Rachel Gollub is a distinguished engineer, programmer, and entrepreneur with a storied career in Silicon Valley: she started her career as part of the founding team behind the Java programming language and ended it as CTO of healthcare giant Optum. Along the way, Rachel managed to start several companies on top of a quick stopover at Stanford. In this episode, Rachel reflects on her experiences working alongside tech luminaries like James Gosling and dives into the challenges and triumphs she encountered while navigating the male-dominated field of technology. What does it take to build a successful team in the fast-paced world of startups? How do you bounce back from setbacks and learn from failed ventures? Rachel shares her insights, drawing from her rich experience in taking ideas from inception to reality, and the critical role of adaptability and innovation in entrepreneurship. Join Vivek and Rachel in this episode of 'The {Closed} Session' as they explore the intersection of engineering, entrepreneurship, and healthcare AI. The conversation delves into her thoughts on the current state and future of AI, particularly in healthcare, where she's been a driving force in integrating advanced technologies to revolutionize patient care and outcomes. Stay for Rachel’s unique perspective on where technology is headed, especially in the realm of healthcare AI.
Rachel Gollub is a distinguished engineer, programmer, and entrepreneur with a storied career in Silicon Valley: she started her career as part of the founding team behind the Java programming language and ended it as CTO of healthcare giant Optum. Along the way, Rachel managed to start several companies on top of a quick stopover at Stanford.
In this episode, Rachel reflects on her experiences working alongside tech luminaries like James Gosling and dives into the challenges and triumphs she encountered while navigating the male-dominated field of technology. What does it take to build a successful team in the fast-paced world of startups? How do you bounce back from setbacks and learn from failed ventures? Rachel shares her insights, drawing from her rich experience in taking ideas from inception to reality, and the critical role of adaptability and innovation in entrepreneurship.
Join Vivek and Rachel in this episode of 'The {Closed} Session' as they explore the intersection of engineering, entrepreneurship, and healthcare AI. The conversation delves into her thoughts on the current state and future of AI, particularly in healthcare, where she's been a driving force in integrating advanced technologies to revolutionize patient care and outcomes. Stay for Rachel’s unique perspective on where technology is headed, especially in the realm of healthcare AI.
Welcome to The Closed Session. How to get paid in Silicon Valley with your host Tom Chavez and Vivek Vaidya.
Vivek: Hello and welcome back to season four of The Closed Session. This is Vivek Vaidya and for this episode I'm by myself. But I have an amazing, amazing guest I'm about to introduce. I worked with this person in my first job in Silicon Valley. In fact, I knew of her even before I started my job, because I read a lot of code written by her as I was learning. the Java programming language. So without further ado, we have Rachel Gollub with us. Rachel is a distinguished engineer. She was on the original team that wrote the Java programming language. She's an entrepreneur, she's an academician, academician? Is that... that's a word? I think. And, uh, yeah, I'm really excited to have Rachel on this podcast with us. Welcome, Rachel. So Rachel has a bachelor's degree in computer science and Russian literature from, uh, from Caltech. She also has studied military history later on in her life. And she worked at the digital library initiative at Stanford as well, after a stunt... stint at Sun Microsystems. And then she's also started a couple of companies, which we will talk about momentarily in the podcast. So Rachel, great to have you here. How you been?
Rachel: Pretty good. How about you?
Vivek: I'm great. It was a good Thanksgiving break. I, uh, was quiet. I read a few books and cooked a little bit. But yeah, so, uh, let's, uh, let's get into this, uh, this talk, shall we?
Rachel: Cool.
Vivek: All right. So you almost worked at Netscape and then almost at Amazon in the early days, right? But you ended up at Sun. How'd that happen?
