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First-time founder and Harvard grad Carlos Reines, who was nominated by the World Economic Forum as Young Global Leader opens up about his tragic childhood accident and how that shaped his life-work today through RubiconMD — an eConsult platform that connects clinicians to top specialists. Now serving over 5,000 primary care physicians in 37 States, RubiconMD has saved over 2.5 Million days of patients waiting for specialist consults, which is almost 7,000 years.

Carlos talks about his struggles early-on when he launched RubiconMD and how, after many iterations, he designed a dialed-in hiring process to assemble a top tier team that not only has individuals with world-caliber credentials but that act as a team and feel connected to the mission of the company– democratizing and improving access to quality healthcare.

In this episode you will learn about:

• • • Healthcare innovation
    • Leadership
    • Leadership Mistakes
    • Building a startup
    • Managing and scaling a team
    • Raising capital
    • Company Culture
    • Effective Feedback

 

About Carlos Reines:

Carlos is one of the cofounders at RubiconMD. The company was founded in 2013 with a driving vision of democratizing medical expertise so that providers can offer every patient the care they deserve.

Originally from Spain, he’s passionate about leveraging technology to drive change in healthcare.

Prior to RubiconMD, Carlos led a division at Telefonica, one of the largest telecom companies in the world. He began his career at Siemens Healthcare.

He earned Masters’ in both Bioengineering and Telecom Management in Madrid, and an MBA from Harvard.

Connect with Carlos Reines:

Linkedin
Twitter
Website

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Full Transcription:

Carlos:  I think I always had an easy one because my dad’s name is Carlos as well. I don’t think they had to break that too much.

Tanya:  That’s great, so they followed the wonderful Spanish tradition on naming. 

Carlos:  Yeah, absolutely.

Tanya:  That’s Carlos Reines, Harvard grad and entrepreneur who raised $20 million for his startup RubiconMD, an eConsult platform that connects clinicians to top specialists. Now serving over 5,000 primary care physicians in 37 states in the US, RubiconMD has saved over 2.5 million days of patients waiting for specialist consults, which turns out to be almost 7,000 years.

Carlos:  I grew up in Madrid. Actually, all my family is in Madrid. I was born and raised there, lived in the center of the city for the first few years, and then we went to the suburbs when I was about 5 or 6. I’ve really been in Madrid most of my life. When I was 22 is the first time that I went to study abroad. Through different work experiences and educational experiences, I’ve ended up spending time in the Netherlands, in Germany, and obviously, a lot of time in the US.

Tanya:  If you were to describe yourself as a kid, how would you describe yourself?

Carlos:  I was the only child, only nephew, only me, no cousins, for ten years. My mother is the oldest of six. On my dad’s side, his uncle never had children, so for about ten years, I was there by myself. I was getting a lot of love from the entire family.

Tanya:  I can imagine. 

Carlos:  At the same time, I was dying to get some folks around. I wanted to have cousins. I wanted to have siblings. In Spain, there is a big tradition in Christmas that the Three Magic Kings will bring you games and toys, and when I was a kid and I would write my letter, I would never ask for any games or toys. I just wanted to have a brother or a sister. I wanted to have that for a long time. It never happened, so I grew up as an only child. At some point, my parents had friends that lived outside of Madrid, and their son moved to Madrid for college. He was about five years older than I am, and he went to live with us. For three years, all of us had – I had an older brother, and it was an awesome experience.

Tanya:  I can imagine. After all that time, it must’ve felt great to have company. 

Carlos:  Absolutely.

Tanya:  Something important happened when you were a child.

Carlos:  When I was 8, I was playing on the street with other kids. We were playing with slingshots. It was just kids who are the street, and I was hiding behind the car. Unfortunately, somebody was incredibly accurate, and they hit me in the eye. That was actually a pretty severe accident that triggered three very complex surgeries. Probably over the span of two years, I lived half of the time either admitted to the hospital or sitting in an ophthalmologist office. I couldn’t go out. I couldn’t play with other kids. I had to be incredibly diligent with my eye drops. 

