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Navigate Career Pivots

with John Kim

April 20, 2021
Navigate Career Pivots
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John Kim - Co-founder & CEO @ Sendbird

John S. Kim is the Co-founder and CEO of SendBird, the world's no.1 chat API. The platform currently serves over 100M monthly chat users across the world's leading companies such as Reddit, Delivery Hero, Yahoo!, Rakuten, Paytm, Accolade, Livongo, and DHL. John is a serial entrepreneur, engineer at heart, and an expert in the API economy and communications tech space. Little known fact about John is that he was Korea's no.1 pro-gamer for Unreal Tournament.

"So if you're working at a bigger company, what you're really trying to optimize for is how quickly can you move up in turn terms of 'Abstraction Layer.' It's not about titles. It's about, can you actually understand the next layer of abstraction within the business.

So if you're like an IC, what is the engineering manager's priority right now for your team? What is the, let's say a director of engineering's priority right now for the team?

And if you actually start caring about those things, you'll be able to make a lot more faster progress."

- John Kim

Show Notes

  • How John went from professional gamer to #1 chat API company @ Sendbird (2:47)
  • Creating vs. consuming & why John walked away from professional gaming (6:58)
  • John’s early career pivots: from software engineer to social gaming & Y Combinator (9:08)
  • How to apply the complexity science principles of “Convergence” & “Divergence” to your career decisions (11:17)
  • Navigating “Abstraction Layers” & why you need to invest time to build “social capital” in your career (15:31)
  • The “Human Capital” Framework & balancing the skills you accumulate throughout your career (19:04)
  • Building emotional capital, training for cognitive empathy, & the tradeoffs of agreeableness (20:41)
  • How to manage expectations & communicate with stakeholders when you need to pivot (27:34)
  • How John applied these principles to make career decisions and pivot his company (30:23)
  • How to pick careers aligned with your happiness and motivation (37:10)
  • How to pivot your career using the “2PM” framework (people, product, market, money) (39:59)
  • Future founders: Why you’ll be happier making 10 year career decisions & quick pivots (44:04)
  • Takeaways (46:23)


How John went from professional gamer to #1 chat API company @ Sendbird

Welcome, John! It's great to have you here on the show. Jerry and I have been really looking forward to this conversation for a number of reasons, but I think first off, we just wanted to say, thanks for joining us here on the podcast.

John Kim: Yeah really excited to be here. Looking forward to our conversation today.

Patrick Gallagher: Before we get into the conversation, I wanted to start by, I think, noting why we're having this conversation in the first place. Because your background is really unique and distinct from many of the guests that we typically have on the show.

Just to make a couple of quick notes, the world of technology obviously moves fast and is accelerating. And this is something that many people in our community and our listeners know firsthand. There's also common career advice out there that you can expect to have multiple careers throughout your lifetime. And from some of our experiences... career development we found, is often non-linear and when it changes, it usually changes in a dramatic fashion.

I think the last note is that in my personal experience, I find the most interesting lessons and insights often happen at the extremes.

All of that to say, to match the changing pace of the tech industry and to be appropriately prepared for the inevitable "dramatic career change..." we probably need to look at an extreme example of someone who's had success in really different careers.

Which brings us to our conversation with you, John! And so we're here today because your story really provides an incredible example of what success looks like in really a few completely different careers. And so we're here to really deconstruct your thought process through that whole story and understand how and why you made those choices.

With that said, how the heck does someone go from being a professional gamer and the number one Unreal Tournament player in South Korea, to the founder of the world's number one chat API company?!

Can you give us the quick overview of the story arc for everything going on there?

John Kim: Yeah! I wish that life was as simple and beautiful as that, but obviously there's a lot of ups and downs in the middle. So, you know, when I was a kid, probably a lot of engineers would resonate is, you know, I was an avid gamer. I literally had no social life. All I did was play games all day long and to tried hack games, create community around games and stuff like that.

I learned how to program. because I want to create community for games and also hack into games and create games. But still I was, I wanted to become like a scientist when I become serious adult. But as a child, I will always want to like play games and create games.

So I ended up doing a little bit of software engineering or learning how to code pretty much by myself. I mean back in days we didn't have online classes or whatnot. We didn't even actually have a decent internet. So played a lot of games and start playing little bit, bit dial modem. And then learn how to connect the internet and they start playing on networks like Kalia and stuff like that.

And then start playing a little bit more competitively. But this is the early era of professional gaming. So, the gaming leagues were just about to, you know, getting set up out of, some of the audience might recall. There was like players, like Thresh and Fatality played a lot of like Quake, Doom era. I was like in the early, early days of gaming.

Patrick Gallagher: I saw all those players on Tech TV and G4 TV back in the day. I totally know what you're talking about.

John Kim: Yeah. And Thresh, actually it turns out to be a fantastic entrepreneur too! Create multiple companies that have done phenomenally well. But, But back then, I didn't really care about the business side of things.

So I played a lot of games. And I got recruited into Samsung Con, which is the first gen of professional gaming team. And then probably again, the prize money back then was like a couple of thousand bucks. and they give you all the free swag, the highest quality headphones, the fastest graphic cards If you win. But for a kid who is in their like late teens... It was like, living a dream basically.

