Somasegar – Part II

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Chris Williams: A 20-something Somasegar traveled alone halfway around the world to get advanced degrees in the field of his passion. But rather than a PhD in computer science, he got a nearly 27-year career on the bow wave of the personal computer era. He also got a lifetime of learning about what it takes to build great teams.

In the last episode, we explored his journey and his passion for leadership. This time, we learned about how he worked to establish global development centers at Microsoft. Turns out changing a headquarters-centric high-touch culture toward remote work is not easy. But the lessons he learned can teach us all a thing or two now that COVID-19 has forced virtually all knowledge work to retreat to home.

We also explore the decision he made to walk away after over a quarter of a century and toward a field he knew very little about. He tells us how it followed a personal theme of consistently looking ahead. Through this decision, he tells us about his move into the world of venture capitalism, and what his world looks like there. And that’s what this is all about.


This is Leading Smart, the show about managing in the brainpower age. It’s a field guide to the joys and challenges of leading and working in the modern workplace.

I’m Chris Williams, your guide to the stories and ideas that I hope will inspire you to be a better leader in the world of knowledge work.

This episode wraps up our conversation with a thoughtful and compelling leader. This is Episode 224. Part Two of my conversation with Somasegar.


In part, one of our conversation Soma reflected on his journey and how he learned to lead. In this episode, we begin with his passion for turning Microsoft into a distributed development company. To “build the muscle” of remote work. This was driven primarily because he knew intuitively that to hire the best people, you have to go where the talent is.

Somasegar: I can’t tell you, why kind of thing but I’ve always been passionate about and if you go back to the very early days of Microsoft, you would remember this, right? Microsoft had this philosophy of like, you know, hey, if I can see you, I trust you. If I can’t see you, I don’t care who you are, I don’t know who the hell you are. Forget it doesn’t matter, right? So we grew up in an environment where we felt like, you know, hey, we were such a special company, such a great company, that if you wanted to be a part of us, you would pack your bags, and no matter where you are, you will come to Redmond. That’s how we grew as a company, right?

And that worked really, really, really, really well, for the first 10 years for the first 15 or maybe even 20 years kind of thing. But even in the early 90s, I felt that like no, hey, that’s a that’s a faulted strategy. Okay, there is no way, you’re going to be able to get every bright and smart person who should be at Microsoft to come to Redmond, that’s just not going to work. Sooner or later, we are going to hit a brick wall, I don’t know when we’re going to hit the brick wall, maybe 1995, maybe 2005, maybe 2050. I have no idea when we hit the brick wall. But we are going to hit the brick wall.

So as much as we want a critical mass of people to come to Redmond, we have to go to different parts of the world. And I remember like starting in 94, I think I was like making you know a pitch to like, Hey, we should do something here. We should do something there. And like Now, obviously given I’m from India or sort of using India as a place to say like right, there’s a lot of English speaking people, educated people, computer science is on the rise here. You know, there is a cost advantage, at least in the short term, right? Why aren’t we taking advantage of that? Right? You’re sure we’ll continue to get people from India to be part of Microsoft. But we aren’t going to get a billion people from India to be Microsoft, right? Or even whatever the number of computer science, talented people are, right?

So but it took me like not three years. And for Bill to make his first trip to India and come back before we finally got Microsoft to say like, you know, hey, Go experiment. Okay, I still remember this very well, right? So Bill goes to India, I think it was in March of 97 kind of thing for a week or so. And he meets with customers with all the leaders, blah, blah, and he does his usual stuff. And he comes back. And I was talking to him at the time saying, you know, Bill, how’s your experience in those first time in India? What did you like? What do you not like anything? And he said, like, you know. I never realized there was so many talented people in India. And I said, I’m glad you said that. Okay, but he said, like, he always knew that the the people from India that we have in Microsoft are very sharp, very bright, doing very well. But I didn’t realize we had so many of those people in India. I said, yeah, India’s a large country and when a billion people can, I think, right, but that was definitely a huge factor in Bill because like, up until then he had only heard from me and others about like, you know, we should do something here. But just for him being an of feet on the ground, seeing firsthand the kinds of people and the kinds of like, you know, talent and what is possible there. I remember Bill then said like, No, okay, I’m going to give you 20 headcount. Okay. That’s so much, you know, you can go spend, I don’t know what you want to do, go figure out what we need to do. Okay.

That’s how we started, like, you know, hey, what became, in my mind, like, you know, a model for Microsoft, being a distributed development company, as opposed to everything is going to happen in Redmond, kind of thing.

CW: I remember distinctly when you got those 20 headcount. And you and I spent a lot of time trying to figure out how do we pay these people? How do we work this out? What is the you know, are there people from here that go back is that… Oh, boy, that was a complicated set of things to work on. It’s fascinating to know that there’s 8000 people in India now, which is twice as many people as there were when you started at Microsoft, whatever it was 30 years ago.