That was actually very tough. As an 8-year-old, all you want to do is to be outside and then play and not have to worry about anything, and I had to go through a lot of complications. Eventually, I had the surgery where the ophthalmologist said the best thing we can do is stabilize the eye, and this is something that you should reevaluate whether you can have more surgeries or there is any path forward maybe in 15 or 20 years as an adult. That was between age 8 and age 10, roughly. 

Tanya:  Wow! That’s brutal. How did that influence who you are today and shape your outlook on life?

Carlos:  I think it influenced me in many ways. I wish I didn’t have that accident, but at the same time, I’m very grateful for all the things that I’ve learned out of that experience. I think mostly on – probably on three different levels. The first is what I do now was definitely influenced by what happened to me, right? I decided to become a healthcare technology entrepreneur, and I started RubiconMD. This is, obviously, years later. This is only a few years ago, but out of that experience, I grew the motivation to want to fix healthcare because I had experienced myself just of not having access to the right care at the right time. I knew that somebody had to fix it. Eventually, that’s where I gained the strength to go pursue this mission that I’m working on now, so one was in shaping what I wanted to do.

I think, two, I’m also really grateful for a lot of the strong relationships that I’ve been able to develop, very close with really everyone in my family, so at the time of the accident, I felt incredibly supported. There wasn’t a day where I was at the hospital and I didn’t have either my parents, my uncle, my aunt, someone sitting with me. I think that is reflected in now it’s 20 years later or 20 or 30 years later; I have incredibly strong relationships with them, with everyone in my family and also friendships. I remember when this happened, and I had to go back to school. I couldn’t go out and play outside. I had to stay in the classroom, and I had to use my drops. One of my friends at the time would stay with me every single break. Instead of going out to play soccer or whatnot, stayed indoors playing with me. He was the one putting the drops in my eyes. Again, almost 30 years later, he’s one of my best friends now. I think of a lot of those relationships really solidified, and those are really priceless.

Tanya:  How did you handle the person, the child that caused the accident?

Carlos:  I didn’t, really. This happened when I was 8. At 8 years old, you barely understand what’s going on, what’s happening. I don’t think I ever saw that kid ever again or spoke to him again. Not because I didn’t want to. It’s just the following two years I was, basically, at hospitals and doctors’ offices, and after that, we never had an opportunity to reconnect. I think one thing that’s interesting is that you really don’t understand what’s going on, and I think, for me, it was probably, I don’t know, maybe five years later or so when I was growing up, when I was going through adolescence that I started to realize that I had gone through a pretty serious accident and understand a little bit of the implications. It was probably more difficult in those years than it was originally. As a kid, I was just cruising through life.

Tanya:  Yeah, I can imagine. Do you feel affected in any way by what happened to you today, or what is going on with your eye?

Carlos:  No, not really. The good news is that we are born with two eyes, so despite having pretty limited or not really any useful vision in that left eye, I can do everything normally. It didn’t stop me from being able to drive, being able to play sports, or have a perfectly normal life. I don’t think it’s put any restrictions into anything that I do, but I do think that I’ve developed a lot of capabilities that I probably wouldn’t have developed if I didn’t go through this. I think a lot of that is pretty well reflected and really helpful as I’m going through the entrepreneurship journey, which is a brutal experience. A lot of the things that I learned at the time, being able to work through challenges, jump through hoops, or remove any hurdles that are put in your way, I think the perseverance that you need as an entrepreneur, I think I found a lot of that in having to figure out life going through a lot of the challenges as a kid.

Tanya:  Yeah, I mean, that’s unquestionable that your accident was the training ground for your career. Not only as an entrepreneur, but in healthcare, you were firsthand affected by the problems that you’re actually trying to solve today. How did you get into your entrepreneurial journey?

