#91 – From zero to one (Ben Grynol & Scott Klein)

Whether due to team dynamics, a lack of capital, or imperfect timing, most startups fail. But what differentiates the winners from the losers? The businesses that succeed are the ones that know how to navigate those initial hurdles. In this episode Levels Head of Growth Ben Grynol and Head of Product Scott Klein chatted about the idea of zero to one—going from nothing to something at a startup. They dived into why this can be challenging to build and what it takes to succeed.

09:52 – The mindset of an entrepreneur

The beginning stages of a startup are fueled by the need to solve a problem you can’t ignore.

At the zero stage, yeah, it’s really this emotional, just nugget of wisdom of, “I can’t be the only one that thinks this way. I cannot be the only one that feels this way. I don’t think it’s a special thing that I’m feeling this way or a unique thing, I should say, but it is very special and I’m sure a bunch of other people are feeling this way. Why has no one gone to solve this?” So that’s really the zero story of, we didn’t do it to set out to build a big company, we didn’t do it to set out to build an empire or a venture-backed unicorn. We really set out to solve that emotional struggle that we were experiencing in a way that we felt the world needed.

12:14 – Understand the problem to find the solution

The number one competitor every startup has is inaction. If you want to find a solution, you need to start by understanding the problem.

We had a lot of people in our network that we could put open source solutions in front of them, or we could put the one commercial solution in front of them and say, “Well, you don’t have a status page, you’re telling me that you want it. You have the option to go buy this thing right now. What gives? What’s the delta? What’s the diff? Why are you not doing it?” And so we started to get just a sense for what’s even important into them? Before we even laid a line of code down, why is this even a thing that you’re not acting on? There’s some gap in between the future where you want it to be and where it is right now that’s causing inaction. So it’s possible that these solutions existed, but they didn’t quite get beyond the gap of, hey, this is going to make my life better. It might make it different, but that doesn’t necessarily mean better. And so people were just sitting on an action. This is the number one competitor that every startup has is just inaction or stasis with how things were. And so I think through those conversations, we were able to triangulate around, I think someone just needs to do this and do it seriously enough that people believe them.

15:13 – Talk to your users

Ben said talking to your users and getting their feedback is the best way to find out what your product needs to succeed.

It sounds cliche, it’s YC’s mantra, it’s what you hear in every startup circle that a person would be in is, “Go talk to users. Talk to users. Talk to users, get feedback, talk to users. And once you’ve talked to users, go talk to more users.” The thing that you hear often where people make mistakes is, so you and your brother had the ability, you had the talent to be able to go lay down code. And it’s so easy to dig into the idea of, “Okay, let’s just start building.” And you start building against something without having any idea of what you’re building. Hypothetically, it takes four weeks, that’s usually not the case. More like four months, six months. People go into a cave and then they surface and they’re like, “Ta-da,” and they’re just waiting for this grand reveal, and everyone’s like, “This thing doesn’t even work. It’s a wheelbarrow without a wheel. What are you doing? That’s not going to carry anything.” And that is a big mistake that people make.

20:23 – Focusing on the smaller customers

Scott said he preferred focusing on small customers instead of big ones. It allowed the company to have more freedom in designing their product.

One of the things that I’m happy that we did was we made a decision to focus on the smaller customers first, because we knew they weren’t going to have such enterprise feature requests. And what we found along the way was that a lot of these enterprise feature requests were actually just nice-to-haves and not needs-to-haves. And so we were able to get started building the company. And a lot of people just came along for the ride without having to have us build the thing that they wanted in the first place.

24:50 – Listen to your customers

There are two ways to listen to your customers: capitulating to everything they want, or trying to understand the fundamental problem they’re having.

I really try to separate what it means to listen to a customer versus hear a customer for what they’re actually trying to communicate to me. So I guess, how I differentiate this in my work day-to-day is, if we just listen to our customers, we would build everything they ask us to build. I would love to have a button right here. “Can you do this analysis with my blood work?” Or, “Can I get this report?” I mean, there’s so many things that they ask for. And that’s just listening to them and saying, “Cool, yeah, we’ll go do it.” I think really hearing them is trying to understand what is the fundamental problem underlying why you’re asking for this in the first place. In that customer’s example, he just didn’t want to change his day-to-day. There was not actually a problem there. He was just being lazy about it or he just thought, “Hey, I would love for this to fit in my existing workflow.” But from a product standpoint, I think it’s really good to differentiate listening to their ideas versus hearing the fundamental emotions and the problems that are underlying why they’re saying things in the first place. There’s usually some other kernel of truth there that we can get at, that we should try to get at, to do our job well as product managers and product builders.

27:40 – Startups push people to become leaders

The nature of startups means people are often pushed into leadership positions even if they don’t feel ready.

I think the zero-to-one moniker is interesting, because it’s usually talking about product, finding product-market fits, finding a way to get some kernel of customer base that you can use to go raise money or bootstrap your company, et cetera. But I think the other zero-to-one that comes in is when you have built something that’s kind of working and it’s time to grow your team. And then you have to grow up as a leader to become an adult and become the person that is going to be out, not necessarily working on the bits and bytes of pushing code around or pushing pixels around, maybe you still do some of that, but you really have to transition, I think, the emotional disposition and the way that you use your time on your company to be building up the machine that it is really your organization, and the way that you grow the people inside of your organization to be the ones to actually do the building and the delivery of the product. So this was such an interesting journey for me. I mean, I think I got thrust into what it was like to try to become a manager having never managed people. You try to be an executive or a leader, whatever you want to call it, without ever having been an executive or a leader before. So much of, I think, my personal growth in the last, call it decade or so, was finding myself quite in the deep end trying to run a company.

37:39 – Understand yourself to lead your business

Scott said becoming a better leader isn’t always tactical. Sometimes it’s just about understanding yourself better.

I’m really not sure there’s tactical things that I did to get me better at doing the context switching and being okay with not being great at it. It was really needing to understand a little bit more about myself and the fact that there are many constituent parts of me and pieces of me, and understanding that I was necessarily needing to nourish and develop ones that I maybe didn’t value about myself. I thought maybe they could be good, but I was really just wanting to lean on this one that I knew I was comfortable with. And so, yeah, it was less tactical for me, and it was more on the psychology end of just coming to accept that you are more than just this singular part of yourself. And it’s maybe uncomfortable to be in these different parts, these more emotionally present parts, these slower parts that don’t need such a quick feedback loop of success, just to sit in those and be okay with those and really emotionally cultivate those. Doing more meditation, just not getting so ramped up at work, right? Just having much more slower disposition around things.

39:42 – It’s easy to avoid uncomfortable things

Ben said ignoring uncomfortable things is a natural instinct for most people, but if you want your business to succeed, you can’t avoid problems.