And then, you know, once you kind of get to their level of what people sometimes call it, peak performance. You look around yourself and everything is pretty much downhill from there. If you, win you're at the same place. But if you lose, you just get embarrassed.

And you start to realize a lot of kids in their mid teens start to catch up with you. You recall, your hand-eye coordination and start to get a little bit slower. You become a little wiser with strategy, but just a foundational level of skills start to degrade a little bit.

So you're like, "Okay do I want to stay here as long as possible and, you know, really get embarrassed and stuff like that? Or just leave when I'm at my peak?"

So I kind of decided to do that because I could be spending time more on creating things. So I actually quit the game entirely that day. When I won a one of those tournaments and then just completely switched over to creating programs and, basically learning how to code more deeper.

Creating vs. consuming & why John walked away from professional gaming

Jerry Li: I'm curious to ask about how did that happen? You have been intention focusing on that for, fora very long time. That's your passion? How you, were able to walk away from that so quickly?

John Kim: Well, two things... I kind of look at the world as the world of creators and world of consumers, right? You either are creating something or you're consuming something. All the time, of course, on one person, who's not a hundred percent creator all the time. Right. You create on a day-to-day basis, you create something, you consume some. and then I look at where I spend my time.

What I realized was I enjoyed creating game communities. I enjoy creating programs. And that passion grew over time, whereas enjoying playing games decreased over time. And then I looked at a couple of other professional gamers out there who were massively successful back then. And I met them in like tournaments and they fly with their coaches or dad as their managers. And they are literally professional players.

I was, dubbed "professional", but I simply enjoy playing games. I kind of good at it, but the other people were like really, really serious. They got sponsorship, they had all this stuff that they had to, like rules that they have to follow. I didn't want any of that.

So I kind of look at them as like, I didn't want to spend the rest of my life doing that. And also found myself getting more passionate about creating stuff rather than consuming stuff. So I'm like, "Okay, I'm going to be a creator from this moment on." And then, because I couldn't really find a model, then I went to a benchmark from the professional gaming side.

Jerry Li: So the clarity about what you're interested, how you envision how your career is going to look like years after and that helps you to make that transition really quickly.

John Kim: Yeah, I guess in general, just to add to that is... a general rule I try to follow, at least myself is I want to get to a peak level of something and I'm probably not going to give up ever until I reached that point. But once I reached that I'm relatively quicker to make big jumps, like kind of letting go of everything I had and figure out what's next in my life.

So even if you look at our company's history too, which we can go in deeper later on but.. I pivoted my first company too. Which the pivot actually worked out, so we were able to get acquired. Second company, also, we did a pivot. So it was kind of, I ended up pivoting all of my career and all of these sort of items throughout my entire journey.

So I think there's hopefully some method to this madness. But that's been kind of my journey so far.

John's early career pivots: from software engineering, to social gaming & Y Combinator

Patrick Gallagher: So what happened next? What happened after you left professional gaming?

John Kim: Well, even before going to career, I started my school as a double E electrical engineering. I'm a Korean citizen, so in Korea you actually have to go through like mandatory military program. But instead if you're like engineer, if you've got some special government license, instead of going to the actual military, you can choose to work at a tech company as long as you get accepted by the tech company.

So I ended up working for a tech company as a software engineer. And then kind of worked at two different companies throughout that mandatory period. One of these company was company called NC Soft, one of the largest gaming company. So really a learned a ton there.

And after finishing the program, I returned to school, I pivoted to computer science and then finished my studies there. And then, as soon as I graduated... and I was doing professional gaming on the side while I was going through that journey.

And then as soon as I finished my studies, I started my first company. So it was a web 2.0 company back then. I don't know what version we're on these days. That was like late 2007. And immediately when 2008, hit with the financial crisis obviously no investor wants to invest in web 2.0 companies anymore. But because I had this background in gaming, worked for a gaming company before, I was a software engineer. Investors were like, " You know what? You should be making games! If you make games, we'll invest."

Cause we've been like courting each other for roughly a long time.

So again, I pivoted to social gaming company. That's where we received our initial seed financing, and then grew the company for about four and a half years. And then we got acquired. And then after that, I stayed there briefly.

And then started this company with the buddies from my first startup. So we've been working together for a good 13 years now. Then we started yet another social network this time. Kind of like a web 2.0 company, but for mobile.

We built that company for about two and a half years and we're trying to add a chat feature for our own application. then we went on to buyer's journey. And we couldn't really find a solution that we wanted to use. So we ended up building that ourselves. And then we started selling that on the sideline. And that starts to really take off.

So we applied to Y Combinator with that idea and got in and fast forward a couple of years now we are serving 130 million users and we had to shut down the initial application in the local community after we built. So we went from B2C to B2B in our current company.

So there was a lot of pivots and junctures throughout the journey.

How to apply the complexity science principles of "Convergence" & "Divergence" to your career decisions

Patrick Gallagher: So many different transition points in your career, but you know, as you share it, there are some things that seem like they make a lot of sense in terms of the things that you value and the things that you're interested in.

Throughout this whole process, how do you evaluate your career throughout all of this and these different choices? Are there core principles or frameworks that you've relied on to help guide you through these decisions where you feel like you have more reliability or confidence that you're making the right choice your next move?