Carlos:  It really started in 2012. Up until that time or before that, I was in Madrid. I was working for Telefonica, which is one of the largest telecos in the world, and I actually had a really cool job. I was part of this corporate unit. It was called the Global Chief Technology Office, and we would do technology projects across all of 25 countries where the company operates. We would be standardized in best practices, technology guidelines, choosing solutions; that everybody rolls out the same technology and be more effective. I got to interact with, really, all the areas of the business.

Then a friend convinced me to apply to business school and to apply to schools in the US, and in 2012, I found myself packing and moving to Boston to start business school at Harvard. Going in, I knew I had – so before that, I had worked for Siemens and Telefonica, two massive companies. I thought this is the perfect transition to try something else, to go early stage. Why not, to start something myself? I really spent my first year in business school going to a lot of the entrepreneurship events in Cambridge. There are startup weekends and hackathons virtually every week.

By going to a lot of those, eventually, in March of 2013, I met my co-founder, Gil, at a Hacking Medicine event at MIT where he was pitching the idea. He was also inspired by personal experience where his grandmother had a brain tumor. She was from Barbados, and she had to travel to Boston for surgery and then for the postop care. He was also frustrated with the limitations of accessing care, and the two of us worked together through that weekend. We found that this is an idea that made a lot of sense. We were excited about that we could execute, and on top of that, we got along really well. We had very complimentary styles, and we decided to start a company together.

Tanya:  Wow! That’s RubiconMD.

Carlos:  That’s RubiconMD, yeah. Basically, what we do – so the two toughest problems in healthcare in the US – probably number one is, obviously, the fact healthcare is an incredibly expensive sector with almost 20% of the GDP spent in healthcare. That’s twice as much as any other advanced country of their healthcare expenditure relative to the GDP with it actually achieving better population health metrics, and then on top of that, you have about half of the country who really struggle with access to care. We quantified that more than 50% of the population in the US have real challenges accessing a specialist, and that’s real unfortunate. We decided to tackle a dual problem by letting primary care clinicians submit electronic consults to specialists, so whenever a PCP has a case that’s a bit more complex, what they do is they access our platform. They type up a brief description of other patients. They ask a question, and they send it to a specialty. We have a top specialist review and get back to them with their impressions and recommendations in a matter of hours, and that allows the primary care clinician to make a much more informed decision and diagnosis, treatment plan, and next steps for the patient.

Tanya:  I mean, I think that, first of all, what you’re doing at RubiconMD is pretty amazing. I can’t tell you how many times I went to a pediatrician or a general practitioner and said what’s going on here? They send me to God knows who, and it takes time to get the appointment. You’re looking at months before you even get to loop back with the primary care physician. It’s frustrating, so that’s amazing. How many clinicians and primary care physicians do you serve?

Carlos:  Oh, we must have probably about 5,000 clinicians across the country. We are present in 37 states working really with all flavors of primary care. One thing that’s fascinating is that you just share your experience. It was frustrating that you probably wasted time and money and things that were not really necessary, but one thing is that you could afford it. Even if it was painful, you had access to care. About 60% of what we do is safety-net populations, uninsured, undocumented, Medicaid patients that are looking at wait times measured probably in months if not years. One of the things that’s really fascinating of what we do is that we are bridging that access gap for the most underinsured populations who are now through their primary care clinician getting access to the expertise of some of the best specialists in the country, and that’s where we are executing on our mission of democratizing access to medical expertise.

Tanya:  I love it. That’s amazing. How big is your team now? 

Carlos:  We are about 45 or 50 people, most of us headquartered in New York City. Then we have West Coast office in San Francisco, and we also have a few remote engineers based in Spain.

Tanya:  Amazing, all the key locations. I just want to shift gears a little bit. In terms of what it took to actually begin the company – well, first, what do you do at Rubicon? What’s your job? 

