1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO)

Brett: Well thanks so much for joining us.

Jeff: Yes happy to be here. 

Brett: maybe we could start with the sort of story about how you got involved with the company.

Jeff: Yeah. I've been, wow, 13 years now. It's been a, been a long time. And so, it started with two founders, so Dave and Sarah Roustem Alia, those were the two founding families of 1password Well, Dave and Sarah had been friends of mine for many years ahead of time. back in the late nineties, very late nineties.

I was actually Dave's boss at IBM. And so we were building e-commerce back at the time and he and I worked together and then we both moved to town homes, which turned out to be just up the road from each other, technically on different streets. 'cause we kind of backed onto each other, but just, just up the road.

So we became family friends for a number of years and then, both sort of moved our way, both from a work point of view and also from a, you know, where we live point of view. And [00:02:00] then around the end of, of 2011 that Dave reached out to me and said, Hey, he's, he's got this company.

And it was getting bigger. It was up in, I dunno, getting close to 20 people. And, you know, he wants to build and invent. He doesn't necessarily wanna, run a big company, which, you know, when you go from nothing to 20, it's, it's a big company. And I was working in the us I still lived in Canada, but I was doing the road warrior thing, leaving Sunday night and, doing consulting, actually eCommerce consulting from Sunday night to Friday.

And then, driving home and. We had actually just been sold, to Publicis. So we had started, when I had started there, it was a company called Berlin. It was about 200 people. We'd grown it, merged with a company called Rosetta. So now we were Rosetta and then just sold to, to Publicis. And so, you know, it was, do I want to be part of a large, 50,000 person company again? Do I want to try something new? So it was great timing for me. as a result of that, I, spent some time with Dave, spent some time with Roustem looked at the company, really got excited mostly by what they were trying to accomplish, right? That combination of productivity and [00:03:00] security. Make an app for people, you know, build a good product, support the heck outta your customers. That was their way of building the company, which really appealed to me. And so it just became, this is great. I want to be a, I want to be a part of this. And, we'll just figure it out as we go. And, that's what we did. 

Brett: So what was the state of the company? You said it was about coming up on 20 people.

Jeff: yeah, it was all consumer at the time. honestly, it was mostly Mac. It was like Mac and, iOS. It was, very, very little. I think they had a reader for Android and, something similar for Windows, but it was really very much of an Apple focused company, around 17 or 18 people.

I can't remember the exact number, but again, very small, but, growing, it was, it was growing organically and the company was doing well from that perspective. but that was, that was it. There wasn't a, vision, I would say, other than build a good product to support the heck outta their, customers, which is what the company was.

It was a boat. Half, I'll say engineers, half customer support. But even back then that mix itself was very mixed. So almost every night we would make sure all of the customer questions were [00:04:00] answered. Doesn't matter who of us were answering, we're all answering the questions. And that's how we grew is by listening to the customers back then.

And, it was all licensed based as well. And that was the interesting thing. So it was, you know, you would buy the license of, I don't know what password, four maybe it was, or three, I can't even remember the version back then. And you would hold that and then you'd sync through something like Dropbox or iCloud it was a very young company, but it was, you know, even back then, the brand was known and the brand was, was well respected. 

Brett: And what was the, the origin story of the company when it got off the ground? Like where did the idea come from?

Jeff: It's a little bit of you know, an inside joke slash lore of it was a 30 day project. That's what it was. So Dave and Roustem had a web, company where they would build you a website. You gotta remember this was what, 2005? Right. that happened back then and they couldn't, win their bids.

They were always being underbid. And so they thought, well, okay, you know, most of those websites were gonna be commerce websites and things like that. And, they were building them for small companies, so they had to do that very inexpensively. But you still needed things like to be [00:05:00] able to sign in or to be able to add your address or, credit card.

And so they thought. One of the ways that we can make it less expensive is to, automate some of the testing. we'll just spend a few weeks, build this tool that will allow us to autofill so that when we do testing we can, use that tool to autofill addresses and credit cards and sign in and do that sort of stuff. And as they start to build it, they start to realize, well, this would be really useful, like for themselves. And so they added the security part to it so that it would be more than a testing tool to actually be secure. And they thought, wow, this is really, actually quite useful for themselves. And so they put it out there on, the shareware sites and that where you could go and charge, I don't know what they charged you know, 20 bucks or whatever they charged for the, for the app back then.

And pretty quickly people started buying it and they actually started making more money from 1Password than they were making at their own job. And it wasn't long after that that they said, well this is our way forward. It's to actually do what's a, making us money.

And b is, is the product that they found so useful. it's kind of an interesting story and, I mean, you gotta remember, these are, they're living, I think at their parents' houses. [00:06:00] It's the typical, bootstrapped, out to their own garage as it were. But, yeah, it was, it must have been quite the, quite the experience for them. 

Brett: So you mentioned this maybe at a, at a little bit of a high level, but what did you see in them and what they had built, given things were still so nascent when you committed to joining them?

Jeff: Yeah, I think there's two sides of it. There's the, the company slash product side, and then there's the personal opportunity side. For me, it was just, don't get me wrong, I loved my time at IBMI still say I blew in my blood. The time at was really, of transformative for me as I went from the architect to actually running the p and l of, of a big part of the company. But there was just such an appeal to, again, being part of something where I could really make a difference. I went back to being the programmer, with all the challenges that that took for that at the beginning. 'cause I'd never programmed, you know, on, on, iOS or Mac before. And it had been a while, but like, that was, fun to just, to be able to, to have such influence on a small company and be part of that small group as opposed to. I don't mean to meanly, but being a cog in a [00:07:00] much bigger wheel. So personally, I found that very, appealing. It was just to be able to be a part of that and make that difference. But at a company level or at a, at a product level. Again, both from the way that they ran the product and the product itself. I'd been in e-commerce again since the, you know, the late nineties when IBM had brought me in, I started to see that e-commerce was really taking off. This was again, 2012 at this point in time that I actually joined and. There was a need for security online. There was, even just the knowledge of being, of needing to be secure online was just starting to creep up in, people's mindsets, right? the development community that worked online, that worked on, the new products and stuff like that, they were already recognizing, and that'd be, that was very much who our customers were at the beginning, was just other tech people who started to see the type of data that was being stored online and, and started to realize, hey, there's, there's a wealth of information here that needs to be protected.

But the average, person on the street was just starting to understand that using, you know, full cap for their password wasn't a good thing, but didn't have anything they could do about it. [00:08:00] And here we had something that not only could they use 1Password to stay protected, but we wanted, their input.

We wanted to know how to make it easy. We wanted to understand how do we make it actually useful for them. All you can aim for is not being intrusive with most security tools, right? You think of a lot of security tools and they're stopping you from doing things.

You think of maybe A VPN as sort of that middle ground of, it just runs and you hope it's doing something good and, and it usually doesn't get in your way. Here, we could actually make your lives easier because, not only could you be more secure, but just logging in, just filling in credit cards and addresses and stuff like that was so painful back then and, most companies didn't even remember it for you and stuff like that.

We can make your lives easier and more secure and that was just super appealing at a time when the, internet and internet shopping was itself just really starting to mature. So it was, it was a lot of fun. 

Brett: when you decided to join, did you think it is likely this can be an absolutely massive company, what was kind of your mindset around the [00:09:00] potential trajectory to build a really very, very large business?

