According to several sources, Yahoo’s SVP of U.S. Revenue and Market Development Joanne Bradford (pictured here) is planning on leaving the Internet giant to take a new position as chief revenue officer of online content upstart Demand Media.

The surprise move is sure to have reverberations throughout the online advertising arena, but more so at Yahoo (YHOO), where Bradford’s job encompasses a wide range of key revenue-generating duties.

She has also been tapped as one of the execs to play a key role in the recently approved search and online ad partnership with Microsoft (MSFT).

Yahoo declined to comment. BoomTown has also contacted Demand and is awaiting comment.

Bradford had actually once been a Microsoft exec, serving as VP and chief media officer of MSN Media Network. She had worked at BusinessWeek before that.

Bradford came to Yahoo in the fall of 2008, at the tail end of the tenure of Co-founder Jerry Yang, who stepped in as CEO after the previous CEO Terry Semel departed.

Immediately previous to her job at Yahoo, she had been helming national ad sales at then-trendy Los Angeles-based ad services company Spot Runner.

Demand will be her second time going from a large company to more of a start-up.

But–unlike the troubled Spot Runner where Bradford worked for only six months–Demand has been on a growth tear of late with a social media strategy that is also being pursued by AOL (AOL) and others.

It owns heavily trafficked sites, such as how-to juggernaut eHow and the health- and fitness-focused Livestrong.com, putting Demand in the list of the top 20 Web properties.

It reportedly has about $200 million in annual revenue–mostly from advertising, but also from a domain registration business–and is profitable with several hundred employees.

The Santa Monica, Calif.-based company is headed by serial entrepreneur Richard Rosenblatt (pictured here), former chairman of Intermix Media. Intermix was the parent company of MySpace, which was sold to News Corp. (NWS).

Armed with an astonishing $355 million in funding from a range of prominent investors, he has been trying to fight some mainstream media depictions of his social media content company, especially one report that called Demand a “content mill.”

Via its Demand Studios, the company uses an army of freelancers to produce all kinds of content for its sites and others, using a complex automated system, but which also includes vetting and editing.

In fact, irked at the characterization of Demand as a content spammer, Rosenblatt even issued a manifesto for Demand in January.

“There has been so much misinformation about our model and what we actually do, that I thought it was a good idea for our company and those who work for us to lay out our principles,” said Rosenblatt in an interview with me at the time. “We are so different from traditional journalism, which I have nothing but admiration for, so it was time to make people understand that.”

The role of Demand Media, said Rosenblatt, was to help readers solve problems, laugh and get good advice, while figuring out how to create a profitable media business in the digital age.

(Walt Mossberg and I have invited Rosenblatt to share the stage at the eighth D: All Things Digital conference this June, along with former Wall Street Journal editor Paul Steiger, who is trying to save investigative journalism at a nonprofit called ProPublica, to talk about it all.)

If Rosenblatt is successful, Demand appears to be aiming for an IPO or merger with another company. Ironically, Demand has also been eyed by Yahoo in the past, as a possible acquisition.

Nabbing a top Web exec like Bradford from Yahoo is obviously a definite step in raising the stakes for Demand with big, established advertisers.

That’s because Bradford is well-regarded in the industry and is a prominent player. She recently signed a high-profile deal with Hollywood producer Ben Silverman to create premium content for Yahoo.

Bradford’s departure will be seen, both internally and externally, as a definite blow to turnaround efforts by CEO Carol Bartz. Bradford currently reports to Hilary Schneider, EVP of Yahoo’s U.S unit.

My reporting does not indicate that Yahoo’s top brass know about Bradford’s expected move, so it is not clear who would replace her at the Silicon Valley icon, which has been hard hit by an exodus of talent over the last two years.

Internal candidates could include 11-year Yahoo veteran Mitch Spolan, VP of North American sales, or Seth Dallaire, a former Microsoft exec whom Bradford brought to the company last fall as VP of mid-market sales, a newly-created role responsible for all mid-market sales efforts across search and display advertising.

More to come, obviously…

Yesterday, for instance, Omnicom (OMC) reported that “organic revenue”–an accounting term that factors out wildcards like currency fluctuation and acquisitions–dropped 6.6 percent in the last quarter.

Today we hear from heavyweights Interpublic Group (IPG) and WPP, which have similar tales to tell. Interpublic reports a 5.6% decline in organic revenue; WPP says 5.8 percent.

Not mentioned in WPP’s three-month update: Any info about its sensational lawsuit against ad start-up Spot Runner, which it accuses of being a privately held pump-and-dump scheme. While the Spot Runner imbroglio is sexy, it has no impact on the company’s top or bottom lines.

But Omnicom management made hopeful noises yesterday about a recovery that might appear by the end of the year, and WPP has the same supercautious optimism: “The first half of 2009 will clearly be very difficult, with the second half, although continuing to be tough, likely to improve relatively. Any recovery, of sorts, will probably come in 2010.” Small comfort, but I’ll take it.

As everyone knows by this morning, Spot Runner–the heavily-funded and once-hyped online-offline advertising agency–is being sued by one of its more prominent investors.

Ad behemoth WPP, which is making a variety of harsh allegations in a lawsuit filed about two weeks ago, is saying it is still not too big to be snookered by the start-up’s top execs and some of its other investors.

WPP (WPPGY), which has been quite active in making digital ad investments over the last several years, is alleging that Spot Runner sold over $54 million in “secondary” shares to line its own pockets without telling WPP much, all while losing money, running out of funding and not building a sustainable business.

The lawsuit essentially paints an ugly picture of Spot Runner as the Bernie Madoff of Web 2.0.

