Eswar: Yeah, we didn’t know. It’s working, so let’s follow the model.

Tanya: Yeah, that’s great. Then if you could rewind ten years and give yourself, specifically related to you one piece of advice, what would that be?

Eswar: Ten years, one piece of advice.

Tanya: Doing the math.

Eswar: Yeah, I’m doing the math out of my head. I would not tell myself – so ten years ago is when – around now is when we – I had my first Apple meeting. I would not try to go public with Quattro Wireless. I think the Apple deal was a good one. I think the advice I would give myself is I was engaged when Quattro was acquired by Apple, totally engaged in the game, but to a certain extent, I’d taken my eye off the ball in terms of are we building a super successful business from the ground up? I think you can never be – just because a big event happens to you, etc., etc., you can never take your eye off that ball, ever.

Tanya: Get comfortable.

Eswar: Never get comfortable, yeah. Only the Paranoid Survive is Andy Grove’s book title. It’s worth rereading that.

Tanya: You’re the second person that talks to me about that book in the last week.

Eswar: Great, he’s another amazing individual.

Tanya: Yeah, no, that’s great. Can you tell us what you’re working on now?

Eswar: Right now at LivePerson I am doing corporate development in M&A. LivePerson is an interesting position of conversational AI through Alexa messaging, etc. All these people around the world using WhatsApp, it’s become an interesting way for people to communicate through businesses, and the AI is good enough that it could pick up on intent, loosely worded intent. We actually are very strong in one use case for conversational AI, which is customer service. We are expanding to sales and marketing and a bunch of other use cases and also doing verticals like banking and health insurance and so forth. My job is to go seek partners, content, assets that we can bring to bear to expand our market presence, our portfolio. I’m the fox in the chicken coop I guess you could say, having been on the other side.

Tanya: You’re hunting.

Eswar: Yeah, I’m hunting now.

Tanya: You’re hunting, well, happy hunting. That sounds exciting.

Eswar: It’s fascinating. Now I’m starting to look at assets as companies. There’s just an asset, an entity. It’s a very different – and I’m working with the people who used to be checking me out. The bankers used to be checking us out, and so yeah, after a little while of doing this, I’ll be – I have no idea where I’ll end up on the spectrum of entrepreneur or acquirer.

Tanya: It’s interesting because you probably know all the hot buttons to press and questions to ask as an operator.

Eswar: The problem is I’ll never be a VC because I fall in love with every entrepreneur. That’s who I am. I’m an entrepreneur. If I see a fellow entrepreneur, I fall in love, and so I have to distance myself. It’s almost like a requirement. First you have to fall in love, and then you distance yourself. Then you can analyze it.

Tanya: You break up, get some distance, and then think about maybe getting back together.

Eswar: Yeah, something like that, yes, and it’s probably no fun on the other side. What? Is this person crazy or something, but how else? I have to get very enamored with the problem, the approach, the team, etc. because that’s how I operate from the other side. It’s very personal.

Tanya: That’s amazing. Just for the people listening, how can they get in touch with you if they want to get in touch with you?

Eswar: You could always find me on LinkedIn or on Twitter, @eswarpr.

Tanya: Awesome, well, thank you so much for being on the Unmessable show. Your career and your entrepreneurial journey is so unbelievably inspiring and just really grateful that you shared some of your key learnings about leadership with us today.

Eswar: Thank you, Tanya. It was a great conversation.

Tanya: Unmessable is recorded in the heart of New York City, and a special thanks to all the team involved in producing the show. Visit tanyaprive.com/unmessable to find a transcript of this episode, and be sure to subscribe to our newsletter.