Jeff: I still kind of think this way. I used to have a saying like, I can double the size of your company. I meant that by people, because I can always look around and say, there's Sue, there's Chris, whomever. You know, they're doing a good job. We could have another Chris, we could have another Sue. But I didn't know what to do with 10 Sues. I didn't know what to do with 10 Chrises. So I could see the growth, I could see the opportunity, and I could see, again, this is a case where it sounds somewhat silly, but it's like everybody in the world needs 1Password. and you think that's.

For the most part true. But I didn't think of at the time of, Hey, we're gonna be multi-billion dollar companies, and that's the opportunity. That wasn't the allure, that wasn't the appeal. but there was very much of a, people need this, like we can really help a lot of people. I didn't know what a lot was.

I didn't, I I didn't have it in my mind of, here's this humongous opportunity that's gonna grow into, something that, where I'd be sitting here today or, things like that. But I did see the opportunity to protect a lot more people that were, than were there. It was a problem that was, I think everybody could [00:10:00] start to recognize and that was appealing to me.

I think it was probably a few years later that I started to, to realize, yeah, there's a really big opportunity with this, 

Brett: Did a lot of your peers and former coworkers think this was odd, what you were going to do? Like, was it a weird thing at the time?

Jeff: Yes and no. I think those who, knew me best knew, I just, I love to problem solve. I love to sit there and figure things out. I do like to, I'll call it lead. And that's being nice to myself. Like I do like to talk and voice my opinion so that you know, I think that they knew that I liked to be in a position where I, where I could help make the decisions, help with the ideas. So I don't think that side of it was, a surprise to anyone. I had never had this, I want to be a CEO my whole life. never knew I wanted to be, I always had my career kind of grown by who's the role I want next, like, who's doing what I want next? so I don't think anybody looked at it and said, oh, well, Jeff always said he'd wanna be a CEO.

I had no idea. so that part was a surprise. I think going to such a small company was also a surprise [00:11:00] to people because I'd worked at the large companies. I mean, I'd, I'd left IBM once in, in, in my. Early career and, and went, worked for a startup I was not part of the leadership. I was part of the startup, so that's not super foreign to me. But I do think people were somewhat surprised to going from this company that had grown from 200 people to, you know, 1100 got bought by 50,000 person company and, I was, one of the most senior people there of the 1100 out of the 50,000, to be clear that I would then all of a sudden go to the small company.

But I think those who knew me knew my goal's, not based on my career's, not based on like, hey, some sort of status. It's, based on what's interesting. And I think if you're in computers, especially back in 20 12, 20 13, it's not all that much different. Now. You knew that your, your career was safe.

This company hadn't succeeded. It's not like I, I would never find another job, which hadn't really occurred to me much. But I think it's sitting there in the back giving you comfort to make some of these decisions that, that otherwise might seem scary. 

Brett: you joined as CEO in 2012, and that very rarely [00:12:00] works, at least in, in terms of statistically in Silicon Valley. If you think about founder-led companies that bring a CEO in that early in particular, so when you reflect back on the last 13 years what's the underpinnings of why it has been such, a productive dynamic?

Jeff: I think there's a few things that came into that. First of all, they did bring me in CEO from a standpoint of when I signed the paper it said CEO, but we also agreed not to tell anyone. And so for the first six months, we didn't tell anyone. Now, I mean, there was only, I. Probably 20 of us at the end of the six months.

And people knew I was there to help. help lead and, stuff like that. But it wasn't ever said formally. 'cause you know, Dave at the time was the, I think the formal CEO and every, at the beginning of every year we used to take a, a cruise. that year.

We, we went to, a resort instead, but we were sitting there at the circle, and that's where they announced to everybody, okay, this is Jeff's role. So part of the discussion there was like, well, let's make sure it works. Let's make sure at least we think we've got a good opportunity for it to work before we go and [00:13:00] disrupt, the entire company, and then six months later have to disrupt them again.

So there was a little bit of, can we see, but I think it, came down to, a couple things. One is decision making, the other's personalities, and from a personality point of view, I think there was a really good fit there with, Dave Roustem and I, I didn't know Roustem at at the time. Dave and Roustem are, quite intense. They can be quite intense. I am. Far less so my emotions are a lot more on the, the mellow side and, I think I act as a good shock absorber between the two. And so it was always a case of how do we problem solve and how do we lead as a group 'cause it wasn't a, I'm the CEO go do that. That can work in some companies, but I don't think that can work when you're coming into a company that has, has leaders. You, it has to be a case where you work together and lead. And then over time, and this is the tough part, Certainly something that I can see not working at other companies in [00:14:00] different circumstances you take the lead over the time you take the lead and then, over time, and that's probably three years, I'd say, I took the lead more and more especially as we got larger inside of the company, you know, Dave and Roustem We would call like Roustem for a time was, was brain and vision. Dave was heart and soul. And so Dave started focusing more with Sarah on things like the customer support side uh, Roustem focused more on the new technologies and where we were gonna go. And there was just sort of a natural, well, Jeff's gonna lead and Jeff's gonna lead the company, but we were still gonna all make sure that we're going in the same direction eventually, to the point where now again, as board members, they still have the opportunity to stay very much engaged, but they're not engaged in the day-to-day of the business.

But again, that took, you know, took 10 years and that was something that we all just sort of navigated into. It wasn't planned, it wasn't stated, but I think over time you need to have a single leader. You can't have three leaders for a decade. shouldn't say you can't. I think that'd be very difficult. 

Brett: So what, were you doing over the [00:15:00] first six months when you joined? Like every week? 

Jeff: We were building the app. was, a I believe it was the iOS app at the time that we were building. And, we'd spend a few days at Roustem's house, a few days at Dave's house or, my place We had a small group of us. We would come out to, California and just spend a week at a hotel and We were building the app. We were just focusing on that. Now, at the time, as I said, we were also, even though we had some formal customer support, at the end of every day, there was always tickets left over that, the, the group of us would make sure we're were cleared out And that gave us a great opportunity to. Talk, I mean, it's email, but talk directly to the customer. Find out what they like, find out what they don't like, find out what was working, find out was not working. And as a result of that, influenced the product. Now there was, financial side as well, which Sarah largely ran from the standpoint of making sure people were paid But there was also then slowly got into, okay, well let's actually start to plan the financial side, especially because as an app as opposed to a, like a subscription or things like [00:16:00] that. the big challenge with an app is when you have a renewal, a big chunk of, money comes in, and then after that it's sales.

People always look at it from a subscription point of view and say, oh, you want subscription so that you can make more money. No, I mean, we, you know, you think of our, of our individual, we make 2 99 a month, on the individual. We used to sell the app for 75 bucks. Like, if anything, we're probably making less on it, but.

That's consistent, right? I remember Sarah and I always talking about, and Dave as well, like the sleep at night factor. I'm not go hire that 21st, 22nd, 23rd person. If we don't know we can pay them in six months or a year like that weighed heavily on us, still weighs heavily on me. And so that was very different where, where then you start to look at it and say, okay, we've got some really cool ideas. Instead of putting them into the app, let's hold them back and then let's add them to the next version of the app because that would make it worthwhile for people to upgrade. It's the other thing that to me, always kind of stunk about having. app as opposed to a SA subscription. Like if we've got good [00:17:00] stuff, like I wanna give it to the, to our customers now, but then if we give all our good stuff to the customers now they'll say, well, why would, why would I upgrade?

