Day Three kicks off with James Gleick, the man who has written the book of the year, at least if you are a fan of our conference theme. As I wrote in my review of “The Information,”

Gleick’s book tells the story of how, over the past five thousand or so years, mankind has managed to create symbols which abstract meaning and intent into forms that are communicable beyond time and space….The work really picks up speed as it describes the rise of early telecommunications, the role of information in mid century warfare, and the birth of both genetic sciences and the computing industry. In the end, Gleick seems to be arguing, it’s all bits – and I think most of us in this industry would agree. But I think Gleick’s definition of “bit” may differ from ours, and while it may be esoteric, it’s there I want to really focus when he visits Web 2 in October.

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(image) Early this year I wrote File Under: Metaservices, The Rise Of, in which I described a problem that has burdened the web forever, but to my mind is getting worse and worse. The crux:

“…heavy users of the web depend on scores – sometimes hundreds – of services, all of which work wonderfully for their particular purpose (eBay for auctions, Google for search, OpenTable for restaurant reservations, etc). But these services simply don’t communicate with each other, nor collaborate in a fashion that creates a robust or evolving ecosystem.”

I noted that the rise of AppWorld only exacerbates the problem (apps rarely talk to each other or share data).

This must change. Not due to my philosophical problems with a closed web (though I do have that problem) but because yesterday, while driving back from an afternoon in the Valley, I had an idea for a new service, which for now I’ll call Tapestry, for lack of a better name. And then I got depressed: I figured making such a service would be really, really hard to do. And it shouldn’t be. And I hate getting depressed so quickly after having a fun idea.

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Day Two at Web 2 Summit ends with my interview of Steve Ballmer. Now, the last one, some four years ago, had quite a funny moment. I asked Steve about how he intends to compete with Google on search. It’s worth watching. He kind of turns purple. And not Yahoo purple.
So sure, I’m hoping for more classic Ballmerisms this time around, and there’s plenty to talk about. From investors calling for his head (Microsoft generates impressive cash and dividends, but could hardly be called a growth stock), to the future of Windows, my only concern is we’ll run out of time.
Because I want to talk about the Xbox SDK, Microsoft’s cloud strategy, Bing, Windows 8, the Facebook and Twitter partnerships, the Skype purchase, Yahoo (again), tablets, the Nokia deal…

But enough of my questions. What do you want to ask one of the most important CEOs in the world?

As an extra incentive, I’ll be picking the best three questions from these series of posts (see below and watch for more). The authors of those questions will get complimentary passes to Web 2 – a more than $4000 value. So get to commenting, and thank you!

Previously: Mark Pincus, John Donahoe, Marc Benioff, Dick Costolo, Michael Dell, Mary Meeker, Michael Roth. Next up: James Gleick.

Thanks to Brian Solis for taking the time to sit down with me and talk both specifically about my upcoming book, as well as many general topics.

What’s the CEO of a major advertising holding company doing at Web 2 Summit? Well, come on down and find out. Marketing dollars are the oxygen in the Internet’s bloodstream – the majority of our most celebrated startups got that way by providing marketing solutions to advertisers of all stripes. Think about it: Google, Facebook, Twitter, Foursquare, Groupon – all provide channels between customers and brands.

So it only seem fitting that invite a man responsible for more than $6.5 billion in marketing-driven revenues (and that’s not advertising spend, that’s revenues after spend). Michael Roth runs the Interpublic Group of Companies, which include scores of specialized agencies, from Cadreon on the automated buying side of things to McCann, Lowe, and DraftFCB. The company employs more than 40,000 people around the world.

Marketing is changing dramatically as the Internet becomes *the* medium connecting brands and consumers. It’s also a key indicator of economic health – as goes marketing spend, so goes the economy. I’ll be asking Roth about the role digital has played in his business, as well as how he sees the rise of companies such as Google and Facebook.

What do you want to learn from a top executive in the world of marketing?

As an extra incentive, I’ll be picking the best three questions from these series of posts (including Paul Otellini, Mary Meeker, Michael Roth, Steve Ballmer, James Gleick, Vic Gundotra, and Reid Hoffman, among others.) The authors of those questions will get complimentary passes to Web 2 – a more than $4000 value. So get to commenting, and thank you!

Previously: Mark Pincus, John Donahoe, Marc Benioff, Dick Costolo, Michael Dell, Mary Meeker . Next up: Steve Ballmer.

For the first time in eight years, Mary Meeker will let me ask her a few questions after she does her famous market overview. Each year, Mary pushes the boundaries of how many slides she can cram into one High Order Bit, topping out at 70+ slides in ten or so minutes last year. But given her move this year from star Internet analyst at Morgan Stanley to high-profile VC, I asked if Mary might spend another ten or so minutes with us to answer a few questions. She graciously agreed.

Kleiner Perkins has focused on social and mobile in a big way over the past year, raising significant funds, investing in Twitter, Square, Spotify, Klout, Path, and many more. But the firm does much more. Mary is a sharp observer of trends in our industry, and I am looking forward to picking her brain, if only for a few minutes. Sow hat do you want to hear from her?   

As an extra incentive, I’ll be picking the best three questions from these series of posts (including Paul Otellini, Mary Meeker, Michael Roth, Steve Ballmer, James Gleick, Vic Gundotra, and Reid Hoffman, among others.) The authors of those questions will get complimentary passes to Web 2 – a more than $4000 value. So get to commenting, and thank you!

Previously: Mark Pincus, John Donahoe, Marc Benioff, Dick Costolo, Michael Dell. Next up: Michael Roth.

Foursquare co-founder and CEO Dennis Crowley will give his first 1-1 interview on the Web 2 stage on the conference’s second day, following a morning of High Order Bits and a conversation on privacy policy with leaders from government in both the US and Canada. After Crowley will be a conversation with noted investor Ben Horowitz, then a discussion with leaders from both Visa and American Express.

