Interview with Jon Williams from New York CTO Club
Adrian Bye: This is an interesting interview for me. I’m talking with Jon Williams. Jon is actually an Australian living in New York and he’s left Australia only just a couple of years before I did. He runs a pretty interesting organization which is pretty low-profile called the CTO Club in New York City, which is a collection of the top CTOs in New York. They kind of get together, meet and talk about stuff. Jon has been a CTO in a number of fairly well-known internet organizations and maybe he’ll tell us a little bit about that.
Jon, thanks for joining us.
Jon Williams: A pleasure. My pleasure.
Adrian Bye: Tell us a little bit about you. You said you’re Australian. I know you’ve got the accent as well. But tell us a little bit about where you grew up in Australia and where you’re from.
Jon Williams: Sure. I grew up in Melbourne, Australia which is the south coast but really more like the north coast of the United States. I went to Melbourne High School and Melbourne University and got my first technology job as a C programmer, programming C, a language not used today but that’s what I started on in the ‘80s. Actually we joined a startup. I was the number 11 employee at a company called Cyber Graphics that made computer systems for newspapers.
Adrian Bye: Cool. What made you move to the States?
Jon Williams: We were always looking for different tools for building computer systems. We were looking for operating systems, compilers and other tools to help us build software, and all of the vendors that I were using were based in the US. I came over on a business trip in 1984 and I actually had my first visit to Disneyland which might sound odd but was a dream.
Adrian Bye: No, I know. I mean growing up in Australia, all that stuff like the A-Team and all that stuff was pretty important – Knight Rider and Disneyland.
Jon Williams: Exactly and it was unlike the internet today where we didn’t have that ready access so it was hard for us to imagine what it was like in the United States. So I went to Disneyland and had a fabulous experience but then I went to the real technology Disneyland, which is Silicon Valley. I spent three days in Silicon Valley talking to a bunch of vendors and said to myself, “My goodness, I was born in the wrong country. This is my dream to work with all of these companies.”
Adrian Bye: You were in Silicon Valley in 1986?
Jon Williams: ’84.
Adrian Bye: ’84?
Jon Williams: Yes, talking to vendors to select tools and I got more done in three days in Silicon Valley than I spent a year trying to research tools in Australia, again, before the internet.
Adrian Bye: But, you moved to New York?
Jon Williams: Yes, I went back and then a couple of years later, my boss said, “We’re opening an office in the United States. Would you like to go?” I said, “Yes,” in two minutes, and I knew I was moving to a place called Manchester, New Hampshire. I thought it was going to be like California.
Adrian Bye: But, that’s like right next door to Silicon Valley then, huh?
Jon Williams: No, that’s on the other coast. That’s actually all the way up in New England and I knew it was in a different place but I just assumed the whole US was going to be like California – kind of a naïve Australian at that time. So I ended up on the East Coast, spent two years in New Hampshire, two years in Boston and then by 1990, finally found my way to New York where, if you come from another country, New York’s probably the best place to be in the United States.
Adrian Bye: I’m interested you say that. Why do you say that?
Jon Williams: Because it’s a real melting pot of people from around the world and actually around the country. I find there’s no colloquialism in New York that you have to be from New York whereas I find in other areas in the United States there’s kind of a caste about whether you come from that area or not. Whereas New York, it’s really people of the world who live in New York.
Adrian Bye: Yes, yes. That’s something I’d liked about the city, too. You grew up in Melbourne. I grew up in Hobart so we’re about an hour plane flight away.
Jon Williams: Yes and I guess Melbourne would be like Boston and then Hobart would be like Cleveland from a side’s point of view, right?
Adrian Bye: I think that’s being generous but… Yes. So you moved to New York and you’re working in tech stuff. How did you decide to be a CTO? When did you first become a CTO?
Jon Williams: I didn’t first decide to become a technology manager. I was actually promoted a few times and demoted, so I was a really bad manager. In fact in the beginning of my management career, I was a lead developer who had no people skills. One day, I woke up and figured, “Oh, gee, I don’t have any people skills. I better do something about that.” I had some great managers and mentors, and started to learn from them how to manage people and teams, and realized that as a lead developer, I can only get so much done. I was working at that time seven days a week and I could only get a finite amount of stuff done. When I started leading teams, I could get a lot more stuff done and that was my motivation to become a CTO.
Adrian Bye: How did you do that? I mean you don’t just like get people skills overnight. What did you do to learn to lead teams?
Jon Williams: I had a patient boss who I was able to work with on how to deal with staff. I went to some communication courses. I actually went to one communication course, which was really interesting, which actually had a segment about nonverbal communication which as a technologist with a scientific background I thought, “Well, that’s insane – there’s no such thing,” but realizing that there’s empathy, facial expressions, posture and other things which are really important elements in communication. I guess what I realized is, is I realized that I didn’t have good sensitivity skills to what my technology teams were thinking and feeling so what I started to do is I started asking them what they thought and what they felt, and then that was really the buildup towards becoming an effective manager.
Adrian Bye: How long did it take you to become a good manager?
Jon Williams: That’s quite a bit embarrassing. It probably took five years to go from bad to okay and then refining those skills ever since. I would say I’m still perfecting my management skills. I think I’ll never be done.
Adrian Bye: How big are the teams you’ve managed?
Jon Williams: I started with a team of 15 developers. All developers I was doing all the systems admin and DBA work myself and then I’d gone right up to close to 100 teams of 100 people where I’m really managing people who are managing people. Then it’s a whole different thing.
