The Twenty Minute VCJason Citron, Co-Founder/CEO @Discord: The Untold Story Behind Scaling to 200M Users | E1230
EVERY SPOKEN WORD
115 min read · 22,966 words- 0:00 – 0:51
Intro
- JCJason Citron
That period for us when we went from 200 to 1,000 in basically two and a half years was the moment in time when I think I made the most management mistakes at Discord. I hired a bunch of executives and, and set the vision and delegated that work to them, and everything ground to a halt. Words today that trigger me, which I think are shadows of this, are words like empowerment, alignment.
- HSHarry Stebbings
Ready to go? Jason, I am so excited for this, man. It is such a pleasure. I've heard so many good things from Danny Rimer at Index for many years, so thank you so much for joining me today.
- JCJason Citron
Yeah. Thanks for having me, Harry. Great to be here.
- HSHarry Stebbings
Uh, not at all. But listen, I have interviewed 800 of the best CEOs of the last probably 10 years, and
- 0:51 – 3:49
How Gaming Skills Translate to Leadership
- HSHarry Stebbings
a commonality amongst many of them is they excelled at gaming, ironically, in the early years of their life. And I wanted to ask you, why do you think gaming is such good preparation for CEO-ship?
- JCJason Citron
You know, game, games are like these little sandboxes of life, right? And you know, you think about what you're doing when you're playing games. You're, um, you're, you're encountering challenges. You're trying to figure out how to solve them. You're failing. You're thinking about what mistakes you made, how you could do it better. You do it again, and you keep doing this over and over until you, you have overcome your challenge. Like, that's growth mindset, right? Like, isn't that incredible? Like, we're... Like, kids are, are experiencing this, you know, just by playing games. Or you think about, um, playing games w- with your friends and against other people, and what do you need to do? You have to learn how to cooperate. How do you divide up tasks? Who steps into a leadership role? How do you be a good, a good follower? When do you trade those places? How do you learn how to be a good, you know, not a sore loser, not a sore winner? Like, these things all happen when you play Fortnite. (laughs) So like, games are such amazing, um, little simulation sandboxes to get to ex- to, to interact with these things that are basically like microcosms of real life, and you can learn these skills in safe places. And my guess is there's something to do with being able to, to do those things over and over and over and over and over again in a way where you don't even realize you're, you're learning those skills 'cause you're just having fun, that may translate to the kind of things you need to do to run a company. I, I don't know. I mean, c- certainly I did.
- HSHarry Stebbings
You mentioned levels there. Uh, in games you have levels, it gets harder, generally the way that games work. If we align that parallel to company building, which level of company building was the hardest? And what was the cheat code that you used to break it?
- JCJason Citron
Oh, wow. That...
- HSHarry Stebbings
Swahili is like, "What the fuck? This wasn't in the schedule." (laughs)
- JCJason Citron
(laughs) No, that's a great question. I mean, each, each level brings about different challenges, you know, and I think one of the hard things about being, being a CEO and, and being... Probably being a CEO, maybe also being a founder, is like, you know, each time you get to that next level, like, you haven't done it before. So by definition, you're just like constantly figuring out how do you work through these new challenging dynamics? And, and, you know, for different people, I'm sure different parts of it are easy and hard. Um, but I don't know, it's just, it's, it's, it's always hard. (laughs)
- HSHarry Stebbings
Was there one where you felt like, "I'm, I'm, I'm not equipped for this?"
- JCJason Citron
Well, frequently I would encounter situations, um, and it still happens, like almost on a daily basis, where I'm like, "I don't, I've never done this before. I've never seen this before." But the, the one thing that I, I have confidence in myself and my team is that we can figure things out. You know, it co- it comes back to that growth mindset. When I'm faced with a challenge that I don't know how to solve, I can usually figure it out if I work hard enough. Um, so I, that's just kind of my mentality with everything is like, "We're just gonna figure
- 3:49 – 5:35
The Impact of Financial Cushion on Founders
- JCJason Citron
it out."
- HSHarry Stebbings
I think that that mindset is helped when you're not existentially worrying about rent, actually. And I've thought a lot about how money influences an investor's mindset.
- JCJason Citron
Mm.
- HSHarry Stebbings
I'm interested, you, you sold your prior company for $104 million, to be precise. I love the, the four. Like 100 wasn't quite right. Yeah, well done for pushing that one. Um, my question to you is, do richer founders make better founders? And how do you think about the financial cushion benefits?
- JCJason Citron
It, it certainly helps to s- i- in a sense that every successful company along its journey gets acquisition offers. And so by having a cushion, it made it easier to turn down offers 'cause we could just go for the big, you know, outcome and, and try to build a generational company. So i- in that regard, um, it, it does make it easier, I think, to build a, a, a more impactful, more important company. But I think the real, the real impact from being a second time founder actually has to do with the levels and how there are a lot of levels I had already played once in my previous company, so there were things about building my second startup and about building Discord that were easier in the beginning 'cause I had done them before.
- HSHarry Stebbings
What was harder the second time round? Fundraising's easier, hiring's easier. What's harder?
- JCJason Citron
The second time around, w- what was hard, I don't know if it was harder, but what was hard was still cracking product market fit, you know. Like, we had an insight around the shape of the business that we, that, that I wanted to build and the types of products we would make, but getting the specifics right are just hard. Even when you know what you wanna make, it's just hard. And so I don't know that it was harder, but it was, it was hard, and I was able to focus more on it because I wasn't so overwhelmed by like, how do you manage
- 5:35 – 7:28
The Core Idea Behind Building Discord
- JCJason Citron
25 people?
- HSHarry Stebbings
What was the first unique insight that you had with Discord? I always believe that when you go into an investment, you have to have a thesis which can be proved or disproved. When you go into founding Discord, what's the thesis?
- JCJason Citron
Yeah. The, the thesis back in 2012, at the time my, my sense was the, the, the way you built a durable company in gaming over time was you actually needed to have some kind of established distribution advantage. And so I, I kind of put these things together and thought that like, you know, the, the shape of the company in the future would be a group chat app focused on gaming, you know, that helped developers bring their content to life.Um, and that's essentially what we're doing (laughs) now 12 years later.
