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Intro: We really changed the way that our organizations think about how they do learning and taking it away from being one single, individual’s role they hate to being a thing everybody can contribute to in how they build and create really effective educational teachings and trainings. Sasha: Brett, where are you joining us from today? Brett: I am here in Hawaii right now. I’ve been living here for most of this year. At the end of this month, I am celebrating with my parents visiting, showing them to Hawaii for their first time, and then after that, I am actually moving back to the Bay. Sasha: Nice. Did you just head there for the pandemic?Brett: Yeah, I came out here last Christmas basically and just stayed here. It was way better to be here than it was to be in the Bay during most of the pandemic. I’ve spent a lot of time here. It’s been really nice, and I am also itching to get back to a lot of my friends over there, my network, and a lot of the available activities and climbing gyms, also just to have a home that feels like a good long-term home to settle back into and do some nesting. Sasha: Yeah, that’s fantastic. I actually had a similar idea. I was living in the Bay where Coronavirus hit, ended up moving to Tahoe for six months, and then just about a month ago, very similar to you, was feeling I’ve been everywhere. I’ve been moving all around. It is time to get to a stable place. I just moved back to Menlo Park the start of this month, very recently. Are you from the Bay originally?Brett: No, I grew up in Cleveland. I was there for my whole life and then in early adulthood I moved out, went nomadic, location independent. I lived in Mexico for a while and got really into skydiving, paragliding and base jumping, air sports. I traveled a lot for those and spent up to three months at a time, tourist visa length essentially, in a lot of places like South Africa, Turkey, Switzerland, a lot of trips to places like Norway, Iran, Malaysia, China, the Arctic. Sasha: That’s amazing. Brett: I just did that for a long time running this business as a freelance operation for most of that time and then eventually it just grew. It turned into a real company. I was bewildered to one day wake up and be like wait, how did this happen. Sasha: My company is a real thing. I did a little bit of traveling as well. I lived in South Africa for about three months while I was in college, Brazil for about three months, and then I did a year in Ireland. I was on a George Mitchell scholarship, but I also got a chance to play some professional basketball. I definitely understand the nomadic life as well as the world of working on a side project that then slowly grows into a thing that’s suddenly big and real. I am very fortunate to say I got to actually create a company out of this. Brett: Exactly. This has been so far a pretty good intro and I would love to get into this more, but before I do, I want to talk to our audience a little bit about who you are and to briefly introduce you. Everybody, this is Sasha Seymore. He is the co-founder and COO of Learn to Win. Learn to Win is a mobile first learning management system, and as we just started discussing, Sasha, in addition to being co-founder and COO of Learn to Win, he was a Stanford MBA and a former Naval intelligence officer and McKinsey consultant. He was a walk-on basketball player at UNC Chapel Hill and played pro ball in the Irish pro league. Interesting, can you talk a little bit more about that? Sasha: I am originally from North Carolina. I was actually a soccer player growing up. I think I mentioned briefly before that my grandfather had been an All-American soccer player at Cleveland State University, which at the time was Finn, and I was heads down focused on that. Then in high school, I hit a pretty major growth spurt and I became this quasi, awkward half soccer player, half basketball player but was fortunate in high school to earn a really prestigious scholarship to go study at the University of North Carolina, called the Morehead Cain. I got UNC, discovered they had a JV team, played on that my first two years at North Carolina and then my senior year got to walk on to the varsity team. As a relatively average sized kid growing up, from a small town in eastern North Carolina, I always probably had dreams of playing basketball at North Carolina but certainly never thought it would be a reality. I was fortunate in the way life events worked out such that I got that chance. That was a really phenomenal experience. I’ll go into the Ireland piece a little bit. I actually was in Ireland for a totally different reason. In college, I had been really involved in sports as a method of conflict transformation and sports as a method of conflict resolution. It is a bit of a longer story, but I kicked a soccer ball across the state of North Carolina and basically helped found an organization that used soccer and used sports as a method for bringing people together in countries and in places where they would have been divided by conflict or other sorts of reasons. I was going to Northern Ireland on what’s called a George Mitchell scholarship, a fully funded scholarship to Ireland. I was one of 12 Americans selected to go over, and I was basically doing a Master’s in conflict transformation and social justice at Queen's University Belfast in Northern Ireland, dual studying and getting my master’s degree while also working in the community helping to use sports and basketball as a method to help bring communities together Catholic Republican backgrounds and British Protestant backgrounds. While I was there, basically one of the local pro teams, I don’t remember if I reached out or they reached out, but I got a chance to play with them for a year, which was a ton of fun. Brett: This is fascinating. You just said a whole lot there I would love to double click on and unpack. One of them we could just put a bookmark on is kicking a soccer ball across North Carolina, but the thing I am really interested in right now is the idea of sports development as conflict resolution. When I think of sports and conflict, I imagine within a team you might have conflicts and you work to resolve those conflicts so you can