It’s really easy to avoid the things that are hard, that should be getting worked on, and revert to the things that feel comfortable, that might feel like they’re in a wheelhouse or in a certain skill set and go, let’s use the HR policies thing, “I know I should be focusing on people ops, but instead I’m going to jump in. I know this thing and I got to get in the base. I got to go see what’s going on there, ship some code, do a couple pull requests.” It makes you feel good and it makes you feel productive because you also know you’re good at it. And not from a, “Oh, I think I’m so good.” You know that you’ve spent time learning it. And so it’s really easy to start to rationalize, “I’m doing great work.” But in the end, everything else starts to suffer and the company will start to suffer from not having people ops or not having whatever the time would be better focused on, and then handing off trust.

43:07 – The personal transformation of a startup leader

Startup leaders must be willing to use the company as a platform to work on themselves and become better at their jobs.

When we talk about zero-to-one, to me, that is the beck and call. It’s, are you ready to launch yourself into this personal transformation to be able to become the leader, not on your own schedule, but on the schedule that almost the market dictates? I mean, I think people get attached to these rocket ship companies, not necessarily because they want to, but because they just are able to hit on something that it goes fast in a way that they didn’t expect. And you’re just necessarily along for the ride and you’re trying to get your own personal psychology and your own personal work acumen up in a way that you’re about to change roles every couple months. You’re going to be bad at them by default, because you’ve never done them, you didn’t go to school for them. And I think going through that transformation is ultimately what startups demand from us. It’s, are you willing to use the company as a platform to work on yourself, to understand more about yourself, to change in a way that you may not be ready for, but that you’re asked to embrace the suck and know that you’re going to be better off for it on the backside, even if in the short term it’s not that fun?

47:17 – Going from private to public

When your company goes from private to public, there is a perceptible shift, even if most of your processes and dynamics stay the same.

I think too, there’s an emotional changing of the guard when you do sell your company that it’s not your baby anymore, it’s somebody else’s. And to be honest, that changes relatively quickly, I mean, within the first couple months, I think it was pretty clear. Even though we were largely functioning exactly the same as when we were private, I think there’s something about the people that join a startup, especially one that was as small as ours. I mean, we were 15 people. They joined that because they want to be part of building something and feeling like you’re in that zero-to-one phase. And when you get bought, I think a large part of that goes away, whether you want it to or not. I think that there’s just this sense that you’re swimming in a much bigger pond with much bigger fish now. And even though you might eventually grow to become one of those bigger fish, it’s not you against the world anymore. You’ve got a protector, you’ve got a financial supplier, in a way, even though we really didn’t need that. But yeah, it can be a much different feel.

Scott Klein (00:06):

At the zero stage, yeah, it’s really this emotional, just nugget of wisdom of, “I can’t be the only one that thinks this way. I cannot be the only one that feels this way. But it is very special and I’m sure a bunch of other people are feeling this way. Why has no one gone to solve this?” So that’s really the zero story of, we didn’t do it to set out to build a big company, we didn’t do it to set out to build an empire or a venture-backed unicorn. We really set out to solve that emotional struggle that we were experiencing in a way that we felt the world needed.

Ben Grynol (00:45):

I’m Ben Grynol, part of the early startup team here at Levels. We’re building tech that helps people to understand their metabolic health. And this is your front row seat to everything we do. This is A Whole New Level. As a startup, one of the hardest stages to go through is this idea of zero-to-one. It’s the idea when you’re really trying to get traction. Any source of signal that says, “Hey, what you’re doing is working. You’re actually solving a problem for people.”

Ben Grynol (01:25):

Well, for Scott Klein, head of product, Scott was co-founder and CEO of Statuspage, a YC company, who went through YC, Y Combinator, in 2017. And so shortly after founding the company, shortly after the zero-to-one stage, Scott’s company was acquired by Atlassian, it went from a small startup, this zero-to-one phase, to a large tech company where things were very different.

Ben Grynol (01:48):

Most startups fail, that’s the reality. Sometimes companies fail because of team dynamics. Other times companies fail because they run out of capital, and sometimes companies fail because the timing isn’t right. We’ve seen this with so many different cases. Scott and I sat down and discussed this idea of zero-to-one, why it’s so hard to build and what companies can do about it, what we’ve done about it, what we are doing about it to really cross the chasm. It was a fun conversation to dig into this world of startups and think through how this past experience shape future experience, what insight should you lean into, and where should you back off. Here’s where we kick things off.

Ben Grynol (02:35):

There have been a couple things that I’ve been thinking about with zero-to-one, and thought it would be good to chat about. But more importantly, this idea of zero-to-one is something that you’ve been through, been through it as a founder, you know how hard it is to build a company. And I don’t know if people take it for granted, but zero-to-one is an insanely hard stage because you’re just trying to get enough traction to say, “Could there be something here?” So, the idea is to have a conversation around this idea of building a company from the ground up and just walk through, why is it so hard and what are some of the things that evolve as companies go through all these different phases of growing?

Scott Klein (03:17):

So I guess for some context, in 2013, I started a company called Statuspage, and the product premise was that all of these web companies and technology companies were around, they had this very specific problem that when they had unplanned downtime or scheduled maintenance for their systems, they needed a specific tool to talk about what was wrong and why. You can imagine your data center goes dark and your phone systems, your support queue, everything gets lit up really, really bad in a way that you don’t want your customers to have that experience.

Scott Klein (03:50):

And so it was really important, I think, when we started this company just to solve this narrow problem to start, and then we could expand out from there. I wish I could say that the idea was original to us, but it most certainly wasn’t. I think that we had experience working as developers and as product managers wanting to lean on third party services and getting met with resistance because there’s this big trust barrier of, we don’t know how these people are running their systems, we don’t know if they’re good. If we’re going to rely on this third party, can we built a product around that?

Scott Klein (04:22):

And at the time I think the web was still growing up to really come to embrace what it meant to rely on third party systems. And we just saw that there was this massive gap, this trust battery that was non-existent, in a way, because you didn’t have any insight into how the third parties were operating. Specifically when stuff did go wrong, how do they conduct themselves? Are they transparent about it? Do they like to talk about it or do they tend to hide from it and really diminish the impact?

Scott Klein (04:48):

And so I had experience as a developer and as a product manager that really frustrated me and we just thought there’s got to be something here. Somebody needs to be serious enough to go do this and put a realistic price tag on it. And why shouldn’t that be us? So that was the entire genesis of what we did with Statuspage. Very niche product to start. It wasn’t any new idea, we just felt, “Hey, this is a problem enough that people don’t go out of their way to do it. And so somebody needs to go solve this in a very real way.”

Scott Klein (05:16):

One of the things that I do tell people a lot about starting Statuspage is that we never had any and ambitions to build this massive company. We were just so passionate and on fire about solving this specific problem, even if it was just for ourselves, just to give it to the companies that we were relying on to use and say, “Hey, you should use this.” I remember at one point when we were working on it, when my brother and I got started building Statuspage, we were still contracting. We found this really cool client who would let us work for about a week or a week and a half at a time, and then he would give us two weeks off.