I will admit to being wrong. I always felt that your passion for doing that was as much to … I mean, yes, of course, it was to tap that, that talent pool there. But I also felt like in some ways, it was also for you to provide an opportunity for people who had come to Microsoft to go back and be with their families and many of those other things. I guess I never really thought about it as you thinking about Microsoft, being a distributed company that early and that was from your that was early in your thinking?

SS: Yeah. And then to be I’ve always told this to Microsoft, to Bill and to Microsoft kind of thing right now, hey, we will not be successful. If we continue believing that like not anybody and everybody will want to come to Redmond, there is going to be a limit to that. I don’t know when that’s going to be kind of thing, right? I also didn’t know whether like and I it wasn’t like an I knew that there was going to work very well. I said we have to experiment, we have to learn. Okay, a couple years prior to that, like, you know, we had set up a R&D Center in Israel. And you know how that happened? Yaron Shamir was at Microsoft here, he said, like, you know, hey, I’m gonna go to Israel, and two of my colleagues from Microsoft, we’re … three of us are going to Israel without or without Microsoft. Okay. I’m assuming that my there is no no interest in doing anything Israel. So we want to leave and we are going to go back. And then Paul Maritz, it’s like, oh, my God, like, no, hey, we don’t want to lose. These guys are great guys. Can they? Can we just set up shop there? Right.

So it was more accidental than what I called strategic. And India, I felt was the first time where we really thought about like, Hey, there is no real there isn’t like in my head, this individual wants to go there, or that group of people want to go there, or the following 10 people want to go back to India, kind of thing, it was more about like, you know, hey, how do we experiment with what distributed development could look like, so that we can learn and start building that muscle?

Once we decided that what I said was looking ahead to get the right level of cultural infusion, because you don’t want it to be completely Redmond centric. You don’t want to be completely a different culture kind of thing. Is there a way we could tap into a number of people who are here who are maybe interested in going back for a spell or for some time or just want to go back, kind of thing, can we use it as an opportunity to have the right level of cultural infusion as we build up an organization for scale for the long term that looks and feels like Microsoft as opposed to a completely different company? Because it’s somewhere else? Right? So it sounds to me like the notion of providing an opportunity for people to go back was sort of a means to an end.

CW: But so much of the culture of the company was built around being able to have a face to face conversation and so much of trust was around “I know you because I’ve you know, had a Starbucks with you.” Do you think the development in India helped the company realize this remote working is legal or works?

SS: It took us I’ll tell you it’s still, in my opinion, it’s still a work in progress. We’re still learning okay. Having said that, there were it wasn’t just India, we started in India, then we started in China, then we sort of had enough presence through acquisitions in the Bay Area. We started in Boston for a variety of reasons right. So, before you realize you started like not really seeing like not distributed things. India just happened to be like no the farthest in 12 hours or so time zones are like the craziest kind of thing and started earlier on, but it wasn’t like an Hey, just that one experiment, we said like in a hey, this is a muscle that we need an even we never thought that we are going to be in a completely remote work environment like what we are today because of the pandemic right.

But take India for example, you say that 8,000 people they are not all in the same city, there are not in the same location, we have one in Hyderabad, we have got one in Bangalore, we started one in the Delhi Noida region. And I’m sure we got other kinds of people all through the country kind of thing, right? So even within India, it’s reasonably distributed, is a distributed were like in a, hey, we don’t have a critical mass in any one location. Not, is it completely remote all the time? No, right? That’s all today’s environment.

But the notion of like, you know, hey, being able to take a bet, whether you are like, you know, 10 miles away, like in between like Kirkland and Seattle, or Bellevue, and Seattle, kind of thing, or whether you are thousand miles away, it’s, again, all the same thing. The time zones are different, but people are people and people have to figure out how to work together can I think. Thank God, like, you know, we got technology in our tools, like, you know, Teams and Zoom. And we got other kinds of, you know, interesting tools, multiplayer collaboration tools that are coming into play, that make it easier somewhat, but you need to have that culture that sort of says, like, you know, Hey, no matter where people are, we are going to be on the same team, we are going to work on the same set of things, we have an aligned set of goals, and together, we are going to make it happen, kind of thing, I think the work that we started in India, the work that we started in Israel, the work that was happening in China, that was what was happening in different parts of the world, gave Microsoft the confidence and the ability to say, like, Hey, I don’t need everybody here in the same.

And even then, like, you know, it’s sort of a evolving thing. Some of the old timers of Microsoft probably never got there. Some of them got there. But today, as a company, we are more open to a distributed development than ever before. And I think the work that we laid the foundation for back in the early 90s, or mid 90s, definitely played a big role in that in the company.