have a cohesive team. That’s just the whole idea of teamwork. That’s the metaphor we often bring into business with teamwork. Also, what I perceived to see in sports is that between teams and between fandoms of teams, you end up just having increased conflict. In the United States, football teams and basketball teams, it is like a friendly rivalry and friendly conflict. There’s a way that can create a cultural cohesion. Then you look at soccer or what other people call football in the world, and you see stadiums being torn down and riots after major games. I am curious how you approach this if you are going into a group of people. You mentioned Republicans. You were talking about political groups. Sasha: I wasn’t talking about the US Republicans and Democrats and the way you might understand it. I was talking about people in Northern Ireland and specifically those who want Northern Ireland to be a part of Ireland versus people who would like to remain a part of the United Kingdom. There are two different groups there, and they have historically fought. Brett: How does that work? How did you approach using sports to bridge that conflict?Sasha: I think for me the history of it is just experiences I had growing up and I think realizing the kinds of bonds and experiences I could build with people who weren’t like me using the game of soccer or using the game of basketball. I think in many ways athletics transcends this idea of class and the idea of race. It transcends even language barriers. My freshman year at North Carolina, I played on the club soccer team, and my two best friends that I made throughout the program there. I am a Christian and the two best friends I made I actually made through club soccer and playing pickup soccer. I am Christian, and then Dillan is Jewish, and Ahmed was Muslim. The three of us were just sitting around talking one day about the power of this idea that we had come together through athletics to become really good friends and had transcended those cultural barriers through the game of soccer. We were talking about it, and we ended up just finding a website, googling it, and finding a group that worked in the Middle East Palestine area under this idea if a Christian passing to a Jewish person, passing to a Muslim person, but a teammate passing to a teammate. That idea that you talked about a little bit before of if you have got to go through conflict together, if you have got to work together on a team to get a ball into a hoop, that helps to break down barriers and create understanding in a place that you might not be able to communicate otherwise. We got really fired up by the group and the work they were doing. We ended up deciding to dribble a soccer ball across the state of North Carolina the summer after our freshman year. It was about 350 miles we kicked across the state. It was a tremendous experience. I learned a ton about myself. I learned a ton about people who were from Jewish backgrounds and Muslim backgrounds. We got to talk with community members across the entire state of North Carolina. People opened up their homes to let us stay there or speak at the local churches, synagogues or mosques. That theme continued throughout the course of my career at North Carolina, my undergraduate career, and then I ended up going to Northern Ireland to study on the George Mitchell scholarship to continue pursuing some of that work that I had been doing. In sort of a Belfast context, the example I would give is there is an organization called Peace Players. They use basketball specifically, but the way that organization works is very similar to the group that I described where if you are playing soccer and you have got a Christian person who passes to Jewish person and passes to a Muslim person, it is not there but rather a teammate passing to a teammate. They do a very similar thing, but with people from two different sides of the conflict spectrum in Northern Ireland. They do it with basketball. It is usually with children at a younger age who haven’t necessarily formed a lot of these preconceived notions of what the other side might look like yet. I did that for a bit of time, and it was a fantastic experience. I am a big supporter of it. Brett: Yeah, absolutely. How did you find yourself in the position you are in now, founding a learning management company? How is that similar to the team kicking a soccer ball across North Carolina? How are you bringing all of this experience into what you are doing now? How did you find yourself there?Sasha: It is a great question. For a little bit of background, it is a parallel story but not everything touches in the same place. I mentioned before that in my senior year I got a chance to walk on to the men’s basketball team at Chapel Hill. When I joined, it was a childhood dream come true. It was an amazing experience. I was so excited. I also struggled a little bit initially learning our playbook. I am not the smartest of the players, and so I was a little bit behind sometimes trying to figure out what was going on. My roommate at the time, Andrew, had been really working on flipping some of the ways traditional college instruction was done at Chapel Hill. He had basically worked with Professor Hogan, Dr. Kelly Hogan, on changing the ways they were teaching some introductory STEM courses away from the traditional model of classroom learning that most of us might have grown up with, which is I am a professor. I get up and talk for an hour. I lecture at someone. You frantically write down notes, and then you are tested on it in two to three weeks. Instead changing it to much more of a blended learning and a flipped classroom model where basically you get a little bit of information but then you go do a quiz question on it or you get a little bit of information and then you have got to work on it in a group or a pierce heading. The idea behind it is the three core pillars around the instruction, which is structure, engagement, like forcing people to engage, and then feedback and evaluation. You are always testing, always seeing what people know, always trying to figure out if people actually understand this material. Let’s teach the things they don’t know. Andrew and I were talking about this in our dorm room as