Adrian Bye: You mentioned like when you started asking the teams how they thought and felt but what happens if they don’t tell you or they don’t tell you the truth?
Jon Williams: You could only go by what they say. First of all, the relationships are based on trust.
Adrian Bye: Right.
Jon Williams: So you have to believe what they say but you take a point of view about it. In a particular conversation, you may say, well, that doesn’t sound right or it’s not making sense to me. There are safe ways to tell people you don’t believe them or you could make it objective and say, “That’s hard to believe,” instead of making it personal. The other tool is really not just communicating one-on-one with them but helping them communicate with each other. Then you’re getting other sources of information about your teams and it’s important to hear backchannel what’s going on with your teams as much as it is to hear someone directly.
Adrian Bye: Now how do you get that through the backchannel?
Jon Williams: By getting it from other team members. As long as you’re creating trustful relationships, not betraying confidences and not playing people off of each other, you’ll find that everyone has a focus on people working together and getting things done right, and so they’ll be happy to communicate with you when they hear about other people’s concerns. I find people are more than happy to pass along when someone is not happy or they have concerns so you just have to be an open door and make that okay for people to pass that along to you.
Adrian Bye: Interesting. So what other courses or materials did you study to develop this? I mean a lot of guys who run companies, it’s an area that’s fairly easy for them and it’s interesting in your case as someone that it wasn’t easy for that you’ve actually had to go and learn it.
Jon Williams: Yes.
Adrian Bye: The other reason I ask is because I’m not the world’s best manager either and this is something I need to learn, too.
Jon Williams: Yes and I have an opinion on it that technologists are typically not good at this. It seems that the people who are good at programming computers, being very focused on a single task in technology and all of that abstraction outside the real world seem to me as a generalization, not to be the best managers. Although open source is changing that and I’d love to get onto that topic as well but the starting point was realizing that I wasn’t a good manager and that there were people to learn from. Someone recommended a management training course at a college in New York. I can’t remember exactly what it was but it was an after-work management training program that I did for 12 weeks, one evening a week and it’s really the discussion about management as a topic and realizing that it in itself is a discipline. That was really the breakthrough for me. Up until that point, I thought people did management just naturally, and then I realized like I guess anyone who does an MBA would know that management is a discipline that you need to learn, that there are techniques, approaches and models to doing it.
Adrian Bye: Interesting.
Jon Williams: In one of the classes, I mean you can get access including online and I think it’s just a discussion with others on what management is about.
Adrian Bye: Yes, right. Okay.
Tell me a little bit more about companies you’ve worked at. I know you worked at iVillage. What are some of the other companies you’ve been CTO of?
Jon Williams: Yes, I was CTO at iVillage, part of NBC Universal. Before that, I was CTO at Kaplan Test Prep and Admissions, a division of The Washington Post. The Washington Post is doing north of $2 billion in revenues and over half of that is coming from the Kaplan Group of Companies. So The Washington Post realized back in the ‘80s that traditional media may be in trouble in the future and they diversified their portfolio into education so that’s why they acquired Kaplan. At Kaplan, I was doing a lot of work. A lot of our sales were done through our website so we had a significant e-commerce component. Plus, every one of our students, while most of them were studying in a classroom with a teacher, all of our students had online learning assets so we were doing a lot of work in e-learning and the online learning space. I really enjoyed that – a really, really interesting space for technology.
Adrian Bye: Those have been the main two – Kaplan and iVillage?
Jon Williams: Before that, I spent a couple of years at Grey HealthCare running a digital division of theirs, working with pharmaceutical companies on websites. Before that, I was a Consulting CTO for large companies like Time Warner, Scholastic and Oxygen Media, and then a whole bunch of startups back in the dot-com most of which are not around. Some are still around. I did some work with Bluefly which is an online retailer and an e-mail marketing company called Bigfoot Interactive that’s now Epsilon. Then back in 1997-98, I was the CTO at one of the first Silicon Valley companies to go public called N2K that ended up merging with CDNow and ended up getting folded into Bertelsmann. Before that, I was CTO at a company called Interactive Imaginations, which was a top-12 website, the number one website in gaming, and eventually got folded and became part of 24/7 Media. So I’ve been working on the internet or on internet-related products since 1996.
Adrian Bye: I’m curious. The startup scene has come and gone, and come and gone. I mean if you’re into tech, you’re obviously like leading or bleeding edge stuff. Why have you stayed with bigger companies rather than lots of startups over the last 10 years?
Jon Williams: Yes. So I started in the startups back in ’96 when the first dot-com wave was starting and after doing that for a couple of years, I decided that I wasn’t a very good business and stock picker. I’m the technology guy, not the biz dev or CEO guy so I’m not going to be able to tell you who’s the next Twitter or who’s the next Facebook. Yes, I loved working with those companies and I decided that if I consulted for those companies, that was the best way to work with many of them but not have to spend the bank on just one of those companies. When I consulted for three years, I worked with three large companies. I actually had dozens and dozens of startups that I worked with during that dot-com boom time in New York, and found that incredibly exhilarating but I wasn’t prepared to be the entrepreneur myself.
After September 11th, I started a family and took a more conservative route getting into large companies but frankly I’m currently in transition and I think there’s a pretty big possibility that I’ll end up jumping back into the startup scene. It feels exactly like 1996 in New York here at the end of 2009.
