• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI

2

Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 

3

Meet the 20-year-old CEO who launched a company in high school to solve Gen Z's entry-level job crisis

1

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI

2

Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 

3

Meet the 20-year-old CEO who launched a company in high school to solve Gen Z's entry-level job crisis

Microsoft’s $2 billion online problem

By
Adam Lashinsky
Adam Lashinsky
Down Arrow Button Icon
By
Adam Lashinsky
Adam Lashinsky
Down Arrow Button Icon
July 30, 2009, 10:34 AM ET

Even with Yahoo deal Microsoft will continue to struggle — and lose money — online.

The anti-climactic deal of the year is now out.  Long after the sizzle faded from Microsoft’s (MSFT) failed $40-billion-plus bid for  Yahoo (YHOO), the two companies announced Wednesday they’ll do what sympathetic observers urged them to do two years ago. They’ll stop competing on search and search-advertising technology, enabling them to combine forces against Google. (GOOG)

Critics frowned on Yahoo (where’s the “boatloads” of upfront cash Yahoo CEO Carol Bartz promised she’d extract from Steve Ballmer?) and praised Microsoft, The Wall Street Journal going so far as suggesting the tide may turning in the tired monopolist’s favor. Perhaps. Beyond the something-must-be-said-because-they-called-a-press-conference chatter, however, a few points to consider:

  • Yahoo is a sideshow now. Sure, it’s an afterthought that’s still worth $21 billion, even after being hammered by investors Wednesday. But this is a battle of giants now, and only giants. Consider in comparison the market capitalizations of Microsoft ($212 billion), Apple (AAPL) ($143 billion), Google ($138 billion), Cisco (CSCO) ($125 billion), Oracle (ORCL) ($110 billion) and Hewlett-Packard (HP) ($101 billion). These are the titans that are clashing. Their strategic feints and jabs at each other are the ones that matter now.
  • This deal won’t become reality quickly. What happens next between Microsoft and Yahoo is, well, nothing. The two must convince Washington and Brussels that their combination isn’t anti-competitive. It’s sort of laughable. Of course they won’t be anti-competitive. They’ll be lucky to get Google even to notice them. But the way things work they won’t even get to start trying until next year. (A contrary thought: Several times during the course of writing this post I decided to use Bing, Microsoft’s renamed search engine. I actually liked its look, feel and, importantly, results. I doubt I’ll stop using Google any more than I’m likely to give up on Microsoft Outlook. The behavior is too ingrained. But still, it makes you wonder and ought to worry Google just a little.)
  • Microsoft will have to make many more clever deals. One of Google’s strongest suits in search is the toolbar arrangements it has negotiated along the way that place the Google search box at the top of the page of many user’s screens. These cost money in the form of revenue sharing agreements, and Microsoft is in this game too. Staying in it is expensive and sometimes futile. Microsoft made a big deal, for example, of a November, 2008, agreement with Sun Microsystems to include what was then Live Search, now Bing, with a key version of Sun’s important Java software. One can envision Sun’s new owner, Oracle, beating a hasty retreat from that deal, given Oracle’s lack of affection for Microsoft.
  • Microsoft loses gobs of money online — and seems resigned to losing more. Overlooked in the hoopla over Microsoft’s first-ever year-over-year revenue decline that it reported last week is that its online division continues to bleed red ink. I focused on this last year in a piece that asked Why Can’t Microsoft Make Money Online? The short version: Catching Google is costly in terms of personnel, marketing and capital expenditures; Microsoft’s people have software on the brain, not the Internet; and online advertising is a scale business. With the Yahoo deal Microsoft is addressing the last issue. As for the first two, Microsoft CEO acknowledged Wednesday that the benefit of the deal to  Yahoo is that it won’t have to keep spending heavily on search technology. Microsoft will. By the way, the two billion figure in the headline of this piece? That refers to the $2.3 billion Microsoft’s online business services division lost in its just-reported 2009 fiscal year on declining revenues of $3.1 billion. Think about that, Google remains a cash machine, Yahoo itself is profitable and getting more so, but Microsoft’s online business, the one that will spend heavily and give Yahoo most of the revenue from combined search-ad sales, is oozing more than half a billion dollars each quarter.

Microsoft has said repeatedly that online mastery is critical to its future. Maybe it is. For now, it’s a cash sinkhole that is years from providing a return on Microsoft’s investment.

About the Author
By Adam Lashinsky
See full bioRight Arrow Button Icon

Latest in

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in

U.S. allows Russia oil sales waiver to expire despite tight market
EnergyOil
U.S. allows Russia oil sales waiver to expire despite tight market
By Jennifer A. Dlouhy and BloombergMay 16, 2026
7 hours ago
AI poised to tilt job market leverage toward older workers
AIHiring
AI poised to tilt job market leverage toward older workers
By Victor Swezey and BloombergMay 16, 2026
7 hours ago
U.S., Iran stall on Hormuz reopening as oil supplies tighten
PoliticsIran
U.S., Iran stall on Hormuz reopening as oil supplies tighten
By Skylar Woodhouse, Jeff Mason, Arsalan Shahla and BloombergMay 16, 2026
7 hours ago
Former top Russian official admits the country is over Putin and can ‘imagine a future without him’ — even elites bail as Kremlin seizes their assets 
PoliticsRussia
Former top Russian official admits the country is over Putin and can ‘imagine a future without him’ — even elites bail as Kremlin seizes their assets 
By Jason MaMay 16, 2026
8 hours ago
Trump’s IRS suit may end with a $1.7 billion compensation fund
PoliticsDonald Trump
Trump’s IRS suit may end with a $1.7 billion compensation fund
By Zoe Tillman, Chris Strohm, Hadriana Lowenkron and BloombergMay 16, 2026
10 hours ago
World’s largest aircraft carrier returns from 11-month deployment, longest since Vietnam, after supporting Iran war and Maduro raid
PoliticsMilitary
World’s largest aircraft carrier returns from 11-month deployment, longest since Vietnam, after supporting Iran war and Maduro raid
By The Associated PressMay 16, 2026
10 hours ago

Most Popular

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloMay 16, 2026
18 hours ago
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
Politics
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
By Jason MaMay 16, 2026
8 hours ago
Meet the 20-year-old CEO who launched a company in high school to solve Gen Z's entry-level job crisis
Future of Work
Meet the 20-year-old CEO who launched a company in high school to solve Gen Z's entry-level job crisis
By Jake AngeloMay 16, 2026
22 hours ago
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
4 days ago
Despite having a $165 million net worth, Scarlett Johansson says work-life balance doesn’t exist—and the first step to success is admitting that
Success
Despite having a $165 million net worth, Scarlett Johansson says work-life balance doesn’t exist—and the first step to success is admitting that
By Preston ForeMay 13, 2026
4 days ago
‘You’re not a hero, you’re a liability’: Shark Tank’s Kevin O’Leary warns Gen Z founders to stop glorifying hustle culture
Future of Work
‘You’re not a hero, you’re a liability’: Shark Tank’s Kevin O’Leary warns Gen Z founders to stop glorifying hustle culture
By Jacqueline MunisMay 16, 2026
18 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.