Scott Klein (05:49):

And so we were paying the bills with our contracting work, and then we’d go build Statuspage for the other three weeks of the month. And I remember turning to my brother at one point and saying, “Dude, if at some point in the far future, this thing caps out at $10,000 a month in revenue, I’m going to be happy, and our lives are going to be forever changed.” So I think that there’s a purity of us getting started just working on a problem that we felt there needed to be a solution. The internet would be a better place. At the very worst case we, would open-source it, and hopefully someone would come up behind us and maybe help us work on it to get it out to the masses.

Scott Klein (06:23):

So, that’s the genesis story. I’ll fast forward really quick to, we got accepted into Y Combinator summer batch that year. Yeah, Summer of 2013, we did the Y Combinator class, that’s back when it was about 50 companies per batch. I know it’s about four or 500 now. Obviously they’ve scaled quite tremendously in terms of the number of companies that they’re letting through.

Scott Klein (06:42):

We ran the company through Y Combinator and then actually kind of bootstrapped it afterwards. We didn’t raise any money. We tried but failed, in a way, but we were doing enough revenue, and a couple young people in their 20s, not a lot of requirement in terms of lifestyle for money. And so we just put our heads down, and we knew we weren’t going to run out of money and we could see the revenue tracking up into the right.

Scott Klein (07:03):

And so we basically bootstrapped the company for the next three years and then eventually were acquired by Atlassian in 2016. So Atlassian, the famous makers of Jira and Confluence and Trello, and a couple other things. Yeah, so we did various development and product management things inside there, but that’s the context for starting the Statuspage company.

Ben Grynol (07:21):

So let’s go to the zero stage, right? Was there an insight? Was it that you would see a 404 page and you’d be like, “What is this? It’s just nothing? Nothing exists?” How did you identify that there was a problem? And then what were some of the steps that you took as far as saying, “Let’s see if there’s something here. How do we start to prove our hypothesis that this is a problem that exists?”

Scott Klein (07:46):

Yeah. I think on the zero stage, one of the things that I just remember so keenly was my emotional state when I came across companies that were doing this, and doing it well. Companies like GitHub and Heroku had spent their own design and development time to build their own custom-built status pages. And when they did it, and they did it well, it just engendered a level of respect and really love for these companies, because I felt like, hey, if I’m going to build my business on top of yours, you’ve gotten so far of your way to show me we’re not going to be perfect all the time, but when this does happen, we’re going to be here for you as best we can.

Scott Klein (08:28):

And it was really such a level of them committing to being their best self for me, that there’s no way I was going to use any company beside GitHub or Heroku to do my hosting and my code source. That was just so obvious to me. And I think just that emotional awareness of, this is a relationship that I’m going to have with this company. And they’ve really gone out of their way to do a relationship thing for me, to really build that trust with me and tell me they’re going to show up.

Scott Klein (08:55):

In terms of a generalizable thing, when I think about Levels, it’s maybe a similar story around, when you think about something like expanding access to CGM, for example, it’s certainly possible to go do. In all of these zero-to-one stories, it’s almost always possible to go do something on your own if you wanted to, but the fact that someone’s gone so far out of their way to make it so seamless and so useful, there’s more than just the commercial value there that gets built. I mean, I think when I look at and think about how people talk about Levels online, there’s a similar kernel of, “I feel like you’ve gone so far out of your way to make my life different that I’m really entrusting you with a lot of things.”

Scott Klein (09:33):

I think as we expand into things like blood work and nutritionist and whatever we’re going to do in the future, that trust is really going to extend to each of those things. And I think it’s because of that emotional mismatch of, “I really want to a thing to exist, and you’ve obviously solved it in such a good way that I think about you differently as a company now, and you’ve made my life so different.”

Scott Klein (09:52):

But at the zero stage, yeah, it’s really this emotional, just nugget of wisdom of, “I can’t be the only one that thinks this way. I cannot be the only one that feels this way. I don’t think it’s a special thing that I’m feeling this way or a unique thing, I should say, but it is very special and I’m sure a bunch of other people are feeling this way. Why has no one gone to solve this?” So that’s really the zero story of, we didn’t do it to set out to build a big company, we didn’t do it to set out to build an empire or a venture-backed unicorn. We really set out to solve that emotional struggle that we were experiencing in a way that we felt the world needed.

Ben Grynol (10:27):

Yeah. It’s funny because when you would see those, I remember seeing custom built status pages of companies who would put in the effort, and it felt delightful. You would see this and it felt like this delightful touch point where you’re like, “Oh, they care enough about our lens as a public of what is going on with this company right now.” That it wasn’t just everything’s broken, and the doorbell effect of, it could be ringing all day, you could hit refresh on that thing as much as you want and nothing is going to change.

Ben Grynol (10:57):

In a lot of cases where it was really frustrating is you’d come back to some of these companies’ pages 20 hours later, an absurd number of hours, and it would just be the same thing. And you’re like, “No idea.” You’re searching Twitter to be like, “Is there a status update as far as what’s going on right now?” That’s a frustrating experience.

Ben Grynol (11:16):

But when you decided, so you had the insight, you’re like, “Hey, I think there’s something here.” What were some of the steps that you took from zero to work towards proving the hypothesis? What were the micro-steps, knowing that so many people go to side note… Just talked to a founder on Friday about this, where he’s so far down the path of overbuilding on what he’s working on that you go, “Let’s back up. There’s a lot easier ways of figuring out how to build against something.” So what were some of those steps that you took from the zero stage to build against your insight?

Scott Klein (11:53):

Yeah. I think there’s a couple things here. I think the first thing is that we looked at, there was already one provider that you could pay money for to get your own status page, if you wanted to. And I think coming from this environment, there was such a good match of founder and problem for my brother and I. And so we had a lot of people in our network that we could put open source solutions in front of them, or we could put the one commercial solution in front of them and say, “Well, you don’t have a status page, you’re telling me that you want it. You have the option to go buy this thing right now. What gives? What’s the delta? What’s the diff? Why are you not doing it?”

Scott Klein (12:31):

And so we started to get just a sense for what’s even important into them? Before we even laid a line of code down, why is this even a thing that you’re not acting on? There’s some gap in between the future where you want it to be and where it is right now that’s causing inaction. So it’s possible that these solutions existed, but they didn’t quite get beyond the gap of, hey, this is going to make my life better. It might make it different, but that doesn’t necessarily mean better.

