At Microsoft, Don Dodge was known as the software giant’s ambassador to an at-times skeptical startup community. When he was laid off in November, TechCrunch’s Michael Arrington declared, “This is a huge mistake,” but Dodge quickly moved over to Google, where he’s taking on a similar role. (TechFlash has even nominated Dodge for best hire of the year.) Now that he’s starting to settle in, I interviewed Dodge about how Google compares to Microsoft, how he’s enjoying Google products like the rumored Google Phone, and what’s coming in 2010.

VentureBeat: How are you liking the new job?

Don Dodge: I’m loving it. I’m the kind of guy that likes to do things totally new and start over. I’ve done five startups and that’s the ultimate startover. Moving to Google has been exhilarating and overwhelming and awesome, all at the same time.

VB: It sounds like your job at Google is pretty similar to what you were doing at Microsoft, namely trying to convince startups to use your company’s platform.

DD: It is, Anthony. The difference is, at Microsoft my group was focused entirely on startups. Now I’m doing the same thing, but I’m also talking to small and medium businesses and large enterprises about moving to Gmail, Google Apps, and App Engine. I’m helping businesses of all sizes make use of Google platforms.

VB: Now that you’re evangelizing for Google rather than Microsoft, what would you say is the difference in their value to startups?

DD: The principle difference, as you know, is that at Microsoft, the software was pretty expensive — they offered very expensive but very robust products. For startups, in many ways, the price was prohibitive, and that’s why Microsoft did the BizSpark program, to make that transition easier. At Google, most tools like Google Web Toolkit and infrastructure are free, so there’s not a big cost barrier.

VB: It seems like the challenges you’re facing at Google are an inversion of those you faced at Microsoft. At Microsoft, there’s some suspicion and hostility from startups, at least in the Valley. At Google, the resistance you’re facing is more from enterprises.

DD: Well, if there weren’t any challenges, I wouldn’t have a job. My job at Microsoft was convincing startups to pay money to use our tools. At Google, I think the challenges are a little different. It’s about getting small and medium businesses, companies using traditional enterprise software, moving to Gmail and Google Apps and the App Engine. That’s the hill to climb, but having the background at Microsoft really helps.

VB: When you announced the move, you said you were switching from Microsoft products like Outlook to Google products like Gmail. How’s that going? Do you have a favorite?

DD: Oh, it’s Gmail. The thing that surprised me is the Gmail that consumers use is the same email that every Google employee uses.

I’ve found Gmail to be just terrific, particularly the threaded discussions — it’s just so much easier to keep track of discussions and email threads. That’s the first thing. The second thing is, links not attachments. With an email that’s just a link to a Google Doc, you always have the latest version. The third thing was offline Gmail. Now you can go on an airplane, go anywhere offline, and you’ve still got your email and attachments.

The final observation I would make is, over my career, my first email thing was Vax Mail, which was awesome at the time, it was revolutionary. I went from Vax Mail, to Outlook, to Lotus Notes when I was working for Ray Ozzie, then back to Outlook again, and now Gmail. Email is a pretty straightforward application. They have basically the same features, it’s all a question of user interface. I’ve found the transition to Gmail simple, easy, and in many ways better, particularly due to the threaded discussions.

So with a lot of the religion people have [about different products], I’d make the same point about spreadsheets. A lot of people that are my age started with VisiCalc or Lotus 123 and moved to Excel, now we’re moving to Google Spreadsheets. It’s just the next era, the next transition.

VB: You also said you’re going to spend 20 percent of your time on Google Ventures. Can you say what you’re going to be focusing on there?

DD: Yeah, I can say a little bit about that. Being able to work with Google Ventures was really the thing that made this the ultimate dream job for me. I got to do all the same evangelism things, working with startups, businesses, and VCs I had been doing, but there’s a lot of natural synergy between the startups and companies that I work with and Google Ventures making investments in startups and fast-growing companies. It’s just the best of both worlds.