Adrian Bye: I’m interested to hear you say that. You think the way the money’s flowing and what’s going on in the startup community, you think we’re going to see another bubble?
Jon Williams: That’s what it feels like, and I’m completely comparing it back to my experience over a dozen years ago. I’m seeing both a lot of startup activity, a lot of series B and series C funding to existing companies that have been around for awhile, all of whom are making good revenue, and I’m also seeing a lot of digital activity in established and large companies. So I’m seeing it come from all over.
Adrian Bye: Yes, right. Okay.
I’m interested then to hear. Before we go on and talk about CTO Club, tell us a little bit about what you do as a CTO. I guess there’re some restrictions on what you can talk about with iVillage. If you can’t talk about specifics from what you did there, can you tell us just a little bit about what a CTO does?
Jon Williams: Yes, I mean I kind of boil it down pretty simple. What a CTO does is they align technology with the business and the plans of the business. What a technologist, what a CTO doesn’t do is they don’t deploy new technology for technology’s sake. They’re finding appropriate technologies that match with the goals of the business. So once you do that, and coming up with a strategy and a roadmap for technologies that match the business strategy, then the CTO’s job is to then put the right teams and processes in place to executing into that plan. I mean it’s simple, it takes a lot of experience and certainly being through my history of trial-and-errors, that’s it.
Adrian Bye: You’re an older CTO, right? I mean you’re like 48?
Jon Williams: Yes, I’m unfortunately one of the oldest guys in the room nowadays.
Adrian Bye: I mean if you’re looking at different opportunities. As a CTO, guys are going to say, “Nice guy and all but he’s 48. He’s going to want to run our site that’s going to get 200 million visitors a week and he’s going to want to run it on COBOL.”
Jon Williams: Well, that’s a little bit unfair. I started programming in C and at the time, that was bleeding edge. So C when I started programming, it was like Ruby-on-Rails.
Adrian Bye: Right.
Jon Williams: I moved to C++. The last time I coded, I was just starting to code in Java, and I’ve learned and picked up these technologies along the way. So what you will find in my history is I was always using the latest technology. I mean that’s what a CTO needs to do. They need to stay up to speed on what all the recent technologies are.
Adrian Bye: So that’s what you do, do, is it, and how do you make sure that you’re staying up to date and then how do you also avoid, because I mean technology can come in and be very fashionable for awhile and then later it just turns out to be pretty useless but it was just all trendy for a little while?
Jon Williams: Right. So the way that I stay up to date on technology is through my network and finding out what other technologists are doing with technology. That also helps you devein between the fashionable and trendy, and the stuff that actually really works.
Adrian Bye: So it’s your network of other CTOs? You guys talk a lot about what’s actually driving value and what’s just the latest fluffy thing of the moment?
Jon Williams: Exactly and that’s kind of what drove the idea around starting the New York CTO Club.
Adrian Bye: …which we’re definitely going to get to.
The other point I’m interested to ask about is then given that the leading edge technology is critical, if you’re working in a startup team – so let’s say you’re working alongside the CEO of a startup – sometimes that fluffy, new bleeding edge technology does turn out to be really useful and if you’re using only the tried-and-true stuff, it might be harder for you to work alongside the CEO of a startup. How would you respond to that?
I know I’m asking you tough questions but these are the things I’m really interested to understand.
Jon Williams: Yes, I guess I’m going to challenge the tried-and-true. I think you’re thinking more of a CIO or an IT Manager who’s a person who’s responsible for corporate technology where they get the phone call when systems go down or systems are too high a risk. That’s not what I’m talking about. I’m talking about making sure that systems actually work so you may hear about a brand-new technology that would be interesting and a CEO would want to try but it may not scale so then you need to share that information with your CEO and say, “Yes, we can try this, but it’ll only work to this point,” and I think that’s where technologists kind of let themselves down where they’ll say, “No,” to new technologies because of a reason. But what would be better to do is say, “Yes, but we’ll only be able to get to this point so as long as everyone’s fine with us reaching some plateau with this technology and that we need to revisit if we have a success,” then that’s my rules for adopting new technology.
Adrian Bye: How would you respond? Obviously, Twitter had some pretty public scaling issues over the last year. How would you respond or how would you have handled that situation of you’d have been CTO of Twitter during that time?
Jon Williams: Boy, that’s a tough question. I’ve dealt with similar problems of scaling. One of the biggest problems I had with scaling was because – and this was a number of years ago – I wasn’t connected with the sales and marketing team on all the traffic deals that they were doing with AOL, Excite and all of our other partners around our music website. My solution at that time was to get connected to that side of the business, get their traffic forecast which allowed me to forecast traffic, build to it and get funding from my CEO to build to that traffic size. Handling a lot of traffic isn’t magic. It’s a matter of planning – cost and planning. It’s certainly not magic and what happens at companies when they get into the difficulties like Twitter and others do, it’s usually for lack of foresight and planning on what’s going to happen next.
Adrian Bye: Yes, okay.
Jon Williams: I mean I wasn’t there so that may be up there. Sometimes it could be a particular product or a combination of products they were using that they hadn’t tested in a particular way or something unique they did. The other tentative building large-scale web properties – we didn’t have this 20 years ago when there was no large-scale web properties – it’s you’ve got to test them. You’ve got to build tools and build testing systems so that you know if you’re going to get floods of hundreds of thousands of users in a matter of minutes that you’ve already tested that scenario.