CW: You are a very personal leader, your leadership style is very much built around knowing and being in contact with people. Does this remote thing … was the remote thing hard for you to figure out? do you do? Do you think you’re good at it? Do you understand how to do it well, to lead people who aren’t sitting across the table from you?

SS: Again, like everything else, I’m thinking, I’m sure I made mistakes along the way kind of thing. But I think with over time, I’ve gotten reasonably good at that. Okay, because at the end of the day, like the principles are the same if you treat people the right way. Give them the right responsibilities, empower them in the right way, hold them accountable the right way. And sort of know that it is a two way street.

For example, give an example right, you know, India is 12 hours away. Okay, well, twelve hour timezone difference right. Now, like in our daytime, here is nighttime there. If I expect the the person that I’m working in India to always work through the night, I’m saying, hey, my hours are nine to six here us I don’t care whether it is night, nine to morning six for you, right? may not work, okay? But if I take a little bit of pain, if I share the pain, like no, hey, some days, I have to sort of stay up late at night. Some days, you may have to get up early in the morning, right? But we’re going to have to figure out together how to make this work.

And and I’m going to trust you the same way I will trust, whether you sit whether and whether you’re sitting in Redmond or sitting in India, but know that because you’re 10,000 miles away, I need to have different set of tools or different set of processes to be able to manage through this. I think we can make great things happen.


CW: When I was in human resources for Microsoft, Bill Gates and I had more than a couple of conversations where he extolled the virtues of “hallway conversations”. He firmly believed that these accidental interactions were essential to creativity. And to that end, we continuously relocated teams between and amongst the various buildings of the campus to facilitate this. I worked closely with the facilities people to arrange these moves, and they in turn constructed buildings specifically designed to make these interactions as easy as possible.

In fact, Microsoft is in the middle of tearing down that in entire campus and constructing a massive multi-billion dollar replacement complex based in large part on the principle that proximity accelerates creativity. I asked Soma if he felt there was a cost, not just to Microsoft but to the world, as we move to remote work, and this level of hallway interaction is no longer possible.

SS: It’s one of these things where you gain some, you lose some. And you have to be thoughtful about that and be thoughtful about how to make it work. Okay? Today, there are no hallway conversation anywhere in the world period. No matter how much you can lament about it, or how much you feel bad about it, just not possible. companies aren’t coming to a standstill, companies are trying to figure out like, hey, how do I make this work? What do I need to do to compensate for the lack of Hallway Conversations? So it’s no different? Like Not today, we are forced to do it, back then we were pushing ourselves to, to get into the uncomfortable zone to have to figure out to do what?

So to me, like, yeah, you, you must have watercooler conversations. But there are other other digital tools or digital ways that you can sort of, you know, enable some level of interaction, like you known hey, one thing that the people in India always tell me is like, you know, God, I hate coming to Redmond. Why? You guys are in meeting all the time. When do you ever get work done? We don’t lament about that sitting in Redmond, right? But people know outside Redmond tell you Oh, my God, the meeting culture and Redmond is horrible. Okay, I wish I don’t have to come to Redmond as often I can come.

So you know hey, they’re more productive, because they don’t like spend a lot of their times in meetings, right. But they miss the hallway conversation and the and the spontaneity of that, right. So. So you could argue that there are pros and cons or sort of gives and gets, you just have to think about what they are. And think about what matters to you on how you want to work on that, given the environment that you have. And then I think it’ll be phenomenal.

CW: You know, there were companies that were trying to do it, prior to the pandemic, they were trying to figure it out and make it work. And of course, there were sticks in the mud, were saying I wasn’t going to move and you know, but then there were companies that were doing it and say… and then all of a sudden, the playing field is leveled by the pandemic. And everybody has to figure this out. And it’ll be very interesting to see if it does spring back.

SS: I don’t know if you know Stewart Butterfield, he’s the CEO of Slack. That guy in a couple of months ago, he made the statement, which I thought was a phenomenal statement. He said, You know, if you had gone to like, you know, the CEOs of any company that had over 100 employees and told them like, you know, you got a week’s time, and all of your employees are going to be remote. The world would have panic, the world would have rebelled against that. Except that’s exactly what happened.

So sometimes, like, you know, what we think of as like, you know, hey, true, right? tested practices, behaviors, we just don’t want to think outside the box, we are unable to think outside the box. And sometimes we don’t even need to think outside the box. Right? So, but when we have to think outside the box, we rise to the occasion, right? The same Microsoft, which in the early 90s was saying like, Hey, everybody is gonna come here is one of the first companies to say like, No, I’m gonna, like, enable, like, no remote working.

So to me, it’s all about like you know Hey, constantly saying like, you know, hey, what you have today may work very well. But that doesn’t mean you want to be close minded about new ideas about new ways of doing things. Right.