Rachel: Actually, it was really funny. My first job out of college was at a startup. And you know how startups go sometimes. Sometimes they're great. And sometimes they don't last very long. So, you know, after working there for less than six months, I think... they kind of took us all out on the patio and said, we have no more money, you can all go home. So a bunch of us got together and we're like, okay, what are we going to do next? So a group of folks said, you know, um, including Jamie Zawinski, who I worked with there said you know, I want to go found this browser company. You want to come with me? And I was like, you know, I, I don't know. I kind of want to do more challenging programming. Yes. Can you believe I said that? So, then he said, well, you know, my friend, Jeff Bezos is going up to Seattle to put together an online bookstore and that's probably more in your area. I'm like, that sounds great, but you know, my husband's in grad school and I can't really move right now and it would be years. And, you know, so I think we're out of luck there. And so some of the other folks were like, well, we came from Sun and we're going back to Sun. You want to interview there? And I was like, yeah, sure. I mean, they're, they're in the area, you know, they're cool people. I'll try it. So I did. And that's how I ended up at Sun Microsystems. And then, you know, later in the Java group.
Vivek: Wow. So, what was it like being part of that team that developed Java? How was it working with James Gosling?
Rachel: Oh, it was fantastic. The guy is so nice. It's, it's unreal. And everyone was incredibly accepting, you know, they're really excited to see me. I had ended up, you know, I started in Sunsoft and then my friend Headley was just like, Hey, I found this really cool thing that a group is doing and, you know, we should go interview there and see if they'll let us join them. So, you know, I went with him and we interviewed and they hired us both and they really invited us to do some of everything and it was super cool and I met really nice people and I have to say, you know, not every job I've had has been spectacular, but that one really was.
Vivek: That's amazing. Like, and going back like what, 30 years now? That's uh... I can't believe I just said that. But, uh,
Rachel: Yeah, I know, right?
Vivek: But no, it was, it was quite amazing, right? Because it was the first time. I think it was the first time a company had decided to create a programming language from scratch, right? Cause, uh, cause C, yeah, you know, it was Bell Labs and, and all of that, but that, that came out as a research effort, I think. But Java was the first time a company decided we're going to create this programming language. And, uh, look what it's become now, right? You must feel like such a proud, uh, proud parent almost. No?
Rachel: I totally do actually. You know, it's really funny too, because people ask me, you know, what's your favorite programming language? And I'm like, you know, of course it's Java.
Vivek: Yeah.
Rachel: And you know, when I interview people, one of the things I frequently ask is, so what do you think of Java?
Vivek: Yeah.
Rachel: You know, and the people who know me are just like, oh, it's fantastic. Absolutely. But then like people who have never heard of me are just like, eh, you know, I don't know. I don't really like it. And it's like, really taking notes, you know, what don't you like?
Vivek: So do you hold that against them?
Rachel: No, not at all. Because realistically there are so many good languages out there now, you know, it's... it was the first of its kind in a lot of ways, but it's certainly not the last.
Vivek: No, no, I, I totally un... hear what you're saying, right. Cause as I was mentioning earlier in the introduction, I read a lot of source code written by you, the way it happened was when I came to the US for a grad school, one of my professors we had to do a bunch of courses and most of the courses that were being offered that quarter, I had already taken as part of my undergrad. So I went to my advisor and said, hey, what should I do? And he said, well, you want to do an independent study. I was like, what is that? He said, well, we agree on a topic and you will study it for three months and you do some assignments, etc etc. and I was like, well, so I'll be completely on my own, just learning at my pace. He's like, yup, like, great. What are we learning? Says there's this new programming language out called Java. And so why don't you learn that? I'm like, okay. And then it's buttered my bread for majority of my career like yours, right? And yes, now I do end up programming in, in many different languages, but it's very comfortable, you know, Java is very comfortable for me. Um...
Rachel: For sure.
Vivek: But now, you've seen the trajectory, you've seen the language evolve, you've seen other languages come out, and you've, as you said, you're using them yourself. How has your approach to software engineering changed since those early days at Java to now?
Rachel: You know, realistically, it's changed constantly, like at every job, I've learned something new. And I have a bunch of friends who are part of the lean startup movement. So they've been, you know, really influential in how I look at startups and how I look at software development in general. I think one of the biggest changes as I've gotten older is a lot more appreciation for good DevOps and infrastructure and testing and you know all the things that seemed sort of by the way when I was much younger and now I'm just like these are critical because you know you can't expect somebody while they're coding to think of everything. The other really big change, of course, is, you know, Copilot, right? I mean, we didn't have that until very recently, and that's a game changer, you know, it's so nice to just tell it, like, you know, do this part of the code for me or remind me how to do that thing I forgot or whatever. So you know, the whole process is sort of changing around that because, you know, it's much more a process of figuring out what the pieces are rather than how to code every individual piece. So, you know, it's, the skills are different.