Adrian Bye: One interesting post I saw, talking about Twitter, was they obviously had extreme scaling issues in a short amount of time with technology that wasn’t really capable of scaling for them, and one of the posts I saw was the way the system kind of grew was bit by bit by bit, sort of they kept patching more things onto the next thing that was needed and solving the next problem as it came up, and because they didn’t really have time to really step back and solve it from an architectural standpoint, they ended up with a very brittle solution which worked but the problem was it was very brittle. So as different things happened or things needed to be changed, it became even more and more brittle, and it broke down a lot.
Jon Williams: Right, so what they didn’t do is they didn’t do a process we call refactoring…
Adrian Bye: Right.
Jon Williams: …which is coming back and when you’re building features in technology systems, the best way to it would be this but we don’t have time so we’ll do it this way instead and refactoring is taking that time out to come back and do things a way that will satisfy scaling issues.
Adrian Bye: Yes.
Jon Williams: They clearly didn’t allocate any planning time to doing that and now that they’ve had a very public incident, they’ve probably got a lot of funding and a lot of executive approval to do exactly that.
Adrian Bye: Yes, right. Yes and they’ve made the business work hopefully, anyway. It’s certainly growing.
Jon Williams: Yes and it’s a good problem to have. You know I’ve seen technology teams approach it the other way where they’re refactoring all the time, planning for huge business outcomes and overspending, and then the business doesn’t match it and the business would have been better off spending that money on marketing instead of technology.
Adrian Bye: Yes, totally. What’s your favorite like development environment or if you want to build a site like that, what are the platform and languages? I mean are you a Linux guy? Are you running everything on a Windows platform?
Jon Williams: I’m an open-source guy so I started working seriously with open source in 2004 when I started the Kaplan and I started an open-source strategy there. I’m a big advocate of the LAMP stack but also tracking some of the newer technologies particularly Ruby-on-Rails. I’m very interested to start doing some work with that. I’ve done some small pilot projects with it but I haven’t done anything major with it yet.
Adrian Bye: So you like Ruby-on-Rails? I interviewed Jason Fried from 37signals and that was one of the things he talked about.
Jon Williams: I’m finding people can really do rapid development with Ruby-on-Rails. The knock on it is scaling that it doesn’t scale.
Adrian Bye: Right.
Jon Williams: But the knock on Java back in 1998 that it doesn’t scale – all of these new systems don’t scale initially until you get enterprise thinking and work on them. If we take our enterprise technologist and they start to work on Ruby-on-Rails, we’re going to solve scaling. It’s going to get solved. No question. So it’s just a matter of what happens is you get a lot of these younger teams working Ruby-on-Rails not thinking about scaling, and then they just get stuck in a corner and have to move off that platform to a Java platform that’s known to scale.
Adrian Bye: But the irony is that they might not have had the scaling issues had they not started with Ruby-on-Rails in the first place and being able to quickly prototype what people needed.
Jon Williams: Yes, exactly but if they built in Java, it might have taken them two or four times as long to get there and the business may have failed in the process.
Adrian Bye: Yes, exactly. Cool! So tell us a bit about CTO Club. It’s obviously something that’s benefitted you. I read on your profile somewhere that you think you wouldn’t be the CTO that you are today because of it so what does that mean and what do you guys do?
Jon Williams: I absolutely wouldn’t be the CTO if I wasn’t part of it. So what happened was back when I was consulting, and I was working with other CTOs and CEOs, most of these people didn’t know each other, and they were effectively islands in New York City. I’ve done a lot of work in Silicon Valley and all my friends there have people they worked with at Oracle, Sun, Apple and all the other technology companies in California, and when they got stuck on a gnarly technology problem, they call someone up and get advice. I found that in New York that that just wasn’t the case. So what I did was I was working with Igor Shindel at Path Finder, and him and I decided to start the New York CTO Club. We got 15 CTOs in a room over breakfast and just started discussing technology.
Adrian Bye: I find I can imagine that first time you guys got together. Probably everyone’s heads like exploded and they were saying, “This is the greatest thing ever,” right?
Jon Williams: Not in the first meeting. Part of the problem at the time is we were all told to be secretive about technology. For some reason at that time, it was viewed as a competitive advantage not to share what technologies you were using outside of the four walls of your company. With open source today, that’s the complete opposite to what we all do. We’re all telling everyone what technology we use. So we were just a little cautious at first but what happened was like at the fifth meeting, I had that head-exploding moment where I found three other CTOs had experience with a vendor that I was actually in negotiations with. So here I am talking to three people that had already licensed the product that I wanted to use who were giving me the real-world case of what worked and what didn’t work, and how to work with this vendor. That was the breakthrough moment for me.
Adrian Bye: How was that a breakthrough? What did you do differently as a result of what those guys told you?
Jon Williams: I had information that I could reflect back to the vendor to hold them truthful to their product and their contracts that I didn’t have prior to that. I was able to sit down with the vendor and say, “I’m really worried about (X, Y and Z)…” that was not information that the vendor had given me.
Adrian Bye: Did your deal go through with that vendor?
Jon Williams: Yes.
Adrian Bye: Was it a better deal as a result?
Jon Williams: It was an absolutely better deal and I was actually consulting for the time. My client loved the product and made lots of recommendations for that vendor in the future.
Adrian Bye: So it was a good thing for everybody.
Jon Williams: Absolutely.
Adrian Bye: Were you able to knock the price down as well?
Jon Williams: Of course. That was part of it. I mean open source is now really helping us do that on a much larger scale than it did back then.
