S01E15: Ray Hightower

18 Mar 2011

We interview Ray Hightower and talk to him about all the cool conferences he organizes and his take on the Ruby ecosystem Susan: Welcome to Engine Yard’s Cloud Out Loud Podcast. I’m Susan Layman. Our guest today is Ray Hightower, the founder of WisdomGroup and the organizer of Chicago Ruby group. Welcome Ray.

Ray: Thank you very much Susan. Thanks for having me.

Susan: Your welcome. Thanks for coming and chatting with us today.

Ray: Appreciate the invitation.

Susan: Great. So let’s get started. Let’s talk a little bit about your own background and how you became involved in tech generally and Ruby on Rails specifically.

Ray: Yea ok sure. I have an eclectic background and I find that a lot of people in the Ruby community have come from all different walks of life. I have a CS degree but I was in college in the 80s so of course Ruby didn’t exist back then, object-oriented programming barely existed and I have a CS degree, I worked for IBM for a number of years, I did commercial real estate and after that in 1994 I started WisdomGroup. And we did networking with Novell Networks and Microsoft Windows NT, later to be Windows 2000 and eventually XP and they’ve changed the names of their operating systems a couple of times and we got into Rails really because we were doing web development. People liked what we were doing with networking, they gave us permission to do some projects for them on the web. We did our first few in ASP and PHP and one day an intern working for my company said, “Hey, Ray I’m working with something called Ruby on Rails” and I said, “What’s Ruby on Rails” and that’s how we got into Rails.

Susan: Wow, that’s quite a background.

Ray: Very secuitous.

Susan: That’s right.

Ray: Yea.

Susan: So, let me switch gears a little bit. What does community mean to you and what makes Ruby on Rails community unique?

Ray: Wow. Big difference between the rails community and what we experienced when we were working mainly with the Microsoft and Novell networking technologies. Everybody’s very engaging and everybody’s helping each other, we’re all helping each other. And, if I ask my self, “What is it that has--what is it that’s fundamentally different there?” and I think a lot of that is due to the open source roots of Ruby and the open source roots of Rails. You know there’s just--everybody--you know I heard somebody say its like a big hippie commune. I don’t think of it like that, that’s kind of like a tongue and cheek way to look at it but yea, everybody, we’re all helping each other from the meetups to the conferences, everything across the board, we’re all helping each other. So yea we definitely--I think a community is a group of people with common interests and common goals who help each other.

Susan: That’s great. And they all come from different backgrounds.

Ray: Oh goodness, all over the place, We have people who have business backgrounds, we have people who have PhDs in physics or material science or mathematics, we have MBAs, we have lawyers and law students, there are some physicians, there are dentists, there are people all over the place. I met a plastic surgeon at a Ruby conference 2 years ago and he was just there because he like the technology and you know, yea, all over the place.

Susan: Right. Ruby makes it very easy, I suppose, to get involved in programming for a lot of, I would say, non-programmers.

Ray: Yea, for starting up I would say yea, yes. Its a tool that’s really easy to get started. You know, its kind of like chess. You can learn the basic moves of chess in a few hours but it can take a lifetime to master it and I think Ruby’s a lot like that. You can learn basic moves but you could spend a lot of time just mastering, you know, learning the idioms and design patterns and all of the things you can do. It’s just wonderful. Very expressive.

Susan: Great, thanks. Now in one of our previous podcasts, Sarah Allen talked a bit about the Ruby ecosystem. Now would you say that the Ruby community has become more of an ecosystem.

Ray: Uh, you could say that. I suppose I should give you what I think an ecosystem is before I start tossing the word around. But, I think an ecosystem is a--you could say its a community where people within the community are dependent upon each other and helping each other and because we all exists and we’re dependent on each other, we’re able to do things that none of us individually could do. We’re able to accomplish more than any of us could accomplish as individuals. So, for example, you’ve got some companies that provide training and they also provide consulting. Sometimes they compete with some people that they’re doing consulting for, sometimes they cooperate if a project is big enough. There are certain companies here in Chicago that hire consultants from a variety of companies and those companies are actually cooperating to keep that customer happy because its good for everybody. So, you know, there’s an ecosystem in that sometimes we’re competing with each other but most of the time we’re cooperating with each other because there’s just so much opportunity out here that it just makes sense for us to all help each other.

Susan: Right. And that ties back into your last point regarding helping one another but at the same time moving the technology forward, evangelizing the technology into different types of opportunities and different kinds of markets because people from all works of life are part of the community.