I’ll tell you last week, I was talking to somebody from Gitlab. Gitlab is this company that has been right from day one, all remote? Now granted, they are not there. No, Microsoft, they are no Amazon, they got only like, you know, a couple thousand employees taken I think, right from day one. They have tried building a culture where it’s okay for people to be wherever they are. They’re all part of the same company, but have the same set of products and services, serving the same set of customers, and they want to make it work. And so far, they are happy. And the pandemic environment has only enabled them to sort of not dig in deeper and say, Hey, we think our model is going to work, even as we scale.

We talk about it as like, you know, hey, what is the future of work going to look like? Okay, one way to think about it is we used to live in a world where we started thinking about physical first workflows, okay, hey, I want to see in the hallway, and that conversation is going to be helpful. We start with that work. And then occasionally we think like, I assure if you travel to like, you know, Eastern Europe, sure, I’ll still will be okay working with you kind of thing, right? We, and we know intuitively that over a period of time, we are likely to get to a world where it’s going to be a digital first workflow, but know that there’ll be some physical force workflows too. The pandemic has really thrown us to an extreme and said forget digital first physical first, you’re in a digital only workflow, figure out how to make it work. So whatever we thought we are going to get in terms of the future of work for the next 10 years, 20 years, 30 years. We are sort of on a fast track to figuring out today.

I do think we are going to snap some back to sort of a hybrid workflow. But I think the the level of progress that we made, is going to be incredibly hard to unwind completely, we know will be taken a step back, maybe we’ll take a step back because kinda hey we can afford to, because we see like, you know, hey, some of the gives and gets that we have with not having any physical interaction is probably not the right thing. So we’ll find a balance. But will we go back to like you know, hey, we are going to build a $6 billion campus for like, you know, a 110,000 people, I doubt that that day is going to come anytime soon, may never come.

CW: One of the trickiest parts about remote operations in an organization is cultural. It can be hard to strike a balance between having a uniform culture worldwide, yet still reflecting and respecting the local environment. This can be a complex and delicate dance. I asked Soma if he felt like it should be 50-50 headquarters versus remote or some other balance.

SS: Yeah, I don’t know that I have a number for you in terms of should it be 50-50 or 60-40, or 40-60, kind of thing, but I think a fusion of both is absolutely required. As I mentioned before, it can’t be like, you know, hey, you decide that Microsoft’s culture, culture is the best culture, whatever is working in Redmond. And I’m going to transition that to like, you know, India and China and other parts of the world can I think you also can’t completely say like, hey, Microsoft’s culture is Microsoft’s culture and Redmond, I’m going to do something in India or China or some other place. And that’s going to be completely different than it won’t work as well. Right? So you have to think about like, you know, hey, what is the what do people think locally? How do people behave locally? How do people operate locally? What works? What doesn’t work? How do you marry that with like, you know, Redmond culture, Microsoft culture kind of thing. So that there is some level of conformity and sort of being able to work to it.

Let me give you one example, right. For a long time, after we started the R&D Center in India, we we had this problem where like, no people would just not talk. That you asked me like, why am I quiet? I don’t talk much in meetings today. Why not? That’s all I am. Right? That’s a lot of Indians are right. Not every Indian but a lot of them. And and so we will do a meeting and you know, you’ll have like a Redmond team on the India team. We’re now working together on something. The Redmond folks will be talking, talking, talking, and be quiet, quiet, quiet, quiet on the India side and feels like a hey, do you get what we are saying? Why are you not participating? Does it mean you have no idea what we are talking about? Or do you not have any point of view? Right? It was a cultural issue, right? It took time for Redmond managers to understand the kinda Hey, we know there may be other people that may not necessarily be comfortable talking in a group environment, how maybe like me should say like, Hey, Chris, do you have a point of view? And then sure, you start saying something, and once you start, hopefully, you’ll get the right point. And if I do that six times, maybe the seventh time, you will automatically do it yourself. Right?

So so you’ll have to sort of get people on the site to understand that, and people on that site to understand like, you know, what is the value of speaking it is not like no by you, voicing your opinion. And people are, are scared when it is the opinion that disagrees with what somebody else is saying? Because they’re their first thing is like, no, how are you going to think that I’m insulting you? Or I’m not respecting you? How do I say it in a way that you sort of view it in the most constructive way? Right. So there are a lot of nuances that people think through. And you have to keep that in mind. And at the same time, the person that needs to understand that, again, it’s not about disrespect, it’s not about this, it’s about adding value. And it’s about making sure that we are doing the right thing. And people take it in that respect. Right.

