Conversations with members of the Harvard and Radcliffe Class of 1992.
Hosted by Will Bachman.

Episode: 92

Mark Jacobstein, Accidental Entrepreneur

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Show notes

Mark Jacobstein resides in Stanford, California with his wife, two children, and his mother in law. Mark’s career has primarily focused on entrepreneurial technology, primarily in health tech, biotech, molecular diagnostics, and digital health arenas. After Cambridge, he worked with Scott Murphy, a close friend and business partner. He moved to California in 2003 to start a technology company and has been there ever since. He lives on the Stanford campus, which allows his children to grow up on a college campus.


Founding a Fantasy Sports Business

Mark shares his journey from writing software for Mike Bloomberg in the early 90s to inventing the first online fantasy sports business [Small World] in 1994. He and his partner, Scott, initially struggled with starting a technology company due to their naivety and lack of experience in the tech startup ecosystem. However, they eventually built the first online fantasy sports business, which was one of the biggest consumer sites in the world at the time. In 1995, they spun out a web consultancy to solve various problems for corporate clients, building stateful and database-driven websites. They later built corporate websites for companies like Xerox and consulting for McKinsey on the internet’s future. The business was sold to i-EXL in 1998. One common thread Mark has seen over the past 30 years is looking for systemic paradigm shifting changes in technology. Mark’s career highlights the importance of adapting to new technologies and finding the most effective way to grow a business.


Entrepreneurship in Machine Learning and AI

Mark’s last two companies and new venture studio focuses on machine learning and AI. He discusses his journey as an entrepreneur and the transition from a hobby to a business. He emphasizes the importance of looking for latent demand in businesses, he also emphasizes the importance of not engaging in gambling and making ethical choices in business decisions. His first experience as an entrepreneur was when he and his roommate Scott started hiring employees. They faced challenges like crash and the need to lay off employees.


Startup Business Mistakes 

Mark discusses the mistakes made by his company in structure and decision-making processes. He believes that they were naive and didn’t put enough thought into the process of disagreements, which caused friction and strained relationships. He also mentions that the biggest mistakes they made were sins of omission. They were too early to realize the monstrous opportunities that nobody was taking advantage of. One example is hiring Matt Funk, a summer intern who later became a hedge fund manager. He suggested they buy domain names, but Mark argued that this was unethical. Another example is building the first Business to Business Exchange (B2B) website,, in 1996. This was an effort to make the textiles business more efficient. However, Mark argues that they missed out on the commercial implications of the internet and how they could have used their technology to service other industries.


Silicon Valley and the Tech Landscape in the 2000s

Mark shares his experiences in the 2000s, particularly in the mobile business industry. He sold his fantasy sports business, Small World Sports, to Paul Allen, who bought Sporting News, an interactive TV channel. After a burnout at Sporting News. Mark met Trip Hawkins, founder of Electronic Arts and 3DO. Mark was offered a position as co-founder and president of a mobile phone company. He was invited to Silicon Valley to meet with Sequoia and Kleiner Perkins. He was mentored by Trip and his experience in Silicon Valley was a pivotal moment in his life. He shares his experiences in the tech industry, starting with his time at Digital Chocolate and then moving on to venture capital firm Sequoia. He was introduced to Sam Altman, a young wunderkind, and worked with him to build a company called Looped, which was later sold to Qualcomm. 


Working in Health Technologies

After leaving Digital Chocolate, he decided to make a career shift into health tech. He enjoyed his work in fantasy sports but felt that nothing had changed the world in a profoundly important way. He eventually joined Guardant Health, a molecular diagnostic company that applied machine learning to big omics and developed cancer detection using blood draws. He was drawn to the intellectual challenge of working on circulating tumor DNA for early detection of cancer. Mark worked with Immunai, a company that uses single cell genomics and machine learning to improve immunomodulatory therapeutics. He appreciates the importance of the immune system’s complexity and the work in the field. He recently founded Jiminy Health, a company that aims to address care gaps in mental health care through mobile and MLMs.  


The Importance of Authentic Leadership 

Mark has learned the importance of authenticity in running a company that is non-obvious or counterintuitive. He believes that authenticity is crucial in leadership and having a compelling vision. As a CEO, he focuses on making that vision clear and helping organizations untangle their knots to pull towards a common goal. He has learned from Sam’s outrageous ambition and his ability to build companies that start with seemingly outrageous ideas. He applies these lessons to his own work, thinking about what different people would do in different situations as long as it aligns with his values and aligns with his values. He compares running a lab to running a business, which involves raising money, hiring people, meeting deadlines, and missing milestones


Influential Harvard Professors and Courses 

Mark discusses his experiences at Harvard, focusing on courses and professors that resonate with him. He mentions Harry Lewis, who was a computer scientist, and his career in tech. He emphasizes the importance of having a vision and articulating it to attract customers and recruit a team. He also highlights the importance of social reflection classes like Robert Coles, which taught him how telling a story can change the world and create an ethos that cares about the world. Mark’s mental health startup, Jiminy Health, aims to make scalable mental health services for millions of people. He believes that being raised in a liberal, progressive family still helps his businesses make the world a better place.