In its strongest phrasing, the lawsuit alleges:

“Rather than working to make Spot Runner a successful and profitable venture, they perpetuated a ‘pump-and dump’ scheme in which they aggressively promoted the Company to new investors (often by promoting that WPP was an investor in and supported of the Company) and then sold new investors large quantities of their own secondary shares at ever-increasing valuations. Such secondary sales were accomplished surreptitiously and without disclosures to Investors required by the controlling Investor agreements or federal and state securities laws.”

Those named in the suit include: Spot Runner CEO and co-founder Nick Grouf, CTO and co-founder David Waxman, venture investors Battery Ventures and Index Ventures, and board members, such as former AOL exec Robert Pittman.

This is obviously a bad turn of events for Spot Runner, which is currently reeling from the advertising downturn too.

Before that, it had gotten over $100 million in funding from a strong slate of investing luminaries.

Investors included international media giants Daily Mail and General Trust and Grupo Televisa, investment company Legg Mason Capital Management (LM) and luxury conglomerate Groupe Arnault/LVMH.

Spot Runner’s previous investors are Allen & Company, Battery Ventures, Comerica Bank (CMA), Lachlan Murdoch, Vivi Nevo, Capital Research and Management, CBS (CBS), Index Ventures, Interpublic Group (IPG), Tudor Investment Corporation and WPP.

All that money had, when times were good, given Spot Runner an eye-popping valuation upward of $500 million.

And that’s the very kind of bubble economics that apparently allowed some at the company to make those lucrative secondary sales the lawsuit alleges, with lots of demand to get in to the latest hot start-up.

To be clear, such sales are not uncommon at tech start-ups in Silicon Valley, often done to allow entrepreneurs to take some money off the table, especially if there is no clear path to liquidation.

But the scope of the sales alleged is quite unusual, with Grouf getting half the proceeds of the transactions, which were made from early 2006 to early 2008.

That said, WPP–which is seeking $11.5 million in damages, as well as legal fees, after investing $10 million–leaves itself open to its own tsk-tsking, since it finally got to participate some in the sales too, dumping $900,000 worth of shares in the last one.

That makes it seem like WPP is just miffed that it did not get enough while the getting was good, which is underscored by the small amount of money being asked for in the lawsuit, in comparison to the large and loud accusations.

Worse still, perhaps, for everyone involved, is the suit’s revelation that Spot Runner was not the revenue geyser it had touted itself as being–which should not come as a huge shock to anyone who has followed any Web 2.0 company in an even cursory way.

Very few, including the star, Facebook, make money, as BoomTown and others have pointed out a lot to little interest.

The lawsuit says the profit-free Spot Runner had $5 million in revenue in 2007 and $9 million in 2008. It alleges too that the company only has $20 million left of its funding and is spending $35 million to $45 million a year.

That’s because Spot Runner was trying to create a new online ad system, which was essentially a do-it-yourself model that tries to iron out inefficiencies in the buying and selling of advertising and bridge the gap between the traditional and online ad markets. It has since changed its strategy and is working on other products, such as a digital-media buying platform called Project Malibu.

Other than Spot Runner’s statement that it would defend itself vigorously, there were mostly no comments all around.

“This situation is unfortunate; we had hoped that we would have had a long relationship with WPP. We believe the claims are without merit and we will vigorously defend against them, including taking all necessary legal action to protect Spot Runner’s reputation,” said a Spot Runner spokeswoman in a statement.

But one source close to the Spot Runner side, while not addressing the specific allegations, noted in an interview with me that what looks bad now did not then:

“These are different times and things look differently.”

You can say that again. And again after that.

As point of that fact, check out a video I did, below, with Grouf last July at Spot Runner offices in Los Angeles, right after it had gotten one of its giant piles of money. (Grouf is pictured here.)

This video took place right after a lot of the transactions that the lawsuit alleges, which makes sense since Spot Runner was the hot start-up at that moment and many would have been trying to get into the action.

I met Grouf many years ago when he–along with Waxman–founded PeoplePC and Firefly Networks.

Grouf sold the struggling PeoplePC–which hawked computers bundled with an online service–to Earthlink (ELNK) in 2002 for $10 million and assumption of $35 million in liabilities, in a Web 1.0 meltdown deal that followed a disastrous IPO.

But with a hot new start-up, everything looked pretty again, perhaps too pretty, for Grouf.

As I wrote at the time about the hype, which including rumors of Spot Runner being sold for big bucks to Google (GOOG) or Microsoft (MSFT):

“This is its biggest burden, I think, setting expectations very high for what is still a little start-up…Who knows whether the company will be able to overcome its hype, but time (and money) will tell.”

Obviously, we can tell a lot more now.

Here’s the Grouf video (the full lawsuit text and a memo Spot Runner sent to employees about it are also below):

Here is the full lawsuit (click on + button to zoom in):

And, finally, here is the letter Spot Runner sent to employees, who have suffered from layoffs, about the lawsuit:

Team,

As you may have heard, WPP, a minority shareholder (less than 3%) in Spot Runner since 2006, filed a lawsuit against the company and its board members primarily related to the sale of Spot Runner stock and Spot Runner’s communications with WPP. This situation is unfortunate, as we appreciate and value the relationships we have with all of our investors and we had hoped for a long and supportive relationship with WPP. We believe these claims are without merit and we will vigorously defend against them, including taking all necessary legal action to protect Spot Runner’s reputation.

We feel strongly that WPP’s complaint contains many baseless accusations and we want to give you a broader perspective on the matter. This lawsuit is unrelated to our products and services–it is centered on legal agreements entered into with WPP, a sophisticated investor, regarding the way that shareholder stock sales were handled. WPP alleges that Spot Runner’s board members failed to disclose to WPP the stock sales by shareholders, allegedly in violation of the board’s obligations to stockholders, among other things.

