Ep. #2, Feat. Keen IO’s Kyle Wild

Kyle Wild: Sometimes the person who is empowered to solve the problem can get the full dose of empathy for the problem. And when that happens, there's no meetings, it just gets better.

It's way easier to listen to a customer when you're the person listening to the customer.

I'm obsessed with cross-functionalism. Not all knowledge is quantifiable. Not all of the best tactics are quantifiable, right?

How do you build a company culture that harnesses that cross-functionalism?

If one person uses your product in the wrong way, maybe you educate them. If 80% of people use your product the wrong way, maybe you have the wrong product. Maybe there's a bigger market for that other thing.

Fred Stevens-Smith: Hi, I'm Fred Stevens-Smith, CEO of Rainforest QA, and you're listening to my podcast, Zero To Won. On this show, we'll explore the often overlooked tools and techniques that the best founders used to win. Zero To Won is brought to you by Heavybit, a nine-month program for developer-facing startups. For more information, visit heavybit.com.

In this episode I'm joined by Kyle Wild, CEO of Keen IO. We talk about how everyone at Keen does support and we discuss the benefits of building a self-managed culture.

Hello, dear listener. Welcome to Zero To Won, a podcast with me, your host, Fred Stevens-Smith, and Kyle. Any other identifiers you like to use, Kyle?

Kyle: Trying to own that name like Madonna.

Fred: Okay, Kyle. We'll stick with just the first name.

Kyle: I'm Kyle Wild. I'm co-founder and CEO of Keen IO.

Fred: Awesome. And what is Keen IO?

Kyle: It is an API platform that lets developers build analytics into all kinds of applications.

Fred: And what does that mean for the regular people? What does that mean?

Kyle: Regular people meaning non-developer?

Fred: Yes.

Kyle: I mean, to some degree it means please tell your developer friends about us.

Fred: Okay, great! Well, we can leave it at that.

Full Team Support

So Kyle, you know the premise of this podcast. The point is to take some of the stuff that we learn and we become really religious about over time and share that with the audience, who can maybe take some of those learnings and use them themselves.

So we decided today that one of the things that has been really crucial to Keen IO being so mega awesome is your full team support. So Kyle, why don't you tell us about full team support? Why you think that's such a secret weapon, why that's been so effective for you guys.

Kyle: Yeah, so I actually started my career in a support job, so this is to some degree probably informed by where I came from and what I experienced there. But I started out on the Google Analytics team as a developer support person.

So developer support or any kind of support role for a B2B company, it's really this, you know, the industry looks at it largely as, this is a cost center, how do we drive down our costs? This is part of our cost of goods sold. How do I make it more efficient, how do I get people to write fewer tickets?

How do I reduce the amount of hours it takes to satisfy a given number of customers? Or how do I, with a fixed-size support team, support a growing customer base? It's looked at largely as a cost center.

And while I was at that job, I actually learned a ton by talking to customers about what they were doing with the product, some of those things were not what we planned, and by talking to customers about what they wish they could do with the product.

So this was 2007. It was at least before I came across and maybe even before the concept of what's called customer development really hit the mainstream. Great book on this by Steven Blank called The Four Steps to the Epiphany. That's something every entrepreneur should read the first hundred pages of.

Fred: And customer development, what do you mean by that?

Kyle: Yeah, so customer development is essentially, it's really saying we have a lot of ideas about what kind of product we want to make, but the real ideas that are gonna sell to the market are actually out in the market.

Steve Blank says, like, outside of the four walls of your company. That's where all the insight is. So go find it. Talk to customers. Meanwhile, a support person's job description says talk to customers.

So these people are being paid to go out and help customers, help them through situations, to some degree collect feedback. But the reality is these are the people in the company over time who have the most insight about what the market needs today, where it's headed.

If one person uses your product in the wrong way, maybe you educate them. If eighty percent of people use your product the wrong way, maybe you have the wrong product. Maybe there's a bigger market for that other thing.

So anyway, back at that company, you know, we had these review sessions where the product team and support team, I mean, I wasn't even there, but like the heads of those groups would sit down and talk through, here's the summary of learnings that we've learned in support.

Fred: And so they did see it as at least somewhat strategic, this role.

Kyle: Yeah, and I think the things I'm saying in the abstract aren't probably that controversial, right? Like, yeah, your support people, it turns out, learn a lot of stuff about the marketplace, or at least about the current customer base.

But I think quarterly review sessions where you have this team of experts who are trying to summarize in a, you know, a 90-minute cross-team sync or whatever you call it, does a disservice to the customer.

Fred: So the starting premise is you experienced what we can maybe think of as kind of the specialized, siloed support model, right, when you were at Google.

Kyle: Right.

Fred: And so at the same time you were going through a bunch of, you know, personal learning about the value of the really direct interaction with those customers, especially as it relates to this thing that you're talking about, customer development.