Vivek: Do you use Copilot?
Rachel: Yeah, I totally do.
Vivek: Yeah. Yeah, it's... I haven't used it as much. I think it's just something I need to start. It's a habit I need to start developing. I still, you know, when I'm looking for something, I still end up typing it in Google. It's just... it's just force of habit so far. But I've seen other people use it. And, uh, one of my, you know, one of my things with tools like Copilot is that I think code should be readable, right? And understandable by the average software engineer, right? And my worry with tools like Copilot is sometimes it ends up producing code that is very cool, it does the job, but it's hard to understand by the average software engineer. Have you had that experience?
Rachel: You know, I think for the most part, I've used it for small things. So I've had that occasionally, but for the most part, I'm just like, okay, I can't remember how to, you know, write to a file in this particular way in this particular language, just like remind me what that is. And, you know, most of the time, actually, it'll use libraries that I don't have or I've never heard of. So I have to go through and figure out what those are, you know, it's not like zero effort, but every time I use it, I learn something new or I'm reminded of how to do something that I'd forgotten and... You know, the way it's built into Visual Studio, it's just so easy to use, you know, it's, I really think they did a good job with that
Vivek: Yeah. So let's talk about your founder and startup experience a little bit. You've worked at many startups, right? DDoS mitigation, photo editing, gaming, wine, even though you don't drink wine. We'll talk about that in a minute. Healthcare. So that's quite the spectrum. As you look back, tell us about the people that you work with. What were some of the commonalities across the best teams at these, these startups? What were some of the things you didn't like about, about the teams that you were with?
Rachel: So actually, I'm working on a book. We'll see if I ever get to the point where I finish it, but working on one about what makes a good team. And, you know, the essentials actually, you mentioned military history, you know, I have a master's in military history. So one of the things that I took away from that was the core principles of maneuver warfare and how teams work together, because of course that's critical in the military, you have to have teams that, you know, coalesce. So sort of, you know, the business take on it is that you really need to have mutual trust. You need to have experience, you know, people who have experience with each other and the kind of things you're doing. You have to have common goals, you have to be shooting for the same things. And you have to feel like what you're doing is going to make a difference. Like you can have all the other things, but if your goal is to change the background of a page from blue to green, probably you're not going to have a lot of job satisfaction, you know? So all of those things are really important. And my best experiences have been the places where I had all of those things where, you know, everybody worked together, everybody liked each other and, you know, we were going toward the same thing. So when I started founding companies. That's what I built toward, you know, if somebody, somebody could have been fantastic and a really good coder, but if they just couldn't, you know, they didn't have the same goals or they didn't really, people didn't trust them, they just weren't a good fit for the team. So I'd suggest they work somewhere else.
Vivek: Yeah. No brilliant jerks. That's what we say. Uh, you know, that's, it's, it's hard. It's hard. If you have people like that on the team, they're so corrosive sometimes.
Rachel: Yeah.
Vivek: So you were a guest on our community call just about a week ago. And you, you said that about your startups, that is some of them went nowhere, some of them became nice lifestyle businesses and some were successful. So tell us about the most negative experience. What were the lessons you, what were the lessons you learned?
Rachel: That's a great question. Okay. So the most negative experience was probably, um, so I agreed to start a startup with a friend. And you know, he'll probably listen to this, he's currently CEO of Treasury Prime. And so it was totally not his fault. It was a negative experience. He's great like stellar. But what happened was we decided to found a startup together and we went out looking for customers, looking for funding, and we spent like six months just constantly going to people, trying to sell it, trying to get people involved, trying to figure out what we were doing. And after six months, we had no traction at all. And part of the problem was that the idea for the time was a little bit hard to explain to people. I mean, now it would be super easy. Like you need a way of visualizing your big data, right? Of course you do. There's a ton of stuff out there now to do that. But we were like maybe five years early on that. And so people are like, I don't understand what's big data. What are you talking about? And, oh, it was the most frustrating thing. And then I got an offer to co-found a different company and I was just like, what do I do now? So that whole thing, I ended up inviting Chris to come along and he did and, you know, that. that sort of solved that problem. But it was hard for both of us to give up the startup that never even really got off the ground.