Carlos:  As the president and co-founder, I oversee the delivery side of things, so I work very closely with the product team helping inform a lot of the road map and future decisions with the input that I get from the market. I work closely with the operations team; help them build for scale. I work closely with the implementation customer success teams, and they are supported by what we called user engagement. It’s, basically, we’ve taken the approach in a loop – all the learnings that traditional tech companies have in their growth hacking teams and adapted it to bring it to healthcare so that we could do rapid experimentation and learning around the things that work for clinician engagement with technology. Those are the teams that I oversee. I think, as a founder, I can’t get out of being on the road a lot of the time, so probably a good portion of my time is still dedicated to business development and checking in with our partners.

Tanya:  Okay, yes, and aside your actual job, you have a bazillion other jobs. Your job is to just make the company successful, whatever it takes. When you start a company in the early days, it’s brutal. It takes a lot. What were the early days of RubiconMD like for you?

Carlos:  Yeah, so the early days were actually really hard and, at the same time, really fun starting the business. I was my first year of business school when I met my co-founder March of 2013 over that weekend at a Hacking Medicine event at MIT, and then we followed up, did a second hackathon about a month later. It was called 3 Day Startup, and we won best pitch. Then we said, well, this actually has a lot of potential. I think there’s an opportunity to build a business here, so shortly after that, we incorporated the company. That summer, I moved to New York, and that’s when we worked on developing the first prototype. We found one clinician who wanted to give it a shot, someone who had trained with Gil’s brother or had trained Gil’s brother in Connecticut, and we recruited maybe three or four specialist. That’s all we had at the time, one PCP, and I think one cardiologist, one dermatologist, one orthopedic surgeon. Not more than that. 

We built a prototype that I put together, a very simple MVP. It was just the front end. What the person would do is they would access the “platform,” platform in quotes. They would submit a consult. I would get that, and I would have to do everything manually. I would have to run those cases manually to the specialist. When I got their responses back, I had to go back and tweet the front end of the platform, so it was incredibly manual. 

We did that for probably about 200 consults, and then we regroup with this primary care physician in Connecticut. He said something that was fascinating. He said, “Well, first of all, this is the most doctor-to-doctor communication I’ve had in ten years, and on top of that, I’m not only learning things, but I’m also able to improve care for my patients who would have otherwise not had the ability to go see a specialist and maybe would’ve had to end up in the ED. I’m actually not only doing better care, but I’m also generating big cost savings for the system.” That was for us the biggest validation. We had a clinician who was getting a lot of value clinically, and his patients were benefiting a ton. That’s when we decided to raise a little bit of capital and start building a team and to actually build a legit platform.

Tanya:  What was one of the toughest moments professionally you had to deal with as a leader?

Carlos:  I think the first year was brutal for me because I was still in business school. We applied to an incubator. They said we’ll take you guys if you drop out of school. I was already going back. I was already starting projects with classmates. I was really using every class to apply to the business. We decided that it made more sense for me to finish business school, but that also meant that I was doing two things at the same time, right? I was starting a business from the beginning, and I was going through my second year of business school, and that was brutal.

I remember days where I would go to class in the morning, and then I had to get in a car, drive to New York. We were meeting with investors or a potential customer, or we were talking about the product and then drive back. Many days I find myself – it was midnight. I was dead tired, and I had to do a lot of homework and reading for the next day so eventually managed to go through both. I still got a lot of value out of school. At the same time, we continued to grow the business, but it was brutal. I remember the last days where I was like I can’t take one more class, one more case, or I’m going to break.

Tanya:  I can’t even imagine. That’s so crazy. At what point did you start to raise capital and really see your team grow?

Carlos:  The first capital we raised was when we – before we launched that really early pilot, we had some basic cost that we had to face before we could start operating. Things like liability insurance and funds to pay the specialists and just the basic things. The first time was actually pretty interesting. We had met this person through a friend of ours, and he was the former CEO of a very large health plan. We connected with him, and we was initially just an advisor. He started to give us his take on how this could fit into healthcare. What are the things that we should have in place? Eventually became a little bit of a more formal advice. We were checking in with him regularly.