So, you know, given those building blocks, what's the next step? You know, so we have those two kind of facts. Yes, customer development is super useful, and it seems like also predominantly support is seen as, like you said, a cost center, something that's to be kind of like optimized and made efficient and then just like shut the fuck up and go away.

So what's the next step? Like, how do we improve that? Like, what have you guys done to change this?

Kyle: So we don't have full-time support staff. So here's how we built support at the start of the company. And I think this is probably pretty common.

We made a Google group. It's like an email list, support at keen.io. You email it, it goes to the whole company because there's only three of us. Who cares? We made a public chat room that the three of us were in.

And I think a lot of companies do this at first because, you know, you got a couple people, you know, maybe you want to share that role. The thing that we did differently is as we scaled, so we're just about to cross fifty people. We still don't have a full-time support team.

And so we don't all get emailed every time every customer sends something out. That wouldn't work at our scale of customers or people. So what we do today instead is we have a rotation where everyone in the company opts in to a two or three day rotation on support, which is essentially like a shared burden kind of approach.

So this is a thing that scales really, really well as the customer base grows. It's also extremely good for onboarding, but I guess the key difference is we never changed that. We never said, we don't want to do that.

And the reason is largely, I wrote this manifesto called Why Everyone at Keen Does Support, and it's on our internal training, which basically says if you take the support role, which is talking to customers about their problems, and you put it in one group, that group is going to develop a lot of customer empathy. But what that means is that that customer empathy isn't necessarily going to be diffused throughout the company.

What happens is they're supposed to package up the customer empathy into a list of actions and then give it to somebody else. In our model, if you have a problem with one of our SDKs, there's a reasonable chance that the person you're talking to can go fix it.

In the early days we would have platform issues, and, you know, Dan, our CTO, who is running the platform, there was like a one in eight chance he would be the person who gets your support ticket. That was awesome through our first couple years, because imagine being the customer who's like, yeah, I emailed support at keen.io and the CTO responded and said, I'm gonna fix it, and that night he went home and fixed it.

Because in his mind he was like, well, I could write this down on a list of actions and try to work it into the next sprint, all this stuff that big companies do.

There's nothing wrong with it. Process is a good thing, but sometimes the person who is empowered to solve the problem can get the full dose of empathy for the problem. And when that happens, there's no meetings, it just gets better.

Customer Empathy

Fred: So you're using the word empathy, and I think for many of us, that's a strange word to hear in relation to support and startups and all of that stuff. So I really like this phrase, customer empathy. Can you define what you mean by that, when you talk about someone at Keen as having a high level of customer empathy or needing to work on that? What does that mean?

Kyle: So I use the phrase to mean a bunch of things. I mean, it's most clear, really, customer empathy is about when your customer has feelings about something in your product, you can identify, you can relate, and you can even share those feelings.

You know, if you get on the phone with a customer who's struggling with your product and they're frustrated, you'll start to get frustrated, probably on their behalf. Sometimes maybe the immediate inclination is to get defensive, but it's way easier to listen to a customer when you're the person listening to the customer.

If I talk to a customer and they've got a problem and then I go to you and say, hey Fred, this customer's got this problem, you'll be like, yeah, well, they don't know what they're doing. It's like, no, but you don't understand, you had to be there, man. Like, it was real, like there was pain. The emotion can't really be translated indirectly.

Fred: I see. And so this empathetic response, which is basically two humans interacting and feeling, yeah, empathy for each other, this empathetic response, it's very hard, that gets lost in translation if we talk about like macro level reporting or about two VPs meeting together once per quarter.

And so this idea of kind of total team support, you get the team to each individually experience these interactions and so drive up the level of empathy and therefore presumably drive up the quality and fidelity of the insight they get from customers.

Kyle: Right.

Why Most Companies Don't

Fred: So what's interesting is, why don't other people do this? You know, there's clearly, you know, the so-called devil's advocate, there's clearly a lot of arguments that one could be making against this. It's inefficient, we're wasting these valuable engineers' time. Like, oh, you have your CTO sitting on support when he's not like managing the worker bees.

You know, like, I guess maybe it might be worth maybe separately examining the broader organizational context that that can exist within. Why do you think that doesn't exist in more companies? Why do most people, like you said, once they've moved beyond the initial founding team, immediately try and transition off this notion of full team support?

Kyle: The number one reason that most people don't do it is that most people don't do it.

You know, most of the tactics that people employ when they're designing their business, they're employing tactics that other people views that, well, if the majority of companies do, you know, X function or satisfy Y problem in a certain way, let's just do it that way. It's expedient to do it that way.

So it sounds a little meta, but the number one reason people do it the way they do it in the majority is because people do it the way they do it. There are other factors too, I think. I mean, there's a whole, I could give a whole rant on kind of functional specialization, and, you know, while that gives you some efficiency, there's some pitfalls from that.

And this goes across function, but support specifically, I think people put it in a category. So there's a question, I guess, about whether does getting rid of full-team support lead to a lack of customer empathy, or does a lack of customer empathy lead to getting rid of full team support?

