Microsoft vs PayPal: Founders, CEOs and History
Microsoft was founded in 1975 by Bill Gates, Paul Allen and is led by Satya Nadella. PayPal was founded in 1998 by Max Levchin, Peter Thiel, Luke Nosek and is led by Enrique Lores.
Company facts
Founders
Microsoft
Bill Gates
Microsoft was founded in 1975 in Albuquerque, New Mexico, by Bill Gates and Paul Allen, childhood friends from Seattle who had spent their teenage years finding ways to get free time on mainframe computers.
Paul Allen
Paul Allen co-founded Microsoft and was crucial to its earliest technical and strategic decisions. He helped develop Altair BASIC, gave the company its original name, and participated in the operating-system opportunity that led to MS-DOS.
PayPal
Max Levchin
PayPal possesses arguably the most well-known, mythological, and influential founding story in the entire history of Silicon Valley, famously creating the 'PayPal Mafia', a concentrated group of effective, idiosyncratic founders who went on to literally build…
Peter Thiel
Peter Thiel served as an early strategic leader and CEO during the period when PayPal chose payments over broader online banking.
Luke Nosek
Luke Nosek co-founded Confinity with Max Levchin and Peter Thiel in 1998 and led marketing and strategy in PayPal's early years.
Elon Musk
Elon Musk founded X.com in 1999 as an online bank after selling Zip2. X.com merged with Confinity in March 2000, and Musk served as CEO of the combined company until the board replaced him with Peter Thiel later that year.
CEOs and their tenures
Microsoft
- Bill Gates1975–2000
Co-founder and CEO
Gates built Microsoft's licensing model: software sold to many hardware makers rather than tied to one.
Source - Steve Ballmer2000–2014
CEO
Ballmer grew revenue from about $23 billion in FY2000 to about $78 billion in FY2013 and built the enterprise server and sales business that Azure later scaled on.
Source - Satya Nadella2014–present
Chairman and CEO
Nadella made Azure and Microsoft 365 the company's core, opened Microsoft to Linux and open source, and positioned it early in generative AI through OpenAI.
Source
PayPal
- Alex Chriss2023–2026
President and Chief Executive Officer
Joined from Intuit in September 2023 after Dan Schulman. Margins and buybacks improved during his tenure, but branded checkout growth stayed slow, and the board replaced him with Enrique Lores effective March 1, 2026.
Source - Enrique Lores2026–present
President and Chief Executive Officer
Former HP Inc. CEO (2019-2026) and PayPal board chair; replaced Alex Chriss as CEO effective March 1, 2026. In his first full quarter (Q2 2026) PayPal beat estimates and raised full-year EPS guidance.
Source
Timeline: Microsoft and PayPal side by side
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.
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.
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.
1986Microsoft
Microsoft IPO
Microsoft went public on the Nasdaq in March 1986.
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.
1995Microsoft
Windows 95 Released
Microsoft released Windows 95 in August 1995.
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.
1998PayPal
Confinity Founded
PayPal traces its origins to Confinity and the early X.com online payments era.
2002PayPal
IPO and eBay Acquisition
PayPal went public and was acquired by eBay in 2002.
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.
2013PayPal
Braintree Acquired
PayPal bought the payments company Braintree, which owned Venmo, in 2013 for about $800 million.
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.
2015PayPal
PayPal Spins Off From eBay
PayPal became an independent public company again in 2015.
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.
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.
2018PayPal
iZettle Acquired
PayPal acquired the Swedish point-of-sale company iZettle in 2018 for about $2.2 billion.
2020PayPal
Acquired Honey
PayPal Holdings acquired Honey for $4 billion.
2023Microsoft
AI Leadership
Microsoft's expanded OpenAI partnership and Copilot product rollout placed the company at the center of enterprise generative AI adoption.
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.
2023PayPal
Alex Chriss becomes CEO
Alex Chriss became CEO of PayPal Holdings in 2023. Joined from Intuit in September 2023 after Dan Schulman.
2025PayPal
$33.172B FY2025 Revenue
PayPal reported $33.172 billion of revenue and $5.233 billion of net income.
2026PayPal
Enrique Lores Named CEO
PayPal appointed Enrique Lores President and CEO effective March 1, 2026.
2026PayPal
Strategic Reorganization Announced
PayPal reorganized around checkout, consumer financial services, Venmo, payment services, and crypto.
2026PayPal
Q2 2026 Beat and Raised Guidance
Q2 2026 revenue rose 5% to $8.68 billion and TPV rose 10% to $486.4 billion; full-year non-GAAP EPS guidance was raised to about $5.38.
2026PayPal
Stripe and Advent Takeover Approach Ends
PayPal's board reportedly rejected a $60.50-per-share approach valuing it above $53 billion; the Stripe and Advent consortium dropped its pursuit on August 28, 2026.
Acquisitions
Microsoft
- Activision Blizzard2023$68.7B
- Nuance Communications2022$19.7B
- ZeniMax Media2021$7.5B
- GitHub2018$7.5B
- LinkedIn2016$26.2B
PayPal
- Paidy2021$2.7B
- Honey2020$4B
- IZettle2018$2.2B
- Simility2018$120M
- Xoom2015$890M
- Braintree2013$800M
Questions about Microsoft vs PayPal
Who is the CEO of Microsoft Corporation and PayPal Holdings, Inc.?
Microsoft Corporation is led by Satya Nadella and PayPal Holdings, Inc. is led by Enrique Lores. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was Microsoft Corporation founded vs PayPal Holdings, Inc.?
Microsoft Corporation was founded in 1975 — 23 years before PayPal Holdings, Inc., which was founded in 1998. Microsoft Corporation's longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger PayPal Holdings, Inc..
How many employees does Microsoft Corporation have compared to PayPal Holdings, Inc.?
Microsoft Corporation employs approximately 223,000 people, while PayPal Holdings, Inc. employs approximately 23,800. Microsoft Corporation has the larger workforce at 223,000 employees, compared to PayPal Holdings, Inc.'s 23,800. A higher headcount does not necessarily imply greater efficiency — it often reflects differences in business model (e.g., manufacturing vs. software).
Where are Microsoft Corporation and PayPal Holdings, Inc. headquartered?
Both Microsoft Corporation and PayPal Holdings, Inc. are headquartered in United States, meaning they operate under the same primary regulatory and tax environment.
Who founded Microsoft Corporation and PayPal Holdings, Inc.?
Microsoft Corporation was founded by Bill Gates, Paul Allen. PayPal Holdings, Inc. was founded by Max Levchin, Peter Thiel, Luke Nosek, Elon Musk.
Which company has a longer operating history — Microsoft Corporation or PayPal Holdings, Inc.?
Microsoft Corporation has been operating for approximately 51 years, making it the more established of the two companies. PayPal Holdings, Inc. has been in operation for around 28 years. A longer operating history often signals greater institutional resilience and brand recognition, though it can also mean slower adaptation to new market conditions.
Figures come from each company's filings and the sources linked beside them. Amounts reported in another currency are shown in US dollars at an approximate rate and marked with ~. Back to the Microsoft vs PayPal overview