02:59 Entrepreneurship, technology, and business success

08:46 Entrepreneurship and technology trends 

10:36 Entrepreneurship, business decisions, and growth

16:58 Missed opportunities in tech and entrepreneurship

23:34 Entrepreneurship, leadership, and the video game industry

27:03 Career shift from tech to healthcare with valuable insights

32:55 Entrepreneurship, leadership, and management style

38:02 Leadership, authenticity, and lessons learned from mentors

41:29 Relying on a spouse as a counselor in healthcare

45:58 Entrepreneurship, technology, and mental health




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Mark Jacobstein

Will Bachman, Mark Jacobstein


Will Bachman  00:02

Hello, and welcome to the 90 T report conversations with members of the Harvard and Radcliffe class of 1992. I’m your host will Bachman. And I’m excited to be here today with Mark Jacobstein. Mark, welcome to the show.


Mark Jacobstein  00:15

Thanks so much. Well, I’m really excited to be here.


Will Bachman  00:17

So Mark, tell me about your journey since graduating from Harvard.


Mark Jacobstein  00:22

It’s quite a question. It has been 32 years. Man, I suppose the two things that come to mind immediately to talk about are one my amazing family. I live out here in Stanford, California with my wife and two kids and my mother-in-law. And my kids are only eight and two, which is I think, somewhat notable is most of our class or they’re now either empty nesters or about to be empty nesters. Some have actually become grandparents, my wife and I met a little later in life and then had a long journey to have our kids. And so I’m going to be 70 when my youngest graduates from high school, they are a joy, and happy to talk about them all day. They keep me young for sure. And give me a reason for trying to stay sort of California fit so that 70 really can be the new 50. The other thing that immediately comes to mind versus talk about my career, which has been almost exclusively in sort of entrepreneurial technology work. First 20 years or so, sort of pure tech in the last 10 years, largely in health tech, including both sort of biotech and molecular diagnostics and a variety of other digital health arenas. But you know, it’s been certainly an interesting journey. Me, I left Cambridge, almost immediately after graduation and went to New York for 10 years, worked very closely with one of our classmates who Scott Murphy was my business partner for eight or nine years and remains one of my closest friends and favorite people in the world. Despite the fact that we’re now 3000 miles apart. And and then I moved out to California in 2003, to start a yet another technology company, and I’ve been out here ever since. I love it out here. It’s great for what we do. And my wife and I actually live on the Stanford campus. So she has a seven minute bike ride to her lab, which is wonderful, and our kids get to grow up on a college campus. But I admit I miss, I miss the East Coast, I actually specifically Miss Cambridge, I have the sort of secret hopes that someday Natalia will get recruited away by Harvard, we can have a house on the cape, and I can have four seasons back. But I can’t really complain about where we are.


Will Bachman  02:51

Wonderful, so much to explore there. Talk to me, let’s start with some of the tech companies you’ve been involved with. Walk me through that journey. Yeah,


Mark Jacobstein  02:59

it’s, you know, it’s interesting. I have, I think one of the more diverse careers in tech that I can think of a lot of people who, you know, they go into tech, and they stick with a theme there. I don’t know, they build enterprise SAS businesses, or they build, you know, genomics companies, or what have you. And they do to Moszer made us the same thing for 20 or 30 years and have a lot of domain expertise. I if I have a sort of a common theme in my career, it said I sort of continually switched that there’s more to it than that. But so I started my very first real job out of college, was writing software for Mike Bloomberg. Bloomberg, in in the early 90s. And while I was there, watching sort of the power of networked computers, and you know, the internet with a capital, I didn’t exist yet, but Bloomberg was an enterprise example of the same sort of things that were happening with things like prodigy and CompuServe. Anyways, I was I was inspired by what was happening with network technologies. And that created my first business in my living room on the Upper West Side in 1994, with Scott interviewed from our classes, as well as our third partner, Seth, and that business was the first online fantasy sports business in the world. So in some ways, sort of, sadly, if I have a claim to fame, it is inventing online fantasy sports, which, which I did 30 years ago now. And we built that business for quite some time before eventually selling it to Paul Allen in 2001, and it was, you know, it was really heavy. We made every mistake you could possibly imagine. We were 24 years old, we were naive. I knew nothing about business, let alone you know, starting a technology company. There were no blogs. There was no internet to have blogs there. Nobody written The Lean Startup. There was no tech startup ecosystem in New York City. It wasn’t even really one of the Bay Area. By the way, we know it now, but certainly nothing in New York. And so, Scott and I made sort of every mistake he could possibly make. But we, you know, we had a good idea. And so, small world work sort of despite, despite our best efforts. And so we ultimately, we built the first online fantasy sports business in the world. That was, for some time, one of the bigger consumer sites in the world and had enormous traffic for that period. That led to all sorts of problems because of course, there were no cloud, there was no cloud computing, they were we had literally like stacks of servers in my living room for a while, and eventually in a tiny little office on the Upper West Side of Manhattan. And then we spun out a web consultancy in 1995. Because we had to pay the bills. I mean, it wasn’t that we were sort of pressured into about where the internet was headed, it was more that we had to solve a variety of problems, we realized we could solve these problems for other clients. So we built I’m not even I’m not sure, but we think we built one of if not the first stateful websites in the history of the world, one of the first Database Driven websites in the history of the world, all sorted to make our games work. And then we discovered that this was useful for corporate clients, we ended up building the corporate websites for companies like Xerox, and, you know, we did consulting for McKinsey on what the internet was going to mean. And the hilarious thing, I mean, we were 25 years old, we knew nothing about nothing. But you know, I guess I suppose in the land of the blind, the one-eyed man is king, we had we had an inkling of where things were headed. And so it was, we were able to grow that business as well and sell it to a company called I excel before their their IPO in 1998. And, you know, it was, it was an amazing education. I had grown up, I’d never dreamed I was going to be an entrepreneur, or businessperson, I think. I’m not quite sure what I thought it was going to be when I grow up grew up, but it was I had grown up in a liberal sometimes actually fully progressive, you know, family, and I don’t think I appreciated the power for businesses to do good in the world. Certainly not, you know, while I was a high school kid or an undergrad, and it was really only because I had an idea, and wanted to do a thing that this happened. And I was able to talk Scott and Seth into, into building this business and when I say we knew nothing, I mean, we didn’t know how to raise money. We didn’t we didn’t know do anything except I suppose recruit talented people to come work for us because we had a vision, which it turns out, I suppose as an entrepreneur is the most important thing. I had a funny conversation actually with was actually a classmate of ours. Jason Berman’s father was one of the only people I knew who might be able to write us an angel check. And I remember talking to Jay Furman in 1994, about investing in our business. And we asked him for $60,000. And I remember years later, after small relative actually succeeded, and we’d sold the business to Paul Allen, and we’ve had, you know, at least some, some financial success with it. He laughed. He said, If you’d asked me for, you know, a million dollars, I would have said yes. But when he asked me for $60,000, I realized you had no idea what you were talking about, and then a terrible investment. And he was probably right, anyways. But it was an extraordinary time in the 90s. We were very, very, very early and lucky to be so and, you know, a lot of painful lessons in how to build a business, but also an awful lot of fun. And so that was really the first decade and I can walk you through all the different things I’ve done. But I will say that the one common thread that I have look back on now 30 years as an entrepreneur, is that I’ve always looked for sort of systemic, you know, paradigm shifting, changes in technology, which I had nothing to do with, right, I’m not I’m not an actual scientist, I don’t go deep enough in the stack to be the person who’s inventing HTTP or inventing next gen sequencing or creating mobile phones. But I think I’ve always been good at seeing what those new technologies will make possible. So you know, I built two consumer internet businesses in the 90s. I helped build three mobile businesses in the 2000s. I helped build two genomics businesses in the 2010s. And in my last two companies, plus my new venture studio are all sort of machine learning and AI oriented. And as I say, I’m not somebody who goes deep. I’m somebody who’s fairly broad. So if there’s this this theme in my career, it’s looking across the different areas that I’ve been in sort of pattern matching playing lots of different threads together. It’s sort of where my Happy Places professionally is the sort of creative work that happens when a new technology makes new things possible, hopefully things that are both good for the world and for which there’s a lot of demand. And, and that’s really what I’ve focused on more than anything else.