Vivek: Yeah. Sometimes you get too attached to these things, right? Because it's your baby and you don't, you know, in your head, in your mind, it's a great idea and the time has come. And, uh, but sometimes the market is not just ready for it, right?
Rachel: Right.
Vivek: That happened to us. I mean, and that's where, that's why I always say. And Tom and I both say this, like, luck plays such a huge part in getting you to where, where you get to, because arguably, Krux was the third iteration of the company that we ended up building, not, not by us, but there were two other, there were other people who had tried to do something similar twice before us, and they were moderately successful, but the way in which we did things was only possible because of when we started Krux. It was the perfect time, like computing was coming up and big data technologies like Hadoop were just starting to come out. So it was, it was just, it was the perfect time really. So as you compare, you know, the negative experiences and the startups that didn't work well, to ones that did and that were successful, what was different? What went differently on at the successful builds?
Rachel: Well, you know, I kind of have to list that one as an exception, because we tried really hard, but it was the wrong time. But for the most part, you know, the biggest difference has been the level of commitment. Like the first couple I started, I wasn't totally committed to, and that turned out to be a problem, because of course there are ups and downs, and when you hit those downs, sometimes you're just like, you know, maybe I'll give up on this, which is deadly if you're trying to do a startup because there are always going to be ups and downs, right?
Vivek: Yep.
Rachel: And so then once I got the sense that I really did need to commit to these things, if I was going to do them, then it was partners who maybe weren't totally committed. And again, this isn't Chris, right? Yeah. This is other partners that I'm thinking of. But, you know, they were just like, well, I'm kind of doing this while I'm waiting to do something else. And that's... that's terrible. So, you know, the ones that really succeeded were the ones where I actually ended up not only committing to it, but finding partners who were really willing to commit. And we were just going to like, you know, make this thing work no matter what.
Vivek: Yeah. Finding the right partner is so important. That's why like, I'm so lucky to have been working with Tom for the last 25 years because you just need someone. In fact, like at one of our other one of our super{set} companies, uh, these two founders, we were talking to them last week and they were also together reflecting on the fact how important it is for the two of them to be together in that journey. One was telling a story where they were on the road and, uh, uh, it was tough commute traveling for all sorts of reasons. And at 2:30 in the morning, they needed some support. So they just called up their partner in their company and pick up the phone and they ended up just talking to each other and that kind of calm things down. So finding the right partner is so important. I completely agree.
Rachel: Yeah.
Vivek: As you now reflect back and think about how it all started for you as a founder, right? What motivated you to, uh, found your first company? Was it a natural next step for you in your, whatever point you were in your life or is this something you've always wanted to do?
Rachel: Honestly, I've always been sort of an entrepreneur. You know, when I was a kid, I used to crochet dolls. I do a lot of crafting and I sent my poor brother out to sell them house to house because I was just like, Hey, I'm making them, somebody should buy them.
Vivek: Right.
Rachel: And you know. So I'm kind of in that habit, and the first, the first company I actually founded, where I actually got to write down, you know, Rachel Gollub, CEO, and, you know, fill out all the paperwork, was right after I left Java, because I had some disagreements with some of the folks there, totally friendly disagreements about what should go into the language and what people should do themselves. And so I ended up, you know, feeling like a lot of the libraries were kind of incomplete. And remember this was way back, like now they're over complete, right? You can do everything 10 different ways. But at the time it was a really bare bones language. And I thought there were some things people needed. So I wrote a bunch of stuff and then I started selling it. And so, you know, it was one of those things where, like, I'm in a unique position to know how to do this and to be able to solve this problem for people. And that was the one, one of the ones that actually went well. So, you know, realistically, like, you know, having my first real, like, tech startup experience go well really made a big difference.