John Kim: Yeah. usually I look through the lens of people call complexity science. In that field or kind of any field, whether it be industrial engineering, mechanical engineering, even like biology and whatnot there's a concept called problem landscape, right?

The entire life or entire business, you can, you can imagine it in terms of a, like a landscape, like you were looking at hills and valleys. They're big mountains. There are short and small hills. I kind of imagined myself blindfolded, just land in a random spot on that map. Almost like inside a game, trying to like figure out what's in front of you, but everything's black round you, only thing you can do is move horizontally.

And you can only assess yourself by how much higher you're going or how much lower you're falling. So you're trying to figure out, "okay, in which direction can I actually go up?" and your goal, your fitness function is trying to get to the highest point possible which should be the global optimum.

Now throughout your life you'll probably go through a lot of hills, you know, ups and downs. So you're always trying to figure out, " Am I going fast enough for the higher goal? Or am I getting stuck?"

Because you're blindfolded, you might go to a certain hill. Let's say some company or some career choice that you made you look everywhere and you try your hardest. But whichever direction you take, you feel like you're getting stuck for a relatively long period of time. That's when you know, you need to add divergence.

So convergence is that you're active trying to go up.

Divergence is being okay with going down, but trying to figure out and take a little bit of risk to figure out the next better higher hill.

And the balance here is that you don't want to add too much divergence, which means you're not going to climb any hill at all, you'll be jumping ship all the time. Or if you have too much convergence then you're going to get stuck on certain hill and you know, all of your peers are making so much more progress. You're not taking any risk. You're only trying to go up and you get stuck. So you're always trying to figure out what is the right balance.

If you look at evolution or biology, it's usually that, 80, 20, sometimes 70, 30 ratio, you always want a little bit more convergence because you want this structure, organization, you want the building of your career. But you sometimes want to add a little bit divergence so you're always being open to a new innovation and new opportunities. So I try to figure out, am I getting too stuck here or am I adding enough divergence throughout my career.

To give you the latest example when we were building this B2C mobile location based on social networking application. We got to this user growth where we feel like we were getting stuck at quarter million users. And feel like no matter what we tried, the needles were not moving. The amount of inputs, whether it be capital effort we were putting in our returns were getting almost like saturated. We feel like we are stuck at a certain point.

Now we can choose to double down and see if there's a bigger mountain right around us. But we knew within the given time, you won't be able to get to the next milestone that was needed to do our next fundraise cause we were running out of money at that time. So we had to figure out enough of a pivot where we knew with certainty that there's a bigger mountain out there.

That's why we experimented with a hackathon we did. Pull the chat into SDK, start selling the sideline to see if there's a better deal out there. And we realized our rate of climbing that hill was much faster. Which gave us the confidence. "Okay. Let's go down from this hill. Let's climb that hill because that hill we can gain the height a lot faster."

So it's kind of the mindset of divergence and convergence, and really balancing that out throughout your career.

I can go on forever, but just to add one more thing, if you think about search too, you learn about breadth first search. Breadth first is kind of like looking at what's out there. Depth, first search, You really go deep. Depth first is like convergence,, right? Breadth first is like divergence. And we already know like ACR algorithms, like it's the heuristics, it s the balancing between the depth and the breadth first that gives you the most efficient way to find the greatest outcome.

So throughout life, I tried to like have a mental mindset about business, to my career, to the life choices I make. I might, until I have the right balance between the convergence and the divergence.

Jerry Li: That's a really good mindset and mental model as well. The thing about career and also running businesses. Do you have examples that can help illustrate applications of the mental model?

Navigating "Abstraction Layers" & why you need to invest time to build "social capital" in your career

John Kim: Let me actually add one more model. So one is Convergence and Diverse model, which I explained.

The second framework I use is "Abstraction Layers." You move up or down between abstraction layers. The more you move up, consider a promotion or you're, have a bigger visibility into the business, or you're actually going deeper in the reduction where you're going to the IC mode. So I try to use those two kinds of frameworks to navigate.

So if you're working at a bigger company, what you're really trying to optimize for is how quickly can you move up in turn in terms of abstraction layer. It's not about titles. It's about, can you actually understand the next layer of abstraction within the business.

So if you're like IC, what is the engineering manager's priority right now for your team? What is the, let's say a director of engineering's priority right now for the team? And if you actually start caring about those things, you'll be able to make a lot more faster progress.

Now it's not for everyone because some people don't like this abstraction and vagueness. Some people do like concrete, actionable items and that's okay. Then you kind of choose on the specialist's path.

Now there are a lot of mistakes people make is that people think they would enjoy the people management side of things. So we're going up into abstraction layer. Surprisingly, that's not the case.

Now the problem with the current corporate systems today, a while just actually bifurcated, but some companies like Facebook and Dropbox does as well. But more traditional org, have this incentive that they will pay more for the people manager versus specialists track. So people are, are incentivized, because people are smart. So they'll think this is the only way for them to go up. So they'll choose the path that's not good for them. So it's ultimately discovering what you want to optimize for. Are you happy with moving up the abstractional layer? Or not?