Are we saying this terrible business of having to actually talk to people who might have complaints, I don't want to deal with that. I'm gonna shield myself from that. There's a braver perspective, which is people have complaints. I want them to talk to me so that I can do something about it.

I also, on the other hand, have a lot of energy to do things and I don't know quite what to do, and this is a major input, even for me, about what I do with my time and how do we allocate company wide resources.

Fred: And I think you hit on something pretty important there, which is the use of the word fear and bravery, right? That's the terms you refer to this in.

I do actually think that's something that I've seen many times, is that once a founder has a very strong initial thesis about the product that customers will find useful, what that thing is that is what people want, right? I think that there's a real tendency to try and, rather than seek to invalidate that yourself, to almost bury your head in the sand and say, no, I can build a business around this and like I can force this to be correct.

Have you seen that yourself? Is that something that you have to struggle with?

Kyle: I've seen it all over the place, myself. I mean, I'm certainly guilty of it, maybe the most guilty of it, across various areas where, you know, my intuitive thesis based on incomplete information, one of the kind of tenets of scientific method is that all the information is always incomplete. All we can do is try to make it more complete.

But based on incomplete information, you know, come up with a strong opinion. And when new information comes that could invalidate that opinion, we have two choices. We can either soften our position, maybe even reversing it, or we can build barriers between the information and us and say, I don't want that information coming in. I've got really important opinions over here I want to keep.

And I think to some degree, you know, a lot of companies are organized in a way, their life cycle of companies is something I like to think about. And a lot of them kind of have this model which says the first phase is find product market fit, the second phase is scale. I think this is especially common in the valley.

I think there are all kinds of reasons behind it. One of the major reasons is that that's actually how probably 75% of the investor community thinks about businesses too. You're either pre-product market fit or you're post-product market fit. And if you're post-product market fit, step on the gas and don't make things.

And we kind of pay lip service to building an innovative culture in your big company. That doesn't happen. It's super rare for that to happen. And as a result, what we do is we early on optimize for learning and later on optimize for efficiency.

You know, full team support is one of these things that is more about learning than efficiency. There's an argument that learning is the most efficient thing you could possibly do if you think on a long enough timescale, but I don't think that's super common to think on a long time scale.

Fred: So for you this is actually driven a lot and totally interrelated to the very much short-term thinking around the life cycle of a company.

Kyle: I think so. I think, and it doesn't mean that we shouldn't be working on efficiency, it's just that I think it's possible to do these things in parallel, for some parts of a company that are more well understood to be optimized, and for parts of a company that aren't, including new markets, they're never well understood.

No company can tell you today what they're gonna be selling in 50 years.

What you can do is build a culture that can last fifty years to even answer that question.

The only way to assure that you're gonna answer that question is to continue to learn and to build a company that, while it's a kind of, there's mental gymnastics here. You have to bet on the things you know while making a side bet that you don't know everything. And I think that requires a degree of intellectual humility that's probably rare.

Making It Work

Fred: And let's say we think that this is a great idea, right? And we want to implement it at our company. What are some of the ways that you actually have to operationalize this?

Like, it sounds great, right? Full team support, but, you know, beyond the very obvious things of, okay, define a quota, maybe have it opt in, you know, have some process defined, have certain tools that you use. Beyond that, like, what are the challenges with operationalizing this?

You know, how do I actually make this data useful rather than it just be like, oh, these are my support days, I'll just do it and go home. How does that knowledge get shared? How do you think about the so-called customer empathy that is gained through the support, like how it's actually made useful to the company?

Kyle: I mean, so to some degree it's chaotic and random. If you happen to be a person that can utilize this certain knowledge in your day-to-day job and you happen to be on support when this ticket comes through and you're talking to this customer, that just happens on its own. That's invisible efficiency. It's impossible to put into a spreadsheet, and yet probably increases the amount of output we can get with fewer meetings.

So that's the chaotic piece. The more ordered piece is, so, okay, well, let's say that I'm the person who can use the information, but you're the person who gets the support ticket. And you can come to me at some point and say something about it. But maybe it's like, well, I don't know that person, I don't know that team, or I'll just wait for our monthly sync up, but it'll fall maybe below, you know, the top five priority items or whatever it is.

What we do is we encourage people on support, you know, sort of through, this is through our onboarding and our training, we encourage them to jump into the appropriate Slack channel. So we use Slack at Keen.

And I idle in a ton of Slack channels and kind of pay attention to what's going on. So I see this stuff happening all the time where, you know, somebody learns something, it's a customer suggestion. They copy and paste the customer suggestion into the product channel and say, this is the fourth request I've seen on this.

Maybe I dug through Intercom and I found some, Intercom's our support tool. Maybe I dug through Intercom and I found some similar requests, paste it into the product channel, you see a discussion start. So this becomes an input for the product team and other people who are just kind of interested in that function.

