#75: Jeff Shiner, CEO of 1Password — Earning the right to lead, how to thrive while bootstrapping...

Welcome back. This is From Startup to Grownup. My name is Alisa Cohn, and today I'm thrilled to welcome Jeff Scheiner to the podcast. He actually goes by Scheiner, and Scheiner is the CEO of 1Password. 1Password is a leader in human-centric security and privacy and comes with everything you need to protect, fill, and securely share your passwords, credit cards, and other private information. Since joining in 2012, Scheiner has grown the company from 20 people to a 1,200-employee global organization with a $6.8 billion valuation. Shiner and I covered a lot of ground, starting with the fact that he came on board as a CEO, but the founders didn't tell anyone for about 6 months. He had to kind of earn the right to lead, and we discussed exactly how he approached that and what he learned. We discussed how important it was for him to make sure he was fully aligned with the mission of the company before he joined. What he did in his early days, like step by step, and the traits he looks for now when he hires new senior executives. We also talked about fundraising. 1Password is a bit unique in that it was founded in 2005. Shiner came on in 2012, and they didn't take any funding until 2019. We discussed that decision to bootstrap for so long and also the decision to finally take on venture funding and how he vetted the investors, including Ryan Reynolds. And other celebrity investors. We also covered Shiner's top leadership practices that he's used to scale the company from 20 to 1,200 employees. Lots of practical tips here, so please enjoy my fantastic conversation with Jeff Shiner, the CEO of 1Password. Jeff Shiner, Shiner, welcome to the show. It's so great to have you.

It's great to be here.

I'm so excited to talk to you today about 1Password and about your journey. First of all, tell us about 1Password, what the founding insight was and how you got involved.

Yeah, so the founding insight was actually a really interesting one. So it's got two founding families, Dave and Sarah Roustom and Natalia. And way back 19 years ago, which is when it started, Dave and Roustom were actually building websites and that was their job. They were struggling a little bit to build them inexpensively enough and were sometimes getting underbid by others. And so they thought, well, what do these e-commerce websites need? They need people to be able to log into them. They need to be able to, you know, pay and stuff like that. So they actually started 1Password and it's a little bit of lore, 1Password lore, but it was true. And it was like, it was going to be a 30-day project. So 1Password was going to be a 30-day project where they were going to, you know, be able to build this app that would allow them to use test data and fill in and, and, and build their sites cheaper. And as soon as they started doing this, they started realizing, well, wow, this would actually be useful for themselves. But of course, you know, to do it with themselves, they would need to actually do it securely. So they added the, you know, the cryptography to it and, and then they put it up on, uh, like shareware sites and things like that. And people started to buy it. And, um, you know, again, it, it, it really started off as solving a business need for them, and then very quickly turned into, wow, this is something that other people see value in. And then from there, it just, you know, it just blew up.

Right. And so, what they needed, just to clarify, like, they were like, oh, we can use one password, or we could somehow encrypt our passwords, or what? Like, what specifically was their business need that everyone then decided, oh, we need this too?

Yeah, well, the very, very first need again was, you know, on these e-commerce sites that they were building, they needed something that was going to, instead of having them type in all of the data every time they needed to test a website, could they, you know, could they build a tool that would fill all of this data in for them, right? So whether it's login information, credit cards, addresses, it was really about filling that out for them. But then they started to realize, well, geez, in our own lives, in their lives, they could use the exact same thing as they went about the web and started to shop. And the only difference there was between the test data and real data, of course, was the need to make it secure. So, they added the security, then all of a sudden, you know, now they could start, you know, surfing the web and shopping online and doing things like that in a much more convenient way. And then it started to turn into, wow, we can actually do it in a more secure way as well. And that's what got them excited to put that out there for others to to start to use as well.

Amazing. And I love how you call it lore. I love company stories and company lore. But what's interesting is the lore doesn't include you. So how did you get involved?

Yeah, so that, you know, that, like I said, was what, 19 years ago. And, you know, over the years between sort of 2006, which is when myPassport itself came out, and then 2012, which is when I joined, it was still very much a consumer app. In fact, mostly an Apple, an Apple app for the Mac and for iOS. And the company started growing. And, you know, they hired their, you know, their first employee, which was a big change. And Dave wrote about this on his blog post, about how scared I was to have an employee. And then, you know, eventually got up to roughly 20 people. And, you know, Dave and Rustem want to build and innovate. They didn't want to lead a company. And, you know, Dave and I actually knew each other for many years because I was his you know, boss back at IBM in the late '90s. And then he and Sarah lived up the street from Brenda and I, and then so we became family friends and things like that. I had gone my own way after IBM and was doing consulting in the US, and I had moved from sort of the architect role into a business leader role. And so, you know, that's why he reached out to me because I could still help. I mean, when you're 20 people, you do everything. I was building the app, but at the same time had some of the business, you know, skills and interests that they wanted in, in growing a company. And so, uh, he reached out to me, I think it was like right around the end of 2011. And, and, um, but 6 months later I, I joined the company as their, as their CEO.

But I understand that they didn't tell everybody that you were the CEO.

That's right. So for the first like 6 months, um, you know, they, they didn't tell everyone that, didn't tell anyone that I was CEO.

Anyone.

They, Yeah. Yeah. They, they knew, you know, the folks know that, knew that I had come in to help them lead and so on and so forth. But, you know, when you're a small company like that, even though Dave and I had known each other for many years, it was, was I gonna be a fit, right? Was I going to, uh, lead the company astray? Was I gonna turn a super corporate or, or things like that, that, that, you know, that Dave and, and, and team didn't want. And so they, they, they just said, you know, and I certainly agreed to it, like, hey, like they brought me in and the paper said the CEO, but it's like, let's not tell anyone. Like, What's the, what's the need? And, and it goes back to something that I learned many years earlier in, in, in my life, and that was a leader leads. So you're, you either lead or you don't, and then people will respect the way you, you, you lead or they won't. And, and, you know, and, um, so 6 months later we were, I think we were in, um, uh, somewhere in the Caribbean at our, at our like year beginning meeting, which we, we used to, to do in person back then. And that's when, you know, we said to everyone like, hey, here's the, You know, here, here's why we brought Jeff in. And you know, by then everybody knew me and, and, um, obviously I, I fit in, so I became the official CEO. Not that I would like to think that that doesn't change much, right? Like, I would like to think that the, the title is maybe an outward reflection that that's necessary, but inwards, hopefully people are, are leading you because you're, you know, you're helping go in the right direction as opposed to just cuz you've gotten some you know, an acronym behind your name.

Well, I, I, I love that and I agree with that, but actually that's not necessarily the case in, in many cases. So I'm curious, you know, when, when he said to you and they said to you, listen, we wanna bring you on as CEO, but we're not gonna tell anyone. I guess I would just ask like, what was your first reaction to that? And then what specifically did you do for that 6-month period to gain credibility?

