SaaS Scaling Secrets
The SaaS Scaling Secrets podcast reveals the strategies and insights behind scaling B2B SaaS companies to new heights. Dan Balcauski, founder of Product Tranquility, leads conversations with successful SaaS CEOs, exploring their challenges, triumphs, and the secrets that propelled their businesses to the next level.
SaaS Scaling Secrets
The Hidden Mental Health Struggles of SaaS Scaling with John Peebles, CEO of Administrate
Dan Balcauski speaks with John Peebles, CEO of Administrate, about his journey from focusing on small to medium-sized businesses to transitioning towards serving large enterprises. He highlights the importance of making tough decisions, such as changing the entire team, and the difficulty of managing mental health as a leader. John also discusses the differences in managing technical versus non-technical teams, the importance of transparency, and innovative approaches to maintaining company culture and supporting employee wellbeing.
01:38 John Peebles' Journey with Administrate
02:30 Challenges in Scaling Administrate
04:03 Transition from SMB to Enterprise
13:31 Operationalizing the Transition
21:49 Strategic Transition and Culture Challenges
22:35 Building a Company Culture that Elevates Humans
25:38 Managing Technical vs. Non-Technical Teams
27:40 The Challenges of Scaling Startups in Europe
29:55 Mental Health and Leadership in Startups
36:32 Transparency and Confidence in Leadership
39:06 Rapid Fire Closeout Questions
Guest Links
I found it stressful. It's difficult to get going. Your feedback loop is measured in six months or a year, I was just sick of it. But I've often said this like kind of the first five, six years of the company's history. We're really just in search of one customer. It's like the only AI stuff that I trust is the code stuff, because you're actually executing it right then and there. I had a near total breakdown at a very, we're right in the middle of starting that transition to go to Enterprise. And, my personal life was a mess and the company was not going well and. had to raise money and we missed our numbers, and there was all this pressure and it was all those things together. You are not the exception. Just beware,
Dan Balcauski:you're not the special snowflake. Welcome to SaaS Scaling Secrets, the podcast that brings you the inside stories from the leaders of the best scale up. B2B SaaS companies. I'm your host, Dan Balcauski, founder of Product Tranquility. Today I'm excited to welcome John Peebles, CEO of administrate, a training management platform that helps enterprises manage complex instructor led training operations. John has built a business serving major enterprises like Siemens, Royal Caribbean, and Maersk. John, welcome to the show.
John Peebles:so much for having me.
Dan Balcauski:Well, excited to dive into the conversation with you. You have a lot of very cool, strong opinions which I think will be very entertaining and useful for our audience. Before we dive into your scaling journey with Administrate just give us the elevator pitch. What does Administrate do? Who do you serve?
John Peebles:Yeah, so Administrate is a training management system, is what we call it. It is designed to really help large enterprise organizations, multinationals that are doing lots of training in the classroom plan schedule. Automate the communications and identify issues with that. And so, if you, customer of ours is, like you mentioned Siemens, they're trying to train tens of thousands of people all around the world. They want that training to be consistent, done in the same way we help them with all the scheduling of that classroom training. So it's different from what a lot of us think in terms of an LMS or clicking next on a bunch of slides. It's the kind of nuts and bolts logistical challenge of training at scale.
Dan Balcauski:Well, administrates been around for over a decade now, and you've been CEO since 2012. Is it, looking back at the scaling journey what stands out to you as been the most challenging inflection point as you've grown? The company.
John Peebles:The most challenging, there's probably a list, 20 things along here. It's hard to prioritize. I'd say, I'd say with Administrate, it's been an unusual journey in a number of ways. The first was this. We didn't start with a clean sheet. The software began life as an internal tool within a company, and we all know how internal tools are built and or not built And and so taking an internal tool and getting it ready to go out to market was a challenge that, I'd say not a lot of startups tend to experience. We then had a number of years where we focused on serving the small to medium sized business market, and that is. A decent market, but there's high churn. There's a lot of small training companies out there that were our customers, but we just found that over time we could deliver a lot more value to large multinationals that were doing a lots of training at scale and just be much more valuable to them, and we could man a much higher value for ourselves. And so we made a transition from that SMB segment to serving these enterprises, and that was a very. Huge difficult challenge that we're just now coming to the end of that transition. It took a number of years and I think it's why I feel like I've been CEO of two different companies actually, because there's such different businesses and everything is just, the whole motion is different.
