The Square Mafia

July 21, 2023
Tech Mafias

Company "mafias" are all the rage, and we here at PIN love to dig deep into the most influential Tech Mafias, especially since we're huge on democratizing access to startup investing by supporting communities with all the legal and bureaucratic work when it comes to setting up a community investment club.

This week we take a look at one of the biggest Mafias up to date - the one and only Square Mafia. Square, as many will know already, was co-founded by Jack Dorsey, one of the co-founders of Twitter. The Square Mafia has raised billions of dollars, and formed over 35 successful companies.

If you missed our previous posts, make sure to check the Twitter Mafia, Lyft Mafia, Stripe Mafia, Netflix Mafia, InstaCart Mafia, Dropbox Mafia, Revolut Mafia, and Tesla Mafia articles. Investing in fellow coworkers' startups, especially as a community or alumni group, is one of the best ways to get in early on deals as well as support the ideas and ventures of people you love and admire. Who knows what's around the corner in your own network and community!

Companies Covered:

  • Apollo
  • OpenStore
  • Hummingbird
  • Found
  • Fi
  • Cocoon
  • Cockroach Labs
  • Opendoor
  • Primer
  • Anchorage Digital
  • Step
  • Ride Report
  • Capsule 8
  • Common Networks
  • Kikoff
  • Lime
  • Filmhub
  • Faire
  • Thistle Technologies
  • TruckSmarter
  • Safara
  • Complete
  • DoorDash
  • Outschool
  • Formation
  • Terraformation
  • Stelo Labs
  • Archie
  • TheCut
  • SecurityPal
  • Dada Group
  • Persona


Founder: Ray Li
Square Role: Software Engineer
Investors: Sequoia Capital
Capital Raised: $151.3M
Stage: Series C

Ray worked as a Software Engineer at Square before founding Apollo in 2015. Apollo is one of the most popular data platforms providing built-in integrations for sales teams.


Founders: Max Rhodes & Marcelo Cortes
Square Role: Director of Consumer Product & Staff Software Engineer
Investors: Y Combinator
Capital Raised: $1.7B
Stage: Series G

After working at Square, Max and Marcelo co-founded Faire, a marketplace and wholesale platform that helps retailers find and buy wholesale merchandise for their stores.


Founder: Keith Rabois
Square Role: COO
Investors: Founders Fund
Capital Raised: $137M
Stage: Series B

Keith was the COO at Square for almost three years. After that he was a Managing Director at Khosla Ventures for 6 years, before moving on to join Founders Fund as a General Partner. In addition to co-founding and serving as CEO of OpenStore, he is also currently a General Partner at FF.

Dada Group

Founder: Jun Yang
Square Role: Engineering
Investors: Sequoia Capital China
Capital Raised: $1.3B
Stage: Public

Jun is the co-founder and CTO at Dada Group, a leading platform of local on-demand retail and delivery in China.


Founder: Rick Song
Square Role: Engineer
Investors: Founders Fund
Capital Raised: $217M
Stage: Series C

Rick co-founded Persona in 2018, which is an identity platform that helps businesses verify customer identities that brings trust to online interactions.

Cockroach Labs

Founders: Peter Mattis, Spencer Kimball
Square Role: Software Engineers
Investors: Index Ventures
Capital Raised: $633.1M
Stage: Series F

Peter and Spencer worked as engineers at Square. Peter is now the co-founder and CTO while Spencer is the CEO at Cockroach Labs, a software company that develops a cloud-native SQL database for modern cloud applications.


Founder: Ian Wong
Square Role: Inference Scientist
Investors: GGV Capital
Capital Raised: $1.9B
Stage: Public

Ian worked as an Inference Scientist at Square before co-founding Opendoor in 2014. Opendoor is an operator of an online real estate marketplace used to streamline the sales process of home buying and selling.


Founders: Connor Dunn, Lauren Myrick
Square Role: Engineering Lead, General Manager Square Payroll
Founder Fund
Capital Raised: $75.2M
Stage: Series B

Both Lauren and Connor worked at Found for more than 5 years before starting Found in 2019. Found aims to make self-employment easier by providing business banking services to those running their own businesses.