Scott Klein (12:55):

And so people were just sitting on an action. This is the number one competitor that every startup has, is just inaction or stasis with how things were. And so I think through those conversations, we were able to triangulate around, I think someone just needs to do this and do it seriously enough that people believe them. I think the reason that they didn’t want to deploy an open source is that it was yet another thing to maintain during their incident. Does anyone have the login to the… They wanted no one to have to worry about, do we need to scale up the EC2 resources or whatever for our status page where we were having all of that stuff they just didn’t want to have to deal with.

Scott Klein (13:30):

And so, yeah, a pay provider needed to be almost expensive, it needed to feel very real, and it needed to be so hands-off that you would it would require zero mental energy when it came to incident time. And so we just, I think through validating, hey, if there’s existing solutions and people aren’t buying them, it’s not that there’s nothing there, it’s just that you need to learn why that’s not working to begin with.

Scott Klein (13:51):

So yeah, we had a number of people that we had a lot of conversations with. And then once you get to a thesis about why people aren’t acting on it now, you kind of know where to go build and where to put your time and effort because you can’t just be the same, same as the existing solutions and expect something to be different. We needed to differentiate in a way that felt real to them. It needed to feel like we were serious about this company, it needed to feel like the price tag was real, that we were going to show up for them, and it to feel like it was so hands-off that they just weren’t going to have to think about it. So I think that’s where we spent the majority of our time focusing.

Scott Klein (14:22):

But two other characteristics of this were, we could build it, so we had the resources to actually go lay down some code and go test our hypothesis. And the second is that we had really good friends in this industry that we knew were going to be our first customers or at least were going to give us some actionable feedback.

Scott Klein (14:39):

And so I think we were just lucky in that… You can call it lucky, but I think when you have that founder product fits, those things just generally tend to fall in naturally, where you’ve got very clear steps to go build something, test, build some more things, test, build something, test, start charging, figure out why people aren’t buying it, or if they want something different. So anyway, I think the alignment of all those forces really allows you… There’s no single defining characteristic to go from zero-to-one, but I think that the alignment of all those forces really helped.

Ben Grynol (15:08):

The fact that you started by talking to people in your network. I mean, it sounds cliche, it’s YC’s mantra, it’s what you hear in every startup circle that a person would be in is, “Go talk to users. Talk to users. Talk to users, get feedback, talk to users. And once you’ve talked to users, go talk to more users.” The thing that you hear often where people make mistakes is, so you and your brother had the ability, you had the talent to be able to go lay down code.

Ben Grynol (15:38):

And it’s so easy to dig into the idea of, “Okay, let’s just start building.” And you start building against something without having any idea of what you’re building. Hypothetically, it takes four weeks, that’s usually not the case. More like four months, six months. People go into a cave and then they surface and they’re like, “Ta-da,” and they’re just waiting for this grand reveal, and everyone’s like, “This thing doesn’t even work. It’s a wheelbarrow without a wheel. What are you doing? That’s not going to carry anything.”

Ben Grynol (16:05):

And that is a big mistake that people make. But once you got to the point where you have enough insight and you wanted to start building against it, what did that look like when you went from the zero stage into YC? How much traction did you have, and then how did you start to iterate and build out against that to get to the next stage and the next stage?

Scott Klein (16:29):

So when we got into Y Combinator, I think what eventually got us in was we had an interesting mix of traction so far. So I remember when we went to our interview, we had 20 people paying us $50 a month, I very clearly remember this. But what was interesting was that we had companies like Datadog, who are now public, with Shopify, who are now public. This was the initial cohort of 20. And I think the fact that it hit such a nerve with them, that they were willing to take such a bet on such a small company, we had some indication of, this was going to expand to be a much larger fire eventually.

Scott Klein (17:10):

And so it’s not that you need the volume of signal at the start, it’s just that you need the right signal and the right direction. And I think going into the interview, they want to talk about metrics, but really it was a proxy for, who’s almost given this approval to your product so far? So we were able to name drop in a way that I think got them to think, “Okay, we don’t even have to make the mental leap here, someone has voted with their dollars to do so.”

Scott Klein (17:33):

And more specifically, you’ve got this public-facing status product, it’s voting with your reputation in a way to get Shopify to put their reputation eggs in our basket. I think it was just a big deal for us. And so, yeah, it wasn’t that we had a ton of volume of signal to get into Y Combinator, it was in the right direction with reputable names. And so that certainly helped us out.

Scott Klein (17:53):

The other thing that I’ll say about maybe early traction is that, there’s a very scary period, I think, in startups life from zero-to-one, where you can kind of get whipped around by well intentioned people that just want you to build a product for them and not actually for a wider basis. I’ll give you one very clear example.

Scott Klein (18:14):

We got contacted by a major technology company who was happy to pay the enterprise price tag. It was going to be thousands of dollars a year. And we had many phone calls with them. And after the second phone call, they basically came back to us and said, “You’re young kids, you have no idea what you’re doing. None of these incident states or component states line up with ITIL or ITSM.” And they were throwing a bunch of these big acronyms at our face to say, “Hey, our industry has gone in this direction. You have no idea what you’re talking about. You’ve built your product around the wrong primitives.”

Scott Klein (18:48):

All of this stuff, and they wanted us to just basically create the feature request that comes with it. Can you create custom incident states? Can we do custom workflows around components? All of these things that, as a startup, you’re tempted to go, “Oh man, this is a big, publicly-listed company, would love to be able to put their logo on our website. Would create this massive backlog of work for us to do in the short term. Most importantly, is very, very, very much committing yourself to long term maintenance of these features.”

Scott Klein (19:14):

You hear things like custom workflows, custom states, custom configurability. And I think through my work as being a developer, I knew the amount of debt that that would get us into in the long term. So we said, “Hey, I hear what you’re saying. I’m really sorry, it’s not going to work for you right now.” We’re just going to have to say we can’t do this for you right now, we’ve got other priorities to deal with.

Scott Klein (19:37):

For better, for worse, we kind of stuck our head in the sand and just kept building for the smaller customer, knowing that eventually we would get to the bigger customer features one day. And lo and behold, about 10 weeks later, guess who came back to be a customer? That same exact person that berated us on the phone and told us, “You’re young, you’re inexperienced, you have no idea what you’re talking about.” At some point, they got to the conclusion that, I think, “Hey, this problem is big enough that we’re actually able to change our own way that we route around this to use their product. Because right now we have nothing. We could go to use something. And so it’s important to us that get to the point that we have this in front of our customers in a way that we’re able to change our behavior slightly in the short term.”

Scott Klein (20:20):

So all that to, I think, say, one of the things that I’m happy that we did was we made a decision to focus on the smaller customers first, because we knew they weren’t going to have such enterprise feature requests. And what we found along the way was that a lot of these enterprise feature requests were actually just nice-to-haves and not needs-to-haves. And so we were able to get started building the company. And a lot of people just came along for the ride without having to have us build the thing that they wanted in the first place.