So, I mean, the reaction to that was that made sense to me because it can be very disruptive to a company to come in and first of all, and just say, here's the CEO, and then have everybody look at you and say, okay, like lead, right? Like, you know, and it's not that way, right? We've got the, we call ourselves the gang of 5, right? Dave, Sarah, Mr. Murtaza, Natalia, and I, and that's how we led. And first of all, when you're 20 people, what does leading mean? It means doing. Right? It means lead by example. And so, uh, it wasn't much longer after I started, you know, I was in, uh, in Rustam's house. I can't remember what we were building. I think it was the iOS app or the Mac app. It was one of those two and stuff like that. And it was just building, but at the same time, it was being part of decision-making and things like that as a group of 5. But the one thing I do remember saying to Dave and Rustam when we were chatting ahead of time was, I'm going to double the size of the company. And that was sort of the big— one of the bigger changes. So, yeah, as part of what I did, as I, you know, as I came on, was to hire and to start to grow the size of the company, in part because that's, you know, that's why they brought me on, is they were at that point of the growth of the company where it's like it's getting a little bit too big to just treat growth in an ad hoc manner. And if we were gonna continue, we would need to grow the size of the company or we would need to explicitly, you know, keep it small and shrink it. The decision was to grow. And so that was the other side of what I did was really look at hiring, you know, additional folks. But really at that point, you know, I don't care what you call yourselves. Like you just have to be part of the team. You know, I remember when we were 20 people, we could get together in a circle and, and we could discuss what we were doing. And as we grew, I maybe 40 people, 50 people, we tried to get everybody in a room and we couldn't fit in a circle. So we, we all sat around the edges and we called it a squircle 'cause it was a square circle. You know, like it's just, part of it is just continuing to, to keep that company growing, but growing in a way that, that's meaningful and helpful as opposed to just growing for the sake of size.

Yeah. Well, there's a lot to unpack there. I mean, I appreciate that you came on and it sounds like you were, you, it was clear to you that the best way to, to lead whatever they called you, right? But the best way to kind of win with this group was to sort of organically fit in with the co-founders, with the gang of 5, and to make sure that that relationship was working and that you all were kind of simpatico and aligned on decisions. Is that fair to say?

Yeah. Again, it's that combination of, of do you fit in the culture? Like whenever you bring on a leader, uh, I get that companies say, hey, we have a culture and we bring people on into that culture. And that's true to a certain extent, but the reality is your culture is the combination of the people at the company, you know, and there's an outsized impact on culture from the senior people, from, you know, from those who are leaders. And so when they were going to bring me on again, it's like, what impact was I going to have on the culture? Was it going to be positive? Was it going to be negative? And then the second side is just to show like the folks at the company that you're actually adding value. And there's many ways to do that, whether that's, you know, in terms of organization, in terms of communication, in terms of, in this case, just like, hey, we're here to build a product, help build the product, right? And make sure it's the right product to build, especially, especially early on, you can have a more direct impact in terms of being part of the design and development and customer support and everything else of the company than, you know, you can perhaps even now at 1,200 people.

Yeah, that's, yeah, that's so, so true. So you came on and really you came on and, and I mean, I'm assuming that everybody assumed it was like you were coming on in context of being another co-founder really. I mean, that was kind of probably the vibe in a way, or you were kind of an important leader inside of this co-founding team, And I'm just wondering, first of all, what kinds of conversations did you have? I knew that, you know, these guys, I, I know that you knew these guys anyway, but like, what kinds of conversations did you have in advance to make sure that this was gonna fuse together?

Yeah, it was, it was really about what are we trying to accomplish, right? From a company point of view. So I'll be honest, the first thing I wanted to do was make sure that, that I understood where where we were going. Like, because if, you know, are we trying to grow the company? Are we trying to, you know, shrink the company? Are we, you know, trying to stay in a niche? Like, if I look at something like One Passer, there's so much immediate obvious value in it, but are we trying to, you know, help the world stay safe? Or, you know, is this just about how do we get to X size and sell? Like, what's the company's goals? Because I'm, you know, I want to build something. I don't want to, you know, build it for 2 years and then just say like the goal is in 2 years to sell or whatever the magic is. So that was the most important one to me is what are they trying to accomplish? You know, like I said, I've known Dave and Sarah, they're the most down-to-earth human beings you'll ever meet. Sarah's, you know, Sarah's an absolute joy and we're not allowed a single all-hands call where Sarah, she must swear. The company demands that she swears. And she swears when she's happy. So it's like at the end of the meeting, if she hasn't, you know, hasn't sworn once, then there's concern. Like it's just that sort of, you know, I know people take the word family and overuse it sometimes at companies, but it is that family vibe. I didn't know Rustam and Natalia, so to me it was important to get to know them as people. And again, absolutely wonderful people. As we grew, you know, and started to, eventually need titles and stuff like that. I remember, you know, saying that, that, um, Dave and Rustem, who were the two at the time that, that they were the most active, like Dave was, um, you know, the heart and soul and Rustem was the brain and vision and Sarah was the minister of magic. And it was like, you know, it was those sorts of, of, of roles. And I think that shows, uh, you know, uh, really where, where they were focused. And so it was about getting to understand first and foremost, what did, what is the goal of the company? Then two, what role did they want me to play? And I don't mean by title, but I mean by, you know, change and, and, and impact did they want me to have?

Right. That's, yeah, I think it's so important to have those conversations. And then you, it sounds like you were very focused on understanding that the company needed to grow, like literally grow in terms of people in order to achieve that vision. And I guess I'm just curious, what did you learn during that initial growth period, but then also during your you know, you're now much bigger growth period. What have you learned about hiring and specifically what have you learned about hiring senior people?

Yeah, I think the most important thing for me, especially when I, when I look at hiring senior people, is what I call attitude and aptitude. You know, I like to say, and I think it's true, like everybody I hire is smarter than me, but there it's 100% true in terms of if we look at a role specific, right? So I'll look at Jeannie as an example. Jeannie was my first executive hire as my as my CFO, I mean, she, you know, she knows orders of magnitude more than I ever even want to know about, you know, the finance role. And so when I look at it, it's less about me trying to go and challenge her to see if she understands the CFO-ness. That's what background checks and, you know, and stuff are for. What I want to know is, is she going to add positively to the, to the culture of 1Password, 'cause it will change, right? It will change when you bring in somebody. And she's been the most wonderful, you know, human to bring into, to, to us as a company. And she's absolutely positively changed the culture of, of, of 1Password. And that's, that's what's most important is to, to try and understand ahead of time the, what I call attitude and aptitude, right? And, and the second side of aptitude, because The attitude, I think, is really important from culture. The aptitude, it comes down to they may be great people and they may be great additions to the culture, but they may not be a fit for where we are as a company. And we've seen some of that where at a company, you know, I would say of our size and certainly under, you need people who are going to, you know, be on the ground doing, right? And, you know, I understand some of the most experienced, you know, extraordinarily talented people are out there, but they may have been at companies that are too large for too long and things like that. And they may have, you know, they may have lost some of that, you know, boots on the ground experience, or that may not be what they're looking for. And so you have to be careful not to, hire, um, somebody who's, who's been away from, you know, the real doing for too long unless they're really just like gung-ho to get back into it because, um, that can just turn out to be something where great people, just not a fit for the company.

