Episode 32

L.O.V.E. to Lead

with Sean Lane

May 3, 2022

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Sean Lane
Chief Executive Officer, Olive

Sean is a lifelong technologist, having started his career in the U.S. intelligence community before going on to hold multiple leadership positions in the Department of Defense and the National Security Agency. Sean served five combat tours in Iraq and Afghanistan and was awarded the Defense Meritorious Service Medal and Bronze Star Medal for his service. After government service, Sean began his life as an entrepreneur and has founded several technology companies centered around big data, advanced analytics, entity resolution and most recently, artificial intelligence.

As the CEO who founded Olive, Sean has also raised over $900M in venture capital and is now a leading expert in applying Al to healthcare. Sean also serves as CEO of Circulo, a Medicaid insurance company of the future that provides tech-enabled world-class care to the nation’s most underserved.

Sean holds a bachelor’s degree from Miami University and an honorary doctorate of Public Service from the University of Rio Grande and has received the Ernst & Young Entrepreneur of the Year Award.


Time is our most precious resource in healthcare. And we are, right now, leaking 10 billion hours worth.



[00:00:28] Gary Bisbee, Ph.D.: Well, good afternoon, Sean. And welcome.

[00:00:31] Sean Lane: Good afternoon, Gary. Great to be here.

[00:00:33] Gary Bisbee, Ph.D.: Well, we’re pleased to have you at the microphone. This show is about pursuing leadership excellence and we’ll return to the leadership theme throughout our conversation. First, why don’t we get to know you a bit better, sean, what was life like growing up for you?

[00:00:50] Sean Lane: Ah, good question. So I grew up in a small rural town in Southeastern Ohio. And growing up, I always wanted to be a spy. So that was, like, the thing that drove me was, how do I become a spy? And I was also into computers, so I got a computer at an early age. It was like fifth grade. And I started to learn about coding. And then the internet came about and I was really just enamored by the internet. So I was kind of a spy who was also a nerd. And that was my upbringing.

[00:01:23] Gary Bisbee, Ph.D.: You We’ll return to the whole intelligence space, if not the nerd space, as we go, but so. did you think about leadership or at what did it occur to you that you were what I would take to be a natural leader?

[00:01:38] Sean Lane: So I studied leadership. My dad was a Colonel in the Army National Guard. He brought home lots of manuals when I was a kid and it kind of filled the bookcases of our basement. And I would read all those voraciously. Some of them were about Soviet weapon systems and different military strategies, but many of them were about leadership. So I read a lot of that, consumed those books at an early age and really was eager to learn more. And then pursued some leadership courses in college and really got my chance to be a leader in the military. And that’s where I had the first opportunity to really test out all those things I had learned, or at least the methodologies that I had read about.

[00:02:21] Gary Bisbee, Ph.D.: So your dad brought home books and I’m sure you discussed that. Do you think your leadership style at all emulated your father or came from your father?

[00:02:30] Sean Lane: Well, I think a lot of it came from the way the military had thought about leadership. It has since evolved quite a bit from that point. I’ve learned the military is a very unique environment and certain things work in the military that don’t work in the kind of civilian world. But many of the principles are the same. And most people get it wrong when they think about military leadership. They think it’s very command and control. It’s very, it lacks empathy and all those things. But I don’t think that’s true at all. Some of my greatest leaders in the military were those who were very empathetic, very thoughtful leaders, like the ones that you would experience outside of the military.

[00:03:10] Gary Bisbee, Ph.D.: So when you graduated from Miami University, you joined the US Air Force. Was that always your plan?

[00:03:18] Sean Lane: It was always my plan to be in the military as a way to get into intelligence. That was what I knew would be the path to get into the intelligence community. But I wanted to be in the Army, actually, when I was a kid. But unfortunately I’m colorblind. So I cannot be a Army intelligence officer. So I switched over, had my sight on the Air Force and being an intelligence officer there and was super fortunate to get a spot in intelligence. And it kind of paved the way from that point.