Dan Balcauski:Well that transition on the serving the SMBI, I'm, I want to dive into that. So what was it that you noticed going on in the business? I mean, you mentioned something like, high churn that may not come as much a surprise to people, but I guess were there other things where you noticed that was really sort of impacting the ability of the business to scale? Yeah.
John Peebles:Yeah, so there, there was so, so basically when I think about products, everybody talks about minimum viable product, right? And there's also this idea, I think. Where there's a minimum amount of complexity that is required to solve a problem, right? In our business and what we're trying to do, where you're trying to get basically large amounts of people into specific places in the world, whether that's a Zoom classroom where a classroom, or a hybrid and it's all timed and dated and people are moving around and resources, things that you need in order to train that class. And it could be things like. A simulator or a piece of equipment or whatever when you're trying to get all of this stuff lined up and do it at scale, there's just a minimum amount of complexity. And what we found was that it was the same amount of effort to get a customer up and running on our platform, doing those things, whether they were a large multinational, or whether they were two man band, SME, and, I think just the nature of the product and the problem that we're trying to solve meant that, if you're a two man. A person band that's trying to run training at scale and or trying to scale up a training business, that complexity can be overwhelming and it can be not worth the squeeze unless you're doing tens of thousands of students and so forth. And so there was just this real impedance mismatch between the problem that. We are trying to help people solve and the scale of that problem and then how much value you could get through that solution. I'm not sure if I worded that super well, but it's that concept of, you've just had to do a certain number of things for every class that you were run. And if you're only doing a dozen of them or so a month, it's just not a big enough problem that you're willing to do all that stuff for. And you'd rather just do it on a spreadsheet and ham and egg it.
Dan Balcauski:Well, there's a couple things you mentioned there. So one was the you're you moved slightly out of the world of bits and into that world of atoms. I used to be a head of product for a two-sided marketplace for as like an Uber for lawn care. And it's amazing, how complex those businesses get when you're having to add logistics into the mix because as, as good as you could make the software, there's still real world. People have to be able to show up on time and you have to deal with things like weather, and so it just makes things incredibly complicated. Then you also mentioned just this onboarding itself onto your platform and, and being able to make them successful. It didn't really matter if they were large enterprise or SB that was pretty much a, negligible difference between there. And I can imagine, the larger companies probably had a higher value and higher willings to pay for, to get to that point. I'm curious, so you, you notice this lack of a difference between what it takes to onboard a small company versus a large company. Take me back to that time. So you make this realization and, you hinted at the beginning that, you're still at the tail end of unwinding that. How what did you, would you have this realization like what happened next? Like how do you sort of make that decision of like, okay what do we do now that we realized this.
John Peebles:Yeah, so one of the interesting things about the administrate journey is we actually had some very early clues that. We were always destined to be this enterprise platform. Our, one of our first customers was a large training company that had 27 different locations all across the Middle East. And so that was a clue that, hey, there's a lot of, and they were willing to pay a lot of money there. Largest customer. I think that some of my own. baggage came into play because the previous company that I had been a founder of and co-founder of and CTO was large enterprise sales to healthcare, to hospitals, conservative organizations, long sales cycles, and I just remember. I found it stressful. It's difficult to get going. Your feedback loop is measured in six months or a year, I was just sick of it. And so when you, when I came into the Administrate situation, it was kinda like. This is cool. We can take orders over the internet and it was like really seductive, right? Because we put up a free trial page and I, it was like in a movie or something because within about two minutes of putting the free trial page up there, somebody signed up, right? And it was like, oh, cool, this is working. And then we were getting. But 10, 12 signups a day and all this stuff. And so it was like, wow, we can scale this and we don't have to worry about enterprise sales and this is great. But I've often said this like kind of the first five, six years of the company's history. We're really just in search of one customer. We didn't know it at the time, but with like the whole point of that five or six year period was basically to find one customer, and it was a company called ForgeRock, and they came on board as a post series, a startup. In the identity management space is single sign-on stuff. And there's a bunch of ex sun guys that went out and said, Hey, there's this open source software that Sun doesn't want anymore, and we think we can productize it and build a company around it. And they raise money and they just started growing like a rocket. And so they started as an SMB customer, right? Doing not very much training. And then they exploded. And we went with them all the way on their journey to when they went public and then were taken private, and then they merged with ping. And so now we're the backbone of all ping's training operations with a combined company name. But it was through that journey of this accidental customer essentially that. Became an enterprise right in front of us that we were like, wow, there's a ton of value here that we are driving for them and they are willing to pay for this value and we should go find some more customers that look like them.