Yeah, great people with great pedigree. So, some, so many of my clients will, you know, sort of say, well, they worked at LinkedIn or they worked at Facebook or Google or whatever, and, you know, kind of fall in love with the resume, but not understand to your point, like what's needed right now in this role, like do you play Do you need someone more strategic? Do you need, you know, someone who's gonna be, um, an excellent people man— manager? And, and it's really the— their pedigree is kind of beside the point. I think it's so important to really look and how— I guess I would ask you, how did you actually look and how do you now look to make sure that this is the right person at the right stage for your company?

Yeah, and I don't think it's look, I mean, you just have to talk to them.

Hmm.

You just, I mean, you just flat out have to talk to them. And so when we hire senior people, I'm sure they're probably sick of, of, you know, sick of, of how many interviews we put them through in a way, because, you know, we do, um, we do get put them through quite a bit. Um, you know, probably half the ELT, like our, our, our C-suite talks to them. I talk to them multiple times. Katya, who's our chief people officer, talks to them multiple times. If they're in a senior enough role, we even have our, our, um, you know, two key investors and, and, you know, the founding group talk to them. And it may not all be individually, but just everybody's got a different point of view of what they're looking to, to understand from that person. And it's that combination, I think, that's important. Any one person, I mean, to a certain extent, any one person can have the, you know, what I call executive footprint in the forehead and say, nope, this, this person won't. You know, just won't do, which is rare. Usually, you know, we're all sort of like yes or no. Um, but I do think it's important to get that combined, that combined group. I don't think there's any magic to, to looking at resumes and understanding what works better or, or, or worse. I've found it's, uh, location-wise, uh, company-wise. I mean, unless you're looking for a very specific role where, you know, say security where you want to have a security background, very little of that.— is a real indicator to success. It can be a great resume or a mediocre resume. We're, we're just not gonna look at the poor resumes.

Right, totally. But how, what, what's a mistake that you maybe made, you and the team made about, you know, sort of hiring either someone senior or, you know, not even so senior that you kind of learned from that you then kind of baked into your process?

Yeah, I mean, I know it's, it's probably the same answer everybody gives, but it's so true and that's just not, not, you know, um, deciding quickly enough it's not working out.

Uh, yes.

That's, you know, it, it, it's just so true. And, and, um, you know, it hurts both parties. It hurts both parties. It's, it's something that I hate doing, right? But you don't want to ever get to, to where you don't hate it. Like you don't want to be that person, right? Um, but it's so necessary because it helps the company in such a positive way when you make that decision. And that doesn't mean the person has to even be, you know, horrible at their job or anything. In some cases, it's just the combination of subtleties that just mean it's not working and it's adding friction to the system. And I think that's the challenge, right? I think if people look at it and say, hey, this person is putting boulders on the road, That's an obvious one. And, and that's where you make the decision fairly quickly. Right. But sometimes it's just that, you know, it's, it's just that, that, you know, I don't know, the analogy would be they're, they're leaving, you know, big grains of sand behind. Right. All wherever they go. Um, because the person that drops a boulder once in a while is, is, is sometimes far less of a problem than the person is just always sort of making your path gritty. Right. Like it's just, You know, I, I, I don't know where that analogy came from. Brenda and I, my, my wife and I have been talking about getting our driveway paved, so that's probably why, which I, you know, but it's—

I love that.

That, that is the challenge is sometimes it's not the obvious, you know, there's nothing where it's like, yep, you did X, off you go. It's just here, it's, it's just causing friction.

Yeah, causing friction. Now, one thing that, that 1Password did for a number of years, if I'm not mistaken, you tell me, 14 years you bootstrapped the business.

Yes.

And I guess I'm just curious, what was that a conscious decision? Tell us about the nature of why you decided not to take, not to take outside investors for a long time.

Yeah, I, I mean, at the outset, you know, Dave, Sarah, Aristo, Natalia. Now Sarah in particular is the, you know, she's the one that's gonna keep us on track, you know, in the early years financially that, You know, and she and her potty mouth. Her potty mouth. Yes. Only when she's happy, you know, but the thing with Sarah is like, again, like the four of them found, it's a typical, you know, they were living outta their parents' houses, you know, starting up this company and, you know, I think at the very initial years, to be completely honest, and perhaps 'cause they, you know, were out of Ontario, I think they're out of actually St. Thomas and Toronto. Didn't realize that you could probably get investment or didn't realize that was a path to go down at the very beginning. And so you have to use your own money, right? Like, it matters. Like, you know, even, even, you know, 13, 14 years on when, when we'd grown the company, like, we'd pay ourselves if there was profit, right? And so all of a sudden that matters. And, you know, so for the early years, it was out of necessity. But as we continued to grow, You know, we were fortunate in that the way we grew the business, it was very much of, we're gonna be very thoughtful about this. So I would say like one of the biggest changes was in 2014. And in 2014 I said, hey, we're gonna go and build a B2B app and we're gonna build a SaaS app. We didn't have either of those at the time and we wanted to have it a SaaS app so we could offer things for families instead of just individuals. And then we wanted to do the business app 'cause I saw a real opportunity there. Well, this was going to be a huge expense. You know, we were— it took us ultimately 2 years to build this. We had to hire a whole bunch of developers and a bunch of, you know, people that knew infrastructure and stuff like that. And so we had to save for it ahead of time and, you know, make sure that we had the opportunity to see that through. And you have to take some of those bets. And so it's a little bit like running your household all of a sudden that really matters. And you think about things like, You know, do we need the big fancy office? No, we don't need the big fancy office, right? You know, what do we need? Really good developers and designers and customer support. And, you know, it's the people. And that's where we spent the time, focus and money. And then the learnings really came from our customers. They will tell you what's good. They will tell you what's not. And so, you know, I would say I waited too long before taking funding. Funding has absolutely has valid purposes and reasons, but at the same time, knowing the difference between a customer and a user is really important because, you know, if you think of it, if you have a good idea or if you have what you think is a good idea, you go to your family, your friends, your neighbors, you tell them their idea. What do they all say? What a brilliant idea.

You're so great. You're so smart.

You're so great. It's so absolutely handsome.

Yeah.