Then you have to think about, "Okay, if I'm not happy, what do I do about it?" do I add enough of a divergence within the same org to ship to a different org? Or is this something that I actually have to create even greater divergence to jump to a new company or new industry? So it's a level of risk appetite that you have, which is actually a fundamental baked into your personality profile, but personally deeply rooted...

how much of a divergence are you willing to add to your career? That means a greater risk could be greater upside but could also mean that you're going to waste next three, four years, trying to get to where you are within the same company. So it's kind of thinking about that.

And now if you're at a startup, it's slightly easier. Cause I usually go by this model. And people probably think about the same way too is, you look at a company when you join a company try to look through the three, four years of timeline. Don't think about one to two years, because that means you're not converging enough. Probably you're not probably learning a lot within same company.

But if you spend three, four years, you are somewhat rooted into company, you probably know not just the explicit org chart, but you also know the implicit or structure of the influence networks. You probably are building what people call "social capital."

Go in with a mindset that you're going to spend next three, four years. And then reevaluate, have you escalated enough in your fitness function in terms of height? If you're stuck again, can you move within same org? But startups are usually small enough where they might not have a position for you. So either you create your own new position by doing more work around you or find a new start-up to join.

So I just recommend, you know, maybe spending three, four years committing to it and then really try to "climb the hill" as much as possible within the same company.

Jerry Li: Yeah, that resonates really well, with something that one of our previous speaker mentioned Wade Chambers. He talks about the observation that there are people, constantly switch from one company to another company, try it maybe for a year or two. And they felt stuck, then they didn't want a new company. But over time they don't really get through that. As the example you provided, it's not much convergence yet. Stay too short, but in company now get to the, optimal height yet.

The "Human Capital" framework & balancing the skills you accumulate in your career

John Kim: Yeah and There's a framework called human capital framework. Basically. You're always accumulating three different capitals, right? Intellectual capital, Social capital, and Emotional capital.

So intellectual capital is your skillset, Getting better at coding, getting better at architecture and stuff like that.

Social capital is your like leadership skills... Not necessarily who, you know, but who else knows you in what way? So it's like a page rank of you,

And then emotional capital is understanding human emotions, understanding your own self emotions, how to motivate yourself, how to motivate others.

And what ends up happening is one to two years, you might get some vested shares from your companies. So you're only optimizing for your financial capital.

But you're actual human capital probably is not really developed. One can only devote so much of intellectual capital here and only been there for a year. Because six months is spent on ramp up. And then six months is like, when you're actually really trying to contribute.

Social capital almost non-existent if you're been there only for a year or two. People probably barely know you, or any achievement you've made.

Emotional capital, you're not gathering any, any at all.

That's why I think spending enough time at a company to really accumulate... accrue these human capital before moving onto the next company so you can actually bring something along with you. Because otherwise, when companies poach you to next company, they will offer you a little bit more, maybe more, a little more cash. But you're not only getting financial capital, but you're not actually developing as a human capital.

That's going to catch up pretty quickly. Five, 10 years to career people will be interviewing you and they'll be able to figure out, okay, this person just jumped ship. Collected is it's a, it's like a angel investor at this point! He has portfolio of stocks, but not necessarily the human capital to back up his career.

So that's where the life kind of catches up to you.

Building emotional capital, training for cognitive empathy, & the tradeoffs of agreeableness

Jerry Li: How do you apply your framework to accumulating or raise your emotional capital?

For example, how do you get to the next level of abstraction layer or how do you do divergence in terms of emotional capital?

John Kim: Yeah, that was a tough one. Cause there's a psychological personality, trait or assessment called the "Five Factor Model", which is like why we use the modern psychology academia.

One of the fact that one of the dimensions is called agreeableness. Agreeableness talks about, empathy or compassionate things like that. So being able to understand people, some people are very high at that just inherently. I rank zero. So I, I struggle a lot with emotional capital side of things. I could rarely uh, have empathy with people just emotionally.

So people who are high in these traits let's say if you see someone else's crying, they can easily cry with you, without even knowing the reasons. Cause their mirror neurons can mimic those behaviors. Mine doesn't work that way. I was kind of geeky, socially awkward engineer early in the days.

So there's other parts of empathy called cognitive empathy. Basically, it's being able to simulate putting yourself in that person's shoes and simulate what the person's going through with the same amount of data that they're seeing, not from where you stand.

So really kind of like first person shooter perspective, you're simulating their behavior. Then you actually feel like you have replicated their experience and you build the empathy. So a lot more cost intensive process.

So part of my journey was training myself, how to go through the process as quickly as possible, because once you experienced it then becomes part of yours and you can actually feel empathy. I trained myself to have that level of cognitive empathy where like, "Okay, if I were in their shoes, let's first assume that person's right. First assume that I'm wrong. Let's see how I can prove that this person is right by gathering the data from that person's perspective."

So once you have enough of that, you can start to actually have influence on these people because you actually empathize.

The other thing is imagine visually that you're sitting next to a person. You're not sitting across the person. Who you're sitting next to the person looking at the same direction. Like, "Hey, I'm here with you. I want to help you. I want you to become successful. I'm your partner. How can I help you?"

