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Rachel Gollub on Engineering, Entrepreneurship & Leading Healthcare AI

December 20, 2023
Written By
December 20, 2023
Season 4 Episode 15
35:02
Written By

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.

Transcript

Welcome to The Closed Session. How to get paid in SiliconValley with your host Tom Chavez and Vivek Vaidya.

Vivek: Hello andwelcome back to season four of The Closed Session. This is Vivek Vaidya and forthis episode I'm by myself. But I have an amazing, amazing guest I'm about tointroduce. I worked with this person in my first job in Silicon Valley. Infact, I knew of her even before I started my job, because I read a lot of codewritten by her as I was learning. the Java programming language. So withoutfurther 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 anentrepreneur, she's an academician, academician? Is that... that's a word? Ithink. And, uh, yeah, I'm really excited to have Rachel on this podcast withus. Welcome, Rachel. So Rachel has a bachelor's degree in computer science andRussian literature from, uh, from Caltech. She also has studied militaryhistory later on in her life. And she worked at the digital library initiativeat Stanford as well, after a stunt... stint at Sun Microsystems. And then she'salso started a couple of companies, which we will talk about momentarily in thepodcast. So Rachel, great to have you here. How you been?

Rachel: Pretty good.How about you?

Vivek: I'm great. Itwas a good Thanksgiving break. I, uh, was quiet. I read a few books and cookeda little bit. But yeah, so, uh, let's, uh, let's get into this, uh, this talk,shall we?

Rachel: Cool.

Vivek: All right. Soyou 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, itwas really funny. My first job out of college was at a startup. And you knowhow startups go sometimes. Sometimes they're great. And sometimes they don'tlast very long. So, you know, after working there for less than six months, Ithink... they kind of took us all out on the patio and said, we have no moremoney, 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, includingJamie Zawinski, who I worked with there said you know, I want to go found thisbrowser company. You want to come with me? And I was like, you know, I, I don'tknow. I kind of want to do more challenging programming. Yes. Can you believe Isaid that? So, then he said, well, you know, my friend, Jeff Bezos is going upto Seattle to put together an online bookstore and that's probably more in yourarea. I'm like, that sounds great, but you know, my husband's in grad schooland I can't really move right now and it would be years. And, you know, so Ithink 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? AndI was like, yeah, sure. I mean, they're, they're in the area, you know, they'recool people. I'll try it. So I did. And that's how I ended up at SunMicrosystems. And then, you know, later in the Java group.

Vivek: Wow. So, whatwas it like being part of that team that developed Java? How was it workingwith James Gosling?

Rachel: Oh, it wasfantastic. The guy is so nice. It's, it's unreal. And everyone was incrediblyaccepting, you know, they're really excited to see me. I had ended up, youknow, I started in Sunsoft and then my friend Headley was just like, Hey, Ifound this really cool thing that a group is doing and, you know, we should gointerview there and see if they'll let us join them. So, you know, I went withhim and we interviewed and they hired us both and they really invited us to dosome of everything and it was super cool and I met really nice people and Ihave to say, you know, not every job I've had has been spectacular, but thatone really was.

Vivek: That'samazing. Like, and going back like what, 30 years now? That's uh... I can'tbelieve I just said that. But, uh,

Rachel: Yeah, I know,right?

Vivek: But no, itwas, it was quite amazing, right? Because it was the first time. I think it wasthe first time a company had decided to create a programming language fromscratch, right? Cause, uh, cause C, yeah, you know, it was Bell Labs and, andall of that, but that, that came out as a research effort, I think. But Javawas the first time a company decided we're going to create this programminglanguage. And, uh, look what it's become now, right? You must feel like such aproud, uh, proud parent almost. No?

Rachel: I totally doactually. 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 courseit's Java.

Vivek: Yeah.

Rachel: And you know,when I interview people, one of the things I frequently ask is, so what do youthink of Java?

Vivek: Yeah.

Rachel: You know, andthe people who know me are just like, oh, it's fantastic. Absolutely. But thenlike people who have never heard of me are just like, eh, you know, I don'tknow. I don't really like it. And it's like, really taking notes, you know,what don't you like?

Vivek: So do you holdthat against them?

Rachel: No, not atall. Because realistically there are so many good languages out there now, youknow, it's... it was the first of its kind in a lot of ways, but it's certainlynot the last.

Vivek: No, no, I, Itotally un... hear what you're saying, right. Cause as I was mentioning earlierin the introduction, I read a lot of source code written by you, the way ithappened was when I came to the US for a grad school, one of my professors wehad to do a bunch of courses and most of the courses that were being offeredthat quarter, I had already taken as part of my undergrad. So I went to myadvisor and said, hey, what should I do? And he said, well, you want to do anindependent study. I was like, what is that? He said, well, we agree on a topicand 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 mypace. He's like, yup, like, great. What are we learning? Says there's this newprogramming language out called Java. And so why don't you learn that? I'mlike, okay. And then it's buttered my bread for majority of my career likeyours, 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 otherlanguages come out, and you've, as you said, you're using them yourself. Howhas your approach to software engineering changed since those early days atJava to now?

Rachel: You know,realistically, it's changed constantly, like at every job, I've learnedsomething new. And I have a bunch of friends who are part of the lean startupmovement. So they've been, you know, really influential in how I look atstartups and how I look at software development in general. I think one of thebiggest changes as I've gotten older is a lot more appreciation for good DevOpsand infrastructure and testing and you know all the things that seemed sort ofby the way when I was much younger and now I'm just like these are criticalbecause you know you can't expect somebody while they're coding to think ofeverything. 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 gamechanger, you know, it's so nice to just tell it, like, you know, do this partof the code for me or remind me how to do that thing I forgot or whatever. Soyou 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 tocode every individual piece. So, you know, it's, the skills are different.

Vivek: Do you useCopilot?