Yeah. I don't get that often that I'd like. But if you go and instead you say, hey, I built this thing, would you pay $1,000 for it? I don't need it right now. Or, you know, I'm a little short in cash. Like, you get the real world. And so the difference between a customer who's actually going to pay for something and a user is they will tell you where the value is, you know, that's immediate to them and they're willing to pay for it. And so there is something valuable about growing a cust— uh, growing a company with customers as opposed to, um, hey, you know, like we've, we've got a bunch of users, but we're losing money every year, but it's okay because we, we have the funding. That can be valuable at times, just, you know, like I, I would say in general, far too many people take the, we'll just pay our way into, into growth as opposed to, to really understanding it from a customer perspective.

Yeah, it certainly forces you to make, you know, the so-called difficult choices and to run lean and all that stuff. And I'm curious if you could talk more about what you just said, which is, I think, I think I took money too late. So like, what was the point where it sounds like you were building that, that B2B, the B2B use case and the B2B product. And that's when you really realized we're going to need funding. But even leading up to that, what are some of the markers for anyone who's bootstrapping? What are some markers to realize, yes, you're doing it right. Keep going, keep bootstrapping. Or it might be time for you to switch and now take in a round of funding. Like, how do you think about that?

Yeah, it— each round of funding has to have a specific purpose that drives you closer to achieving the vision of the company. So in, in our case, it was, you know, we launched, um, B2B in 2016, and, and we didn't take the funding until the end of 2019. And the, the difference that I saw was, you know, at the beginning, you know, May, uh, May 21st, 2016 is when we, They took 1Password, I think for Teams it was called at the time, out of beta. And it sort of hockey-sticked our growth from a B2B point of view. And we started getting quite a few customers. And we were, our company was half engineers and half customer support. Build a good product, support the heck out of your customers. That's how we grew. And I had built relationships with a ton of VCs, but again, we were still profitable at the time. You know, we didn't need the money and I didn't really know what I would do with it at the time. It wasn't a case where if we had an extra X number million, we could do something. But I started to realize, you know, maybe in late 2018, about a year ahead of when we took funding, like we need to mature as a company. I choose a theme every year. And so I chose the theme like a little bit later in 2019 for the year 2020, growing and growing up is what I called it., and that was the purpose of the round. And, and the purpose of the round wasn't to just hire more people, but to sit there and say, okay, we've, we've got, you know, a group of engineers, we've got a group of customer support. We want to continue hiring both of those. But imagine if I could have a world-class go-to-market team because we were getting larger and larger customers who had more complex needs and wanted MSAs and, and all of that sort of stuff, right? And need their, their own, you know, need the account managers to, to handhold them and, and things like that. Imagine if I had world-class marketing so that people actually understood that we had a B2B offering. Because no, even today when I go and talk to 1Password, a shockingly large number of people don't know we have a B2B offering. And so, you know, it's things like that. We were doing, you know, cash accounting in QuickBooks and that's just not how you run a business, right? And so, you know, that's where, like I said, Gina was my first exec hire, right? So I wanted to grow these orgs, but I didn't know how to do that. Well, I knew how to do that, and that's attract world-class talent to lead those orgs. I didn't know how to go in and attract world-class talent. People didn't know that we were a successful business, 'cause again, we were bootstrapped and private and in security, so we were even more private. And so that's where I went to, you know, Arun at Excel is who I sort of built the best relationship and said, okay, like, we'll, I'll let you, you know, come in and, you know, do a round of funding., but we're going to also use it as sort of that kickstart, that public, hey, we're a real company. And that's really what got us started. And so we did that, I think officially right at the end of 2019. And in January I hired Jeanne and, you know, poor Jeanne. I mean, back at, we were so immature at the time. I said to her like, well, we'll, we'll, we'll get you some stock options, but you've gotta go and build the stock option plan first. Okay. So, It's a, yeah. Well, how they didn't turn her away. So, yeah.

So that's hilarious. Well, I think it's, I just wanna highlight a couple of things you said. It's so strategic because you were saying where, first of all, something that very few founders have the opportunity to say, which is, okay, we're gonna take your money VC, because you already spent the time and energy building a profitable business on your own, you know, with your own sweat. And so that's one thing to say. And the second is to say that Not only are we gonna take this money to turbocharge and, and have world-class hires and really move forward, but we're gonna have a coming out party. So it's almost like building our brand, making sure people know we're out there, customers, businesses know we're out there, but also that we're successful enough to bring on these, you know, higher level executives who really knew what they were doing. So it was like a, a lot of things kind of coming together is what it sounds like.

Yeah, that's right. And like I say, it's all about how do you put your vision first? How do you sit there and say, hey, like, we're trying to make it easy for people to stay secure online. That's our, that's our goal in life. But in order to do that, people need to know we're out there. And so that's, you know, that's a big part of how do we, how do we get forward? And then, you know, some of the money— and this is admittedly an Arun term that I'm stealing because I think it's wonderful, but it's like, the money itself can be courage capital. It can allow us to do things that we wouldn't otherwise be able to do, you know, whether it's acquisitions or whatnot. Again, especially because we can stay profitable, we don't need to use the money for day in and day out, you know, operations. We can actually look at the opportunities to, to advance the company's mission all that much quicker.

Yeah, I, I just also wanna take, I wanna notice that like the way you're thinking about this is not the way startups, let's say, were thinking about these kinds of things in, in that time period, you know, sort of the, the late 20-teens or whatever into 2020 and 2021 in the sense that you were really focused on building organically and not, as you said, attracting users and getting footprint, really focusing on gaining, earning customers. And I'm just curious, you were born in Waterloo, your company was born in Waterloo and not Silicon Valley. And I'm just curious if there was maybe a cultural difference that allowed you to build and to, to think about the company in that kind of a way. Like how did the influence of place, or did the, did place have an influence on the way you all thought about it?

Oh, oh, definitely. I think it did. And I don't think there's an, there's necessarily a right or wrong in either approach, to be clear. I think both approaches have their different advantages, but I like to say in order to have a business, you need to have two things. You need to have the innovation, but you need to have an actual customer. You need to actually know where the value is that people will pay for. And both those things have to come together. You know, being out here in, you know, I went to University of Waterloo and Dave and Sarah are in St. Thomas, which is just a couple hours south, and Rustam and Natalia a couple hours north in Toronto. Like being in this area, it is, you know, a pretty hotbed of technology, especially now, but it is different from, you know, from the Valley. It is different from San Francisco. And because of that, there are fewer options, even back then, I would say fewer options for VCs than in San Francisco. And a slightly different, I would say a slightly different focus from the, you know, from the innovators. And I do think it's positive. There are now more and more of the, like Velocity at University of Waterloo is an accelerator and things like that, that can help these companies. So it is continuing to change, I think, for the, in a positive way in that these companies can help be brought forward. But I think there's still— I'd say a slightly more challenging time getting funding out here, which I think is a positive. It does make you understand, you know, I got asked, I was at the University of Western and I like to talk to the, you know, to the kids. I'm 56, they're kids to me, you know, to the kids there who are starting up their own companies. This is the TechX, so their accelerator program. And I remember the one And the one person there asked me, and she asked me like, how do you know if you have the billion-dollar idea? And I said, well, I don't know that you, that there's such a thing as quote unquote a billion-dollar idea, but there's definitely billion-dollar problems. And I said, so if you can focus on a problem and a problem that, you know, people are willing to, you know, pay to help solve, and if you have an idea on how to then solve that problem, then you've got something because that problem, if it's a billion-dollar problem, somebody's gonna make, or a combination of people make a billion, and then you just have to figure out if that's gonna be, you know, if that's gonna be you. And I think it's that same, that same focus of, of are we solving a business problem first and foremost, or do we just have an idea? And that to me kind of goes hand in hand with that user versus customer discussion.