Dan Balcauski:So what so you you started that saying a forge rock. Was this like the customer you didn't know you wanted? But I guess so, so what was it as you grew with them that you realized that like these were the folks you were waiting for. What did they teach you in that experience?
John Peebles:Yeah, so I think another difficult thing about selling to SMBs, and I think it's just getting more and more difficult, is an SMB customer, like let's say you or I, or buying something for a hobby or for home or whatever, we are used to a high quality. Right. My iPhone is a high quality product. The things that I use often do one thing and one thing very well. I'm talking about things like Dropbox and iCloud and Spotify or Apple Music or whatever. These are polished products that do one thing very well it's focused, and when. You're selling essentially a platform that is an ERP or an Enter enterprise resource planning platform, which is effectively what we are, a verticalized ERP. We have to do a lot of things and we have to do a lot of things pretty well, but. customers are grading you against the Spotify or the
Dan Balcauski:Mm-hmm.
John Peebles:kind of alternative products that they use in their lives. And these platform products are difficult to get right. They're diff, they're hard to design. They are. There's a lot of modeling that goes into place and as you're, when you're still early on your journey, our product was not perfect, and we already talked about how it was an internal tool, so it was very far from perfect. We didn't have the best starting spot, and so I think that just what we learned with ForgeRock was that. They didn't care about the rough edges of the product, right? Because they were at a scale where they cared a lot more about solving their fundamental problem, which was how do we get these thousands and thousands of students through this training in a very high quality way? And they couldn't build out a training team to take care of all that. They just needed to do with about three or four people and. For them. The rough edges that we had, particularly at the time, were less important than the mission that they had. Being an open source software company training was exceptionally important for revenue generation for them as well. Right. So, in millions of dollars of revenue that depended on this eventually. It was very key when they transitioned to to, to being less of an open source software company and more closed source. And that was just a really interesting realization. It's like. These details or these kind of nitpicky things go by the wayside very quickly when you're having to worry about tens of thousands of things versus 10 things,
Dan Balcauski:So there was a, it sounds like there's certainly a need driven by their growth and then the limitations of their team and the, and the, with the training needs that they had to look beyond the, the rough edges. And then there was, there was a real fit for the value that you could provide and they were willing to look past sort of the rough edges. And that's I love that. I love that example. I'm curious, like, so, so now you're in this space and you realize that. You're like, okay, these guys are really a fit. These s and b customers are, are taking, a lot of time. Like do you organize, like does this become an explicit mandate within the organization of we're not going to. We're gonna take away a free trial. We're going to change our, our go to market. If somebody, you're like, we're gonna do hard qualification upfront to figure out sort of, the scope of the organization and say no to revenue, like, how do you sort of take this learning that you learn from forge, rock and this other generalized pattern that you mentioned in order to really make this transition?'cause I think it's, it can often, it's one thing to sort of say it and then another thing to live it where you're like, well, these people are. They're willing to give us money. So we could take that.'cause that'd be nice.'cause it's revenue's, revenue. I like How did you like organizationally operationalize this these learnings?
John Peebles:Yeah, I mean, it's given me PTSD almost just thinking back on it.
Dan Balcauski:Sorry, that wasn't the intent.