So it kind of aligned the vision because the other person will feel it. If you're feeling like you're going to get taken advantage of, and short-term maybe, you know, there could be winner losses, but in the longterm people figure out. People are generally smart. Our brains are smart enough to figure these things out.

So really having that person's interest in heart and assuming again, you're wrong. I think those tend to result in good kind of emotional capital over time. So it takes a lot, I think a lot of training for people like me, who didn't really have the gift in the early days.

Jerry Li: Yeah, I can emphasize on that as well.

The training is that for making a habit, to apply or going through the process, almost subconsciously to get more empathy when you have a conversation or have a disagreement? Or it's the fundamental ability to empathize?

John Kim: Yeah. that's the beauty of this personality assessment is that it kind of tells you about... you're early childhood days are really formative to your personality development, right? Like whatever, your first three years of life after this kind of hard to change. Cause any complexity system, like human beings a complex system. Right? So whatever you're kind of set out with. It really determines the overall trajectory of your personal development throughout your life. And that's really set in the first couple of years, plus whatever genes you have.

So it's about putting a rigor and process to train yourself. The beauty is that we're like a neural network, right? initially is setting up the framework and getting the right data. But once you have the data in the model trained, it becomes a lot more efficient as you progress throughout your career, to have to empathy a lot quicker and have a richer empathy because you have the rich data. You have built a good model through a disciplined process. Then you'll be able to have a much more authentic interaction with people.

It's not like you're calculating every single time. "How do I build empathy?"

It's like, you can, have like, let's say a decade plus of experience. Then you will be able to at least have some empathy with the category of people they tend to work with.

Now, if I go to some random industry, like as they call it arts and music... I will be starting from scratch. Now people with high emotional empathy will, can get in there, build immediate relationship. I have to go in there and work my ass off to get back to where we are today, where I am today.

So that's, for me, that's why it works in technology because I do deal with engineering a lot where I feel more familiar with. And then I have built that kind of dataset or train my brain to work in this kind of capacity.

Jerry Li: But the important thing, now you have a process in place. You had awareness and playbook to intentionally shorten the gap as you navigate.

John Kim: Yeah, and there's actually a cost to being high in agreeableness too. think agreeableness is negatively correlated to social and economical success. Mildly. So it means that if you are too high in agreeableness, you'll empathize with so many people you end up becoming not be able to make tough choices or tough decisions, because you know what this person is going through.

How can you make this decision for this person like this? So as a CEO or any as any kind of executive leader, you sometimes have to make those trade-offs right? For the better of the company or for the customer. So it's, it's a hard problem.

Again, like convergence and divergence, you want to have enough of a balance of agreeableness or disagree so you can sometimes, switch the context and make those tough choices.

How to manage expectations & communicate with stakeholders when you need to pivot

You've mentioned making a couple of really hard pivots, how do you balance making the hard choice and also sort of maintaining that cognitive empathy? If it's a really difficult decision that impacts somebody else, do you have a way that you navigate that conversation in your head when that happens?

John Kim: Yeah. It's all up to expectation management, right? Expectation management for our customers and users, for the employees, the investors stakeholders, and even potentially your like family members and friends who might think you're doing X and all of a sudden you're doing Y... they're like, "Wait, are you struggling?!"

So there's a multiple stakeholders you have to manage.

So what I try to do is I try to put together a timeline... Who to communicate first and when, and what are the signals they need to build comfort around that. And also understanding the other person's personality too, right?

Let's say... I'll just use Meyer-Briggs cause it's better marketed. Well, less, less, probably reliable as a model. Well, let's say someone's like high P perception and high N and usually like... let's say called the MTP. Like whether it be, I R E versus someone who's like S TJ.

STJ needs a lot of data, a lot of heads up. They never likes to be surprised. They don't want big, quick changes. They'll panic, they'll get upset. NTJ, so I kind of like understand both sides of our a little bit. NTPs on the other hand, they're completely okay with change. They'll adapt with that really quickly. So also has a pros and cons obviously.

But when it comes to change, let's say your investor is a stereotypical STJ. You have to really manage your expectations early on. Like six months early on, "Hey, these are stuff, but we're not pivoting just yet. I'll let you know when we see more signals, but we're still on our path of doing original thing..."

Versus NTP's like, "Hey, we found this exciting opportunity. Look at this cool data! Users are responding!"

It's like, "Oh, let's do that!"

So you have to kind of understand your key stakeholders. Thankfully, you're not dealing with 20 investors at this point, you're dealing with maybe two. Maybe up to three. So you can kind of personalize your approach. But as a whole, of course you want to set up framework. You want to optimize for as a minimum amount of shock. So you probably have to give a lot of heads up early on.

But internally, probably your internal alignment happens first too. Cause you actually have to execute before getting any form of signal. So you start with internal. "Hey, we have this hypothesis. We have this data. We have this feedback from your users. Do you want to test this out?"

You work towards that a little by little. So that by the time you announce, "Hey, we're we think we have enough information. Let's make the pivot."

Nobody on the inside is surprised. Nobody on the investors are surprised. And your friends and family can be managed little later on. But the key stakeholders for actually going to contribute to building your company.

