Interview with Chris Shipley

February 28, 2010

Series: Entrepreneurial Toolbox

As a founding partner and editorial director in Guidewire Group, Chris Shipley consults with emerging technology companies in the U.S. and Europe to identify market opportunities and accelerate products to market. "What I look for in an early stage company - what appeals to me - is this intersection of a great idea, a real market need, a smart business model, and a passionate team."

Chris Shipley


Chris Shipley is Chair and CEO of Guidewire Group, Inc., a global analyst and advisory firm focused on early-stage technology companies. A leading technology and product analyst for 25 years, Chris is dedicated to the success of technology entrepreneurs, focusing exclusively on identifying market opportunities and building value into the most promising young companies. As the executive producer of the reknowned product launch conference  DEMO from 1996 until September 2009, Chris identified and helped bring to market more than 1,500 products, including WebEx, VMWare,, TiVo, Xfire, Ribbit, and Ironport.

Chris has covered personal technology since 1984 and has worked as a writer and editor for a variety of technology and consumer media. She has won numerous awards for her writing and often has been cited as a leading influencer.

She is on the board and past chairman of the Forum for Women Enterpreneurs and Executives, and is a board member and advisor to a number of early stage companies. Chris holds Bachelor of Arts degrees in Literature and Communication Arts from Allegheny College, Meadville, Pa.


Entrepreneurial Toolbox Interview with Chris Shipley

Lee Kennedy: Hi, this is Lee Kennedy, board member of NCWIT or the National Center for Women Information Technology and also CEO of Boulder Search. Welcome to the next segment in our Entrepreneurial Toolbox Series. It's a series of interviews where we welcome successful entrepreneurs, in which we address a variety of issues, ranging from networking and learning and failures to funding opportunities and all kinds of great things that new entrepreneurs like to hear about. Today with me is Larry Nelson from Hi, Larry.

Larry Nelson: Hi. I'm real excited to be here.

Lee: Well, would you tell us a little bit about W3W3? 

Larry: Well, we're a web-based Internet radio show. We have podcasts, directory and everything else. And we've been doing it for 11 years now. So, that's us.

Lee: Great. And we also have Lucy Sanders, who's the CEO of NCWIT. Welcome, Lucy.

Lucy Sanders: Thanks.

Lee: So, Lucy, Larry and I, today we have with us Chris Shipley. And just to give you a little snippet about Chris, Chris is a writer, analyst, commentator, strategist and has tracked the technology industry for over 20 years. And a well-known fact is that in 2002 Fortune Small Business named Chris perfect Board of Directors, to have on your company board. So, welcome, Chris.

Chris Shipley: Thank you. I'm really glad to be with you today.

Lee: Well, we are thrilled to have you here today, and we'd love to hear a little bit about what's happening with your company, your group, the Guidewire Group.

Chris: Great. Well, the Guidewire Group is, I think, the only global advisory firm that focuses exclusively on early stage companies and the large companies that work with them, who provide strategic services to early stage companies and tools and data to large companies to help them work more effectively with the startups and their ecosystem.

Lucy: Well, you have a lot of background to be able to give us that kind of advice. And so, the questions that we've chosen have a lot to do with giving advice to startups. So, Chris, you started as a writer and, of course, you're a technology analyst and a startup guru as well, what is it about technology that really attracts you? You've been following it for over 20 years. Why?

Chris: Well, I think technology for its own sake is interesting but not particularly fascinating. Where technology intersects with human beings, where it creates opportunity and leverage and support and creates new value in our lives in some fashion, that's what really interests me. Having followed the industry for 25 years now, and seeing, witnessing the real change when this happened in the marketplace, because new technology, whether it's oddly enough a piece of enterprise middleware or it's a device like TiVo, really changed the way people behave in the world. And that's what fascinates me and why I keep getting up every morning working with the early stage companies who are creating those technologies and bringing them into our lives.

Lucy: Well, along the way, what has surprised you the most about technology?

Chris: It's interesting. You recognize the surprises of things by looking backward rather than understanding what kind of surprises they are at the moment. When you think about where we've come in a relatively short period of time and the acceleration of and inclusion of technology into our lives at every level, it's just profoundly, I go back to use the word fascinating, when you think about it. When I started my career, a cellular phone was a large brick that very few people could afford, and now eight year olds are asking mom and dad for their cell phone for Christmas. And it becomes a debate around the family table: what's the appropriate age that you can have a mobile phone? That's a really different conversation and a really different generation of youth that will grow up as a result of just that one technology. So, I guess if you're looking back, I'm really awestruck by the rate of change and the acceleration in that rate of change and how it's really changing and affecting the next generation, next generation, next generation, and creating both a common thread. But also starting to I think create some needs to bridge an understanding of experience.

