Block vs Microsoft: Founders, CEOs and History

Company facts

Founders

CEOs and their tenures

Timeline: Block and Microsoft side by side

1. 1975Microsoft

   Microsoft Founded

   Bill Gates and Paul Allen founded Microsoft after recognizing that the Altair 8800 needed usable programming software. Their first product, Altair BASIC, turned a hobbyist computer kit into a programmable platform.

2. 1981Microsoft

   MS-DOS Ships With IBM PC

   IBM introduced its personal computer with MS-DOS 1.0 and other Microsoft products. The milestone mattered because Microsoft's operating-system work moved from a small software supplier's project into the emerging corporate PC standard.

3. 1985Microsoft

   Windows Launch

   The release of Windows 1.0 began Microsoft's long move from command-line operating systems to graphical personal computing. The first version was not an instant blockbuster, but it gave Microsoft a user-interface path that could evolve with PC hardware.

4. 1986Microsoft

   Microsoft IPO

   Microsoft went public on the Nasdaq in March 1986.

5. 1990Microsoft

   Office Suite Release

   The bundling of Word, Excel, and PowerPoint into Microsoft Office created a productivity suite that became central to business work. The bundle simplified enterprise purchasing and made file compatibility a competitive weapon.

6. 1995Microsoft

   Windows 95 Released

   Microsoft released Windows 95 in August 1995.

7. 1998Microsoft

   U.S. Antitrust Case

   The U.S. Department of Justice accused Microsoft of using Windows power to suppress browser competition. The case mattered because it placed Microsoft's platform tactics under public and legal scrutiny at the height of its PC strong position.

8. 2009Block

   Square founded in St. Louis

   Jack Dorsey and Jim McKelvey start Square in February 2009 after McKelvey loses a $2,000 glass sale because he cannot take an American Express card. With engineer Tristan O'Tierney they build a reader that plugs into a phone's headphone jack.

9. 2010Block

   Square reader and app go public

   Square releases its free card reader and app, letting individuals and small sellers take card payments on a smartphone at one published rate instead of signing a bank merchant contract.

10. 2010Microsoft

    Azure Commercial Launch

    Azure gave Microsoft a way to compete in cloud infrastructure as enterprise customers began shifting workloads away from company-owned servers.

11. 2011Block

    Visa invests in Square

    Visa makes a strategic investment in Square in April 2011, a sign the card networks saw the startup as widening card acceptance rather than threatening it.

12. 2012Block

    Starbucks deal

    Starbucks invests $25 million and Square starts processing card payments at about 7,000 U.S. Starbucks stores, with Dorsey joining the Starbucks board.

13. 2013Block

    Square Cash launches

    Square launches Square Cash in October 2013, letting people send money to each other by email. It later becomes Cash App.

14. 2014Block

    Square Capital and Caviar

    Square starts lending to its own sellers through Square Capital in May 2014, with repayments taken as a share of daily card sales, and buys food delivery service Caviar.

15. 2014Microsoft

    Satya Nadella CEO

    Satya Nadella became CEO and moved Microsoft away from a strategy that forced every product to serve Windows. He prioritized Azure, Microsoft 365, open source, Linux support, cross-platform software, and a more collaborative developer posture.

16. 2015Block

    IPO on the New York Stock Exchange

    Square lists on the NYSE as SQ on November 19, 2015 at $9 a share, a valuation of about $2.9 billion, raising about $243 million.

17. 2016Microsoft

    LinkedIn Acquisition

    Microsoft agreed to acquire LinkedIn in 2016 for $26.2 billion in cash. The deal mattered because it added a professional identity network to a company already strong in Office, Dynamics, cloud services, recruiting tools, advertising, and enterprise sales.

18. 2018Block

    Cash App adds bitcoin; Square buys Weebly

    Cash App, which added the Cash Card debit card in 2017, lets users buy bitcoin from 2018, and Square buys website builder Weebly for $365 million. Commission-free stock investing follows in 2019.

19. 2018Microsoft

    GitHub Acquisition

    Microsoft acquired GitHub for $7.5 billion in stock, reversing years of developer skepticism toward the company. The acquisition placed Microsoft inside the daily workflow of software developers across languages, clouds, and operating systems.

20. 2020Block

    Bitcoin treasury, Verse and Credit Karma Tax

    The FDIC approves deposit insurance for Square Financial Services in March 2020. Square buys Spanish payments app Verse in June, puts $50 million into 4,709 bitcoin in October, and agrees in November to buy Credit Karma Tax for $50 million.

21. 2021Block

    TIDAL purchase and Square's own bank opens

    Square Financial Services opens on March 1, 2021, and Square agrees the same month to buy a majority of the TIDAL music service for $297 million in cash and stock, with Jay-Z joining its board.

22. 2021Block

    Afterpay deal announced

    Square agrees in August 2021 to buy Afterpay, the Australian buy now, pay later company, in an all-stock deal valued at about $29 billion.

23. 2021Block

    Square becomes Block

    On December 10, 2021, Square, Inc. renames itself Block, Inc., shortly after Dorsey steps down as Twitter's chief executive. Square remains the name of the seller business.

24. 2022Block

    Afterpay acquisition closes

    Block completes the Afterpay purchase on January 31, 2022. Because it paid in its own shares, which had roughly halved since the announcement, the deal was worth much less at closing than the headline $29 billion.

25. 2023Block

    Hindenburg report, Square leadership change and Bitkey

    Short seller Hindenburg Research accuses Cash App in March 2023 of inflated user metrics and weak compliance, which Block rejects.

26. 2023Microsoft

    AI Leadership

    Microsoft's expanded OpenAI partnership and Copilot product rollout placed the company at the center of enterprise generative AI adoption.

27. 2023Microsoft

    Activision Blizzard Acquisition Closes

    Microsoft completed the Activision Blizzard acquisition after intense regulatory review. The deal added Call of Duty, World of Warcraft, Diablo, Overwatch, Candy Crush, and other franchises to Microsoft Gaming.

28. 2024Block

    Proto mining chip and portfolio cuts

    Block says in April 2024 it has designed a 3-nanometer bitcoin mining chip, agrees in July to supply Core Scientific, and in November winds down its TBD crypto unit and scales back TIDAL.

29. 2025Block

    Cash App settlements and the XYZ ticker

    In January 2025 the CFPB orders Block to pay up to $120 million in Cash App redress plus a $55 million penalty, state regulators impose an $80 million anti-money-laundering penalty, and the ticker changes from SQ to XYZ.

30. 2025Block

    Block joins the S&P 500

    Block enters the S&P 500 on July 23, 2025, replacing Hess, and at its November investor day sets 2028 targets of about $15.8 billion of gross profit and $4.6 billion of adjusted operating income.

31. 2026Block

    Workforce cut to under 6,000

    On February 26, 2026, Dorsey announces Block will shrink from more than 10,000 employees to just under 6,000, citing AI, and the shares jump about 24%.

Acquisitions

Questions about Block vs Microsoft