We are confident that Spot Runner complied with all of its obligations under the various shareholder agreements. When these sales occurred, there was overwhelming demand for Spot Runner stock and the company did not want to dilute existing shareholders by issuing new shares. Therefore, the founders (in 2006) and the board members and other preferred shareholders (in 2007 and early 2008) agreed to make room for important, new investors and respond to their desire to invest in Spot Runner by selling their own shares. In 2007 and 2008, WPP and other preferred shareholders were given notice that the sales were occurring and they had the opportunity to participate in the sales. In fact, WPP signed various documents acknowledging this opportunity.

Spot Runner and all of its employees conduct business with the utmost integrity. Our team, technologies, and products and services are core assets of which we can all be proud. It is because of your hard work that we have come this far. To that end, we continue to drive hard toward successfully launching Project Malibu and realizing its full potential. You also should know that our board members remain majority shareholders in Spot Runner–a concrete sign of their commitment to and confidence in the business.

Our outside counsel will work with the board and management team to develop a formal reply, which ultimately will be filed with the court. These legal proceedings should not affect our day-to-day operations.

We are grateful that we can count on you to remain focused on serving our clients and partners to the best of your abilities.

Thank you again for all that you do for Spot Runner.

About a month ago, BoomTown reported that MSN executive producer and general manager Jeff Dossett (pictured here) was contemplating joining Yahoo.

Microsoft (MSFT) released a statement that day saying Dossett was indeed stepping down from his MSN duties, as I had posted, but noted that he was staying put at the software giant.

Oops, it looks like I was right in my initial report: “The Secret Microsoft Invasion of Yahoo Continues: MSN GM Headed There Soon?”

Dossett has accepted a job as SVP, U.S. Audience at Yahoo, Yahoo (YHOO) said in a press release this afternoon.

“I am very excited about this new leadership opportunity at Yahoo,” wrote Dossett in an email to me. “Of course, I have great respect for my many friends and colleagues at Microsoft and I wish them well.”

But is the hire linked to my report earlier today of Yahoo Media Group SVP Scott Moore leaving?

You betcha, as Governor Sarah Palin says.

While the company had already been deep in conversations with Dossett for another job, as head of business development, management scrambled after Moore reportedly told Yahoo of his plans to leave a week ago.

After BoomTown this morning reported that Moore, as well as Yahoo News general manager Alan Warms, were departing later this week, Yahoo confirmed the departures this afternoon.

Dossett will report to Hilary Schneider, executive vice president of Yahoo U.S., and fill the role previously held by Moore, although the title is different. Yahoo said Moore was leaving “to pursue other opportunities.”

A Yahoo spokesman also said later about Warms:

“We’ve worked with Alan over the last couple of months on an orderly transition plan of his responsibilities over to Neeraj Khemlani, who will continue to lead Programming & Development for News & Information at Yahoo. We wish Alan much success in his future endeavors and know that Neeraj will continue driving Yahoo News to even greater success.”

Dossett will have presumably have purview over all that and more.

A longtime and experienced mountain climber, he has been one of the more senior digital execs at Microsoft.

The reason given for Dossett’s departure from Microsoft, announced internally in mid-September, was to also “pursue other opportunities” (I still love this phrase, as oily as it is.)

As I wrote then: “While the hire is not yet complete, that apparently means that he is likely going to rival and onetime Microsoft quarry Yahoo as a senior exec.”

It has all been an interesting digital-musical-chair trend, in fact. Also last month, another former Microsoft big shot, Joanne Bradford, started her job as Yahoo’s top U.S. ad sales exec.

Bradford came to Yahoo after a very short stint as national ad sales head at the trendy Los Angeles start-up, Spot Runner.

Previous to that, Bradford (pictured here) had been at Microsoft for many years, most recently as VP and chief media officer of MSN Media Network.

While at Microsoft, Jeff Dossett was a close colleague of Bradford, so his moving to Yahoo is probably not that much of a surprise.

Outgoing Yahoo Media Group SVP Moore, who has been at Yahoo since 2005, is another former Microsoft digital exec, where he worked all over the company.

In his job at MSN, Dossett was the lead for audience, content and programming strategy and execution in the U.S.

He had worked at the company since 1991, in a variety of sales and marketing jobs in Canada, and later worked on strategy and business development for MSN.

Dossett was also CEO of Carpoint, now MSN Autos, and was GM of its real estate arm.

He also took two years off from Microsoft in 2002 to climb the highest mountains on each of the seven continents, finally reaching the summit of Mount Everest in May of 2004.

Dossett reached the summit of Everest again for a second time this past May.

Here is Yahoo’s press release about his appointment in its entirety:

JEFF DOSSETT JOINS YAHOO! TO LEAD US AUDIENCE BUSINESSES

In 2002, Dossett took two years away from his career at Microsoft to pursue his passion for adventure with a goal to climb the highest mountain on each of the seven continents, known as the “Seven Summits.” Reaching the summit of Mount Everest on May 24, 2004, Dossett became the third Canadian in history to successfully complete the Seven Summits. On May 22nd, 2008, Jeff became the second Canadian in history to reach the summit Mount Everest for the second time. He serves on the Board of Advisors of VillageReach (www.villagereach.org), GOOD Worldwide Inc. (www.good.is), and Live Mocha (www.livemocha.com). Dossett holds a degree in business administration with honors from the Richard Ivey School of Business at the University of Western Ontario in Canada.

A longtime and experienced mountain climber, Dossett (pictured here) has been one of the more senior digital execs at Microsoft.

The reason given for Dossett’s departure from Microsoft (MSFT), announced internally this afternoon, was to “pursue other opportunities.”