Rachel: Yeah, Itotally 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 lookingfor something, I still end up typing it in Google. It's just... it's just forceof habit so far. But I've seen other people use it. And, uh, one of my, youknow, one of my things with tools like Copilot is that I think code should bereadable, right? And understandable by the average software engineer, right?And my worry with tools like Copilot is sometimes it ends up producing codethat is very cool, it does the job, but it's hard to understand by the averagesoftware engineer. Have you had that experience?

Rachel: You know, Ithink for the most part, I've used it for small things. So I've had thatoccasionally, but for the most part, I'm just like, okay, I can't remember howto, you know, write to a file in this particular way in this particularlanguage, 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 Ihave to go through and figure out what those are, you know, it's not like zeroeffort, but every time I use it, I learn something new or I'm reminded of howto do something that I'd forgotten and... You know, the way it's built intoVisual Studio, it's just so easy to use, you know, it's, I really think theydid a good job with that

Vivek: Yeah. So let'stalk about your founder and startup experience a little bit. You've worked atmany startups, right? DDoS mitigation, photo editing, gaming, wine, even thoughyou don't drink wine. We'll talk about that in a minute. Healthcare. So that'squite the spectrum. As you look back, tell us about the people that you workwith. What were some of the commonalities across the best teams at these, thesestartups? What were some of the things you didn't like about, about the teamsthat 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 essentialsactually, you mentioned military history, you know, I have a master's inmilitary history. So one of the things that I took away from that was the coreprinciples of maneuver warfare and how teams work together, because of coursethat'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 needto have mutual trust. You need to have experience, you know, people who haveexperience with each other and the kind of things you're doing. You have tohave common goals, you have to be shooting for the same things. And you have tofeel like what you're doing is going to make a difference. Like you can haveall the other things, but if your goal is to change the background of a pagefrom 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 experienceshave been the places where I had all of those things where, you know, everybodyworked together, everybody liked each other and, you know, we were going towardthe same thing. So when I started founding companies. That's what I builttoward, you know, if somebody, somebody could have been fantastic and a reallygood coder, but if they just couldn't, you know, they didn't have the samegoals or they didn't really, people didn't trust them, they just weren't a goodfit for the team. So I'd suggest they work somewhere else.

Vivek: Yeah. Nobrilliant 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 corrosivesometimes.

Rachel: Yeah.

Vivek: So you were aguest on our community call just about a week ago. And you, you said that aboutyour startups, that is some of them went nowhere, some of them became nicelifestyle businesses and some were successful. So tell us about the mostnegative experience. What were the lessons you, what were the lessons youlearned?

Rachel: That's agreat question. Okay. So the most negative experience was probably, um, so Iagreed to start a startup with a friend. And you know, he'll probably listen tothis, he's currently CEO of Treasury Prime. And so it was totally not hisfault. It was a negative experience. He's great like stellar. But what happenedwas we decided to found a startup together and we went out looking forcustomers, looking for funding, and we spent like six months just constantlygoing to people, trying to sell it, trying to get people involved, trying tofigure 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 toexplain to people. I mean, now it would be super easy. Like you need a way ofvisualizing your big data, right? Of course you do. There's a ton of stuff outthere now to do that. But we were like maybe five years early on that. And sopeople 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-founda 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. thatsort of solved that problem. But it was hard for both of us to give up thestartup that never even really got off the ground.

Vivek: Yeah.Sometimes you get too attached to these things, right? Because it's your babyand you don't, you know, in your head, in your mind, it's a great idea and thetime has come. And, uh, but sometimes the market is not just ready for it,right?

Rachel: Right.

Vivek: That happenedto us. I mean, and that's where, that's why I always say. And Tom and I bothsay this, like, luck plays such a huge part in getting you to where, where youget to, because arguably, Krux was the third iteration of the company that weended up building, not, not by us, but there were two other, there were otherpeople who had tried to do something similar twice before us, and they weremoderately successful, but the way in which we did things was only possiblebecause of when we started Krux. It was the perfect time, like computing wascoming 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, youknow, the negative experiences and the startups that didn't work well, to onesthat did and that were successful, what was different? What went differently onat the successful builds?

Rachel: Well, youknow, I kind of have to list that one as an exception, because we tried reallyhard, but it was the wrong time. But for the most part, you know, the biggestdifference has been the level of commitment. Like the first couple I started, Iwasn't totally committed to, and that turned out to be a problem, because ofcourse there are ups and downs, and when you hit those downs, sometimes you'rejust like, you know, maybe I'll give up on this, which is deadly if you'retrying to do a startup because there are always going to be ups and downs,right?

Vivek: Yep.

Rachel: And so thenonce I got the sense that I really did need to commit to these things, if I wasgoing to do them, then it was partners who maybe weren't totally committed. Andagain, this isn't Chris, right? Yeah. This is other partners that I'm thinkingof. But, you know, they were just like, well, I'm kind of doing this while I'mwaiting to do something else. And that's... that's terrible. So, you know, theones that really succeeded were the ones where I actually ended up not onlycommitting to it, but finding partners who were really willing to commit. Andwe were just going to like, you know, make this thing work no matter what.

Vivek: Yeah. Findingthe right partner is so important. That's why like, I'm so lucky to have beenworking 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 twofounders, we were talking to them last week and they were also togetherreflecting on the fact how important it is for the two of them to be togetherin 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 themorning, they needed some support. So they just called up their partner intheir company and pick up the phone and they ended up just talking to eachother and that kind of calm things down. So finding the right partner is soimportant. I completely agree.

Rachel: Yeah.

Vivek: As you nowreflect 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 stepfor you in your, whatever point you were in your life or is this somethingyou've always wanted to do?

Rachel: Honestly,I've always been sort of an entrepreneur. You know, when I was a kid, I used tocrochet dolls. I do a lot of crafting and I sent my poor brother out to sellthem house to house because I was just like, Hey, I'm making them, somebodyshould buy them.

Vivek: Right.