Will Bachman  10:26

So you said that you never dreamed of being an entrepreneur when you were a kid? No, I’m curious if you can recall. What was the transition? Like? Do you remember a point in which you started thinking, Oh, I guess I am an entrepreneur. Maybe it wasn’t a one when you came up with this idea of a fantasy sports thing online. But there must have been some point where you started thinking of myself as Oh, this is my identity. How did that transition happen? Yeah,


Mark Jacobstein  10:59

you know, I think I think it happened you right? I think when I first started up small world, it wasn’t because I want to want to be an entrepreneur. It wasn’t that I wanted to make a lot of money. It wasn’t that it was that I had an idea that I thought people would respond to and it seemed, this isn’t even true. For me it like, in some ways, sort of blindingly obvious that this should work. I mean, at the time, there were 2 million people playing fantasy sports offline. Like I didn’t invent fantasy sports, I was a guy named Dan O’Connor and to invented rotisserie baseball, and the rotisserie restaurant and actually later was on our advisory board, in part because I wanted to thank him for sort of doing this, but I realized that this was going to be an order of magnitude better.


Will Bachman  11:41

Because before, before you guys, people were doing what they would have to


Mark Jacobstein  11:44

excellent paper. And if they were lucky, you know, Lotus Notes spreadsheet, and it was there was an extraordinary amount of work involved. And the funny thing was 2 million people were playing despite that. And I will say one of the lessons for me, and it’s something I’ve tried to apply in every business I’ve looked at ever since is you look for latent demand. I mean, if 2 million people are willing to do something that is horrendously difficult to do, you know, I thought I’d pick up an order of magnitude more participants. When we made it easy on the internet, I was wrong. We picked up two orders of magnitude. I mean, I’m not sure what the numbers are today, but probably three 400 million people play fantasy sports. I don’t actually like what it’s become, we never did gambling, one of the one of the things that probably kept us from I know what kept us from making a lot more money and, but certainly allows me to sleep better at night. You know, I never want to enable somebody’s addiction. And I think very early in our career, Scott and I had to make some decisions around did we want to build a business that we felt really good about? Or do we want to follow follow the path where there was the most money and we made a very clear decision not to do gambling, although, you know, it was also it was not yet clear that it was legal. And we didn’t want to be a test case for the Justice Department. But I also had a very, you know, fortunately, you know, you don’t really know until you’re actually tested on these things. I several times in my career felt like, Okay, this is a choice. And we’re going to make the ethical choice, not the go after the money choice. But I think to go to your original question, like when did I start to feel like an entrepreneur, I think it’s when we started to hire people. You know, it’s one thing, the first six months of small rolled was Scott second is sitting around, either Seth’s living room or later, Scotland, we’re also roommates, our living room on the Upper West Side, literally eating the same meal from the same takeout place every night. Because it’s all we could afford. It was like the cheapest Chinese takeout we could find on the Upper West Side. And I still have my job, we also have our jobs, you’re sort of coding at night, from, you know, 6pm until one in the morning, and then on the weekends. And you know, that was sort of fun, that I mean, it was hard, but it was fun. It was like a project. It was just us and then and then we hired our first employee. And actually interestingly, even though he was only a little bit older than us, he was married and was contemplating having kids and wanted to buy a house in Queens and all these things were so you know, he was adulting and which was her mind blowing for me. And we really need to go you gotta pay the bills. Like you know, we got it was just a three we were paying ourselves anything I’m remember when we sold the consulting business, I excel in 1998. I’ve been paying myself $24,000 a year for four years in Manhattan when we paid ourselves which wasn’t always remember actually, when we sold, you know, small guy Excel for was, you know, millions of dollars. The very first thing I did was pay off my Amex bill. I’ve been sort of like rolling credit cards to help, you know, keep the lights on but I think you feel it as an entrepreneur when you have people who are relying on you and you and I think it was sort of the wake up moment like okay, there’s no guarantee this will work. Work of horses is, uh, you know, this is a high risk venture. But to the extent that we can make it work we need to because people are paying their mortgages with our salaries and all the rest of it and present, you know, it was driven home again, you know, years later during crash when I had to lay some people off, which, you know, I’ve had to do it two or three different times in my career, which is never any fun for sure.