I guess even that's a little chaotic because it's kind of like, well, this is out there now. But by pasting it in there, instead of one person hearing about it, yes, there's a chance that they're the right person to handle that. But even still, now eight people have heard about it. There's a better chance that those eight people are the right ones.

The same's true with sales. You know, in the sales channel, whoever happens to be on support will hop in regularly and say, here's a customer who asked me about enterprise pricing. You know, that's a huge indicator that the salespeople should get involved. If you paste that in your sales channel and say, this customer just asked me about enterprise pricing, obviously, that's the kind of thing that salespeople are gonna listen to.

This isn't that different than how you do support fully specialized way, you know, the way to operationalize this. It's just there's that some percent chance that they're more empowered directly to do something about it.

Bets You Can't Quantify

Fred: Yeah, and I also think that, you know, we do at Rainforest, we do a flavor of this, and I've definitely seen the chaotic side bear fruit many times. But I also do think it's something that becomes increasingly hard to justify even to yourself as you get bigger, because it's something like, okay, yeah, I actually do believe there's real value here, but since I can't quantify this, how do I defend it to people?

How do you think about that? Do you think that's about having the right kind of investors, the right kind of board, the right kind of support, that they allow you to make some bets that aren't necessarily easily quantifiable?

Kyle: Yes. I think not all knowledge is quantifiable. Not all of the best tactics are quantifiable, right?

So I love competitive sports. I don't know, I learn a lot about team performance, individuality, the application of playbooks or the writing of your own playbook, and what I like about professional sports is that there's always an outcome. You can always say, well, did they win a championship or not?

You know, a lot of times people, so I follow the NBA, which is basketball, and thanks for that kind of question. Yeah, I don't know if they have this over in Europe, but basketball.

Fred: They don't.

Kyle: It's like soccer, but use your hands.

And this team came along that I really enjoyed watching a few years back, who had a very fast offense, you know, when you have the ball. And there's all this feedback, all this criticism. And maybe they have that. They have the offense. You know, there's all this criticism that came out because it's like, oh, you can't win a championship with a fast offense.

And when you ask people why they'd say that, they'd be like, well, because no one has. I'm like, well, okay. Presuming that this were the first year of the NBA, no one's won a championship with any tactic. Therefore, is every tactic invalid? Like, you know, this isn't the kind of reasoning that maybe always applies.

But I like that there's some data, and, you know, more recently, over the last five or six years, a team called the San Antonio Spurs, which is my team, has won multiple championships with a fast offense. But they also added a very, very stingy defense. It turns out that that team who had the fast offense, they were the Phoenix Suns. They had the number one record two years in a row. They had the MVP of the league, the, you know, greatest offensive point guard ever, kind of a liability on defense, Steve Nash.

It turns out the reason they didn't win a championship was because of other parts of their playbook. It wasn't because they shared the ball, moved it, spread the scoring around, you know, rested their starters, all these other things that lead to a fast offense.

I think not all tactics are quantifiable. So the thing is, if your business is forced to make every decision quantifiable, to do everything in a purely short-term scientific way, it's gonna be very hard to succeed in the long term. And I can't prove that. But in thirty years maybe I will be able to prove that.

But you said something like, how am I going to defend this decision to other people?

Not every decision needs to be defended. We're talking about startups. Startups are risk endeavors.

The number one thing that you can do, you know, if you were investing in startups, is judging whether or not the person or people in charge of this company are people that are gonna take the right risks.

We can't run startups the way that you would run an insurance company. It's really, really hard. They're built in a way that has tons and tons of data and they make risk-adjusted decisions all the time, and they can think longer term.

The truth of the matter is the same kind of person like you or me who starts a company is not super likely to listen to what people say about risk. Like I said earlier in the podcast, I usually tell people don't start a company. That's what you hear. I mean, I heard this a million times in thinking about starting a company and in the first year of the company.

And there's something in our DNA that allows us to, or makes us crazy enough, I don't know what it is, or in our upbringing, something that makes us willing to take unquantifiable risks. I think it's important that companies preserve that over time.

Because every new champion in any, I like competitive chess too. Every new chess champion is doing something different. They're always doing something that there's no evidence until they win that that's a great tactic.

And it's crazy. As soon as they win, then everybody else is like, oh wow, this is such a great tactic. Let's use that. And meanwhile there's someone else out there saying, I'm going to disrupt all these people who are using yesterday's playbook.

If the company isn't built in a way that allows you to continue to make those bets, it's gonna limit your size.

Fred: Yep. And so I think the obvious theme that comes out while I'm listening to you is that you're a contrarian.

Kyle: And I've heard that, but I don't believe it.

Fred: Right. So let's talk about it. Because I think that of all of the great founders and CEOs that I have personally been able to interact with and spend time with and get to know to whatever extent, it seems like all of them are very comfortable drawing the line in the sand with things that they just don't agree with the general belief on.