- HSHarry Stebbings
Can I ask you, when you went out to speak to investors in the early days, what was the number one reason why they said no?
- JCJason Citron
Well, in the very early days we started... The, the path that, that I, that I sort of took us on, um, had some twists and turns and, and at the very beginning what I thought we needed to do, and the approach we took, was actually we started by building a multiplayer game. A cooperative and competitive, like a team-based competitive game on mobile. And, um, my, my thought was that we needed to build this game to kind of bootstrap the, the network of the group chat app. And, and so a lot of investors said no 'cause they didn't think the game was gonna be successful, and I, I suppose they were right. Like the game ha- had, had a really nice following, I was very proud of it, it was called Fates Forever, um, but it was not gonna be a venture scale business. Like content is tricky, it, it wasn't a hit, and it didn't amass the kind of following that we needed to bootstrap a network, but by going through the process of building the game, we identified, um, like a path to market with a group chat app that didn't need a game to bootstrap it, and then so we built Discord actually in 2015. Um, so the journey, it, it's one of those funny things where we were like stubborn on the vision, but flexible on the details, and it all sort of worked out over time, and, you know, as we keep talking, that, that's kind of the theme of the story (laughs) .
- 7:28 – 11:12
How Quickly Did Discord Find Its Market Fit
- HSHarry Stebbings
Did you have immediate product market fit when you launched the group chat app, V1?
- JCJason Citron
It was pretty fast. It was pretty fast. I, I wouldn't say immediate, but it was pretty fast. You know, we started working on it January 2015 and within I'd say two months some of our friends were very excited about it. But we didn't really have any users, but it was pretty clear they wanted to use it, it just like wasn't exactly correct. So we, we, like we re- we, like, rebuilt the voice chat engine three times, you know, for example. But I'd say within three or four months we had like 20 DAU that weren't us.
- HSHarry Stebbings
(sighs)
- JCJason Citron
So pretty quickly (laughs) . But 20 is small (laughs) .
- HSHarry Stebbings
Do you... So do you agree with the principle of build it and they will come?
- JCJason Citron
No, I do not. I think the Discord story was actually, I think, uh, a perfect example of how build it and they will come may not always work. Now sometimes, maybe it works sometimes, but at least for us it didn't. And, um, you know, when we got to this place where we had 20 DAU we actually were having a hard time figuring out how to get more people to use the product. We were like, "How do we get the word out?" 'Cause everyone was actually very skeptical about a group chat app for gaming. People would, would say, "This is the dumbest idea ever. Like no one's gonna use this." And even people who played games, some- many of them thought like, "Why would I want this? I already have, you know, whatever app I'm using." And, and so we were having a hard time getting other people to try it, but we ended up figuring out, um, kind of a- a- a- a way to get the word out that people responded to positively that caused them to start trying it, and then it started to grow on its own. But there was like a period of three or four weeks where I remember we were sitting around thinking like, "Well, we like this, but maybe no one else does."
- HSHarry Stebbings
Well-
- JCJason Citron
Like we had built the product and we just hadn't figured out how to get the word out.
- HSHarry Stebbings
What was the unlock?
- JCJason Citron
The unlock for us was, was inviting people to give feedback on the app. As opposed to saying like, "Try this thing out," like we're selling it to you, what we actually did is we went to the Final Fantasy XIV subreddit on Reddit where there was a new expansion coming out for this game, and we got one of our friends to make a post on the subreddit basically saying, "Hey, I'm trying out this new voiceover IP app, what do y'all think about it?" And then they, they, they basically said, "I found this thing called Discord. What does anyone think about it?" And we went into that, that thread on Reddit and posted a link to a Discord, uh, server, which is like the group chat, we call them the servers, where me and my co-founder were hanging out, and people would, w- like found it on Reddit, clicked on that link, went into the server, and then they were talking to us and trying it out, and they went back to the subreddit and were like, "Hey, this is pretty cool. I met the devs, they seem pretty cool." We got 50 users that day from that post, and then that 50 turned into 100 the next day, and it, and it sort of started to snowball, and then we kind of tr- did this playbook a little bit for like six months and, and, and that was basically the beginning of how, how it started growing.
- HSHarry Stebbings
Did you ever have a plateauing of growth where it slowed?
- JCJason Citron
Yeah. It, it, it's not all been, been, been up and to the right.
- HSHarry Stebbings
What do you, what do you do then, Jason? Like do you go back to the drawing board and go, "What features can we do to supercharge this (laughs) ?"
- JCJason Citron
Yeah, it's a combination of, of, of thinking about how do you continue to make the existing product more useful and, and, uh, and, um, better for the people who are using it today for what they're trying to do, and then you gotta try to think about like how do you make it, you know, more approachable for people that aren't using it today? And, you know, these are some of the areas where we, you know, during the COVID years kind of branched out in a way to, to, to try to help be more useful to so many people because of what was going on during COVID, and over a few years sort of following that, realized that we kind of went down some dead ends a little bit, and, and that people were not resonating as much with some of the features we were building, so we kind of pulled it back in to f- to refocus on gaming
- 11:12 – 14:27
Reflecting on Discord’s Growth Journey
- JCJason Citron
this year.
- HSHarry Stebbings
Do you regret the expansion into more verticals to attract more people? And did you learn anything from that, like audience creep?
- JCJason Citron
I do not regret it. It introduced Discord to a lot of people, and many of those people continue to use, to use Discord today. So we, you know, while we, we went in a bunch of different directions to try to be useful to all those folks that maybe, um, didn't yield as much of a, of a, of a business impact that I was hoping, we certainly, uh, our business grew tremendously during that period and I learned a lot about how do you manage your company at the next level. You know, we went from 200 to 1,000 employees in that time period, which was like totally crazy. The whole founder mode thing is interesting. I kind of went through all- my own experience of that, and now realizing, you know, other people had similar experiences was kind of interesting. Um, but yeah.
- HSHarry Stebbings
I, I have to touch on that. 200 to 1,000, the scaling there, incredible. Um, PG obviously f- famed for many things, but, you know, m- obviously r- this blog post has been incredibly viral. How do you reflect and think about founder mode when you reflect on the journey with Discord and the 200 to 1,000?