Adrian Bye: You’ve mentioned open source a few times. You guys are the group generally using open source a lot?
Jon Williams: I think open source is really coming back to me as a CTO and what my preferences are. What’s interesting about the New York CTO Club as a group is it’s eclectic. We have people from some of the largest companies in New York to some of the smallest so you’re going to find that they all have a different point of view on open source depending on whether they’re working for a bank, or whether they’re working on the latest consumer startup or in the niche industry. But we do end up talking about open source a lot.
Adrian Bye: Who’s in the CTO Club?
Jon Williams: Let me talk a little bit more about the club. It’s a nonprofit. It’s invitation only. So you really need to be introduced via another member to become part of the club. I have members from AIG, Barnes and Noble, Cablevision, banks like JP Morgan, Bank of America, Gore Hill, I have members from a couple of museums, and these aren’t just CTOs. These are people who have some type of technology-management role. Certainly if I had someone from Morgan Stanley, I don’t have the number one technologist there. I’ll have someone that’s managing a team between 10 and 100 people, and a budget between $2 million to $100 million in technology spend.
Adrian Bye: What are your guys like as a group, your total tech spend?
Jon Williams: Oh, total tech spend – I actually don’t have that number but it’s got to be in the billions range.
Adrian Bye: That’s your number one number or maybe you guys don’t care but like if you can put on your site like, “Collectively, we control $2.7 billion of technology spend in the New York area.”
Jon Williams: That’s interesting because we don’t focus on that. We’re private. You had opened in introduction that we’re low-profile. That’s actually on purpose.
Adrian Bye: Alright.
Jon Williams: We’re not a group that’s trying to expand or to do anything more with our group. It’s really something that individual members benefit from, and there’s a trust and camaraderie between a small, trusted group that you don’t get when you make it into a bigger group.
Adrian Bye: Right. So how does one get selected? I mean you said it’s through referrals. Let’s say I say, “Look I want to join.” Now I’m not a CTO and I’m not qualified. I’m a nice guy. How do you say, “No,” to me and then how do you decide which other guys do get accepted because that can be kind of a complicated issue?
Jon Williams: Yes. So if you were to ask me to join, I’d say, “I’m sorry. It’s only for CTOs or practicing equivalents.” We get around a little bit by allowing people to come as guests so they can at least experience and make some network connections from a one-time visit. But we’re really looking for people who are similar to the existing members so that’s why we’re looking for other members to say, “Here’s a CTO or equivalent that I know, and they’re like us. They’re going to be able to attend meetings regularly and contribute to our e-mail.” I’ve had a number of people who wanted to join but didn’t want to come to our monthly face-to-face meetings. They wanted to be virtual, and that’s not the type of member we’re looking for.
Adrian Bye: So they have to be New York City- based then?
Jon Williams: So New York City-based and regularly attend our monthly meetings. You don’t have to come to every meeting but make sure you don’t miss too many in a row and the reason for that is these face-to-face meetings is where we build the trust between the group and of our morning, two-hour meetings, we spend at least an hour just having coffee and catching up with each other. That’s where the real networking happens.
Adrian Bye: Yes, when you just chat about stuff then serendipity happens, and you find out you’re negotiating a deal with someone and three guys that have already done the same deal.
Jon Williams: Yes and in technology the equivalent of that is you’re looking at a new content management system and four people have already done an evaluation of all the vendors. When they get back to their desk, they’re going to e-mail you their evaluation document.
Adrian Bye: Yes, right.
Jon Williams: It’s going to save you like four weeks of work.
Adrian Bye: Yes. How big is the CTO Club?
Jon Williams: We have 80 members. It’s about 80-plus members. I’ve had a few members who’ve moved out of New York. We kept them on the e-mail list, and it’s actually a good way for them to stay connected to their New York network. But you really need to have been an attending member first before that happens.
Adrian Bye: How many come to a meeting? It’s in a big meeting room? You have a breakfast first and then a presentation? I mean like what actually goes on? Or do you have like a secret chant and you light candles?
Jon Williams: Yes, we talk Klingon, right? That’s what the guys do. I just read an embarrassing story of it. Some tech guy was teaching his kids and only talking to his son in Klingon for the first two years…
Adrian Bye: Oh, God!
Jon Williams: …which was completely embarrassing for all of us technologists.
But we have a sponsor. So Sun Microsystems has been our sponsor since we started 9½ years ago.
Adrian Bye: That means Oracle is your sponsor now?
Jon Williams: I hope so. There’s a lot of things on their plate and once they sort out what’s going on in the EU and going on with the stuff, hopefully they’ll get back to me and we’ll able to sort it out.
Adrian Bye: I actually know people at Oracle. If you need help with that, let me know.
Jon Williams: Cool, cool. I’ve actually had other companies approach me about sponsoring the New York CTO Club so people have definitely seen the value of it. It’s interesting because Sun doesn’t influence the club at all. They’re what I would call a backroom sponsor where they get to observe and they get to see what’s said but they’re not contributing. What Sun Microsystems decided was that they would benefit from allowing the CTOs to help one another and not intervening in that relationship.
Adrian Bye: But they do come to the meetings?
Jon Williams: On occasion, yes, they come. The guys are usually busy but they make as many as they can.
Adrian Bye: Yes, I mean it’s branding and they know the value in that. So you have a sponsor. That pays for a room and breakfast.