[00:03:48] Gary Bisbee, Ph.D.: Well, we appreciate your service. You served five combat tours in Iraq and Afghanistan, and won at least two metals, the Defense Meritorious Service Medal and the Bronze Star. So again, we thank you for your service.

[00:04:04] Sean Lane: You’re very welcome. Very welcome.

[00:04:06] Gary Bisbee, Ph.D.: What areas did you specialize in in terms of intelligence?

[00:04:10] Sean Lane: In the beginning, I did support for the war fighter on the ground, mostly the Army soldier. So as I mentioned, I always wanted to be an Army officer, but didn’t get that opportunity. But fortunately, my first duty assignment was with the Army. So I got to provide air intelligence basically to the Army. And I did that in Iraq, but I found that my real super power around intelligence was technical, so really understanding all the different sensors and different systems and how they communicate, how the enemy weapon systems function and work. So I used a lot of that technical intelligence in my first tour in Iraq. And it was noticed by a general officer that I worked for. He said you should go to NSA, the National Security Agency. And I was like, what’s NSA? But I learned quickly that it’s where people like me, those who are very technically oriented, but also wanted to serve their country in an intelligence capacity, i’ts where they thrive. So it was a great move to get into NSA. And so my focus and specialty there became signals intelligence. So really understanding networks and communication systems and how to exploit them and all the kind of nerdy side of intelligence.

[00:05:32] Gary Bisbee, Ph.D.: I’m just wondering if all that background led to your entrepreneurial interest in Olive and some of your other entrepreneurial interests.

[00:05:41] Sean Lane: Oh, it certainly did. I mean, one of my biggest tasks at NSA was to connect all the data together. We had an extraordinary amount of data, the biggest big data problem in the world, I would say, at NSA. And I was part of a small team that had the unique challenge of making sense of all that data, making it usable, and then allowing it to connect to other applications, new applications, that we were building, software. So I led software teams. I learned just a ton about technology across the whole stack, as they would say. When I got out of NSA in 2007, my first company that I started was a software company, building tools for the intelligence community. And even at Olive, many of the things that I did back at NSA and learned at NSA, we still do today at Olive.

[00:06:28] Gary Bisbee, Ph.D.: Well But you left NSA in 2007, but then in 2000, what was it, 15, after you’d founded Olive, it seems like you went back to NSA for a couple of years. Is that true? What led to that?

[00:06:41] Sean Lane: Well, I didn’t go back in 2015. So I had left NSA in 2007. I started a company in defense, but I didn’t actually relinquish my clearance until like 2015. So I was still kind of inside the building, as they would say, on occasion up until 2015 and I finally decided no more polygraphs. It’s time to move on to healthcare.

[00:07:07] Gary Bisbee, Ph.D.: I’m sure you will always have an interest in NSA. Are you able to follow it from the outside at all?

[00:07:13] Sean Lane: Well, it’s one of those organizations that’s super secretive, as it should be, and many of the sources of methods are highly guarded. And I don’t have a top secret clearance anymore, so I don’t have the access or the need to know, but I get to watch it and watch what we’re doing as a military and the strategy where we’re deploying globally. And as a spectator now I can at least imagine what’s happening behind the scenes at NSA.

[00:07:38] Gary Bisbee, Ph.D.: You bet. Well, let’s turn to Olive, a super interesting company. What led to the founding of Olive, Sean?

[00:07:46] Sean Lane: So I had just sold my defense company and I was living in Baltimore, Maryland, and my hometown, it’s called Gallipolis, Ohio in Southeastern Ohio, was having this just excruciating battle with prescription drug abuse. It was getting really close to home, effecting friends and family members. And I got fed up with that problem. And I started working with my hometown and specifically the hospital in my hometown, to say like, what’s going on here? How come we can’t tell people are doctor shopping? How come we can’t know that they were at an emergency room 10 minutes ago or ten hours ago? And I realized at that point that healthcare didn’t have the internet. Nothing was connected together. Systems didn’t talk to each other. Software didn’t communicate with one another. And that lack of an internet is what led to Olive because what I realized is that we had put human routers where these systems didn’t connect. And we had done it at such magnitude that there were 4 million human routers at very least in healthcare, so a trillion dollars of cost. And that’s kind of what led to the idea.