But, you know, it's things like that that we started to think about a little more. Not that they didn't think about them before, but a little bit more. And then as time went on, we start, going even broader and looking at new opportunities to eventually where it was B2B. 

Brett: What year was that? 

Jeff: probably 2013, although 2014 was sort of the lightning bulb moment.

We had started to talk about some of the capabilities of B2B early, and now we weren't an app which means we didn't have a SaaS component, which means we couldn't have the concept of sharing. So we had actually put in this honestly, really, really poor way of sharing through Dropbox, where like people would need the same, Account password to get in and things like that. And it was just, it was terrible. And so we were starting to think of, of ways that we can enable some of this. But what I started to notice was, earlier on, in, the first couple of years, you'd have some companies that would buy copies of 1Password for all of their employees or Christmas to keep their employees safe. And then it started to change for some of the companies, not many, but some of the companies started to [00:18:00] buy copies of 1Password for all their employees to keep their business safe. And that was, the change. And so I remember I was at a conference, and I was just talking to, the folks next to me that were having dinner and they were talking to me about, you know, their use at their company, I think it was, they all individually used 1Password, but their company was thinking of getting Last pass because they have had a company account. all of the things that we had been talking about and thinking about just all came whoosh into me at a moment. and it was like, we need a SaaS app and we need a business app. And I went, I. Running off and the next morning I got Roustem at breakfast he got super excited. I don't think any of us went to the rest of the conference. We booked a, one of the conference rooms and all spent the weekend there talking about what we could build in this idea. And it was just the start of, what became 1Password for business. It was one of those lightning bulb moments where just everything we'd been you know, floating around your head just solidifies into a aha. I know what we need to do. 

Brett: One of the things that's interesting as you describe the path of [00:19:00] the company is it feels like a company where the opportunity unfolded as you sort of built it, the sort of traditional Silicon Valley company is you have some visionary founder and they explain this big idea about how the world is gonna change and then they marshal resources to make that happen over some period of time.

and I'm curious, like what's your reflection on that? 

Jeff: I mean, you're a hundred percent I say this with AI a lot, Where I personally, I think there's gonna be three phases, broadly speaking of AI you know, the first phase was sort of like, do you ai? Right. You know, and that, that really meant to you chat GPT and that we're in the second phase where every company is leveraging or looking how they can leverage ai both within their own products, within their own, tools, but also for their own use.

But it's still, we're thinking the way we do work today, and then we're just thinking of how AI can make that better, right? there's gonna be that third phase that I can't quite understand, um, where it will be completely different. for myself it's been less of, can I see that third [00:20:00] phase of, of security, not until we're kind of at phase two and a half.

So to your point, I think we can see far enough ahead, but it, it is by very much listening to the customer. whenever anyone talks to me, I'll just say that over and over again, your customer's telling you what's valuable and I, I mean customer, not user. the difference is, you know, if you come up with an idea and you go around to all of your family members or frankly people on the street and tell them, you've got this idea, you'll get the, that's awesome. More often than not, you go to those same people and you're like. Look at this thing I've got, will you buy it for a thousand bucks?

Uh, I don't need one today. and so there's a difference between kind of a cool idea true value. And so I think you need to have that broader idea, right? The broader idea. Even if that idea is something simple like, hey, we can keep people safe on the internet while actually making life easier for them, that can be considered, especially back in the early, you know, or mid two thousands.

And that like a pretty [00:21:00] revolutionary idea. Most people didn't know they even needed to stay safe. But the how you do it has to be rooted in something real. And that's where it's a case of you know, looking at your customers and trying to understand what your customers. Really are telling you it's the same reason why the Waymo looks like a car and not, you know, if we had started by just saying all vehicles will be self-driving it, probably would've looked completely different. you've gotta find a way to get there. And so I agree with you. This wasn't a, here's this a hundred billion dollars company I'm gonna build and I'm going to fundamentally, change humanity. I'd love to have that sort of idea and that, just wasn't me. but what I can do is, is I can listen to people, I can start to see the, the opportunities or the challenges they're facing, and most times it, it comes in the form of a challenge. Most times people aren't even realizing that they're asking for a solution. They're just complaining about something or, they're just, frustrated by something.

So I think if you look at it and you stay [00:22:00] focused on what's the core idea, and the core idea is how do we make, people and now businesses safe online, but in a way that still is a lot, still allows 'em to be productive. As long as we stay with that mission, with that vision, we can really listen at the, customer business or individual.

And that's the other thing. They're humans, right? I sort of Detest this difference between B2B and B2C. there's different needs without question in terms of the problems we're solving. But at the end, like, I'm not business Jeff 'cause I'm talking to you. And then if I go out and get a text from my wife, magically transform into, family, Jeff, I'm just Jeff or Shiner as everybody ever calls me. You know, like I'm just, I just am. And so we're all people and it's people that we're trying to make more productive while keeping them and their businesses secure. I would agree with you. I think the, the interesting side of it is for a lot of cases, if you don't have that magic vision of what the solution will be like, keep that vision of what you are trying to change, what fundamental [00:23:00] problem are you trying to change? 

Brett: How do you. Translate what you hear from customers into what you should do as a company. Because you could go back to the Henry Ford quote. If you ask people and they say faster horse, but also you obviously, you don't talk to 30 customers. They all say, well, I need this button and this thing and this thing, and then all of a sudden your product roadmap is created.

over the course of the company, what's that translation look like? 

Jeff: There's two sides of that. There's the what, and then there's the, the order. 'cause the order, the order's a little more challenging at times just because of, you want themes in that to emerge more than just features. But customers will by and large tell you solutions. You have to dig out of them the problem, and I think spending, you know, the, what was it, six and a half years in consulting in the US really helped me with two sides of that one. I used to say like, for every 21 features, the customers going to give you, there's gonna be seven that we're gonna say we're not gonna do seven that we'll absolutely do, and seven that we'll talk about how we're gonna do with them. [00:24:00] 'cause you can't do them all.

Right? And, and some of them just don't make sense. Some of them are so unique to that customer, that situation that they're not gonna have wide appeal. So the first thing you need to do is figure out you know, sorts of, of features slash problems, which are the ones that really fit in your, vision, which are the ones that are ours.

And you can't go chasing money. You can't sit there and say, well this large company really wants us to. build a video game on the side. you just have to be, be cautious there. So I think that that helped. But I think more importantly, customers will say, I want a blah, I want a report that does this, or I want a, a feature that does that. And you can build that, but you have to instead really try and understand what problem are they trying to solve. And there's two reasons for that. One, we found in a lot of cases what the customer's trying to solve, we could actually solve 80% of it out of the box just in a different way. and much of the time, certainly not all, but much of the time, that's completely fine to the customer.

Like they're, they're like, oh yeah, that's, what I, that's what I wanted. But [00:25:00] humans tend to talk in terms of solutions. And so I think the most important thing to do is to try and understand. What's the problem? Even, even if it's a complaint, like, I don't like how blah, blah, blah works. trying to understand why, and then trying to understand, well, is it the case that the customer is trying to do something that's very reasonable and other people are gonna wanna try and do it in the same way and now you need to find in your product?

How do you solve that problem? Or is the customer trying to do something in their way where, you know, we and our product philosophy are just fundamentally saying, Hey, well we're, we're solving that in a different way. It may, it may not be for them, but I'm not going to, try and, and, change the, the fundamentals of our approach.