Rachel: And you know.So I'm kind of in that habit, and the first, the first company I actuallyfounded, 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 Ihad some disagreements with some of the folks there, totally friendlydisagreements about what should go into the language and what people should dothemselves. And so I ended up, you know, feeling like a lot of the librarieswere kind of incomplete. And remember this was way back, like now they're overcomplete, right? You can do everything 10 different ways. But at the time itwas a really bare bones language. And I thought there were some things peopleneeded. So I wrote a bunch of stuff and then I started selling it. And so, youknow, it was one of those things where, like, I'm in a unique position to knowhow to do this and to be able to solve this problem for people. And that wasthe 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 wellreally made a big difference.

Vivek: Yeah, that isso 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 factthat 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 yourfirst first startup. So, you know, and, and sometimes as you're going throughthis, sometimes you think things in the moment, things A, B and C are soimportant, right? But then when you reflect, you're like, nah, that wasn't thatimportant 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 areally good question. I think the biggest thing was well, you know, one of thethings that I discovered, this isn't, this isn't entirely an answer to thequestion, but one of the things that I did notice is that being completelydependent on making money fast is a terrible way to do a startup.

Vivek: Yes.

Rachel: And that wasone of the things that I learned early because I, set myself up in situationswhere I had a very short amount of time to make money. And so, you know, when Ididn't make money in that time, then, you know, that was a critical failure andI had to stop. And that's, you know, that's a terrible way to go into a startupbecause startups are generally slow. I mean, very few of them make a lot ofmoney. And in fact, another founder I worked with, his first startup, Like theysold it for, you know, millions after six months. So he went into his nextstartup, like, Oh, the same thing will happen. And you know, like five years inwhen he wasn't making money, he was, you know, what did I do wrong? Why is thisso terrible? It's such a failure. And I'm like, actually it was a terrificsuccess. 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 tothem about this concept of delayed gratification, you know, and, and if you'regoing to come work at super{set} building a company with us, you just have tosubscribe to delayed gratification. It is going to be a long build out, longdoesn't mean 25 years, right? But you're looking at the next 10 years of yourlife that's the expectation we set. Like you said, things don't, things nevergo as fast as you would, uh, want them to, or like them to, so, uh...

Rachel: Yeah, that'sa really good expectation to set too. I mean, that's a, that's a good way toprep people for what's coming.

Vivek: Yeah. And ifthings, if things go. faster and you, you get to your outcome or exits soonerthan 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 talkabout 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 anearly team? Do you look for pedigree? Or what qualities and mindsets do youlook for?

Rachel: It's notpedigree so much as I look for people who really enjoy solving challengingproblems, right? Also, like I said, people who get along really well with otherpeople who really understand collaboration. One of the things I've starteddoing, I want to say recently, but it was like 10 years ago, is, um, gettingeverybody who's going to be involved in working on something together withanyone I'm interviewing and just spending a couple hours together codingsomething together. Because what I care about isn't that they know how to lookthings up. What I care about is that they're comfortable asking questions,answering questions, talking with people, that there's some kind of connectionthey can make during that time. Because that's really, you know, that's a goodpredictor of success. So the people who, you know, don't want to ask anyquestions, 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 greatsomewhere else, but you know, in one of my teams, that's not going to workwell.

Vivek: Yeah, that'sso, that's so important and wise, right? Like I do the same thing cause maybe Iwas 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 forgetwhat question you had asked me but I, I wasn't able to get to the final answerand then when we talk later, you explained to me that, look, I wasn't lookingfor the right answer. I was looking for your process you went through and theconversation we had that you kind of led us to think through the solution tothe problem. And I've kind of embraced that throughout. Like you said, it'swhat questions you ask, are you able to talk through what you're doing? Are youable to stop and say, well, this works now and I've solved this problem, I'mgoing to do the next thing, so on and so forth. So, uh, yeah...

Rachel: Yeah, goodmemory, wow. That was the sort question, too. I remember asking you that one.

Vivek: It was thesort question, yes, I remember now. See, you remember, too.

Rachel: Oh yeah,totally.

Vivek: Anyway, sowe've reached this point now, Rachel, in our podcast where it's time for atotally unpaid for promotion. So we invite our guests to promote whatever theywant. Their favorite coffee shop, their favorite AI product, their favoritequilting, whatever you want. So the floor's yours. You can promote whatever youwant. The entity, the product you're promoting is not going to pay us. So thisis, so consider this a favor you're doing them.

Rachel: Okay. Thankyou. So I guess. I'm going to promote the San Jose Museum of Quilts andTextiles because this place is fantastic. And if you think of quilts as likesomething that, you know, your grandmother did or something, then you have noidea what quilts are like now. I mean, they are fabulous. There are art quiltsthat, you know, look completely realistic, that are completely abstract. Thereare art quilts that are selling for, you know, millions of dollars.

Vivek: Oh, wow.

Rachel: It's a hugefield now, and the, the Quilt Museum has a huge selection, like they havetextiles from the 1800s, they have modern art quilts, they have all sorts ofamazing 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 inthings like First Friday, um, which is, you know, a terrific program where abunch of places are open for free on the first Friday of every month. And ifyou happen to be in the area, you know, it's a fantastic place to visit.

Vivek: Well, thereyou have it for our listeners, the San Jose Museum of Quilts. Who knew quiltscould 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 nowlet'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, Imentioned 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 ofpeople started a, a company called BenefitsMe, where they were, you know, theywere going to try and do some fitness kind of benefits and stuff like that. Andtheir belief was that, you know, programmers are interchangeable. You can justlike hire a few people off the web to do some stuff and that's good for aproduct. So, you know, they learned they were wrong really fast and theydecided that they actually needed technical co-founders. So, you know, througha friend of a friend, they came and talked to me and said, we'd like to inviteyou 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 thisbecause, you know, this looks really promising. It's got people who have builtstartups before it's, you know, it's a really good idea. And what we weretrying to do, you know, one of the guys there, who is the CEO totally sucked mein with like, we're going to destroy group insurance. We're just going to getrid of insurance companies. We're going to make the world a better placebecause nobody has to buy health insurance. And so, you know, I was like, I'min, that sounds great. So, right. I mean, who wouldn't be? So, um, we ended updoing that. And, um, we started with six founders and, you know, after a fewyears, there were only two of us left, you know, which does tend to happen andwhen you have that many founders.