Jon Williams: Yes. We start at 7:30 AM. We’re done at 9:30 AM so everyone can get back to their desk by 10:00, and that’s a unique New York thing. If you’re trying to do this thing in Boston, LA or Chicago, you’re going to deal with freeways and all sorts of stuff when you leave a networking meeting whereas in New York, you’re 30 minutes from anywhere from the middle of New York. The first half of the meeting from 7:30 to 8:30, we’re catching up on each other on projects and just general networking. Then from 8:30 to 9:30, we have a different speaker every month. Sometimes it’s a club member. About a third of the time, we’ve had external speakers. We’ve had speakers like Fred Wilson from Union Square Ventures. We’ve had Jeremy Allaire who invented ColdFusion.
Adrian Bye: Let’s say you’ve got Fred coming in. What does Fred come and talk to you guys about?
Jon Williams: Usually talking about the state of startups and VCs. We had him come in the dot-com boom. We had come in 2001 right after the bust. So we’re getting different views from him each of these times.
Adrian Bye: How many of you are there in a meeting?
Jon Williams: We usually get about half of us, 40, and we don’t allow PowerPoint. So one of the things we do in these meetings is we make them highly interactive. When I prep a speaker for the meeting, I say to them, “You will be interrupted frequently and often, and you need to go with that. Please prepare a loose agenda and be ready to go where the questions are.” The reason for that is we don’t want to hear the fluffy, glossy stuff. We want to hear the real story. We want to hear what really happened.
Adrian Bye: Right.
Jon Williams: What was the issue and how was it dealt with? That’s one of the differences of the club and you were asking me before about Twitter – we had a presentation from someone from Flickr, certainly one of the largest websites in the world when it comes to managing media always online, non-video. He was explaining to us how they manage both their development process and their scaling. They haven’t had the same problem and basically it’s a matter of planning was what it came down to. Actually, they have a whole system of how they deal with huge traffic influxes, and what they turn on and off as far as dealing with that.
Adrian Bye: Really? Flickr actually has to deal with that like manually. They don’t just like handle it.
Jon Williams: When they first did it, they did it manually, and then what they do, what all of us do is we set those into automatic triggers.
Adrian Bye: Alright.
Jon Williams: One of the technologies you’ll hear around scaling is caching. We have caching. Caching gets refreshed every few seconds from a source so one of the things you do when you get a lot of traffic is you tell the cache, “Don’t refresh. Just keep using what you have in memory.”
Adrian Bye: Right.
Jon Williams: “and come back to the database in 10 minutes when the database doesn’t have to deal with the volume it’s dealing with.”
Adrian Bye: Yes, right.
Jon Williams: You can automate that.
Really what we do in these meetings is we get the real story of what actually went on behind technology and because it’s a safe environment, I find that people are comfortable having those real-world discussions. Their boss isn’t in the room so it’s okay for them to talk about what they were challenged with, what didn’t work and how they dealt with it.
Adrian Bye: So it’s up to you to make sure that you get interesting speakers to come so that keeps then the attention of the CTOs?
Jon Williams: Yes, so we’re doing two things. I’m always on the constant lookout for speakers but I’m also polling members to ask them what topics they’re interested in. For example, none of them are interested in a presentation on Twitter right now but all of them are interested in cloud computing and all the different levels of service coming from the cloud.
Adrian Bye: So if you had someone who came along and spoke to you about Amazon’s tools in that area, that’d be pretty interesting?
Jon Williams: Yes. If you happen to know the Amazon CTO, I would most welcome him as a speaker.
Adrian Bye: I don’t. Sorry. No, I actually don’t know many CTOs. I can’t help you with that.
Actually before we go on, before I change the topic, have you heard of an organization called The Research Board?
Jon Williams: No, I haven’t.
Adrian Bye: They’re pretty interesting. It was founded, I guess, in the ‘80s and it’s a group of the top CTOs across, I guess, the US and maybe the world. They only deal with the CTOs who are like the really, really big CTOs. Actually, I haven’t looked at this in like six years so I’m telling you some stuff that’s wrong. But the basic understanding I have of them is that it’s a collection of the actual ones that have all of the buying power of Fortune 500 companies that get together maybe something like once a quarter, and invite vendors like Oracle and so on to come in, hear what they do and sort of talk directly. It provides some influence towards buying decisions. The reason I’m remembering it is because what you’re doing sounds a little bit similar and I think their main office is in New York City.
Jon Williams: Yes. We’ve never used the club as an influence tool. One of our philosophies is the purpose of the club is being about giving. So it’s about helping others. That steered us away from that influence. But that may be something we’re interested in, in the future.
Adrian Bye: Yes, if you do a search on The Research Board, it’s just researchboard.com.
Jon Williams: Cool.
Adrian Bye: Yes and their website actually shows a picture of their office. I was just walking with a friend and I was like, “My God, there’s The Research Board that I looked into a few years go.” So on the website, it says, “The Research Board is an international think tank headquartered in New York City. Membership is by invitation only and is restricted to Chief Information Officers of the world's largest corporations.”
Jon Williams: Right. It’s the Chief Information Officers that have the buying power and it’s the Chief Technology Officers who are the ones who are really more focused on technology itself. So you’ll find CTOs don’t have the same buying powers as CIO.
Adrian Bye: How do you guys make sure that you have the right level of influence there or do you not care? I mean let’s say someone comes on to speak to your group because there’re a lot of potential people reading this who would be potential speakers for you if you’re interested in a business perspective on stuff. They’re not going to be the tech guys as much but they will be the business guys. How do they know that you don’t have just 40 guys in the room who each have two guys reporting to them?