We asked him, what would be your advice? We’re at a point where we need to raise some capital. Do you recommend us to start by going to a fund, going to a few angels? What do you think? He offered himself. He said, “Well, if I was interested, would you guys take an investment from me?” It was very natural. Of course we would, right? He had been incredibly helpful already.

That’s how we found our first investor. It was very natural, and then a lot of angels piled up on top of it. He obviously brought the credibility.

Tanya:  It was a strong signal.

Carlos:  Exactly, then we had other investors who were maybe stronger in tech but having someone who’s such a healthcare expert, a physician, a manager, CEO to back our model, it was a strong signal. Probably the first half a million dollars we had raised was through super angels. Then we started working with some of these early stage health IT funds that invested. That was our seed round. Which from the first check ‘til we closed it, we probably kept it open for about a year. We were just raising capital as we were getting more traction, and eventually, it was about 1.3 million that we raised with a combination of angel funds and one strategic investor that joined the round at the end.

Tanya:  At what point did you start thinking about RubiconMD’s culture?

Carlos:  That probably happened after we did our Series A. Our Series A was about a year and a half after we had closed our seed round, and that was the first time that we went through multiple hires. Right up until that time, it had been the three founders at the beginning and super-early employees that were part of the founding team so a very small team. When we started to bring more people onboard, it’s when we realized that the culture was going to be incredibly important. We didn’t get it right the first time. I think through the first iterations of hires, we brought people who were really good but maybe weren’t the best cultural fit for what we wanted to – where we wanted evolve. I think, as we were growing the team and through some of these successes or failures in growing the team, we started to realize the importance that having a strong culture would have for the company. Where we are today, I think culture is incredibly central for us. We dedicate a lot of time, resources, and attention to it, and I think it’s one of the key assets of RubiconMD.

Tanya:  Awesome, and what is RubiconMD’s culture?

Carlos:  We define our value system human, agile, innovative, and collaborative. I think that’s a good characterization of what you would see across the board in the team. First of all, I think I told you my personal story, and I shared a little bit about my co-founder’s personal story for why we do this. When I look inside the RubiconMD team, almost everyone or everyone has a reason why they’re doing this, right? They could be doing something else that’s maybe more comfortable, or it has more perks, but they’re all here because they are incredibly mission driven. They want to change the world through their skillset. I think that’s number one characteristic, very, very strong mission in the team. Number two, we’ve been able to attract really talented individuals that thrive really well in the craziness of the startup journey, right? You need folks that are the – that can function autonomously and that want to be pushed really hard and can solve really hard problems and collaborate really well with each other, so I’m very proud of the talent that we’ve been able to bring onboard. 

The third element of our culture is diversity. You would think that for a company that has to work really fast and that’s, basically, optimizing for having folks that are mission driven that you could expect that most of us would be the same or have the same backgrounds, and I think it’s quite the opposite. Some people refer to us as the UN of startups. We have so much variety in terms of countries of origin, backgrounds, races, gender. I think we’re about 60% female represented across the board, right? It’s not that we have just a very large marketing team with a lot of women in it. No, we have female representation across the entire company in leadership. Even at the board of the company we have female representation.

The beauty of this is that diversity has never been – we’ve never pushed for that. We’ve never even thought about or quotas or anything like that. It’s happened naturally. I think as we’ve been able to grow a more and more diverse culture, it also becomes a magnet for people who thrive in that environment, and that, in a way, becomes a self-fulfilling prophecy.

Tanya:  That’s amazing. I mean, the fact that it happened naturally and it wasn’t in response to what’s going on in the environment today in business, that’s amazing. What type of resources do you use to really keep yourself engaged and growing as a leader?

Carlos:  I put a lot of attention to it. There are several things that I do. Number one, inside the company, I think it’s incredibly important to encourage a culture of feedback, open, transparent, honest 360 feedback. We have that in place, but I particularly push really hard folks in the team to be very candid. That’s the only way I can learn about my limitations and work on getting better, so that’s from the inside.