So I think first of all, understanding that is, a, is a real challenge. And that's where, you know, we spend so much time, so much focus on customer support of, its, many different ways. You know, we still got hundreds of folks that are doing customer support. we've always. Tried to do it in our own groups.

We've got now the Dave Chan and the team that goes out and, works especially with the B2B customer. [00:26:00] So when we look to build something new, we try and get a bunch of customers involved as early as possible to sit there and say, will you help us form this feature, form this product? otherwise we're making it up as we go, thinking we know how to solve a problem that's really theirs. And so if we can get, you know, a bunch of customers, especially business customers now coming in and, and helping form that, feature, boy, that a, gives you advocates from day one b gives you real stories as to what problems it solves. And see it just helps you solve you know, in a real way.

And so I think it's all about trying to understand the problem behind it. And I remember I was at University of, Western in, London, Ontario, and was taking q and a from, it was like a, TechX, I think it was called. And it's, it is like their tech accelerator group and The one, university student and she was asking like, how do you come up with a billion dollar idea? And I said, well, you don't, I said, I don't know how to come up with a billion dollar idea, but you look for the billion dollar problem. And then you try and figure out if you're the one to, solve that problem. And [00:27:00] that's how we approach it, is there's going to be a problem out there, and that's gonna be worth however you want to think of it, in terms of dollars or whatever. It's worth a lot of value and somebody's gonna gain that value by solving that problem.

Then you have to think, are we the ones that are right to solve that problem? That's actually what led to even, extended access management to our newest set of, products now where we looked at it and we said, this is a real problem, but we also said it's a problem in large part because.

The employees are trying to be productive. The business needs to keep them secure. Hey, that's what we do. Right? And then you have to really think about it, and that's where priorities come into play, where you start to look at it and you say, where does it fit in our roadmap? what's our roadmap themes?

Are we focusing on, you know, different segments? Are we focusing on different plans? And that's where I think getting enough of them together that you're not just solving the one problem, but you're solving that class of problems for the customer. Because usually if they have one problem, they have a class.

So unless that class fits directly into [00:28:00] EPM, then we need to look at and building enough of it that we can, we can help solve a broader problem. 

Brett: When you think about prioritization, do you think about the economic opportunity tied to this set of features or that set of features or this set of problems?

Jeff: I do. Yeah. I mean, I think you have to, It's only one of the things that goes into there. So again, I, I look at it first and foremost and I say, do we have an unfair advantage? are, are we gonna be in a position where it makes sense for us, the company 1Password to tackle this problem? even if there's a huge economic opportunity?

And it's, you know, I I say it kind of silly inside. we're not here to build a game, right? we're here to make people productive and keep people and businesses safe. That's what we do. So if there's a huge economic opportunity that's outside of it, that's, that's just not for us. I think if we don't stay focused in that way, we will eventually, struggle and strain. but when you do look at an opportunity, you do have to look at the economics of it, and you have to sit there and say. Are we going to be able to put a real [00:29:00] solid investment in here and really make it a great product? We had that discussion, fairly early on.

So we actually had a separate product called NOx, and NOx was a file volt. and this was early on and we wanted both, NOx and 1Password to continue and, and that, but we got overwhelmed with all of the feature requests and all of the opportunity with, you know, 1Password, the password manager at the time, and we couldn't do it at Justice to NOx.

And so we just said we've gotta put nos aside. I'm not gonna allow us to have, have a small number of people make aeh app I want the app to be great. And so when we look at it from an opportunity, from a financial opportunity, sure. We're, now big enough, we're gonna have the finance people and stuff look at it from true, true finance.

But I, I'm gonna look at it from a standpoint of I wanna build something that I can build. Great. And that means I need to be able to justify putting the spend in, putting the people there, putting the focus on [00:30:00] so that we can make it great. And I don't want to just build parts that are gonna be okay and now they may start off okay. You know, again, it's all gonna start off somewhere. When we launched 1Password for Business back in 2016, I mean, it was, we called it 1Password for Teams, and it was like, really maybe 1Password for bowling leagues. Like, it was, you know, but it was, it was V one. You just keep iterating, keep iterating. that's fine. But the goal's gotta be, gotta be great. 

Brett: Why do you think that's so important? I mean, said differently. That's obviously the thread for anybody that's used your products is that they are great, but if you look at most enterprise software companies that are worth more than a hundred billion dollars, no one would say that their products are great. do you, do you ever think about that?

Jeff: I do, I mean there, there, there's some that I really enjoy. slack would be one that I, that I really enjoy. slack was the one that just seemed to, again, care about the user. and there it was little things at the time, you know, even like expanding a Twitter link. I remember it was one, I'm sure they all do now, but, you know, at, at the time. And so there was, little things. And if you [00:31:00] remember going to their website, they had those moments of delight in their website and things like that, that matters to humans.

Especially I think in security, because security can be scary. at best you're thinking the security, even if it's not scary, is gonna just hold me back. It's just gonna make my life more miserable, right? Like, that's, been our experience with security. So the more we can make it easy to use and friendly and really focus on the human at the end. Then the more likely we are to actually be used now at an individual or a family level, that's gonna be important. 'cause that's how you're obviously, you know, gonna make a sale. But at a business level, sure, you can have somebody sitting there and forcing it on you. But imagine that software that, your CISO comes up to you and says, Hey, you have to use this.

And a month later like, this is awesome. everybody wins. 

Brett: I want you to go back and talk more about. How you actually built the B2B product and got that into product market fit. You shared a couple bits of the story, but it began with, you were at this conference, you were talking to somebody and it sort of occurred to you that you were really well set up [00:32:00] to build a business product.

 What was the 90 days that happened after the conference?

Jeff: it was, yes, very, very much of duck on water. Yeah. Paddling furiously underneath. so it was, I'm gonna say a week after, we got group of about eight of us into the basement office that we had at the time, and the big whiteboard there.

And we spent the next few days refining, refining our solution that we were Oh, so tremendously proud. This thing was so secure. It had service tokens, it had all this type of stuff. It was gonna be so secure. And then what we did was we actually went and we, came, actually came up to California and, talked to a few folks that we knew who were high up in, CISO type positions and that, or security positions at, companies.

And they all told us how crap it was. Nobody's ever gonna use this. It's unusable. you get a bunch of security geeks together and we're gonna go and, sometimes make the biggest mistake of all, which is like, how secure can we make this? Right?

Brett: their critique was, it was not secure

Jeff: no, no. Their critique was nobody's going to use it [00:33:00] because it was way too secure. you know, to the point of we didn't have a web interface because of things you can't do on the web to, it was just, we'd gone overboard. It, it was a fun exercise, but we'd gone overboard. But there was, the nuggets of it they loved, they're like, look, this thing's available.

We're buying it in a minute, but it's got a, you know, it's, it's got to have, have these, these things.

Brett: Did 

you think about, when you were thinking about the early customer base, did you think about the difference between, you know, a company with 30,000 employees talking to their CISO versus a small business with 30 employees, and who were you building for, or you didn't think about it in that context?

Jeff: Somewhat like we knew the large companies. Now our goal is you gotta build it for the large companies. You gotta build it for, maybe not the, the world's most complicated customers, but the every company, right? the every company that's out there, 5,000, 10,000, a hundred thousand people. But it's a journey, and then you need to understand what they need versus what a company of 2000 needs [00:34:00] versus a company of 200, which is very different from a company of 20. and you need to understand at each spot. But if you don't focus there and say like, what would that company need? You're not gonna put the right fundamentals in place.