And doesn't seem like there's any real system for defining what the things are that they say, nope, this is something that I have my own belief on and everyone else is wrong, versus those that they just kind of say, well, whatever, doesn't matter. In other words, it doesn't seem like there's any real system to the fights that they pick, but they do tend to pick more fights than most people.

Do you think that's kind of an inherent part of your personality? Have you seen that as a general pattern, being a contrarian? Whether you see yourself as one or not.

Kyle: So I meant to make a joke when I said I hear this a lot, but I don't believe it. You know, there's an irony, right? I'm being contrarian about that. But that's actually the truth.

You know, and I think that you probably hear the same thing from anyone labeled contrarian. I mean, I have my reasons for my opinions. I'm happy to share my reasons.

Fred: Happy to hear up to the other. You're a contrarian that thinks you're right.

Kyle: Yeah. Just like all of us.

Fred: Yeah, I mean, the real question is, so do you come to your opinion because it's the opposite of the status quo, or do you come to your opinion regardless of the status quo?

Kyle: Regardless of the status quo. I tend to come to my opinions regardless of the status quo. Oftentimes very aligned, you know? Joined an accelerator, started a venture-backed company based in San Francisco, you know, with a subscription revenue model.

These are not contrarian things, these are completely mainstream things, as Delaware C Corp, you know, all that stuff. Our outside representation is Cooley, didn't want to take a risk on that.

I think it's mostly that the opinions that you do happen to hold that aren't completely on the straight and narrow are the ones that are worth a story, or people dig into, they make people curious at the very least.

Fred: So those are the things. In other words, even if you do ninety percent of stuff exactly the same as everyone else, it's the ten percent that actually defines you as a company.

Kyle: Yeah, I guess so.

Cross-Functionalism

Fred: What are some of those things for you and for Keen IO? Like, what are some of those contrarian beliefs?

Kyle: Contrarian beliefs. So we do this thing where everybody rotates through support, which I think is great.

Fred: Good callback.

Kyle: Yes. So we've always been a very, very kind of almost obsessed. Probably I've been, I am obsessed. I won't accuse the whole company of being obsessed, but I'm obsessed with cross-functionalism.

So this is like, what happens when a person happens to be really good at engineering and really good at marketing? Well, in most companies you put them into engineering or marketing and you kinda lose the upside of that other thing. And then maybe they transfer in a while.

How do you build a company culture that harnesses that cross-functionalism? Well, number one, you make a startup, because when you have six people and fifty things that have to get done, you benefit from the cross-functionalism of those six people, right? I think this runs to the core of why startups constantly beat better funded big company projects in their space.

How do you maintain that as you scale? I don't know. But we have a lot of experiments to figure that out. You know, so for us the cross-functionalism, I guess it is really part of our, a core part of our DNA, because it's like

Fred: And that is contrarian in and of itself, right? This idea that rather than specialize in the thing that you're relatively best at, that you should bring your whole self to work, which starts to sound suspiciously like this thing that I've been hearing a lot about, the teal organization.

Kyle: Yeah, I mean, it doesn't mean not to lean into things you're really good at. It just means you might be really good at two things. It's possible for a person to be world-class at two things. And if it is possible and you happen to find those people as a business, it would probably be valuable to harness some of that.

I mean, bringing your whole self to work is a big part of our company culture and how we think about employment and how we think about recruiting. It's one of the things that attracts people to our company.

That doesn't necessarily mean I'm going to build a hybrid job description that changes as my whims change, although it has meant that in the past, at times. It's certainly harder at 50 than it was at 10 to accommodate that.

It just means instead of running a filter on, here are the things I'm good at, here are the things that a company out there may want to pay me for, and I'm gonna pick one of the things in the overlap.

With cross-functionalism is really about, well, it's possible. A, it's possible for an individual to have two, and B, a given team of people with different functional abilities is stronger than a team that all has the same. So instead of saying, all of you people, you five, you all do pure sales, that's it. And you'll have weekly meeting with the group over here that does this other thing, community or something.

It's about saying some people are really good at both, and a unit that has a salesperson and a community person that's maybe focused on a vertical could be a better way to organize the units, as opposed to an organization that says, all of you with rifles go over there, all of you with shields go over there, and then we're gonna go to battle.

So this is largely like phalanx-based organization versus guerrilla organization. This is how Navy SEALs organize. And I think bringing together a bunch of different strengths is the best way to build a squad that can achieve some kind of joint goal.

Fred: So do you think this notion of cross-functionalism to the extreme, do you think this is one of the secret weapons of Keen? Is that something that you will take with you wherever you go? Oh yeah. You fundamentally believe this is a better way to do a company?

Kyle: I do. I think that, I mean, there are a lot of open questions about how do you do it at various scales of company. That's what we're solving. The difference is we don't shrink from that challenge. We don't say, well, this cross-functional approach was really good through 30 people.