Ray: Oh yea. You know a good example of that? There’s this guy Corey Haines who you’ve probably met in the community who did a tour of the planet--pair programming with people all over the planet. Well he started working with Obtiva and Aflight and they do craftsmanship swaps, EdgeCase has gotten involved with that, Relevance has gotten involved with that, where they swap craftsmen and share best practices in all of their studios. I think LeanDog has been part of that. LeanDog in Cleveland has been part of that also. So yea----there’s so much opportunity and we’re still all defining what excellence means, you know what I mean? Yea, we’re still defining what excellence means because the tools are constantly evolving and the needs of the clients are constantly evolving and as we develop new tools, clients are say, “oh you can do that” and I got a new way for you--you know something else you can do with that and its just--its a real cool upward spiral. So, yea there are a lot of companies here in Chicago and a lot of other cities that are participating in those craftsmanship swaps and I think that’s exciting.

Susan: That is exciting.

Ray: Yea.

Susan: So let’s talk a little bit about the community events you participate in or have organized in the past. Tell me a little bit about these events and why they’re so crucial to the community and have you seen the community change in the past few years.

Ray: Oh yea. You know, what has changed in the community is that 2 or 3 years ago, if there was an event you wanted to go to, you could just go. Now, if you want to go to an event, you’re looking at your calendar and you see there are multiple events on a given night or a given day, all of which are good, all of which that you want to go to and you kind of have to pick and choose which ones to go to and its hard because there’s so much good stuff happening at the same time. There’s the Chicago Project Management Group here, there’s ChicagoDb which is all about NoSQL database, there’s ChicagoRuby which my team and I run. There’s all over the place, so many things happening at once. There’s a Chicago Javascript group and if one thing has changed, I would say there are a lot more people organizing a lot more high quality events and so much good stuff is going on. Last night I was at the Chicago CoCa Heads Group. It was wonderful. People who are passionate about MacOS X program, and an iOS program on the iPhone and the iPad so there’s a lot going on.

Susan: Right. A lot of sharing, a lot of swapping of knowledge.

Ray: Yes, yes. And we all have to swap knowledge because you know what? The NoSQL database people of course, there’s got to be a front end. You’ve got to have a front end for your database or else its just data sitting there You got to have some way to get to it so your front end people can be your Ruby your Rails people, could be Javascript people on the front end or if you’ve got a mobile front end, then you’re pulling in your iOS people, your Android people, Java people, now web OS people. If you see the announcement that HP just made, so everybody--everybody is specializing in their niche and then we’re all sharing across the board.

Susan: Right, that’s interesting because the vendors may be competing but the developers really aren’t competing.

Ray: Yea, you know, and we all joke about it sometimes but yea there’s competition. Its kind of like sibling competition. I think about my brother--my brother’s name is Edward and growing up--we’re a year apart in age and we fiercely competed with each other but I think we both did better because we each had the other to compete with and that’s kind of what’s happening and its a friendly competition. I don’t see any back-stabbing out there. We share stuff with each other. I go to Obtiva’s Geekfest and they welcome me there, i welcome them to the events that I’m responsible for and we all have a good time because there's so--there’s too much stuff out there. It's like we’re in a huge ocean with all of these fish and we only have a few boats in this huge ocean so its better to help your fellow fisherman gather the fish than to try to fight over fish. There's too many fish, you know what I mean. There’s just a lot of opportunity there.

Susan: I understand. So tell me a little bit about the challenges you’ve encountered as an active community organizer. What are some of the lessons that you’ve learned?

Ray: You know what, we actually posted a bunch of our lessons in our GitHub repo. If you go to GitHub and look at ChicagoRuby in GitHub, just spell it out, Chicago-Ruby-in-GitHub you’ll see our guidelines for organizers and we did that to increase our truck number and basically what we have there was a bunch of things we wish we had known when we were starting off and a bunch of things that we want to pass on to the next group of organizers if we all go off to other parts of the world to live on tropical islands somewhere, right. But some of the things that--the biggest challenge, you want to make sure that if you’re running a group, make sure it is extremely easy to find in Goggle. That advice was given to me by a guy named Ryan Platty who at the time ran CHURB which was the Chicago Ruby group at the time. So you absolutely want to make sure that you’re really easy to find in Google. You want to make sure you welcome new people coming into the group. You got somebody who just moved to Chicago, they’re interested in Ruby, you want to make sure that--I try to make it a point to go up, shake everybody’s hand, myself, ask them where they’re from and that type of thing. I try to remember everybody, I can’t. We have over 1000 members but I really try hard to remember as many as I can. But just make people feel welcome and let people know that there’s an opportunity for them to contribute. We’ve got amazing developers here, especially in Chicago. I don’t know if you have developers in Silicon Valley. I’m just kidding. But we’ve got some amazing one here and let them know that there are plenty of opportunities for them to contribute make them feel welcome, make sure you’re very easy to find on Google, and I think everything else kind of like, comes from those. I think those are the root things you want to make sure you do.

Susan: That’s great. Thanks. So, what advice can you offer someone new to the community who’s organizing, perhaps in a leadership position that might want to help cultivate their local community? Where should they start and are there any resources for newbies?