[00:08:53] Gary Bisbee, Ph.D.: Well, can you describe Olive for us please?

[00:08:56] Sean Lane: Sure. So Olive is an automation company for health. And that’s a very broad statement because what we do today is quite broad. We help health systems and hospitals, as well as health insurance companies, across their entire enterprise, automate various things. And as a patient, when you walk into a doctor’s office, you get handed the clipboard with the string and the duct tape around the pen. That’s just a symptom of the need for automation across the board. So there are so many different areas. We do a lot of work in the financial area of billing and revenue cycle. We’re doing a lot of work in supply chain and clinical areas. Really across the entire enterprise, there are so many places and for us to automate. So we take that very seriously and that’s really our life’s work.

[00:09:49] Gary Bisbee, Ph.D.: Well, you use AI and we’re all familiar with the term. I’m not sure we’re as familiar with what actually AI is, but could you just describe AI and how you use AI for us, please, Sean?

[00:10:04] Sean Lane: Sure. So I’m a bit old school on AI in that I kind of take the Turing methodology of AI, which is that artificial intelligence is something that’s hard to distinguish from a human. In fact the quality of AI is often measured by a thing called the Turing test, which is your inability to tell it apart from a human. But there’s other pieces that are important. Machine intelligence is kind of the other half of AI, which involves things like machine learning and deep learning. Sometimes those tools are used when creating an artificial intelligence and sometimes they’re not. At Olive, we do both. We do AI. We have these AI workers that are difficult to tell apart from a human, but we also use machine intelligence, machine and deep learning, to do a lot of the heavy lifting. In fact, all of our tools that do basic automations are actually built on neural networks called convolutional neural networks, or CNNs, which allow us to kind of understand the software of healthcare. And it’s a constantly learning model.

[00:11:06] Gary Bisbee, Ph.D.: Where are we at? If healthcare was the application of AI machine learning, neural networks. Where are we at in healthcare? If this was a baseball game, what inning would we be in?

[00:11:19] Sean Lane: Oh, we’re still in the top of the first inning. I think we have so much work to do. We’re having a lot of success using artificial intelligence, automation, some deep learning, some machine learning in the administrative and operational areas of both health systems and health insurance companies. We’re having a lot of success using a lot of these convolutional neural nets and computer vision capabilities inside clinical areas, specifically in radiology, but there’s so much more to go. We have to really think about how we use AI to free up human capacity because, really, we have a human capacity problem in healthcare. There’s just not enough people. And we’re wasting too much of people’s time on a lot of the things that we should be relying on artificial intelligence to do.

[00:12:09] Gary Bisbee, Ph.D.: As a lay person, what challenges should we be aware of in terms of the application of AI?

[00:12:15] Sean Lane: So I think it becomes very important to ensure that, when we train these models, that the results are the most desirable results. And oftentimes we put ourselves in a position to try to compare it to perfect and it will never really achieve perfection. The question is, can we achieve results that are much better performing than the human results? And that’s the thing that we should really focus on, but also those models are really hard. They call it the black box problem. They’re really hard to investigate because what’s happening, the machine intelligence goes beyond human intelligence. It’s hard to understand how they’re coming up with the solutions that they came up with. So there has to be better ways to inspect the models to ensure that we are training them in the right way to get the right outcome.

[00:13:09] Gary Bisbee, Ph.D.: So I know Olive works closely with health systems. Can you describe how you work with health systems?

[00:13:16] Sean Lane: Sure. So when we engage with a health system, and this has evolved over the years, when we engage with the health system, we like them to take an enterprise wide approach to using automation to transform their organization. And that’s really the altitude we like to fly at, which is, let’s commit to automation in order to transform the entire organization wing to wing. And when we do that, we offer an entire marketplace of applications and capabilities. About a third of those things are built in-house by Olvie. We call them Olive originals. But the other 70% are partners that we actually, we enable. So they basically pick through that marketplace to apply automation to different areas within the organization.