The expectation timeline I tried to put in it's about six months in general, because in psychology or physiology too... body takes about three to six months to adapt to a new change, right? The habits and the new ways or whatever that is.

So I try to put in a mental model of like six months, period. How do I backward engineer, what are the things I need to prove out, communicate over time? So that kind of have worked out, relatively well for our pivots.

Patrick Gallagher: Well, I know we're gonna, dive in a little bit more specifically into some of those pivots...

How John applied these principles to make career decisions and pivot his company

You've laid out: divergence and convergence, abstraction layers; you talked about cognitive empathy and a few other different principles of evaluating...

I was wondering if we could transition to do a couple of case studies of key inflection points in your career to illustrate how some of those different principles impacted your decision-making.

You've talked a little bit about the example of making the transition from professional gaming to your involvement as a, as a developer in your first company.

Can you speak a little bit more about how some of these principles have shown up in the early stages of your career transition and changes?

John Kim: Yeah, to be honest, like gaming too, that was more of a outside milestone. Cause I was going through school. I went to finish this study. So there wasn't like particularly convergence divergence model that I applied.

This really model I try to apply it around the beginning of two thousands, because I think I got aware of this complexity science and all these frameworks around year two thousand three and four. Is where I started to educate myself and got started consuming a lot of books on evolution, life, and all those things. So I tried to apply that.

Back then was more around again, the framework of, "Am I creating something? Am I consuming something?"

There's a famous quote by some jazz artists saying you're either appearing or disappearing, right? You only have two choices. So am I consuming something? Am I creating something? I want to create more. So that was kind of my, framework. In general, I try to pick my battles carefully.

If you think about my model... historically, I've been a highly convergent person, right? Professional gaming. If I pick a game, I'm not going to quit until it hit number one in that game. I was the number one player in whatever, Duke Nukem 3d back in the days in Korea, too. So it's like I would never ever give up.

Now, what I realized is that there were professional players, like Fatality, who quickly moved on to the next game, like Unreal back in days Unreal 2003. He moved on to other new games and saw a lot of success there. Now I start to see that pattern with some of the other games too.

Players who were really good at Quake, when Counterstrike came out, they immediately moved on and really completely dominated the game. So I'm like looking at those opportunities, like when the new platform new market emerges... the first one to actually go in, but there, they have this unfair advantage because they're already good at other first person shooter games. And the skills that you learn from other games actually do transfer pretty well in FPSs versus MMO, you can't really bring your character to the next game. So you can carry your skills around.

So I found that to be an opportunity to go for the next game. That's why I also dove into Unreal Tournament. Instead of continue playing Quake and stuff like that. Which really gave me that an unfair advantage.

Now kind of switching over to our company, the initial pivot wasn't necessarily because of the convergence and divergence model. Cause it was kind of the financial shock, was the ultimate trigger. It's like inverstors "Say we're not gonna invest in your company. We can't cause this industry, if you're not generating revenue, we can't!"

But gaming was a proven market in at least in the Korean startup ecosystem. So investors kind of say, "Hey, if you come here, we'll invest."

And this is a industry that I knew extremely well because I was already highly convergent. I would say at the peak of the mountains, in that field. I knew everyone in the industry. I could hire good people. So again, that gave me the opportunity.

But over time, what I didn't enjoy was I knew the product that I'm creating is not helping solve problems. It's making people lives fun, but not, not easier. So I want to solve problems instead of making life more fun. So I kind of pivoted wanting to kind of get out of gaming. That's why, when the opportunity came, we decided to sell.

Now with Sendbird it was a very, very conscious pivot using this framework because we were measuring metrics, right? Engagement metrics. We were looking at the metrics. We were looking at the dollar we spent amount of hours we spent on improving the product. Experiments we're doing.

The metrics where if you had a linear progression in terms of input and output, at least if your output is linear to your input or slightly higher, you can have exponential of curve. But if you feel like whatever your input is, if your output is starting to, like plateau a little bit... in every direction, you know, you kind of are stuck in the local optimal. You have to either completely pivot your product or actually get out of the product completely.

And, because internally our motivation, we're no longer really passionate about this particular project, we decided to completely actually get out of that product. But thankfully by the time we already had enough data that there was a better hill that we could climb much faster.

So we applied that framework pretty rigorously. Uh, again, kind of going back to the example of, do you want to be a people manager? Do you want to be an executive?

Actually surprisingly, you probably can talk to all the other founders about it. What's surprising is a lot of early stage founders as they scale, sometimes they don't enjoy what they do. Because they no longer feel like they're doing real work. So on the side job, they start creating their own pet projects, coding for fun at night, stuff like that. They're going to opposite direction to abstraction, right? They want some concreteness. So they want to hold onto something.

The reason is the further away you are from the concreteness and you move up the abstraction layer, your feedback cycle become a lot more indirect and a lot longer. I think about BizDev versus selling to small customer. Small customer, it's a quick sales cycle. You sell, you get commissions really quick. Biz dev takes two years to nurture a relationship. Never know when it's going to happen. Also similar with fundraising, although fundraising nowadays are fairly quick. There's so much information asymmetry so much indirectness. Feedback loop is very very indirect, and it can be very, time-consuming.