Tanya:  How do they provide you feedback? Do you have a quarterly meeting or a survey that goes out? What’s the setup of that feedback loop?

Carlos:  We have a lot of things in place. This culture is so important. Our head of people in culture spent a lot of time working on it. Twice a year we do employee reviews. Those are reviews by their manager, but in between those cycles, we have peer review sessions so that we can get feedback from a personal level to the organization and from everybody. It is a time consuming activity. It takes a lot of resources, but I think it’s incredibly worth it.

Then we encourage feedback, and we enable multiple talents to provide it. There are folks that will be very comfortable providing direct feedback to a person and identifying themselves as the authors of that feedback, and there are folks who are more comfortable just giving in a more anonymous way. What we do is we have each manager collect feedback from different sources, and they package it up, and then they deliver it to an employee. Where somebody is comfortable and wants to provide more one-to-one direct feedback, they’re welcomed and encouraged to do that. If people prefer to provide it in a way that’s a bit more anonymous because they don’t want to potentially harm a relationship, that’s also fine. All we want to do is the people – make sure that people have enough content for them to understand what are the areas where they can keep improving, and also, what are the areas where they are doing really well and that other people appreciate?

Tanya:  Just curious, what was one of the pieces of feedback that you got that was impactful for you? 

Carlos:  I think, one of the pieces of feedback that I’ve received, it was very insightful is that there’s feedback on feedback, right? I spent a lot of time providing constructive feedback because I feel like I owe it to the employees. It’s my job to make sure that everyone here is getting better and better and learning new things every day. I have a very natural tendency to focus on the constructive feedback. Folks really appreciate to also learn what are the things that are working well? Not just to get the pat on the back but to be aware that, something they are doing, it’s actually very effective, and they need to keep doing it. That was a very important piece of feedback. That I should spend more time also on the positive feedback and reinforcing the things that are going well as much as I do on the constructive feedback, and what are the elements where folks need to work on to improve?

Tanya:  Really, encouraging not just for what needs to be improved but also what’s working, which makes sense. When things are working, you don’t put as much thought. They just work.

Carlos:  Right, and I think that’s a – that’s why I naturally go to how can we better? It’s that obsession with we keep growing, but I think it’s a very fair point to also recognize people when they do things well.

Tanya:  Yeah, absolutely. What was your favorite or your most influential leadership or management book that you read recently?

Carlos:  I’ve been reading a lot recently around hiring. Probably one of the most important and at the same time one of the most underrated functions at any company or qualities in many leaders is recruiting and talent management. I don’t understand why in many places HR remains a function that’s a little down or not properly respected. The most important asset for most of the companies and definitely for us is the human capital, the talent that we have onboard.

Tanya:  Without a question, yeah.

Carlos:  I’ve learned that a great employee who is mission driven, highly motivated, and whose performance is really high is incredibly valuable. I spent a lot of time reading about the topic either – in particular, two books that I found really helpful around improving the hiring processes and talent management. Those were Work Rules!. It’s a book by Laszlo Bock. He was the former head of people at Google. From that one, I took away – I guess one thing they did, it was fascinating, is that they mapped all hiring processes, and they understood the ratings that people had given. They map it out to how that correlates to the success of the hire in the job. After tens of thousands of hires, you start to see some interesting trends, so they have a pretty thoughtful framework for how to structure an interview. It’s very natural for us when we are interviewing someone to just go back to all right, this is the job description. I want to know what you did in the past, and then I’m going to make a decision on whether you’re a good fit for this job or not.

I think that’s short sided because that’s only one of the elements. I think in that book –we’ve tweaked it a bit, but our framework now is we look at a candidate. We want to understand what are their leadership styles? How would they fit with our culture? What’s their general cognitive ability? What’s their role-based knowledge for what they’ve done in the past, but also, what’s their role-based aptitude? What are the things that they’ve done in the past? Even if they weren’t exactly doing this job, how do they prepare them to do the work that we’re going to be asking them to do? We found that by having different categories and letting people focus on specific items of those we are being able to have a much more effective and less biased hiring process.