Ben Grynol (20:49):

Yes. While the idea of going after the whale and building against the whale is a startup death spiral, you hear of it so often where people are like, “We got them. We have the big, blue fin tuna on the line,” and they’re reeling it in. And then it gets to the boat and they don’t even know what to do. And they missed all the other fish, right?

Ben Grynol (21:12):

It’s a really poor practice to get into, is the idea of building towards a company’s needs. Actually, maybe let’s drill into that. Taking people’s feedback into account versus building against their needs are very different things. So taking their feedback into account just like, “Great. I appreciate why you are suggesting this.” And then you can decide whether you accept or reject that based on your roadmap, based on initiatives, based on all these other things.

Ben Grynol (21:39):

When you just build against it, you go, “We were kind of going here,” and you get one degree off, and the next thing you know, you’re a mile off course. And assume a whale is so high leveraged that all of a sudden they’re like, “Nah, we’re good.” And you’re like, “Wait, we just spent six months trying to build against everything because you are going to pay the price and then now you’re not even there.”

Ben Grynol (22:01):

It’s very much a startup death spiral because every week that you’re not getting closer to product market fit, every week that you’re not getting to that next stage is a week of lost time. And it’s expensive, as the team grows too. As it’s more than you and your brother, in your case, it’s more than a small group of founders. As teams grow, it gets more and more expensive and dangerous to be off track on things like that.

Scott Klein (22:28):

Yeah. You know what? I think in our case with that big customer, we actually got quite lucky. But one of the books that I just absolutely loved that I tell everybody to read, especially product people and people that get miffed by politics a lot, usually there’s some good overlap here, the book’s called, The Righteous Mind, and it was written by Jonathan Haidt, I think he’s out of NYU.

Scott Klein (22:50):

And the book talks a lot about how our abilities for logic and reason evolved almost as a social characteristic to get people in our group, our in-group, our tribe, whatever you want to call it, to be on our side for the emotional things that we feel. I think the book tries to clearly out, and they do this experimentally, that we have these urges, we have these feelings, we have these intuitions, and then we use logic and reason to help recruit people to our team, to get what we want.

Scott Klein (23:22):

You would think it would be backward, that we have this environment, we experience it, we see something, we hear something, logic and reason feed into our emotions about how we feel about it. But the book lays out a pretty good case for it actually being in reverse, that the urges and the intuition, the feelings happen first, and then we use logic and reason afterwards.

Scott Klein (23:39):

In a product sense, this is the scientific reasoning why the build faster horses phenomena exists, is because people have this feeling of, “I just want to get to places faster,” but then their logic and reasoning will just grab at the most proximate thing that they can think of. And sometimes you can get creative about it, and a car out of it. But from the customer’s standpoint, when you think about when you’re a startup< that customer in particular, or the person we were talking to who tried to get us, to buy our product. You can think about it, the urges and the feelings that they had were, “This isn’t going to be exactly like I do my job right now.”

Scott Klein (24:18):

And then it stops there. And then they’re going to look for anything in the reasoning or logic side that can help recruit us to their cause, right? What they’re saying is, “I don’t necessarily want to change my job. If I had my perfect world, I want everything to fit like I do it right now.” That’s the feeling. And they were trying to get us to change our product to be more for what they want.

Scott Klein (24:38):

But I think coming to understand that that’s not necessarily how they will operate, if you just give it some time, or you give them the experience that they can actually use the product. And so, from my time working in product, I really try to separate what it means to listen to a customer versus hear a customer for what they’re actually trying to communicate to me. So I guess, how I differentiate this in my work day-to-day is, if we just listen to our customers, we would build everything they ask us to build.

Scott Klein (25:06):

I would love to have a button right here. “Can you do this analysis with my blood work?” Or, “Can I get this report?” I mean, there’s so many things that they ask for. And that’s just listening to them and saying, “Cool, yeah, we’ll go do it.” I think really hearing them is trying to understand what is the fundamental problem underlying why you’re asking for this in the first place.

Scott Klein (25:25):

In that customer’s example, he just didn’t want to change his day-to-day. There was not actually a problem there. He was just kind of being lazy about it or he just thought, “Hey, I would love for this to fit in my existing workflow.” But from a product standpoint, I think it’s really good to differentiate listening to their ideas versus hearing the fundamental emotions and the problems that are underlying why they’re saying things in the first place. There’s usually some of other kernel of truth there that we can get at, that we should try to get at, to do our job well as product managers and product builders.

Ben Grynol (25:52):

So with product, right? As a company grows, so you go zero-to-one, you go one to 10, you go 10 to 100, 100 to infinite, you become publicly traded. But that is iterative as far as product, product market fit, getting traction in that way. One of the things that is very challenging with startups, not just getting traction, but the idea of actual company building, and a team scaling with a startup.

Ben Grynol (26:20):

And the reason why it can be so challenging is, as much as there’s exponential growth from, let’s say, whatever North Star metric it is, let’s just call it revenue in this case. It’s a SaaS company, so revenue, right? Well, subscriptions revenue. But the goal is to grow that exponentially. In doing so, there’s also exponential team growth. Teams grow time and time and time again. And that becomes very challenging because roles change, roles evolve, areas of responsibility change. And you’re trying to build a culture, something we’re focusing so deeply on right now.

Ben Grynol (26:55):

But how do you think about this idea of, when teams scale, some of the challenges that come in that don’t feel natural, right? We’re not a coniferous tree that takes 100 years to grow to 40 feet. We’re a piece of bamboo that grows to 100 feet in five weeks, right? Not a perfect analogy, but that’s basically the idea of a team, where you’re sprouting up and you’re growing so high, so fast, so big, and things are changing with that bamboo. They’re changing so much in that trajectory, compared to something that’s just old and established and well rooted in the ground. What are some of the challenges that you saw firsthand as your team grew?

Scott Klein (27:40):

I think the zero-to-one moniker interesting, because it’s usually talking about product, finding product market fits, finding a way to get some kernel of customer base that you can use to go raise money or bootstrap your company, et cetera. But I think the other zero-to-one that comes in is when you have built something that’s kind of working and it’s time to grow your team.

Scott Klein (28:03):

And then you have to grow up as a leader to become an adult and become the person that is going to be out, not necessarily working on the bits and bites of pushing code around or pushing pixels around, maybe you still do some of that, but you really have to transition, I think, the emotional disposition and the way that you use your time on your company to be building up the machine that it is really your organization, and the way that you grow the people inside of your organization to be the ones to actually do the building and the delivery of the product.

Scott Klein (28:33):

So this was such an interesting journey for me. I mean, I think I got thrust into what it was like to try to become a manager having never managed people. You try to an executive or a leader, whatever you want to call it, without ever having been an executive or a leader before. So much of, I think, my personal growth in the last, call it decade or so, was finding myself quite in the deep end trying to run a company.