Vivek: Yeah, that is so important because it just gives you that, that confidence, right? That yes, you can do it. And, uh, regardless of how big or small the success is, the fact that you were successful gives you an insane amount of confidence. But again, as you, as you look back, I'm sure it wasn't all smooth sailing, even at your first first startup. So, you know, and, and sometimes as you're going through this, sometimes you think things in the moment, things A, B and C are so important, right? But then when you reflect, you're like, nah, that wasn't that important after all, right? So what seemed important to you in, in that moment, but realize you realize now in retrospect that it was not.
Rachel: Wow, that's a really good question. I think the biggest thing was well, you know, one of the things that I discovered, this isn't, this isn't entirely an answer to the question, but one of the things that I did notice is that being completely dependent on making money fast is a terrible way to do a startup.
Vivek: Yes.
Rachel: And that was one of the things that I learned early because I, set myself up in situations where I had a very short amount of time to make money. And so, you know, when I didn't make money in that time, then, you know, that was a critical failure and I had to stop. And that's, you know, that's a terrible way to go into a startup because startups are generally slow. I mean, very few of them make a lot of money. And in fact, another founder I worked with, his first startup, Like they sold it for, you know, millions after six months. So he went into his next startup, like, Oh, the same thing will happen. And you know, like five years in when he wasn't making money, he was, you know, what did I do wrong? Why is this so terrible? It's such a failure. And I'm like, actually it was a terrific success. It just, you know, it wasn't going to be as fast as that first one.
Vivek: Yeah. Yeah. You're so right. That's why everybody who comes to work with us, we talk to them about this concept of delayed gratification, you know, and, and if you're going to come work at super{set} building a company with us, you just have to subscribe to delayed gratification. It is going to be a long build out, long doesn't mean 25 years, right? But you're looking at the next 10 years of your life that's the expectation we set. Like you said, things don't, things never go as fast as you would, uh, want them to, or like them to, so, uh...
Rachel: Yeah, that's a really good expectation to set too. I mean, that's a, that's a good way to prep people for what's coming.
Vivek: Yeah. And if things, if things go. faster and you, you get to your outcome or exits sooner than what you expected, then hey, that's great. But at least to your point, we've set the expectation to be one of delayed gratification. So now let's talk about teams at startups, right? And you've, uh, you've recruited many teams, you've managed a number of them. What do you look for when you're building an early team? Do you look for pedigree? Or what qualities and mindsets do you look for?
Rachel: It's not pedigree so much as I look for people who really enjoy solving challenging problems, right? Also, like I said, people who get along really well with other people who really understand collaboration. One of the things I've started doing, I want to say recently, but it was like 10 years ago, is, um, getting everybody who's going to be involved in working on something together with anyone I'm interviewing and just spending a couple hours together coding something together. Because what I care about isn't that they know how to look things up. What I care about is that they're comfortable asking questions, answering questions, talking with people, that there's some kind of connection they can make during that time. Because that's really, you know, that's a good predictor of success. So the people who, you know, don't want to ask any questions, don't want to talk about what they're doing. You know, I'm like, collaboration may not be one of their strengths and again, that may work great somewhere else, but you know, in one of my teams, that's not going to work well.
Vivek: Yeah, that's so, that's so important and wise, right? Like I do the same thing cause maybe I was trained by, I was trained by you. So, uh, so, you know, the fact that, that, in fact, I remember when you were interviewing me and whatever, I forget what question you had asked me but I, I wasn't able to get to the final answer and then when we talk later, you explained to me that, look, I wasn't looking for the right answer. I was looking for your process you went through and the conversation we had that you kind of led us to think through the solution to the problem. And I've kind of embraced that throughout. Like you said, it's what questions you ask, are you able to talk through what you're doing? Are you able to stop and say, well, this works now and I've solved this problem, I'm going to do the next thing, so on and so forth. So, uh, yeah...
Rachel: Yeah, good memory, wow. That was the sort question, too. I remember asking you that one.
Vivek: It was the sort question, yes, I remember now. See, you remember, too.
Rachel: Oh yeah, totally.
Vivek: Anyway, so we've reached this point now, Rachel, in our podcast where it's time for a totally unpaid for promotion. So we invite our guests to promote whatever they want. Their favorite coffee shop, their favorite AI product, their favorite quilting, whatever you want. So the floor's yours. You can promote whatever you want. The entity, the product you're promoting is not going to pay us. So this is, so consider this a favor you're doing them.