- JCJason Citron
Yeah. That period for us when we went from 200 to 1,000 in basically two and a half years was the moment in time when I think I made the m- the most management mistakes at, at Discord. And a lot of it is, is where e- basically I hired a lot of people and been f- and because it was a new level that I hadn't really, you know, dealt with before, and it was hyper-scaling and all this craziness, I kind of followed the best practices and I hired a bunch of executives and, and set the vision and delegated that work to them. And, um, everything ground to a halt. We did a lot of things that didn't end up resonating with our customers. And, um, I have, you know, s- I-I think I, I kind of realized this may... at this point now maybe almost two years ago. It was like a co- it took a couple years and then I realized that... and sp- I went on this journey to try to fix it. But it was hard because it... I was essentially trying to undo all of the best practices that everyone thinks that you should be doing when you're running a company.
- HSHarry Stebbings
So what, what, w- tho- that- those being delegation, hiring execs, you've seen it before. What else? Anything else?
- JCJason Citron
I don't know that I have like a cataloged list in my head of things. But, you know, words today that trigger me, which I think are shadows of this, are words like empowerment, alignment. Um, you know, like-
- HSHarry Stebbings
M- might, my team have a drinking game-
- JCJason Citron
(laughs)
- HSHarry Stebbings
... where the more the person says alignment, the worse a CEO they are.
- JCJason Citron
Yeah. I, I, I, I, I now say alignment is a four-letter word. Um, like I don't want alignment.
- HSHarry Stebbings
(laughs)
- JCJason Citron
I want, I want, I want highly opinionated people making decisions and them being accountable for them. Right? So this is like, you know, some of this stuff that I think people get caught up in.
- HSHarry Stebbings
And so was there a realization moment for you, "Oh, shit. I've become manager mode. I need to go back to founder mode"?
- JCJason Citron
I mean, I didn't have those words for it, you know, this was a couple years ago. But there, there, the realization for me was like, w- we are not shipping great products anymore. The, th- it's not coherent. The stories we're telling don't make sense. I feel like it's hard to get things done. I feel like I'm fighting against the company, not with, not with the people trying to achieve something. So it just like felt broken.
- 14:27 – 20:44
Approaching Delegation
- JCJason Citron
- HSHarry Stebbings
Just breaking them down. Delegation, something that's like told for years, th- to gain scale, leverage. How do you approach delegation today? What do you delegate? What don't you?
- JCJason Citron
Yeah. So, so delegation is still very important, and this is why this stuff is a little bit tricky, is th- it doesn't mean micromanage everything, don't delegate anything, don't give people space to be creative and make... Like, it, it's not that you shouldn't do any of these things, it's that you need to be careful about how you do it. So for example, now I, um... I'll, like I'll give you an example. So today, I have a process where the way I manage the, the, the work is I essentially, um, when we do our, our, our, our, our sort of plan for the year, instead of me sort of giving a high-level, you know, vision of like here's the kind of outcome I wanna have next year, I will tell my teams like, "These are the problem spaces that I wanna f- I want you to focus on. These are the, the kinds of solutions I'm, I'm expecting to see." And then they come back to me and I literally pick all the projects now. Like I'm literally like, "Okay, we're gon- we're gonna work on, you know, improving reactions like that and we're not gonna work on the, on, you know..." Well, I'm not gonna say, "We're not gonna work on it." I don't wanna leak any features. But, but like, you know, like so I will literally go through and pick all the, all of the, all of the projects now. Whereas like a couple years ago, my team was like, "Oh, we have to be empowered to pick the projects. Just tell us what metric you wanna move." And I was like, "Okay, I guess that's how you run a company." But now, no. I'm like, "I pick all the projects. Um, I'm very tops down on what the strategy is and how we're allocating resources, how these things are sequencing together over time, so it- it's coherent to our users."
- HSHarry Stebbings
How do you think about creating an environment of ownership when one is told bluntly direction like that and they're not making choices?
- JCJason Citron
I think the, the mistake was i- i- pushing those decisions to the wrong elevation in the company. So like when I, when I go to a team and I say, "Hey, guys. Like, I want you to think about how reactions work and how we can make this better for people and here's some specific ideas for how to make it better," what I'm actually saying to them is like, "I now want you to use your incredible creativity and energy to try to explore this part of our, of our, of our sandbox." So they have extreme ownership over, okay, like, these are two or three ideas that Jason has that he really wants us to do. They can tell me they think I'm crazy and then we'll argue about it, maybe they're right, sometimes I'm wrong. I mean, I'm not, I'm not right all the time. But, but also there's a problem space there. And they can explore and ideate and think within that problem space. But then they're gonna pitch those ideas back to me and I'm gonna pick the ones that they're gonna do. So they still get to have ownership and accountability and creativity on like what the work is, but they're not, uh, you know, accountable necessarily for, um, should we even work on reactions now? Like, that's, that's somewhere else in the organization. You know, that might be me or that might be me with a VP or something and, and the VP's advocating for me and I'm like, "Yeah, okay, that's good. Let's go do that." But, but it... the, the mistake was, that I made was y- was delegating decisions to the wrong level of the organization.
- HSHarry Stebbings
How many direct reports do you have today, Jason?
- JCJason Citron
I have seven today. We're a functional organization, so I have like engineering, I have like EPAD which is, you know, engineering and design and analytics and then marketing and finance and that sort of thing. But, but I work with the directors and the ICs. So when we do these product reviews, I have the frontline, like the, the people doing the work actually, um, prepare usually, uh, like Loom recordings, like video recordings, and they send them to me. And I will watch like a 15 or 20-minute walk through of a feature and then I'll go look at the Figma, for example, or read the strategy doc after they talk me through it in a video, and then I often respond with a video recording. And I'll talk for like 20 minutes and give them feedback. And then only if there are questions, do we have a meeting. And it's, it's incredible. I c- I have so much free time and I'm able to give feedback on so many things, 'cause I, you know, I watch the videos at 2X. I can always find time to watch a video. I can respond to the, to the video. And then these meetings where you... You know, I used to have these meetings with like 20 people-... and we'd walk through a product. It was a 45-minute meeting. And then like everyone wants to talk. If I give feedback, people are defensive, "Oh, the CEO's being..." You know, giving feedback. They wanna respond to it. It's like this whole ceremony. It's ridiculous. And so now, like we just cut all that out, and it's been transformative.