And and so you like to work through these sort of cultural nuances, cultural issues. You know, the reason why I was excited initially about taking a number of people from here and sending them back is, hey, these people both understand the local customs, because they came from that part of the world. And they’ve been at Microsoft long enough that they know the Microsoft culture, can they be sort of, you know, helping us create, like, you know, what I call the fusion environment that’s likely to be the best, both in the context of Microsoft and what might work in one geography was the other geography.

I’ll tell you, the other problem is like no one. And I can tell this No, because I have sort of been with all the geographies, right? You look at Israel, you got the other problem, right? The person is, like, passionate, and they’re arguing all the time, not because they want to fight with you, or because they sort of think badly of you. They really are passionate about what they’re saying. And they want to make sure that they convey that passion, right. But for a lot of people who are not used to that, it’s like, you know, why are these guys antagonistic all the time? Why are the yelling all the time? Why are they shouting other Oh my god, it’s frustrating. No, no, like, Look, get past that emotion. And think about what they are saying. And maybe you understand why we are saying that. And it is not like, you know, they’re saying they’re right or they’re wrong. They’re just saying like, you know, this is how I am, right? Because it’s a cultural thing. And the more we can understand like and we talked about Diversity and Inclusion kind of thing. I think the more we understand this, the more we figured out how to work with these people, whether they are here or whether they are in some other part of the world. It just like you know, absolutely required for every company today.


CW: After almost 27 years at Microsoft, Soma decided to leave and join Madrona, one of Seattle’s premier venture capital firms. I asked him if he left Microsoft, or did he go to Madrona?

SS: Great question. So let me tell you the story again. Okay. And before that, I actually want to share one one other thought, which I think largely is like, I felt it was a lesson for me.

I had sort of joined Microsoft, and I really loved the company, I loved what I was doing kind of thing. And I’d always thought that like, you know, hey, I’m going to retire from Microsoft and be done. And that maybe 50 years from now 100 years from 100 knows how long, but I’m excited about it, right. And I found that there are three things that were important to me. Okay,

I want to be in an environment where I feel like I’m learning every day, which means the people around me I feel are at least as smart and hopefully smarter than I am. So I can learn learn learn. That was really important to me.

The second thing is, I wanted to have what I feel is an impactful job or role can have a meaning whatever I was doing, I wanted to make sure that like not the output of what I was doing, and by extension my team was doing was going to have a positive impact on this world, in some way, shape, or form.

And the third thing is, I want to know that I’m having fun at what I’m doing. And for the 27 years or more, at least 26 years, I should say at Microsoft, that I felt that it these three things were there, I’m going to give it another year, I’m going to give it another year, I’m going to give it another… I’ll give it forever kind of thing, okay. And I still believe those three things are super valuable.

What I now realizes there is a fourth thing that I should have added, which is, Hey, I, I want to learn, I want to be in an environment where I’m learning. I want to have impact. I want to have fun. But I also should be thinking about what else? In other words, okay, hey, I may be doing well on those three dimensions. But if there is something else where I have a an opportunity to have more of a learning opportunity, more of an impact, more fun, I should at least consider that. I think for 26 years, I did not consider that. Okay, I never even thought about it to me, like, Hey, I checked mark, the first three things great, I’m done. I didn’t think about like, Hey, is there something else I could do in this world, that would give me those three things and give them in spades or more a lot more than what I’m doing right. And I saw my mind sort of encouragement to everybody, everybody in this world is, please think about the fourth thing as well.

In other words, we all have a finite amount of time I ahead of us, no matter whether I’m one day old, or whether I’m hundred years old, page finite, the best thing that we can do is be thoughtful about how best we want to use our time. It can’t be like you know hey, I am happy doing what I’m doing. So I’m not going to think about anything else. If there is something else that is going to be even bigger, even better. Even more impactful, even more learning, even more fun, you should at least consider that. For a variety of reasons. You may say that is not the right thing for me now. But don’t not consider things. Okay? Because you really want to optimize and maximize how you use your time. And you want to be very, very, very happy with how your choices and how you’re using your time.

So coming back to my Microsoft story now, right? So 26 years. And when I finished my 26th year, if you had told me like, Hey, I won’t be working at Microsoft someday, I would have laughed at you. I said, What the hell are you talking about? I’m going to be another 25 years kind of thing, okay. Couple things happen. One is like no, like, like all people like now our two second daughter left home. So my wife and I started thinking about like, hey, we’ve been doing this for 25, 26 years now. Are we ready to sign up for the next 25 years? Okay. And then I started thinking about it and they start thinking about like, in my head, what am I doing? What am I learning? What do I see, you know, the company doing what do I see me doing, you know, over time kind of thing. And I started coming to a realization that like, you know, hey, I think I’m going to be excited about Microsoft for maybe another 10 years, maybe another 12 years. Okay? But there is going to be a time horizon in the future, when I feel like I may be done with doing the kinds of things that I’m doing at Microsoft, okay.