I hear this all the time. People always say, oh, that'll be great through 30, and then you need to just fully functionally specialize like every other company. Our perspective is there probably is some way that is undiscovered to organize at a new scale and capitalize on some of the benefits that smaller-scale groups of people have.

We will experiment to find out. We won't experiment so long that we jeopardize the company, but we'll experiment. And we do some things like, you have to kind of make, sometimes you have to make decisions that are not completely in line with all of those ideals, knowing that this is a temporary decision, but at least we're explicit about it.

We're like, this is a temporary decision to organize in this way over here in this area of the company. Let's reevaluate that. And I think this is the thing about, you know, being like a sort of a high growth valley company, is that you kind of have to weigh the risk of what happens if you go out of business and merge into another company or get acquired or shut your doors? Well, all of your experiments die then.

So, you know, you can't be so idealistic that you don't perform, but, you know, given a base level of performance, at least at our company, there's a lot of room for iteration on the status quo.

A Generational Shift

Fred: To what extent do you think that, I mean, I agree with you, for what it's worth. To what extent do you think that this is related to the changing demographics of the workforce, and especially for companies like ours and probably most people that are listening, they probably work at companies that build software and skew relatively young, skew relatively nerdy.

You know, do you think this is affected by the demographics? Is this related to this so-called millennial generation?

Kyle: I can't speak to the whole generation. I've heard some things, I've read stuff. You know, I don't know.

Fred: Well, put it another way. If you were running an organization that was a government organization and was staffed 90% by people who'd held tenure in their roles for at least thirty years, and everybody in the organization had a job for life, would this work?

Kyle: I think it would, but I want to caveat that by saying I'm not proposing that specialization is a bad thing. There are people who are very, very good diving deep into a craft and owning that craft for decades. That's a super valuable thing. I would never propose that companies should fail to harness that depth.

I'm just saying that there are also other neurotypes. There are also other kinds of individuals, and those people have always struggled in those organizations.

So how that manifests, so this maybe does speak to the millennial generation, how that manifests is they shift careers. You know, I was in developer support. I grew up as a programmer. I sold ads, you know, I was first engineering hire.

I was a game designer. I ran paid advertisement and marketing analytics. And that's all before this company. And here I've done an even wider variety of things.

So for the companies who employed me, the way it tended to manifest was, when the company matured to a point where I was gonna be forced to specialize, I kinda saw it coming and went and left for an earlier stage company.

My challenge at Keen was, how do I build a company where, if we hired a young Kyle, a young me, that person maybe could be harnessed for a longer period of time? I think there would be value in that, even though that sounds egotistical.

Fred: No, I don't think it sounds super egotistical. I think it makes sense. I guess the interesting maybe paradox there is that to some extent my generation and basically your generation, we're of the same generation probably, you know, we've grown up with our parents having had the previous societal ideal of employment for life and total stability and a real distinction between work and career and passion and fulfilment, have all of that just totally shattered by the various economic collapses that have gone on, and have been forced to go through multiple careers.

And I think the people that I know from our generation, most of them have tended to treat that as a given, that this is what I'm doing today. And five years from now, who knows what I'll be doing. And they take that lack of certainty as not being like a really scary thing or a high risk thing, but more like a freeing thing, something that feels very exciting.

And I think I understand what you're saying, but is there not some sort of paradox there between this notion that we'll be able to work on many different things over the course of our life, and then the maybe competing notion that that could happen at one company? Is that even a good thing?

I mean, is it like, and I'm trying to not load the question, although it is loaded, clearly. But what do you think about that? You know, do you think that the ideal would be that actually Keen can be this hundred thousand year long company where people do come and have kind of a job for life?

Kyle: I think that there's a benefit to the company. I think it's pretty clear there's a benefit to the company in keeping your people for a long time. There's a benefit to the people to have agency over their careers, what they do, and to be working in areas where they're the most passionate. There's also a benefit to the company for people to be working in areas where they're most passionate.

We all have a friend who's checked out of their job versus a friend who's really, really bought into their job. Guess which one has better ideas, has more ideas, knows how to dig deep, or doesn't even have to think about digging deep whenever, you know, the company hits struggles or their department in the company needs to prove their worth, whatever it is.

It's the people who are really driven to do the kind of thing they're doing, as opposed to, you know, I'm just sort of cashing a check, who have that extra gear they can shift into. So there's a benefit of the company too to sort of map individual motivations to company goals.

It doesn't mean if someone were to join Keen today and say, my passion is that I want to juggle bowling pins on 9th Street in San Francisco, that's their only passion. It's not super likely we could use that, although I would entertain the thought. Right? I'd talk to the community team, maybe.

Fred: I know you would.

Kyle: Yeah, I'd be like, hey, this person wants to juggle bowling pins with a sign, they have a hundred thousand people following them on YouTube. Is this the modern day version of the sandwich board marketing campaign that car washes use? I don't know. Or at least entertain the concept.