- HSHarry Stebbings
Do you lose participation and discussion with that Loom async response, response, response?
- JCJason Citron
Yes, but that's kind of by design. Like most things don't actually need a lot of participation and discussion. Like the team has done a tremendous amount of work, and they're trying to get feedback from me, and the forum of the, of a 20-person product review turns it into like this bizarre ceremony. I actually don't want everyone to talk. I want to give them my feedback. (laughs) And I wanna be direct and kind but I want, but I want to give them the feedback. And then, um, and some of it is just questions, some of it is try harder here, some of it is like I wanna see another version of this. Some of that is like, "This is amazing. Here's the 10 reasons why I love it." You know? But, but the other amazing thing about that is those videos are all public, so if you're not in the meeting anyone can watch. Like there's a archive of me giving feedback on stuff that anyone can watch at any point. So if you miss the meeting, you're sick, any, everyone on the team can, can, can, can, can hear that feedback from you without having to be in the meeting, which improves the, the coordination cost. It just, it goes down.
- HSHarry Stebbings
What is the meeting that is most required for the discussion for the engagement and could not be done in that way?
- JCJason Citron
Sometimes you will have, um, more on the, uh, sometimes there'll be, there'll be situations where you need to have like an expansive brainstorm where it's like we are gonna explore something together. And it's not a presentation. It's not necessarily a decision to be made. It's like we're gonna explore something together. So we'll get in a room, and the creativity and the back and forth, the result of the meeting is like 15 options or, or a wide open idea. Um, I find that those are good discussions. And then sometimes there are discussions where, you know, there's different points of view and you, it's clear that from like sort of the initial sort of presentation and the reaction, there's still things to be hashed out. And then you get in the room, and you have the debate, but you've already had, everyone's already done this back and forth w- so you, you come in fully loaded up on the context, and you can have a really rich conversation and figure it out in, you know, 30, 45
- 20:44 – 22:13
Balancing Bold Ideas & Organizational Focus
- JCJason Citron
minutes.
- HSHarry Stebbings
Tobi at Shopify says, "The job of the CEO is to inject chaos into the organization."
- JCJason Citron
(laughs)
- HSHarry Stebbings
And, and I like that because I fucking do that. But I don't like it because I'm also like, "Hey guys, we're gonna do this crazy batshit idea." And then it's like, oh, that's a load of distraction. Do, do you, which, which side do you fall on?
- JCJason Citron
Uh, I, I have a lot of respect for Tobi. I don't know that I would say my job, I don't think of my job as injecting chaos. Um, I think my job is to make sure that we're creating amazing products for people, and if the chaos helps the organization do that, then I suppose I will do, I will inject chaos. But I think on balance, for me at least, I have not found chaos gets us closer. (laughs)
- HSHarry Stebbings
Do you think the best CEOs are the best resource allocators?
- JCJason Citron
Resource allocation is certainly important for b- as being a CEO, 'cause you know, if you have a, a, a large group of people, um, the first thing you need to do is figure out like how you wanna organize them together and against what problem sets. But I do think that, um, selecting the right problem sets is, f- is probably more important than the resource allocation to some extent. Like if you have the right problems but your resource allocation is sort of wrong, you'll notice that and then you can correct it later. But if you have the wrong problems and the resource alloc-, then the resource allocation can't be right. (laughs) So I, I don't know that it's, that it's like you just have to be a resource allocator and that's
- 22:13 – 29:06
Lessons from Scaling Executive Teams
- JCJason Citron
it.
- HSHarry Stebbings
Problem selection is down to you. It's also down to your execs. You mentioned kind of some challenges in terms of scaling exec teams there. It's a really hard thing to scale an exec team. When you think back to miss-hires on exec teams, what are some of the biggest lessons for you on that element?
- JCJason Citron
There's two things that come to mind. One, one is that hiring execs is, is a bit tricky because by the time you're hiring someone, by the time someone's an executive and they're interviewing for a role at that level, they're probably very good at communicating, and they're very good at talking about the work. And so I have found that actually interviewing execs and ver- sort of r- more senior exe- e- experienced people is really good for getting a feel for whether I would enjoy working with them. C- c- can we brainstorm? Can we debate? Do I enjoy, you know, being with them? But I rarely find that folks like fail the, the sort of eh, uh, capabilities test in, in those kind of interviews. I mean, sometimes they do, of course, but, but I find by the time like, you know, if someone gets to me like they're, they, they come, they're sort of qualified for the job. So the thing is you have to reference check the heck out of executives because it's really hard to fake it for like three years if you work at a company. So when I, what I have, basically what I do when I hire execs now is I meet them to get a sense for like do I enjoy being with this person? Can we, can we debate and, and, and, and have a good conversation? And then I call like everybody I know who, who has ever worked with them to try to figure out what, what they're actually like to work with, and that's where you get the real insights. And w- since I started doing that, my, uh, success rate of hiring executives has, has gone up a lot. And the second thing is then once you get them into a company, um, I have like a whole process that I've sort of come up with for how to integrate them in, and the sh- the short version of it-
- HSHarry Stebbings
How, how did, h- how, how do you do that? That's very hard to do.
- JCJason Citron
Yeah. The, the short version is that I don't expect them to do any work for the first like 60 days. They come in and they just need to learn. I just want them to meet the people, learn what we're doing, figure out why we're doing things, and every day what I expect them to do, I have a meeting, I, I'll set a 30-minute meeting with them every day for like the first 45 days and I want them to ask me questions about the business. Like they need to learn and understand the cont- there's so much context. They need to learn and develop a point of view on their talent, on the projects for their area, and then sort of in the second month start to express some of that viewpoint with me, and then by the end of the third month, like they take over and they're running their team. Um, and I have found this like...... sorta, sorta like learning transition really sets them up for success. 'Cause if you expect someone to come in on day one and like run it, they don't know what's going on.