Lucy: Well, and that rate of change is so dependent on the technology. Don't you think? It seems that working at Bell Labs I was always surprised how long it took for speech recognition to take off, for example, and then how quickly things like mobile took off even when it seemed to us at Bell Labs [laughs] of course that the quality was inferior. [laughter]

Larry: All right.

Lucy: This rate of change is really quite fascinating.

Larry: Yes.

Chris: And it's the right quality. What is good enough? Really, the thing is the accelerator. If you think about MP3 players, pre-iPod, they were hard to use. The ecosystem wasn't really fully in place. You could download music, but there were a lot of issues and challenges around piracy. The player was separate from the media. One could argue that the iPod is not necessarily technically more outstanding, but it hit that really good-enough-to-be-really-useful benchmark and brought all the pieces of the ecosystem together. And that product came out and just completely changed the way people now interact with music. Those of us who get really into the nitty-gritty of the quality of the experience, I think sometimes in the research lab what is perfection often missed the point of what's really going to move the needle and make a product really affect and be effective in someone's life.

Larry: Yes, boy. You know, Chris, you mentioned early about families debating how old they should be before the kids get a cell phone and all. I don't know if you are aware of this, but it takes babies three more months to walk than it did in the past. That's the reason they have to learn how to text while they're walking. [laughter]

Larry: OK. So anyhow, speaking of tech trends, refresh our start-up audience and the other people that are listening, too, that maybe they're going into the next stage of their organization. What are some hot technology trends that are heading our way?

Chris: I think there are some of the usual suspects that you'll hear from a lot of people who follow the markets. I think we'll see a lot continue to happen in real-time web, making applications more accessible, this continuing push into mobility, and these new mobile platforms. There's a plethora of new platforms coming into the market. If you think about when I started in this business, it was a Mac/PC and that was your development choice. Today, am I developing in the cloud? Am I developing for the iPhone or for Android or for a desktop environment? There are five or six, seven or eight kinds of choices now in terms of platforms. What I think of is the proliferation of endpoints as design markers or platforms for development, that's going to continue to push innovation into the market. And certainly the mobility and these sorts of things continue to happen. How do you create better user experience? I think we will see a lot more technology development around better sound, better text input, better multi-touch kinds of UIs--all of these things that are about how this technology becomes more embedded, more easily used, those kind of things. It's a lot of, I think today and for the next maybe let's say 18 months, continuing to push in those areas while really starting to absorb a lot of that change. I think we'll see a lot of interesting innovation bringing all those pieces together.

Lucy: That's interesting because a lot of times people think of new technology as just something new that's never been discovered, but you're talking about refining and improving that will bring about new changes in technology. So that's an interesting way to look at it.

Chris: Yeah, I'm really finding out the difference between invention and innovation. Invention being I just created something that did not exist before. And innovation being: How do I improve and apply and finesse all of these wonderful tools at my disposal to do something that's really new and valuable? I think we're in a period now where there is still a lot of invention, but we're in a period of absolutely rapid innovation where those inventions are being commercialized and applied in new ways.

Lucy: Chris, I want to go back to one of the earlier statements I had made about Fortune Magazine included you as one of the most perfect board of directors. We understand that you consult and work with many, many early stage startups, and we would love to get those little nuggets, those important pieces of advice that you give those startups.

Chris: [laughs] It's interesting because although each startup I think is a unique entity, there are some commonalities. I think primarily among them, it's focus. There are so many things you can do as a startup around your idea, but focusing on things you must do in order to move the needle. I think particularly for very young startups, it's very easy to get distracted by what I think of as the shiny objects-that other opportunity over here or that one little piece of user feedback that might take you down another avenue. I think for startups to be really effective, a continual process of evaluating where they are, what are they trying to accomplish, what can they do, what must they do? Taking things off the table and really staying focused is the best and most regular advice that I'm giving to early stage companies.

Lucy: And other than having a lack of focus as maybe one of the mistakes that you see early stage startups making, is there any other mistake that you consistently see them make?

Chris: I would say that it's maybe less a lack of focus than too wide a focus. People often confuse vision for focus. Vision is how I'm going to change the world with my startup. Focus is how I'm going to get there. To do that, keep that focus in micro-chunkable measurable units in order to understand progress. I think that focus exercise is part of it. I think the other one is it's easy to become discouraged in this marketplace when especially the economy is where it is today, where the venture marketplace is under tremendous strain and is transforming, and to realize that I have this vision and I just don't have the resources to get there. That can be a stalling out point for a lot of companies. I like to say that you always have the resources to do something. Time is a resource. Maybe there's the support of a network. There are lots of different kinds of resources. You have the resources to do something if you stay well focused. It's when you, again, get unfocused and think, "Well, I can't afford to buy the world so I'm not going to buy my little plot of land, either" that you get derailed as a company. You spend a lot of time trying to raise money, play that whole game, and you miss the opportunity to build your business. So I think it's recognizing that smart strategy is about applying what resources you do have to the things you can do to move the needle is number one. I think the other is to help people recognize that, and particularly in this market, revenue is the new venture capital. Going out and working with customers, meeting a need, and getting paid for what you do is business building. If the average fund raise is going to take three to six months minimum, you might as well be out building customer relationships, which will not only accelerate your fundraising but put revenue in the bank in the interim. So relentless focus on drive to revenue would be the third piece of advice.