Rachel: Okay. Thank you. So I guess. I'm going to promote the San Jose Museum of Quilts and Textiles because this place is fantastic. And if you think of quilts as like something that, you know, your grandmother did or something, then you have no idea what quilts are like now. I mean, they are fabulous. There are art quilts that, you know, look completely realistic, that are completely abstract. There are art quilts that are selling for, you know, millions of dollars.
Vivek: Oh, wow.
Rachel: It's a huge field now, and the, the Quilt Museum has a huge selection, like they have textiles from the 1800s, they have modern art quilts, they have all sorts of amazing stuff. They're only open certain hours, so you have to be in San Jose, and you have to be there during certain hours, but they do participate in things like First Friday, um, which is, you know, a terrific program where a bunch of places are open for free on the first Friday of every month. And if you happen to be in the area, you know, it's a fantastic place to visit.
Vivek: Well, there you have it for our listeners, the San Jose Museum of Quilts. Who knew quilts could sell for millions of dollars? I didn't know that. But there you have it, I'll definitely, if I'm there in the area, I'll definitely check it out.
Rachel: Excellent.
Vivek: Cool. So now let's talk about your most recent company, how do you pronounce it? Benefitter.
Rachel: Benefitter, yes.
Vivek: Benefitter, right? So what, what did you, what were you guys doing at Benefitter? And, uh, how did that come about? What happened?
Rachel: So, I mentioned before that my friend and I were trying to start this other startup, and we got recruited for this one. So, what happened was actually a group of people started a, a company called BenefitsMe, where they were, you know, they were going to try and do some fitness kind of benefits and stuff like that. And their belief was that, you know, programmers are interchangeable. You can just like hire a few people off the web to do some stuff and that's good for a product. So, you know, they learned they were wrong really fast and they decided that they actually needed technical co-founders. So, you know, through a friend of a friend, they came and talked to me and said, we'd like to invite you to be our, our technical co-founder and we're going to restart the company. And so, you know, I went to my friend and I was like, Hey, come along for this because, you know, this looks really promising. It's got people who have built startups before it's, you know, it's a really good idea. And what we were trying to do, you know, one of the guys there, who is the CEO totally sucked me in with like, we're going to destroy group insurance. We're just going to get rid of insurance companies. We're going to make the world a better place because nobody has to buy health insurance. And so, you know, I was like, I'm in, that sounds great. So, right. I mean, who wouldn't be? So, um, we ended up doing that. And, um, we started with six founders and, you know, after a few years, there were only two of us left, you know, which does tend to happen and when you have that many founders.
Vivek: I didn't know that six founders?
Rachel: Yeah. Yeah, it was crazy. Several of them made it like less than a year or just a year, but you know, Brian and I just kind of went, went with it after that. And so what we ended up starting to do was build a system to figure out, you know, Obamacare had just come out and people wanted to go onto individual insurance because this is a new opportunity. So we're figuring out, you know, companies had to pay a penalty if they didn't provide insurance for their employees, but we could find a point where they could give a certain amount of money to their employees and pay that penalty and then be able to come out ahead, basically. So the employees would get their own insurance that wasn't through their company. The company would pay less, you know, win all around. So we, we built a, you know, basically a Monte Carlo simulation of all of the, you know, given their employee list, like all of the possibilities and figured out, you know, what, what the ideal setup would be at that point. So we tried to sell that to companies and, you know, that didn't go as well as we wanted, but, you know, we had really cool technology. So another company bought us and we, you know, but they started, you know, they sort of had their own individual solution. So then they asked us to start working to sell group insurance. And, oh, oh, that hurt. But, you know, when you got to pivot, you got to pivot. So we did. And we started selling group insurance. And, um, so then all of us together were bought by UnitedHealth Group in 2019, actually. And in 2020 a new program came out called ICRA that let you let companies actually buy individual insurance for their employees without a penalty. So that's what we were looking for back then.
Vivek: Right.
Rachel: So at that point, you know, I was at UnitedHealth Group and I built a solution for that. And now I feel a little better about the whole thing.