- HSHarry Stebbings
What are the biggest reasons why exacts become exact mishires? How does it most often go wrong, essentially?
- JCJason Citron
Well, the- the mistakes that I've made are, um, a- actually, they come in and they start changing things right away. And then- and then the people, um, in their au- in the team or around the company are like, "Why is this person making this decision? I don't understand why they're doing this." And like if it's wrong, then they lose credibility and then it's really hard for them to- to get that credibility back.
- HSHarry Stebbings
How long do you give someone? 'Cause in those cases, it's really hard to, I come in, "Thanks for hiring me, Jason. Thrilled to join." Uh, I make a load of changes and the team's like, "Who is this guy and why is he making all these changes?" And it's like, "Well, Jason, you hired me, back me. I'm making these changes." And then the culture just gets worse beneath me. I just continue to make Titanic worse inside the company. (laughs) But you should back me for a while. How do you think about like how long to give versus d- or cut it straight out?
- JCJason Citron
This is- this is one of the other things that I came to learn, which is, you know, when we went through that period of hyper-scaling, I did a lot of like, w- when the executive told me this is how something was supposed to be done, I would always tr- I'm a curious person, so I tried to understand why. And if I really couldn't figure it out and my intuition said this doesn't make sense, I would actually let them do it anyway. And inevitably, I'd say more often than not, it didn't work and I was right. And so now what I've come to learn is that, you know, executives and other people are obv- they're experts in their craft and we should trust them, but if my intuition says that this doesn't make sense, I now trust my intuition and I won't- and I won't support them in whatever they're doing. And- and I won- and I'll be like, "I want you to do it my way and I need you to trust me." And more often than not now, that has actually worked out well because it turns out that the context of the company is so important and I have the context of the company, and the executive is the expert in the craft. And the- and- and the context of the company, like the reasons for why you do things, actually should be the beginning point to derive how you run a team or how- what products you build or what stories you tell, right? You think about sort of first principles, like what are we trying to accomplish is what- where you start, not like what are the tools for some- for some, um, you know, some function or some craft. So, um-
- HSHarry Stebbings
When did you have the strongest intuition that turned out to be wrong?
- JCJason Citron
At Discord, we, in 2000- late 2018, we built a- a PC game store, which I ended up shutting down after like four months. So, that didn't work. Um, so I, yeah, I- I- there's a long list of things where I have made the wrong calls. Um, but I think the- the thing that I've come to learn is that I am still more right than I am than a new executive joining my company. (laughs) Like I still have more context than most people who join, uh, g- given the nature of how long I've been doing this. And- and- and you also, I also learn over time, and I think this is the trick, one of the challenges with like trust your intuition, trust your gut as advice, is like you don't know where your gut is right and wrong. And so, one of the things I've come to learn over the years is the kinds of things where my intuition tends to be right and the kinds of things where my intuition tends to be wrong. And so, when it's one of those things, I give- I discount myself a little bit.
- HSHarry Stebbings
I spoke to many of our mutual friends. I pretty much know all of your cap table. After 2,800 shows, you'd expect me to, so it's at least
- NANarrator
(laughs)
- HSHarry Stebbings
Uh, but they- they said, and I hope it's okay for me to say, they said that, you know, there's so many incredible things about you, but they said you trust more experienced people's recommendations sometimes more than your own, and that was a weakness.
- JCJason Citron
Mm.
- HSHarry Stebbings
Do you think that's fair? And how would you reflect on that?
- JCJason Citron
I think there was definitely a period of time where that was true. And you know, we talked about this a little bit. It's the sort of bringing the executive and- and- and delegating the- the- the outcome to them, but also the- the approach to the outcome. That was one of the hard lessons that I learned over the last few years that is, where I- I- I stopped listening to my intuition on some of these things, and as a result, the, um, you know, a lot of things at the company went sideways.
- 29:06 – 30:57
The Chance To Sell the Company to Microsoft for $12BN
- JCJason Citron
- HSHarry Stebbings
In terms of gut and tough decisions, it's a tough decision. You mentioned earlier, like actually it- it's helpful when you have a little bit of money 'cause you're not tempted to sell early. You had a decision to sell the company for $12 billion. Um, first off, how does that feel, Jason?
- JCJason Citron
It was pretty crazy- (laughs)
- HSHarry Stebbings
Yeah. (laughs)
- JCJason Citron
... to be in that situation. Yeah.
- HSHarry Stebbings
Do you remember where you were?
- JCJason Citron
It was not a short process and there was a lot of things going on at the time. So, you know, it was one of those situations where we- and I have always been very focused on just like trying to make amazing products, tell amazing stories, and build a great company. And, you know, a- along the way over the years, from time to time, you know, we get interest from people and, um, you know, sometimes we engage with it, like, "Okay, like what- what's- what's happening here?" And- and this was, it- it actually began as just another one of those, where it was like, "Huh, okay." And, um, but ultimately, we decided that we really just wanted to focus on creating what we were creating, you know? I- I love creating software and I love solving problems for people, um, around gaming and ha- you know, having fun with their friends, and- and that was the path that we chose to- to stay on, 'cause we thought, has so much opportunity ahead of us.
- HSHarry Stebbings
The reason you sell is 'cause you believe there's more strategic benefit to be had from the acquirer and what it does to your position as a company. Say, Instagram with Facebook, say, YouTube with Google. Did you not feel that was the case here?
- JCJason Citron
Microsoft has been a- a really fantastic partner for us. And, um, and there certainly are things that we could have done together with them that we can't do independently. But, uh, ultimately, it- it was about, um...... you know, you know, controlling our own destiny, I suppose, and, and really seizing the opportunity
- 30:57 – 34:54
Future Insights in Gaming That Deserve Attention
- JCJason Citron
in front of us.
- HSHarry Stebbings
What does no one see or think about the gaming industry in the future that everyone should be thinking about or speaking about?