seniors in undergrad, and we said what if we could take some of the best practices and education pedagogy Andrew was trying to develop at North Carolina for our college instruction and bring them to the world of athletics. What if we could take that background and bring it to athletic teams, football teams and basketball teams? What if we could basically create an education platform that would build some of those education practices of structure, engagement, and continuous feedback into the teaching plans of any football coach or basketball coach? The idea was to create almost a three-pronged platform on the one side and almost like a Rosetta Stone or a Duolingo type of learning interface, something that would be available on somebody’s cell phone, highly engaging. They would get a quick video of a play, and then they would have to draw with their finger the route they needed to take, or they would get a video of a play and they would have to film themselves talking through what they needed to do. But then an authoring side that made it really easy for any sort of coach or instructor or teacher that may not necessarily be the most tech savvy or an expert in education pedagogy but could basically build and design lessons that all followed this structure, engagement, feedback structure as easily as they might create a PowerPoint or their traditional physical playbook. Then with an analytics suite that allowed you to see here we sent out a quiz and here’s the information we are seeing on what people are getting right or wrong. Now in terms of shifting our game place for this week, we are going to teach this thing, this thing and this thing, and really fill the knowledge gaps of what our players are understanding. That was the original concept of the idea. It was our senior year at North Carolina. We had it and thought it was really exciting. The two of us, I graduated and went to Ireland for the year on the Mitchell Scholarship and to play the year of professional basketball and then went to McKinsey and Company for two years. Andrew went to work for the African Leadership University, which is a series of tertiary universities in Sub-Saharan Africa. Then he and I came back, and we actually reunited at the Stanford Graduate School of Business. While we were there, we said we have been talking about this idea long enough. We really think it has got some traction. Let’s go do it. Essentially we founded the company while at Stanford and originally focused it on athletic programs. We had a ton of success there. It has grown to about 150 different athletic programs. But as we were building and creating the tool, we realized that what we were creating wasn’t necessarily just solving a problem that was specific to athletic programs but was really solving a human learning program. What we saw is there were tons of different organizations that had similar types of problems to what we were solving for athletic programs, and it is basically a term that I call the last mile learning problem. This may require a little bit of academic background. Stay with me here. In an educational world, there are two different ways you can classify knowledge. There are a bunch of different ways, but the two that we look at is foundational knowledge, which is foundational and everybody needs to know it. Then there is specific knowledge to a particular organization that we call our last mile learning that really is what drives a lot of their performance. I give a few examples of this. One example might be for a football team, all of the foundational knowledge you would need to know is everything you might have learned in Pop Warner football. Here is how the rules work. Here’s how you throw a football. Here’s how you block. Here’s how to tackle. There are tons of resources to do foundational knowledge because it is ubiquitous across a lot of things in a similar way there are tons of resources for doing this, Udemy, Coursera, LinkedIn Learning. All of those provide a ton of basically foundational knowledge for organizations and the military. What Learn to Win provides is that last mile learning. We made it just super, super easy for a football coach to take their playbook and teach that last mile learning, what their playbook is, in a really pedagogically effective way. We made it really easy for a business to take the way that they teach that sort of last mile material, which is at the moment currently sitting in the brains of some line expert, but basically learning and development hasn’t had a chance to keep up with the speed at which that changes and allow them to build and create their own pedagogically effective material as easily as they are probably currently doing creating a PowerPoint or creating a physical, email or sheet of paper to teach these kinds of things. I’ll step back a little bit. In terms of the chronological history of Learn to Win, to go back to the chronological story, it started in athletics. We realized our tool could be used in a wide plethora of different places. Then, we shifted to start working with the US Department of Defense. You mentioned before my Navy background. I am not a former intelligence officer. I am a current Reservist. I was basically realizing that a lot of the work I was doing with the US Navy and a lot of the training I was doing could be really improved by a tool like Learn to Win. We ended up taking a class at Stanford called Hacking for Defense where the DoD takes problems that the US DoD faces, gives them to Stanford students and tells them to go solve those problems. We basically ended up partnering with the US Air Combat Command on a problem they were having with the U2 planes and basically doing emergency procedures trainings with the U2. We shifted and adapted our platform to fit what they needed, and then two months after the class ended, we signed a contract with the Air Force. From that point on, we have scaled up to about 30 different partners across the Navy doing training, smaller partnerships with the Marine Corp and another one just kicking off with Space Force. As a part of that, I have actually invested pretty significantly into cyber security. We are actually the only mobile learning platform right now that has basically US Department of Defense cyber