And then, then you need to start thinking of it in terms of releases and tiers. Like we've got, we still have 1Password for teams and we have 1Password for business. And then, you know, the enterprises will, need it. And now we're doing the exact same thing with the full extended access management, where you look at it and you say, what do companies of, different sizes need? But your fundamentals have to be there. They're all solving the same problem. You know, with, password management. It's, three things, only one of which we had with the consumer. So at as broadest, it's one, humans need a way to stop using fluffy cat, that's whether you're an individual or whether you're a business, like the risks are there for you as a person, you as a family, you as a business.

And that's still where the vast majority of breaches start is, is credentials. The second thing that a business needs is they need, the teaming ability, right? We didn't have a SaaS app at the time. We were, we were just an app. So we [00:35:00] needed to build the whole SaaS solution, and that's, where we had focused, our attentions.

And so you can do things like sharing, you can do things like, access control and reporting and all of those capabilities, right? And then we needed, from a, from a business size, you need sort of the, you need to solve the business problems along with the end human problems, which means you need all of the abilities that the CISOs need to understand risk, profiles and things like that.

When you think of a, 20 person company, they all need the first one. They all need the second one. Sure. They're, sharing may be far simpler, it may be, everybody gets, this vault, here's the two people that have access to the social vault. I remember at our company for a long time, there was.

You know, three people that ha had access to the company bank account, those are the three people you need to, share with and stuff like that. Those problems exist. They don't exist at the same level. You may not be using, you know, an IDP at that level and you're not doing reporting, so you're not doing provisioning.

You still need to make sure when somebody leaves your company you remove their access. So it's degrees, which turns into [00:36:00] features to be sure, but it's still the same fundamental problem. I would say that third problem of, compliance and things like that are the ones that the small companies just, it's not, that they don't care about, they haven't grown large enough yet to care about.

They're like, Hey, I may not be around, in, a year. I'm not gonna worry about whether I'm making this compliance. So there's, is that third one that, that we at the time and back in 2016, had sort of purposely put later on 'cause we still hadn't built up the capabilities yet to satisfy the larger companies in 2016. but. From a fundamentals point of view, your, your architecture and your infrastructure is, going to largely stay the same. We wanted to build it to scale. so yeah, so we, went in the basement. We then went to California, which was best trip ever because it, it just a demonstrated that what we were trying to, accomplish was spot on. we had just done the typical mistake of pendulum swinging too far. I went back, pendulum swinging back a little bit the other way. Went, talked to those folks again. when we were comfortable that we had it largely right. we started building and then we just, it was [00:37:00] again, building the SaaS app, hiring a number of people. you talked earlier about the financial side. you know, we were bootstrapped, this was our money. We were like, Hey, we've gotta go and hire a bunch of people that no one can support, infrastructure. 'cause I. You're an app. We didn't have an infrastructure before, or very little infrastructure, right?

We had to hire a bunch of people to help build this new app So there was a, time when, you know, we looked at it and we said like, yeah, we, we believe in this. But there's also that time when you've just gotta say, we're jumping in both feet and we're gonna go after that.

So that's what we did. We jumped in with both feet and took us about, I wanna say about a year to where we got it, to where we had our first beta. And I'll, I'll tell you a, a fun story that I share at our company every once in a while. You know, it was, somewhere around September, October of 2015, we decided we'd have a, free beta for the next few months. And, you know, it was everybody thought it was a cool idea. Well, the reason we had a free beta is like. We hadn't built any of the billing code. That wasn't important, you know, Billing's, like the last thing you wanna think about, you want to build the app, you wanna make sure the app is good first before you worry [00:38:00] about billing.

Brett: So who were like the first five customers, these beta customers for the B2B product? And what was like, what did the product look and feel like at that time?

Jeff: what we had started, because we built the SAS app, we had built it for quote unquote everyone. What? By, by that, what I meant was we had built it for individuals, families as well as businesses. 'cause it, there really wasn't. A huge difference between what a family needs and what a business needs.

Again, other than in degrees, if you think of it, you know, they each need a copy of 1Password, so they don't have fluffy cat you're gonna share passwords at your family. Right. Even if it's, you know, your wifi and security codes or things like that. Or maybe back then Netflix, and stuff like that. and so we had built it and we'd actually had the families one go out first as we continued to build some of the capabilities for business. So that helped us understand that, you know, the product would stand up. And again, all of that, we, we always dog food it ourselves. We always do. You know, as soon as we can get in. I'm not user number one and I'm still upset about that. I think Tim is who at the time ran our it, 'cause he set up the, the [00:39:00] database, but it's, use it yourself and then onboard, I think we did families and then eventually, companies who by and large had, had been. waiting for it.

So these were back then, so we still didn't have any marketing folks or go to market folks. It was people who had gone from being individual users saying, look, as soon as you have it ready, let me know and we'll try it out. And, and they did. They tried it out, in teams, in their companies or in small groups or that, because they were just, they'd been waiting for this.

They, they needed it from a business point of view and they were already, loyal one pass customers. And did It immediately. Resonate in work.

it did. again, I would say back at the time, we didn't have all of the capabilities that a lot of the companies needed, which was just fair.

We just flat out didn't, and it was, V one or V 0.9 or whatever you want to call it. So the adoption of that wasn't immediate for a lot of those companies. but yeah, it, Again, I would say it, resonated even before we had it out there, in terms of as a need. And then [00:40:00] it's a matter of, just building the features that were truly needed, and that, that was the next few years was just, what did our company need as our company grew?

I'm trying to remember how big our company was back then. Probably, I don't know, maybe 50 people. I, I'll be wrong, but something like that. and so what does our company need then? What does a company of 500 need? What does a company of a thousand need and, and,

Brett: Did you think about. Other products in the market and competition and things like that, or it was never part of the way that you thought about building products.

Jeff: I always look at competition in two ways. One, you don't want to, Fight the competition's battle. I don't have a good way of saying it. In other words, if, if the competition adds a good feature, that's legitimately a good feature, you look at it and you say, is that something that, we should do? you see that everywhere, right? Like you look at it and you say like, if they're tackling this problem right, whatever, problem is, should we tackle that problem, even in our own way, But a lot of the times, a lot of the features that are being added aren't that useful.

They're flashy or things like that. And so I think if you, if you watch the competition from a standpoint [00:41:00] of, trying to keep up with them in that way, you're, playing their game, not your game. What is it about us that we make great?

Well, what makes us great is our focus on the usability, our focus on the human that's using it, not necessarily every report that comes out. And so when we're gonna prioritize it back then, because again, you want everything, not everything, but you wanna do 10 times as much as you're doing all at once and you can't. so our priority was, gonna be instead of adding a ton of, just, reports or things that we're gonna try and compete directly there, let's just make sure that the things we. Are known for, you know, make those stronger and then start making our weaknesses invisible at the beginning.

It's the same thing I tell people just from an individual point of view, right? Like, if you're going after whatever the next role or the next job, don't try and make your weaknesses, your strengths. Like, you see that all, the time where it's like, this person over here is a great public speaker and I'm, terrible at public speaking.