Ray: Yea. One of the first things I would look at is, like I said, the files we’ve posted in the ChicagoRuby GitHub repo about organizing groups because that’s all about lessons learned, things we wish we had done. We call that, How Chicago Ruby Works and there’s an org chart there but--and things we’ve done that work really well for us. There are some other organizers I know that have written up similar guides and I’m not remembering right now which ones and where but you know, every now and then like at RailsConf we’ll get together and we’ll meet and we’ll talk about what everybody’s doing so I would get together with other organizers, international conferences or national conferences or even regional conferences and learn from other people triumphs and other people’s mistakes. And we’re all making mistakes--that How Chicago Ruby Works document, a lot of that is “o yea, this is what I wish I had done” that kind of things so, that’s where we get our lessons from.

Susan: That’s great.

Ray: Yea.

Susan: That’s great. Okay, so let’s switch gears just a little bit here. You know, in your mind what’s the relationship between technology and entrepreneurship?

Ray: I think technology--what’s the best way to say this? Technology accelerates entrepreneurship, and I say that because, and I’ll say specifically information technology because we could talk about technology in general but I’ll say information technology since that’s the area that I know. Information technology accelerates entrepreneurship because it enable us to communicate, really, really fast. You and I are 2000 miles apart right now, we’re communicating over the Internet via voice over IP, packets going out over the Internet and my goodness, some years ago a call like this would’ve been very expensive but we’re doing it over Skype right now and its not very expensive doing it over Skype. So that’s one way that technology accelerates entrepreneurship because you and I are able to communicate on things. We’re a customer of Engine Yard and Engine Yard is a sponsor of WindCity Rails and our other conferences, WindyCity Go and WindyCityDB so we’re each other’s customer and that’s accelerated because we’re able to trade information about what you want as Engine Yard and what we want with WindyCity Go or WindyCity Rails via email or Google Docs or Skype or what have you. It accelerates it or if you look at--could Groupon have existed if the web didn’t exist or? It couldn’t have. Technology has accelerated the growth of Groupon and of Apple and Microsoft and of the consulting companies here. I would say ultimately technology must serve entrepreneurship because its really the entrepreneurs that are steering the boat and technology is commander Scot in the engine room saying, “Yes captain, let’s make sure we get plenty of di-lithium crystals in the warp core so we can achieve warp factor 28 or whatever, if the warp numbers go that high, I don’t think they go that high but you know what I mean. So, you can say technology is like the team of engineers and engineering you know, making sure that warp core is stable and putting out energy and the entrepreneurs on the bridge saying, “ahead warp factor 8” and the entrepreneurs don’t know the details of how all that happens. You know, Captain Kirk could never go down to the engine room and do thing number 1 with a warp core, he wouldn’t know. Right?

Susan: That’s right, that’s right.

Ray: Could you imagine that? Or Jean-Luc Picard couldn’t or Kathryn Janeway--and I get into Star Trek if you can tell. So, each person on the team plays their role and if we all work together really well, we achieve some really excellent things. No one of us, I think it was Woodrow Wilson that said this, “No one of us is as smart as all of us” and you know we all come together and achieve some great stuff. So yea, technology accelerates entrepreneurship.

Susan: Yea then you add in the community and you’ve got something that is going blazing fast.

Ray: Oh yes. Absolutely, absolutely. Yes.

Susan: Okay so you’re passionate about exposing young people to cutting edge technologies. Why is it so important to do so?

Ray: Because, you know what, because its cool to watch them learn and grow and absorb this stuff and its fun to watch them learn and they challenge us, you know. There’s a kid--I call him a kid because I’ve known him since he was an infant but he’s now 16--well he’s 16, he’s still a kid. Anybody under 30 is a kid as far as I’m concerned, right? So this guy in my boyscout troop just made eagle. For his eagle service project, built an Ubuntu lab at our church and he is so passionate this stuff. We put it in front of him, showed him how to download Ubuntu and install it and now he’s going off in Google just to find new places to learn more about Ubuntu. He’s sharing it with other scouts in the scout troop and now there’s like a group of scouts talking trash with each other about what they can do with Ubuntu on their computers. And you know what’s so refreshing about that? Kids do that naturally when it comes to sports, when it comes to physical things but to have them do that with an intellectual pursuit, with something like an Ubuntu installation or an Ubuntu configuration and then to go off, and they’re talkin--but its all in good fun because they’re pushing each other and competing and because they’re competing they’re all getting better and it pushes me as one of the leaders to keep getting better myself because, my goodness, what am I going to teach these guy next? You know what I mean? You gotta do that. I won’t always be a--its an honor to me when they pass me--one of the guys that works for my company now is--grew up in my scout troop. He’s like 25, 26 years old and he’s doing amazing things with networking that’s so far beyond what I know how to do and I’m so proud and I learn from him now. He came in as a--where I was a mentor and all that and now I watch him do this stuff and I learn from him. So, when we teach our children or our teenagers or our youth in our communities--I do it in the boy scouts, I do it in my church, when we share that with them, they in turn come up with new ways to do stuff that we never even thought of. They challenge us, we all grow, our brains stay active. It's wonderful.