Will Bachman  15:26

So it becomes real when you start paying someone, it’s no longer a hobby. What were some, you said, You made every mistake? What were some of those mistakes that you made early days?


Mark Jacobstein  15:38

Oh, I mean, we made mistakes, right from the right from the jump in terms of how we were structured for our decision making between the three partners. I think we were so naive, we believe that the three of us who are all, you know, bright, hardworking, right, thinking people could never disagree about anything. And so we didn’t put enough thought into like, what’s the process going to be when there is a disagreement, and that ultimately caused friction and sand in the gears that was probably unnecessary, and not only was difficult for the business, but it helps to rupture some friendships. Scott and I are still very close. But you know, we’re not particularly close deal with Seth, which is unfortunate, because he’s a wonderful guy. And I do think if we got it right, in terms of even thinking about how we would make decisions, we would be in better shape. But I will say that by far, by far, the biggest mistakes we made a small world were sins of omission, not Commission. It wasn’t what we did, it was what we didn’t do. So we were so early, that we saw things that we should have realized, were monstrous opportunities that literally nobody was taking advantage of, that we could and should have. And I’ll give you two concrete examples. ones are trivial. And one not. The trivial. One is that in 19, up to 9495, we had a summer intern, whose name was Matthew funk, who I looked up years later, LinkedIn tells me he’s gone on to be a hedge fund manager. But anyways, Matt funk at the time, was like a sophomore for Oh, at Yale, who was like the son of our landlord, literally. And we hired Matt for the summer. And he came in one day. And he said to us, you know, we should buy up all these domain names. It was this is like 9095, you could buy like, you could buy, I mean, everything was available, there were maybe a few 1000 domains that had been registered. And the ethos at the time was you don’t register a domain unless you’re using it for a business purpose. And I remember, we sat down with Matt, and we lectured him on how unethical this was. And this is like, you know, our billion dollar, literally probably a billion dollar mistake. I mean, we could have gone and rolled up all these domains. It’s a trivial example. And I’m actually, you know, I don’t regret that one. Because at the time, it actually felt like the right and ethical choice. But I’ll give you a more concrete example that, that I’m not proud of. We built the first Business to Business Exchange, we think in the history of the world. So in 1996, we built a website called Text, which was an effort to make the textiles business more efficient. At the time, it was an extraordinarily inefficient business, if you wanted, you know, 10,000 yards of woolens, that were dyed blue of this quality, it’s like to make your sweaters for the gap. You literally got on the phone, and started dialing one of the 50 brokers that you knew who might know where we’ll have that quality might be found. I mean, it’s this is a stark example of the extraordinary things that the internet has given us, right? I mean, it’s incredible when I think about it. So we we were, we built this website because somebody paid us. And literally, they paid us 10s of 1000s of dollars to do this, right? I mean, we were, we were so desperate for cash, like great. We’re paying the bills, somebody’s paying us to do consulting work. And we built this very complex for their time, you know, with data that was only semi structured. And you know, Oracle didn’t even know how to write a license for people doing stuff on the internet. Anyways, we built this website, and it worked. And I look back and I’m like, Oh, my God, we didn’t face Oh, we could go do this for every other industry. Or we could think about the commercial implications of the fact that you can now make markets and we could have built eBay or Craigslist, or, I mean, go on and on. And it was 1996 Man and everything was available. And we knew how to do it. We the technology was difficult at the time, all the tools and the stacks that we have today. They didn’t exist. But we knew how to build staple Database Driven websites when no one on earth knew how to but because we were so naive about the world, I think and because maybe we were focused on the thing we were doing and we were also desperate to pay the bills. I couldn’t start pick my head up Looking at things through 10,000 feet or little 30,000 feet. And so we just missed a bunch of opportunities. And I do think, you know, if I look at where I am now 30 years later, I don’t have probably the energy or focus or drive maybe that I did when I was 24. Plus, I’ve got two small kids who take a fair amount of my energy and focus and drive. But I have a whole lot more perspective, I think I’m probably a lot better at seeing massive opportunities when there are right in front of me. Unfortunately, the world has sort of caught up and the number of people who are running at any given massive opportunity engendered by some shift in technology is far larger than it used to be. I shouldn’t say unfortunately, it’s maybe unfortunate for my opportunities, it’s probably a very good thing for the world.