Vivek: I didn't knowthat six founders?

Rachel: Yeah. Yeah,it was crazy. Several of them made it like less than a year or just a year, butyou know, Brian and I just kind of went, went with it after that. And so whatwe 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 insurancebecause this is a new opportunity. So we're figuring out, you know, companieshad to pay a penalty if they didn't provide insurance for their employees, butwe could find a point where they could give a certain amount of money to theiremployees 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 theircompany. The company would pay less, you know, win all around. So we, we builta, you know, basically a Monte Carlo simulation of all of the, you know, giventheir 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 tocompanies and, you know, that didn't go as well as we wanted, but, you know, wehad really cool technology. So another company bought us and we, you know, butthey started, you know, they sort of had their own individual solution. So thenthey 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 westarted selling group insurance. And, um, so then all of us together werebought by UnitedHealth Group in 2019, actually. And in 2020 a new program cameout called ICRA that let you let companies actually buy individual insurancefor their employees without a penalty. So that's what we were looking for backthen.

Vivek: Right.

Rachel: So at thatpoint, 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 justat a different company, two acquisitions later.

Rachel: Right.Exactly. And you know, I feel like I should do the dance for getting acquiredtwice, 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 youguys want to get acquired or? The first time around second time around.

Rachel: The firsttime around, we definitely did because you know, we had been in existence for acouple of years and gotten whatever it was like five sales, you know, we atthat point, we were looking for an acqui-hire or something like that and weactually did better than that, which was great. And really a tribute to, youknow, our CEO who managed to get a better deal out of it. But then the secondtime, um, it was more our first funders were like, you know, Benefitter hasbeen going for eight years. We need an exit. Like we don't care what the exitis, you need to get out now. So at that point we were looking for anacquisition and we had, you know, luckily we had bids from a number ofdifferent companies and the UnitedHealth Group bid was actually the one thatlooked the most promising for everybody. So we ended up going with that one.

Vivek: And then youhad a very interesting kind of transition in terms of your role, like you, Imean, you were CTO at Benefitter and then Optum, but then the size of the teamsyou were managing were relatively speaking small, right? And then you were atUnitedHealth 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 forthat entire organization, you know, it was like, stop doing Benefitter come andbe my CTO. I was like, And I'm like, sure, sounds great, you know, I can teachsome people how to code and do all that stuff. I just did not realize the scaleof the organization that she managed. You know, I was like, Oh, you know, maybea 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 atall 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. Butthere were still people who just hadn't heard my name, you know, by the time Ieven left. So, I mean, just the scale was ridiculous.

Vivek: Yeah, no, Iremember when I, when Krux got acquired by Salesforce, my team at Krux was 85people all in and then I go to Salesforce and they, they thought I was capableenough. So they gave me the option of running all of engineering for Salesforcemarketing cloud and I was like, sure, I'll do that. And overnight I went frommanaging a team of 85 people to managing a team of a thousand people. And, uh,

Rachel: Yeah.

Vivek: And that was abig change for me. And the teams were, this was actually way before thepandemic. 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 inCanada in Newfoundland, Canada, and then, uh, London. So, yeah. So if you askPallavi, my wife, she'll tell you that. So there were, there were months when Iwas working harder at Salesforce than I was at Krux because of all the travelthat I had to do. Yeah. So, but you also, you, you know, in your role as CTO atOptum, you were working on various AI projects as well, right? So, as you thinkabout 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 healthtech?

Rachel: Yeah, so it'sactually 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 aboutretiring and what ended up keeping me there is the opportunity to train AI onincredible amounts of data because you know, UnitedHealth Group is one of thebiggest 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 theUnitedHealth Group plans changed all the time and employer and individual isone section of that, right? But we still had access to, you know, tens ofmillions of health records and, you know, pharmacy records and everything. Andthat was unbelievable. So, you know, that gave us opportunities to docorrelations that we couldn't have otherwise done anywhere else. And so thatwas, you know, that was a definite draw. It's also, you know, the rate ofacquisition for a company like UnitedHealth Group, I mean, you know, mydivision was, it felt huge to me, right? But it was actually tiny compared tothe entire organization. It's 400,000 people at UnitedHealth Group. And youknow, I mean, it is just an unbelievable juggernaut. I mean, it's like a smallcountry, you know? So, what they do is they acquire companies all the time likesomething 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 andsee how it goes. Like, it's such a trivial amount of money that, you know, theydon'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 developsomething that might or might not work or they can acquire a startup thatalready has it working, right? It's much cheaper. So, you know, it's great forthat, 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 exceptionsand there's no like, but I wrote this whole thing in Java. I can't convert itall to something else right now. It doesn't matter. You just...

Vivek: ...have to dothis way.

Rachel: Yeah. So, youknow, 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 bigcompany dynamic did get to me. And so I decided to, to bow out gracefully, orat 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 oneof the industry verticals where there are a lot of applications. So uh, how doyou think about all of that?

Rachel: I'm reallyexcited about the state of AI right now. I'm really excited about how fast it'sgoing, how fast it's moving, you know, all of the opportunities that, that itpresents. One of the things that, you know, I had mentioned before was so, youknow, one of my side projects while I was there was to build a system toidentify X-rays. And they were, in fact, specifically dental X-rays. Like, youknow, 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 waslike a notorious project. So two years ago I started on this project and it wasthis massive training set with like tons of data. Getting the data was horribleand 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. Iwas able to give it like 30 examples of X-rays and then it flawlesslycategorized 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 thatcombined 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 teachpeople how to do better sales, things like that that are just revolutionary. Imean, and it just keeps going faster. So I'm obviously very excited.