John Peebles:so, and the, here's the thing. It's so. It's so seductive, this idea that you can do both at the same time. Right. Thankfully I avoided that trap. We avoided that trap. We knew that we could not do SMB and Enterprise together. Right? I think maybe if you've got 15,000 employees and you know all the stuff, you're a huge organization. Maybe you can try to do that. But for a startup you gotta pick one. and we we just realized that we had picked the wrong one. So that was not a, that was not a great realization to make. And to our credit, like we went to Saster and read all the blogs and went to the conferences and talked to other founders and so forth, and everybody says, and said. At the time and we listened, which was, you're gonna have to change out your entire team because the people that you have that are comfortable in the SMB motion that understand it, that are familiar with the ways of working. They're just incompatible with the enterprise motion and the ways of working. We read all that. We thought, we listened to it, but we really didn't. And I thought we could be special and we could be this unicorn. And I really believed in our team at the time and they're great for a whole bunch of reasons, people just have their comfort zone and the way that, that they naturally operate. And what we found was we just hung on too long to that notion that our team, that was great at s and b could get us to the enterprise. and land. And and that's a big regret because I think we should have, so, so we did the right thing, which is we. We took down the free trial and we burned the ships. Like we deleted all of our website pretty much. And'cause it was all like s and b focused content. And we even did things like, we're headquartered here in Scotland and a bunch of our team, particularly the go to market stuff, is in the US'cause that's our biggest market. But we even did things like, we changed our spelling from British spelling to American spelling and all this stuff. But that, that idea, it, it reminds me, it's one of my. Favorite essays of all time, where guy just basically says, you can't tell people anything. Right. It's like the fundamental axiom of this essay. And that's, it's a painful thing for me to agree with as the CEO of a learning platform effectively, but like people just. People just have a hard time learning, right. Until they've gone through and made the mistake. And I no exception to that, right? I read all the literature, I thought I listened, I thought, and I just, now I'm a, I'm a special snowflake and we'll do it differently. And, and we were wrong, and that probably cost us a couple years, if not more in, in that journey and made it much more difficult.
Dan Balcauski:So I'm curious,'cause you said so you, you, Ruth free trial, you, you changed the content of the website to be, to remove the s and b flavor. But you mentioned also that the people who, you thought you had good people. I was this mostly on the sales side, where the sales team that is good at closing SMB business doesn't, didn't translate to enterprise. Is that mostly where that friction landed?
John Peebles:No, it was every piece of the business. And so if you think about it. Our marketing, folks that, that understand how to market to a credit card. Swiper, free trialer, are not the people that are gonna be comfortable necessarily talking to a C-level chief learning officer at Siemens, right? Or, who's their now new target. The salespeople would not be comfortable talking at that level, so you go from taking orders basically on the phone and doing a quick. 30, 40 minute demo and, do you wanna sign up? It's a hundred bucks a month. That's a much different motion than the long enterprise sales cycle where you're having to develop relationships with VP and C-level folks. Same with support. The much more transactional kind of take it or leave it, or here's a doc, link to, to answer your ticket or go do it yourself or whatever. just doesn't fly when people are paying you$150,000 a year or whatever for the software. And,
Dan Balcauski:Hmm.
John Peebles:then you need the kind of implementation and executive support and customer success and all that. So all of that had to get changed to just fit the new market and the new strategy. And it was just, it's a bit overwhelming even to think back on how much everything had to change. But it was certainly overwhelming at the time.
Dan Balcauski:Well, I'm curious, like looking back and looking at that transition is there anything that you would do differently or, or advice to other folks who were looking at that transition of, of what to do? First.
John Peebles:Yeah it's hard, right? So again, we thought we were going in with our eyes wide open on what it was gonna take. And I think of the, one of the saving graces, I guess. That we at least did, right? Is both myself and our COO had a background in that type of sale, right? That enterprise approach. And so, we at least knew what, where we needed to go. I think that can be difficult though for a lot of founders. But I would say, I had a, there was almost a replay of this where five, six years ago. I got asked to help out on the board of a small early stage startup here in Burgh, They were selling a very cool medical device to, to hospitals that it would strap on your arm and replace all of the instrumentation that you'd typically get in ICU. And it's gonna be, it's now FDA regulated and approved. And so it, it beats the gold standard of all those expensive machines. And that's nice, but it's also means the patient could be much more mobile. And also it means that the system could alert nurses or doctors in the ward that a patient was degrading because they didn't have to come around and actually look at the. Instruments in
Dan Balcauski:Mm mm.