That was incredibly effective from that book, and then the other one that I also found very interesting is a book – I think it was called Who. It’s, again, a hiring method, and they take you through all the steps that you need to have in place before you go out and start searching for a candidate around properly defining the job and define what are the metrics for success?. Getting internal alignment in the team around what are the things that we’re going to be looking for as we start to bring candidates onboard? Really elevating the team’s ability to be better recruiters and better searchers of talent for the company.

Tanya:  That’s super interesting so trying to solve the hiring problem, which is a huge one and at the basis of building a team, really.

Carlos:  Absolutely.

Tanya:  Awesome, so last question, what is next for RubiconMD?

Carlos:  It’s been a little over 5 years since we started the business with about 5,000 clinicians using RubiconMD. When you look at the stats, they are very impressive. Primary care clinicians report that, when they use eConsults, 80% of the times they are able to significantly improve the patient’s care plan. Seventy percent of the times they are building capacity. They’re not just helping patients at one point in time. They’re learning things that they will use in future patient care, and they are avoiding more than half of the times unnecessary referrals, duplicate tests, unnecessary [36:20] cost. It’s been more than proven that this has a ton of impact on the quality of care delivered and the costs that are being taken away from the system and the patient experience. We’ve taken away more than two and a half million patient wait days. That’s time that would have stood in between the patient and the right care plan, particularly for the most underinsured population.

Tanya:  Carlos, let me just make sure I understand that, 2.5 million wait days you said?

Carlos:  Yeah, that’s correct.

Tanya:  In other words, 2.5 million days that patients avoided waiting to go see an expert and get the care that they needed.

Carlos:  Exactly.

Tanya:  Wow!

Carlos:  If they didn’t have eConsults, they would’ve had to wait all that time to get to the right care plan, if they ever were able to get to the right care plan, which in many places they can’t.

Tanya:  Wow! That’s almost a lifetime or more.

Carlos:  Yeah, the model is incredibly effective. It works really well. Five thousand clinicians is just scratching the surface. There are almost half a million primary care clinicians in the country, and this works really well. Healthcare is very fragmented, so incentives are not always aligned. As much as I would like to see all financial incentives be aligned towards improving outcomes, improving the patient experience, and reducing the cost of care, that’s not necessarily the case for a big portion of the system, but we’re working really hard to work through those challenges. We live in a world where five or ten years from now there shouldn’t be any primary care clinician in the country and why not eventually in the world who doesn’t use eConsults as part of their practice because these are incredibly beneficial for patient care.

Tanya:  Yeah, I mean, it makes so much sense. How do people get in touch with you?

Carlos:  Anyone who wants to get more info on RubiconMD can find us online at rubiconmd.com, and for anyone who wants to contact me directly and get anymore insights, carlos@rubiconmd.com is my email. Feel free to reach out, particularly if you are a mission driven individual who cares about improving access to care. I’d love to connect with you.

Tanya:  Amazing, Carlos, thank you so much for spending the time and sharing your amazing personal story and what you’re doing with RubiconMD.

Carlos:  Thanks so much for having me, Tanya. I really enjoyed it.

 

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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.

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Former school teacher, Julie Clark hit the jackpot when she created enriching entertainment videos for her kids, in her basement. It turned out, other babies loved it too. Within five years, what was a fun side project grew into a $23 Million dollar generating business which had only five employees, that Disney acquired for $25 Million. Within a few years of selling to Disney, the company was producing close to $300

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Dane Madsen grew up in a small farm town in Idaho, on the lower income side of the equation, but was trained to problem solve and fix things from a young age. His upbringing forced him to be nimble and creative in the solutions he brought forward and this core way of being was at the source of his ability to uncover a huge opportunity in the market when he built Yellowpages.com, which he later sold to what is known today as AT&T, for $100 Million. In this Unmessable episode, Dane shares his internal struggles as he built and sold his company, and more importantly what he learned from his fascinating journey.