While the hire is not yet complete, that apparently means that he is likely going to rival and onetime Microsoft quarry Yahoo as a senior exec.

It is an interesting digital-musical-chair trend, in fact. On Monday, another former Microsoft big shot, Joanne Bradford, will start her job as Yahoo’s top U.S. sales exec.

Bradford came to Yahoo (YHOO) after a very short stint as national sales head at the trendy Los Angeles start-up, Spot Runner.

Previous to that, Bradford (pictured here) had been at Microsoft for many years, most recently as VP and chief media officer of MSN Media Network.

While at Microsoft, Jeff Dossett was a close colleague of Bradford, so his moving to Yahoo would not be that much of a surprise.

But one has to wonder what other Microsoft execs Bradford can entice to come to Yahoo, especially given that CEO Jerry Yang is reportedly interested in aggressively beefing up his executive ranks after more than a year of employee attrition due to all the turmoil at the company.

Current Yahoo Media Group SVP Scott Moore, who has been at Yahoo for several years now, is another former Microsoft digital exec.

What Dossett would do if he takes a job at Yahoo is unclear.

But, in his job at MSN, Dossett was the lead for audience, content and programming strategy and execution in the U.S.

He has worked at the company since 1991, in a variety of sales and marketing jobs in Canada, and later worked on strategy and business development for MSN.

Dossett was also CEO of Carpoint, now MSN Autos, and was GM of its real estate arm.

He also took two years off from Microsoft in 2002 to climb the highest mountains on each of the seven continents, finally reaching the summit of Mount Everest in May of 2004.

Dossett reached the summit of Everest again for a second time this past May.

While the pair (pictured here, Schneider on the left and Bradford on the right) would not give specifics about how Bradford was hired, they both noted that they had gotten to know each other over the past year.

And Bradford added that she had met Yahoo (YHOO) President Sue Decker at a poker table several years ago while attending a women’s executive conference run by Fortune magazine.

“I won,” said Bradford proudly. “I beat her and everyone else [at the table].”

How much does BoomTown like a person who insults her uber-boss’s card-playing skills before she even starts?

Very much!

Actually, sharp gambling skills and a little in-your-face style are probably just what Yahoo needs, as the U.S. economy continues to tank and the company tries to recover from the Microsoft (MSFT) takeover debacle.

Combined with management drift and employee turmoil over the last year, Yahoo’s ad business has suffered accordingly.

“I had a laser-like focus on bringing in Joanne,” said Schneider, who said she always asks ad clients who most impacts their online strategy and Bradford’s name kept popping up. “There was a kinetic energy that made it a good fit.”

Bradford is taking over the job of Dave Karnstedt, who is headed to Silicon Valley VC firm Redpoint Ventures as an executive-in-residence. His departure has been long rumored internally.

According to sources, Bradford was unhappy at Spot Runner, the ad-services start-up that has received truckloads of funding, and even more attention when Bradford arrived.

Whatever the case, the former Microsoft exec left her job as national ad sales chief at Spot Runner, where she arrived just six months ago, to take the position of SVP of U.S. revenue and development at Yahoo.

Bradford will oversee sales, market development for advertisers, small business and HotJobs at Yahoo. She will report to Schneider, who is EVP of Yahoo’s U.S unit.

It will be a very tough gig. Yahoo is facing that soft U.S. economy, a weakened stock price after the takeover attempt by Microsoft and justifiable questions among advertisers about its effectiveness, as other sites like Facebook grow faster and with more attractive demographics.

Yahoo is likely to also have to deal with new regulatory scrutiny of its ad businesses, since it was reported yesterday that the Justice Department might block the deal Yahoo recently struck to outsource some of its ad sales to Google (GOOG).

Bradford insisted that Yahoo was still a major force, underscoring that for all its troubles, the company remains one of the top online ad sellers: “My approach has always been about giving advertisers the product they want. … Yahoo has a lot of assets for me to play with.”

Schneider added that the job Bradford has is larger than Karnstedt’s, in order to be able to offer ad clients as many different kinds of Yahoo ad product as possible in an integrated solution.

“It is a different role in that it aggregates all of ad revenue … and touches teams in all of our ad businesses,” said Schneider, who noted Bradford’s job does not include its overseeing its publishing relationships, including a controversial recent deal with Google. “It’s the whole magillah.”

And Bradford knows from gorillas. Previous to Spot Runner, she was a VP and chief media officer of MSN Media Network and has worked at the software giant for a long time.

At Yahoo, where she will start in two weeks, she will not be the only former Microsoft exec–content head Scott Moore, who also reports to Schneider, was a longtime exec there.

It’s a sneaky kind of Microsoft invasion, if you think about it.

Bradford, who left Microsoft right after it made the now-failed bid for Yahoo, said she looks forward to wrangling with her former company in the ad market, especially now that Yahoo has to carve out new roads following its decision to resist.

“Everyone needs good competition, and it will be fun to compete [with Microsoft],” said Bradford. “I think Yahoo is at an interesting point of changing and growing its businesses … but it is still in a leadership position and there is a story to be told around that.”

The departure of Dave Karnstedt, who took over last year when longtime Yahoo ad sales exec Wenda Millard left Yahoo in the first of many controversial partings, has been long rumored internally.

(In fact, I have driven one of Yahoo’s PR people crazy in recent months trying to verify a persistent tip I had been getting that he was headed out the door.)

Karnstedt will be joining Redpoint Ventures, a Silicon Valley venture firm, as an executive-in-residence.

And, in a rejiggering and addition of duties at Yahoo (YHOO), Karnstedt’s job and more is going to Joanne Bradford (pictured here), a longtime and well-known Microsoft (MSFT) exec who decamped from the software giant to helm national ad sales at trendy ad services start-up Spot Runner just six months ago.