Founder: Jonathan Bensamoun
Square Role: Product Manager
Investors: RRE Ventures
Capital Raised: $40M
Stage: Series B

Jonathan, a passionate tech entrepreneur who loves to solve hard problems with elegant solutions, is the founder/CEO of Fi. Fi is a provider of next generation of Smart Dog Collars.


Founder: Mahima Chawla
Square Role: Product Manager, Square Capital
Investors: Index Ventures
Capital Raised: $25.5M
Stage: Series A

Mahima worked as a Product Manager at Square for two years before co-founding Cocoon in early 2020. Cocoon’s platform provides employee leave benefits on anything from compliance to payroll.


Founder: Ryan Delk
Square Role: Local Marketing
Investors: Founders Fund
Capital Raised: $18.7M
Stage: Series A

In addition to co-founding Primer, Ryan is also an active investor and advisor. Primer was started in 2019, it is an online community where 7-14-year-olds spend their time coding video games.

Anchorage Digital

Founders: Diogo Monica, Nathan McCauley
Square Role: Platform Security Lead (DM), Security Engineering Manager / Security Engineer (NM)
Investors: Lux Capital
Capital Raised: $487M
Stage: Series D

Both Nathan and Diogo worked at Square for several years. In 2017 they came together to start Anchorage Digital, a digital asset platform offering custody, trading, and financing services, as well as staking and governance.


Founder: Alexey Kalinichenko
Square Role: Senior Staff Software Engineer/Tech Lead/Engineering Manager
Investors: Collaborative Fund
Capital Raised: $491.3M
Stage: Series C

Alexey is the co-founder and CTO at Step, he has a diverse background spanning engineering leadership and highly technical hands-on roles. Step is a financial services company that builds mobile-based banking for teenagers.


Founder: Pukar Hamal
Square Role: 1st Campus Ambassador for Stripe at Stanford University
Investors: Craft Ventures
Capital Raised: $21M
Stage: Series A

Pukar is a the founder and CEO at SecurityPal, which is the fastest platform for completing the Security Review so that companies can put the focus back on revenue.


Founder: Yishan Wong
Square Role: Consultant
Investors: San Altman
Capital Raised: $40M
Stage: Series A

Yishan is the CEO at Terraformation which is restoring the world's forests to build thriving communities and help solve climate change.

Capsule 8

Founder: Dino Dai Zovi
Square Role: Technical Lead, Information Security / Staff Security Engineer
Investors: Bessemer Venture Partners
Capital Raised: $30M
Stage: Series B

Dino was the co-founder of Capsule 8, a high-performance attack protection for Linux production environments.

Common Networks

Founders: Grace Chen, Jessica Shalek, Mark Jen, Zach Brock
Square Role: Product Lead, Head of Business Dev, Staff Engineer, Engineering Manager
Investors: Lux Capital
Capital Raised: $34.3M
Stage: Series B

All 4 co-founders worked at Square for a few years before co-founding Common Networks in 2016. Common Networks is a wireless internet service provider that brings fiber-class internet to homes.


Founder: Christophe Chong
Square Role: Software Engineer
Investors: GGV Capital
Capital Raised: $42.5M
Stage: Series B

Christophe is the co-founder and CTO of Kikoff, a personal finance platform that offers credit-building solutions and helping millions of Americans build credit, borrow, and grow!


Founder: Charlie Gao
Square Role: Engineering Manager
Investors: Bain Capital Ventures
Capital Raised: $1.5B
Stage: Series D

Charlie led engineering and co-founded one of the fastest growing unicorns- Lime, an electric scooter company.


Founder: Alan d'Escragnolle
Square Role: Head of Support Product, Cash App
Investors: Andreessen Horowitz
Capital Raised: $7.3M
Stage: Seed

Alan is he CEO and founder of Filmhub, a distribution platform for filmmakers and streaming channels. He is building the future of film distribution for producers, sales agents and distributors.