Vivek: Yeah. So lastquestion for you. You're retired now, as you've told me. What does that mean?

Rachel: Um, what itreally means is that, you know, I'm totally excited about what's going on inthe AI world and I really needed to catch up on a lot of stuff. I mean, at thispoint it's going so fast that, you know, I really need to be reading every dayand analyzing stuff every day. And plus, you know, I got a ton of quilting andknitting to do and all of that. So I feel like there's a bunch of stuff I needto 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 wasin, though it was cool in a ton of ways, was just not good for being able tokeep up with the stuff. It turned out to be a lot more, you know, day to dayminutia than it was, you know, really broad thinking. And so, you know, it wassort of like I retired to step back, do some broad thinking, and then maybe seeif 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 ofretirement.

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 goingon in the world. So, uh, thanks a lot.

Rachel: Thank you somuch. It's been great talking and always totally fun. And I really appreciatethe invitation.

Vivek: Of course. Andso to our listeners, thank you for tuning in. You can sign up for ournewsletter on superset.com and or www.closedsession.com. Thanks all. See younext time.

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Marketing in the Age of AI with Rex Briggs

How is AI steering the future of marketing strategy? With the convergence of AI and marketing tactics, Rex Briggs paints a compelling picture of what's possible: AI agents that revolutionize user interactions, and generative techniques that craft persuasive content. Drawing from his deep expertise in marketing measurement, Rex joins Tom Chavez and Vivek Vaidya to explore the cutting-edge of AI-driven marketing strategies. Listen for insights on harnessing AI's potential in modern marketing.

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Tom Chavez in Huffpost Personal for Hispanic Heritage Month

Writing in the Huffington Post: "My Mom Sent Me And My 4 Siblings To Harvard. Here's The 1 Thing I Tell People About Success."

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Developer tools that are worth their while: KEDA and Boundary in action

Running cloud platforms efficiently while keeping them secure can be challenging. In this blog post, learn how two of super{set}’s portfolio companies, MarkovML and Kapstan, are leveraging tools like KEDA for event-driven scale and Boundary for access management to remove friction for developers. Get insights into real-world use cases about optimizing resource usage and security without compromising productivity.

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Watch: Sandeep Bhandari Fireside Chat

Sandeep Bhandari, Former Chief Strategy Officer and Chief Risk Officer at buy now, pay later (BNPL) company Affirm, joins Vivek Vaidya, Founding General Partner of super{set}, in conversation.

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Spotlight Series: Andrew Marshak, Co-founder of Headlamp Health

The {Closed} Session Spotlight Series showcases a different co-founder from the super{set} portfolio every episode. Up now: Andrew Marshak is Co-founder and Head of Product at Headlamp Health (Headlamp.com), a healthtech company bringing greater precision to mental health care.

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Philosophy, Data, and AI Ethics with NYT Best-selling Author + Data Scientist Seth Stephens-Davidowitz

From unpacking Google search patterns to understanding the philosophical underpinnings of big data, Seth Stephens-Davidowitz offers a unique lens. As the NYT Best-selling author of “Everybody Lies” and a renowned data scientist, he delves into the ways data mirrors societal nuances and the vast implications for tech and its intertwining with everyday life.

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Forbes: 5 Startup Studio Misconceptions

It's still early for the startup studio asset class - and we hear misconceptions about the studio model every day, ranging from the basic confusion of accelerators versus studios to downright incorrect assumptions on our deep commitment to the build-out of every company. Read Tom Chavez' latest in Forbes.

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Ringside Tales from Serial Startup Champion Omar Tawakol

Like Rocky Balboa and Apollo Creed, the fiercest competitors can sometimes become friends. Omar Tawakol is a prime example. As the founder and CEO of BlueKai, he went head-to-head with Tom, Vivek, and the 'Krux mafia' for dominance in the Data Management Platform arena. A serial entrepreneur with roots in New York and Egypt, Omar eventually steered BlueKai to a successful acquisition by Oracle before creating Voicea, which Cisco acquired. Today, he's pioneering a new venture called Rembrand (rembrand.com), which innovates in product placement through generative fusion AI.

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Spotlight Series: Lindsey Meyl, Co-founder of RevAmp

The {Closed} Session Spotlight Series showcases a different co-founder from the super{set} portfolio in every episode. Today's guest is Lindsey Meyl, Co-founder at RevAmp (rev-amp.ai), a "Datadog for RevOps" platform that offers observability across the revenue engine, monitoring performance, flagging when something is amiss, and determining the root cause of how to fix it.

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Why Proprietary Data Is the Linchpin of AI Disruption

Read Vivek Vaidya's latest in CDO Magazine and learn why in this new AI landscape, those who harness the potential of proprietary data and foster a culture of collaboration will lead the way—those who don't risk obsolescence.

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MedCity News: It’s Time for the Tech Revolution to Come to Mental Health Diagnoses

Headlamp Health co-founder Andrew Marshak writes in the MedCity News that "We need to take inspiration from the progress in oncology over the last few decades and challenge ourselves to adapt its successful playbook to mental illness. It’s time for precision psychiatry."

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What Consumers Think of AI and Their Privacy

Everyone’s talking about AI - so The Ethical Tech Project decided to listen. Joining forces with programmatic privacy and data+AI governance platform Ketch, The Ethical Tech Project surveyed a representative sample of 2,500 U.S. consumers and asked them about AI, the companies leveraging AI, and their sentiment and expectations around AI and privacy. On the latest episode of The {Closed} Session, get an inside look at the survey results in a deep-dive conversation with the team at The Ethical Tech Project.

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Why the AI Revolution Will Be Data-Centric

Pankaj Rajan, co-founder of MarkovML, joins super{set} Chief Commercial Officer Jon Suarez-Davis (jsd) to discuss the role of data in gaining a competitive advantage in the AI revolution. Learn the difference between optimizing models and optimizing data in machine learning applications, and why effective collaboration will make or break the next-gen AI applications being created in businesses.