Not a lot of people okay with that. Actually, most people will struggle or feel really stressed by that. That's when people actually decide to go lower in the abstraction layer. And that's okay!

You learned something about yourself, so people should continue to figure out "is it okay if I lengthened my feedback loop? Is it okay if I work with indirectness and ambiguity?"

That's okay! You can continue to move up. But if that level what you're doing, start to feel uncomfortable, then maybe that's the right level that you want to operate for the rest of your career. And that's okay!

Patrick Gallagher: The awareness of understanding where you're operating within the abstraction layer, it seems like such a powerful idea because I'm now reflecting on different moments in my career where I would seek out some of those more direct opportunities to get that direct feedback loop and almost that validation that what I'm doing is fulfilling or valuable where you don't have the same immediate return on "Is this working out?"

And also quickly, I just want to relate to the competitiveness that you had mentioned because my family, the saying is we are fierce competitors, but oftentimes is that things that don't matter and when other people aren't competing.

And so we have kind of a funny thing with the family...

John Kim: One of the Bill Gates book had a episode about where Bill Gates used to be hyper competitive. When he would invite other guests to his house, they would play some silly game, but at one point he would just get so lost in the competition. He'll start saying, "Oh, the rules are not fair. Or that person cheated!"

And completely ruins the mood entire guests cause he wants to win. And I think people who are in their edges and their entrepreneurship or whatnot are somewhat fiercely competitive.

Now they, over time, they have the perspective to understand where, unwise to compete in every single thing in life. So they pick their battles. But it's something that is a learned skill almost.

How to pick careers aligned with your happiness and motivation

Jerry Li: How do you pick the right battles?

John Kim: That's where you have to do a little bit soul searching. I think there's a good framework, intrinsic motivation called AMP or ramp like relatedness, autonomy, mastery, and purpose.

I think ultimately it comes down to looking at your past dots. Like in the Steve Jobs talk about connect the dots. Look at your past patterns, and understand the fundamental, the rules or protocols that you actually gravitate towards.

For instance, let's say I'll give you one example, right? There are engineers who are technology first. And they're also engineers who are customer or problems slash market first.

So engineering who are technology first find a new novel technology, they want to apply this everywhere because it's so cool.

Engineers who are more customer market first want to see a problem in the market, or want to help out this customer and they've backward engineering, and try to build a solution for that. And there is the almost complete opposite trait.

And I think in general, people tend to become more customer first over time. But in the early days of engineering, those two traits tend to be really, really bifurcated, almost. People have a bifurcation of those traits.

So I think it really depends on understanding what you gravitate towards and pick the careers that really motivates you or are aligned well to your happiness.

Because ultimately you can't really lie about your own happiness. You can choose to mimic someone's else's career for a short period of time. But if you do that for three, five, 10 years, your soul's going to die one day. And you'll be one of those cogs in the machine, just moving through inertia, working for paycheck after paycheck. And now you have to convince the rest of the world why that's ok and why that's true. There's no such thing as dream. You should never pursue risks. You have to justify your choices...

Don't be that person continue to fine tune the alignment and be self-aware get feedback. And then see if you can find your own... whatever your own trait that aligns with what you do. And of course it can't always be aligned, right? No one can. But at least directionally, if there's a line that at least you have something to hope for and, long for.

Patrick Gallagher: Relate to that a little bit, the framework that I've used for my career is applying Jim Collins' "Hedgehog Concept" to assessing and evaluating different opportunities. And the simple framework is... what can you be the best in the world at? What drives your economic engine and what are you passionate about? And you find the intersection of that, and that's your hedgehog concept.

And so for me, that's been like a lifelong sort of testing and refining of, are these things that I'm passionate about... do I love them? We'll test it. Or identifying the opportunities of, "Can you be really good at this?" I've sort of amended the question to be, being younger in your career where you still have 20, 30 years left, you probably aren't the best in the world at a whole lot of things, but you can sort of reasonably make a bet that... "Given the investment in time, could I be the best in the world at this?"

And it reminded me a lot of how you assessed the different jumps to the different video games in that assessing the opportunity of, "Could I be the best based on the given skill sets and competencies that I've developed?"

Under this game and in transition. I just thought that was really great.

How to pivot your career using the “2PM” framework (people, product, market, money)

We're getting close to the end of our time. I wanted to ask you two more questions I'd love to talk about Smile Mom, transitioning to Sendbird.

Your current company started off as a social network for mothers. Now it's the number one chat API in the world. Why did you make that pivot? What were the principles you use that really set the foundation for that change? And how can those principles be applied to somebody as they assess their own career pivot and change?

John Kim: So when I manage any startup, I look into what I kind of call the 2PM framework: People, Product Market Money. And you want to make sure that those four dimensions are always being managed well. That's kind of how you run a company.

Now, when you pivot, you have to pick one of those pillars. Now you can't pick money because money is a scholar value. It doesn't have direction. But the rest of the things do have direction. You hire a certain set of people that have certain set of qualities and traits and skills, right? Whether it be market you're going for a certain market. You're going for a certain customer. That also have a direction, a certain nuance to that. Product to you might have a certain IP or technology that you built.