[00:14:05] Gary Bisbee, Ph.D.: How about health insurers? How do you work with health insurers then, Sean?

[00:14:10] Sean Lane: We have an incredible utilization management solution for insurance companies. It is actually one of the most remarkable uses of deep learning and true AI as it pertains to the machine intelligence side, which is deep learning. And we’re able to use these neural nets to make real-time decisions on prior authorizations without a human being involved at all. That is kind of a giant leap forward in what used to be possible versus what is possible today. So our primary effort with health insurance companies is to completely automate through AI their utilization management system.

[00:14:50] Gary Bisbee, Ph.D.: Thinking as an entreprenuer, it’s always interesting kind of the evolution that you go through as an entrepreneur. But at what point did you realize Olive was really starting to have the impact that you wanted it to have?

[00:15:05] Sean Lane: So, I think when we first came out with Olive, our customers really directed us where to go. We said, Hey, we have this capability that can automate virtually anything. Where should we start? And they said, well, we have a lot of repetitive tasks in the revenue cycle. And so we went to the revenue cycle, and sure enough, we created a new sense of human capacity. We freed up so much human capacity for them. The inflection point was when they said, can you start going to other areas? In fact, we’ll give you full view of the entire enterprise. Figure out where we can deploy this more. So our customers started to ask for more. All of our contracts started to get bigger and they pulled us into other areas. And at that point I knew this wasn’t just a point solution for revenue cycle. This was a movement to really transform the entire enterprise.

[00:15:59] Gary Bisbee, Ph.D.: We can sense the opportunity. Top of the first inning. Olive is probably the home team by the way. Top of the first inning. But what are the challenges that you look forward to over the next five or 10 years? I mean, as you see this continuing to unfold, Olive continues to grow down these paths through the health insurers, through the health systems. What do you see as the major challenges?

[00:16:26] Sean Lane: One of the biggest challenges, and I know people would probably expect me to say it’s a technology or it’s a particular system, that status quo that we have to change. I actually think all that is inevitable. Like we’re going to have the right technology. We’re gonna hire the right engineers. We’re going to force status quo to change. The biggest challenge is scale. In order to have a real impact on healthcare, we have to do this at enormous scale. There’s almost 10 billion hours of human capacity wasted every single year in healthcare because of a lack of automation. And if we’re going to actually make a big impact to that, we have to be big enough to matter. And building a big healthcare technology company, it’s not only hard, it’s rarely done. And surviving for that long, having the perpetuity and continuing to invest in a sustainable that grows year over year for a long enough time where we can turn and say, we have a billion dollar R&D budget, and we have the ability to impact healthcare so that every single person that interacts with healthcare actually feels the difference. So the challenge is scale. It’s getting big enough to matter.

[00:17:33] Gary Bisbee, Ph.D.: Yeah, well, as a long time director, a Cerner, I get that point very well. For sure. How much will acquisition be part of your strategy versus organic growth?

[00:17:45] Sean Lane: You know, we’ve had some acquisitions already and they’ve been absolutely game changing for our business. They’ve been very strategic. We acquired a company called Verata to pull us into the payer space, which was an excellent acquisition, incredible team, incredible technology. We acquired a clearing house so that we can provide even better capabilities for our current customers. And you know, in the future, when I first thought about acquisitions, I thought, oh, that’s something that a certain kind of company does, but the big tech companies of the country don’t do that. And I was very wrong. I went back and looked at Microsoft’s acquisitions since their inception and they’ve spent over $200 billion in acquisitions during their inception. So I think the inorganic growth is just part of building a big company. So we will be very strategic about it, but it certainly will be something that we want to develop a muscle for.

[00:18:44] Gary Bisbee, Ph.D.: How much capital have you raised to date at Olive?

[00:18:49] Sean Lane: We’ve raised a little over $900 million in capital.

[00:18:54] Gary Bisbee, Ph.D.: Okay, well that would suggest that, to build the scale you’re talking about, you continue to raise money through the years, I’m sure. One other question from you as an entrepreneur, thinking back to 2012, when you formed, have you met your expectations? Have you exceeded them? Have you not met them? Where do you stand on that scale, Sean?