And as far fetched as that sounds, and when I said it, I didn't know I was gonna conclude. I was making that shit up, trying to think about the most unrelated thing in the world to software. It's just that we'll entertain the notion. It doesn't mean we're gonna go hire that person.

It doesn't mean you can't take your whole budget and say it's all experimental budget. I mean, that's not a prudent thing to do. But on the other hand, what I'm proposing is that taking all of your budget and saying none of it's experimental budget, that's also probably not a prudent thing to do.

Meanwhile, if somebody's passion is, I really like deep technical concepts, but I'm an extrovert, what am I gonna do? Six years ago, five years ago, that was hard to find.

It's like, what do you do? I don't know. Well, you need to decide. You need to decide which one's you.

It's like, no, I really like, like, this is speaking from personal experience.

I love people. I like to meet new people. And I like really deep technical concepts. I like to just sit around reading absurdly detailed systems theory stuff, right?

And, you know, what I did in my career was sometimes I had a really extroverted role, sometimes I was, you know, writing code 60 hours a week. Now there's, companies have created this thing called developer evangelist, where you can go do that. Before that role was created, those people existed. It's just that they were forced to choose.

Fred: And, you know, listening to you, it seems obvious that you will be able to get more, you know, even if we abstract it into narrow economic terms, you'll be able to get more utility out of an employee when they're able to deliver value across the multiple things that they're passionate about. So that's kind of, seems obvious, actually, in a way.

So why is it that the most successful, monetarily, economically, you know, as judged by the market, why is it that those companies don't do that?

Kyle: I don't think it's true that none of them do. I think some do it better than others.

Speaking to like large multinationals, public companies, I think that Accenture, General Electric, two really interesting case studies in treating people as individuals. Those are not small companies. And they're not unenduring companies either.

It's probably worth mentioning GE, which maybe people don't know a ton about. GE was started on the notion that a given individual's talent level could be nonlinearly high. You know, what if you found a Tesla? GE found Tesla. GE found a lot of people like that.

GE was also in the Dow when it started and it's still in the Dow. It's been like a hundred something years. Never left the Dow. The other 29 companies that I haven't even heard of.

That's a major multinational corporation that's built largely on the notion that investing in the individual, paying attention to who they are and how they're progressing could become a valuable thing.

You also don't meet a lot of ex-GE people. Right? You know? But I meet a lot of ex-Google people.

And I don't mean to throw them under the bus, but I don't meet, I mean, even though there are way more ex-GE people in the world. Even today they're way bigger than Google on a headcount basis, not on a market cap basis. You don't meet a lot of ex-GE people.

And I'm not saying that you should lock people into your company and they should only be employed there. It's just that it shouldn't be irrational for them to stay. And it's irrational to stay at a lot of companies.

Bringing Your Whole Self to Work

Fred: Do you think it's mostly fear that stops people kind of opening their eyes to the obviousness of this all, this notion? I think the big thing that, when I started reading around organizational theory and what are some of the ways that people, companies like you guys are trying to change things, the thing that really just slapped me across the face was the phrase that we used earlier, the sense of bringing your whole self to work.

And I think there's a phrase, there's a chapter or passage in Reinventing Organizations that really succinctly describes how, for the vast majority of us, we have a work persona. And that work persona includes the things that we think are positively judged in our organization and excludes all those things which we think may be potentially detrimental.

And this notion that today this is becoming increasingly an old fashioned concept, given that our lives are basically lived in the open. You know, that was the thing that really, like, kind of slapped me across the face with, like, wow, this is obviously the way forward.

Do you think that there's going to be a wave of companies that adopt this model? You know, we're looking at the obvious high profile one that everyone loves to talk shit on, is Zappos, right? Then you have kind of Holacracy that's been implemented to varying degrees by companies, including Medium is probably a pretty famous one.

What do you think the state of this is? Do you think that this is becoming more and more about, you know, relatively young founders kind of taking a brave risk? Do you think that's what's driving this forward? Where do you think it is? Where do you think it's gonna be five years from now?

Kyle: So what is the state of it, where it is defined as bringing your whole self to work? I think that there is a hunger to do so in the employment base in the world, in the talent base.

I think that that's probably always been there, but I think prior generations might have thought, well, that's a little bit entitled. And anyway, this company's gonna pay my bills. Single parent income is gonna pay for four people and a house and a car and a yard and, you know, the American dream, and I'm gonna get to work there for thirty years.

Well, if that's what was on offer from companies, yeah, maybe people in the talent base shouldn't be so entitled, right? Like, companies are offering a lot. That's not the reality we live in today.

Even the most successful companies, even out here, which is in the valley, in the Bay Area, which was least touched by the recession probably in this country and maybe globally, even out here, people went through massive layoffs. I was unemployed for six months.

I was trying to find something like, this notion that, well, I shouldn't take control of my career and drive toward what I want and the kind of personal and professional and intellectual development that I want because the company's gonna provide me with a lifetime of security. Well, it's not. The companies aren't gonna provide you with a lifetime of security.