There have been rumors swirling that Bradford was unhappy at the smaller company after working at the giant Microsoft.

She was EVP of National Marketing Services, focused on national advertisers, for Spot Runner, joining in a high-profile move in March. Previous to Spot Runner, Bradford was a VP and chief media officer of MSN Media Network, and had worked at BusinessWeek before that.

In any case, the move will be seen as a blow to Spot Runner, which recently did some unusual layoffs, despite receiving a large slug of cash from investors.

(Here is a post and video I did on a recent trip to Spot Runner, including an interview with its CEO Nick Grouf.)

“I am going back to my entrepreneurial, build-something roots,” Bradford told me at the time she joined Spot Runner. “There is such inefficiency in buying and selling of advertising and someone has to solve that, both for big companies and small ones.”

Well, welcome to Yahoo, Joanne, which could use a little efficiency in its buying and selling of ad sales!

Seriously, Bradford will now will take over as SVP of U.S. revenue and market development at Yahoo at a very dicey time.

Besides facing a withering U.S. economy, a weakened stock price after the takeover attempt by Microsoft and ensuing mess related to it, it was revealed that the Justice Department might block the deal Yahoo recently struck to outsource some of its ad sales to Google (GOOG).

Yahoo said that in this newly created role Bradford will oversee sales, market development for advertisers, small business and HotJobs. She will report to Hilary Schneider, EVP of Yahoo’s U.S unit.

Karnstedt, whom I interviewed when he first took over ad sales a little more than a year ago, is leaving to pursue other opportunities.

In Silicon Valley, that means the inevitable stop at a VC firm. Hence, Redpoint!

Interestingly, he joins former Ask.com head Jim Lanzone at Redpoint, while former Yahoo execs Jeff Weiner (Accel Partners and Benchmark Capital) and David Goldberg (Benchmark) also landed cushy EIR gigs after leaving Yahoo.

Karnstedt had been SVP of U.S. sales at Yahoo and had apparently resigned from the company earlier this summer (thanks for not confirming that when I asked so many times, Yahoo!)

With Yahoo seven years, he was charged with the difficult task of integrating Yahoo’s search, display, Blue Lithium and Right Media sales teams.

And while Karnstedt was well liked, many complained that the longtime online ad techie was not enough of a gregarious and schmoozy ad sales exec, with deep relationships on Madison Avenue, as Millard–and Bradford–surely are.

As I wrote in Aug. 2007, after an interview with him at Yahoo’s New York offices:

I made the point to Dave (he is the kind of guy you can call Dave, as you can see pictured here) that an ad guy needs to sell himself, but to no avail, so we press on in text. Nonetheless, let me set the visual scene:

Nicest guy you ever want to meet walks into nondescript room, wearing khaki-oxford-jacket Internet uniform 101. Declares Yahoo is going to kick some advertising butt in the nicest possible way. It is revealed this nice guy has been around the Web block for quite a while. Much chitter-chatter ensues. Cut to my clear-as-Fiji-water observation that nice guy, as nice as he is, has his work cut out for him.”

And now, more than ever in Yahoo’s key ad market, so does Bradford.

On one of my many trips to Los Angeles (what can I say? I like to hang where LoRo* hangs), I dropped in to see Nick Grouf of Spot Runner.

As many might know, Spot Runner is an online-offline ad agency play that has gotten big funding and even bigger hype of late.

We’ll see how that goes. But Spot Runner actually seems to be tackling an underserved (and unexciting) market of local and national clients in need of cheap online ad solutions married to more traditional marketing venues to boost revenue.

Here’s my video interview with Grouf at Spot Runner’s offices on Wilshire Boulevard:

I met Grouf many years ago when he–along with Spot Runner partner David Waxman–founded PeoplePC and Firefly Networks.

Grouf sold the struggling PeoplePC–which hawked computers bundled with an online service–to Earthlink (ELNK) in 2002 for $10 million and assumption of $35 million in liabilities, in a Web 1.0 meltdown deal that followed a disastrous IPO.

He then started working for the Presidential campaign of Sen. John Kerry, helping figure out how to best and most cheaply place critical television ads–crunching all sorts of data about lots and lots of neighborhoods and towns and cities nationwide to figure it out.

What Grouf figured out, though, was that a system for doing so was nonexistent.

That experience turned into Spot Runner, which is essentially a do-it-yourself model that tries to iron out inefficiencies in the buying and selling of advertising and bridge the gap between the traditional and online ad markets.

Offering cheap ad templates, clients can make and place low-cost television and radio ads for small and national businesses, as well as political campaigns, and get analytics about the impact of the ads. Some ads cost as low as $500.

Spot Runner got a pile of cash to try to do that better, recently nabbing $51 million in funding to add to the $60 million already raised.

Investors include international media giants Daily Mail and General Trust (DMGT.L) and Grupo Televisa (TV), investment company Legg Mason Capital Management (LM) and luxury conglomerate Groupe Arnault/LVMH (MC.PA).

Spot Runner’s previous investors are Allen & Company, Battery Ventures, Comerica Bank (CMA), Lachlan Murdoch, Vivi Nevo, Capital Research and Management, CBS (CBS), Index Ventures, Interpublic Group (IPG), Tudor Investment Corporation and WPP.

Its board includes Index’s Danny Rimer and former AOL exec Bob Pittman.

All that money has given Spot Runner an eye-popping valuation upwards of $500 million.

This is its biggest burden, I think, setting expectations very high for what is still a little start-up.

And while there are rumors of both Microsoft and Google, as well as Comcast, being interested in acquiring the company, Grouf dismisses the speculation.