Larry: Wow! Chris, I'm going to throw you a little curve ball here. [laughter]

Chris: OK.

Larry: I know you're highly invested in what you're doing in every way, but what would a startup have to do to attract you to be its CEO?

Chris: Hm. That's a great question. First of all, I want to say I do what I do because I'm a really bad employee, so I'm not sure... [laughter]

Chris: ...they really want to have me as their CEO. What I look for in early stage companies, one of the things that appeals to me, is this intersection of a great idea, a real market need, a smart business model, and a passionate team. All of those have to be there in sufficient quantity to make me think this would be the thing I'd give up building my own company for. I think we see lots of passionate entrepreneurs who haven't quite figured out how they're going market or they may be passionate about building a company, but not so much about their impact in the marketplace, about moving the needle, about really affecting people's lives in some fashion, or you get a lot of passion about changing the world, but you don't have the right team together to make that happen. I think all four of those elements are really critical in order to attract real talent to your team whether it's me or anyone else.

Larry: Wow.

Lucy: So is that a good answer, Larry?

Larry: That's a good answer. I like that answer.

Lucy: [laughs]

Chris: I passed the curveball test.

Woman 1: Well Chris, we'd love to hear what else is going on, what new books you might have in the works.

Chris: I'm really focused right now on building Guidwire group as the, we hope, premiere advisory firm for early-stage companies and provider of information to the marketplace that works with startups. We've taken the experience that I and others analysts have over 20 years of evaluating and assessing potential in companies and codified into what we call the G/Score. The simplest way to think about G/Score is it's the gaps for early-stage companies--a transparent and objective measurement of a company across seven categories of performance and execution. It proves to be a very prescriptive for early-stage companies and it changes the conversation for the large organizations who want to work with them because it brings things to a - all those instincts, it puts them on a common ground. So we're very busy about the process of propagating G/Score. We'd love to see it become the de facto standard for rating early-stage companies and we're rolling that out across Europe and the United States in a series we called Pitch Slam events to help us bring more people into this; an understanding of the score methodology, have them use the methodology and to begin to collect data on more and more companies. So it's a big effort underway here. And on the second push on the company, we call Studio G, which is really about taking our focus methodology that I spoke of a bit ago and working with early-stage companies to help them over a period of six months really drive value into their company by adopting this methodology, learning how to use it and having access to our mentor networks and our analyst strategists with the goal of building a two to five action improvement in the value of your company in the course of that six months. So we try to get companies focused, help them execute and build the business. So we'll be talking a lot more about Studio G as the year unfolds. But those are the big efforts within Guidewire. I'm always noodling on one book project or another. I suppose there's one in there somewhere about entrepreneurship that is working its way out. So we'll see what we can do there as well.

Lucy: That's exciting.

Lee: Well, that would be awesome. We are especially interested in woman as IT entrepreneurs.

Larry: Yeah. But sign me up, too. [laughter]

Chris: It will appeal to your feminine side, Larry.

Larry: OK, yeah. I do have four daughters, so I know what you mean.

Lee: That would be awesome. That would be awesome.

Chris: It's interesting. I'm very interested, as I know you are, about women and entrepreneurship, particularly in the tech sector. I think there are a lot of questions about why aren't there more women. Certainly and sadly, I can count on my available digits the number of women founders and CEOs that come through my office in the course of a year. The numbers just aren't there. But I think we shouldn't mistake that for a belief that women aren't entrepreneurial or that they're not creating businesses. In fact, women are outstanding entrepreneurs. Lots of data would demonstrate that their performance metrics actually outstrip their male counterparts. I think the real key, though, is for men to remember that the best-performing teams are ones that are integrated teams. So when you're thinking about who your next co-founder should be or who do you need to bring into your executive team, a bias toward bringing a woman into the team is actually a bias toward improving your business.

Lee: Absolutely. That is a great way to put it.

Larry: And that's what NCWIT is all about.

Lee: Chris, thank you very much. This was very interview. Thanks for taking time away from your busy day to talk to us.

Chris: Oh, it's always my pleasure. I really appreciate the work you're doing and I wish you all great luck with that.

Lee: Well, and just a reminder to listeners to pass this on to others who might be interested. You can find it at as well as Thank you.

Larry: Thanks, Chris.

Lucy: Thank you, Chris.

Chris: Thank you all. [music]