security clearance up to file six secret. Brett: Please, let’s improve that. Help. Sasha: In that vein, we have also started working with some larger enterprise businesses as well. Again, mostly in the vein of what I described before, helping them serve their last mile training. Examples would be helping to train drive-thru employees at Chick Fil A or sales team members on what their competitor’s product is and what they should be talking about with their own personal product or training manufacturing companies on the correct way to install this widget versus that widget, things in that vein. It has been a tremendous journey so far. We raised venture capital from Norris Venture Partners and their managing partner Jeff Crow and have grown the team pretty significantly. We have brought in world class leaders from Silicon Valley veterans to learning experts to people who are experts in sales, in the government space to really talented engineers across Facebook, Amazon, and Microsoft. We have really built something that we feel is changing the way, especially for this last mile place, people think about training and learning. Instead of it being a thing that is boring or not fun or takes a ton of time to create, we really changed the way that our organizations think about how they do learning and taking it away from being one single, individual’s role that they hate to being a thing everybody can contribute to in how they build and create really effective educational teachings and trainings. Earlier you called us an LMS, and I didn’t say anything. I winced a little bit because we don’t necessarily use that term. It is fine. We can be classified there, but we usually partner with somebody’s LMS. I don’t even know what we would call ourselves, but generally not an LMS. Brett: I like the last mile. Unfortunately, that’s also LM. Sasha: Last mile learning, I don’t know. Brett: It is really interesting there that you had this interface between government and private sector work. I have seen that before, and there are always a lot of really interesting lessons to transfer from one to the other, how those sectors can interact and just how different they are to deal with and interact with as customers. Can you talk a little bit about that experience?Sasha: Absolutely. I think I will probably start a little bit with why we even chose the federal government as a market in the first place and why the Department of Defense is a market in the first place when at least in Silicon Valley terms, most of the times when you hear early-stage startup going to pursue the government, people look at you with a side eye glance of are you insane. To give a little bit of context, again, like career and background as a Reservist in the US Navy, there is currently a shift in the United States’ focus from a military and geopolitical perspective away from not near peer conflict, so hunting terrorists, Al Qaeda, ISIS in Afghanistan and Iraq and shifting our focus much more heavily towards great power conflict and near peer competitors like Russia and China, specifically China. As a result of that, a huge part of the focus from a US military perspective, if it hasn’t happened yet, it needs to shift much more away from this idea of if we have these particular tanks on the ground that we can use to hunt terrorists towards how we build software systems that can compete with the Chinese. How do we build advanced technology that can compete with the Chinese? How can we basically build systems that are going to allow the United States to remain the preeminent global superpower and that the neoliberal idea of democracy, of human rights, of the freedoms we enjoy each day is the preeminent view around the world globally and culturally? I mean if you have read Xi Jinping’s vision of what a future global world order he envisions is, it doesn’t look like that at all. The treatment of Uyghurs today in concentration camps in western China is certainly not Holocaust level, it is probably as close as you can get in the year 2021. I think it is imperative that the United States do something about this, and as a part of that, the government has realized that they need to figure out how they do contracting work with Silicon Valley and how they do contracting work with technology companies that are based in the Bay area. There has been this sort of innovator push throughout the DoD of ways they can figure out how to do contracting better, ways they can support startups better, ways they can help foster this ecosystem of innovative ideas within Silicon Valley that can really help the United States to continue to maintain our edge against China. Learn to Win, as a company that is designed to help elite performers and elite competitors, especially with our work with athletic teams, felt that that was a great opportunity for us as a company, both in terms of all the similarities we saw between high performing athletic programs and groups and units with the Department of Defense but also a huge market opportunity in terms of the ways the DoD was shifting away from some of the larger primes to these more innovative startup ecosystems and a way we could do a service that a lot of people in our company and our organization really care about. That was the initial idea of why even pursue it in the first place, but you are right. There are huge differences in the ways that the government procures software and the ways that commercial enterprises procure software. To be honest, the government, there are pockets that get it and then there are a lot of other places where government systems are set up to purchase software in the same way you might purchase a tank. You buy one tank, and then you don’t have to buy another tank for 15 years. Whereas enterprise software is a recurring model where you have to purchase it every single year, and it is on a per user license fee, and these are all things that are very standard in the commercial world because it has moved forward faster. The government hasn’t done that yet. There are also still challenges and other things that you have to maneuver around if this new administration comes in, and they care less about this. This group came in and they care more about this. Funding shifts and moves regardless of the