He says Spot Runner is more intent on using the money raised to buy companies and improve its offerings.

For example, it recently bought Weblistic, a local search listings creator, and hired former Microsoft exec Joanne Bradford.

Bradford, who was a VP and chief media officer of MSN Media Network, is executive vice president of National Marketing Services at Spot Runner, focusing on getting national advertisers to also think small and targeted.

Who knows whether the company will be able to overcome its hype, but time (and money) will tell.

(*And a free D6 bag for anyone who correctly identifies who I am referring to here, either by sending in a comment or an email to me at kara@allthingsd.com.)

In a much-expected financing, LinkedIn has joined the big funding club (Slide, Spot Runner) of late, by raising $53 million at a startling $1 billion valuation.

Why go public when you can just pretend?

Actually, unlike a lot of Web 2.0 start-ups, the professional networking site, which had 23 million active monthly members in June, has been profitable since 2006.

According to execs, it has revenues of about $100 million a year, from premium subscriptions and job listings, as well was advertising and corporate sales.

The new slug of cash comes from new investor Bain Capital Ventures, along with existing investors Sequoia Capital, Greylock Partners, and Bessemer Ventures.

LinkedIn had previously raised $27 million for a total of $80 million. Yipes!

“This additional funding will give us even more flexibility to execute on our vision for millions of professionals to increase their effectiveness by using LinkedIn to build relationships and exchange knowledge, opportunities and advice,” wrote LinkedIn CEO Dan Nye (pictured here) in a blog post tonight.

In an interview with LinkedIn’s founding CEO and Chairman Reid Hoffman (pictured here) today, he told BoomTown that the money raised would be used for corporate development and acquisitions.

“We’ll be doing small technology acquisitions to improve our service,” said Hoffman. He also noted that it was unlikely the company would be doing an IPO in the immediate future, which has been bandied about.

“We have no immediate plans” for a public offering, said Hoffman. “We still have a lot of ground to cover to grow.”

Comparing the the business-oriented LinkedIn professional network with hot social networks like Facebook, Hoffman noted: “They have page views and time on the site and are looking for a scalable economic model and we have an economic model and will focus on growing usage.”

LinkedIn certainly has been growing its coffers. It raised $5.2 million in its first round, $10 million in its second and $12.8 million in its third.

Here is a video of LinkedIn’s investors trying mightily to play down the $1 billion valuation, while also pumping it up.

You gotta love the cheerleading of Greylock’s David Sze, Bessemer’s David Cowan and Mark Kvamme of Sequoia, along with new investor Jeffrey Glass of Bain (who will join LinkedIn’s board as an observer):

So what will Microsoft’s (MSFT) next quarry be?

Facebook? AOL? A series of small Web 2.0 stars like Digg (probably too late, as Google is already first in line there again), Spot Runner and others?

That is, if there will be one after the Yahoo (YHOO) takeover debacle.

Or, if the software giant somehow screws up the courage and, despite the constant rejection, goes back again to try to scoop up Yahoo.

In a post Friday, BoomTown made the case that Microsoft was not going to do that, burned too many times and ready to move on for various reasons (regulatory problems, poisoned relations and sheer pique).

That is not to say that I think Microsoft should walk away. It should not, as I argued two weeks ago in a post titled “A Deal Must Be Done.”

As I wrote: “Because, if [Microsoft CEO Steve] Ballmer is serious about his contention, which he made fervently onstage at D6, that the software giant keeps ‘coming and coming and coming,’ it simply cannot make that attack from a piddling 9% market share in the online search business.”

No, indeed, and that’s why it should watch carefully as the price of Yahoo’s stock drops and what happens between Yahoo and billionaire activist investor Carl Icahn.

Icahn is waging a proxy war against Yahoo, which should come to a head at the company’s board meeting on Aug. 1.

So if Ballmer is serious about competing strongly in the search-ad market, he must keep Yahoo in mind, no matter the checkered history of their dealings so far.

And even, as several sources tell me, swallow the bile it must have had after Microsoft thought it won the search deal with Yahoo, at least until a June 8th meeting in which Yahoo offered the whole company or nothing.

Yahoo then turned around and signed with Microsoft archrival Google (GOOG) last week.

“They were uncorking the champagne last week on the Yahoo search deal and then it all went sideways to Google,” said one source. “Someone’s head will roll.”

The big head here, of course, is Platforms and Services Division President Kevin Johnson (pictured here), one of the big proponents of the various deals with Yahoo.

Now, he and others at Microsoft have to be scrambling for alternative schemes to figure out a way to stay in the game.

While some think Microsoft should stick more to its knitting and buy enterprise companies like SAP, Ballmer and Johnson have been adamant that online ads will be its next great business.

And, given the growth there, being No. 2 in the space is not the worst place to be.

In any case, many expect a bold step from Microsoft in the space now.

The obvious move is a splashy bid for Facebook. As before, Microsoft continues to send subtle signals of interest, now via third parties, to the social-networking site.

Not so fast, though.

As much as many at Facebook would like the sell out for a price tag in the $10 billion to $15 billion range, CEO and Founder Mark Zuckerberg remains uninterested and seems willing to continue resisting the pressure (see BoomTown’s take on that here).

As for AOL–it’s a more likely scenario, given it would allow Microsoft to double down in the display space with the Time Warner (TWX) division’s Platform A ad unit and also gain some other strong properties (such as in video search with Truveo, with widgetmaker Userplane, as well as in instant messaging).

It would also probably like to give the boot to Google, which now serves up AOL search ads (and which also holds a 5% stake in AOL).

Microsoft has been very close to buying AOL before, once even considering spinning its Internet properties and AOL into a newco, so it does know the lay of the land there.