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Why the AI Revolution Will Be Data-Centric

Pankaj Rajan, co-founder of MarkovML, joins super{set} Chief Commercial Officer Jon Suarez-Davis (jsd) to discuss the role of data in gaining a competitive advantage in the AI revolution. Learn the difference between optimizing models and optimizing data in machine learning applications, and why effective collaboration will make or break the next-gen AI applications being created in businesses.

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CalMatters: Why visa reforms benefit not just California’s tech sector but the economy overall

Vivek Vaidya writes that America needs more H-1B workers. Common sense reforms to the program will even the playing field for startups, not Big Tech, to bring innovative talent to American's shores.

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Why CTOs Should Care About Gross Margins, Cost-to-Serve, and Product Management

Why should a tech exec care about profit and loss? Aren’t our jobs to make the product great, and someone else can figure out how to make the numbers add up? That was my attitude for a long time until I finally appreciated the significance of gross margins for SaaS businesses during the early part of my tenure as the CTO of Krux.

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How Boombox Nurtures Customer Collaboration for Success

In a conversation with boombox's co-founder India Lossman, the discussion pivots to the art of fostering customer collaboration in music creation. Lossman unveils how artist-driven feedback shapes boombox's innovative platform, with a glimpse into AI's empowering potential. Understand the synergy between technology and user insights as they redefine the independent music landscape.

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Tom Chavez in Huffpost Personal for Hispanic Heritage Month

Writing in the Huffington Post: "My Mom Sent Me And My 4 Siblings To Harvard. Here's The 1 Thing I Tell People About Success."

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Tech Crunch: Answering AI’s biggest questions requires an interdisciplinary approach

Tom Chavez, writing in TechCrunch, calls for new approaches to the problems of Ethical AI: "We have to build a more responsible future where companies are trusted stewards of people’s data and where AI-driven innovation is synonymous with good. In the past, legal teams carried the water on issues like privacy, but the brightest among them recognize they can’t solve problems of ethical data use in the age of AI by themselves."

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Former Salesforce SVP of Marketing Strategy and Innovation Jon Suarez-Davis “JSD” Appointed Chief Commercial Officer at super{set}

The Move Accelerates the Rapidly Growing Startup Studio’s Mission to Lead the Next Generation of AI and Data-Driven Market Innovation and Success

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Good Ideas, Good Luck

Coming up with new company ideas is easy: we take the day off, go to the park, and let the thoughts arrive like butterflies. Maybe we grab a coconut from that guy for a little buzz. While this describes a pleasant day in San Francisco, it couldn’t be further from the truth of what we do at super{set}. If only we could pull great ideas out of thin air. Unfortunately, it just doesn’t work that way.

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7 Ways to Turn an Internship Into a Job at a Startup

Chris Fellowes, super{set} interned turned full time employee at super{set} portfolio company Kapstan, gives his 7 recommendations for how to turn an internship into a job at a startup.

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super{set}’s Spectrum Detoxifies The Online Space

We are living in a time of extraordinary concern about the negative consequences of online platforms and social media. We worry about the damage interactive technologies cause to society; about the impact to our mental health; and about the way that these platforms and their practices play to our most destructive impulses. Too often, the experiences we have online serve only to polarize, divide, and amplify the worst of human nature.

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Why I'm Co-founding @ super{set}

Pankaj Rajan, co-founder at MarkovML, describes his Big Tech and startup experience and his journey to starting a company at super{set}.

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From Suitcases to Startups: Why Immigrants Innovate

How are immigrants like entrepreneurs? Peter Wang of Ketch arrived in the U.S. at age 7 with two suitcases and a box. Read his story in the latest "Pass The Mic."

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Why I'm Joining super{set} as Chief Commercial Officer

Announcing Jon Suarez-Davis (jsd) as super{set}’s Chief Commercial Officer: jsd tells us in his own words why he's joining super{set}

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Four Tips for a Distributed Workforce

This month we pass the mic to Sagar Gaur, Software Engineer at super{set} MLOps company MarkovML, who shares with us his tips for working within a global startup with teams in San Francisco and Bengaluru, India

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Forbes: 5 Startup Studio Misconceptions

It's still early for the startup studio asset class - and we hear misconceptions about the studio model every day, ranging from the basic confusion of accelerators versus studios to downright incorrect assumptions on our deep commitment to the build-out of every company. Read Tom Chavez' latest in Forbes.

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boombox.io Raises $7M to Build Out Creator Platform for Music Makers

super{set} startup studio portfolio company’s seed funding round was led by Forerunner Ventures with participation from Ulu Ventures Raise will enable boombox.io to accelerate product development on the way to becoming the winning creator platform for musicians globally

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The Four Types of Startup Opportunities

In our last post, we discussed how data is the new general-purpose technology and that is why at super{set} we form data-driven companies from scratch. But new technologies are a promise, not a sudden phase change.

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Why I Left Google To Co-found with super{set}

Gal Vered of Checksum explains his rationale for leaving Google to co-found a super{set} company.

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Pivots and Possibilities

Discover how lessons from law enforcement shape a thriving tech career. Ketch Sr. Business Development Representative Brenda Flores shares a bold career pivot in our latest "Pass the Mic" story.

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Lessons from the Startup Circus

super{set} Technical Lead and resident front-end engineering expert Sagar Jhobalia recaps lessons from participating in multiple product and team build-outs in our startup studio. Based on a decade of experience, Sagar emphasizes the importance of assembling the right engineering team, setting expectations, and strategically planning MVPs for early wins in the fast-paced startup environment.

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Data Eats the World

The wheel. Electricity. The automobile. These are technologies that had a disproportionate impact on the merits of their first practical use-case; but beyond that, because they enabled so much in terms of subsequent innovation, economic historians call them “general-purpose technologies” or GPTs...