But let’s focus on Crowley for this post. He and his co-founders have a tiger by the tail in Foursquare, the location-based leader that so far has resisted either demolition or acquisition by larger players like Google and Facebook. The still-young company (two+ years old) recently celebrated its billionth check-in, not to mention a $600 million private valuation. That kind of pressure is continuous and very real, I’ll be asking Crowley about living up to his investor’s expectations.

I’ll also be asking about business model, of course. Foursquare has done a ton of deals with many different kinds of brands, including publishers, but so far does not have a model that scales – though it’s clearly building out a platform for merchants. This puts it in the Groupon business, so to speak, at least in terms of competing for retailers’ time and treasure. So I will clearly be asking about that. Too bad Groupon had to cut out of the agenda (IPO issues), or I could have asked their CEO about Foursquare.

While I could go on, this is where I aks for your input. What do you want to hear from Crowley, about his company?   

As an extra incentive, I’ll be picking the best three questions from these series of posts (including Paul Otellini, Mary Meeker, Michael Roth, Steve Ballmer, James Gleick, Vic Gundotra, and Reid Hoffman, among others.) The authors of those questions will get complimentary passes to Web 2 – a more than $4000 value. So get to commenting, and thank you!

Previously: Mark Pincus, John Donahoe, Marc Benioff, Dick Costolo, Michael Dell. Next up: Mary Meeker.

Not unlike Steve Jobs back in the 1990s, Michael Dell returned to the helm of his company at a crucial moment, when his namesake was seemingly rudderless. Back in 2007, Dell was losing marketshare to HP, Apple had not yet proven the monster it has since become in mobile, and tablets were something used on factory floors.

Since then, Dell has redoubled its efforts in tablets and mobile, reworked its product line to compete with Apple’s resurgent MacBooks, but seen his stock price only slightly recover since the 2008 recession. Why? Dell faces competition from China, for one (Lenovo has claimed it will overtake Dell in market share this year), and from tablets, for the other (Amazon’s new Fire might hurt Dell’s ultralightweight offerings, and its Streak Android tablet).

That said, Dell has to be happy about the on again, off again approach taken to the PC business by its primary competitor, HP.

In short, we’ll have much to discuss – Amazon, Apple, Android and Google, HP – and the future of device computing in general. Not to mention what it’s like to come back and run a company you had once thought you had handed over to a trusted lieutenant.

So I’d love your input. What do you want to hear from Dell, about his company?   

As an extra incentive, I’ll be picking the best three questions from these series of posts (including Paul Otellini, Dennis Crowley, Mary Meeker, Michael Roth, Steve Ballmer, James Gleick, Vic Gundotra, and Reid Hoffman, among others.) The authors of those questions will get complimentary passes to Web 2 – a more than $4000 value. So get to commenting, and thank you!

Previously: Mark Pincus, John Donahoe, Marc Benioff, Dick Costolo. Next up: Dennis Crowley.

Today Federated Media Publishing announced it has acquired Lijit Networks, a world-class business partner to online publishers based in Boulder, Colorado. This combination is the result of literally months of work, including a ton of strategic thinking that dates back to Federated’s acquisitions of Foodbuzz, Big Tent, and TextDigger last year.

With reach into nearly 200 million uniques, Lijit is a major player in what we at Federated call “the Independent Web.” While Lijit serves all stripes of publishers, it shines with smaller sites whose size often means they get ignored or minimized by other network players. Lijit not only provides top-tier advertising services (it’s growing like crazy, see Lijit CEO Todd Vernon’s post here), but it was born as a service to publishers – with great analytics and search (I use it here on Searchblog). In the past year, Lijit has built out an impressive set of offerings in the technology-driven display market – a space rife with acronyms like SSP (supply side platforms), DSP (demand side platforms), and RTB (real time bidding). This ecosystem is increasingly complex, and Lijit is committed to helping independent publishers thrive within it.

But Lijit is more than great technology and services. It’s a passionate group of people who share our vision of bringing service and value to the constellation of “small pieces loosely joined” that, taken together, comprise the true voice of the web. When I traveled to Boulder and met the team, including CEO Todd Vernon, COO Walter Knapp, and lead investor Seth Levine of the Foundry Group, I knew we had more than a business deal at hand. I don’t know how else to put it – these are really good people, and I can’t wait to work together to write the next chapter of our work together. Congratulations to all.

Read more about the Lijit deal on the FM site, the Lijit blog, and over at All Things Digital. Congrats to all!

Our dinner conversant at  Web 2 Summit is Dick Costolo, the CEO of Twitter. Why pick Costolo for dinner? Because he’s pretty damn funny, besides being the CEO of Twitter, that’s why. And when it comes to dinner, you need some levity.

Not that Twitter doesn’t have some serious issues to talk about. I’ve outlined them in full throat on this site; if you want the latest, read The Future of Twitter Ads, for a start.

Dick and I have been round the maypole a few times, both onstage and in life. My company FM had a deal with his previous startup, Feedburner, and we remain colleagues and friends. Of course, that won’t stop me from channeling the Summit audience’s important questions. Or yours. So I’d love your input. What do you want to hear from Costolo, and about Twitter?   

As an extra incentive, I’ll be picking the best three questions from these series of posts (including Paul Otellini, Michael Dell, Dennis Crowley, Mary Meeker, Michael Roth, Steve Ballmer, James Gleick, Vic Gundotra, and Reid Hoffman, among others.) The authors of those questions will get complimentary passes to Web 2 – a more than $4000 value. So get to commenting, and thank you!

Previously: Mark Pincus, John Donahoe, Marc Benioff. Next up: Michael Dell.