It's unlikely. Given that, developing yourself is probably the best security-oriented investment you can make. Given that, you should probably take a job at a company that's going to invest in you and wants you to invest in yourself and your own development and your marketability.

So there is a generational aspect to that, I think. And another thing that you mentioned is there are some famous companies out there that are now implementing alternative models around this stuff. Well, there always have been. I was a crazy kid.

I don't know. I grew up in a intellectual desert in a way, so I had to read a lot of books. I still read a lot of books. I really like to read the books of founders, leaders, entrepreneurs, people who've made things or changed things in their biographies, right?

I can tell you from my own research that there have always been examples of this. You know, I love to go to GE. GE's not a new company. They're a totally strange company, though, when you really explore.

It's really, to me, it's more about the fact that more companies are talking about how they do things. And there probably have always been companies organized the way Medium's organized. Or not always, there probably for a long time have been. It's just that they weren't high profile. They weren't successful enough to merit conversation, right?

Like, I would assume a lot of alternative organization models led to companies that died before we heard about them. That's the thing about risk. Like, risk, you know, it's like in genetics. If you increase the genetic mutation rate, you decrease the survival rate.

So if you change everything in your company to something that's never been tested before, if it works, you created a new species. Awesome. Not super likely. It's probably more common that you're just gonna die, you know, in infancy. And I think the same thing applies to companies.

So maybe what we're seeing is a mirror of the market conditions, maybe a reflection of the fact that alternative, self-empowered, holistic, authentic employment environments are actually starting to win, where maybe in the past they didn't always win.

And yet, if you were a great engineer in any generation in the last four generations, five generations, maybe not in software, but in a lot of the other areas of engineering, you probably were looking at GE, you know. I really wanted a job at GE. I got to the final round, didn't get a job out of college. Like, I was looking at it.

And there've always been some examples. I think they're gonna be more and more. I think as the talent gets more agency, as work becomes more differentiated and less commoditizable, as they get to choose where they work, well, it's probably gonna benefit companies who want to be chosen.

Startups Should Feel Like Art

Fred: And this is totally interlinked as well with the rise of software as well, isn't it, really? I mean, like, because it's very much harder to say in a manufacturing context you shouldn't be specialized, I think.

Kyle: Yeah, I mean, I think there's an amazing blog post by Henry Ward, the CEO at eShares, recently.

I just retweeted it today. It's their entire, like, eShares 101 full-day class they teach people when they join. I love it. 80% of it I would copy. 20% of it I'd love to have an argument about.

But one of the things, slide twenty, one of the things that he talks about is, you know, in areas where you know a lot, you should optimize. In areas where you don't know a lot, you should specifically do things that are unoptimized, that don't scale. You should experiment. So the thing about manufacturing is manufacturing's at the end of that journey.

You've designed, you've found market research, you've prototyped, you've tested, and especially most manufacturing, it turns out, is beyond the first run.

You know, you were asking me earlier, before we started recording, about the Apple Watch. That's the first run. The real deep manufacturing expertise that Apple's gonna gain from the Apple Watch, it will manifest in the second run. I always buy the second version of an Apple product.

So even the majority of manufacturing that already exists, even within the context of manufacturing, it's a known quantity. Yeah, we should work toward optimizing that. Manufacturing literally is about making identical copies of things. That's a very convergent marketplace. And if you want to converge, you should optimize.

Software's convergent too. It just depends on what stage in the life cycle and where you work in the system. If you join Google right now as a search quality or search efficiency or speed or scalability engineer, yeah, that should be a highly optimized role, right?

Like, you shouldn't be a crazy person, total right brainer, never study computer science, probably, to go into that role, because all they need to do is hit some percent year over year. And they focus really well around that. They'll be fine and they'll lead. I mean, they consistently output the best distributed systems engineers, in my opinion, some of the best in the world.

Yet if you were gonna say, I'm gonna make a new search business, you're not going to optimize your way toward that. So even within software, I think it varies. Some software feels more like an ops and almost manufacturing-esque kind of process. And some software feels like art.

And I think we're talking about startups. Startups generally should feel like art. And that's not true about all of them, but in general, like, you're making a new kind of thing or a new version or new perspective on a thing that already existed. You're not saying, I'm gonna make the same thing at a cheaper price.

Fred: And there we have it. What a great quote to end the show on. Startup should feel like art. I couldn't agree with you more.

Thank you very much, Kyle. That is the whole point.

Where can people find you on the internet? Where should they look you up, etc.?

Kyle: I don't recommend looking me up. If you need to, you can follow me on Twitter @dorkitude.

Fred: Perfect. Thank you very much, Kyle.

Kyle: Thank you.

Fred: Thanks for listening to Zero To Won. Find me on Twitter @fredsters_s. To learn more about Heavybit, visit heavybit.com, and while you're there, I would go into their library and check out some of the recordings of their speaker series program, where amazing founders get into real detail about how they went from zero to one.