[00:19:17] Sean Lane: So, the expectations have evolved quite a bit. Initially the challenge that was given to me was to move to Columbus, Ohio, and build a billion dollar company. And I thought, oh my gosh, that sounds insurmountable, like a mountain too high. But we you know, we crossed that path a couple of years ago and now have exceeded that quite a bit. And I realized that the valuation is not an expectation that you should really be thinking about. It really is the dramatic impact that we can have on the healthcare industry itself. So I start to measure our success based on the human capacity that we can free up. That 10 billion hour number, I wake up thinking about that in the morning. I go to sleep thinking about that at night. That is a huge drain on just the US healthcare industry. It’s wasted time. It’s wasted. Time of humans is our most precious resource in healthcare. And we are, right now, leaking 10 billion hours worth. So, my expectation is that we recover that 10 billion hours and we’re not going to stop until we do it.

[00:20:29] Gary Bisbee, Ph.D.: Yeah, well, good for you. We need it for sure in healthcare. As an entrepreneur, what skills are necessary to be a top-notch entrepreneur, would you say, Sean?

[00:20:42] Sean Lane: Well, leadership, number one, two and three. I’ve always been a student of leadership, but you always are a student of leadership. And I think as we’ve grown, it’s become more acute to me how important leadership is in growing a company I think, as an entrepreneur, sometimes you’ll rely on your technical skills, your ability to code, your ability to sell, to architect a solution. But for scale, which I said is going to be the hardest challenge, it’s leadership. And I made it a point to really get serious, like even more serious about leadership over the past few years. And I’ve developed a methodology that I try to follow with leadership. So it’s been very, very important.

[00:21:32] Gary Bisbee, Ph.D.: Can you share the outlines of the methodology?

[00:21:35] Sean Lane: Yeah. So, I call it Love to Lead. And the reason I use that term is you have to love to be a leader to be a leader. And you actually have to love people in order to lead. And L.O.V.E. is actually an acronym. So I’ll share that with you, that the L stands for leadership and it means everything is a leadership problem. So if your code breaks, if your customers aren’t happy, if something went wrong, it’s a leadership problem. And that should be always your first thought. What’s the leadership problem that led to this? The O stands for otherhood and it’s really the state of being an other, really thinking about others the whole time when you’re leading an organization. How are people feeling? How are they receiving this information? If I had to do like hyper empathy and put myself in their shoes, what would I be feeling? And you have to really think about that often, otherwise you think about yourself or the immediate team around you. V is about vision. One of the things I love is when a vision comes to life. And I decided that if I like that, I bet other people do too. So we make it a point to ask our team what their vision is and, whether it be a simple task or a big strategy, I want to hear people’s vision. And then we can work really hard to help that vision come to reality. And the final letter, E, is expectations. And I think all emotions come from expectation. If you don’t hit it you’re upset about it. If they’re exceeded, you’re excited. And the point about expectations is talk about them all the time. These are my expectations. What are your expectations? If they’re front and center, then you have less of those kind of chaotic emotions that could emerge.

[00:23:22] Gary Bisbee, Ph.D.: Well, we see the leadership framework. Obviously you were excited about leadership. You can just tell in your body language. What’s the most challenging part of being an entrepreneur?

[00:23:32] Sean Lane: Well, I think maybe it’s different for everyone. Me in particular is I am a problem solver. I love to build things. I love to get into the mix. And I’ve learned at a company that has now 1400 employees that that’s not helpful most of the time. So as a leader, I’ve had to change my tact and really just empower others to handle things. And the beautiful thing I’ve learned is that they are so much better than me at most of these discrete tasks. And the solutions they are coming up with are better than I ever could. The software they’re building is certainly better than anything I could’ve ever built. So it’s really humbling, but also it’s what will, again, allow for that scale.

[00:24:16] Gary Bisbee, Ph.D.: So let’s just think about highs and lows as an entrepreneur for a moment. I’m thinking maybe the high is when you reach that billion dollar valuation. What’s the low point, Sean?