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From Watsonville To The Moon

This post was written by Habu software engineer, Martín Vargas-Vega, as part of our new #PassTheMic series.

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VCs Write Investment Memos, We Write Solution Memos

When a VC decides to invest in a company, they write up a document called the “Investment Memo” to convince their partners that the decision is sound. This document is a thorough analysis of the startup...

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Why Proprietary Data Is the Linchpin of AI Disruption

Read Vivek Vaidya's latest in CDO Magazine and learn why in this new AI landscape, those who harness the potential of proprietary data and foster a culture of collaboration will lead the way—those who don't risk obsolescence.

read more

We don’t critique, we found and build.

The super{set} studio model for early-stage venture It is still early days for the startup studio model. We know this because at super{set} we still get questions from experienced operators and investors. One investor that we’ve known for years recently asked us: “you have a fund — aren’t you just a venture capital firm with a different label?”

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Podcast: Tom Chavez on How AI Startups Can Show Us What’s Next in Marketing

Tom Chavez joins the "Decoding AI for Marketing" podcast published by MMA Global and hosted by well-respected international marketing & AI experts Greg Stuart (CEO, Author, Investor, Speaker) and Rex Briggs (Founder/CEO, Inventor, Author, Speaker).

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The Era of Easy $ Is Over

The era of easy money - or at least, easy returns for VCs - is over. Tom Chavez is calling for VCs to show up in-person at August board meetings, get off the sidelines, and start adding real value and hands-on support for founders.

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The Product Mindset for Engineers

Ever find yourself scratching your head about product management decisions? Join India Lossman, co-founder of boombox.io, as she unpacks the product mindset for engineers. Unravel the art of synergy between PMs and engineers and delve into strategies to enhance collaboration and craft products that users will adore.

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Founder and Father: A Balancing Act

Making It Work With Young Kids & Young Companies

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Diamonds in the Rough

Obsessive intensity. Pack animal nature. Homegrown hero vibes. Unyielding grit. A chip on the shoulder. That's who we look for to join exceptional teams.

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The Balancing Act For Women in Tech

This post was written by Ketch Sales Director, Sheridan Rice, as part of our #PassTheMic series.

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The RevOps Bowtie Data Problem

Go-to-market has entered a new operating environment. Enter: RevOps. We dig into the next solution space for super{set}, analyzing the paradigm shift in GTM and the data challenges a new class of company must solve.

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Why Head of Product is Our First Co-Founder

At super{set}, we stand side-by-side and pick up the shovel with our co-founders. Our first outside co-founder at a super{set} company is usually a Head of Product. Let’s unpack each portion of that title....

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Building Fast, Scaling Globally

Harshil Vyas joined the super{set} Hive (i.e., portfolio companies community) in March 2023 as Co-Founder of Kapstan and employee number one in India. We jumped on a Zoom recently to talk about accelerated timelines, globally distributed workforces, and what is unique about the super{set} model.

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Forbes: Why A Collaborative Approach Trumps "Lone Genius" In Company-Building

Off the heels of super{set}'s first exit - the acquisition of data collaboration company Habu by LiveRamp for $200 Million - Tom Chavez writes how the super{set} approach to collaboration in company building leads to successful outcomes.

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How Engineers Should Talk to Customers with Empathy

Do you get an uneasy feeling anytime you get added to a customer call? Do you ever struggle to respond to a frustrated customer? Peter Wang, Product lead at Ketch, discusses how customer feedback can help drive product development, and how engineers can use customer insights to create better products. Learn best practices for collecting and interpreting customer feedback.

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super{set} Celebrates First Exit: LiveRamp to Acquire Data Collaboration Software Startup Habu for $200M

LiveRamp Enters Into Definitive Agreement to Acquire Habu, Reinforcing super{set}'s Unique Company Building Model of Founding, Funding, and Scaling Data+AI Businesses

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The Information: The People OpenAI Should Consider for Its New Board

Tom Chavez writes in The Information that "OpenAI’s board needs a data ethicist, a philosopher of mind, a neuroscientist, a computer scientist with interdisciplinary expertise and a political strategist."

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High-Velocity Personal Growth

What's the price you put on personal growth? In his most recent note to founders, super{set} Founding General Partner Vivek Vaidya outlines 7 points of advice for startup interviews and negotiations. Vivek explains his compensation philosophy and the balance between cash and the investment in personal and career growth a startup can bring. Here’s the mindset you need to reach your zenith at a startup.

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Building Tech on a Moving Regulatory Target

In an interview with Ketch co-founder Max Anderson, the focus is on data privacy laws and AI's role. Anderson discusses the global privacy landscape, highlighting Ketch's approach to helping businesses navigate regulations. The conversation also emphasizes data dignity and Ketch's unique role in the AI revolution.

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From Chords, to Code, to Chords Again: The Story Behind Boombox.io

super{set} founding general partner Tom Chavez wasn’t always set on a life of engineering and entrepreneurship – music was his first love. For a time, he was determined to make a career out of it. With boombox.io, Tom has combined the best of both worlds into a product that inspires and delights both the engineer and the musician.

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How To Avoid Observability MELTdown

o11y - What is it? Why is it important? What are the tools you need? More importantly - how can you adopt an observability mindset? Habu Software Architect Siddharth Sharma reports from his session at super{summit} 2022.

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Forbes: Why The Biden-Xi Talks Should Put A Microscope On San Francisco

The prettifying and securing of downtown San Francisco, where super{set} is headquartered, should be the norm - not just for special state visits from the world's dictators. Here are 3 things the city of San Francisco should be doing all year round to make the city better to live, work, and invest in. Read Tom Chavez' latest in Forbes.

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Not Just On Veterans Day

This post was written by Ketch Developer Advocate, Ryan Overton, as part of our #PassTheMic series.

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Why Headlamp Health is Bringing Precision to Mental Health

Co-founder of Headlamp Health, Andrew Marshak, describes the frustratingly ambiguous state of mental health diagnoses - and the path forward for making mental health a precision science.