Vivek: Yeah, so you, you were able to solve the original problem you set out to solve. It was just at a different company, two acquisitions later.
Rachel: Right. Exactly. And you know, I feel like I should do the dance for getting acquired twice, you know, but it worked out well. So it was nice.
Vivek: So, so, uh, what was that acquisition? Were you in that acquisition mindset? Like, did you guys want to get acquired or? The first time around second time around.
Rachel: The first time around, we definitely did because you know, we had been in existence for a couple of years and gotten whatever it was like five sales, you know, we at that point, we were looking for an acqui-hire or something like that and we actually did better than that, which was great. And really a tribute to, you know, our CEO who managed to get a better deal out of it. But then the second time, um, it was more our first funders were like, you know, Benefitter has been going for eight years. We need an exit. Like we don't care what the exit is, you need to get out now. So at that point we were looking for an acquisition and we had, you know, luckily we had bids from a number of different companies and the UnitedHealth Group bid was actually the one that looked the most promising for everybody. So we ended up going with that one.
Vivek: And then you had a very interesting kind of transition in terms of your role, like you, I mean, you were CTO at Benefitter and then Optum, but then the size of the teams you were managing were relatively speaking small, right? And then you were at UnitedHealth where you were the CTO managing an organization of 7,000 people. What was that like?
Rachel: Crazy. Honestly. I mean, it's not like I met very many of them.
Vivek: Yeah.
Rachel: But what, what happened there was honestly, so there are lots of levels of CTOs. And so, the organization I joined was employer and individual. And so, um, the CIO for that entire organization, you know, it was like, stop doing Benefitter come and be my CTO. I was like, And I'm like, sure, sounds great, you know, I can teach some people how to code and do all that stuff. I just did not realize the scale of the organization that she managed. You know, I was like, Oh, you know, maybe a few hundred people, but no, thousands of people, most of whom I would never, ever meet. And you know, some of whom actually, because of the siloed nature, like didn't even know I existed for a long time. You know, I, like I spoke at all the town halls and I, you know, gave talks all over the organization and, you know, outside of ENI, like all over UnitedHealth Group and all of that. But there were still people who just hadn't heard my name, you know, by the time I even left. So, I mean, just the scale was ridiculous.
Vivek: Yeah, no, I remember when I, when Krux got acquired by Salesforce, my team at Krux was 85 people all in and then I go to Salesforce and they, they thought I was capable enough. So they gave me the option of running all of engineering for Salesforce marketing cloud and I was like, sure, I'll do that. And overnight I went from managing a team of 85 people to managing a team of a thousand people. And, uh,
Rachel: Yeah.
Vivek: And that was a big change for me. And the teams were, this was actually way before the pandemic. So the remote work wasn't a thing, but we had teams in San Francisco. I had a team in Indianapolis is the biggest contingent and then a team in Canada in Newfoundland, Canada, and then, uh, London. So, yeah. So if you ask Pallavi, my wife, she'll tell you that. So there were, there were months when I was working harder at Salesforce than I was at Krux because of all the travel that I had to do. Yeah. So, but you also, you, you know, in your role as CTO at Optum, you were working on various AI projects as well, right? So, as you think about the work that you were doing and you think about the health tech space, now, what do you think about how these large companies think about data and AI? Where do they see potential opportunities for startups in particular in health tech?
