Sergio Monsalve is a Founding Partner of Roble Ventures, a venture capital investing firm based in Silicon Valley that invests in human enablement technologies: solutions that help human progress.
Sergio is also visiting professor at Stanford University’s Graduate School of Education and Business. In both roles, he is focused on the “Future of Work and Learning” and on developing technology innovations and entrepreneurship.
Sergio has been on the board and/or an investor of various companies in this area of focus, including Udemy ($3B), Adaptive Insights (Sold to Workday for $1.6B), Ubits, Slang, and Kahoot! Before he started his investing career, he was an entrepreneur and also held various roles in high-growth technology companies like eBay.
Sergio holds an MBA from Harvard Business School and a bachelor of science degree in management sciences and engineering from Stanford University. Sergio is originally from Mexico and is very active helping aspiring Latinx entrepreneurs and VC’s.
Recommended Resources
Outliers by Malcolm Gladwell
Peak by Anders Ericsson and Robert Pool
Sergio Monsalve is a Founding Partner of Roble Ventures, a venture capital investing firm based in Silicon Valley that invests in human enablement technologies: solutions that help human progress.
Sergio is also visiting professor at Stanford University’s Graduate School of Education and Business. In both roles, he is focused on the “Future of Work and Learning” and on developing technology innovations and entrepreneurship.
Sergio has been on the board and/or an investor of various companies in this area of focus, including Udemy ($3B), Adaptive Insights (Sold to Workday for $1.6B), Ubits, Slang, and Kahoot! Before he started his investing career, he was an entrepreneur and also held various roles in high-growth technology companies like eBay.
Sergio holds an MBA from Harvard Business School and a bachelor of science degree in management sciences and engineering from Stanford University. Sergio is originally from Mexico and is very active helping aspiring Latinx entrepreneurs and VC’s.
Recommended Resources
Outliers by Malcolm Gladwell
Peak by Anders Ericsson and Robert Pool
Welcome to Ed Tech insiders. In this podcast we talk to educators and educational technology investors, thought leaders, founders and operators about the most interesting and exciting trends in the field. I'm your host, Alex Sarlin, an educational technology veteran with over a decade of work at leading edtech companies. Sergio Monsalve is a founding partner of a roleplay ventures, a venture capital investing firm based in Silicon Valley that invests in human enablement technologies, solutions that help human progress. Sergio is also a visiting professor at Stanford University's Graduate School of Education and business. In both roles he's focused on the future of work and learning and on developing technology innovations and entrepreneurship. Sergio has been on the board and or an investor of various companies in this area of focus, including Udemy adaptive insights ubit, slang and Kahoot. Before he started his investing career, he was an entrepreneur himself, and also held various roles in high growth technology companies like eBay. Sergio holds an MBA from Harvard Business School and a Bachelor of Science degree in Management Sciences and Engineering from Stanford University. Sergio is originally from Mexico and is very active helping aspiring Latin ex entrepreneurs and VCs. Sergio, welcome to Ed Tech insiders.
Sergio Monsalve:Thank you so much, Alex. Thanks for having me. Very exciting to be here.
Alexander Sarlin:Yeah, it's great to have you. So Sergio, your work with Norwest. And with roadway ventures. It focuses on Ed Tech and the future of work. And you come to it with an extensive career in entrepreneurship and in education. So give our listeners an overview of what brought you into the field of edtech investing.
Sergio Monsalve:I can take a little second year to give you the chronology of my background because he kind of has built on itself over the many years. I'm originally from Mexico and came to the US when I was 13 first generation kid came to San Diego went to high school there. I love STEM subjects Math Science, in landed at Stanford actually enrolled blade Hall. Robley Hall is the biggest, the most inclusive dorm at Stanford that has a long history of inclusivity and innovation. And so I need my fun roleplay ventures because of Robert Hall. And also, it's OIC in Spanish. So that's a little trivia for you. But as I got into Stanford, I noticed that the world opened up for me, but unfortunately, it hasn't opened up for a lot of other Latinos, and people of color as well as women over the many years. And that stuck with me when I was going to school to how privileged I was to be in a place like Stanford. Later I went to work in New York and went to business school at Harvard Chien back a worked in a variety of areas as an entrepreneur and technology, including places like eBay, where we enabled a new breed of workers to make quite a bit of money, some of them made, household living, and the beginnings of what we now know as the gig economy or the two sided marketplace, work enablement movement. And so that stuck with me as well, in how the internet, even in the beginnings of it and back in, I think it was a late 90s event, we could create something like new employment opportunities for people. Fast forward to 2007 I became an investor through Norwest Venture Partners I was there for 1314 years, in my last eight or nine, I became very focused on this theme that I initially I didn't know what to call it. I know a lot of people call it future learning future work. What I ended up doing is I kept investing in application layer software and consumer, either consumer or enterprise software solutions that really helped with not only were they great businesses, but they were also great for society. And what I meant by that, eventually, when I started roleplay, I coined the term investing and human enablement, because I think that what we need to do in society is to invest in technology that allows for the 99% of folks that haven't participated fully into this great world of technology to participate by creating an ability for them to get skilled rescaled upskill to get new types of promotion opportunities in the workplace, as well as create new types of job opportunities. Like we did an eBay early on and, and another one of my companies called Udemy has done for instructors, where some of the instructors in that platform make over a million dollars a year teaching in a very new way. Right. So new employment, new ways to work. New promotion opportunities for a broader set of people is essentially what led me here and it's been in the making since I even I was a little kid in Mexico City immigrating to the US so I think it's come full circle Oh,
Alexander Sarlin:yeah, it's an amazing story in this very clear through line throughout about uplifting society and making sure that the tools for education and work are in place that people are unable to move to a new level of success and that the doors are opened. And it doesn't feel like a very in equal educational and work society, which unfortunately, sometimes it still feels like we're in. There are so many interesting things in your background, you mentioned right at the end there that you worked extensively with the learning platform Udemy, which, as our listeners know, IP owed in 2021, after many years of growth, it's a creative marketplace with teachers from all over the world. As you mentioned, I'd love to ask you how you first got interested in Udemy? And give us a little bit of insight into that company's growth? And what are some of the key decisions that led it to become one of the world's largest learning platforms?
Sergio Monsalve:That's a great question. That story of Udemy goes back to 2010. When I made my first investment in education, technology, back then, in 2010, the conventional wisdom was that investing in education was the worst thing you could do. Because there had been many, many disasters, you had to deal with the government, you have to deal with content creation. So there was a real wave of pushback in investing in education in general, back then, there had been a lot of losses in venture capital. So that actually motivated me because I like to invest in themes, I believe in from a high level perspective, but also, where there's a huge demand on the ground floor of the customer centric view of the world first principles, looking at what customers really need, what gaps are in the market. So that intrigued me, I thought, Well, I mean, it's great to be contrarian and right, or contrarian and wrong. I invested in my first company in 2010. And frankly, that didn't work out for a variety of reasons. But what stuck with me is that over the time that I was on the board of that company, one year and or two years, and I started realizing that education needed to be revamped both K through 12, higher ed, and also this new world, that had a lot more Greenfield because there was no incumbents in that world. So the world of education, in general could be viewed as Kid education, K through 12, then there was obviously higher ed, which has its own system and players, incumbents, a lot of colleges, community colleges and things like that. And then in 2013, I sort of started asking myself a little bit and meeting a lot of different players that I brought in, or some of my partners that always brought in, I started looking at different players. And I started sort of scratching my head saying, well, it doesn't make sense that we, as humans, end up learning from five years old to 21 years old, if you go to college, but then from 21 years old to 100 years old, or 100. Plus, there's no more formal education, there's no industry to supply that, except in small cases, like executive education, which is very expensive. It's only available to a few executives that are privileged enough to get that kind of formal training. So I said, you know, this world has to change. Because when you look at how fast the economy is changing, you are going to be disadvantaged as a human, you're going to be out scaled by computers and computing power that get downloads of new information and new knowledge by the second, right. So why is it that computers can get new knowledge constantly, and humans have to stop learning formally? A 21 year solid never get back to the classroom in a formal way. So that got me thinking that? Yeah, sure. K through 12. and higher ed, have a lot of incumbents that creates complexities in that ecosystem from a venture investing perspective. But Lifelong Learning had no players. And so it was really a greenfield opportunity. So not only was it contrarian, but it was being filled in that's where I started really thinking. Okay, let's meet with a lot of different players and learn more about this lifelong learning market. I fell in love when I first met the den coo Dennis Yang, in the founder, Aaron Bolli, the CEO at the time, I just fell in love with a model I fell in love with the fact that it was a two sided marketplace. The fact that it empowered the supply side to make money beyond the four walls of a classroom. And on the demand side, I saw that you can make education affordable to anybody around the world in a very efficient way. What I really loved that it was not 1000 $2,000 courses, it was really 4050 $100 courses. So it was very achievable for people to educate themselves on the demand side and supply side. It was very inspiring for instructors to be able to go beyond the classroom to make a hustle living for themselves.
Alexander Sarlin:It's really interesting to hear you talk about Udemy from an entrepreneurial standpoint And coming from that that original thesis of lifelong learning is going to be such an important part of the education ecosystem, and nobody was really playing in it. I definitely agree with that. I think of Udemy as a sort of marketplace first, and you mentioned a lot of the marketplace dynamics in there. But you're absolutely right, that you know, at heart Udemy is about having very easy low cost access to learning from anyone in the world. And then on the curriculum creation and teaching side, the ability to make secondary or even primary income by teaching what you know. So hearing that entrepreneurial aspect of it gives me a whole new respect for their business model.
Sergio Monsalve:Yeah, no, it's great. And from that, I mean, they've been innovative, continuously innovative, because I do think that the interesting thing about education, if you really abstract education, it's that it's, it's a hard endeavor, right? So it's a little bit like working out or eating nutritiously or eating well requires some discipline, because it's not necessarily like other activities, like gaming, or like recreational stuff that you like to do, or going to Starbucks and having coffee with your friends. I mean, those things are fun, and they're easy to do. And when you think about activities that people need to do, and require discipline, require repetition requires some tenacity, you have to create a system that makes it fun and engaging to do it. And so that's one thing. The other thing you need to create is an ability for the learner to get some help. I use the example of peloton for example, where you get an instructor that or a private trainer, or a class that you take sometimes the methodology, you need a class, you need motivation, you get peer support, you need your boss or your company to kind of say, put it in your review and say, Hey, it'd be great if you learn this because it can help you move up. So you get coaching from that standpoint as well. So what Udemy has done is evolved that so now they created Udemy for business, which is now a way to for the corporation to incent their own employees to take courses. But they haven't stopped there, they acquired a company called core view, which is now creating sort of cohort based learning so that you, your peers, enable you to also learn, you get the accountability from your peers and the help from your peers. And you can learn much like how you do it in a college setting, for example, in a college dorm. And so I think education is not a one solution thing, because some people require motivation from different sides to essentially accomplish our task, which is to feed your brain with goodness, right and just like you do your body with food and and you go to the gym and workout, I think those activities are very similar and that they require a certain set of capabilities and tenacity for you to kind of get through it and accomplish your goals.
Alexander Sarlin:Absolutely. Speaking of that motivation and helping learners stay engaged in build tenacity. Another really interesting edtech company in which you've invested in the past is Kahoot, the European edtech company that is fast becoming one of the world's most popular and most often used edtech products, it's really blown up like crazy. So for the EdTech entrepreneurs and investors who listen to this podcast Kahoot has really rewritten the playbook on some of the ideas you just mentioned about making learning, engaging, social, and exciting. As a professor of entrepreneurship. I'm really curious how you think about the good business model and its platform and what has contributed most to the enormous growth of that company.
Sergio Monsalve:This is super interesting, because it also plays on a sub theme of human enablement that I've been pursuing. So in 2017, I co founded a program at Stanford, that was the EIR program at the Graduate School of Education. And that was meant to be program for a practitioners that have worked in the field, whatever the field of education they worked in, outside of academia, to come into Stanford in essentially contribute some of their knowledge from the world, right? Much like engineering and business and medicine I've done at Stanford, especially, I've really brought in practitioners, the GSE really noticed that we needed to bring practitioners along with academics to really enhance the experience of the students and the research too. So I created this program, co founded it with the CTO and assistant dean. That's now i The e ir program at the DSC. And out of that, I also created a new course, which is the entrepreneurship course. As I was teaching my first class in 2017, I believe 2018. I ended up using Kahoot to just make the environment in the classroom more fun. And so I experimented with a bunch of different applications, because I wanted my students to really have fun in the classroom, right because it's, I think that bio rhythm and the mentality that you have going into the classroom has proven in this is not just means I mean research rooms that when you're happy and you're enabled and you're having fun, you're going to be much more receptive to do these hard tasks that I mentioned, you better workout learn, I've been intrigued by this notion that if you're having fun, you're going to be doing more of that activity, period. It's not rocket science. What ended up happening is, I used CUDA in my class. At the same time, my kids were actually using it in their class. At the time, I think they were in middle school in high school. And I saw that there was an emerging theme that I needed to pursue. So I reached out to the CEO of cocoon, and Norway, out of all places. And I ended up being able to get in personally actually not to Norwest to invest in the series se, which is, I believe it's in sub 50 million valuation. Few years later, they went public at a $4 billion valuation, I think they're still around that. So it's a big success. But what that taught me is that there is a theme that I need to continue to pursue, which is to make education fun to gamify education to make it much more engaging, much more addicting, and therefore increase the daily active usage, or the monthly active usage or the weekly active usage, because frequency is what can get you to be proficient, whatever you do, it's almost like, how do you get to your 10,000 hours of reps faster, of course, it's going to be done when you're having fun, right? Because you're gonna do it more frequently, you're gonna do it more actively more intensely. So that's how I got to go, who would I say, you know, I got to it because of serendipity, teaching and being a professor myself and observing my own kids. But at the same time, I then zoomed out, and now in roleplay, I have this theme sub theme that I'm pursuing around making education fun and gamified. I've already made two additional investments that play into that one's called kinjo that essentially is going to be an amazing platform for understanding what people learn and gamified environments. Then, number two is in spirit, which is a way for you to create very fun biology and any kind of science lab in a 3d environment and eventually, web three, two. So I think that this, Steve will continue because I think we have a long way to go to create a really engaging and exciting educational environment. Much like by the way, Baidu is one of the great examples of a company that in India has initially and then yeah, but now, in a lot of different places, has done an amazing job at making education interactive and fun.
Alexander Sarlin:It really feels like we've crossed a barrier as an ad tech ecosystem in actually finding some truly engaging fun ways to, to teach and learn after there was a wilderness. I think for a while where people were talking about making learning fun, but weren't exactly sure how to do it. And now I think with companies like Kahoot, and by Jews and some of the companies you just named, we're starting to really break through in some interesting ways. Gamification, and engagement in education was actually what brought me into the field. Originally, way back, I was a tutor for students and constantly seeing them being caught up in all of the games, they were playing so much more and all the entertainment options, so much more than their homework and schooling. And I had a similar realization that you just said, education really should and could be fun. And if it was more interactive, and fun, students would put so much more time into it and be so much less distracted by all of the other options. So speaking of the themes of Robledo, one of the other themes that I've seen in your portfolio, and it sort of parallels one of the themes of the tech insiders podcast is that edtech is becoming a more and more global industry, you just mentioned Kahoot, out of Norway, and UK, you mentioned by Jews in India, and a significant portion of your portfolio is focused on companies that are in international markets around the world. So I wanted to dig down into a couple of them with you and hear your thoughts about those markets. So let's start with UberEATS. It's based in Bogota, Colombia. And it seems to be sort of the Netflix of corporate education, quote, unquote, in Latin America just got a $25 million round, quite recently. I'd love to hear your take on UberEATS in particular, and Ed Tech growth in the Latin American market.
Sergio Monsalve:It's a great example of a few things that I'm pursuing, but broadly with human enablement. Number one, human enablement is not just about the types of companies that I invest externally like so that human enablement has an external strategy and an internal strategy. Internal strategy is all about making sure that you invest in enabling all people in a very inclusive way to participate as executives and board members. So the number one thing that I bring to the table is the ability to have the affinity and empathy to diversify a board It diversify a C level executive team so that you don't have groupthink, right? Too many years I spent in boards where there is just too many of one kind of person that came from the white kind of background, one kind of gender one kind of ethnicity. And in that created groupthink, not intentionally, there were situations where everybody agreed with each other. And they agreed to the wrong answer, actually. And so I think that the best situations when you create a diversity around the boards on ubit, is one example of a founding team that's a woman, Colombian woman in LA, in Colombia, and man in Mexico City that came together and create a new beds. That team has incredible diversity, geographically, ethnicity, and also from a background perspective. So that in itself is part of the theme that I'm pursuing around human enablement. But when you think about what units does, it actually extends on what I learned at Udemy. And in what Coursera has done with others, rural side LinkedIn learning I've done in the US and starting to do in internationally, what ubit has done is to really have empathy around the different cultures in Latin America, not because everybody speaks Spanish and Latin America, are they the same culture. So you have to have complete empathy on how to create courses that are authentic, and also well accepted, depending on the culture depending on who's teaching it to what audience in, I found that, that in itself, plus their ability to get to market in a much more efficient way than anybody at the US, I found that those examples would create a very defensible company that essentially would be like, well, Yan has mentioned, or Martha has mentioned, the Netflix of Latin America and the education front, or it could be the Coursera or Udemy, of Latin America. So I think that their library of content is extremely authentic, their go to market is extremely differentiated. And that's what allowed me to kind of invest in something that in Latin America, that from a high level view, it could be viewed as a copycat of the US models. But in reality, that's not the case, I actually don't like to invest in copycats, or anything, because each region has its own way to attach and create differentiation. I learned that very early in my career at eBay. And Mercado Libre are two very, very different companies, even though they kind of started somewhat similar to gallantly RIA has exceeded all kinds of expectations, and created a massive ecommerce company in Latin America. So I don't think that when you go into a different region, you should just copycat the model that is in more developed country, you have to actually create new differentiation to be defensible,
Alexander Sarlin:really, really interesting take on where you bits is coming from. And I love the points that you're making about that rather than copying an existing model or sort of importing from a different market, to try to really build deep empathy and understanding for what the learners in any particular region truly need. And sounds like the content coming out of you, which is designed to really, as you say, empathize with learners from different countries, and really help them build their careers in ways that make sense to them. It doesn't feel like it's just sort of imported from elsewhere. And it brings me to another one of your investments, which is you lesson. So we have Udemy you bits and you lesson you listen is ed tech startup based in Nigeria, that sells digital curriculum to students, often through SD cards, so that they can be accessed even in an internet free environment. Africa has one of the youngest and fastest growing populations in the world, but has been one of the last frontiers of edtech development. And your points about empathy are so interesting, what excites you about your lesson and the idea of supporting African students in this way?
Sergio Monsalve:Yeah, cincher guy is just a Jedi Master and a real great entrepreneur. So I started there, he and I met, he had just finished his Harvard Business School study MBA, I met through my friend said, All ventures, story Patterson, and others what co invested both the ubit and you lesson, and hopefully more there, I consider them one of the best education technology investors out there. I first met Sam, I was very impressed with how he thought about the business he was building. It fit right into my thesis around education should be fun and engaging. The demographics of Nigeria, very similar to other emerging countries, including mine, Mexico, where the population is very young, very progressive. They're getting digitized very quickly, much like India, I saw buys you really creating an incredible company, essentially creating what we should be creating in the US displacing some of the traditional publishers and creating the kind of the Bible view of the US although because we have more incumbency here, it's much harder to do that here in the US. API has been able to do it. Do Baijiu but I think you less than is going to be able to do it in West Africa short night, starting with Nigeria and other places where the demographics are similar to India to Mexico, very young, progressive, the applications they're building are incredibly addictive. And so what got me is that the content itself is very promising, very empathetic to their country very localized. And so it's very hard to copy. So I think that sends off to an incredible start with an incredible trajectory momentum already. So very excited to be an investor in his company.
Alexander Sarlin:It's really thrilling to see companies grow quickly and really make a difference in markets that in the past, were not just not happening in the ed tech world, I just think people weren't yet interested in running towards certain populations, and investors were not ready to help support them. And I think we're seeing this incredible globalization of edtech. It's been fascinating, especially over the last couple of years. So there's one more I wanted to ask you about. It's an unusual, a really interesting one, the company slang, which is an online platform for English language learning. They've offerings for individuals, universities, corporations, and ESL schools, and their classes focused on specialized professional vocabulary. You know, I have more details about them. But why don't you give us an overview of slang? And what's interesting about it, it seems like a fascinating platform.
Sergio Monsalve:Yeah, so that was super interesting to me, because I've seen from afar that success of Duolingo, on mainly a b2c model, right, or a C to C model. I think language learning is super important. The type of language learning that I'm seeing grow much more in the corporate environment, which is what slang focuses on, what they do is sell essentially an ability for you to learn a very vertically focused language, essentially, English, you learn English, but specific to your vertical. So they sell it to corporations that are multinationals where there's employees in different parts of the country that need to understand and communicate in English very, very deeply, very technically, because their technical jobs are very specific jobs. So think of any kind of engineering job, any kind of finance job, any kind of anything job where you have a different way to communicate. And you have to communicate with your own co workers in different countries. But it's all done through English. So the thesis there is that the world is, is standardizing around English. And that has been happening for a long time, there's plenty of data to support that. That's the language of the world. That's the Language of Business. So we want to accelerate that and accelerate it in that formal learning environment, where slang is essentially creating a very efficient, AI driven way to create courses within the context of your vertical industry so that you could actually learn the language faster, the vocabulary faster. And they sell that to corporations, very much a recurring revenue model, much like any Sass company would. And so they're often running they're doing extremely well. I think that there's a lot of potential to parrot that content against other type of content where you learn not only the context, you learn the actual vocabulary language within the context. So there's a lot of potential for that company. And again, this is an example of a company co founded by calm Ron and Diego Diego is from Colombia, comrades from the US, different perspectives, very diverse team, they are often running and once again, we have great investors around the table there, and very excited to be working with them as well. It struck me you know, as
Alexander Sarlin:you were talking about you bits and how they have this amazing distributed team. Internationally, slang has a similar story. They have employees in Colombia, Mexico, Brazil, us, Nigeria, Rwanda, they have multiple offices in different continents. And it feels like this is a really exciting and interesting trend in edtech, where because you're working with international markets, you actually really walk the walk and have employees who are on the ground, localizing who understand each regional market. It's not from the hub in one country, it spreads to everywhere else in the world. There's actually a much more empathetic close up view of how to make sense of this. How to make sense of education, understand what students and companies want. I wanted to ask you a little bit more about your thesis for the roleplay portfolio. You mentioned at the outset of the interview about human enablement, which is a term I think you coined includes skills development, access to fulfilling work for everyone. And in particularly in this moment, also, you know, the improvement of remote work, because we have this international remote world. Give us a little bit of a rundown. I know you've already begun to speak about this about what you really mean by human enablement. I know you've thought a ton about it and where you sort of see the future work or the working world moving over the next few years that ad tech investors or ad tech founders might really want to keep their eye on.
Sergio Monsalve:That's a great question. I'd say I thought a lot about this over the many years. And also, a lot of it has been fueled by my own experiences. But human enablement at its core right now is a term that I don't think will ever go away. In fact, we trademarked the term, it's part of roadway ventures that will always be part of roadway ventures. Because I believe that if we are not enabling humans, then we have bigger problems to deal with. So I don't think it's one that will go out of style anytime soon, and hopefully never. But what it means for now and fund what I'll tell you what it means now is, I am very focused on enabling humans from a socio economic perspective, what that means is three things that I can describe as the three pillars. The broader definition, we Why think is very malleable and expandable. Is that to enable humans, to me down the road, it means truly thinking about humans from a 360 degree view perspective. So you can imagine that it's not just about their wallet and their socio economic mobility. It's also about their wellness, it's also about their health. It's also about their ability to thrive and be happy right. Now, that's not part of the theme right now. But this is not just a one and done fun. This is a movement. This is a firm that will outlast me, hopefully, down the many, many decades, hopefully. So I do think that the premise of Robledo Ventures is that first and foremost, venture capital should be mission driven. It shouldn't just be about capital, it should be about just like entrepreneurs pour their heart out to develop something for their customers, venture capitalist should stamp or something. In my case, I'm about standing for human enablement that includes a broader population, not just the people that I've gotten to rub elbows with, because I happen to have gotten into Stanford and Harvard and all these places that are pretty cool places, but they're pretty exclusive places, by definition. So I am all about including as many people as possible. And where I live, I mean, we have a freeway called 101. And we have the East a one a one and the West 101. In the east, a 101 has not fared so well, in the last two years, the west of 101, has fared incredibly well, to me, that dichotomy is just shouldn't happen, we should be enabling technology for the East and the West to thrive. So that's in the premise of human enablement. How we exercise that in fund one is three buckets. One is what I call workplace transparency. Meritocracy is remote work. That bucket is all about enterprise software and SaaS companies. You could call it a subset of the cloud, very application layer software that's both enterprise to consumer, most likely, it will be mostly enterprise and data companies. Obviously, some of them may leverage AI, but it's not necessarily AI focused. So these are application layer software companies that like adaptive did in the financial world where if they offer transparency to the broader workplace, I'm investing in companies that, for example, offer transparency and compensation, remove bias in compensation, which is, to me the epicenter of the glass ceiling, right. So how do you break the glass ceiling in a corporation is through transparency, and through education to so those companies like compass, like bright reps are really moving the needle on that ability to create a flatter organization, more meritocratic, remove favoritism and nepotism. And then create much more mobility in the marketplace in the workplace. Number two is skills development, that's the second bucket. And that's where your edtech and your lifelong learning fits. And that's where Udemy would fit in, right, or Kahoot. These are companies that essentially are creating systems and platforms that enable for people that want to learn new skills and upskill themselves to get ahead. But this also means that we need to include, for example, roadmap, companies that allow you to pair up what you know, to what jobs you can do. There's a lot of also software as a service components to it. But there's also consumer companies content companies in the education space. And then the last piece, the last bucket is essentially job creators. And those take the form of marketplaces, because the supply side of marketplaces create new types of jobs, but I'm not looking at jobs that are just driving a car delivering food, I'm looking at platforms that create aspirational jobs, also jobs that access a different type of the population. I learned this early in my eBay days, where a lot of our power sellers were people that were making 100% of their household income where they're making it by selling their goods on eBay out of their garage. But the reason that we're doing that is because they couldn't go to a nine to five job at and so we alienate A lot of people when we make them work in a job that is very rigid, because they may have kids at home, they may have a handicap or they may not be able to get there, they may not have transportation. So we want to be much more inclusive about how people make their money and feed their family. And so the two sided marketplaces are a great way to do it, like we've done in Udemy, where instructors are now being treated like heroes, while in real life, we don't really treat instructors, teachers like heroes. In fact, it's probably one of the least revered from a monetary perspective, less compensated profession in most important profession. So I think at UW, we've been able to break through and pay them like they deserve, which is to be heroes of our society. So I think in the last bucket, I'm looking at platforms and systems that allow for better type of employment and an economic a viable economic avenue for them to work outside of your standard status quo world of nine to five office job, right. So I think that there's many ways now that you can make a living, especially on aspirational, living, things that can make you 10s of 1000s of perhaps even hundreds of 1000s, or, in the case of Udemy, even billions of dollars a year, just working through that platform.
Alexander Sarlin:We spoke on a recent podcast about how the top teacher on teachable, made $10 million on that platform, and she was an assistant principal at a school and then became incredibly wealthy through that, through her work in that kind of marketplace economy is really interesting to see that kind of dynamic playing out. Wow,
Sergio Monsalve:that's great. Yeah.
Alexander Sarlin:I have one more question for you. It's a little bit of a curveball one. So I'd love to make sure it makes sense. So the three themes of human enablement you just mentioned, the first is almost b2b enterprise productivity tools, or more various types of SAS tools. And the other two are things much more familiar to our audience, the skills development for K 12 and adult learners, and the idea of marketplaces that can provide new jobs or empower teachers or power sellers of various ways. The first one is one that we almost never talked about on this show this idea of how do you have companies that work within the corporate structure, but actually improve the world in various ways like salary transparency, you know, some of the tools in your portfolio dragon boat are some of the companies dragon boat is a product management strategy tool. They have planning tools like mosaic team building tools, like rising team, and you mentioned adaptive insights, which was purchased by workday in 2018. It's another cloud based sort of planning tool. So how do you see those modern really sort of cutting edge thoughtful corporate enterprise tools, dovetailing with some of the other companies or the other themes that you've mentioned? Is there a way to empower learners, whether they're K 12, higher ed, or just entering the workforce, to enter a workforce that has tools that make their lives better and easier and more interesting and more fulfilling? How do they work together?
Sergio Monsalve:Yeah, there's a ton. I mean, I could tell you examples of companies that I wouldn't know where to bucket them in those three buckets. In some cases, I would bucket them and all three, in some cases in two. So I think there's incredible synergies between the three. And ultimately, the umbrella is human enablement, currently defined as socio economic enablement. And in the future, it could be a broader definition. But right now, I give you an example of a great company, great founder CEO, who said second time CEO, I've had the fortune of funding her twice, Jennifer Dulski, ad rising team. That's a great example of a company that fits into two buckets, at least, if not three, because what they're looking to do is to enable a system so that you could actually help teams be better trained, right? in a corporate environment, or in a enterprise environment, you need teams to be create a good chemistry, creating a good working environment, create better communications, be high efficiency teams, right? High performance teams are hard to train, because it's all about there's a lot of human interaction and chemistry and human idiosyncrasies that come into play. But Jennifer has a playbook that she's building. And she is now going to launch two companies that want to make managers and team members much more efficient, right. So you can imagine that one could fit in the first bucket, it could fit in the second bucket because it's also very much about skills development. And then third bucket because it could have this component where the trainers could be on the supply side and the trainees could be on the demand side now. There could be an evolution of the company as she matures. There could be so many iterations, but I could see that company being a full human in a will mean company along all three dimensions. So that's a good example of one. But there's many in the portfolio that fit into at least two to three buckets. Ultimately, I think the goal is to be inclusive. And to bring a lot more people into the goodness of technology, letting them experience the socio economic goodness of what technology can do for them and for their families. And to me, that also allows me to sort of have a mission. And I do think that the next generation of entrepreneurs, and hopefully the next generation of venture capitalists will want to do well financially. But we'll also want to do good by standing for something, and in my case, is going to be human enablement. So I feel like, I can address that very authentically, especially given my whole background and sort of my immigrant first gen background, I think it's important to be empathetic to that. And especially, it's important for an investor to have been in the shoes of an entrepreneur, like I've been my past, hopefully, I can bring much more value to the entrepreneurs that I fund with discipline, because obviously, the other thing I was gonna mention is, when you're investing internationally, and investing in a lot of these different companies, there's a lot of risk. So that discipline is going to be incredibly important. One example is, I learned a long time ago, especially given where I came from, and the fact that I was in a firm that invests internationally that you have to be very careful about foreign exchange risks, country risks when you invest internationally. So that is not something that I take for granted. And I obviously bake in into everything that I think about when I do diligence.
Alexander Sarlin:Yeah, that's a terrific answer. And as you talk about it, you really can see how certain companies span multiple sides of the sector reminds me of how slang that we mentioned before can work for an individual looking to learn English for marketing or English for finance, a university can teach it, or a corporation can bring it in for their employees, and to facilitate cross cultural communication there. So the same company, the same tool can be used in multiple contexts. And somebody might encounter it as a high school student or a college student or on the job, and feels like Udemy has some of that as well. So it really does add up, we want to end with a couple of very quick questions that we ask every guest on the podcast. First is what is the most exciting trend you see in the EdTech landscape right now that our listeners should keep an eye on,
Sergio Monsalve:I do think, the most exciting trend and the biggest trend, you can approach it from trees to forest or forests to trees. So bottom micro to macro or macro to micro and I think it's important to look at it from both perspectives. I do think that we're living in edtech. In a world where majority of the learners in the world, it doesn't matter what age, I have to interact with something that doesn't talk back to you very effectively, which is called a book, or a magazine or, or something that is very inanimate, something that is not interactive. So I think the biggest movement that we're gonna see in education is that we are now in a place where we no longer have to interact with something that doesn't talk back to you is not fun, it's pretty much a dead object. We are now in a mode, where we are everything we do in education will be interactive, whether it's web three, which I very excited about, whether it's it encompasses some, by the way, some blockchain opportunities as well. I think overall, those are enabling technologies that in my world of application layer software, will essentially translate into a world where the learner no longer has to be in the room quiet, basically talking to a book or imagining what the book is telling them. It is now a world where you are in that full immersive environment to learn as much as you can.
Alexander Sarlin:That's really interesting, interactivity, immersive education everywhere. And our last question is, what is one book or it can be a blog, a newsletter, a Twitter feed, that you would recommend for people who want to dive deeper into some of the topics we discussed today?
Sergio Monsalve:I actually did away with books in my class. You know, I used to kind of offer a variety of books in my class at Stanford. But I do think that a lot of the books that I've read over time are especially this industry is moving so quickly, that I wouldn't necessarily recommend a book that is sort of subject matter specific. What I would recommend is just the tools that people need to really understand how to be a great entrepreneur. So I'll give you an example of a book that I think is highly important. And I mentioned it a little bit before as is how to you rack up your 10,000 hours to become an expert in something and that came out of Gladwell, his book, the outliers, it's an interesting framework to think about that, to be a great entrepreneur, you're gonna fail and succeed, fail and succeed and you're gonna go through many, many, many ups and downs. It is not until you actually rack up enough reps that you will have the pattern recognition and the ability for you to continuously be more on target more calibrated, you'll make better decisions, faster decisions. So I eat the notion of racking up those hours in those reps in the most efficient way, is a super interesting notion that I think that book provided. Absolutely. And as always,
Alexander Sarlin:we will put links to every resource we mentioned in the show notes for this episode so people can access them easily. Sergio Montsalvat this has been truly fascinating conversation. I learned a huge amount and I'm sure listeners did as well. Thank you for being here on Ed Tech insiders.
Sergio Monsalve:Thank you, Alex. Take care and thank you to everybody.
Alexander Sarlin:Thanks for listening to this episode of the Ed Tech insiders podcast. If you liked the episode, remember to subscribe on Spotify, Stitcher or wherever you get your podcasts. And if you're listening on Apple, please leave a rating and review so others can find the podcast. For more ed tech insiders content subscribe to the Ed Tech insiders newsletter at edtech insiders.substack.com