value you are providing to your end customer. That happens in the commercial space some, but it is generally less political. For us, as we have been building our business, we have thought about it in two different ways. One, we wanted to bring in real experts on the federal side. We hired a VP of government markets who has been selling into the federal space since longer than I have been alive. He used to be the former head of federal for Skillsoft, so really understands the space, understands how contracts work, understands how the backend relationships work. That’s been a huge benefit to my co-founder, Andrew, and I as we have continued to pursue that opportunity. We have made a dual push and a dual focus of wanting to build up our commercial business at the same speed and same rate we have been building up our federal business with this idea of if we get caught in some weird government budgeting cycle, we will still have our growing, thriving commercial business to work with as well. But let’s not miss out on this opportunity we have in the federal space given all of the amazing work that we have already done in that space, all of the incredible partners we have already, our cybersecurity requirement that we checked off, which was certainly not easy for us to get as a smaller tech company, and this new wave that we really do believe is coming of basically the federal government and the Department of Defense learning how to work differently with Silicon Valley tech companies. Brett: I think that’s happening across the entire government figuring out how to work, even in terms of how to handle transitioning licenses across state lines for licensed professionals. So many of these different things, but I think we could talk about that for our hours. We are getting close to our time, so I just want to close with one brief question. From your experience in using sports to grow through conflict, what’s one thing that you have brought into managing your team and leading the people within your company?Sasha: That’s a great question. I think there are two lessons from it that I will talk a little bit about. I think the first one is just I didn’t realize how much leading a company feels and acts and reminds me of being an athletics coach. When you are an elite level basketball coach, you can’t dunk the ball into the hoop. You can’t cross somebody up and make the pass. What your role is is to recruit the right players onto the team, put those players in a position to succeed, set the strategy and vision of what we are going to go do, and then get out of the way so your hoopers can ball. That one, two, three, four is almost identical to what I do on a day-to-day basis as somebody who is founding and leading a company. A, you have got to recruit five stars. You bring in really, really good people. B, you put them in the right positions to succeed. You make sure that your point guards are playing point and they are not playing center. C, you come up with a game plan for here’s how we are going to execute and do this thing. D, you have got to get out of the way so that your hoopers can ball. That seems like a very oversimplified sports metaphor, and I can be accused of that sometimes. Brett: Simple can be really powerful, and I really like that. Sasha: It is a powerful lesson, and I am thankful that I had the chance to watch elite coaches at North Carolina. I was on the team for a season, and I didn’t really play that much. I just got the chance to watch them work. I got the chance to see how they operate. I got to see how they motivated people. I got to see how they tinkered and put this person over here and that person over there. I think more than anything else I think I just saw how authentically they cared for the people that were on their team. When I was at North Carolina, I knew my coaches cared about me more as a human and as a person than they ever did as a basketball player. I think I have tried to take that as well as part of the lessons I learned from being involved with athletics. I think the second one that we talked about a little bit, which is what you highlighted of sports and confirmation and conflict transformation, bringing that over into the business setting and the business world and running a company. I think the lesson I would have taken from that first experience and taken it to running a company on a day-to-day basis is there are a lot of people coming from very, very different backgrounds and very, very different settings. You have to be cognizant of that as you are growing and scaling your organization. One person might have a very different view of a particular problem or a particular issue or a particular policy that we are enacting, or a particular strategy based on where they are from or their personal background or what culture they come from. Are they from the Silicon Valley Bay Area, from the Southeast? Did they grow up in India? Are they an engineer and this is what they see every day versus being a salesperson and this is what they see every day? You really have to take a lot of that into account as you are making decisions, as you are communicating your vision, as you are communicating policies, and just realize in a similar way from an athletics space, people may come from all of these different, disparate backgrounds but through the game of soccer, they can learn how to work together and become teammates and accomplish this great, amazing thing. In a similar way to business, we have got people from all these various, different backgrounds who are coming together, not necessarily through the game of soccer but through the business of Learn to Win and the vision of what we want to do in education, to go accomplish something incredible. It is I think very similar in those parallels, and a cool and fun journey to be on either way. Brett: I really appreciate that reflection and that’s something that’s very relevant for basically my entire journey and finding myself leading a company. Every single stage of growth has just been a new turn on the corkscrew of learning, exactly what you have been describing. I’ve really enjoyed this conversation. Thank you so much for joining us Sasha. Sasha: Thanks, Brett. This was a lot of fun. I appreciate you guys having me.