John Peebles:room. So you could do all kinds of things like get patients home faster, but you can monitor them remotely or have less people in the actual ICU, but it's still in the hospital and all these cool things. Well, the founder, like many founders, we say, well we wanna put this up on the website and swipe a credit card and maybe you buy one for your grandmother or whatever. And I was like, just stop. Don't do this. Right? Like, we need to target hospitals and it's gonna be a long sales cycle and we need to put the price way up, and it's gonna be six figure minimum to get going. And I, there's, and I even said, we're not even deal with Europe, right? We're gonna focus on the US only. That's my advice. Right. And I think that was one of the very few things that I can take credit for with that company's eventual success. And they were. success story. Sold for north of four$50 million to Best Buy five years later. Saved a lot of lives in the process, but the, and I had a front row seat to watch. One of the most incredible CEOs I've ever had the opportunity to meet. Operate, and he is in his late twenties, but the one thing I feel like I can take credit for on that is just that kind of nagging him and saying, no, we've gotta go up market and we gotta target enterprises and we
Dan Balcauski:Hmm.
John Peebles:know, it's hospitals and large organizations, and don't worry about this s and b stuff, and he fought me on it a little bit for a few months and was like, yeah I think you're right. And that was a, I think, a key moment for that company. And so a long-winded way of answering your question, which is if you can find somebody that's either had to do that before or just understands what's involved as a founder, do it because that'll be so valuable.
Dan Balcauski:Yeah. Well, there, so that's a really interesting strategic transition. Transition. I think another area where maybe conventional wisdom often falls short is around building culture at scale. So I'm curious as you scaled, administrate, and, and maybe this also pertains to your scaling at other companies. What have you found to be the biggest culture challenges that emerge as teams grow? I know you're you have a, a strong international background. You've got, a lot of your business in the US you're based in, in Europe. So I dunno if it's for you it's been culture across regions or culture at different stages of growth. What what have you found that most people get wrong when they think about culture?
John Peebles:Yeah it's a big topic, right?'cause it's so important. I think
Dan Balcauski:It's also very amorphous. It's a, it's one of these things of like culture's important. You're like, great, what do I do now?
John Peebles:Totally. And we even talk about this at administrate, we say we don't like using the word company culture because it becomes confusing when you're like us and you've got all these different cultures within the company that are all colliding in various different ways. We like to think about it in terms of we have this. We have this conceit, this dream. Really I have this dream which is, they tell you to buy the best mattress that you can buy, right. That, that you can afford because you're gonna spend a third of your life on it. Right? But the same thing applies to work, right? We spend a third of our life at work or more and it's a huge part of people's identities and their day-to-day interactions and so forth. And I have this dream of kind of a company that people just love to work at and they can be really successful at. And they. talk about, we used to call this this dream, the ultimate human organization at administrate. And our British team would roll our eyes and be like, that is so American. And like, well, yeah, maybe it is, but, but we've refined it a little bit to, to be more of a statement of just elevate humans, right? And not, that's not just our team, but that's also our customers and their customers. And we want to just be an elevator for humans in a whole bunch of different ways. And so for us, when we think about company culture, it's like, are we. Building an environment that is elevating the humans that exist within it. And that can sometimes be uncomfortable, right? And it's not everybody being nice to each other and all this stuff necessarily, but it's I mean, we don't need to be jerks, but like, it's more about what are we doing to elevate ourselves and our customers and our investors and our communities and all this type of thing. And so when we talk about the company culture and administrate. We specifically don't have our values. As a company written up on our walls in our office back when we had an office, and we didn't have any of that. Those posters that you sometimes see, and I'm not criticizing folks if they do that, but the idea was we want it to be where if we had a journalist or a visitor or observer come in to the company and hang out with us for a couple of weeks, that they might be able to write down what they think our values are by observing how we work. And so that's really the barometer because we do this onboarding and it's a talk that I give to every new hire at Administrate. And I just say, think of the worst companies in the world, right? And people always, I think Monsanto comes up a lot and, of people. We'll talk about their broadband provider, like Comcast, or some of the worst companies ever. And I'm like, if we go to their website right now, they'll have values that are probably pretty close to ours, in terms of like, oh, we want to do these nice things or whatever, but they're not living them, and so,
Dan Balcauski:Yeah.
John Peebles:That's. I think for us the real test, and we don't get this right and we fail all the time. But I think just having that stated goal has helped us get through some rough times and it's been a mirror to myself and to, to others within the organization at times that we need to do better. And so that's, that's how we think about it.
