Founder Stories

Hi everyone, I'm Mia Wang. I'm a member of Cloudflare's Corporate Strategy and M&A team and today I have with me Darren Remmington who is our Director of Product Strategy Innovation and the segment is called Founder Stories, Why We Joined Cloudflare and it's meant to highlight the experiences of some folks who've joined Cloudflare through somewhat non -traditional channels and in this case Darren joined us by way of ST Systems, a company he co-founded and was then acquired by Cloudflare back in January of this year. So thanks for joining us Darren. Thank you, thank you. I'd love to dig in a little bit on you know what your experiences were like leading up to coming to Cloudflare and what your first few months here have been like but before you get there do you mind just telling us a little bit about your background and I know you've had a pretty interesting career. I would love to hear more about that. Well the short version is I think that I started messing with computers in high school like sophomore year which is way back before the Apple and before the IBM PC. It was a long time. By the time I left high school I was doing, I had a job of writing programs for different people, contract programming and I did that in college as well but that wasn't my track. I wasn't planning on going into technology or computers. I was actually on a medical track which is most of what my family does and continues to do but partway through that process I realized that I really did like computers a lot better than sick people unfortunately for my mother at least. So I switched. I started a computer company with just me and that was the first of many I think and I didn't sold that one for a ridiculously low amount of money, $27,000 I think it was which I thought was a lot of money at the time and then started another one. Eventually got absorbed by a large bank and spent some time there in IT and technology for them and then got hired by Microsoft in the late 80s and spent 17 years there in two stints actually. 11 years and then was away for eight years and then back for actually for eight years I think it was and then back for another six and then left in 2014 and started another project, another company and eventually recruited some additional people out of Microsoft which turned into S2 after a few machinations. So wide range of companies, lots of different sizes, lots of different experiences. Well even at some of the big brand that a lot of us would know at Microsoft your experience there the between the two times you joined it's probably a very different company right? It was. I mean I started when there was just a few thousand, a very small company. Many of those were in sales offices around the world so the actual Microsoft campus was relatively small and I left when I left in 2000 there was we went from a few thousand to 35,000 and then when I came back eight years later it was 110,000. So you get to see different stages of the company and different challenges in the company depending on what stage the company is in. So that was very interesting, unexpected and very interesting. Right and I know even at Microsoft you've had a range of roles there. Can you tell us a little bit more about that? Yeah I did. It was my first job at Microsoft was on Microsoft Word. It was kind of midway through the process of the very first version of Word through Windows and so that was an interesting experience and then from there I think at some point the company at that point was the email system for the company was actually Xenix with dumb terminals. It's hard to believe now but and at some point Bill said we need to build our own email system that we can sell to our customers that's land-based and server-based and so me and another guy embarked on that and that was sort of the first of several sort of almost startup like things in Microsoft that we were tasked with doing and it was a lot of work and that was followed by others and then when I finally left Microsoft after doing a startup for online payment systems at Microsoft I left or retired and when I went back it was being a group that sat between the Microsoft Research Division and the Commercial Group to help productize some of the technologies were being developed in Microsoft Research and move them into the Commercial Division. So that was an interesting experience and got to exercise some muscles in evaluating technologies and determining whether they were good technologies to move or whether they were full products. It was we did a lot of that for that was about six years of that so that was very interesting but touched a lot of groups inside the company including you know Office and Windows and the online stuff it was good. Yeah one of the interesting things that you mentioned just now is sort of what the innovation life cycle looks like at different stages of the company right you know earlier in the earlier days it's someone might have decided we should build an email product or you know build our own email product and people just went ahead and did it right and later on there's there are folks like you who are sort of a bridge between a more kind of classic R&D organization and a more kind of productization commercial org. How do you think Microsoft was able to preserve the pace of R&D being able to put out good products despite you know growing extremely quickly? I think it's a challenge that every company has clearly in the early days it was really just the company deciding at a senior level hey we're going to do this or we're going to do that let's go figure it out and I think one of the things that made Microsoft successful in those days was that they weren't afraid to fail. There were a lot of things we