- JCJason Citron
We're in kind of a tough period in the games industry right now, where after COVID, it's kind of contracting, you know, and, and, um, there's a lot of consolidation, yet it's as big, it's, it's really, really large if you think about how much, you know, money consumers are spending and how much time people are spending and how important games are in people's lives. And I think that while it seems it's both large and also, um, feels kind of like we're in a slump, I think in 10 years from now, it's gonna be so much bigger and so much more important and so much more pervasive than it is today. Um, 'cause y- if you think games... games just kind of follow the trajectory of digital technology, and it seems like, you know, in 10 years from now, there's gonna be more digital technology, more people using devices, crazy new ways that we interact with this stuff, and games are always at the leading edge of how people take advantage of and harness, um, technologies. And so you think about like, how is AI gonna change the creative side of, of game development and the interactive side of game development? And it's just like, we could spend two hours on that (laughs) .
- HSHarry Stebbings
How does AI change the creative side first before we... I've seen many tools that, uh, are addressing different elements of the creation process. In your mind, most succinctly, how does AI change the creation process for gaming products?
- JCJason Citron
I mean, I think it's gonna dramatically lower the cost to create incredible content, which means that if you don't... which means you're gonna get- get... I think you're gonna get games like Elden Ring that are made by teams of like 20 people, not 300. And then it's also gonna mean you're gonna be able to have someone who, you know, an individual person, a solo creator who will be able to make games that they, that they can't make today because it, it takes either five years or it's just too hard. And so I, I think we're gonna find that, that-
- HSHarry Stebbings
Do you worry about what that does to discovery? So I wo- like, I think that's amazing, the democratization, but with democratization comes a massive increase in supply.
- JCJason Citron
Mm-hmm.
- HSHarry Stebbings
And with that increase in supply, discovery just becomes the b- a war. And often in that case, it's just a game of who has the most dollars. Do you worry about discovery being that problem?
- JCJason Citron
I think discovery is already a problem for developers, it's gonna get harder to break through. But I think that it, it's hard to, uh, it's really hard for me to predict how the world will be if there's like 10 times more games and they're all high quality. 'Cause you can imagine when the cost drops so dramatically, the whole business model changes, the whole dynamics change, right? Part of the challenge today is that it's hard to break through and it costs $200 million to make a big game, right? But if the costs were much lower, then you could have games where the subject matter is much more niche and, and then in that world, what happens? Like, you know, i- i- imagine if you had 20 Elden Rings and they all had different themes and they were all as good and they, you know, like you don't need to make $7 billion from making Elden Ring. You could make $10 million or $50 million, maybe it's a great business. So it- I think that consumers are gonna have so much more choice and so much-
- HSHarry Stebbings
Does that not lead to this like incredible unbundling of gaming, this immense personalization of gaming?
- JCJason Citron
I think it leads to, uh, it, it could lead to a lot of personalization in gaming. People still like to play games in community, so I think you're still gonna have situations where like maybe groups of friends will try certain titles or... yeah, I think we see potentially echoes of this if you look at, um, how like video entertainment happens today, like on the streaming services, you know, where you start- you have like, you know, everyone watches... like there are shows that are really popular that no one's heard of (laughs) , right? Because there, there's so many people who watch these things that you can have these kind of more niche subject matter, um, shows. I, I think that y- you're gonna start to see, you, you know, something like that. Music is kind of even more like this if you think about the music industry, how much content there is. It's amazing for consumers, but it is harder for
- 34:54 – 39:35
AI’s Impact on Gaming Products
- JCJason Citron
the creative side.
- HSHarry Stebbings
What is the biggest misnomer or mistake that people have or think about how AI will impact the future of creation of gaming products?
- JCJason Citron
I, I don't know if there's a obvious misnomer. I think that it's really hard to predict what's gonna happen because we're in this world where the, you know, um, in, in gaming there's this i- there's this concept of a fog of war, which is like, you know, when you're playing a game like StarCraft, you can't see what's going on on the other side of the map until you've been there, and so you have to kind of plan without knowing what's happening in the future. And I feel like we're in a moment in technology and, and because of the nature of AI, it's, it, i- i- it's sort of challenging us to reinvent so much about how we do things in our lives, that when I think about, you know, wh- where are the capabilities of AI gonna be in 10 years, it's just like so hard to reason through, to reason through what are the implications of that. Like if we actually get AGI, then what happens? I don't know. You know, like there, there's like a tech tree, you know, a- and, and you can imagine different paths through it that could result in so many different outcomes that it's just very hard to predict. So I, I think anyone who's really certain about what happens is probably wrong (laughs) .
- HSHarry Stebbings
How does AI change the interaction side, how we engage with these games as consumers?
- JCJason Citron
Again, I don't know, but, but some things that I think about which could be pretty compelling are, um, you could imagine how today, you know, you, you might play a, a game, you know, like Legend of Zelda: Breath of the Wild, for example, or Tears of the Kingdom, one of these big open world adventure games where you're a character and you're in this fantasy land and there's people and adventures to go on, that gets handcrafted by a team of people. And, and because the nature of it, uh, it's an amazing game, but there's a lot of repetition for how the sort of structures play out because you just can't make bespoke content for 90 hours in a game like that. But you could imagine if you have AI that like every one of those characters can have a complete backstory, can respond to you in, i- i- in, in, in the totality of all the decisions you've made inside of a game world.... and you could have literally hundreds of hours of bespoke content customized to your experience that just never ends, as long as you want it to go. And, and I think that, you know, being able to explore and play in a, in a, in a game world that you're passionate about forever could be really compelling. You know, uh, you think about like watching TV shows and how it's always bittersweet when a se- when a, when a series ends because you're like, "I'm done being in that world, but it was-"
- HSHarry Stebbings
It's terrible.
- JCJason Citron
"... so much fun to be there."
- HSHarry Stebbings
You get to that point where you, like, ration it out so it-
- JCJason Citron
Yeah.
- HSHarry Stebbings
... lasts longer.
- JCJason Citron
Yeah, yeah.
- HSHarry Stebbings
Yeah.
- JCJason Citron
I mean, I've watched Game of Thrones the wh- like four times over 'cause I enjoy it so much. Imagine if it, like, could never end and it was always great.
- HSHarry Stebbings
(inhales) Does that change the business model of games?
- JCJason Citron
Oh, certainly.