And when I started thinking that way, I really panicked, okay? Because to be like, hey, if I’m not going to be in an environment for the time or reason that I’m thinking about, why am I wasting my time there? I should have left the place yesterday, not tomorrow. And remember, 10, 12 years from now my ability to learn something new is only going to be little lesser, not gonna be bigger. Okay, just the law of no natural things. Okay? I said like, no, hey, I really think no health permitting and everything else being normal kind of thing, I want to be productive for at least 25 more years, I actually thought like, 27 years at Microsoft 27 more years, right. And if I don’t see my next 27 years at Microsoft, and I also don’t want to work for another company, then I was always clear like, hey, Microsoft is a great company. If I if my goal is to work for a company and want to work at Microsoft, okay, then I have to figure out what the hell am I going to learn, be something different completely. And no way that I’m going to be having fun, where I will learn when I want to be good at that. And then build a runway for 27 years.

So I started getting into panic, right? And then they you know, Satya and I had a conversation, Satya had a simple ask. He said, like, you know, I’m not asking you for too much. Just stay in the company for as long as I stay. And the day I leave, both of us can leave together. Thank you, I really appreciate that. That was awesome kind of thing. But But hey, I don’t want to stop working 10 years from now. Okay, or 12 years from now, 15 years from now. And I knew that like someday, I was going to get up and say like now Oh my god, do I really want to go into work today. And I don’t want to face that day. So I said like, hey, I would rather you know decide to do something different now.

I’ll tell you another thing, if six months before I left Microsoft, if you told me that I’m going to be a venture capitalist U would have laughed at you. Mainly because I didn’t know what venture capitalism meant by then. Okay. So it wasn’t like, you know, I had this dream, I had this passion, I want to be a venture capitalist. I knew that let you know, hey, I need to find something else if I want to really figure out what I’m going to for the next 27 years. I knew it was it might not be Microsoft. And definitely if it’s not Microsoft it’s not working for another company. I better go figure it out. Better go figure it out. Right.

So that was the push and try finally for me to say I need to leave. And it took me and Microsoft was very gracious. They said like, hey, continue here or go talk to this person or go talk here. What about this? What about that kind of thing. And it took me… it was a it was a long process was really a nine to ten month process in my mind. Before I finally not only I had to make the decision, but I had to talk to people around me to make sure that like hey everybody felt comfortable that this was the right decision at that point in time for me and for the company to say like, hey, let’s let this guy go and do something else.

CW: But But and you just said it though. Venture capitalism… I mean … you had never even seen a startup, right? I mean, I that’s an exaggeration for effect. But I mean, Microsoft was not a startup when you joined. So … aside from learning a heck of a lot, how do you feel like you can add value to a startup?

SS: So a couple things. One, is they going up with by chance are like no by choice, I don’t know what it is kind of thing, my only interaction other than like an Of course, they’re going to have understanding what the developer world look like from a startup perspective and engaging with startups to make sure that we are aware of the trends kind of thing. I had started writing checks as angel investors in companies it was mainly because like, you know, hey, my friend wrote like now left Microsoft say like, can I have more to start a company? Can you invest it? Sure. And and my involvement was, like, you know, maybe spending an hour with the entrepreneur and writing a check and then forgetting about it.

So I can’t tell you that I knew a lot of what startups were other than I have written checks to startup. But But what I one of the things that I realized, like in talking to all these entrepreneurs over the years in a variety of context is the one thing that is common among all entrepreneurs is their passion and energy to want to change the world. Right, everybody dreams about changing the world. Now, some of them obviously go do it and saw them like, you know, get a little way into there and saw them fail miserably, but doesn’t matter. Everybody has the passion kind of thing, okay.

So, as I was thinking about leaving Microsoft, one of the things I started thinking about what should I do next, right, I don’t know right. There, it quickly came to my mind, there are only two things that I could realistically do based on whatever knowledge and experience I have.

One is I have this brilliant idea that I’m willing to dedicate the next 15 years of my life to go from my own company. Okay. But and the reason I said 15 years is because it takes that amount of time for everybody thinking that like companies become overnight success. It takes at least fifteen years for you to create some enterprise value of some consequence. So I need to be ready for that. And I need to be passionate about the problem passionate about the problem space kind of thing. And I quickly realized that like, Hey, I don’t have the brilliant idea that I make desirable for the next 15 years, right?

The only other thing that I could think of was like, No, Hey, can I work with entrepreneurs, and help them? Like, I have a little bit of experience in building products, you know, running teams, you know, building teams, scaling up teams, you know, selling to customers, and building businesses kind of thing. So if I can take all of that, and if I can sort of somehow work with one or more entrepreneurs to help them? Is that gonna keep me busy? Is that gonna keep me you know, excited, is that a learning experience for me? Am I going to be valuable, I’m going to be good at that. I didn’t know any of those things.