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Jamming with Habu’s Matt Kilmartin on Partnership Strategy

Discover how Habu, a trailblazer in data clean room technology, utilizes strategic partnerships with giants like Microsoft Azure, Google Cloud, and AWS to expand its market reach and foster the potential of an emerging category. Learn from CEO Matt Kilmartin's insights on how collaboration is the secret sauce that brings innovation to life.

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Q&A with Accel Founder Arthur Patterson

Arthur Patterson, founder of venture capital firm Accel, sits down for a fireside chat with super{set} founding partner Tom Chavez as part of our biweekly super{set} Community Call. Arthur and Tom cover venture investing, company-building, and even some personal stories from their history together.

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Too Dumb to Quit

The decision to start a company – or to join an early stage one – is an act of the gut. On good days, I see it as a quasi-spiritual commitment. On bad days, I see it as sheer irrationality. Whichever it is, you’ll be happier if you acknowledge and calmly accept the lunacy of it all...

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ActiveFence Acquires super{set} Company Spectrum Labs

ActiveFence, the leading technology solution for Trust and Safety intelligence, management and content moderation, today announced its successful acquisition of Spectrum Labs, a pioneer in text-based Contextual AI Content Moderation.

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Understanding The AI “Alignment Problem”

Vivek Vaidya recaps his conversation with AI researcher and author of "The Alignment Problem" Brian Christian at the 2023 super{summit}.

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Hold Fast: Game-Changing Wisdom from Seamus Blackley

Creator of the XBox and serial entrepreneur Seamus Blackley joined Tom Chavez on stage at the 2023 super{summit} in New Orleans, Louisiana, for a free-ranging conversation covering the intersection of creativity and technology, recovering back from setbacks to reach new heights, and a pragmatic reflection on the role of fear and regret in entrepreneurship.

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The super{set} Entrepreneurial Guild

Has someone looking to make a key hire ever told you that they are after “coachability”? Take a look at the Google ngram for “coachability” — off like a rocket ship since the Dot Com bubble, and it’s not even a real word! Coaching is everywhere in Silicon Valley...

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Redefining Customer Experience in Data-Driven Tech Startups

Ted Flanagan, Chief Customer Officer at super{set}-founded Habu, sat down with Jon Suarez-Davis (jsd) to provide insights into how Habu's strategies in customer experience set it apart in the data collaboration market. Learn how customer experience strategies helped Habu land a $200 million after being acquired by LiveRamp in January 2024.

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Infrastructure Headaches - Where’s the Tylenol?

Head of Infrastructure at Ketch, and Kapstan Advisor, Anton Winter explains a few of the infrastructure and DevOps headaches he encounters every day.

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The Information: "TikTok Is Not the Enemy"

Tom writes a nuanced take on the TikTok controversy and outlines ethical data principles that will restore people’s sense of trust and offer them true control over how and when they grant permission for use of their data.

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When Inference Meets Engineering

Othmane Rifki, Principal Applied Scientist at super{set} company Spectrum Labs, reports from the session he led at super{summit} 2022: "When Inference Meets Engineering." Using super{set} companies as examples, Othmane reveals the 3 ways that data science can benefit from engineering workflows to deliver business value.

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Horizontal Scaling at super{summit}

Vivek gives us the rundown on what the hive is buzzing about after super{summit} 2023: how to 'horizontally scale' yourself.

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Spectrum Co-founders Launch Nurdle AI

Justin Davis and Josh Newman, Co-founders of Spectrum Labs (acquired) launch Nurdle to get AI into production faster, cheaper & easier.

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MedCity News: It’s Time for the Tech Revolution to Come to Mental Health Diagnoses

Headlamp Health co-founder Andrew Marshak writes in the MedCity News that "We need to take inspiration from the progress in oncology over the last few decades and challenge ourselves to adapt its successful playbook to mental illness. It’s time for precision psychiatry."

read more

Developer tools that are worth their while: KEDA and Boundary in action

Running cloud platforms efficiently while keeping them secure can be challenging. In this blog post, learn how two of super{set}’s portfolio companies, MarkovML and Kapstan, are leveraging tools like KEDA for event-driven scale and Boundary for access management to remove friction for developers. Get insights into real-world use cases about optimizing resource usage and security without compromising productivity.

read more

Watch: Sandeep Bhandari Fireside Chat

Sandeep Bhandari, Former Chief Strategy Officer and Chief Risk Officer at buy now, pay later (BNPL) company Affirm, joins Vivek Vaidya, Founding General Partner of super{set}, in conversation.

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How I Learned to Stop Optimizing and Love the Startup Ride

Reflections after a summer as an engineering intern at super{set}

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Overheard @ super{summit}

Vivek Vaidya's takeaways from the inaugural super{summit}

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An Intro to Product-Led Growth from MarkovML

Want to grow your product organically? This blog post breaks down understanding costs, setting up starter plans, and pricing premium features using MarkovML as an example. Learn how to engage new users and encourage upgrades, enhancing user experience and fueling growth through actionable insights.

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Detecting Software Bugs with AI

Gal Vered is co-founder and Head of Product at Checksum (checksum.ai), an innovative company that provides end-to-end test automation that leverages AI to test every corner of an app. He sat down with Jon Suarez-Davis (jsd) to discuss the exciting problem that Checksum is solving with AI and what Gal likes best about working in super{set}'s startup studio model.

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Navigating the Startup Journey from Launch to Finish Line

Are you a launcher, or a finisher? The balance of conviction, a guiding vision, and the right team to execute it all make the difference between entrepreneurial success and failure. Tom Chavez delves into his journey as a first-time CEO and the invaluable guidance he received from a key mentor.

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Silicon Valley’s Greatest Untapped Resource: Moms

This post was written by MarkovML Co-Founder, Lindsey Meyl, as part of our #PassTheMic series.

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