- HSHarry Stebbings
How does the business model change in that world?
- JCJason Citron
Uh, uh, again, I don't really know. But you could imagine-
- HSHarry Stebbings
Ja- Jason, you, you, you would be a ter- I, I, I've got to interrupt you. You'd be a terrible venture capitalist.
- JCJason Citron
(laughs)
- HSHarry Stebbings
We know the future. I will tell you the future and you will listen and write it in your Wall Street Journal article.
- JCJason Citron
(laughs)
- HSHarry Stebbings
Okay? (laughs)
- JCJason Citron
Yeah. Um-
- HSHarry Stebbings
(laughs)
- JCJason Citron
Well, I, I, I think that, you know, if you think about the, the nature of AI and how the, like one of the key differences with it is... See, a- again, this is sort of where like, you know, i- i- if, if the, if this kind of technology could run like on a device, like on a console or on a phone, then the business model might be different than if it, than if it has to use so much compute that it like runs in a, in a server, for example. So like these, these details matter, but you could imagine, um, a game like that being more of a subscription service where you subscribe to the game kind of like, you know, World of Warcraft is. It's this never-ending story that you participate in and by paying a little bit every month, you get to continue to explore and be part of that world. Um, that to me feels like it could b- it could be, it could be a, a, an approach. You know, the microtransaction model probably has a place. M- you could potentially imagine microtransactions working there, but when everything is AI generated, y- you know, if all the microtransaction content is AI generated, you know, how will people react to that? If it's effectively free s- you know, will some e- e- enterprising creator figure out a different way to monetize it that makes all the content free so you don't have to worry about that? My guess is probably. Um, so yeah, it's, it's hard to say.
- HSHarry Stebbings
Jason, what did you believe that you now no longer believe?
- JCJason Citron
You know, a lot of the advice out there for how you run a company. (laughs) Um-
- HSHarry Stebbings
Do poli- do politics have a place in the workforce?
- JCJason Citron
I think that each CEO and each leader needs to decide for themselves how much they want to talk about politics in their workplace. The, the one thing that seems clear is that we are in a very kind of heated, divided time in the world. But y- y- yeah, I- it's up, I think it's up to each person to make that call.
- 39:35 – 40:59
Meeting with Danny Rimer
- JCJason Citron
- HSHarry Stebbings
I spoke to Danny Rimer before this show, and he said that his first encounter with you was probably his most memorable first founder encounter ever. Um, he, I think he described it as an interrogation, to be quite blunt.
- JCJason Citron
(laughs)
- HSHarry Stebbings
Uh, so, (laughs) so take me to the first Danny Rimer meeting. Where was it? What did you do? How did it go?
- JCJason Citron
It's funny he calls it an, an interrogation. I, uh, I remember I was meeting with him and I had just read an article maybe the day before about a company that he had invested in that I think kind of went bankrupt or something.
- HSHarry Stebbings
Yeah.
- JCJason Citron
And, um, I wasn't raising money but I was like, "Oh, I'll go meet with this guy. People say he's, he knows what he's doing and he's-" And so we met at a coffee shop somewhere in the Mission in San Francisco. I forget which one. And, you know, I'm, I'm a pretty curious person. I love to learn from people. You know, I think that so many, uh, you know, like there's two ways to learn in life. You learn from your own mistakes or from oth- other people's mistakes. And so I love to read books and, and, and talk to other people to learn about like what are their mistakes and what can I learn from? So I'm meeting with Danny and I'm like, "Well, you know, I don't know what do we talk about? I just read this thing, it was really interesting to hear about a company that just went bankrupt." And I was, so I was just really curious about it, so I just started asking him questions about the experience and what happened and what did he learn from it and what did he take away from it. And, and, you know, I have to be honest, I don't even remember what he said (laughs) at this... I mean, it was so long ago. (laughs) But I remember the conversation and it, and, and I know it really stood out, um,
- 40:59 – 42:58
What It Takes to Fundraise Successfully
- JCJason Citron
to him.
- HSHarry Stebbings
Do you think you're a good fundraiser? And with the benefits of the many rounds you've done, what have been your biggest lessons on how to fundraise successfully?
- JCJason Citron
I guess I am a good fundraiser. We've raised almost a billion dollars. Um, and I think that at some level, I think raising money when you're building a business that is growing really fast and has a lot of consumer love, it's kind of easy.
- HSHarry Stebbings
I don't disagree with you.
- JCJason Citron
Yeah. S-
- HSHarry Stebbings
Which was the hardest round?
- JCJason Citron
So we, we def- we definitely had hard rounds. Um, our series A was actually pretty hard because a l- a lot of investor... This was before we had Discord, so when we were working on our game title, this was I think maybe 2013. And at the time, what I was, what I was fundraising on was this vision to build a, a big gaming business around a group chat app starting with a game. And most people said no because they thought the game wasn't gonna g- g- wasn't gonna get there. Um, so we got a lot of nos in that round. And Mitch Lasky from Benchmark said yes, and he thought the vision was exciting and he thought we would figure it out. And, um, and, and so that was a hard round, but, um, but I'm very grateful to Mitch for, for, for, uh, seeing what I saw and supporting us in that. Um, but once we got to Discord and, you know, the charts were all up into the right, it was much easier.
- HSHarry Stebbings
Should you always take the highest price?
- JCJason Citron
No. In fact, I got an offer... I think our series A, I had one other offer for a little bit, for a little bit of a better valuation. But I really wanted to work with Mitch so I, I, I, I, I chose to work with him.
- HSHarry Stebbings
Is it a needle mover having Benchmark as an investor?
- JCJason Citron
Mitch has been very helpful. Um, I ta- I don't, you know, I, I haven't spent a ton of time with the other partners. So one thing that I have learned working with so many investors over the years is that it's not really always about the firm, it's about the person. So, you know, my, my sense is the other folks at Benchmark are, are, are great but I haven't worked with them, so I don't know. But working with Mitch has been great.
- 42:58 – 45:10
A Discussion with Rockstar Games
- HSHarry Stebbings
I had another story I had to discuss, was Rockstar Games, where apparently you walked in feeling pretty confident with bags of cash, um, expecting to buy a ton of IP. What happened there, Jason?