Dan Balcauski:Well, I'm curious'cause you come from a technical background, if I'm not mistaken. As you mentioned you were CTO at a previous company. Do you see a difference between a technical culture and overall company culture? I.
John Peebles:yes and no, but I think there's definitely a difference in managing technical folks versus non-technical folks. I used to think I was the world's greatest manager of people, and it turned out that. just me and a bunch of techies, and we'd hired predominantly from the Midwest at the time. This is like, 15, 20 years ago. So it was all pretty culturally similar backgrounds and all this stuff. And it just turned out, I'm not a great people manager and I had to learn that. Think for us, the, real similarities are just like, we want, we wanna find smart people that get things done, and. Do the work in the right way, and I think that applies whether it's technical work or non-technical work. I find it a little bit easier sometimes to measure and manage the technical work, though it's a little bit easier to ize sometimes.
Dan Balcauski:the code work is a pretty good metric, right? I think that's why all the AI companies are focusing on coding.'cause it's, it's like, is this legal brief gonna help me win? This case is hard to test. But, does this code run and pass its unit tests? Is a little bit more measurable.
John Peebles:Yeah, I was literally just saying that to somebody the other day. It's like the only AI stuff that I trust is the code stuff, because you're actually executing it right then and there.
Dan Balcauski:Yeah, it's well, i'm, I'm curious because the I, I think in our, our previous conversation, you were mentioning that one of the big challenges, you just mentioned like, hey, like, can people do the job, do things the right way? But that we have a significant. Dearth of really senior folks who know what the right way is. So I'm curious if, as you think about, the, the technical either both could be the hiring or just the culture. Like is that an additional challenge on that side that maybe is not reflected in the broader sort of company culture practices?
John Peebles:Yeah, so I think. So I've got this opinion, and it might be somewhat controversial, but startups are hard, right? And there's all the stats about how often they fail and all that stuff. And I think that building a startup in Europe or outside the US is particularly hard. And the reason for that is the US is probably on its fourth or fifth generation of folks. That have been going through and building startup tech companies. If you go out to the valley, there have been people that have been doing this, they've retired, but they started in the sixties and seventies and, that's quite a, a number of generations. And out here in Europe, we're only really on, depending on what country you're in we're in our first or second generation. And that means that there is a, a lack of folks that have. Either done this before or done it at the scale that, you might want to be trying to approach. And so here in Scotland there are very few founders or folks that have done this before and had an exit because it's just wasn't a thing till about 10 years ago to do a tech startup. And so that's one of the key pieces of advice that I. To hammer home. We made this mistake over and over again at Administrate, which is, I just fundamentally believed we could, we could get people there or people could grow and change and, whatever. And. problem is, is that when you're scaling quickly and rapidly, that the learning curve is just too steep. It's just too much to take in. And going from$5 million in a RR to$20 million in a RR is such a big jump and everything needs to change. And if you're not relying on a playbook and past experience, and it's not like you've had to have done all the job before, but you have to at least seen it done. Alongside or whatever, been a part of a company. and that's actually some of the advice that I tend to give young founders is I say, look don't start a company right outta college or whatever necessarily. It's probably a good idea to go work at a startup for a year or two and see some of the stuff and watch the mistakes that are being made by other people on their dime, and then you'll be better prepared. So it, these are things that are hard to hear sometimes though, when you got your next greatest idea.
Dan Balcauski:Yeah, exactly. Exactly. Well, I, I wanna go back to at the beginning you were talking about, sorry, I didn't mean to prompt you into PTSD, but, it, it does bring up this whole idea of. Of, mental health.'cause you mentioned this, this perfect storm where, you're going through this this transition. Beyond the strategic challenges, I'm curious about the psychological toll of going through something like that as a leader. I think there's this mythology around founder resilience that great leaders need to grind through everything, that showing vulnerability as weakness. Mental health is a personal issue rather than business one. I guess based on your experience going through that period what do those myths get wrong?