Jon Williams: I’m just trying to understand the question. How do I make it valuable or are you talking about…
Adrian Bye: I mean what’s the level of influence and leverage from your guys? I mean you don’t restrict just to the CTOs of companies, right? You do have guys that are not CTOs. Maybe if they’re Morgan Stanley, they might be just running a group of 10 people at Morgan Stanley.
Jon Williams: Right, right.
Adrian Bye: So leverage then that the guy gets for coming in to speak like how do you make sure that you’re always maintaining a high level and what is that high level you care about?
Jon Williams: Right. So the high level is the knowledge around technology and technology management. What you’ll find is that a more junior person at Morgan Stanley or in a large bank, not to pick on any one company, would be closer to the technology and dealing with those technology issues. That’s what we say to the speakers. So a speaker who’s going to come in and talk in broad terms about the IP systems then this is the wrong audience. But a speaker who wants to come in and talk about security and scaling issues with cloud services then you have exactly the right audience.
Adrian Bye: No, I get that but how does that speaker know? Let’s say there’s the best guy in the world on cloud computing, let’s say it’s the Amazon CTO who you really want to hear from, how does he know who you have in your group? I guess what I’m trying to understand is like the membership criteria if you’re okay to talk about that – how you do or don’t accept someone and maintain a level, and what is that level you care about maintaining. I mean I go through this with who I select for my interviews.
Jon Williams: Right.
Adrian Bye: I’m extremely picky about it. I’m interested to understand how you guys deal with that same problem.
Jon Williams: First of all, we haven’t found speakers screening us by general membership population and I never give out a list of members although that’s something you can go and find. What will typically happen is they’ll know one or two members and they’ll reach out to them as we all do now in this new internet world, ask them what it’s like, what should I expect and what’s the level like. I think as you speak to any member, you’ll hear the same thing over and over – “This is a completely unique group. It’s very interactive. It’s a high level of skill and understanding of technology, and it’s very cooperative.”
What we’ve actually found is we’ve had a number of speakers who are actually looking to learn something about their technology and then this is exactly the group. So if a speaker is willing to come in and actually have an open dialogue about a particular issue – let’s take open source as one example – then this is exactly the group that’ll help shape thinking around that particular technology.
Adrian Bye: Can you give me more of an idea of who fits the profile as who you’d accept for a member and who doesn’t?
Jon Williams: Yes. It’s the CTO that’s managing, let’s say, between five and 100 people who spends more time thinking about technology architecture and processes around development than they spend, say, working with vendors and budgets although we have some different people. We’ve actually had some speakers who have niche technology jobs actually request to join the club after speaking to it, what was really the ultimate compliment and we’ve accepted a few people of that ilk.
Adrian Bye: How big do you guys plan on getting?
Jon Williams: I think what’s interesting is we have no plans. We didn’t have any plans from day one. We’re almost ten years in, and we still don’t have any plans. Our goal is to provide value to our existing members and we do that organically in member letters. While we continue to do that, we’ll just continue to be successful. We don’t have any other goals. I know that sounds maybe counter to every other group that you meet but it’s been a successful model for us.
Adrian Bye: Yes, right. Do you guys ever like blackball any like vendors that you don’t like?
Jon Williams: We definitely say bad things about vendors that we don’t like. We definitely do and that’s in our private e-mail list.
Adrian Bye: Right.
Jon Williams: If you do one of these companies with a member wrong then everyone else is going to hear about it. But technologists will judge everything on merits.
Adrian Bye: Right.
Jon Williams: So there’s always a merit opportunity for every vendor.
Adrian Bye: So the main components then of your organization are the monthly breakfast and networking for an hour, then the meeting with the guys for an hour and then the e-mail list which mostly goes locally although there’s a couple out of town. Are there any other major components to what you do?
Jon Williams: The other thing that’s harder to track but we really promote and encourage member connecting separate from the club, having lunch and breakfast. Often, someone will ask a question and as often as not, they will get an answer offline from the general e-mail list because it’ll be the nature of a private conversation discussion. So we have that as well. The other area that that comes up is in hiring as well. We want to be cognizant of not poaching each other’s technology team and handling that in a delicate and professional manner.
Adrian Bye: Right. Interesting. So anything else you want to tell us about CTO Club?
Jon Williams: I know there’s been some other clubs started in other cities that maybe haven’t reached the size of the group. A lot of people tell me that’s because New York City makes it easy for people to get together and go back to their desk. But I guess what I’ll say for anyone who’s interested in networking is the CTO Club is just one of many networking organizations. I think for technologists, networking itself has an extremely high value. I find every time I talk to a new technologist about a technology, I am in constant learning mode and technologists love to learn. There’re so many amazing places in New York. The New York Tech Meetup is one of those. Even if you just start scanning technology groups in meetup.com, there are so many different opportunities to network. SIM in New York and the tri-state areas in other technology networking group open to all, there are just many, many opportunities and every team that I’ve ever worked with, and every team that I’ve ran, I’ve always encouraged them to network as much as possible.
Adrian Bye: Yes, because it adds a lot of value. Okay.
So the other area that I’m interested to ask you about is for potential guys who are going to make startups that are business type guys that want to find a CTO type cofounder. How would you suggest is the best way to approach that?
Jon Williams: Oh, my! That’s a hard question.
Adrian Bye: What have you seen that’s worked?