tried that didn't work and and that was okay because we were it's hard it's hard now to think about it because things have evolved there's lots of examples there's lots of companies that you can point to and say well they did this right or that wrong in those days it was really very much uncharted waters at least it felt that way and so we didn't know and necessarily what was going to work and what didn't so there was a lot more experimentation early on with ideas and approaches and challenges and they gave people a lot of leeway. I can remember working on electronic payments thinking why am I doing electronic I thought that with email but I was probably one of the few people in the company that had experience with mainframe email systems so I got designated it was just that's how it worked but as the company got bigger of course that doesn't work and you have to be more thoughtful and mindful about how you do it it's hard to do that and so more processes came into the system and that makes it harder to innovate and do new things but it's I've yet to see a company who's escaped those challenges as they've gotten bigger and so the trick is not to try to avoid them but to understand what they are and the realities and try to manage the process that mitigates some of the challenges that come with size and decision making there's more distributed decision making and you know more people looking at numbers ahead of time and trying to pre-guess whether this is a good idea or not it's you have to be willing to take take risks and fail and and cut and to a large degree that's that stayed true but it became harder no question. Yeah I think as someone for for me personally who joined you know about a month before Cloudflare's IPO a lot of my role is thinking about how to put a little bit of kind of the process we need and a little bit of structure we need without without kind of ruining any of the things that made Cloudflare so great so far that definitely resonates with me. I'm sure a lot of the experiences you described were extremely helpful when you were starting S2 systems or when you're thinking about it and building the product and growing it. First I guess it would be great to hear just a little bit about what S2 systems does what led you to focus on on the browser security space or security in general and kind of how you envision the the company's growth. Yeah that's a good question we I think we started we we we had a project before S2 that at least three of the co-founders were involved in that didn't work out well so like many things it wasn't the first attempt but we in the process of what we were doing before it became really clear that that cybersecurity was a massive and growing issue for organizations of all kinds and at that point in time we were focused largely on the government and it became obvious as as I dug into it that the industry had really moved to a place where they were focused on ex post facto which means you get breached and then they have stuff to detect software is there to detect and remediate what happens and and the the genesis behind the idea of cloud part or of of S2 was zero-day solutions let's go find ways to not to not focus on detecting breaches and fixing unless focus on preventing the issues which is all around zero day and so the the the vision was that we would have a series of products in that space the first of which was was the remote browser isolation product because it's a definitive zero-day solution it works really well every enterprise needs it and and the plan was to grow the company we had no really plan to no idea that we'd really sell the company at least not in the first six to ten years that didn't that this wasn't on the radar and we certainly didn't imagine selling it to to another a larger company but the paths change and one of the things about startups is you need to be mindful of how things can change and how quickly they can change and so but that's that's where we started was zero-day solutions really definitively solving security problems and the the challenge of solving zero days depending on the type of surface is difficult and it's sort of the the holy grail in a lot of ways right with security if we can be immune to any sort of threats whether or not we know about it that's you know that that's the the state everyone wants to be in um how did you decide to specifically focus on on browsers and how the web experience yeah um i think in in i spent probably six or eight months just researching the cyber security space broadly um on my evenings and weekends um and it became clear that you know the vast majority of uh breaches come through um people's interaction with the Internet through endpoints and the browser is a big a big point for that um that's the on-ramp for the Internet for most people so we realized that focusing on the browser you know i think one of the analyst companies reported that if if people were able to prevent um breaches through browsers you'd be at exploits or other mechanisms that are used that that's 72 of all the breaches in enterprise that seemed like a good place to start and and we came across the concept of browser isolation and recognized that that was a very definitive way to address zero-day solutions we looked at the existing solutions that were out there and really was surprised frankly at kind of the state of the of the of the technology at that point in time and started looking for a better way to do it and and we found it um there's definitely some some luck involved in that but we found it as we were looking i suppose um and that's that's where s2 came from that's the genesis of it and that's how we ended up doing exactly what we were doing is because we had we had