Susan: Right. They’re going to be our leaders when we’re--

Ray: They are going to be our leaders. The kid who did the Ubuntu lab, he--we have another leader who was having problems with his laptop and the young man who did the Ubuntu lab wiped out Windows on this leader’s laptop, installed Ubuntu--now that leader--this is a businessman--a very successful business man who has used Windows all the time that he’s been using computers, now he is very, very excited about Ubuntu because this teenager introduced him to Ubuntu. And he’s able to take care of things he needs to do businesswise and not deal with virus issues or malware issues and he told me Monday, he says, “Hey, man this is faster than it was when it was running Windows.” This was done for him by a teenager who just got introduced to Ubuntu last year, last November, December of last year.

Susan: That’s really cool.

Ray: Yea, so, I get hyper about this stuff Susan. Is that okay if I get hyper?

Susan: Absolutely, I love it. It's very infectious.

Ray: Yea, right.

Susan: And finally, you’re committed to making Chicago synonymous with high tech. Can you talk a bit about some of the innovation that’s taking place there now?

Ray: Yea, well you what, one that has gotten a whole lot of press, well recently with their superbowl ads, you know, Groupon. That’s just wonderful. There are so many other companies here. You know I think of software development companies like ThoughtWorks is based here, they are a global software development company. Obtiva is based here. Aflight is based here. WisdomGroup, my company, is based here. What’s exciting is that many of us are bringing on interns or apprentices and helping them to grow and when they have ideas about what we can do with technology, they can approach entrepreneurs who, “Whoa, gee I hadn’t thought of that. Let’s do this and let’s grow a business from it.” I keep mentioning Groupon because they’re in the press but its really exciting because I don’t know how their business model could have existed in the days of just newspapers and mainframes. You know? And they were grown right here in Chicago. They started off Andrew Mason and the guys at LightBank were originally doing The Point and they did a pivot--pivot classic Steve Blank from Four Steps to the Epiphany. They need a pivot from The Point to Groupon and they’ve grown and there are other companies like that that are not as well known, that are not getting as much publicity but who are still doing some great things here. And it's only beginning Susan, it's only beginning.

Susan: That’s great. Sounds like you guys are becoming the next Silicon Valley so to speak.

Ray: Maybe so or some people say Silicon Prairie or whatever but, you know what I like? Yea, you can say that but I think each region of the country offers something a little bit different--maybe a little bit different twist in the way they approach things. Like when you read Steve Blank’s History of Silicon Valley, its interesting to see how a lot of that grew out of the defense industry. Its interesting to see how in the Midwest, because there’s farmers roots and all that stuff, how there’s a different approach here--more of the 37signals. I’ve got to mention 37signals, the birthplace of Rails. The 37signals approach where you are growing organically and based on having customers and you’re using the profits from, your customers’ profits, from satisfied customers to grow your business. I think that’s a very much Chicago-type model and something that 37signals popularizes through their books, through Rework and Getting Real. We’re growing. Rails started in Chicago and of course in Denmark. David Heinemeier Hansson is from Denmark so him and Jason collaborated over the web. So, yea, Chicago is only at the beginning of this. Its really exciting to see all of the things we’ve achieved and then we’re not opposed to partnering with people who are outside of Chicago. I mean, there’s this company called Engine Yard. That’s not in Chicago that we happen to like very much, that we work closely with and that there are several companies in the Chicago area that work with you guys because the whole elasticity thing is--just being able to grow without throwing iron, without throwing hardware to your app, to be able to deal with a publicity spike at the snap of a finger, that’s awesome. That’s awesome. I’m thinking of a few clients we have--one in particular that we have with you--this is, the name of the company is Singles Travel International and my goodness, we moved them from a single server that was breaking--it was really having some trouble and we took them over from another consulting team and we immediately moved them to Engine Yard and they’ve been very happy with the response. We’re using multiple servers in the Engine Yard cloud and when we want to try out new features and show the clients new stuff that we’re thinking about doing there. We just spin up a new server, put it there, it does not effect production at all and when we’re done with it, we just make that test server, that staging server disappear. So we partner with companies outside of Chicago too, just like Engine Yard.

Susan: Thanks so much.

Ray: Yea.

Susan: Well thanks a lot Ray, for spending this time with us, we appreciate it.

Ray: Thank you.

Susan: And we thank you for your time.

Ray: Thank you so much Susan, thank you for having me.