In terms of specifics, this is only my fourth week, so I can’t offer a lot of insight into the kinds of things Google Ventures is investing in. I’ve attended the partner meetings every Monday, and they have a very open and aggressive style. They’ll look at anything, they look at things on the merits, and they are financial investors not necessarily strategic investors. They’re looking to make investments in great startups and great teams. And they’re looking for things where Google can add value to the investments they make.

VB: So are you going to be making investments yourself, or playing more of an advisory role?

DD: It’s an advisory role for now. I’m looking at potential companies and doing due diligence and bringing new deals to them to consider. So for now that’s the way it is, and over time the percentage of time I spend and the level of involvement could increase.

VB: In moving from Microsoft to Google, has your perspective on the startup world changed?

DD: No, I wouldn’t say it’s changed. I would say, if anything, it’s more relevant now than it was. At Microsoft, I was very interested in the next big thing, and at Google the platform groups are very interested in catching the next wave.

I think Google has really placed some big bets on the future. There’s Chrome OS — we all spend the majority of the time in the browser compared to client applications, and Chrome OS is a platform to build applications to run in the browser. Android is another big bet. When it comes to mobile applications, I think in the future, you’re going to go into your office, you’re going to have a flatscreen and a keyboard, and you’re going to take your phone out of your pocket and dock it. And you can decide which applications and data are relevant on your phone and which are in the cloud. The third one is cloud computing itself — Gmail and Google Apps are just providing packaged applications on the cloud. App Engine as an infrastructure to build new applications in the cloud.

Those three areas are the big bets for the future. That’s the future of computing.

VB: Speaking of Android, I know you switched to an Android phone. Which one are you using?

DD: It’s the new one. You’ve seen the press, they gave it to all the employees. It’s awesome. It is night and day from my Motorola Q phone. That was a Windows mobile device, and going from Windows Mobile to Android has been like night and day.

VB: Now that you’ve left Microsoft, how do you feel about the company’s future?

DD: At a high level, Microsoft today is where IBM was in late ’80s, early ’90s. When I was just starting my career, IBM ruled the world. IBM was the dominant computer provider in the world — hardware, software, network, you name it, IBM was king. I think in the late ’80s and early ’90s, we saw that shift and Microsoft became king of the hill. And in 2009, 2010, going forward, Microsoft is sort of like IBM. It’s a longtime company with a great tradition and still very profitable, but it’s not the leader. Microsoft is not making the innovative leaps and coming out with the new stuff. People used to fear IBM and they don’t anymore. More recently, startups and competitors feared Microsoft, and I think over the past five or 10 years since that consent decree, I think that changed the company dramatically. I don’t think startups and competitors fear Microsoft the way they did 10 years ago. Part of it is the natural evolution of companies, part of it is the changing culture from that consent decree.

VB: Those are all of my questions. Anything else you’d like to add?

DD: Well, in terms of 2010 predictions and what’s going to happen next year, I’ve been sort of thinking about that. I haven’t made any yet, but I wanted to bounce a few off you and see what you think.

I think 2010 is going to be the year that Windows 7 really takes off and gets really fast adoption, because a lot of enterprises didn’t go to Vista. They waited for Windows 7 and didnt want to get off XP. I think Windows 7 will see a lot of uptake.

My second prediction is that Office 2010 is going to have the exact opposite problem. I think adoption will be very slow and the reason, I think, is because Office 2007 is good enough. They already own it, it’s bought and paid for, they know how to use it, why spend all the money for Office 2010? It’s going to have a long, hard road.

The third one is, I think 2010 is going to be the year of Gmail and Google Docs and Google Apps. They are ready for prime time, they’re ready for enterprises to adopt, and the price is so compelling.

VB: What do you think about the free, web version of Office?

DD: Yeah, I haven’t seen it, I don’t know too much about it. But I think Microsoft faces the classic innovator’s dilemma. You know, their business model and huge revenues and profits come from the traditional Office. It’s almost cannibalistic of them do a free version or web version. They’re putting their toe in water, but I don’t think they’re going to put a lot of effort behind it, a lot of support behind it. It’s one of those checkoff items when customers ask, “Do you have a free version?” they can say, “Yeah, we have that too.” But I can’t imagine that they’re going to really push that or promote it.

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