looked at a bunch of different things and seeing that there was an opportunity in the remote browser space because of where things were at in that industry and and when you say that you saw that there's an opportunity to see better what does that mean is it you know finding a balance of performance and security or is it sort of about if i think about kind of the other solutions out there or just security in general it's difficult to to make that balance right so was that sort of the focus it was um the the solutions that were out there at the time were um you know you had trade-offs and that's not unusual that there's trade -offs and and things that's that's part of life generally but they were pretty severe you either had to choose between a really slow system that was secure or a much faster system that wasn't wasn't as secure and broke things there were some compatibility issues with the systems that weren't pixel based and and you know that choice for customers that we talked to because we talked to a bunch of people about those trade-offs were very difficult you know they were between a rock and a hard place and we said well we could solve the solution that didn't require you to trade between performance or security or user experience or compatibility you didn't have to make those trade-offs that would be a very valuable solution and so that's where we focused and and we were able able to achieve that both you know as i said a combination of hard work and some luck yeah well we'll get to this in a bit but when i hear you say that it's i mean i think we had talked about this in the very first meeting between Cloudflare and s2 of what we know one of the things we believe with our products that you we try to extract that that that trade-off away right we try to deliver products in a performant reliable way while still delivering in the most secure way possible um but before we get more into kind of what you're working on at Cloudflare um i know you your your your uh your team likes to credit you with kind of pulling everyone together and uh really assembling the team and so when you thought about building out the team how how did you think about who to bring on what types of capabilities kind of how big the team should be that's a good question um lots of people approach it different ways my view on it was was looking for people with non-overlapping skills so you know the the other co-founders that that came on board um were were deliberately chosen you know when you work in the industry for many many years you always most people accumulate a list of people that they think are really really good and you think in the back of your head sometime oh man if i ever did a startup that would be a good person and that was the list i worked from um and and i looked specifically for people who who had skill sets that that i didn't have because there's no point in everybody having the same skill set or largely overlapping skill set we we need a broad range of of experience and perspectives and so it was a pretty deliberate process to go out and find those people with those those specific skills especially because we had the advantage which isn't always the case of of really knowing exactly what we were building and having a sense of what was skills were going to be required so that was that was helpful that doesn't always work out that way but that was helpful the other thing that i think was a factor is that the people that you know certainly for this first several um actually most of the employees that we hired um were people that we knew um and and that isn't people can take that the wrong way but when you're a startup and small everybody has to be firing every cylinder needs to fire and you when you hire somebody you don't know you don't understand their history you don't know how their work ethic is don't know you know the product the quality of their what they produce it's a risk and it's a risk for the company that you've got one or more people who aren't firing on all cylinders and so it was deliberate to find people we knew that were known people known entities known quantities um and and that we understood that what we would get from them that doesn't scale over the long term but when you're very very small and you're only you know six eight nine people everybody needs to be moving the ball forward um and it's a risk to take it's you can do it and we have done it in the past i've done it in the past but for this one uh the people that came on the team were known to somebody in the team not necessarily to me but to somebody in the team um and and that worked out really well they were all fantastic um really really good really good people yeah i uh having having worked with your team for a while now i can definitely attest to that um it's usually because i i had sort of a past life in in early stage investing venture capital and a lot of times we look at companies and founders and their teams and you know whether it's product market fit or building sort of their founding team a lot of times you sort of just see this one puzzle piece that's slightly off and it sounds like in your case you were really deliberate about trying to optimize where you could uh knowing fully well that you know you didn't have perfect information you didn't know exactly what the products would look like um but you tried to find the pieces that sort of wouldn't fail no matter what the product ended up looking like right you had great engineers they could build you know anything um but more importantly you have people that you could trust that could work together really well that could fire on all founders from from day one yep that's absolutely and on the on the topic of of team um so i think