Block vs Toast: Founders, CEOs and History
Block was founded in 2009 by Jack Dorsey, Jim McKelvey and is led by Jack Dorsey. Toast was founded in 2011 by Aman Narang, Steve Fredette, Jonathan Grimm and is led by Aman Narang.
Company facts
Founders
Block
Jack Dorsey
Dorsey co-founded Square in 2009 with Jim McKelvey after McKelvey lost a glass sale he could not take by card, and has run the company ever since: through the 2015 IPO, the rise of Cash App, the December 2021 rename to Block, the Afterpay purchase and, in Febr…
Jim McKelvey
McKelvey's lost $2,000 glass sale is Square's origin story. He worked with Dorsey and engineer Tristan O'Tierney on the first reader and the flat-pricing business model, and later wrote 'The Innovation Stack' (2020), which explains how Square survived copycats…
Toast
Aman Narang
Aman Narang co-founded Toast in 2011 and held president and COO roles before becoming CEO on January 1, 2024, succeeding Chris Comparato. He is also a director of the company.
Steve Fredette
Steve Fredette co-founded Toast in 2011 and served as president, helping build the company's product and go-to-market organization through its growth and 2021 IPO.
Jonathan Grimm
Jonathan Grimm co-founded Toast in 2011 and served as its chief technology officer during the company's early years, leading development of the cloud platform.
CEOs and their tenures
Block
- Jack Dorsey2009–present
Co-Founder, Block Head and Chairman (Chief Executive)
Has led Square and Block since 2009: the 2015 IPO, the growth of Cash App, the 2021 rename to Block, the Afterpay purchase, bitcoin projects such as Bitkey and Proto, and the February 2026 cut to just under 6,000 employees.
Source - Alyssa Henry2014–2023
Seller Lead, then Chief Executive of the Square business
Joined from Amazon in 2014 as seller lead and became chief executive of the Square business when the parent was renamed Block in December 2021.
Source
Toast
- Chris Comparato2015–2023
Chief Executive Officer
Led Toast through its 2021 IPO; co-founder Aman Narang succeeded him on January 1, 2024.
Source - Aman Narang2024–present
Co-Founder and Chief Executive Officer
Directs overall corporate vision, product architecture, restaurant partnerships, and public company leadership.
Source
Timeline: Block and Toast side by side
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.
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.
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.
2011Toast
Toast Founded in Cambridge by MIT Endeca Alumni
Aman Narang, Steve Fredette, and Jonathan Grimm founded Toast to build cloud software for restaurants.
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.
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.
2013Toast
Pivots from Mobile Consumer App to Full Restaurant POS
Pivoted to a complete cloud restaurant POS system, signing its first commercial restaurant in Cambridge.
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.
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.
2015Toast
$30M Series B Led by Bessemer Venture Partners
Raised $30 million, crossing 1,000 restaurant locations and expanding regional field sales across the US.
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.
2018Toast
$115M Series D at $1.4B Valuation & Launches Toast Go
Raised a $115 million Series D led by TCV and Tiger Global, reaching unicorn status, and launched the Toast Go handheld.
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.
2020Toast
$400M Series F at $4.9B Valuation & COVID-19 Operational Pivot
Raised a $400 million Series F at a $4.9 billion valuation in February 2020, then cut about half its workforce in April 2020 as COVID-19 shut dining rooms.
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.
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.
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.
2021Toast
Historic Initial Public Offering on the NYSE (NYSE: TOST)
Went public on the New York Stock Exchange, raising $870 million at an opening valuation of $20 billion.
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.
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.
2023Toast
Expands to Canada, UK and Ireland; Crosses 100,000 Locations
Began selling outside the US and passed 100,000 restaurant locations.
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.
2024Toast
Aman Narang Appointed CEO & Toast Achieves GAAP Profitability
Co-founder Aman Narang became CEO on January 1, 2024; Toast reported $19 million of GAAP net income for the year, its first annual profit.
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.
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.
2025Toast
Revenue Reaches $6.15B and Net Income $342M
Added a record 30,000 net locations to about 164,000 and processed about $195 billion in GPV.
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%.
2026Toast
About 180,000 Locations and $2.4B ARR by Mid-Year
Q2 2026 revenue rose 23% to $1.91 billion with a record 9,500 net location adds.
Acquisitions
Block
- Afterpay2022$29B
- TIDAL (majority stake)2021$297M
- Credit Karma Tax (now Cash App Taxes)2020$50M
- Verse2020Undisclosed
- Weebly2018$365M
- Caviar2014$90M
Toast
- Delphi Display Systems2023Undisclosed
- xtraCHEF2021Undisclosed
- Sling2021Undisclosed
Questions about Block vs Toast
Who is the CEO of Block Inc and Toast, Inc.?
Block Inc is led by Jack Dorsey and Toast, Inc. is led by Aman Narang. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was Block Inc founded vs Toast, Inc.?
Block Inc was founded in 2009 — 2 years before Toast, Inc., which was founded in 2011. Block Inc's longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger Toast, Inc..
How many employees does Block Inc have compared to Toast, Inc.?
Block Inc employs approximately 10,205 people, while Toast, Inc. employs approximately 6,500. Block Inc has the larger workforce at 10,205 employees, compared to Toast, Inc.'s 6,500. A higher headcount does not necessarily imply greater efficiency — it often reflects differences in business model (e.g., manufacturing vs. software).
Where are Block Inc and Toast, Inc. headquartered?
Both Block Inc and Toast, Inc. are headquartered in United States, meaning they operate under the same primary regulatory and tax environment.
Who founded Block Inc and Toast, Inc.?
Block Inc was founded by Jack Dorsey, Jim McKelvey. Toast, Inc. was founded by Aman Narang, Steve Fredette, Jonathan Grimm.
Which company has a longer operating history — Block Inc or Toast, Inc.?
Block Inc has been operating for approximately 17 years, making it the more established of the two companies. Toast, Inc. has been in operation for around 15 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 Block vs Toast overview