John Peebles:Yeah, I, I'm not an expert on mental health and I don't consider myself to be an authority, but I do have a lot of experience in startups and I have. Come to the conclusion, the realization that these companies, building these companies is a fundamentally very difficult thing. And it's difficult for every person involved in the journey, right? From CEO, all the way down or from whatever, all the way up. And that doesn't seem like a controversial statement. And I don't think anybody would disagree with that. People are like, yeah, startups are hard. And even the best ones the top outliers that we all read about and whatever, they would say that it was very difficult. But what I think is strange is that our reaction defaults and my reaction always default, defaulted to Yeah, but we have to act and we have to be. at every step of the way.'cause this is a confidence game.'Cause investors want to see confidence and your team wants to see you confident and your customers are placing trust in you and they want you to be confident. So there it's like, we know this is hard and yet the default requirement or approach is that we can't act like it's hard and we have to just put up this facade and everything's great and it's water off a duck's back. And I've just, found, I don't think that's super helpful. I think that that causes a lot of problems because inevitably every startup is gonna go through a period where things are not going well. And every CEO and founder I've ever talked to, and this includes. Guys like the CEO of Zoom, which has gotta be one of the most fairytale, rides that has ever existed. CEO of Skyscanner here in Edinburgh, huge, huge success story. I've. know, talk to these guys. And I've just been like, did you ever have these like w moments where it's like, we're fucked. It's over. And they're like, oh yeah, we had two last week. And it's like, it's and it is normal. And the problem is that I don't think. A lot of us realize just how normal it is, or we don't believe that it's normal or whatever, and then that makes you feel even more isolated. And so really for me, one of the best things that ever happened is I had a near total breakdown at a very, we're right in the middle of starting that transition to go to Enterprise. And, my personal life was a mess and the company was not going well and. had to raise money and we missed our numbers, and there was all this pressure and it was all those things together. And, and I just thought, man, I need to get some, need to get some help here. I we presented to investors and I almost, getting this really bad pinch in my neck. And thankfully we finished the meeting and I was walking home and I just collapsed in the stairwell in my flat. and I thought, thought I was gonna die, basically. It was just like, am I having an heart attack or what? And it was that, that really home that something's gotta change here. And I needed some help. And so, I had started talking to a therapist and I was surprised at how quickly that made a difference in a positive way. And then it was well. That's weird because I actually had to get my assistant to, schedule that.'cause I knew I wasn't gonna do it. And there's so much inertia, I had to go find the room and it was, I was embarrassed to show up there and I didn't want anybody to see, and all this stuff, all these natural feelings. And so we just thought about it like that was really helpful for me and. We're about 60 people right now. That means somebody's life is usually going through something at that scale and so we thought, well, why not extend this to our team? And so for the last. eight, nine years, we've had a therapist as part of our team.
Dan Balcauski:Oh wow.
John Peebles:our folks can make appointments with her. They're all completely anonymous. You can do'em over zoom, you can do'em in person. And we just get the bill at the end of the month. And then during COID there's a lot of stuff going on and people are really struggling and afraid. And we were under a really intense lockdown here in Scotland. And people in Europe have much smaller apartments than they do in the States. And so, we then made the decision that, hey, anyone in our, anybody on our team can give a session. Of therapy to anybody, right? So, if you see somebody struggling, it's a friend or a, whatever, just say, Hey, we've got this resource, and would you like to try it out? And it's just been one of the better things we've done, and I think it's really been an interesting thing and I've been really pleased because there's been a number of other startups in Edinburgh that have also followed in doing the same thing. It's something that we try to talk about and be very open about, and, and I think it helps to just face up to that issue.
Dan Balcauski:Yeah. That's amazing. I have not heard of a company doing that. So that's a, that's an amazing resource. I'm curious, like,'cause you did mention, it is this confidence game, and whether that's, the, the CEO with the board or the CEO with the employees or future investors I'm curious how like, having a therapist. Is a strong move and that's obviously a really good tactic or support structure. I'm curious if, you view your ability to sort of play that confidence game any differently, right? Is there, are there ways that you are able or like have grown to be able to show vulnerability as a strength? So that you don't have to carry that. Right. Because I imagine, right. Oftentimes, like, board meetings are, are one of those things where like, a lot of people are just like, I hope I get through without like, them like jumping down my throat. But at the same time, like you do have a, a team there that isn't invested in seeing the company successful. And so you want to like, ask for their help. I guess, like how do you view, maybe it's with the board or maybe it's with employees, like how do you view playing that confidence game differently through this lens?