But I felt like hey, I could see myself not trying at least my hand at that. So when I went into Madrona, my sort of deal with Madrona, had been with me was like, Hey, we are going to give this a shot. Because remember, I am this guy who’s sort of, you know, not written code in a long time, has managed thousands and thousands of people in large company environment, nothing to do with like no startups kind of thing. And I’ve always had, like an army of people with me to do lots of things, that I wasn’t an individual contributor in any way, shape, or form for a long time, I want to give all that up and say, like, Hey, I’m going to be great at being an individual contributor, not only that I’m going to enjoy, like being an investor and sort of, you know, working with entrepreneurs, and really adding value and making the right investment choices, so that we can sort of be a successful venture can form a lot of unknowns.

But thankfully, Madrona guys said like, no, yeah, we know, we know a little bit about you, have you heard of you, like, come on over? Let’s try it out. And I said, Sure, we’ll try it out kind of thing. So I went in thinking that like, I am going to learn for a year or two, and I’m not a that decide that this is amazing. And I’m gonna do this, or no, oh, my God, this sucks, or who knows what will happen, right? But I would say in about like, three to six months for me, it is for me, because obviously like, you know, hey, I think I can do okay, at this, I think I can add a lot of value, I think I’m going to enjoy this.

So within a year, we sort of formalized like not the, you know, that I’m going to be a managing director at Madrona kind of thing. And now it’s five years kind of thing. I can still tell you whether I’m a great venture capitalist or not, but I’m I know that I’m learning every day. And I’m wanting to do my best kind of thing, ever. But it’s one of those things that like no, I so I would say I’m an accidental venture capitalist, because I had a set of parameters and thoughts about like, you know, how I want to spend my time. And I’m so glad I’m doing what I’m doing now.

CW: Are you helping to advise these companies? Are you making decisions about investments that should be made? Are you … what is your role? What are you trying to, you know, you said, you want to wake up every day and feel like you’re being productive? How are you doing that?

SS: I would say it’s all of the above. As a managing directory, what do you do is you do all of the above, right? It starts with like, you know, hey, fundraising, to get funds from our LPs, right? And then it’s all about looking ahead, looking at new entrepreneurs or new companies and deciding where you make investment decisions. And once you make an investment decision, you get on the board of a company, and then you work with that company, for the next 10 years, 15 years through their journey kind of thing. So I like to do all of those things, right?

So I enjoy, like, you know, all aspects of what I’m doing today, right? Because to me, like, I have never fundraised in my life. That’s a fantastic experience, you learn a different skill set, you build a different set of muscles, you build a different set of capabilities in the process, right? I love managing and being a part of a management team for a firm, where like, you know, as I mentioned before, there is no, it’s not like anybody works for me, I work for somebody kind of thing, but we are a team that has got a loosely governed our set of governance and policies and rules for how the team works together. And being at the top of the firm gives me an opportunity to sort of help shape the strategy and the direction and the culture along with my sort of co-managing directors, kind of thing I enjoy that a lot, right?

Being able to sort of, you know, talk to entrepreneurs and sort of look around the corner and think about like, hey, what is going to be the next big thing, and which is the team, you want to take a bet on the next big thing. And and knowing that, hey, there is a roll of the dice here. Hopefully over time, you’ll sort of build better intuition and better capability to do that. But that investment decision.

And the one thing I learned like which which I did not appreciate at all before I sort of ended venture capitalists, particularly my bad habit as an angel investor, where I would write a check and forget about it. I didn’t I didn’t really appreciate the, hey, once I write a check as a venture capitalist, I’m really getting into a marriage with the entrepreneur for the next 15 years. Okay, it’s a long term relationship on long term organization, about like my, I come in, I write a check and then occasionally I’ll show for a board meeting, kind of thing, you roll up your sleeves and you work hand in hand with the entrepreneur you work with the management team, you do your part to be helpful to the team, whether it is hiring. recruiting, whether it is like, you know, thinking about product strategy, whether it’s think about go to market strategy, whether it’s thinking about pricing and packaging, right? Whether it’s about who to fire and because they’re not doing well, it’s a lot of things. But but it’s the thing is, you are one step removed from sort of the person who’s, who’s likely running the show, right. So I have to be a both understanding and aware. And think about, like, you know, how I can be influential in the most effective and constructive way in the process.

CW: The other thing that it strikes me that that you get today that you didn’t get before, is phenomenal variety. At Microsoft, for me, one of the things I remember when I first got there, I felt like a kid in a candy store, because there were so many different things to do, and so many different ways to do something, but you ended up having to do one of them for three or four years at a time. And you have the situation now where you can do something for three or four hours at a time.