Rachel: Yeah, so it's actually a fascinating ecosystem because, you know, when we were acquired, like, a year or so after we were acquired, I, you know, I talked to folks about retiring and what ended up keeping me there is the opportunity to train AI on incredible amounts of data because you know, UnitedHealth Group is one of the biggest insurance organizations in the world, right? I mean, it's, you know, it's, I don't even, you know, there were the number of people on the UnitedHealth Group plans changed all the time and employer and individual is one section of that, right? But we still had access to, you know, tens of millions of health records and, you know, pharmacy records and everything. And that was unbelievable. So, you know, that gave us opportunities to do correlations that we couldn't have otherwise done anywhere else. And so that was, you know, that was a definite draw. It's also, you know, the rate of acquisition for a company like UnitedHealth Group, I mean, you know, my division was, it felt huge to me, right? But it was actually tiny compared to the entire organization. It's 400,000 people at UnitedHealth Group. And you know, I mean, it is just an unbelievable juggernaut. I mean, it's like a small country, you know? So, what they do is they acquire companies all the time like something looks interesting, you know, you know, in an early stage startup, they'll say, okay, sure. You know, let's, let's invest 10 million in you and see how it goes. Like, it's such a trivial amount of money that, you know, they don't really care. And so, you know, that it's good and bad. Because, you know, on the good side, it offers enormous opportunity to people, right? I mean, because UnitedHealth Group can hire a ton of people to try and develop something that might or might not work or they can acquire a startup that already has it working, right? It's much cheaper. So, you know, it's great for that, but it's also, again, very much a juggernaut. Like once you're acquired, I mean, I went through this and then I had to help other groups through this. There's just like a process you need to go through and there are no exceptions and there's no like, but I wrote this whole thing in Java. I can't convert it all to something else right now. It doesn't matter. You just...
Vivek: ...have to do this way.
Rachel: Yeah. So, you know, so it's definitely a very different place, very different organization.
Vivek: Yeah. I, uh, Salesforce, a great place to work at. I really enjoyed my time there, but big company dynamic did get to me. And so I decided to, to bow out gracefully, or at least I think I did. So what excites you these days in the world of data, AI, and all this, LLM stuff is going on, you know, healthcare is definitely one of the industry verticals where there are a lot of applications. So uh, how do you think about all of that?
Rachel: I'm really excited about the state of AI right now. I'm really excited about how fast it's going, how fast it's moving, you know, all of the opportunities that, that it presents. One of the things that, you know, I had mentioned before was so, you know, one of my side projects while I was there was to build a system to identify X-rays. And they were, in fact, specifically dental X-rays. Like, you know, what's this an X-ray of? What kind of X-ray is it? Which teeth are they? You know, that kind of thing. So, you know, a year or so ago, I... this was like a notorious project. So two years ago I started on this project and it was this massive training set with like tons of data. Getting the data was horrible and difficult and all of that. And, you know, whenever, like earlier this year, after, you know, after the whole GPT thing so using GPT-4 for image analysis. I was able to give it like 30 examples of X-rays and then it flawlessly categorized all the rest. It was just like almost no code, almost no effort. And it's like, this is revolutionary. I mean, this is so unbelievable. And that combined with Copilot combined with, you know, some of the other amazing stuff. I mean, we built models to do fraud detection, to do, um, you know, to teach people how to do better sales, things like that that are just revolutionary. I mean, and it just keeps going faster. So I'm obviously very excited.
Vivek: Yeah. So last question for you. You're retired now, as you've told me. What does that mean?
Rachel: Um, what it really means is that, you know, I'm totally excited about what's going on in the AI world and I really needed to catch up on a lot of stuff. I mean, at this point it's going so fast that, you know, I really need to be reading every day and analyzing stuff every day. And plus, you know, I got a ton of quilting and knitting to do and all of that. So I feel like there's a bunch of stuff I need to do to wind down to maybe, you know, not need to make money anymore and to, you know, really take it easy. And it was really clear that the position I was in, though it was cool in a ton of ways, was just not good for being able to keep up with the stuff. It turned out to be a lot more, you know, day to day minutia than it was, you know, really broad thinking. And so, you know, it was sort of like I retired to step back, do some broad thinking, and then maybe see if there's somewhere else that I could contribute that might be more effective.
Vivek: There you go. So you're telling me there's a chance that Rachel is going to come back out of retirement.
Rachel: Well, I mean, if you're the one who's asking.
Vivek: Well, uh, rachel, thank you so much. This has been wonderful. Uh, twice in two weeks. What a privilege. Thanks again for joining us on the podcast and, uh, yeah, great to be in touch again and talking through all these things that are going on in the world. So, uh, thanks a lot.
Rachel: Thank you so much. It's been great talking and always totally fun. And I really appreciate the invitation.
Vivek: Of course. And so to our listeners, thank you for tuning in. You can sign up for our newsletter on superset.com and or www.closedsession.com. Thanks all. See you next time.