John Peebles:Yeah, it's a great question. I think that the default is. And I've been involved in situations like this, right, where you're raising money and you got these projections and sometimes people believe them and sometimes people don't or whatever. And I think the wrong way to go about it is to just. Kinda be confident for, for no reason or whatever. And so I'm not just a big fan of like showing, showing your work, I was like, I sucked at math in in high school and college, even though I got a computer science degree. So that just made it even more difficult. But I became the master of partial credit, by, by showing all my work. And I think that is probably the way that. We've survived as a company, with our investors and board and our stakeholders and customers because the board knows when it's not going well and customers know when you're struggling and, and whatever. And so the idea, transparency is a core value of ours. And I For me, it I've evolved to be much more intentional about. Showing the reasons why we believe the things that we're saying. And so, we went, we went through a year where we had almost no sales a couple years ago. It was, the pandemic was really tough. People weren't spending large sums of money. They're not gonna let$150,000 out the door to buy software. They'll just continue struggling, and that. Most CEOs, leadership teams don't survive a year of very little sales. But because we just really worked on, here's our hypothesis, here's the work that we're doing and we're really intentional about that. I think we've managed to build trust and. I still believe, like, I could get fired at any point for any reason. That's just the name of the game. But I think that's just so important. And that'd be my biggest piece of advice is yeah, like, people know when it's not going well. And the last thing anybody wants is bloviating and all this kind of false confidence stuff put in the work show, the work people might actually surprise you and give you good feedback. Actually when it's gone really badly and we've had to. Have tough conversations with stakeholders and investors and so forth. A lot of times they've flipped into be very encouraging, when they see how we've thought about the problem and what we're doing about it. So that's been interesting for me.
Dan Balcauski:Transparency and be a king of partial credit. I love that. That's a good, that's a good little nugget. Well, John, I can talk to you all day but I do wanna be respectful of your, the audience's time. Thought of wrapping up with a couple of rapid fire closeout questions. You ready?
John Peebles:Yep.
Dan Balcauski:What's something you believe that most people disagree with?
John Peebles:Oh man. I think that for software engineering, either have it or you don't. There's no training it and that, that hurts me to say out loud, but I truly believe that. I think you just, you're either bored with it or you don't.
Dan Balcauski:As a, as an ex software engineer with a computer engineering undergrad. I, I, I, I resonate empathize and maybe a little triggered by that statement, but I can't disagree with it. When you think about all the spectacular people you've had a chance to work with, is anyone that just pops to mind has had a disproportionate effect on the way that you think about building companies now?
John Peebles:Yeah, so actually there's, I never worked with this guy, but he wrote a book called Conscious Capitalism. It's the founder of whole Foods and I thought it was an incredible book, really influenced. Way of thinking about what is capitalism? What is really capitalism? Why is it good? Why is it just why when we complain about the capitalism run amuck is that's not really true capitalism. So that really influenced me. I've been really blessed to work for. Just over a decade now with one of my best friends. He's our COO here at Administrate, really influenced my thinking and I think fills in a lot of gaps for me and me for him. So, working with your friends is not always easy. He is the best man in my wedding, but it's, it's it can be really rewarding when you do it well.
Dan Balcauski:Well, very cool. Very cool. If I had to give you a billboard, you could put any advice on there for other B2B sassy, trying to scale their companies, what would it say?
John Peebles:You are not the exception. Just beware,
Dan Balcauski:you're not the special snowflake. Got it.
John Peebles:these things in general will apply to you.
Dan Balcauski:That's awesome. John, if our listeners wanna connect with you and learn more about administrate, how can they do that?
John Peebles:Yeah. Or you hit our website, get administrate.com, or I run a very infrequently updated personal blog@pebs.org, so happy to always check in with folks out there.
Dan Balcauski:I will put those links in the show notes for listeners. Thank you John. That wraps up this episode of Sask Gay League. Seeks. Thank you to John for sharing his journey and insights. For our listeners who found John's insights valuable, please leave a review and share this episode with the network. It really helps podcast grow. Thank you network. It really helps podcast grow. Thank.