And Time Warner CEO Jeff Bewkes is casting about for solutions to unlocking the value of the interactive unit, which has always needed to run free from the mother ship.

In fact, here’s some video highlights of my interview with Bewkes at our recent D: All Things Digital conference, in fact, where he discusses AOL’s challenges:

Imagine this:

Google (GOOG) starts buying up a series of promising and innovative Web 2.0 companies that Microsoft (MSFT) is either partnered with or clearly is or should be interested in.

It starts with Digg, moves onto, say, Spot Runner and others (Meebo, FriendFeed, iLike and even Slide?), focused especially in the online ad, messaging, online apps and mobile spaces.

And, just to stir up the pot, why not take a gander at some bigger Internet fish? Facebook, for example. Or even eBay (EBAY), which is looking more and more like acquisition bait to me.

It could happen. Some of it will. And sooner rather than later, I would guess.

As Microsoft contemplates its next move in the Internet space after its failed bid for Yahoo (YHOO)–in order to realize its stated goals of being a big player in the ad and search space–it feels to me like it is moving with a Yahoo-level of lugubriousness.

Making some unimpressive announcements (Cash back for search? Now there’s a non-game changer), playing coy with regard to Carl Icahn’s proxy fight against Yahoo and noodling around with plots to buy part of Yahoo, Microsoft has essentially gone radio silent.

And while many smart minds think Yahoo is Microsoft’s only true path to serious competition with Google and should just cut to the chase and make another bid, it seems to be just lazily circling.

Maybe it is actually feverishly working on some amazing and bold renewal of its Yahoo deal behind the scenes, which would be great.

It better be doing something, since it seems as if Google has no intention of backing off in its bid to dominate further what it already dominates.

Clearly, the search giant had no problem getting Microsoft’s face in its takeover battle with Yahoo.

In fact, looking forward at the larger Internet battlefield–which will obviously be almost entirely fought between Microsoft and Google for the next few years, at least (although an unknown force will also surely emerge)–how Google has behaved with regards to Yahoo is instructive.

As Microsoft, forced to make a hostile bid this February after being rejected time and again by Yahoo in 2007, faced even more rejection from the Internet portal, it did not take long for Google to enter the fray.

Its tactics were to be a helping hand, a strong alternative and a flexible partner who could get Yahoo out of its jam by offering a deal that would, of course, help Google too by allowing it the chance to grab another tasty slice of the online search-ad pie.

And to throw salt in Microsoft’s wounds, its top execs then publicly pooh-poohed the deal as anti-competitive, specifically with regard to communications and display advertising.

This, still pending, even as Google’s own possible search-ad outsourcing deal has been quite questionable from a monopolistic point of view.

Now, since Microsoft does not feel compelled to make any kind of significant move, all eyes should be on what Google does next.

So, even if it is a small move like buying a Digg–as BoomTown has written again and again, the pair have been seriously talking with each other for months now, so watch that space–or some other prominent Web 2.0 start-up like it, such a thing would be a clear indicator of Google’s intentions going forward.

In part, that is to keep Microsoft from getting any kind of true traction in Silicon Valley, as it would have if it had managed to purchase Yahoo.

Welcome to Microsoft CEO Steve Ballmer’s nightmare.

So–as Freddy says–whatever you do, don’t fall asleep!

Please see this disclosure related to me and Google.

GodTube, which describes itself as a Christian video-driven social-networking site, “where users find inspiration, interact, chat, share and upload” Christian video, has about 2 million users per month.

GodTube also lets churches stream sermons and other events live on its “Godcaster” subscription service.

Also, its motto is “Broadcast Him,” but GodTube also calls itself “Jesus 2.0.” Get it?

Perhaps more in the holy-grail territory, GodTube just nabbed $30 million this week in funding from GLG Partners (GLG), which is also an investor in the less-holy Glam Media site, according to paidContent.

That gives the Dallas-based GodTube a $150 million valuation, putting it right up there with other miraculous start-up valuations like yesterday’s $500 million valuation for the online ad agency Spot Runner.

Praise the VC (and, for GodTube fans, JC too)!

Here’s the North Point Church video on GodTube:

Project Granola?

Apparently, that’s the jokey nickname that’s been given by some in the company to Microsoft’s (MSFT) new online strategy, in the wake of its failed efforts to acquire Yahoo (YHOO) that ended in a big heap of mess this past weekend.

Now, sources tell BoomTown, it is all about “organic”–hence the image of a healthy handful of granola (except for the fact that, in my experience, nobody really likes granola after eating it as much as they think will before).

In any case, it is a word Microsoft folks have been slipping into the conversations with BoomTown over the past few days, so much so that I have started to feel like I was talking to execs from Whole Foods.

Now Microsoft’s greenness has gone public.

Case in point: Brian Hall, Windows Live General Manager, who trotted out the organic word in front of Merrill Lynch analysts yesterday, as reported by CNET’s Ina Fried, saying: “We’ve withdrawn the offer and moved on, and now are focused on how we grow as fast as possible organically.”

But what does organic mean exactly?

Two things, it seems.

First, stepping up spending on marketing, technology and research to try to find ways to differentiate from Google (GOOG) and get into the No. 2 spot now held by Yahoo.

Of course, that plan has not worked out so well as yet for the software giant, with Microsoft spending billions of dollars with no profits and little gain in online search or ad market share, while its archrival Google keeps growing stronger.

Even so, while in Korea today, Microsoft Chairman Bill Gates backed Microsoft CEO Steve Ballmer’s do-it-yourself path and his move to walk away from Yahoo.

“The key decisions on that will be made by Microsoft CEO Steve Ballmer, who took a look at Yahoo and decided that, on our own, he likes the stuff that we’re doing,” said Gates.