I love that. I think it's so important and also I think methodical in your approach and I, I really appreciate that. I'm, I'm curious. I mean, as we've been talking about funding and bringing on funding, someone you didn't mention is Ryan Reynolds, who I think is one of your investors. I mean, does everybody ask you to tell them a Ryan Reynolds story or just me?

Ryan Reynolds is a, look, Ryan Reynolds is absolutely everywhere these days, which is, you know, probably part and parcel of Deadpool. But yeah, he, he, we brought him on along with, geez, ton of incredible folks like Trevor Noah and Murray Barra and just Robert Downey Jr., like a ton of fantastic folks. And so I always sit there and say each round of funding has to have a purpose and the money can be at the core of a purpose, right? It doesn't have to be in our case. I really don't think it was. We took on, you know, a big amount of what I call courage capital because again, we To this day, we remain profitable, but that has allowed us to purchase a, you know, to, to do some M&A and purchase a few companies. But when I look at it, you know, the Ryan Reynolds of the, of, of the world and, and things like that, I look at it and I say, imagine what it would cost for us to get all of those fantastic, well-known people to even mention 1Password. And here they are giving me money, right? Yeah, well, not me, but at least the company, right? And so of course it's an investment, of course we want to give them a return and things like that, but we actually explicitly said, let's go after a bunch of these folks. Now, our investors, again, ICONIQ in this round, did a fantastic job of hunting folks down. Couldn't get everybody that we were looking for. You know, I'm a big Lewis Hamilton fan, and so I was hoping to get him, but I think he was busy driving or some such thing. So, but you know, again, we got a ton of fantastic people, and I have to say, Ryan, you know, is a proud Canadian. It's, you know, and one of the nicest people, brilliant. Like again, you know, as a human being, he is as nice, you know, one-on-one as he is, you know, as he appears to be in the present. Fantastic human being, but also a proud Canadian. So we were super excited for that reason alone to have him on board. But No, it, it, it really, the goal behind that was, you know, how do I get the average person to, to know who 1Password is? And the average person doesn't care how much money we raise, doesn't care who the investors are from a, you know, VC perspective, but we'll know Ryan Reynolds, right? And we'll know Trevor Noah and folks like that. And so, you know, when, when we can bring some of those folks on and, and, you know, mention them as investors, it allows us to reach, you know, a lot more of, of the average people that are outside of our sort of tech community that also need to stay safe online. And that was a, that was the, the ultimate main reason.

Yeah, I, I, I love that. And I think it's so, again, very strategic. And I, I feel like the way you're, you think about the different funding rounds is kind of what is the purpose of this is an important lesson for all founders to take into account. Is there other advice that you have for founders, for CEOs as they think about fundraising? Any other just advice come to mind?

Yeah, I mean, look, we've been in a very fortunate position because we've been profitable, so we've been able to certainly be in control of our own destiny. And that's, that to me is the, is the key. You know, they're the investors. It's a marriage, right? And so when I look at it, I have a fantastic relationship with Arun, with Will, with Anoushka. I think those are the 3 main investors that I, that I, you know, talk to. You know, they're, they're investors, so they're not operators. And, and, and so you have to understand what is, what is the value they bring. The value they bring is A, they know absolutely everybody. That's just, that's just their role., but they also deal with tons of companies that are just like my own, right? And, and I remember even the, the very first round, um, uh, with Accel, it was, um, you know, it was about talking to him and he didn't just bring me and, and sit there and tell me all about Accel. He just brought me to a bunch of different companies that they had invested in to talk to the different people and say, hey, go, you know, go talk to Mike and Scott from Atlassian, go talk to Slack. But it was just, it was fantastic because It was, here's the relationship he has with them, here's what, what they can do for those companies, and that's how we leverage them. So it's, it, it really is that marriage. And so it's not just who brings you the most money or, or, or the easiest terms. Terms matter, but it's who's going to continue to add value long past that date that you get that, that check.

Definitely. Definitely. And, and you've now spent, you know, this, the time and energy and the money and the resources building your company. You have 1,200 employees now, is that right?

Yeah, somewhere over 1,200. It's, it's a little ridiculous.

Yeah. Starting with those 20 people all fitting in a circle in the room.

Yeah. You need a big room. You need a bigger room.

Yeah. So what kinds of management practices do you find most helpful in keeping people aligned? And what, what are some of your success stories and what are the mistakes you've made as you've really tried, as, as this company's grown exponentially, trying to keep people on the same page moving forward?