Cloudflare first met the s2 teams back in i want to say late august of 2019 right and so um m&a is something that that can be really distracting for for startups um you know or it could be a great thing but in in your experience um how did you sort of think about about the process you know understanding that was completely sort of unexpected maybe um how did you think about communicating with your team about it or thinking through the the decisions and path forward with your team yeah good questions i think um for us as i mentioned earlier we really weren't on a path where we thought we were going to sell anytime soon at least and and the reason that came up is we actually were out talking to a company that we were looking to partner with and in the very first meeting they learned about what we're doing and said hey you know we want to buy you um and we didn't it was which was a surprise um and we didn't really honestly take that too seriously because this individual i think was was was very excited by what we're doing but there's a big difference between individual interest and institutional interest and so we tended to discount a little bit the doubt that that was a serious thing um it was it was david and i in that meeting and but in in subsequent conversations with that company we realized no they are serious and there is institutional interest and that was a shock we just felt like we were way too early um but we recognized that if we were going to get an offer from one company we were not in a great position because we needed to have other options because we're young and we haven't had enough runway to develop the value where we think it needed to be so we took it pretty seriously that we were going to go um find and see if there were other companies that might be interested um and so very the team question in that is at the very first i think we we didn't say much to the team or anything to the team because we just weren't sure that it was real but when it became clear that it was real then then all the co-founders went met with that company um and that really kind of got us focused as a group saying okay so if we're going to entertain this you know what's what's the best way to approach this and we you know tactically mapped that out and and that's what we did um and so it was it was a danger as you mentioned because we weren't sure that we would get an offer that made any sense to us so we didn't want the team to be distracted um we told them what was going on but we really bifurcated the focus on what needed to be done in the company to move forward with our existing plans and this side process it was it was a debate um as to how much energy we spent on one versus the other we were actually in the middle of of raising our second round which we eventually fully had funded and was ready to go so we had the choice of you know we don't have to do anything because we have our money in place for the next next year or two um so it was an interesting process but as we worked through the process we when were there other there were other companies who were seriously interested we realized that a lot of companies and this was a revelation to the team and certainly to me was that there were a lot of companies who've been looking at this space for a long time and were actively out seeking solutions um and and then we realized at some point we realized okay this is the right time to sell even though it's way earlier than we thought and it wouldn't be our first choice um that's that's how we ended up and i remember our conversation our first conversation with Cloudflare and how somebody made the point very early on that Cloudflarer is focused on um you know uh security without without without compromise um no compromise to performance and no compromise to experience and that resonated because we hadn't heard that from any other companies that was a that was a a big deal for us yeah i i've seen a lot of companies who think of sort of browser security or or security in general as sort of this enterprise thing right like you know if you work at a large enterprise you you have the best in class solutions but um i remember one of the other things that sort of resonated between among all of us on that first meeting was that there's there's an opportunity to to sort of democratize it right and they to to deliver a secure you know web experience not just to fortune 50s but to to anyone that's and that's such a broad range of people um did did the did that our platform our reach kind of our our mission and working with different types of users and customers was that a factor in in what led you to join Cloudflare it definitely was um we we had we had choices as you said and we really were able then to when you have when you have choices you can make trade-offs when you don't have choices you don't get to make trade-offs and and we looked at the fit with Cloudflare we felt very clearly very early on that Cloudflare was the best possible technology fit with what we did Cloudflare's incredible network and the ability to run code of the edge is a perfect fit for remote browsing there's there's no better way to do it than that that is the if you were starting from scratch and and could ignore the realities of having to build your own network that's the way you would do it and here Cloudflare came along and had and had the network so that was that was part of it i think the other thing is that we were very impressed with the people um you know you in the end when you join a company you join a group of people and and the people were were great they were focused on moving things forward they cared about finding the right solutions people were would listen to each other they you know