Scott Klein (29:02):

Because at that point, your things about your own psychology or your life, they’re not separate from your work, right? There’s a reason why I think people get into trying to be a founder, trying to do something high impact, trying to really spend so much of their life working on something. There’s some kernel of truth inside of us that wants to be that person to deliver that. And then you’re assertively stuck in the deep end of, “Oh, man, now I actually have employees and I have direct reports and we got to do HR policies, and I got to think about recruiting, and I got to think about being charismatic and being a leader and all this stuff that I’ve never had to do before.”

Scott Klein (29:34):

There’s a really interesting impact of that, I think, on our lives. If I could contrast the two really quick, coming from a development background, I started building Statuspage in a way that was, I’m pushing code that’s fairly deterministic. The feedback cycles are super short. I can go from thought to pull request, to code and production within a matter of hours, sometimes minutes, if I want to. And things are happening quickly, customers are happy on a short time basis. So pretty soon you transition into taking on work that is all of the opposite of those things.

Scott Klein (30:08):

It is recruiting. So you’re almost failing by default, you are working on setting the vision and the strategy and the roadmap, and you’re not going to know for three, six, 12 months, if it’s going to be correct. And the emotional pace at which you’re doing your work really slows down. And it’s almost tough to feel useful in that context. It’s tough to feel reward in that context. You wake up every day and by definition, you’re almost unqualified for your job. And everybody’s looking at you, expecting you to be very qualified and useful at your job.

Scott Klein (30:42):

And so there’s this immense mismatch. And I think the personal side gets weaved back into it, because all of your narratives about your life, who you are, what makes you useful in the context of society or capitalism, all that just comes rushing back because you went from being very useful as a developer or a designer or a product manager, whatever of the case is that made you useful in an IC contributor standpoint.

Scott Klein (31:08):

Now you are none of those things anymore, and everybody’s expecting you to be very good at what you’re doing. And so I think dealing with that mismatch of having to get up every day and go, “I’m going to try my hardest. I know I’m not qualified to do any of this stuff. It’s probably going to suck the first time, but I’m just going to put a smile on and be good about it.” That’s the zero-to-one that I think people don’t necessarily plan for.

Scott Klein (31:31):

It is very draining emotionally. And I think practically for my life right now, I’ve got a one-year-old and a four-year-old, I very explicitly chose not to be a founder again, because I knew, not necessarily the product building side of what it was going to hate to go from zero-to-one, but the organizational side of what it was going to take to go from zero-to-one, I knew I didn’t want in my life right now. I think it’s a very serious commitment to make.

Scott Klein (31:52):

And so, yeah, I think that’s the other insidious zero-to-one that maybe people don’t know it’s coming until it’s at their doorstep. And then I think it can rock you a lot harder than trying to find, even your initial kernel of product market fit, because you’re usually in your comfort to zone, you’re usually doing things that you know you’re good at.

Scott Klein (32:07):

And if the product doesn’t work out, you know what? You gave it a good shot. But the organizational to team building, the company scaling side of it, that’s the much, much, much harder zero-to-one that I think people don’t anticipate, but that they get thrust into after they find their initial modicum of truth around their product.

Ben Grynol (32:22):

Yeah. You go from being the table saw, in the suite of tools, you are one of the tools, maybe you have a couple tools. So all of a sudden, snap your fingers, Scott, you’re the contractor. Here’s all these tools, put them to work and go build a house. And then once that’s done, put an addition on. Once that’s done, get a crane and start building a skyscraper. And you’re like, “My goodness. I just happened to be the table saw. I was the table saw a month ago. And what are we doing? A skyscraper now? This is wild. I’m the contractor? What?”

Ben Grynol (32:52):

It’s a wild thing, but what were some of the things that you did to overcome some of these thoughts or as you scaled… Because there’s also the side of it when you’re not the… Let’s keep using this analogy of the contractor. One of the things that happens in startups all the time is you go from being the skill saw to the hammer, to the, name another tool, the screwdriver, and they all are tools that do different things. But you have to jump from one to the next, not from a context switching, but let’s say you’re deep in only being the skill saw.

Ben Grynol (33:25):

Let’s jump into tech, because this is getting way too abstract right now. You’ve got the ability to be really good at engineering, and let’s say you also are deep in operations, and then something totally unrelated, let’s say legal. These three things where you go and you’re not just a gap filler, but you actually have to invest yourself deeply in that thing.

Ben Grynol (33:47):

So it’s a direct trade off in skillset, in area of responsibility. If you jump from, hypothetically, if this was real, engineering, to all of a sudden, you’re only responsible for legal. And that’s a really weird and overwhelming thing to do because all of a sudden you have to almost divorce yourself from this identity that you had before.

Ben Grynol (34:07):

And it can be a really hard thing because that is how companies evolve. It’s not just hire against that role immediately. Sometimes it’s like, “Okay, Scott’s in charge of legal now.” Do you have any things that you did to overcome some of these things or do you have advice that you give other founders when talking with them of, hey, this is going to suck. It’s going to be really uncomfortable. It’s really rewarding, but you’re going to feel totally overwhelmed by this. And know that it doesn’t really end as you go through all of these cycles?

Scott Klein (34:36):

Yeah. Well, the first thing I’ll say is that I don’t know that I did this particularly well. I got to be honest, I don’t know that I had the wherewithal to do this well. I think I’ve gotten a lot better at it. I think I’m better at it now than I am, but it was very difficult. I think the most impactful thing, to be honest, that I did was I started going to therapy.

Scott Klein (34:59):

And I say that because I actually started going, for a tangential reason, to the company, but immediately all of the work stuff starts to come out in these sessions. And it was the first time in my life that I think someone had told me that the piece of me that really gets value from work and being good at being an engineer is just one of many pieces of myself.

Scott Klein (35:23):

And I started to think about and recognize that the mode that I was showing up in at work was representative of a single piece of my identity, and that there were many other pieces that made up the constituent Scott. And this was months, by the way, of going in every week to talk to somebody about my life and where I had come from, and really learning that coming from a background of marching band and chess and video games, doesn’t lend you to being the cool kid in high school and wanting to be in that position, and then finding some usefulness in college.

Scott Klein (35:55):

And my personality really leaning into that thing that made me valuable. All of a sudden it was, wow, you’ve got this thing that you love to do, which is program computers, and now the entire world loves you for it, and you’re going to go make some money because of it. There’s this massive switch that happened for me right after high school that I think I was leaning so hard into as a tool, which is great, because you find some usefulness in your life and it’s really easy to go about your life doing that.

Scott Klein (36:21):

But then you get into a position where you have to unwind that or unlearn that, or at least not lean so heavily on it as a singular dimension of your life, that it starts to cause problems. And I think that going to therapy was the first time I had realized, “Oh, man, the company, what it needs of me is actually not for me to be a skill saw, it needs me to go be a crane operator.” The nuance is not that I was necessarily bad at being a crane operator, it’s just that I kept looking at the skill saw and going, “But I could be doing that. I could be doing the thing that makes me feel good.”