[00:24:29] Sean Lane: As you said earlier, as we talked about, I did five combat tours. And when you’re in combat five times, things don’t affect you the same way. It does add a bit of perspective. Probably the most shaping part of my life was being deployed in a combat zone. But, what really is the low point for me is when something happens that discourages my team. And for me, it might not phase me. I might think no big deal, I can handle this. But when something happens, whether it be a customer had a bad reaction to the product or they missed a quarter or missed a number or the press wrote something not flattering, whatever that may be, I feel for them and I know it’s tough to deal with those things. And that’s really the heart, those are the low points, is when that happens.

[00:25:22] Gary Bisbee, Ph.D.: Yep. If you hadn’t founded Olive and weren’t leading Olive now, what would you be doing?

[00:25:29] Sean Lane: Oh, I would probably still be in the defense industry I found that my skills really worked well there and it was a really important mission. I do find myself really only attracted to what I call life or death industries. When human life is at stake, that’s what drives me to it. And so if I wasn’t in healthcare and having started Olive, I would likely still be in defense, trying to protect our war fighters.

[00:26:00] Gary Bisbee, Ph.D.: You’re pretty young to be asking this question, but what would you like your legacy to be as an entrepreneur?

[00:26:07] Sean Lane: As an entrepreneur, I would like my, and this is probably not my whole life legacy, but specifically as an entrepreneur, I would want it to be about my L.O.V.E. to Lead methodology and me as a leader, not as a technologist, not as a great idea guy or somebody who wwars baseball caps to interviews with Gary Bisbee, but more importantly I want it to be about being a great leader. And I got work to do to get there, but that would be really important.

[00:26:38] Gary Bisbee, Ph.D.: Well, you mentioned it. I must ask it. What about the legacy for your life as opposed to just being an entrepreneur?

[00:26:45] Sean Lane: Well, I think the legacy for my life are my children and I’m really hopeful that I can provide for them and environment to truly follow their dreams. I want to instill all the qualities of my life that have helped me. My wife and I are really thoughtful about how we raise our children and make sure they have a great household. Faith is important to them and us, and I want to make sure that that’s part of their life and that’s the legacy that I want to leave for them.

[00:27:17] Gary Bisbee, Ph.D.: Well, well said, and I think that we all think, to one degree or another, that that should be our legacies. This has been a terrific interview, Sean, as I expected. You’re a very engaging, thoughtful person and have accomplished so much. I have two questions of advice. One would be, for entrepreneurs or people that are thinking about being an entrepreneur, what advice would you give them?

[00:27:42] Sean Lane: You I was at HIMMS recently, the big healthcare conference, and I looked around and I saw all the brand new booths and all the card tables with brand new start-ups on them. And I thought to myself, wow, they’re beginning such a long and incredible hourney. And the advice I would give is just to never stop, to continue to work through all the hard times, to continue to pursue the vision that they have, but to start early thinking about leadership and start early trying to become a great leader.

[00:28:16] Gary Bisbee, Ph.D.: Okay, well then you’re moving right into the second group that I’d like to ask your advice for. And that would be for up and coming leaders, not necessarily entrepreneurs, up and coming leaders. What advice do you have for them, Sean?

[00:28:30] Sean Lane: It’s going to be a pretty practical one. But, as a kid, I had a basement bookcase full of leadership manuals. And now we have the internet and it is amazing. There is incredible amount of content out there about leadership. Now the hardest part now is figuring out what methodology you want to embrace. So I would say use YouTube, use the internet, read voraciously around the topics of leadership, and then figure out, of all those ingredients, what ones that you’re going to make part of your system of leadership. And that doesn’t have to be immoveable. It could change. But consume a lot of content, pick what your particular methodology is. Coming up with the L.O.V.E. to Lead methodology was one of the easiest way to cut through the noise around leadership. And I would recommend doing that.

[00:29:23] Gary Bisbee, Ph.D.: Sean, we appreciate your time today. This has been a terrific interview. Thank you.

[00:29:28] Sean Lane: Thanks, Gary. I’m grateful. Thanks for the opportunity.

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