- JCJason Citron
Yeah. So we went to New York. This was around the time when we were building, um, our PC game store in late 2018. And I went to- to go visit with the Rockstar folks to talk to them about, um, whether they would list their upcoming title, uh, I think it was Red Dead Redemption, um, on our store. And, um, they were very gracious folks and we chatted with them and discussed a lot about like what their priorities were and, you know, tried to do the normal BD thing of like, "What's going on over here?" And- and what I realized as we were coming back was that the game s- store business at the time was such that they only wanted... Well, basically what I realized was that we were gonna have to spend a lot of money and minimum guarantees to get developers to put their games on our store. And it wa- it wasn't just Rockstar, but the- but that trip to New York was like one of the moments where I realized that the best games are gonna cost us a lot of money. In that moment in time, other people had just launched game stores as well. You know, the PC game store industry was kind of slow moving for a while. And in that window, like Epic launched theirs, we launched one, Microsoft was coming, and I realized that to compete in this business, we were gonna have to spend a lot of money on minimum guarantees on a lot of titles, and I didn't feel like it was gonna really be worth it. So, um, I decided we weren't gonna give- spend the money, you know, the bags of cash, um, on- on- on that title or on any titles, and we shut down the game store 45 days later and completely pivoted out of that business, which I had just raised a round of funding off of. So I remember calling the investor who had put the money in and I was like, "Hey-"
- HSHarry Stebbings
Which- which- which- which round was this?
- JCJason Citron
I don't know. We've r- we've done a lot of rounds. I forget the l-
- HSHarry Stebbings
(laughs)
- JCJason Citron
I forget the- I forget the letter. But, um, in any case, I remember calling them and telling them that we were gonna do this and- and I was like, "Do you- do you want the money back?" (laughs) And they were like, "No. Keep g- keep going. We think you'll figure something out." And they were
- 45:10 – 47:00
The Future of Discord
- JCJason Citron
right.
- HSHarry Stebbings
I have to ask you a question that is top of mind for me. I- I think there's a generation of incredible pr- private companies, l- like your Stripes, like your Starlinks, like your Discords, and the question that I have is what is the ultimate destiny for this? Like does it go public? Does it, uh, get bought? Does it run as an independent private company for years and years and years? I'm not saying to make predictions, any teasers, spoilers. Just what would you most like?
- JCJason Citron
Well, there's a couple ways to answer this. Um, you know, what I like is creating software for people that is useful and having fun doing it with like a team of great- of great folks. Like, that's what I enjoy. Like, I enjoy waking up every day, coming to work, and like talking about the features we're building and talking to my customers and- and trying to figure out how to solve problems for them and then telling our story. So that's what I would like to keep doing. And then the question is then, what's the context around that? And of course we've raised a lot of money and the business exists, you know, because we've had amazing investors and, um, a lot of wonderful employees who give us their time. So all of those folks, um, are expecting liquidity at some point, and I would- and I really want to give it to them. So there will have to be some liquidity situation eventually, because, um, people want to get paid, rightfully. But, you know, when and how and what, you know, that will be- we'll- we'll figure that out, um, as- as- as we move on. Um, but-
- HSHarry Stebbings
Would you like to be a public company CEO? Like does that hold any desire or interest for you?
- JCJason Citron
It's an intriguing sort of mode of operation, but, um, you know, I'll- I'll do it. But, eh, it's- I- I don't wake up and go like, "I cannot wait, you know, to be a public company and have an- and do- do an earnings call." Like, that's not, you know, the reason why I started the company. I started the company 'cause I'm passionate about our customers and their problems and- and I want to solve them.
- 47:00 – 54:31
Quick-Fire Round
- JCJason Citron
- HSHarry Stebbings
Listen, I would love to move into a quick fire round. So I will say a short statement, you give me your immediate thoughts. Does that sound okay?
- JCJason Citron
Yes.
- HSHarry Stebbings
So what book written before 1965 would you most recommend?
- JCJason Citron
Winnie the Pooh.
- HSHarry Stebbings
Why?
- JCJason Citron
'Cause it's just such a wonderful book. It's a story of friendship and fun.
- HSHarry Stebbings
Yeah, I can see why you're not an investor.
- JCJason Citron
(laughs)
- HSHarry Stebbings
Um- (laughs)
- JCJason Citron
Yeah. Were- were you, uh, were you looking for-
- HSHarry Stebbings
Honestly, Jason, this-
- JCJason Citron
... like Benjamin Graham or something? (laughs)
- HSHarry Stebbings
... this whole... Do you want- do you want my takeaway from this episode is, honestly, I think you are fricking great. You are such-
- JCJason Citron
(laughs)
- HSHarry Stebbings
... a lovely human being. But we also could not be more like other ends of the spectrum. (laughs)
- JCJason Citron
(laughs)
- HSHarry Stebbings
Uh, I- I had a great conversation the other day and it was like, hey, how faith impacts how you act in the world. And I responded, "I- I have faith. I believe in liquidity." (laughs)
- JCJason Citron
(laughs) Hey, capitalism is a- well, yes, okay. (laughs) I don't know what-
- HSHarry Stebbings
Don't say anything that pudges you. Don't say anything.
- JCJason Citron
Yeah. I'm like, I'm gonna... That's not a sound bite we're gonna- we're gonna have, but-
- HSHarry Stebbings
No, no, no, no, no.
- JCJason Citron
(laughs)
- HSHarry Stebbings
Uh, what's the most, uh... What blog post written post-2000, other than Founder Mode, is your favorite?
- JCJason Citron
Yeah. I really enjoyed a series of posts by, uh, Mark Schuster. He used to write in the late 2000s. He had a blog called Both Sides of the Table where he would share his experience, and I really, really learned a lot from him.
- HSHarry Stebbings
Dude, I- I grew up on that blog actually.
- JCJason Citron
Mm-hmm.
- HSHarry Stebbings
Yeah. He wrote one piece there about investing in lines not dots-
- JCJason Citron
Yes.
- HSHarry Stebbings
... and the importance of relationships over time. So important.
Episode duration: 54:31
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