Scott Klein (36:51):

And especially on the hardest days. Fast forward a couple years into the company, and I’m splitting my time in between trying to be CEO and also still taking care of the technology. The most non-obvious killer, I think, of a leader at that stage is feeling bad about the leadership work that they’re doing and then reverting into going back to the code or going back to design or going back to a place that’s comfortable to them so that they can feel good about themselves.

Scott Klein (37:18):

There’s a big psychology component there that I wanted to make. I had to learn about and understand, this isn’t about you actually allocating your time, it’s about allocating your emotional disposition and getting used to the fact that it’s going to kind of suck. And you’ve got to find a way to be happy with yourself, even if you’re bad at your job every day.

Scott Klein (37:37):

To answer your question, I’m really not sure there’s tactical things that I did to get me better at doing the context switching and being okay with not being great at it. It was really needing to understand a little bit more about myself and the fact that there are many constituent parts of me and pieces of me, and understanding that I was necessarily needing to nourish and develop ones that I maybe didn’t value about myself. I thought maybe they could be good, but I was really just wanting to lean on this one that I knew I was comfortable with.

Scott Klein (38:07):

And so, yeah, it was less tactical for me, and it was more on the psychology end of just coming to accept that you are more than just this singular part of yourself. And it’s maybe uncomfortable to be in these different parts, these more emotionally present parts, these slower parts that don’t need such a quick feedback loop of success, just to sit in those and be okay with those and really emotionally cultivate those. Doing more meditation, just not getting so ramped up at work, right? Just having much more slower disposition around things.

Scott Klein (38:40):

Anyway, that was a bit of a ramble, but that’s really actually what I was left with, for my entire time through Statuspage, it was a period of self discovery in a way that I had to understand why I wanted to be spending more or less time on things at work and just understanding the history of my childhood and how that fed into how I saw myself as having value to the world.

Scott Klein (39:00):

Anyway, all of these things got uncovered through the course of me starting a company. And I think in the intervening years now, I feel like I’m a much more productive leader, not because I tactically know the tricks or the things to do, it’s that I’m emotionally just able to spend more time with myself doing presentations or having conversations with people. Whereas before I might have seen that as an impediment to me getting stuff done. Now I’ve learned to really value those things and know that I need to set myself emotionally up to be in a good place to have those things and feel valued for them, if that makes sense.

Ben Grynol (39:35):

Yeah. It’s wild to hear that, because it’s something that I’ve seen in the past. I’ve seen a lot of friends who are founders go through this too. And it’s really easy to avoid the things that are hard, that should be getting worked on, and revert to the things that feel comfortable, that might feel like they’re in a wheelhouse or in a certain skill set and go, let’s use the HR policies thing, “I know I should be focusing on people ops, but instead I’m going to jump in. I know this thing and I got to get in the base. I got to go see what’s going on there, ship some code, do a couple pull requests.” It makes you feel good and it makes you feel productive because you also know you’re good at it.

Ben Grynol (40:16):

And not from a, “Oh, I think I’m so good.” You know that you’ve spent time learning it. And so it’s really easy to start to rationalize, “I’m doing great work.” But in the end, everything else starts to suffer and the company will start to suffer from not having people ops or not having whatever the time would be better focused on, and then handing off trust.

Ben Grynol (40:36):

And I think it’s one of the biggest challenges with startups and scaling with startups is, let’s F1 racing as the analogy, if you’re a good driver and somebody else is a good driver as well, with F1, the team is the… What do you call them? The pit crew. The pit crew is equally as important to the driver, right? Nobody will recognize that. But if the gas doesn’t go in, if the tires don’t get changed, those are seconds that will make you lose the race potentially.

Ben Grynol (41:06):

And if somebody goes, “Cool, you used to drive, now you’re doing the gas, and now you’re changing the tires.” The car comes into the pit, the driver’s there, and instead of changing the tires, some guy starts trying to crawl in the cage and being like, “Oh, I’m just going to drive it.” You’re like, “What? What are you doing? No. We all agreed you’re changing the tires on that one.”

Ben Grynol (41:27):

And so the way to be successful is just be like, “I love driving, I used to drive. I’ve been tasked with being the tire changer.” And you invest yourself so deeply in being the best tire changer you could possibly be and no different. And then when it’s time to be the gas filler, the next role, the next role, maybe it’s just not even in the pit, you have to invest yourself so deeply in that next role.

Ben Grynol (41:52):

And I think this where sometimes things get mistaken. It’s not a demotion, it’s not that somebody’s being relegated when it’s, “Well, you used to drive and now you are doing tires.” The idea is you are still a part of this giant machine. And in most cases, you’re being put in charge of the tires because somebody goes, “Man, we need somebody in that role that we trust to change the tires. We need somebody in that next role.”

Ben Grynol (42:15):

And so when you keep getting put in these different positions, it’s not a, “Hey, I don’t have the skill to do this.” It’s, “I don’t really know this, but I have to go figure this out because everyone’s trusting that I’m the person to figure it out.” It’s such a dichotomy in our own psychology of what we’re good at, what makes us feel good versus what we should be doing to move things forward.

Scott Klein (42:40):

Yeah. It’s so funny, whatever you feel about people like Mark Zuckerberg, the most tremendous thing for me is not that he was able to grow and scale Facebook to corporate entity, it’s that he had to grow up way faster than he probably wanted to, would be my guess. And I’m always just amazed at people that go through that amount of transformation in their life, in that short of a time period.

Scott Klein (43:05):

But I think that’s really, when we talk about zero-to-one, to me, that is the beck and call. It’s, are you ready to launch yourself into this personal transformation to be able to become the leader, not on your own schedule, but on the schedule that almost the market dictates. I mean, I think people get attached to these rocket ship companies, not necessarily because they want to, but because they just are able to hit on something that it goes fast in a way that they didn’t expect.

Scott Klein (43:35):

And you’re just necessary along for the ride and you’re trying to get your own personal psychology and your own personal work acumen up in a way that you’re about to change roles every couple months. You’re going to be bad at them by default, because you never done them, you didn’t go to school for them.

Scott Klein (43:49):

And I think going through that transformation is ultimately what startups kind of demand from us. It’s, are you willing to use the company as a platform to work on yourself, to understand more about yourself, to change in a way that you may not be ready for, but that you’re asked to kind of embrace the suck and know that you’re going to be better off for it on the backside, even if in the short term it’s not that fun?

Ben Grynol (44:13):

Yeah. One of the hardest things, and this is something you would’ve seen too, is a person works on themselves, they disconnect their identity as being, what they do with work, whom they work with, being a founder. You start to disconnect all these things and parse them out. But one of the hardest things is going from being a private company, which you experienced, to all of a sudden, snap your fingers, publicly traded.