Now, you have to pick your pillar when you make the pivots. I kind of thought about that. And then what is the least lowest risk pivot is pivoting through the market. You'll already know the customers you'll already know their problems they're going through. You're just trying to figure out a different solution to that same problem or same market opportunity. This is probably what I think would be the lowest risk.

The product pivot is something like, "Hey, we are pivoting our product, but we already have some foundation of IP or technologies that we can reuse."

There would be people like, "Okay, forget market. Forget product. Our people can do X. So let's just do that!"

So if you think about my first pivot from during Paprika Labs from going from web 2.0 to social gaming was completely based on people. Wasn't the market. We were going from different market. It wasn't a product. We threw everything out. The investors looked at us like, "Hey, you guys know games, build games so you should just make games."

We were pivoting based on people. This has the highest risk except for money. You're just hitting reset on everything else. So thankfully it worked out. Sold the company, make money, stuff like that.

Now, second pivot was more on the product pivot. It wasn't a market pivot cause API is not in serving the mom's community or local social network. We pivot from B2C to B2B. But, the core IP we built was based on the technology we built for our own applications. We already had the IP. We had a foundational technology that we were working on. We also knew we had built this Czech technology, multiple times in our previous gaming company, too. So this is an IP that we understood really well that we could pivot using. So we kind of used that framework.

Again, we're tracking the metrics of whether it be daily, active users, monthly active users, and all the other user engagement metrics to start to see that really plateau, whatever we did started plateau.

So what, are the factors we can use a pivot? And we realized that all of our co-founders and employees back then except for one person was male, living out of Korea. This Moms community app was US moms. So this hindsight is quite clear that we're probably not the best team to build that for the U S moms.

Okay. But maybe the market we're not super passionate or maybe it's a market that we don't understand the best. We can't be number one in this... hindsight. Whereas the technology we've built chat multiple times already in the gaming company. We built this chat again, having evaluated all the solutions available out there. So we know where they fail.

So what we built was actually a superior solution then to what's available in the market that day. So we pivoted using that pillar.

So I don't know how to translate to career choices... but I think kind of looking back if you're an engineer, Would you want it to pivot using the same market? Do you want to go after the same market? Let's say you're building dev tooling, or let's say you're going after to developers or certain community or B2C, whatever that is.

Do you want to go into a different company that is kind of targeting similar market that you understand really well. But you want to solve a problem for? Or do you want to concentrate on a technology, a certain IP. Let's say you're a backend engineer and you don't care what industry you're in, but you really want to work on scaling your backend. Then you just figure out whatever the company that has the biggest backend challenges. You apply for that.

And then you, might want to actually pivot on your personal, like, "Hey, you know what? I don't want to code anymore, actually like spending time with people. So maybe I want to switch my career to let's say solution engineering or someone else like developer advocate, so that I'm still kind of connected to the coding that I can leverage off of. But I can spend more of my time talking to customers and spending time with them."

So I probably use that as a tool to introspect myself a little bit.

Future founders: Why you’ll be happier making 10 year career decisions & quick pivots

Patrick Gallagher: We have several engineering leaders in our community contemplating starting their own software company. What would you say to a future founder considering a transition away from their current career and making that pivot to becoming a founder?

What would be your advice and first action for them?

John Kim: Well first is think about if I want to do this for a 10 year period. I mean, of course that's the advice that a lot of other founders and investors would give. But I sincerely recommend it because when I look back on all the choices I made... gaming company, the pivot, of course we did it to survive and thrive, but ultimately my heart wasn't in it for 10 years. Cause I was already done with gaming. So when the opportunity arose I sold it.

And people say serial entrepreneur, it just means that they haven't really found the one that they want to do forever. If you look at Bill Gates or Steve Jobs, they have like one line or two lines. One is company, they're just philanthropy, right? There's like nothing else.

So pick something that you can devote your life, hopefully a 10 years of life into. Usually aligned that with market product and yourself, the people. If you find that, you'll very likely, you will almost never give up. And that's going to give you a lot of opportunities. Once in a while you get that chance to win.

And then when you're going in there, I think about the landscape again, like how can I move up this mountain and figure out what the landscape looked like quickly? And when you're blindfolded, how do I traverse this landscape quickly and figure out what the best hill to climb as quickly as possible through whatever minimum viable product.

Because what ends up happening is people will buy all the gears. If you're going to a local hill,

let's say in the Bay Area, buying all the gears for Mount Everest. You don't need any of that. You just need some shoes. good, whatever. A jacket. You start climbing and see if something, is there.

A lot of people end up spending so much time trying to figure out doing analysis and buying all the nice gears, spending a lot of money on that. Just figure out if you can climb. Pick a hill, climb faster and see what that feels like. Be open to making quick pivots early on. Cause it's a lot harder to pivot way later in the company's journey.

Patrick Gallagher: Thank you. this was awesome. I'm assessing my life through the lens of all of these different frameworks and it's revealed a lot of opportunities where I feel like I could have made better informed decisions and a bit more clear.

And the metaphor of being blindfolded on a hill and figuring out, how to climb that as fast as possible I think it's such a powerful framework. So this was absolutely incredible, John, thank you so much your time.

John Kim: Yeah, thank you for having me and hope this is helpful to the audience!

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