Will Bachman  20:55

Let’s talk about the the 2000s the arts. So like that’s your that’s your decade of mobile businesses he


Mark Jacobstein  21:02

had so it was fascinating times. So Scott and I sold Small World Sports which was the fantasy sports business to Paul Allen spoke and ventures which was basically a sports business roll up the bought the Sporting News, and he was building an interactive TV channel and he bought us his internet piece and sort of hilarious too, because the whole point of fantasy sports is like you get to pretend that you’re somebody like Paul Allen, who owns the trailblazers and the Seahawks are did while he was alive anyways. But in any case, so you know, after that transaction, I had a burnout at Sporting News. And then I was I was sort of freed to do whatever I wanted. And my plan was to stay in New York. But I got a call from a guy named Trip Hawkins so trip was the founder of founding CEO of Electronic Arts, and then the founding CEO of a company called 3dO, that invented the technology that you think of in the Sony PlayStation. And Tripp is either the most or second most important person in the history of video games. He’s and he’s probably the most Steve Jobs in person in Silicon Valley, other than Steve and he was actually Steve’s first sort of Real Men tea leaves the first business hired apple. Anyways, trip. Fascinating guy, really, he was a legend. I met trip. In our time, it’s all rolled and he called me and he said, I want to start a business building games for mobile phones. And I want you to come out and be my co-founder, the president of the company. And I told him no, I love Manhattan. You know, I was 32. And single in New York and arrows. Life was good. And but I had it was it was tough, because I already seen I’d seen mobile phones in Japan, I worked very hard to try to do a deal with DoCoMo in 99 2004, small world to bring fantasy baseball, to Japan on mobile phones. And I had already developed a thesis that the mobile phone is going to be the one device rule them all I think, you know, 678 years before the whole world figured it out. And and so it was gnawing at me and chip called me back and he’s like, Listen, I’ve got Sequoia and Kleiner Perkins, our lead investors, Mike Moritz is on our board. Mike is the probably the most important venture capitalist in history. Come out to Silicon Valley. I’ll introduce you to everybody. You’d be crazy to say no. And he was right. I would have been crazy to say no. So I packed up my bags, and I moved to California. And it was hard. I mean, I didn’t know anybody out here. Despite having worked in tech, you know, all my friends were in New York or an East Coast. There were there was, you know, a Harvard community in Silicon Valley, but I didn’t really know it. Most of my roommates had ended up in LA and sort of, at least sort of quasi in the entertainment industry are musicians anyways, it wasn’t it was so personally, it was very hard. And it was sort of a lonely time. It was after 911 Which, you know, I’d been in lower Manhattan when it had happened to planes its own right over my building. And I don’t know, I think I was still sort of in a it was it was sort of a tough time in my life. But it was a an opportunity. I couldn’t turn down and I did I believed in the direction of the business. And anyways, I came out here. And it was it was it was interesting, because trip was my first real mentor who taught me anything about business without me having to sort of learned it the hard way. I mean, he wasn’t he is a brilliant strategic thinker. And that was that was that part was wonderful. There are other bits that were less wonderful, but sorry, you had a question. Well,


Will Bachman  24:40

no, no, that’s, it’s nice. Finally having someone to to show you things.


Mark Jacobstein  24:45

Yeah, exactly. And you know, triplets sit down. And for better for worse, he would often have like these three hour staff meetings with the whole company, where you sort of think out loud, and I think it was very interesting. I mean, eventually it was it was a little much but As you know, and he would describe how he thought about distribution at EA and what it had meant for building relationships with all the studios. And as a result, why he literally named the company Electronic Arts because he wanted video game designers to think of themselves as artists and to know that he appreciated them as artists, and hence, they would actually license their games to him, which is what he needed. He was just incredibly sort of thoughtful about all the different parts of making the business work, which for me was eye opening, because I am, at my core, sort of a product person, like I have a degree in computer science. And I understood what you know, you could do with software, but I haven’t although I haven’t written a line of code anybody’s actually executed in probably 25 years. But I always thought sort of from the product out but Tripp thought about things like marketing and sales and channel and cogs. And anyways, and I you know, I, I knew a little but I’d never I’d never had an MBA. I never did my two years in McKinsey, right. And this was sort of my version of that. And, and so, you know, digital chocolate was interesting experience was a high flyer for a little while. But the best thing we ever did was acquire a Helsinki based video game business called Samia that later was the team that created a company called supercell. That you may know, because they’re like a 20 or $30 billion business. And it took upon him and his three finished co founders, and I think they’re like the four wealthiest people in Finland, they all used to work for me and should have continued to work for digital chocolate, except that it was a very difficult environment i i details about it, but like trip trip is a notoriously mercurial figure. And my job as president was basically everybody reported to me and I reported a trip and my job was to sort of separate the wheat from the chaff in terms of his ideas, and then make things actually work. And it was, it was, it was a great introduction to Silicon Valley. I learned a lot. I don’t regret it, but it wasn’t easy. To say the least. And anyway, so after I left digital chocolate, I I sort of floating and I was like, Okay, well, what to do next. And that was when the guys at Sequoia, which is a very prominent venture capital firm out here introduced me to a young wunderkind who they were very excited about, but wanted some adult supervision for and that wonder kid was Sam Altman. So I spent the next couple of years working with Sam, to build a company called looped, where we made a lot of mistakes, including being far too early, with a location based service technology, re smartphone, etc. But it was it was it was a great experience. There were some incredibly talented people, Sam, even then, as a 19 year old before he was, you know, arguably, I don’t know, one of the three or four most important business people on earth, he was just a very, very, very prideful, naturally talented 19 year old, who could spot talent. And we had a lot of great people on the team. And it was really interesting. Nothing accounts for product market fit. We had a product that was a decade too early, and that even if we’d been a decade later, people liked but didn’t love. And so, anyways, we struggled. And then, and then I went and ran a mobile VoIP business called icecool. That was interesting for a lot of reasons, including the fact that I didn’t found it, I was brought in as the CEO and I and I had my entire engineering team in Israel where I had literally I’d never been when I started in high school, and I was for three or four years there was going to Israel every every couple of months. And it was a really interesting experience. And building the team was fascinating and and we were able to sell the company to Qualcomm and that was, you know, that was a, that was a good period of my life. And but then that was that was right around the time that I made this very hard career shift over into health tech, which, you know, I, I have my sort of stock answers for why I did it. One is a joke. It’s not a joke, because I was tired of addicting people to mobile phones, I think Bye, bye. You know, 2011 2012 I figured out that that was in my early 40s that I and I was just accidental businessman. And I really enjoyed a lot of what I’ve done, and felt good about the work we’ve done, but nothing that I worked on felt like it had like, changed the world in some profoundly important way for the better. And I’ve never regretted it fantasy sports is a thing a lot of people enjoy for it. So I have no problem with that. But the idea of working either in climate tech or health tech, and having a more direct impact on people’s lives was really appealing to me. Plus, by 2013 or so I met my now wife, who is a physician, scientist, Professor of genetics here at Stanford. And I actually had somebody in my life who could help me that any opportunities that I would look at in health tech, or biotech, etc. And so that’s how I ended up going over to garden health, which was a molecular diagnostic company, at the forefront of, of sort of machine learning, applied to big, you know, big omics. So, so inexpensive. next gen sequencing, driving the ability to do cancer detection, both both both determination, and then detection, using things like just a blood draw, it was a it was a fascinating company. Happy to talk more about it, but but really the, for me, the big shift was, I want to do a thing that matters with a capital M, health tech seemed like a way to do that. And when I got into it, I also appreciated that the intellectual challenge of working on in this case, you know, circulating tumor DNA for early detection of cancer was more intellectually rigorous than anything I’d ever done in sort of pure tech. And I really enjoyed that part as well. So that was a that was an important inflection point for me.