Founders: Jesse Reiss, Joe Robinson, Ryan Gerard
Square Role: Director of Engineering, Senior Product Manager, Online Stores
Investors: Battery Ventures
Capital Raised: $41.2M
Stage: Series B

Hummingbird is a platform for managing anti-money laundering and counter-terrorist financing operations. All three co-founders previously worked at Square before coming together in 2017 to start Hummingbird.


Founder: Tony Xu
Square Role: Intern
Investors: Sequoia Capital
Capital Raised: $2.5B
Stage: Public

Tony worked as a business developer at several big name companies such as eBay and PayPal. After his super short stint at DoorDash, he co-founded the incredibly successful food delivery platform, DoorDash.


Founder: Amir Nathoo
Square Role: Product Lead for Square Payroll
Investors: Tiger Global Management
Capital Raised: $240M
Stage: Series D

Amir loves building products and teams. He has been a part of projects like, Square Payroll, and now co-founder and head at Outschool which is a marketplace of live online classes for kids that connects learners, parents, and teachers together.


Founder: Christian Selchau-Hansen
Square Role: Product & Business
Investors: Starbucks
Capital Raised: $30M
Stage: Series A

Christian is the CEO, co-founder, and board director at Formation, which distills customer data into uniquely tailored experiences; they orchestrate physical and digital exchanges into one seamless journey.


Founder: Daniel Kao
Square Role: Business Development
Investors: Thrive Capital
Capital Raised: $44M
Stage: Series B

Daniel is the co-founder and CTO at TruckSmarter which is empowering truck drivers across the US through technology. He has previously been an ex-founder, early DoorDash/Square/Uber Freight employee.

Set Labs

Founder: Alex Soong
Square Role: Senior Software Engineer
Investors: Threshold
Capital Raised: $44M
Stage: Series A

Alex co-founded Set Labs in 2017 after working at companies like Square, Zynga, Caviar, and Apple. Set Labs is a crypto-financial platform that allows users to create baskets of cryptocurrency, NFTs, and on-chain securities.

Rising Stars


Founder: Rani Mavram
Square Role: Business Enamblement Tools
Investors: Y Combinator
Capital Raised: $4.1M
Stage: Seed

Rani is the co-founder and CEO at Compete, a company focusing on compensation. So far they have evaluated over 5,000 salaries and employee records to help their customers retain their top talent.


Founder: Doug Schuessler
Square Role: Director, Sales
Investors: Sequoia Capital
Capital Raised: $7.3M
Stage: Seed

Doug is the CEO at Safara which is  is reimagining hotel booking from the ground up! They offer the world’s first hotel carbon offsetting program—100% of the stays are carbon neutralized.

Ride Report

Founder:  William Henderson
Square Role: Director, Consumer Payments
Investors: Homebrew
Capital Raised: $13.4M
Series A

William has been a co-founder several times after working at Square for 3 years. In 2015 he co-founded Ride Report, a solution for cities to integrate new forms of micromobility.


Founder: Yunas Reguero
Square Role: Strategy & Operations
Investors: B Capital Group
Capital Raised: $5.5M
Stage: Seed

Yunas is the co-founder of Archie, a SaaS platform that allows businesses to onboard, manage, and pay creative freelancers on flexible terms. He previously worked at companies like Square, Facebook, and Accenture.

Thistle Technologies

Founder: Window Snyder
Square Role: Chief Security Officer
Investors: True Ventures
Capital Raised: $2.5M
Stage: Seed

Window is the founder and CEO of Thistle Technologies which is building tools that help connected device manufacturers build security resiliency into devices.


Founder: Kush Patel
Square Role: Developer Advisory Board
Investors: TechStars
Capital Raised: $4.5M
Stage: Seed

Kush is the co-founder and CTO at TheCut and has been a part of  Forbes 30 Under 30. TheCut is a mobile marketplace that connects barbers and their customers.

Stelo Labs

Founder: Aman Dhesi
Square Role: Software Engineer
Investors: Pear VC
Capital Raised: $6M
Stage: Seed

After working as a Software Engineer at Square, Aman co-founded Stelo Labs in 2022. The Stelo extension interprets and enriches transactions to keep users safe from crypto phishing, fraud and scams in the web3 space.

Join our waitlist
Love what we do? Give us a follow on: