Shay David On Building A $1.8 Billion Business And Raising $34 Million To Leverage AI To Hire The Right People

Shay David, a seasoned tech entrepreneur with multiple exits, has had a remarkable journey through varied technological landscapes, from navigation to video to HR.

His story is a testament to his adaptability, strategic acumen, and commitment to leveraging technology for a positive impact on the world.

In a candid and insightful interview, Dr. Shay Davids shares his experiences, from growing up in Israel to co-founding successful companies and ultimately venturing into a neglected industry.

The conversation touches upon key lessons learned, the importance of time to market, and the evolution of technology.

Dr. Shay’s newest venture, Retrain.ai, has attracted funding from top-tier investors like Radical Ventures, Square Peg, Hetz Ventures, TechAviv, and 406 Ventures.

In this episode, you will learn:

• Dr. Shay David underscores the importance of timing to market, emphasizing that great technology requires synchronization with market needs for successful commercialization.
• Growing up in Israel during turbulent times shaped Dr. Shay’s focus on self-sufficiency and innovation, which later influenced his entrepreneurial journey.
• The success of Destinator Technologies highlighted the significance of understanding technological landscapes and developing solutions that address market challenges.
• Kaltura’s success demonstrated the transformative power of recognizing and addressing challenges in the emerging video revolution, reshaping how content is published, monetized, and measured.
• With Retrain.ai, Dr. Shay aims to use AI to empower people, create jobs, address the skills gap, and reshape the HR landscape to focus on skills rather than replace jobs.
• Dr. Shay advocates for strategic whiteboard meetings, emphasizing the need for entrepreneurs to understand market trends, competitive landscapes, and strategic differentiators.
• Driven by a vision where individuals own their skills passports, engage in lifelong learning, and organizations make informed decisions around skills, Dr. Shay’s Retrain.ai aims to revolutionize the future of work.

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About Dr. Shay David:

Dr. Shay David is a Co-Founder and serves as President, General Manager, Media and Telecom, and Board Member at Kaltura. He also serves as a Venture Partner at Emerge (VC).

Shay is also a Co-Founder and serves as Chief Executive Officer and Chairman at rRetrain.ai. He is a scholar and serial entrepreneur who specializes in collaborative and open-source information and communication systems.

Headquartered in NYC, with over 150,000 publishers, universities, and enterprises worldwide that have integrated Kaltura’s open-source video platform, the company is the world leader in the field.

At Kaltura, Shay oversees the company’s business unit, which focuses on the media and telecom industries. He is also a founding member of the Open Video Alliance, an organization dedicated to open standards for video.

Prior to Kaltura, Shay was a co-founder of several software startups and consulted on open systems for Fortune 500 companies like Toyota.

He holds a B.Sc. in Computer Science and a B.A. in Philosophy, Magna Cum Laude, from Tel-Aviv University and an M.A. from New York University, where his interdisciplinary research thesis focused on the political economy of free and open-source software and file-sharing networks.

Shay wrote his Ph.D. dissertation on “Participatory information networks” at Cornell University, and he is also a fellow at The Information Society Project at the Yale Law School, where he has done his post-doc work on issues of access to knowledge.

He has published extensively in leading academic and industry journals and has presented his work all over the world.

Connect with Dr. Shay David:

• Forbes
• LinkedIn
• Crunchbase
• PitchBook

Read the Full Transcription of the Interview:

Alejandro Cremades: Already hello everyone and welcome to the deal maker show. So today. We have a founder ah joining us you know from startup nation. You know we’re gonna be talking about his amazing journey. You know he’s right now building a rocket ship that thing we’re gonna be talking about. We’re gonna be talking about this in detail. Especially because he’s tackling a industry that has been completely neglected neglected. He has a multiple exits. You know he say taken several of his companies actually that he co-founded. You know went public and they we’re going to be talking a lot about time to market. You know perspectives especially when you’re thinking about utilizing the technology that you have available to you for the environment that maybe you know you have around you also going about integrations you know with with your business as well as you know with the you know people why people are so important you know to organizations and. And some of the lessons around that. So again, brace yourself for an episode that is going to be incredibly inspiring with our guest today Shay David welcome to the show.

Dr. Shay David: Um, thank you so much Fantastic to be here. Thank you.

Alejandro Cremades: So she so give us a walk through memory lane born and raised in Israel how was life growing up.

Dr. Shay David: Life growing up was ah interesting, especially now you know we’re being interviewed while Israel is fighting a war I was born in 1973 a very tumutious time in israeli military history. So growing up in Israel was actually surprisingly serene. You know, a lot of time spent outside a lot of time spent with our dog roaming around Israel in action and in actuality I think is much more serene and calm than you’d suggest ah from the news.

Alejandro Cremades: So how would you say that he shaped you up to the the fact that you’re that you know was working for the Israeli government. You know you guys you know were ah you know in and out of the us as well. I’m sure that that shaped a little bit to the worldview that you had right.

Dr. Shay David: Yeah I think I think so I think you know the old joke is that israelis woke up and realize that there’s nothing much around other than sand so. The only thing that they could do is hidetake silicone or rely on human ingenuity. So I think a lot of the eaters growing up was self-sufficiency. And the capability of being able to kind of make ourselves and and as a kid I actually got to travel to Silicon Valley when I was in elementary school and then later again in high schools I always had that contrast between life in Israel is a small country and life in Silicon Valley where technology was happening and that de. Helped me shape my own technology vision understanding how technology could be a force for good or a force for evil and being able to bring a lot of that technology back to Israel. It’s a good story I think that I went to elementary school and then I went to high school in Palo Alto

Alejandro Cremades: How did you get into computers by the way.

Dr. Shay David: So first in the 80 s and I just remember that you know to get an hour of a computer before before personal computers were actually personal. You had to book an hour at the library. So. My first experience with a personal computer was with a ti ninety nine one hour a week at the Palo Alta Public Library and but the computers didn’t have ah any recording device so you had to program your program type it in debug. It run it all within the course of an hour so that taught you a lesson about the efficiency and about writing code without too many bucks. Otherwise you wouldn’t get to run anything and that was a very strong memory that I took away. That you’re in Colorado.

Alejandro Cremades: So you studied the ultimately computer science in Tel Aviv but 1 thing that is really remarkable to me is that you’ve done quite a tour when it comes to american universities. You know you ended up doing your masters in New York University you also did a ph d in cornell.

Dr. Shay David: Are.

Alejandro Cremades: Then you did a postdog at Yale University and what’s going on with all these different universities and all these you know different degrees.

Dr. Shay David: I try to stay a student as long as they could and every time they kicked me out I had to go to another school. No I’m just kidding but I really appreciated American Academia and I always was hungry for more knowledge and and and mostly being surrounded with smart people. So. While starting companies and and being a serial of entrepreneurs that was always kind of a scholar in me and I truly did try to stay students for as long as I could and keep diving into knowledge my academic area of expertise is open information systems I did my pjcornet on open and collaborative information systems understanding things like Wikipedia and open source software. But there’s also a lot of examples from military history from open source biology really understanding how large groups of people come together to build large scale information systems and. Later I moved to my postover. Yeah, and where I studied access to knowledge and how all that knowledge is being put to good use with all its implication for law and policy etc so that was always in the background of of me being an active entrepreneur and building technology that was always the side of me. But really wanted to understand the impact of technology and kind of this very complex relationship between technology and society.

Alejandro Cremades: Well curiosity is definitely a pattern that you see on on some of those like super successful founders do is like they are eager to learn to find you know things to find new things and I mean in your case that’s ultimately what happened you know with your first venture mind echo. So. How did you get into the whole venture world. You know what was what was that and what did that look like for you. So.

Dr. Shay David: Um, so that was my first startup I was ah first a team lead and then I was on the business side and that was a company that developed collaborative filtering and recommendation systems. Um and within that company I was in charge of of developing some of the applications and then. Helping strike some of the deals and that was I joked that that was my business school I never went to business school but in that company I learned the most important lesson in technology businesses I think which is time to market the technology that that company Mandeck could develop was technology was. Able to recommend individual media tracks to people today. We kind of take that for granted because we have that on items and Netflix and whatnot. But we’re talking twenty five years ago that wasn’t taken for granted at all the challenge that the company had was that there was no market for selling individual media tracks the value of recommending media to people. Quite low and it was one of those companies where technology is looking for an application. It actually never found kind of a great outcome for that application. So that to me that is a lesson that stayed with me for the rest of my career which is you need to have great technology. Is ah a required condition. But it’s not always sufficient because timing to market is absolutely censship when commercializing technology like that, especially on the front end and on the bleeding edge of technology development.

Alejandro Cremades: Well as the saying goes to you know either succeed or you learn. So I guess say you know in this case it was I mean you guys ended up doing a transaction. You know you guys ended it up selling the ips. So I think there’s 2 things there that perhaps you learn one was the visibility into the full cycle of building a business you know from start to.

Dr. Shay David: Exactly.

Alejandro Cremades: Finish line and then number 2 is not achieving. Perhaps you know like that billion dollar you know, outcome that you had hoped for what was you know? Also the lesson that you took away from dealing with perhaps not the outcome that you had hoped for.

Dr. Shay David: I Think you know there’s always the stories about then entrepreneurs kind of getting up and brushing the dust and moving on. Ah the the metaphor that stuck in my mind all with is that the technology ecosystem is kind of like the coral reef.

Dr. Shay David: Waterf fish get eaten by bigger fish and and Debris falls to the ground but the ecosystem itself remains very lively and I think that when you have kind of an experience like that where you’re not getting the tremendous outcome you’re getting some outcome but you meet a lot of people along the way you learn important. You learn what works What doesn’t work that kind of ecosystem material to build your next startup and for me that was definitely kind of defining lessons saying okay I understand how the world works a little better than I did a few years ago and let me go at it again.

Alejandro Cremades: So let’s talk about going at it again because that was destinator technologies you know the next day idea venture that came knocking so how was that transition like you know for you.

Dr. Shay David: Great.

Dr. Shay David: So destinator was a very different business. It was a technology business and destinator which I started together with my good friend Ron was in the business of Gps navigation the limiting factor at the time was that um. There wasn’t a lot of communication that was able to get to the device. This was very early days of smart devices. Not even smartphones we’re talking about the you know the early versions of pun pilots and compact ipe there was no four g three g two g one g no communication to the device. So everything needed to be synchronized offline. And we realized that if you want to get Gps navigation in the physical handss of people or in cars that you had to have a lot of data on the device but the devices had very limited memory. We’re talking 64 makess not 64 gigs and the limiting factor was compression so desonator developed. Ah, proprietary compression technology. We call it the mpthree of navigation because just like mpthree it was lossy compression but it was specifically designed for these types of navigation application. It was good for fleet tracking. It was the forperson navigation in car navigation and what we were able to do. That technology is really unlock kind of the environmental potential of all these devices that we were were buying so people who would buy a Tod pilotlot and wanted to know what other things they could do with it. There wasn’t a lot that you could do with the panpilot as as and say taking notes.

Dr. Shay David: By being able to use our compression. You can turn a ponpilot into a navigation device that has a tremendous effect because now you could get navigation for probably less than half the cost that it would cost you to buy a dedicated Garmin device or or a dedicated hardware for that because you could reuse that cpu. Something good so that was a very important lesson for me in the sense that you have to understand the technological environment and what was going on. We knew that these devices are becoming ubiquitous. We knew that in order to use them for other application you needed the data and we understood that in order to get the data you need compression so by focusing on compression. All of a sudden a whole world of applications unlocked and there was the driver for the success of of dedemeter.

Alejandro Cremades: And obviously I mean what? Ah what a remarkable journey because also you guys ended up taking the company public you know and it reached the valuation. You know half a billion bucks so pretty remarkable. So I guess how was that. Experience tool of taking a company public I’m sure that was probably quite the experience.

Dr. Shay David: Yeah I think today you’d call that a spec deal. The company went public into into ah into a shell and was merged with a company that had complementary technology and that owned a lot of the private company that was a complex financial transaction but the business logic was very standard. The technology logic was very sound because. Those 2 companies worked together. There was fleet tracking and onboard navigation so you can have an end-to-end solution that was very valuable for large companies. So we ended up doing this with Lockheed Martin and with aser with Hp and the capability to basically bring that technology in an end-to-end. Integrated enterprise solution was very valuable and the company grew its revenue very rapidly and and was very successful in to invest.

Alejandro Cremades: So Obviously as the saying goes once an entrepreneur is an entrepreneur so it didn’t take long for you to ah to pull the trigger. Once again, you know in this case obviously. You know that transition was maybe easier because now you know you were going from a successful, very successful company that that you had you know helped to to be a cofounder there ultimately to starting a new one I’m sure that that next you know like turning the page and going to the next chapter was a little bit smoother. Than before you know what? Why would you say changed Then? why did you decide It was the right time to do so at that point so.

Dr. Shay David: So I I took a couple of years to finish my ph d and rest a little bit and kind of see what’s the next big trend and what I saw together again I continued with my very good friend Ron and 2 other amazing entrepreneurs Iran and Mikal. And what the 4 of us when we got together saw that the the world was changing again if initially when we started destinated. We saw that there would be some ubiquity of devices now we understood that the next thing that was happening was really the media revolution the iphone had just come out and all of a sudden. Ah, billion people had the means of production for videos in their pockets billion mobile cameras mobile video devices. A lot of screens multi billion devices kind of endpoints that could consume be doing it became apparent to us that there’s going to be this amazing opportunity. For being able to help control this video revolution and there weren’t really good systems there I don’t know if you remember the first days of video on the web. It was stuttering and if you shot something on one device. It didn’t work on another device and there would be cost and buffering and wasn’t very secure at all. And in fact. A lot of the stack which for the regular text-based internet was fairly developed at that point by being able to publish and measure and monetize all of a sudden all of that broke with video. How do you publish video. How do you monetize video? How do you measure the success video there then the opportunity to rebuild.

Dr. Shay David: Video stack and we understood that and early on when we started a company. We called it Kultura which were the words that kind of resonated with culture because we understood that the next iteration of culture was going to be in video humans are multimedia creatures and if a picture is worth this out than words then. 24 frames per second you do the mass. It became apparent that there’s going to be a huge opportunity in video and and that was kind of our our logicy for starting the company but we didn’t really know which part of the stack we were going to solve. Thought that maybe the original idea was that we’re going to allow people to post funny videos for competitions and maybe for collaboration and we had an iteration of the idea where we said that this was going to be kind of the Wikipedia for video where a lot of people are going to contribute small pieces of content for creating larger pieces of content. And it took a few iterations for us to understand that what really the world needed was a simple to use platform as a service video stack that could be plugged into the rest of the ecosystem and that could help organizations really utilize the power of video for everything they do. For inside use cases for outside use cases for enterprise learning and training and marketing for entertainment use cases for education purposes. Essentially we learned that video was an essential tool that intervened and and everything people did from the way they meet the way they study.

Dr. Shay David: The way they create the way they procreate etc and it was pretty apparent to us that anybody was going to own that stock is going to become a very valuable company.

Alejandro Cremades: So obviously the company became very valuable kultura you know again, you guys ended up taking the company public you know peak valuation of one point eight billion now 1 thing that is very interesting on this journey is that at 1 point you guys decide to bring senior. Talented management not to to really take the company to a new height at what point do you realize that and was that what what is that thought process because I mean ultimately as founders is hard to let go of the reins. You know of your baby and you know hand them over to someone else. So so how was that like for you guys? yeah.

Dr. Shay David: Yes I think for us it was about understanding that while you know, many entrepreneurs myself included like the syncos themselves most of the days as the smartest people in the room. Actually there are people that could probably do the job better than than you can, especially if you come as an entrepreneur and sometimes the the risk of that is that you might be jumping from industry to industry. There are dedicated professionals that are spending their entire careers within specific industries that once that creative spark is there. A lot of the growth of businesses is about the day-to-day providing value to customers day in and day out and net promoter scores and being able to do the integrations with the rest of the ecosystem and for us it was clear that if we really wanted to make an impact in this market if we want to build and sustain a multibillion dollar business that would have. Thousands of customers and hundreds of millions of dollars in revenue then we need to bring in a set of professionals that can help build that company from operations to finance to general management of the company’s divisions and we started a very orderly process of being able to find that talent and bring that talent. And sometimes that talent came from competition sometimes it came from customers that saw the technology and said oh if you can provide that value for me, you can probably provide it to others and I know how I can do that and etc etc.

Alejandro Cremades: So in 2020 obviously you realize that now the company is in good shape you know, ah being led by great people and obviously that frees up time but as a founder when time is available. You get the time to also dream.

Dr. Shay David: Are.

Alejandro Cremades: Now in your case when when when when that moment came you know and the the moment to dream came about what you realized was that people were ultimately the most important you know asset you know within organizations and that Hr had been neglected and that ultimately led you to start retrain.

Dr. Shay David: It’s.

Alejandro Cremades: Ai so what are you guys? ultimately doing at retrain dot ai and what’s the business model and how do you guys make money there. Yeah.

Dr. Shay David: So re return ai is a new company new team new investors even of some of the investors from katurra followed me because they wanted another run together with me so two. Amazing co-founders Abby and Isabel and Havi came from the israeli military many years. And building very large-scale state systems as the Cio City of israeli military intelligence and isabbel coming from hr tech with many years of experience in both building. Ah hr technology as well as financial and operational roles with other individuals within the israeli tech ecosystem. And together the 3 of us had this vision that the next big revolution that will happen and again I’m trying to implement my lessons about really understanding the bigger shifts that are happening in the technology landscape so we talked about mobility and we talked about video and the next big evolution was Ai every Ceo in the world. Wakes up to this thinking. How is ai going to disrupt my business for many of them the the solution to that equation is let me see how I can implement Ai in my business but what many ceos are beginning to realize is that the most neglected asset is their people so we came to this. Area with a different angle saying could we use Ai to empower people most Ai companies business then could be translated to how many jobs are you going to take away. It doesn’t matter whether you have a self-line drone or an automated ordering system in an airport cafe right? eventually most Ai takes people’s jobs away.

Dr. Shay David: We wanted to reverse that equation. We said what if we use Ai not to take away jobshua to create jobs to help organizations hire fasters retain longer develop their talent more intelligently and what we developed is we developed an hr copilot. It’s a natural language processing based system based on. Billions of data points that we train to really understand the labor market in the language of skills and it helps hr professionals and it helps hiring managers and it helps ceos and it helps sports really takes smart decisions in this cycle from hire to retire starting from pre-hire answering questions like. Who are the best candidates in my candidate pipelines that I should hire and where can I find more candidates like that then moving on to onboarding and talent management like which career path that that individual has and how could we put an individual in a career path that they’re doing their maximum enjoying themselves while contributing. Then moving on to strategic worksfor planning questions like what are the next things we should be hired for how do we stand against industry in terms of developing the skid that we need for the workforce of tomorrow for kind of the future work fellow division of the company. We’ve been building it for last three years some very large. Companies around the world are using it to help them take ah hr ah decisions day-to day and the outcome of that is that we have an Ai that helps create jobs rather than taking jobs away that helps people find meaningful employment and that helps really find the skills gap which is probably 1 of the largest problems affecting the world right now.

Dr. Shay David: If you read the headlines in say the New York Times economics sections you would think that ai is going to take everybody’s jobs the data shows otherwise the data shows that the biggest problem the market has right now is not lack of jobs. It’s lack of skid labor that could do those jobs. It’s people that can work. With twenty first century skills with the machines in order to help organizations do their maximal and that’s exactly what we’re focusing on using Ai in order to help find the best people keep them for longer train them and develop them more intelligently so that both the individual and organization wins. But being able to focus on those twenty first century skips

Alejandro Cremades: Now in this case, you guys have also raised some money as you were alluding to it earlier. How much capital have you guys raised late. So.

Dr. Shay David: Um, so the company had announced $34000000 of funding led most recently by radical ventures scorpeg ventures and before that with ah Tek Aviv heads and point 4 or 6 so really tremendous investors. Very happy to have those guys on board. We tried to have every board meeting to actually be a white board meeting and we’re very lucky to have ah very smart money around the tape I think that you know one of the things that you want to surround yourself with.

Alejandro Cremades: What do you mean with white board meeting.

Dr. Shay David: Good people That’s true for the people that you hire, but it’s also very important on the investors so you want the board meetings to really s sink strategically and I’ve seen too many boards from companies say I invest in or boards I participated in where embra is just focused on the numbers of the last quarter. But in some sense the numbers of the last 4 are almost not interesting because who guarantees to you that the next word is going to be good. It’s going to be good only if you understand the bigger Market trains and that’s what I mean by whiteboard Meanings by being really able to understand how do you play to your strings. How is the technology that we’re developing going to make a lot of money by being given mostly to provide a lot of value. What are the big industry Jaggernauts doing Why wouldn’t they squash us and develop it internally who’s going to buy this business eventually or is it going to be big enough to develop its own. Financial metrics so they could go public. That’s what I mean by whiteboard. You need to have a game plan and you need to understand that you know we’re not building a charity. We’re building a business who’s going to buy our technology who’s going to license us our technology. What’s a strategic differentiator and how does this all play out in the face of. Competition in most markets.

Alejandro Cremades: So obviously when you raise money from from sophisticated players. You know you need a vision and you need a vision not only for them but then also for employees and then also for customers so talking about vision here if you were to let’s say go to sleep tonight.

Dr. Shay David: Are.

Dr. Shay David: Are the.

Alejandro Cremades: And you wake up in a world where the vision of retrained or Ai is fully realized what does that world look like.

Dr. Shay David: So I think they were um I actually brought my future work t-shirt for the podcast and so in our vision for the future work. It’s a world where people are focused on skills and when I talk about scheme that talk about skills with capitalists which is people. Or or employees in this case are participatory in their career development. They understand that every job that they do is a learning opportunity and they own their skills wallet or skills passport and at every given point in time they understand that they need to learn because people entering the ort force today are probably going to have 10 to 15 different jobs. Potentially completely shifting careers at the turn of the of the twentieth century almost 50% of the us population worked in agriculture today less than 3% of them work in agriculture that doesn’t mean that 47% of the people became unemployed it means that 47% of the people are working in professions that within no. Existed the old joke about the jewish grandmothers that wants her grandkids 1 of them to be a lawyer and the other one to be a doctor right? Very few jewish grandmothers and I know one of their and grandkids to become full stack developers even though full stack developers in the reality of twin 23 is probably. 1 of the best paying jobs. So in our vision the world that we see for the future work is a world that is focused on skills and gives individuals the capacity for lifelong learning to continue in developing their skills and gives organizations the capacity to take decisions from hired to retire around skills.

Dr. Shay David: So that they can find the tan that they need develop the skills that they need and make individuals more engaged and more productive at the same time and I think we’re getting pretty close to that vision using system like ours and and still have other startups that are developing kind of that future work and 1 things that happened in the last few years and especially. Kind of during covid and after covid is this idea that the future work is here Mckinsey talked about a 15 year horizon for that and covid actually compressed that with a lot of new technologies coming in the Ai revolution remote work flexible work dramatic shifts in the labor market. Which are being accelerated. So I think we’re getting very close to that vision every day.

Alejandro Cremades: Now imagine if you were ah now to go into a time machine and let’s say you know you’re able to go back in time you know maybe to that moment where you were about to think about starting mine echo and you had the opportunity of having a chat with that younger shay and. And give that younger shay 1 piece of advice for launching the business. You know what would that be and why given what you know now.

Dr. Shay David: I would say focus on customer value right? understand who your customer is how do you provide value to them and how does that value translate into your main business driver who’s going to pay for what and. You know that could all all those more complicated questions could be translated into 2 simple questions to ask that future self in an interaction with the customer to is ask your would be customer in the following which is what could you do with my product that you couldn’t do without it. And what could you do with my product that you couldn’t do with the competition and if you do not have a very clear answer to both of those questions don’t develop the product I wouldn’t today what I know today I would tell my my younger shy don’t write a single line of code until you have a. Crystal clear answer to both of those questions.

Alejandro Cremades: I Love it So shay for the people that are listening that will love to reach out and say hi. What is the best way for them to do so okay.

Dr. Shay David: So the best way is find me on is our Linkedin and Dr Schdavi or retrain a I so that’s ws ww w dot retrain dot ai or shy dot David S H A Y Dot D a v I d at retrain.

Alejandro Cremades: Amazing, well easy enough. We hey thank you so much for being on the deal maker show today. It has been another to have you with us. Yeah.

Dr. Shay David: But Ai.

Dr. Shay David: Thank you so much and it’s a pleasure to be here I’m a big fan.

*****

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