Will Bachman  31:32

And now, you’ve worked at several health techs, you think he’s Yeah,


Mark Jacobstein  31:36

I mean, I started I sort of stuck with it. I mean, so once, you know, I was when I was with garden for a little over four years running, sort of most of the business of the business, we went from 40 or 50 people from when I arrived through the IPO, probably about 1000 people when I left and and, you know, I think the company is still the second or third biggest molecular diagnostics company in the world. And it was, it was an amazing education. The founders were two of the more brilliant Stanford PhDs that I’ve met, and I’ve met a lot of them merely tell us AWS and LDL Tuki. And they ran an organization with great to rigor, and which I appreciate it, and just a lot of terrific people to learn from. And so I, after that, spent a lot of time on boards, and advising a variety of health tech companies, and then worked with a company called immunized for a couple of years, which was single cell genomics plus machine learning to impact the great mysteries of the immune system and build better immunomodulatory therapeutics, which was sort of particularly meaningful for me, because my father, who’s still alive is alive, because he had a very, very good response to an immunomodulatory therapeutic. And, you know, I appreciate the sort of importance of the work that happens in the field. And also the extraordinary complexity of the immune system, which I think is probably second only to our central nervous system is sort of an fu to entropy in the entire universe. And it’s a sort of a beautiful thing to have to learn about, and really interesting company. But then we had our kids and we had two kids in eight months. That’s a that’s an interesting story in itself. And so I took, you know, a year off to make sure I was really here and present with the girls. And only maybe eight, nine months ago sort of dove back in professionally to building two new businesses, one, which is very specifically in Health Tech, and one which is more orthogonally. So I’m the founding president of a company called Jiminy health, which is building a new paradigm for mental health care, to try to address the sort of extraordinary care gaps we have, basically, almost nobody can actually get the mental health help that they need. And to the extent that they do to effect sizes for the psychotherapy they receive are not particularly good for a slew of different reasons. So we’re trying to change the care care paradigm, and that is enabled by a combination of mobile and MLMs sort of supercharging the work that a therapist can do. So that was really interesting on a lot of different fronts and has some good momentum and a great team and I’m, I’m really excited about that. And at the same time I’ve been building a new venture fund that is really it’s, it’s more venture builders more than were venture capitalist, we only we only work on three or four companies a year and we don’t just invest. We do a lot of work with the founding CEO has to actually get them from zero to one. So I’m sort of, in effect, a fractional co founder for three to four new companies per year through near horizon. which is the name of our fund. And it’s, it’s really interesting and a lot of fun and amazing time given all the things that are happening and AI and ML and and that one’s not specifically health tech focused. But many of the more interesting companies that have come to us are in the field, because a lot of the most interesting data on Earth is in health, whether it’s sort of basic biology, things like, you know, the omics we see from next gen sequencing and the ability now to pull out RNA and eventually proteins, high throughput sequencing, and not just DNA, but all the way through to like, how do we analyze sort of macro health data and figure out how to spend $1 wisely in the US healthcare system, which is a crazy for cockta problem. But anyways, it’s it’s a, it’s a lot, it keeps me busy, but is, in some ways sort of perfectly suited for me, because as I mentioned earlier, I like looking across a lot of things as opposed to being the person who goes extremely deep on any one thing, if that makes sense.


Will Bachman  36:07

Over the past three decades, you’ve been either the President or the founder or the CEO of a bunch of companies. What have you learned that is about how to run a company that is sort of non obvious or counterintuitive? Or that you’re not conventional wisdom?