there was nobody in the rooms that we talked to who felt like they had all the answers and and that was important to us um and then you know from a company perspective it's a respect it was a it was a young company i mean Cloudflare is a young company we're many of us came from these large you know seattle megalith technology companies and and Cloudflare was a young company and it felt fun and invigorating and something like the old days again and that was that was exciting i think to everybody and then lastly i think that the thing that the drill was to Cloudflare was we really believed and felt like we had the ability to move the needle for the company both as a project and as individuals um and and that's you know for a lot of people highly motivating and and so there are a number of reasons why we picked Cloudflare those are a few but um in retrospect it was the right choice and we're we're very happy to be to be in the company and working away it's a six six months in and no regrets so far right no regrets so far the the reasons that we identified up front that were make Cloudflare attractive turned out to be true that doesn't always happen so that's good um i think some of the things that surprised me in a good way um is how mission focused the company is the the mission and mantra of making the Internet better people people are very aligned and unified around that and and that's very refreshing and it and it's clarifying because it makes things easier to to do um there are obviously trade-offs on on uh joining a larger company and not being able to run the show and make your own decisions but um Cloudflare isn't that big um at this point in time and it still feels like a very nimble company and and you know corporate overhead such as it is is appropriate for its size so um none of us we all know what what it means to work for larger companies and so there there i don't think there's been any surprises for any of us um in that sense so if i if i were a founder watching this segment it sounds like some of the you know maybe indirect pieces of advice or to to sort of understand as much as possible about the organization you might potentially join to really focus on on the people and the team and ensure that everyone's kind of incentives and goals and um visions really are are in alignment and those those are probably some of the more important things to figure out up front absolutely i think every situation is different um and and any advice i could give that would be too specific is probably less useful but from a principles-based perspective i think you're exactly right shared vision is important because everybody that starts a company has a vision about what they're trying to achieve and what they're trying to accomplish and most people aren't interested in abandoning that vision they they want to hold that vision so having a shared vision um is is really important i think the compatible culture which i think i mentioned before is is also important you know when you join a company you join a group of people and so it's a little bit like getting married you better like the people um and the culture that's reflected in that in that organization otherwise it's going to be a difficult a difficult process for you and lastly i think for individuals it's important to understand um what from a personal point of view drives career satisfaction for people um and and and be able to map that into the the company um to say yes will will this company be able to will i be able to to drive career satisfaction for my role and purpose in this company as part of their overall mission i think that's important when it gets down to the individual um more so than even the the larger company the larger startup or the larger company so i think those are some of the the principles there's several others but um it's uh it's a big decision for people it's a big decision yeah and i found having having worked on on m&a from both sides of the equation is that people often forget it's sort of a deeply personal decision at the end of the day right and you know the the dollar number sure definitely affects the the personal piece of it but at the end of the day it's where will you personally feel satisfied where will you feel satisfied from a career perspective and those are things that um you know we can't tell founders how to feel right they they have to just feel that for themselves that makes a ton of sense and then lastly on the point of sort of individual and team contribution when as you join the team um we also announced something called Cloudflare for teams so if you share a little bit more about what that is and and how browser isolation fits into it so Cloudflare for teams is about protecting the enterprise turning around what what what Cloudflare has done traditionally which is protecting infrastructure for people with websites on the web um and and it's taking the same infrastructure that same network and some of the same technology and turning it around and helping protect the enterprise um and Cloudflare for teams is focused specifically on that and it will you know it's a it's it's two core products at the moment but we'll eventually be at a range of products and technologies that work together leverage Cloudflare's asset which is which is that network and control of the stack from you know layer seven down through most of the stack um and protecting enterprises got it it's a it's an exciting product suite product family and uh i'm sure people hear plenty more about it going forward but thank you for joining us for this it was uh for chatting with you and appreciate you being super candid about about your experience leading up to poplar thank you appreciate it thanks aaron bye