SS: Completely agree with that. Okay. So if you ask me, like, in my head, why am I glad to being a venture capitalist kind of thing? I would say there are two reasons. One is the depth and breadth of technology that I get to be a part of, that’s, like, completely new, it’s like a kid in a candy store, like you said kind of thing, right? Because like, you know, hey, I get to work with autonomous vehicles, you know, when one company I get to work on, like, you know, hey, how can I detect, you know, early cat cancer in early stage, so that I can, you know, help the world at large. Third is like, you know, hey, how do I with this COVID-19 thing? Is there a way to sort of know, increase the capability for how we can test and detect faster? Okay, the fourth thing I’m thinking about like hey? How do I sort of, you know, reimagine what productivity tools could look like, okay, or the fifth company is like, you know, hey, with all this, like, no sort of remote work online kind of thing, is there a way to reimagine how corporate learning and training should happen in online work, right?

So the, the range of the problem spaces, the breadth and depth of the technologies is phenomenal. So that’s one reason. And the second reason is, as I mentioned earlier, the notion that I get to work with people who have the passion and energy to want to change the world. And do that every day, every hour of the day, kind of thing, that’s like, you know, highly infectious and I love that. Those are the two reasons. So you’re right, in that like, you know, hey, the breadth and depth of technologies is amazing. And I love that, right?

And, and I feel like, you know, hey, even if I were running a company like Microsoft, there is a finite amount of things that I’m going to be doing. Whereas here, as a venture capitalist, we really have the opportunity to, to dream as big to think as wide right, to go as deep on a variety of things that are sort of real problems to be solving, hopefully, things that are going to move the dial in some meaningful ways in the world. Over time, kind of thing, that’s a very fulfilling part of being a venture capitalist. Yeah,

CW: it’s just, it’s making me smile, just thinking about it. It’s just absolutely fascinating. Um, you went off and ran the developer division, or whatever it was for four years at a time, and you woke up every day thinking, you know, having to think about about a given problem? Do you worry that you don’t get an opportunity to deep dive into any of these problems?

SS: Absolutely, it’s one of those gives and gets, I don’t get to deep dive into any one thing, you know, to the extent that I was able to do when I was at Microsoft, but you have to decide like, hey, do you want to go deep in one thing? Or do you want to sort of, you know, go a little, little less deeper or a little more shallower, but across a wide variety of things, right? I feel like my, hey, I spent a considerable amount of time working on like, you know, something that is deeper, or, you know, something that is a little more constrained in terms of the focus kind of thing. And now I’m really enjoying the breadth of technologies that I get a chance to look at. And I feel like all the foundational work that I did, or at that I learned, or the experience while at Microsoft, you know, working on platforms, working on developer related technologies, right? Thinking about the world of computing, I think I can take all of those things and apply it to a broader technology base today than ever before that.

Like you know, again, three years ago, if you had told me like, I would be working with a company on like, you know, hey, how do I detect cancer earlier, I said, Well, I don’t know anything about cancer kind of thing. But in today’s day and age, you know, where Life Sciences is coming together with data science and computer science. And that intersection of innovation is sort of, you know, something where we think there is a huge opportunity for innovation and breakthrough. We have an opportunity to go play in that. And that’s Oh my God, that’s like no new muscle for me. And I’m never going to be a life sciences guy. Let’s be clear, but I can be learning enough to be dangerous.

CW: Yeah. Yeah. I’ve taken way too much of your time. This has been absolutely a blast. I really enjoyed this. This is fun.

SS: Absolutely. And I should tell you two things here. One is I’m really glad you’re doing this. Because Because I think this notion of sort of letting people sort of know, voice their opinion. And being able to sort of, you know, think about how you can sort of channelize that into something that like, you know, maybe others would love to hear kind of thing, I think that’s a fantastic and today’s day and age like, no, the, the podcast is probably like not as effective as a medium as anything else for us to be able to sort of, you know, hear each other’s perspectives and each other’s views kind of thing. So thank you for doing that.

And right from the Microsoft days, it’s always been a pleasure chatting with you. So I really enjoyed the last two hours. So thank you.

CW: I’ve just I this has been as much fun as I could have hoped for. So you’re, you’re a really good guy. Thank you very much.

SS: Thank you.


CW: I want to thank Soma again for spending the time with us. He’s right. The chance to hear other smart and thoughtful leaders is always time well spent.


Leading Smart is from me, Chris Williams. You can find out more about the show and discover other resources for leaders at my website, CLWill.com.

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That’s it for this episode. The next episode, we’ll continue this series on communication. It’s called “Feedback Loop”. I hope you’ll listen. Until then please remember that each of the several dozen decisions you make today are part of Leading Smart.