Mark Jacobstein  36:31

Hmm. Great question. Well, I guess. Depending on who you ask, this might or might not be obvious. I think authenticity is incredibly important. You know, I think my own management style is very different, for example, then, I don’t know. I’ll tell you, someone, I’m not like Elon Musk, or Steve Jobs. I’m not like I’ve never ruled through fear doesn’t work for me, who isn’t who I am isn’t what I want. And but interestingly, although I guess, if I have anything, so from a management style, I’m sort of a higher grade people, get them aligned, I, maybe I say it this way, I’ve always been much more about leadership and management, you know, have a compelling vision. And the most important thing you do as a CEO or president or leader is to make that vision clear. And then help to untangle the knots that maybe an organization has gotten itself into, so that it can to mix my metaphors here, pull towards the common goal, I think. And for me, that style has worked. I think if I tried to be somebody who instilled a lot of fear, that just wouldn’t work. It wouldn’t work for me. And I’m not sure anyone would believe and that doesn’t mean that I suffer fools gladly, or that I don’t make hard choices. When I’m running a business. I do. But it’s just different. But interestingly, when I remember, I had somebody used to work for you who will remain nameless, at small world, you know, 20 years ago, and he really wanted to be liked by like the crew. And every and honestly, he was sort of a jerk. He just was you. Yeah, is like prickly personality and curmudgeonly and, and you know, I think underneath it a good, good person, but not like, he wasn’t a man of the people, as they say, but he really he wanted to be any we used to everyday go over to like, like the engineers and the QA team, and, like, try to sort of glad and backslap and they used to look like human beings, or we have just giant swaths of our brain that are dedicated to telling what somebody is lying to us or not. And detecting BS. And I remember saying one day, just, you know, just be yourself, man. Don’t, don’t don’t try too hard. And it was, you know, for the role that he had was okay that he was prickly Rand corp dev for me, and he was our lawyer. And it was actually useful in negotiations to have him because I was that he was better at saying negotiating a tough contract than I was. But anyways, I think that the small town all that counterintuitive, but I do think that sort of authenticity piece is really important. You know, a lot of other sort of interesting lessons along the way. I mean, I think for me, one of the things I’ve tried to pull from I’ve had a chance to work with some extraordinary people from Sam Altman, to Trip Hawkins to Vinod Khosla to you know, help me out to gie and now I, you know, some of my co founders, Lewisville, Lockett, Jimini, etc. And I’ve tried to take different things from each of them. I will say, you know, for example, from Sam. The outrageous unlimited ambition is one of the things that I think is really interesting, you know, some of the sins of omission that I talked about in the 90s that that we made a small world, Sam would never have made, because he’s always been thinking about, like, the biggest thing, you know. So now that he’s really completely remade the world of AI, with his latest as he’s trying to raise $7 trillion to, to, you know, build all the compute that is, will be needed for the AI future. And it’s just it’s sounds so outrageous, except all the things that he’s actually accomplished started with things that sounded outrageous. We had a conversation 20 years ago, literally 20 years ago, where he was talking about nuclear fusion. And I remember he was 19 at the time and had, you know, one or two semesters of undergraduate education as a CS major, you know, zero semesters as a nuclear physicist. And I remember looking at him like, What are you talking about nuclear fusion? Are you crazy? I didn’t say it. But I was thinking this and and then, you know, I find out 15 years later, he’s started one of the three nuclear nuclear fusion companies that may actually work. So I look to these people that I’ve worked with, were very good at very specific things, and try to pull out pieces of that and sort of apply it to myself, like what would these different people do in these situations? And, you know, I think as long as it’s authentic to me, and you know, squares with my values, I do my best to use that as a lens to think about am I am I’m working on the most interesting and important thing that I can do right now.


Will Bachman  41:28

Talk to me about how you rely on your wife as a counselor. Especially as an expert, you know, in in health care. How do you tap into her knowledge and experience?


Mark Jacobstein  41:44

Yeah, it’s it’s a great question. We certainly have my wife is a is a geneticist here at Stanford, she she runs a lab that does gene editing of stem cells to try to cure lysosomal storage disorders. And then she’s got a clinical practice at the hospital with genetics and sort of a Doctor House job if they can’t figure out what’s happening with a child who’s failing to thrive and it may be genetic in origin. It’s It’s amazing work. You know, it’s interesting. Part of what’s useful about bouncing things off Natalia is he has such a different frame than I do. I mean, again, a joke, that’s not really a joke. I’m an entrepreneur, if I see three lines, I can sort of vaguely fit a spline through I’m like, Hey, there’s a pattern, let’s build a business. And, you know, she’s a scientist, and if she sees a reads a paper, a gust you know, Kol authors who are in the New England Journal and have 10,000, you know, she still wants to read the methods before she decides whether she thinks it’s true. And I think that framing is really useful. The the inherent skepticism that a good scientist brings to things and the precision with which she thinks about a problem and the way she thinks about something sort of all the way down, is very useful, because I’m an optimist. Right? That can’t be sort of can’t be an entrepreneur if you’re not. But a really good entrepreneur or someone who’s an optimist who’s got like a, like a dose of skepticism. And I, you know, for I suppose our class, they’ll still remember this, the young people never know this reference. When I make it. I sometimes talk about Casey Qassem, like Keep reaching for the stars, but keep your feet on the ground. No, none of my Gen Z engineers have any idea what I’m talking about when I say that, but like, for me, Scott Murphy actually sort of provided that when I was a small role, we used to call Scott the chili voice of reason. You know, Scott was like the spreadsheet guy, and I was the dreamer. And now in Italia provides a lot of that. So I will hear about business. That sounds very interesting. You know, particularly if there’s any sort of genomic component. And then, you know, my, my first conversation would be when Natalia like a what do you think of the clinical use case for this thing? How would you react to this tool actually being created? And then be What do you think of the science is hard? Is this important? Do you believe it? Is it transferable and Broadway’s? You know? So it’s questions that I can’t get answered by Wikipedia, you know, and are much more subtle than that. You know, at the same time, it’s interesting, it’s, you know, I do some of the same things for her. I mean, running turns out running a lab is not unlike running a business. You’re constantly raising money, you have to hire people, you have to meet your deadlines, you miss milestones, it’s unfortunate, but it does happen. What do you do that and etc. And one of the interesting things is, of course, they don’t train scientists on some of the basic skills that are necessary for this, like managing people. And I think even even fundraising I mean, you know how to write a grant but there’s there’s more fundraising than just writing NIH grants, of course. And so when we It’s a, it’s a good, it’s a good partnership that way for us professionally, people have laughed about, like, you know, as she spins ideas out of a lab, like, oh, you should go start that business and like, No, that is something I will never do it. Like, that is a terrible idea. I cannot imagine a easier way to put a strain on a marriage and to be like business partners with your spouse. But