Ben Grynol (44:40):

The game is not the same. It doesn’t feel the same, it doesn’t act the same, it is very different. And especially when you are a part of, well, of course, going through some merger or acquisition will, you become part of another company. But what did that feel like when you went, “Hey, we used to just be autonomous and I could do whatever was necessary,” to all of a sudden being publicly traded and having a totally different outlook on execution?

Ben Grynol (45:08):

The reason that I ask is, I think it happens frequently where, assume that team members can jump roles, team members can ramp up through all the phases in being privately held. Zero-to-one, one to 10, 10 to 100, and just make these leaps. But there is a drastic change of that, “Hey, we’re publicly traded,” and it’s, you’re not a scrappy startup. And I think that can be a really hard transition. So did you see anything along the lines of that, personally or with different team members, where it was just, “Whoa, this is not the same game we were playing before,” and not being able to make that leap as things changed?

Scott Klein (45:47):

I’ve heard of wildly different outcomes of these things happening. Yeah, so I think you’re alluding to, we got started with Statuspage in 2013. We got bought in 2016 by a publicly traded company. What was life like on the other side of that? One of the things that we talked to lasting about a lot during the process was just the cultural alignment. I think we had a very bootstrapped, flat mentality.

Scott Klein (46:10):

And I think they still were in large regard trying to operate out of that same mentality. They were public, but you didn’t get the sense that it was very financialized or running in a way that was super deferential to public markets in a way that other companies might be. Now, Atlassian is a very patient flywheel-based business model that the thing was just kind of printing cash by the time we got there and it’s just continuing to do so.

Scott Klein (46:37):

And so I think that they were able to run things their way because they had put in the 15 years of work to do so, and for people to be naysayers and get proven wrong again and again and again. It was a little bit different later on, in the sense that we were absorbed into a much larger operating product group. And so we got caught up in strategic planning and forces and trying to figure out, well, where are they going to invest?

Scott Klein (47:02):

All of a sudden, you go from thinking about just hiring for your private company to, “Hey, your operating group now has a pool of engineers that it is budgeted to hire and you will have to make your case for some amount of those,” et cetera. So in that regard, it did change a little bit. And I think too, there’s an emotional changing of the guard when you do sell your company that it’s not your baby anymore, it’s somebody else’s.

Scott Klein (47:24):

And to be honest, that changes relatively quickly, I mean, within the first couple months, I think it was pretty clear. Even though we were largely functioning exactly the same as when we were private, I think there’s something about the people that join a startup, especially one that was as small as ours. I mean, we were 15 people. They joined that because they want to be part of building something and feeling like you’re in that zero-to-one phase.

Scott Klein (47:46):

And when you get bought, I think a large part of that goes away, whether you want it to or not. I think that there’s just this sense that you’re swimming in a much bigger pond with much bigger fish now. And even though you might eventually grow to become one of those bigger fish, it’s not you against the world anymore. You’ve got a protector, you’ve got a financial supplier, in a way, even though we really didn’t need that. But yeah, it can be a much different feel.

Scott Klein (48:12):

I would still say that it is very useful in different ways. I think that there is something about startups that people don’t generally talk about, is that, especially when you’re small, there’s not a ton of career progression to be had. You don’t have “the adults in the room” to help guide and track and make sure that people have succession paths beyond what their current role is right now.

Scott Klein (48:34):

Even for Levels, we’re at 45 people or something like that, as of today. The people that are running head of product or head of engineering or head of business or whatever, we only have so much experience to go around to help people track through what would be a career path, where they can level their skills up. We will do a lot of that, and we’re going to do the best that we can. But I think for larger companies, what it does provide is, and we saw this, a lot of people on the Statuspage team took assignments on different products, or they tracked in a way that was different than we could have ever provided for them.

Scott Klein (49:03):

And so I don’t want to make the case that going from private to a publicly traded company, if you want to list on your own, or getting acquired, means that necessarily everything is bad, it’s just different. It’s better in some ways, it’s maybe worse in other ways. It just feels different in specific ways. But you know what? The Statuspage product got mentioned on earning calls, I used to watch the exec team go through the process.

Scott Klein (49:25):

I think that there’s actually more of a cultural thing about feeling like a big traded company than there is the actual mechanics of it. And you’ve got this whole division now that deals with the financial prep, and the machinery. And the reporting structure, all that stuff’s kind of the boring academic exercise that I think can sometimes swallow up the rest of the company in that culture of quarterly earnings. But I don’t think it has to be that way. And I think Atlassian was a good counter example of it not having to be that way.

Ben Grynol (49:48):

So out of all the phases, you’ve been through them all, what is your go-to? What’s your favorite phase?

Scott Klein (49:57):

I don’t know. I’ve become, I think, more agnostic and maybe almost Buddhist in an unattached way of, I just know there’s going to be pain and suffering in various regards based on the stage. And I’m just trying to more focus on detaching my sense of happiness from any goings-on at the company. What I will say too is that, we used to call ourselves a startup, but being at Levels has been a much, much, much different experience than Statuspage was.

Scott Klein (50:27):

I think each company, based on whether it’s B2B or B2C, how fast you’re growing, how small you’re growing, bootstrap, venture-funded, all of these dimensions add much different flavor to what you’re doing. And Levels, to me, feels much more like a startup in a way that Statuspage never did, because I think we’re just moving fast on so many fronts right now. And we’re hiring at a pace that, I don’t know that I had the recruiting ability or the wherewithal to just get rid of some of these areas of the business, that even as head of product, things feel more fast-paced and almost out of control than they ever did when I was CEO. And there was everything happening, it was happening under me, if that makes sense.

Scott Klein (51:10):

So, I will call out, I think when you are just getting started, there is this beautiful Goldilocks phase where you haven’t launched yet, you don’t have many customers yet. You’re building stuff in such a rapid fashion, there’s no technical debt. You basically got one or two people writing code, everything is happening with such little friction that it can feel like you are superhuman. It can feel like you are playing God in a way, resurrect, getting this thing to emerge out of the ocean that otherwise did not exist in a way.

Scott Klein (51:38):

So I just try to mix in all these Marvel metaphors, but there’s something so pure about that time of building the company, that I really look back on those days of, we had two co-founders, there’s my brother, and we had one other person who was handling the sales end of it. I long for the days when it was the three of us in this super overheated office in Mountain View, that we were just renting for the summer.

Scott Klein (52:03):

And I remember the music we were listening to. It just really felt like a special time to be creating something very new. The relationships between us were getting created at the same time. And so you cannot unlink those two things. But the Goldilocks phase of building something from scratch, and you’ve got zero to a few customers, there’s really something special, because you’re running so fast and there’s nothing to get in your way at that point. So, if I had to go do it again, that’s the phase I would get back to, because it’s very captivating.