And they'll say like, so I'm gonna take all of these lessons and become a great public speaker. [00:42:00] Well, how about you take enough lessons that you, you become an okay public speaker, that people don't look at it as a negative and then the things where you're good at push on them. Yeah, exactly. And so it, it, it's the same thing so early on you have to really, you know, really focus there, but then your competition continues to change over time. you know, as we evolved beyond password management into broader, I. Zm, we have to look at it and say, where's the competition now? And, what are we, battling against? And that's not even just companies. It's what problems are we trying to solve? So for instance, as we, as we moved from password management, you know, back in even five, six, but certainly seven, eight years ago, there wasn't really the same sort of problems that we have today.

Not problems, I'd say, problem slash opportunities that we as, humans have today in terms of, now SaaS apps are everywhere, right? It, I say someone jokingly, software used to be sold on golf courses, right? You'd get a salesperson, get an executive, six months later you're using Lotus Notes. That's how it worked.

Nobody quite [00:43:00] sure how in between that works. Now SaaS, you, you go to a conference, you go anywhere and it's like, oh, I heard such and such is good, I remember Figma coming into 1Password where our, design team had used Figma. And so I, just assumed, uh, that's for the design people, right?

I, I can't draw Stickman. Well then Matt Davey, who's, you know, one of our, lead designers, he had a a Fig Jam. if you're not familiar with the Fig Jam, it's, it's kind of like the, you know, everybody get, gets their cute little sticky notes, but virtual sticky notes I kid you not, two weeks later, every team in our company was doing a fig jam. It just blew off like us. and it's, that sort of thing that that's how software gets in. And we didn't even, you know, for the most part it didn't know Fig Figma was even in the company. 'cause it's just a team using it.

So those are the sorts of, challenges that, people face now is it's personal devices. You know, you think of it 10 years ago, a phone was. you know, first of all, it was probably, well, maybe 15 years ago, it was a Blackberry Right. You know, and, things like that. And then 2005 started to change, and now, now a [00:44:00] phone, like you try and convince my 24-year-old son that the phone isn't, a virtual version of himself. you know, you'll fail. And so now people want to use Sure. Company devices, but also personal devices. Sure. The enterprise apps that are deployed and, and, probably behind, uh, your typical SSO, but also all of these SaaS apps that come in. And the businesses have gone from being really against that to now where it's like, Hey, what's most important for almost any business?

We have to succeed. We have to grow. How do you do that? You'd be productive. Well, how do you be productive? You let your employees be productive. I always say, say it this way, at the end of every year, almost every employee gets a performance evaluation. How many of those employees get a performance evaluation based on, did you only use company devices?

Did you only use company apps? Right. Did you, no. It's like, did you make your, your results, whatever it is in marketing and go to market and design and finance, everyone's gonna have different ones, but it's all based on their own. We can [00:45:00] make the employees productive. The company can be, productive, but we still need to keep the company safe. And so it's, it's now that same problem that we had back when I started, you know, in, in, in 2012 of productivity and security coming together. And how do we have them not be at odds? But the problem space is different now. The problem space is how do we do that with devices and apps and how do we allow you as an individual to choose what apps or largely choose what apps are gonna make you and your team successful largely use your devices that make sense, which is probably your company issued, device during the workday. But in the evenings or on the weekends or things like that, it's probably your personal device if you, you know, you get a Slack or whatever that comes in, you have to address. And so how do we make the, the human productive and how do we give the tools to the business that allows them to allow their human, you know, their employees to be productive, but also to keep the business safe.

And that's only gonna get worse, with ai. [00:46:00] Because one of the cool things to me about the way we're going with AI is you're gonna have your little AI buddy, right, your AI paperclip for those who remember clipy, you know, who's, who's gonna help you with everything you do. But you're gonna have to give that AI a ton of power, and that's gonna be scary. Some of that power is gonna be business power. In other words, you're gonna give them access to, you know, so you might have a, Salesforce and, and then they're gonna have their AI agent running to say if your pacing is on target.

But it might be also something where it's like, Hey, you just book me my travel. And not only is it going to have access to the company stuff, but it's gonna have your passport and all of your other information. And so how do we do that in a way that allows us as, as individuals, to keep our information that we need to keep private, private, our information secure, but again, productivity.

So that's the part that, privacy and security. Such a big opportunity that we can just navigate our way into what parts of that we solve best? 

Brett: as you sort of started to talk about this, the second chapter of the [00:47:00] company when you went for, when you built teams and then you built, the business product. You haven't talked that much about how you thought about go to market. at what point did different traditional go-to-market functions start to get built in?

In what order? 

Jeff: I mean, it came through hard work. We were fortunate. We did have good, product market fit and because of that, a lot of organic, inbound from, customers. And so for the first, you know, 2016 and in 2018, we, formally launched 1Password for business. 'cause we had a lot more of the capabilities obviously, you know, continue to build seven years later, but. that's when we started to get a lot more, I'd say, real businesses, really entering. And with that, it, it was still half of us are customer support, half of us were engineers, you know, build a good product, support our customers. 

Brett: were most of the customers, most of the business customers, did they start as individual users of 1Password at home and in their family and brought it to work, or it wasn't that elegant. They'd actually just, a friend of theirs was a leading it at a company and really liked 1Password, and they adopted it in a more traditional fashion. 

Jeff: if a company came in, [00:48:00] how would they sign up? They would go to the web, they would sign up for a free trial and they put in a credit card.

I kid you not, it doesn't matter. The size of the company is some very large companies. that would do that. and so that was considered a business, like an individual who, worked at a company, wasn't a business, it was an actual business. So when we were still getting a ton of individuals, still getting a ton of families, but we were getting a, a lot of, employees, like a lot of people using it because their company signed up in most cases.

In the vast majority of those cases, there was. A person or people at that company that used us as, individuals. And that was the, the flywheel for that company to get it. So in terms of the actual sum of businesses we got, the businesses by and large came because there's people of influence at that company that were using 1Password at that time.

We, again, we weren't doing marketing outside of our website and things like that. So we started to see two things that started to happen. One, I remember Russum and I started to play with marketing and I do mean play. So we, went into, Google Ad words and we were like, you know, what ads, what words should we bid on? that was sort of [00:49:00] the very start of, of marketing from a go to market point of view. our customer support team started to have group within them that would help the, the businesses. 'cause we are now starting to get enough businesses, probably at this point in time, 10,000, I mean, maybe even 20,000 coming.

Yeah, maybe, maybe even 20,000, something like that Many of them small, but now growing in size as well as we, as we started to have the, the bigger capabilities. And we were just at the point now where some of them started to need, some legal things.

And so we had an outside counsel that was helping us at the time who we eventually hired in house. And we had a team from customer support of folks who would actually talk to the, to, to these businesses and maybe they needed an MSA, we started to slowly take, invoice pricing and things like that.

And for some of the larger deals, negotiate on pricing. 'cause again, it was all just, you know, go to the website. So that, just started to obviously force the need for, you know, a sales [00:50:00] team, as we called it. At the time it was all inbound, it was all organic. We didn't have any outbound or things like that.

Mm-hmm. And then over the next couple of years, it started to evolve a little bit. I actually hired company, um. friend of mine had started a, uh, digital marketing agency. that's what Rosetta was technically a digital marketing agency. he did the, um, like the bidding, the SEO and the SEM.

And so I had hired him to come and do a review of our website from an SEO point of view. And then, then they stayed on and ran some of our, SEM for a while. It was very nascent. It was very small, but it was just the start of it. And then we, started to try and mature our, our go-to market team a little bit, right?