Will Bachman  45:24

tell me about any courses or professors that you had at Harvard that continue to resonate with you.


Mark Jacobstein  45:30

Yeah, you know, I was thinking about that in advance of the call. And there’s a few I mean, there’s sort of obvious ones, like, you know, CS, 50, and 51. And beloved Harry Lewis, who was and is wonderful. And, you know, I did, I did concentrate in CS and made my career in tech. But you know, the funny thing is, for me, I’m not really a computer scientist, I don’t do the deep work all the way down. I know enough to be dangerous. But I last wrote a line of code that I think was actually compiled in a production environment in late 1999. I think that the, for me a lot of the a lot of what I’ve tried to do is think about how the work that well, I said earlier that the the most important thing I think I do as an entrepreneur sort of have an is to have ideas about what the future could look like. And then articulate that vision and a path to get there. And all also sort of noise. I mean, if you do that, well, it allows you to recruit a team, it allows you to raise money, it allows you to attract customers, and then there’s all the operational complexity that comes with it and tactics, etc. But like, you know, great CEOs, founders, like, it’s, it’s about sort of have the vision and articulate the vision. And so I actually think that in some ways, the classes I took that were about expressing yourself, whether it was, you know, writing class I took as a senior or even classes about that, for me, it’s ultimately about reading, which ultimately not communicating were important. I mean, I think the literature of social reflection, I know, it’s ridiculous, right? You know, Robert Coles, the easiest day at Harvard, but like that class meant something to me, both because it sort of spoke to me about how like, telling a story can change the world, right. And as a business person, articulating a story for the thing you’re trying to build, can change the world. And also, I think that, for me, having sort of a, an end in mind, world, you want to create an ethos that you care about, has made it possible to put in the hard work involved in making these businesses, I mean, Jiminy health, which is my mental health startup, is working on what I think is one of the most important problems on Earth, were trying to make scalable mental health. I mean, if there are saying, like, anxiety is a feature, not a bug of natural selection, like we’re all anxious people and mobile phones have made it far worse. And mental health crisis, especially for young people is profound. And so for me the ability to work on a company that I hope that is the curve they’re on and you know, changes the way mental health services can be provided and to buy to any care at all to 10s of millions, people who get none, et cetera, feels really important. And I will say, for me that that’s one of the nifty ways x squared, the circle, being somebody who was raised in a liberal, maybe progressive family who still wants to, you know, my businesses that I build to make the world a better place. But that it’s different than I don’t know, being involved with, you know, activism or working for a 501 C three are various things that are not what I ended up doing, or even being a journalist, which is, I think, what I thought I was going to do when I was 22. So, yeah, it’s a funny answer. But I do feel like that, that Robert Colas class was important. You know, the only other thing I mentioned, well, two others. One was my time at the perspective where I spent a lot of time, you know, thinking about the impact of policy decisions on the world. And I now spend a lot of time thinking about the impact of technology and technological shifts on the world, and how that actually played into sort of my senior project. So I didn’t write a computer science thesis. So I have this really weird degree. It’s like Koolau in general studies with a concentration in in computer science. But, but the instead I wrote a senior paper in a different department in the history of science, and was all about sociobiology, and the sociobiology controversies in the 70s at heart largely at Harvard with people like Richard Lewontin and EO Wilson. And Stephen Jay Gould writing essays back and forth about how their politics, so influenced their science, and vice versa. And for me, in some ways, it was a reflection of my interest in what happens with science and technology and this sort of concomitant changes in the world. And the, in some ways, I think of my career as a version of exploring that except as a participant instead of as a as a journaler. And and it’s been a, it’s been an interesting 32


Will Bachman  50:35

years for sure. Amazing, Mark. I know our time is up. Thank you so much for joining today. For listeners that want to follow up with you. Where can they find you online?


Mark Jacobstein  50:44

Yeah, so my venture studio is near The mental health company is Jimini And you can find me I mean, there are only two Mark Jacobstein’s on Earth. The other one’s an MD. That’s not me. So, I’m easy to find on LinkedIn. I’m just mcjacobstein on Twitter. For any classmates, especially those who are in the Bay Area. I’d love to reconnect and we’ll really, really appreciate the conversation and appreciate you putting this together.