Gates also added what amounts to the second option for Microsoft. “I wouldn’t rule out some partnerships, but we don’t have anything imminent there,” he said.

While a return to Yahoo is a possibility, in fact, buying up Web 2.0 stars is likely to be a bigger focus of the company.

“Yahoo can twist,” said one source. “Microsoft has lots and lots of other options.”

According to sources close to the company, for example, Microsoft’s bankers had been putting out subtle signals to Facebook to see if it would be open to a full buyout.

Microsoft already invested $240 million in the hot social-networking site, an investment that gave Facebook its kooky $15 billion valuation.

And its execs have long told Facebook execs they wouldn’t mind a bigger bite–um, like all of it.

“We just wanted to gauge their interest, more than any real effort,” said another source, who expects Facebook to stick to its longish path to an eventual IPO.

But, as is no secret, Microsoft has selections all over Silicon Valley to help it improve its Internet chances.

Those would include buying bigger vertical sites in strong categories like autos or jobs or finance, and also scooping up smaller but fast-growing socially oriented sites like Digg, Meebo, Yelp or focusing on ad plays like Spot Runner (which just got another big dollop of funding).

There might even be some sense in spinning some of these and all Microsoft Web units off into a separate Internet company, which would be another way of integrating even bigger deals for properties like Time Warner’s (TWX) AOL or News Corp.’s (NWS) MySpace (which are longer shots, I think).

In a post I did in February right after Yahoo rebuffed Microsoft for the first time, I suggested such a course for the company.

As I wrote:

Here’s a list: LinkedIn. Digg. Flixster. Slide or RockYou. Veoh. WordPress. Sphere. Sugar. Some international stuff. And more.

Then, some noted, Microsoft would have to give massive financial incentives to those entrepreneurs to stay and thrive. Most importantly, it would have to keep its Redmond hands from interfering.

Now that would send shivers up the spine of Larry and Sergey.”

And that, most of all, would be more like icing on the cake for Microsoft and be much more tasty than a bowl full of granola.

And, as Martha Stewart says: It’s a good thing.

Spot Runner, the online ad agency, delivered yet another Web 2.0 miracle today, raising another $51 million in funding from a diverse group of investors.

Among other services, Spot Runner makes and places low-cost television and radio ads for small businesses and is trying to bridge the gap between the traditional and online ad market.

In this round, those stepping up to invest in the Los Angeles-based start-up include international media giants Daily Mail and General Trust (DMGT.L) and Grupo Televisa (TV), investment company Legg Mason Capital Management (LM) and, curiously, luxury conglomerate Groupe Arnault/LVMH (MC.PA).

This group, along with existing investors, forked over the $51 million to add to the $60 million already raised. This appears to give it a massive valuation of upward of $500 million.

Well, at least in the land of Web 2.0 it does. In the real world, it still remains to be seen. But that has not stopped the nonstop investment party of late for Web 2.0 start-ups.

Web-based instant messaging company Meebo recently raised another $25 million at a reported $250 million valuation, while widgeteer Slide got $50 million for a $550 million valuation.

Of course, the champ of them all has been the social-networking site Facebook, which now has a $15 billion valuation.

Wheeeeeeeeeeeeeee! Or maybe not so much, but obviously no one in Silicon Valley is listening to BoomTown at this Kool-Aid carnival.

Spot Runner’s previous investors are: Allen & Company, Battery Ventures, Comerica Bank (CMA), Lachlan Murdoch, Vivi Nevo, Capital Research and Management, CBS (CBS), Index Ventures, Interpublic Group, Tudor Investment Corporation and WPP.

So far, this group has invested $60 million in Spot Runner. Its board includes Index’s Danny Rimer and former AOL exec Bob Pittman.

“We want to use the investment to make a real penetration in the market,” said Nick Grouf, chairman and CEO of Spot Runner. “We want to expand both organically and through acquisitions, as well as expand our staff, and these strategic investors will help us do that.”

Spot Runner has already been doing that. For example, it recently bought Weblistic, a local search listings creator, and hired former Microsoft exec Joanne Bradford.

The Daily Mail is a large media company based in the United Kingdom, with newspapers, online and radio assets, while Grupo Televisa is one of the largest media conglomerates in the Spanish-speaking world.

Groupe Arnault/LVMH owns some of the world’s toniest brands, including Moët & Chandon, Hennessy, Louis Vuitton and Givenchy.

Grouf, again along with partner David Waxman, also previously founded PeoplePC and Firefly Networks.

In the spirit of the funding, here’s one of my favorite Kool-Aid commercials:

An interesting move with MSN exec Joanne Bradford heading over to the Internet-based ad agency Spot Runner, which helps companies create ads for radio and television.

She will be executive vice president of National Marketing Services, focused on national advertisers, for the ad-services company. Bradford was a VP and chief media officer of MSN Media Network and had worked at BusinessWeek before that.

One might expect a lot more movement over at Microsoft (MSFT) in its Internet arena, with its bid to acquire Yahoo (YHOO) pending and its execs in flux. Recently, for example, its SVP of the Online Service Group, Steve Berkowitz, whom Bradford reported to, was boxed out, as others have ascended (see my take here).

Things will be a lot simpler for Bradford at the Los Angeles-based Spot Runner, which recently bought Weblistic, a local search listings creator.

The much-hyped start-up has gotten $40 million in funding from investors including Battery Ventures, Index Ventures, WPP, IDG and CBS (CBS).

“I am going back to my entrepreneurial, build-something roots,” said Bradford. “There is such inefficiency in buying and selling of advertising and someone has to solve that, both for big companies and small ones.”