Yeah, it's communication, you know, and the bigger— I would say the biggest thing I've learned is the bigger the company, the smaller the number of goals you can set at a company level. And so, you know, when I look at it, we've tried and we still run OKRs and things like that, and they have— that's been some of our biggest sources of mistakes and stuff like that. And, but at the same time, it has value. But, you know, last year, for instance, we just said, like, at a company level, here's the 4 themes that we're focused on, right? And the 4 themes for us, it was just, one was just, you know, enterprise password managers, just password manager. Like, hey, we're a password manager, that's what we do, continue to build it. Continue to listen to our customers, continue to make it better. The second theme was usability. I like to, sometimes I like to say externally, hey, 1Password is so easy to use, and internally, I'm like, man, we're so hard to use. Like, it's like, you need to have that attitude, right? You need to have that, how do we make it Angry Birds easy? Because level 1 of Angry Birds, right? You got a 3-stick house and an infinite number of birds. You can't fail the level. You know how to play the game. And we need to make, you know, 1Password that simple for new folks. And then, you know, uh, for me it's like growth at scale comes with new markets and new products. And so the market for us is, is MSP, which is a managed service provider. So they're, think of it as a company that, that's gonna do the technology for, for many small companies. So that was a new market where we're, you know, we're just launching. And then the new product, which is extended access management. So those were the 4 themes, you know, 1,200 people, 4 themes. And, you know, sure, like, we're doing 100 different things, but if we try and say 10, nobody can remember 10. Even 4 is probably one more than you can reasonably do. And so, it's how do you simplify the message so that people understand, you know, where we're going, how we're trying to achieve the vision, as opposed to trying to understand the details of each. And then you can have a whole bunch of lunch and learns and a bunch of things like that for those who are interested in learning the details. But it's the themes. And so a few years ago when we were probably 500, 600 people, I started with OKRs for the first time, right? Objectives and key results, right? Every company's got to try it at least once, I feel. And boy, have we made mistake after mistake after mistake. And I would say we're probably about 90% of the way there to making them effective. But the one thing I found, the biggest mistake with objectives and key results is You know, the first year we tried it, we said, well, if it's, if it's important, it'll be an objective. And so all of a sudden, like, everything we were doing became an objective as opposed to saying what the objectives were and then looking at what we were doing. And so, you know, that, that became a little bit of a, you know, it be, it became fake, right? Yeah. We didn't know it at the time, but it just became, oh, well, we're doing it, so it must be important, therefore it's an objective. And so I would say, you know, the OKRs are something that can be really valuable, But if you find as a company that you have people who are tracking the OKRs as opposed to just them being tracked naturally, it means your objectives are wrong. Because if your objective is right, then people are looking at it and going, man, how am I doing against this really important thing? If your objectives are wrong, you know, like if the OKRs are different from your real objectives, then you're going to have people who are just tracking the metrics to the objective so they can report it once a month, but nobody's actually using it to really understand how the business is doing. And so that's— it's shockingly difficult to get those two aligned. But, but it's working. It's slow, but it's working. I think the other thing we, we did was we kind of graduated. Every time you grow, expect everything to change. When we were real small, we were like, We're not going to have roles and titles, right? Because we just, we don't like, that's where, you know, we, we, we chose fun titles, right? So again, Chief Eliminator of Obstacles, I still prefer that over CEO, but you know, but then we let people choose their own titles as long as they, they weren't like official titles. Like you can't just name yourself a VP. Um, but you know, so we had, um, what'd we have? Uh, like Droid Developer, uh, was, was I think Michael Verde, if I remember correctly, but he was like on the, on the Android team, right?, but then we had people who would just choose weird, like completely meaningless names. And as we grew, like people knew, didn't know where to go anymore. So we had to choose real titles. Um, and, and we didn't want managers, um, because we just wanted, like, we didn't want the hierarchy. And then I remember at one point in time when we had our first manager, like we, we resisted it for so long. Then we made Rob our, our manager on the customer support side. And it's like a week later, you know, the gang of 5 of us were standing around going, man, these manager things are awesome. Like, it's, you just have to, you have to be able to say what is good for where you are at that size and position of a company and let some of your bygone, you know, bygones be bygone in terms of what you said you would never do.

Yeah. What was the hardest shift for you? One of the hardest shifts for you to make as in this very, these different moments of like exponential growth?

Yeah, I think the hardest shifts, there's two. One is fairly early on, there's a people shift. When you're a small company of 20, everybody's doing everything. And, you know, I was developing the product, something I'm sure our engineers are happy I'm no longer doing, you know, but you have certain people that have helped you so tremendously on the early days. And, you know, as the company gets bigger and now instead of people doing everything, it tends to be more, you know, now you have like the, you know, the world-class designers who, you know, that's what they want to do. They want to design, right? And they're awesome at it. And, you know, the people that want to help the customers in customer success and support, and that's what they're awesome at.. And so you, you lose, you know, you lose a little bit of the opportunity to do everything, but there's some people who, who, that's what they want to do. They want to be at a small company. They want to, you know, they want to work on everything, get all of those different opportunities, and then all of a sudden the company's outgrowing them. And these are the people that in many cases have been the most valuable to your success. And so you try and keep them happy. You try and keep, like, you, they, and, and, uh, and we are thinking we're doing what's right for them. Whereas again, that's a, it's, you know, that's, uh, I don't wanna say fail fast, cuz in that case it's, it's like not a failure. It's just you need to recognize, yeah, like that time's passed. Like you would be happier at a different company that's smaller again, and we'll be super sad to see you go as a, as a human, but we'll all be in a, in a better place. And that's, that's tough, right? There's some people, quite a few people that we've have that are now with, have been with us 10, 12, gosh, like 15, 16 years. It's unbelievable. And those are the folks that have done a, you know, have enjoyed, I mean, I'm going to speak for them and I hope I'm right, but have enjoyed, you know, moving to more particular roles or in many cases have actually grown up in leadership with us as well. But there is that early set of folks that some of them, what they want to do the most is just stay as a small company and do all of that. And it's, it's, it's sad and it's hard to, to make that change.

Yeah, it must be hard to discern too, because I think what people, people don't always know themselves, right? So then they're like, it's not good. The company's changing too much. We're too corporate. I don't, I don't get a say, or I have something to add here. No one's taking my opinion into account or whatever. I feel like those are some of the markers. But really the, those are symptoms, but really the problem is that this is no longer the right environment for either of us. And I'm just curious, have you experienced that?

Yeah, absolutely. Um, and yeah, I'm certain I can name names, but there's, there's been a few people, you know, the one in particular I remember and, you know, ultimately, you know, he left on very good terms, but it, it, it went too far. And to your point, like the change isn't dramatic and instant, right? Like if all of a sudden on a Tuesday we tripled our size, it would be easier for people to say, oh, I, you know, I'm, you know, not liking this, you know, new us. But it's just, it seems gradual and the company's having success and everything is positive. And yet, you know, certain individuals, and again, many people are thrilled by that and there's new opportunities and new challenges, but then And you know, there's that one person I think who's, you know, trying to figure out why they're not as excited about this as everybody else, right? And what I find is a kind of a key marker is you put them in like 3 different roles, like 3 or 4 different roles over the space of say, you know, whatever, a month or a year, I mean, 6 months or a year. And you know, it might be, well, try a leadership role. They didn't really like that or they didn't work out and try this role and try it, you know, because they're trying to find, you know, their position at this, you know, new us. And in some cases, that's, that's not what they want. And to your point, like, it's not like they know it instantly because it's not like the company just changed overnight. It's not like we know it. We're just, you know, we're all trying to work together to find out what works. And for some folks, that's, that's just not— that's not going to be the case. I think that's going to be the true— even from now, from 1,200 to say 10,000 or whatever the, you know, which, you know, so that takes a while. But, you know, but it's gonna be the same thing, right? When all of a sudden, like, all hands calls, you know, aren't all hands calls. And, and, and so, you know, I'm sure there'll be the next set of changes and challenges.

Yeah, totally. In, in this period, you know, as, as the company has grown and now that you've broken the news that you're getting to 10,000, maybe no time soon, but at some point, how would you say you've, you've changed as a leader?