Jon Williams: What have I seen that have worked? It’s usually been through a personal connection. The model I think that works best is to find someone that you worked with in the past. That’s the absolute best model because you know what you’re getting, you know the relationship. If the relationship is all done and if you’re a startup CEO or executive, find someone that either you’ve worked with in the past or someone you trust has worked with in the past. If that’s not available to you for timing or whatever reason, the next way is to get out to these networking events and just meet as many CTOs as possible. New York Tech Meetup is one of them. Start to meet them and find the one that’s right for you.
Adrian Bye: Of your group of 80 guys, how many of those guys want to go and make startups?
Jon Williams: Of the existing group, we probably have about eight of them in startups so it’s only a fraction. Most of them have corporate jobs.
Adrian Bye: Is that where most of them want to be? They want to stay in big corporate jobs?
Jon Williams: It depends. I think we go through cycles. The difference between the startup and a corporate job is risk reward. The corporate job is much more risk and for CTOs like me as you get older, you’re looking to have less risk. It’s really the early CTOs who are more willing to take the risk.
One model that I’ve seen work well that I like, that I contribute to is CEOs having a seasoned CTO or technologist advising them and helping them select a young CTO. I think that’s a great model because you can basically grab any technologist you know from any company, buy them breakfast, lunch or dinner, e-mail them and pick their brain. While they’re getting paid in their day job, you can get them to advise you on how to approach technology if you’re a new startup.
Adrian Bye: So what you’re saying is that you guys can effectively take sharp tech guys and turn them into CTOs?
Jon Williams: Yes. One of things you’ll find between a seasoned CTO and a sharp tech guy who’s becoming a CTO is the seasoned CTO has the network, and knows when and how to ask for help.
Adrian Bye: Right.
Jon Williams: Whereas the young, sharp guy thinks the only thing they have in their toolkit is solving every problem themselves.
Adrian Bye: Yes, right.
Jon Williams: What’s interesting when you see these companies running into scaling issues – have they talked to five other people who’ve had these problems before. The thing about technology is in almost every case, someone else has had this problem before you had it so go and talk to them.
Adrian Bye: Yes. No matter how new and on the edge you think you are, there’re other guys that have dealt with the problem in some context or another, you know?
Jon Williams: Exactly.
Adrian Bye: Everybody thinks they’re all a unique, special snowflake but they often aren’t.
Jon Williams: Yes and when I’m advising a young CTO in a startup, I’ll be like, “Tell me the problem. Oh! Go talk to (so and so)…”, “Go research that,” or “Let me make an introduction here,” and technologists find that when they help others, they’re almost always getting something in return. That’s not the motivation for it. This is something CEOs do really well and I think CTOs kind of lag in realizing that this is a valuable job skill.
Adrian Bye: Yes, right.
Has it helped you in your career that you have the CTO Club behind you? I mean when you’re looking to work with a new company and they know that you have this at your back, does that assist you?
Jon Williams: It does. I make sure to mention it when I’m talking to companies and more than that, it’s helped me in some jams. I had a jam. This was back a few years ago. I had a jam with an expert. I was having problems with the work for me in a particular system. This was quite a number of companies ago, and I had a jam on a Friday. Through the New York CTO Club by Monday, 9:00 AM, I had an expert sitting in my office working with me on the solution. I wouldn’t have had that if I hadn’t have been a member in the New York CTO Club.
Adrian Bye: Interesting.
Anything you want to tell us about which we haven’t talked about?
Jon Williams: I’m a big advocate of open source and I’m really fascinated with how open source is changing the nature of technology teams, turning them into networkers. I think 20 years ago if I had told people when I was interviewing for jobs that I was a heavy networker people person, they wouldn’t have believed that I was a good technologist.
Adrian Bye: They would’ve come up and wanted to hug you and then you’d be like, “I don’t hug,” and now, you’re Mr. Networking, Mr. Touchy-Feely Manager Guy.
Jon Williams: Exactly. Twenty years ago, everyone wanted the technologist that you’re stuck in a closet and pass notes under the door with a broomstick.
Adrian Bye: Yes.
Jon Williams: Open source has changed our view on that. We realized that put two of these people together or put three of them together and magic happens.
Adrian Bye: Have you had Richard Stallman come along to speak?
Jon Williams: No. What’s his name again? I’m sorry.
Adrian Bye: Richard Stallman.
Jon Williams: Where’s he from?
Adrian Bye: From GNU.
Jon Williams: No.
Adrian Bye: He’s the guy that invented the GPL.
Jon Williams: Cool! We would love to have him speak.
Adrian Bye: He’s up in Boston.
Jon Williams: Cool. I had Matt Asay and John Newton from Alfresco. I did some work with them. They have come and talked about open source a couple of times to the group.
Adrian Bye: I’m not familiar with them. I probably do know a bunch of people that I can help get you speakers for if you’re interested.
Jon Williams: Sure. We find speakers who want something different. They may be sick of doing the broadcast meeting. Plus, some of these speakers will have a meeting with three of four people in a company and have a great interactive but this is an interactive with 40 people so I think it is unique.
Adrian Bye: Yes. Cool! Okay.
Is there anything else you want to talk about?
Jon Williams: No, I think that’s good. I think I’ve probably talked too much.
Adrian Bye: You did a good job. Thanks so much for your time.
Jon Williams: Hey, great! Great to speak to a fellow Aussie.
Adrian Bye: Okay, thanks.