Like I said, we brought the, the council in-house and we, we separated that, that group, I think it was six, we were getting some in a couple of cases, some very big companies, you know, that, I and a couple others would go and, and visit as part of the sales cycle.

And that's when it occurred to me like, we need to grow. These orgs, but I don't know how to do that. Like, well, I know, I know how to do it from one standpoint. And that is you [00:51:00] get in good leaders who know how to do it. What I didn't know how to do is attract world class leaders in, areas outside of, what 1Password was traditionally known for, especially because we had been so private you know, we were still bootstrapped, still, you know, running independently that nobody knew were we successful, were we not successful?

Were we growing, were we, broke? Like nobody had a clue. And you're not gonna come to to 1Password especially to come build a go to market or a marketing. You're not even gonna look our way without some reason. And so that led in the sort of the middle of 2019 for me to, actually bluntly go to Arun and say, okay, let's talk.

So I had built relationships with a ton of VCs over the years, More to the point VCs had come and build relationships than me. And, and they're smart people. I'm more than happy to, to listen to anyone. but I always said sort of the same con look, I, I dunno what we do with your money. we've got our own money.

Just, we were smart with our, our money and we'd built it up from nothing and, had remained a business and it remained profitable. And so there [00:52:00] wasn't a need. Well now there was a need and the need wasn't specifically money, but the need was what we could do. And, and that's where the first round of, funding came from was how do we announce ourselves to the world per se, so that I can hire world class talent and world class leaders. and that's what we did. So at the end of 2019, we announced the, you know, the first ever funding round was the 200 million round with Excel. and in January I hired Jeannie as my, uh, CFO, now COO. And she was my first executive hire. She was actually introduced to us Through Excel, well through David Fogo, who, I had met through Excel and then, you know, over the next few years, hired, the rest of the, the C-suite.

And, also I called 2020 year growing and growing up. So growing. We had grown from like 176 people, I wanna say we had at the end of 2019 too, you know, now the 1400, but also maturing, right? Build a real go-to market team, build a good marketing team, do proper financing and, things like that. as well as [00:53:00] continuing to make sure we're product led and, and we're growing, customer support org and we're growing our engineering org at the same time. 

Brett: You only just hinted at this, but what was the thinking behind choosing to be bootstrapped for 15 ish years? And what were the biggest positives of making that decision that maybe are only clear looking in the rear view.

Jeff: Yeah. So, you know, Dave Alia were the, were the ones that that started it and they started it, like I said, you know, in, in the proverbial basement and it grew over time. So I don't know that they had a plan at the earliest of stages to stay bootstrapped as much as it just sort of organically happened that way.

Brett: Which is interesting 'cause so much of the company's origin feels like it just sort of flowed out of them. It wasn't we're gonna go build a company. It sort of had this step by step sort of nature. 

Jeff: I think that's one of the benefits of [00:54:00] staying bootstrapped. So, you know, for instance, when I came in, in, 2012, first couple of years it was very much of just, you know, the first year in particular was just trying to figure out what were the opportunities and, getting us into, in things like localization and translation and, do a better Android app and a Windows app.

So we had a more broader suite and that gave us the opportunity to look at B2B when it, when it started to come about. But when I look at it from a bootstrapping point of view, the challenge there becomes how do you grab and run after. Every opportunity. Your vision doesn't have to be super set. And I think that's the side of it, that, when I look at it from a bootstrapping point of view, if we had gone funding, I, I could be wrong. 'cause again, we didn't do funding early on, but my perception of it is, they wanna know where you're going.

They want to know when you'll get there. They want to know what that opportunity is as opposed to what we call our North Star. and our North Star is, what we as a company do, right? It's that combination of productivity and [00:55:00] security. You know, bringing that, convenience and security together for humans in a way that allows humans to be productive in businesses or their families to be safe.

That's our north star, that's where we're going at. And instead of saying like in five years and in 10 years, the same thing with my career. I get, you know, if you'd asked me back when I was younger, what do you wanna do in five years? I dunno. You know, I, I can tell you what I'd want next. and it's that same sort of thing.

And then it's, jumping after each opportunity requires a degree of, flexibility and a degree of just, I don't wanna say bravery, but I don't have a better word for it. Gumption, what, whatever word you wanna use when I looked at it from a, B2B point of view, it would be a great example.

Like I said, it was quite literally, you know, that night at dinner that everything just clicked. And the next morning. We were in the room at that hotel, on the whiteboard, drawing out what we would need. We didn't think about how we were gonna explain it to,

to VCs, whether or not we, you know, needed to get permission or any of that.

[00:56:00] We just said, we believe in this done like that. that's the, that's the jump after it. because we know it's in our North Star direction. Again, it's not, ooh, it'd be really cool if we made this other thing e even if that other thing is, is super exciting.

Like, that's just, like, that's what our company is for, . And so this was squarely in there, it, it was an obvious extension in some ways of what we were doing. But again, taking us from an app, taking us from, individuals really only into.

We have to build a SaaS app, we've gotta build all of this B2B, like it was a huge jump and a huge risk from that perspective that we didn't have to convince anybody other than, really, the group of, five of us that this made sense for us to do. And even there, it wasn't an economic decision other than do we have enough money, you know, to fund this so that we can, we can give it a try.

So I would say that the benefits are that flexibility. Now, on the opposite side. what if we didn't have enough money to make it happen, Or what if it took three years longer than we had planned? Or things [00:57:00] like that. So there's, definitely downsides, but I would say if you've got a great vision, a great North Star, but you don't, you don't know exactly where that trajectory is gonna bring you, you need that flexibility because otherwise what you're thinking today.

Might be useful in five years, may not be useful in five years. The, the next five years are gonna bring us tremendous change. So how do I set that direction, that path, that fundamental vision or problem to solve and stay flexible and not have to spend all of my time trying to convince others that, I should be able to do this.

That's, that's the benefit. 

Brett: Do you look back and you can clearly see that at certain points there would have been benefits if you chose to raise capital 

Jeff: hindsight being, 2020, I would've raised capital earlier. you can get to a point where you're proud of things. You should no longer be proud of maybe said a better way the things that you're proud of can inhibit you. And so, you know, once you've been bootstrapped for [00:58:00] 10 years and everybody's like, wow, you've grown this, great company, all bootstrapped, how impressive is that, that becomes becomes your identity.

It becomes a blocker when it's like, does that mean I'm less successful if I take funding? you just have to try and ignore those and like ignore those thoughts in your own head. if we had had marketing and go-to market and like real marketing, real go-to market, if we had been more mature earlier, that would've helped us because in some ways we're a, company that's been around for, you know, 19 years in others. We've been around for four now going on five years and. the changes over the last four or five years have been dramatic, but in every aspect. that's tough to keep your focus. Right? so if we had, had an extra couple of years then go to market, would've been ahead by a couple of years and marketing would've been ahead, you know, it's easy to look back and say that that's true.

But I, I think in hindsight, I waited too long for that. But I [00:59:00] do think going B2B would've been very challenging in an environment where we had had funding based on a consumer experience. You could certainly see the opposite, right? Like, if, if we were B2B, if any company's B2B and says, Hey, we wanna go after to the consumers, their investors will be like, no, you're not. 

Brett: when you look back in the 13 years that you've been at the company, what do you think are the most skillful things that you've done

Jeff: focus on the, human. we really do care about the experience that, people have with the app. that can be something that can be easily lost, especially as you grow and change and move into B2B and things like that. You could start to think, well, businesses don't care about that.