My role has just changed dramatically. You know, when you're 20 people or even 100 people, like my role is to some, it just to a certain extent be viewed as the, as the, like, I hate to say the smartest person in the room. I don't, but like, that's what the Gang of Five are. Like, we're gonna, we're gonna be like, this is where we're going and this is why, and this is how we're gonna do it. And like, you know, you work with your teams and all of that, but that, you do that. And I find now, you know, my role is certainly gotten a lot more external than it ever was before. But I would say the biggest impact and the biggest role I play is to make sure that we're, we as a company are going, you know, towards that North Star. And I now need all of my execs and their leaders in that to actually determine how to get there and the right direction to, like, not the right direction to go, but the right way to get there and all of that. And so it's not, you know, if I'm the smartest person in the room, I think we're in trouble, you know, again, whether that's finance, whether that's engineering, whether that's, you know, design, whether that's go-to-market, you know, all of these things. But what I have to do is I have to keep my eye squarely focused on this is the North Star that we're heading towards because it's never— you're never going 90% off of, off-kilter. What you're doing is you're going 1 or 2% off and then going 1 or 2% off of that, 1 or 2 off of that. And then all of a sudden you're going, you know, 15 degrees off of where you need to go. So I would say the biggest change is really just to keep that focus while not being the one that necessarily understands How to, how to get there or, or what we need to do. And it's interesting. I've, I've found my role changes like most people's role, you know, like many, many people's role here as you grow, you know, every time we change by 25% in size or so, or 30% in size, you know, my, my role changes subtly as we get in more and more, you know, really talented people who are able to do their role much better than I could ever dream of. So, it's been fun because I enjoy the challenges.

Well, I mean, and I think it really pushes you, right? It really challenges you. I guess I'm curious, Shiner, what are some of the things that you would say that you're working on, that you're developing in yourself to make you a better leader, professional, or executive, or what kinds of things are on your kind of like development roadmap?

Yeah, one thing that I'm not good at is I'm very much focused on what, what can we continue to do better? So I don't, I'm not a, I'm not a, I'm a fairly neutral or whatever the right word is, neutral person from an emotion point of view. I don't, you know, I don't get too excited. I don't get too down or anything like that, but I do tend to focus too much on like, if we'll, if we'll have just finished something, it's like, great, what's next? And I have to step back and, and just celebrate what we've accomplished sometimes. And that's just not, that's not in my fibers. That's not, that's not who I am. But I do recognize, you know, that what that can lead to is people always feeling like you're dissatisfied when I'm not, not at all. That's just, you know, I'm just always looking, looking forward as opposed to, to, you know, looking backwards. And so You know, part of that, you know, you start to realize like that can be like, it's important for me to look forward. That's got to be my role, but it's important for us to celebrate the wins we've got and celebrate the achievements we've made so that the company understands like, hey, like I am like, I am proud. And as a company, we're proud of what we're accomplishing and things like that. While at the same time being able to then say, you know, and then a week later it's like, okay, and here's what we're doing next. Right. And, and, and But, so that's one of the big things that I want to continue to improve on. Now, happily, we've hired Jen and a couple of others to help with communication, so I can have them, you know, remind me, "Hey, like, you should probably just celebrate the fact that, you know, we just had, you know, awesome announcements on a Black Hat," and stuff like that. I'm like, "Oh, yes, yes. What a brilliant idea." Like, listen, I, you know. That's the nice thing about having smart people around me.

Yes, for sure. Capable people. That's really great. Now I wanna switch gears to this topic that I find so fascinating. You, is it, is it accurate that you have a farm, that you're a farmer?

It is accurate to say I have a farm.

Yeah. Tell us about your farm.

I, I, I'm not sure it's accurate to say I'm a farmer yet. So we do have a farm. We have a, We don't live on the farm, but we've got a 102-acre farm and it does have a real farmer that farms the land and we grow, we rotate between corn, soybean, and wheat. For me, I want to play farmer and that is my escape from reality. And so what I've actually been doing is playing, I bought a used tractor probably about 2 years ago. Just from an auction. And it was one of these ones, it was actually typical Canada. It's a great Canadian story because in Canada and probably, you know, Minnesota and other places like that, you know, you go to a mall, you'll see these tractors sitting there all winter and they're just there to plow the, you know, plow the snow off of the, you know, off of the parking lots. Well, because of that, they just get eaten alive by rust and that. And so you can buy them pretty inexpensively. And so I've been basically for the last year or so tearing this thing apart and rebuilding it and, you know, just having a wonderful time doing that. But I do, I do plan to turn it into a hay tractor so I can take a few acres of the farm and grow and roll up the hay as well.

Well, I mean, that's amazing. Is that— how does that fit into the picture, the multifaceted tapestry that is you?

That is my, that is my escape. That is my escape from reality. So I go there, I try and go there an hour a day when I'm in, in Toronto. I travel a ton, so it's not always possible, but I try and spend an hour a day. It's about 10, 15 minutes away from the house, and I just go there. I go there on my own, and I just, you know, it takes a lot of learning. I, I mean, I didn't grow up on, on farms or anything like that, so, you know, just spending a bunch of time there, but it's, it's my way of just forgetting about stress. I don't put any timelines on it. It will take as long as it takes. And, um, using my hand, I come home completely dirty and run for the Fast Orange Hand Cleaner and stuff like that. But it's just, it's how I just escape reality for an hour and just clear my brain a bit of, of, of the stresses of work. And it's, um, it's very important to me in that regard.

Hmm. That's lovely. So it's kind of like almost a meditative practice.

It is. It is, you know, like Dave and Rustam, um, I, I, I don't know if they're still into it, but they were big into yoga for a long time. I've tried it. I hate it. It stresses me out. I don't stretch. I don't bend. I'm going to do the dirty hands in the tractor route. Um, nothing against yoga. It's great for people who can do it. It is not me.

Yeah. Yeah.

Yeah.

I'm a weightlifter myself. I can't relate to yoga at all. But I think it's really helpful for everybody to have a practice and actually a physical practice one way or the other, a physical practice to really help them, I guess, balance out the heady side of us. Yeah.

Some, I always say it's like something that takes enough attention that you can't focus on work, but isn't stressful to the point that it's just adding to your stress. It used to be Lego for many years and, you know, I've still got a Lego kit that my friend gave me here, you know, that I'm working on. So just something building for me has always been fun, but getting my hands dirty is a little bit more fun. I do have green paint all over my hand because my green John Deere paint exploded in my hand yesterday, so.

Battle scars. I love it. I love it. You know, Scheider, if for any leader over a career of decades, you have highs and you have lows. Can you share like maybe what one of your big highs was and what one of your big lows was?

Yeah. My highs are, I think, mostly people-related and perhaps not something that happens quickly, but it's just, you know, seeing some of the folks, you know, the Ricks, the Michael Fays, the Matt Davies and that, that I've worked with for many years and, And to see them grow into really capable leaders, like that's what I enjoy. You know, Jeanne would be a great example of that. She came on, you know, at the beginning of 2020 as our, I think VP titled role, but the head of finance. She's grown her team. She's now our CFO and she's just done a tremendous job and to see her grow. Has been tremendously satisfying to know that I've, you know, I don't know, I played some role in it and, you know, I just find that tremendously satisfying. I would say the one of the, one of the times that I remember probably the most, most sad I've been, I'd say, at work outside of, you know, like personal things, but from a work point of view was actually back at IBM. When, you know, I was working on e-commerce for many years and I had been working on something. I won't go into the details, but I've been working on something that I thought was super important and for the life of me could not get my, you know, my manager to understand that it was important. Now, in hindsight, I could have been wrong. I mean, I, you know, maybe I was wrong and she was completely right, but it was just, it was so frustrating that I couldn't communicate the value. And, you know, it was something that I just felt really important on. It was really important. And I just, I ultimately couldn't communicate the value of what I was trying to accomplish. And, you know, could see again, this is where I was adding the friction ultimately to the system because I just had completely different beliefs. I ended up, you know, that's where I ended up leaving IBM at that time and saying, hey, I'm going to go and do the consulting route in the US where I can, put more of these beliefs to practice, but it's just, I find that to be a, to be, if I can't, you know, help others understand where the value is, I get really frustrated by that. Now, I would like to think that I can, you know, now, especially with the great people that I've got around me, like understand, like, hey, you know, as Rick likes to tell me, like, China's got 12 ideas by noon, one of them might be good. So, I gotta recognize that it's, it's, it's quite possible it's one of those other 11, but, um, but yeah, that was, that was really sad. I was just, I was so convinced that it was, it was of value. Um, but I, I couldn't over many months express the, the, the, the value in that. So that was a, that was really, uh, frustrating and, and, uh, sad for me personally.

Yeah, I can relate to that. And also it sounds like it really pushed you to do the thing you needed to do next.

It did. It did. Again, like I, you know, it didn't make much sense to, to, you know, stay there and again, be a, a part of the friction. Like ultimately whether I was right or wrong is irrelevant, right? I wasn't in the, in the position to, to make the call. And I recognized that and I wasn't gonna fight that. And, and, and so that part of it was fine, but it was just, it was just, you know, like you say, something that led me to, to, to move on where I could be in And it's more of a decision-making capacity.

Right. Just a few more questions. Have you ever experienced imposter syndrome or severe self-doubt?

Yeah, I don't know about severe self-doubt, but definitely imposter syndrome and definitely, you know, definitely doubt, you know, like you say, imposter syndrome is always like, at some point they're going to find out I'm not an X, right? Like, you know. I wouldn't say I've overcome that, but I've started to realize, you know, like it's all about doing the things you don't know how to do. That's how you grow. And I, you know, again, it's the tractor. I have no idea how to, you know, fix a tractor. I've never been a mechanic. I've never, you know, gone for education, formal or otherwise. And yet I've pretty much torn the tractor apart and rebuilt it and it actually still runs., and it's just, you know, it's just learning. And so I do think imposter syndrome is, is there, and it certainly was, maybe I'm just getting old, but it certainly was there for many years because I'm a developer. That's what I do, right? I, I code. I, I haven't coded in years now, but like, you know, here I am, you know, on live TV and podcasts and like, what, who am I to do that? And I'm, I'm leading a team where, you know, I've got Everything from the people to the legal to the sale. I, I don't know anything about half of this. Like, you know, you, you do, you do see that. And I think the, the guidance or the advice I would give to everyone is, you know, um, give yourself that, give yourself that sense of, of, of ability, you know, believe that you're, you're going to be able to do it, but then be honest with yourself in terms of the results. 'Cause if the results are crap, you know, maybe that's not an area of strength for you. So I do, you know, there was a great conference, a great talk by Don Melton, who is the founder of WebKit. And he said that great things are done by a combination of ignorance and hubris. 'Cause if you knew how hard it was, you'd never try it. And then you just have to have sort of the, you know, the hubris of, you know, my son's 24 and it's, you know, he's just starting to recognize that he doesn't know everything. But you know, like you go from whatever it is, 18 to 21 or whatever those ages are where you know absolutely everything. And that's, that's the hubris you need. So it's, it's, it's true. Should probably temper the hubris, but you know, it's that, that sort of attitude you have to go into things with.

That's so great. And what do you wish you had known earlier on your journey?

Oh my. Um, I guess it really is the importance, uh, I, two things, a good and a positive and a, and a negative. The positive I think is just, you know, get those smart people. I think when you're earlier on in your career, you can be a bit threatened by the, you know, the really capable people, right? Get the, especially those that you put in a leadership role that know more than you in their particular topics and things like that. Live with that. Like, understand that there'll be a level of, am I threatened by this person or things like that? That's You know, that's okay, right? That's just gonna push you to, to, you know, be harder, but don't let it become a barrier to, to hiring those people or being, you know, transparent with those people when you don't know something. I think that's the, the biggest, you know, um, way that you can move yourself in a company forward. I would say on the negative side, it, it's a tremendously lonely job as a CEO. Um, doesn't mean you can't build good relationships with the people, and I have, but there's, there's, there is still that power imbalance and things like that. Like, you need to be there for when your folks come to you with concerns, be they work, personal, whatever. Um, and it's very difficult to go to, to, to people because again, my job— and maybe I just haven't learned that this isn't really my job— like, my job is to take away the burdens, to, to, to help the folks. So it's, it's, um, it's a lonely job. It's not It's not for everyone.

Yeah. Yeah. Wise and very realistic. And last question, what advice do you have for others, other founders and leaders as they embark on their journey to grow into leaders?

Uh, again, I, I think it's, it's what I said is surround yourself with, with great people. And that can be your investors, that can be, you know, um, different groups. Like there's the C100s, there's, you know, a, a bunch of different, Groups that you can get involved in with other leaders, whether it's founders or CEOs. Again, hire the— but just hire the smartest people you can and surround yourself with people that are more experienced that can talk you off a ledge every once in a while, because you'll need to be talked off a ledge every once in a while. The other thing that I've used personally, and I don't know if this is going to help others, and I use this more for things where I get nervous, so, you know, live TV or stuff like that, it's just like, A week after the event, nobody's gonna remember it. Like you'll remember it. I can't, I can't watch or listen to myself or anything like, but nobody else is gonna remember it like a month later if you, if you screwed up, right? And so you'll feel terrible about it and stuff like that, but just, you just gotta learn like, hey, a month later, you know, it will all be over. It'll all pass. And you just gotta look that month ahead and say it'll be fine and, and not let things like that, um, really paralyze you with fear, because they can, especially, especially earlier on in your career.

Excellent advice. Excellent advice. Sean, this has been such a great conversation. I really appreciate your time. I appreciate the discussion and how honest you're being, and I just think people are gonna get a lot out of this. So thanks for joining me.

Ah, it's been a lot of fun.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts, so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.