The consumers do. we care about that. And to the point where at times we've had to defend that not greatly. even with, you know, VCs and stuff like that is like, are are we spending too much time in focus? I think everybody understands now that's gonna be our advantage. That's going to be the [01:00:00] reason why people choose us.

But I would say that that focus and maintaining that focus is, really been the reason that we've been successful. 

Brett: This sort of simple idea of being customer centric or building delightful software, how do you keep that alive all of the time now that you're at scale? Other than talking about it?

Jeff: at some level, it all comes down to people. So I would look at, Even how I got hired as an example. So that was set by Dave, Sarah, Roustem and Natalia right? You know, we were gonna listen to our customers, we're gonna build a usable app. Like that was what really mattered to them. And it's what a attracted me to the company in, part.

And, so they saw that in me and they're like, okay, like, you know, Jeff can be a shepherd of that as well, as opposed to having to train, you know, somebody that this matters. So you have to look for that in, in people now in certain roles, to be clear, right? We have to look at that from a design point of view.

You have to look at that from a product point of view. You have to look at that from your most senior execs, that they're, they're gonna understand the value because you can [01:01:00] have plaques on every wall or whatever, whatever you want. You know, none of that matters, right? People are going to, to lead, especially as you grow and you give, more people responsibility for things.

So it does come down to are the people in the foremost positions. at a minimum aware of and supportive of that as your, unfair advantage. if you can do that, then it's very easy to just gain the momentum and, say, yep, we're gonna continue to do that. it's part of the reason why, you know, when we look at collides, so for instance, collides company that we acquired last year, and and Jason, who's, the founder, had a very similar philosophy.

It's part of the reason why that made sense to us. It wasn't just buying a technology. Now you can buy technology for technology's sake, but then you're gonna have to look at the UX side of it and, and redo it. But that was, that was really important to him. And again, we, I looked at his company and it all fit and everything, but also he, as a person, I'm like, he's gonna help us maintain that.

That matters to him. It was personal to him. And he's gonna be in a, position of influence on the product side [01:02:00] here, and he's gonna make sure that continues. I think that's the, the only real way you have to do all of the other things. You have to tell everybody. It's important. You have to, be able to demonstrate that But it's gonna come down to are you hiring people that really care?

Brett: You sort of shared the origin story of how you kicked off the whole process to go B2B, and it seems like one of those kind of pivotal moments or pivotal stories in the company's life. Are there any other sort of, moments like that, that come to mind that you think are like some of the input drivers of what's made the company so wonderful?

Jeff: oddly enough, when we went for the round of funding. it's a weird thing to say, when you ended your sentence with that made the company so wonderful. because that's not certainly how I would've thought of funding. Right. but the funding round was, such a pivotal moment. and there's two things I would say that were really pivotal about it. One was, again, Dave, Sara, Natalia and I, it was our company before that, like it was, we made the decisions again, we had the broader team and [01:03:00] stuff like that, and the company was getting larger, but it was still very much, nobody had to decide but us if we wanted to do something.

And so giving that up. Even in some way, we made sure we retained ownership and we didn't give up very much to the company and all of those sorts of, but it doesn't matter. It's still just, it felt It felt very much like we were giving some sense of control to this other entity that wasn't us. that we had so many heart to hearts internally between the, five of us about the pros and cons. It was a huge emotional, exercise for us to understand 

Brett: What was that conversation like? 

Jeff: it was, why would we do this? It was like, what do we think we will gain? is really what it came down to. And then it was, what do we think we will lose? How do we technically, or legally, or whatever the word is, prevent ourselves from losing it.

those were the bulk of the discussions. And then every once in a while we'd have the real discussion. How do we feel? And that was the, those were [01:04:00] the raw, we're feeling excitement, but we're also feeling fear. Like it was, it wasn't ignore all of the data. It was just how do we feel?

And that was, those were the discussions we needed to have. And we were close enough as friends to have, and there wasn't a reason for any of our feelings. We recognized that there wasn't a, the concerns were so easily mitigated, especially, we were in a good position. We were able to sit there and say like, we're not giving up there's no magic voting rights, no magic dates we have to hit.

Right? I mean, they just, you know, wanted us to, continue to grow and, and, and all those sorts of things. So, so the emotions were just. I don't wanna say unfounded, like emotions are always founded, but it was, it was something we just had to be honest with each other about and admit that this was yet another case of, somewhat conceptually similar to the B2B side of like, this is an exciting opportunity we're scared because we have to take a big risk.

And what have we always done when we've looked at the big risks, we've looked at it and we said, [01:05:00] let's, you know, understand our emotion. Let's, recognize that it's there, but this is the right thing to do. Let's take this risk. And it was the same thing with funding because the reason we were doing it was to, to go and hire, people that could grow world class.

Organizations for us that we couldn't get another way. And so once we started to look at, at again the pros and cons, how do you, how do you really mitigate the cons so that they weren't a real concern? Then it was about just facing your emotions. And anytime you do that, you're like, okay, like it's okay to be scared.

that's how we move the company forward. that's where the five of us being friends makes all of the difference in the world. We can have the, have those discussions. That's why even when I, look at our C-suite now, that's why we try and get together so often as people, you need to be friends.

Yeah. You may not be friends on a, you know, some of us are, some of us aren't. But you know, on a, on go for a whatever basketball game. But you, you need to, to know each other as people because you need to make those decisions. 

Brett: Maybe just to wrap up, we'll end with the question we always do, which is for you personally, who's the person that's had the biggest impact [01:06:00] on you in this case as a CEO

Jeff: many years ago I was a, developer at IBM and, Mike Poland was my, boss and our team lead had left the company. And so I went to Mike Poland and I said to him, I wanna be the team lead. And I laid out my reasons for being the team lead. He says to me, okay, but I'm not gonna tell anyone.

 I went home and thought, what a jerk. And so six months later, as the team lead and I, and I finally asked him like, what, what was that all about? And he goes, three people came to me that day and I told him all the same thing. He goes, A leader leads, it's not, yes, having the title and everything can help, but a leader leads and so who is going to actually lead and I led, and that to me is, now, I wouldn't do that.

I've never done that to anyone. I, you know, I'm not sure that, that, was necessarily the best way, but in like, it was the lesson I needed to hear. and so, you know, from a CEO point of view, and that was, that was a team lead of a, of a, of, of a small team with a ton of support and everything, but it's still leaders lead.

And that doesn't mean [01:07:00] that you're gonna go out every type of leader can be different. You have the type of leaders, they're the, I'm gonna march this way and, and a hundred miles an hour. I'm only gonna hire people that, that are going to be behind me and not challenge me, but also walk a hundred miles an hour.

And that could work. There's the type of leader that are gonna be a lot more collaborative and things like that. But you have to lead, you know, the responsibility is ultimately yours. It doesn't matter. Like who makes a decision when you support that decision, that your decision.

And, you have to take it. So I, you know, I would say being a CEO is, is, it's very lonely. it's tough, it's rewarding, it's a bunch of things, but lead and lead doesn't mean on your own, but it does mean take all that responsibility, put it on your shoulders, and then, you know, make sure that you've got your teams back so that it's always, Yeah, you're, you're with them on those decisions. But that was, that was many years ago, and I will, I will probably die thinking about that.

Brett: Nice. Great place to end. Thank you so much for joining.

Jeff: Yeah, it's been fun.