The Twitter Mafia

July 21, 2023
Tech Mafias

Move Over PayPal Mafia. The Twitter Mafia is Here.

You’ve probably heard of the PayPal Mafia if you’re one of those people that keeps up with the tech startup industry. But hey, in case you're not, which is totally acceptable (or not ;-)), let's get you up to speed so you can understand the significance of the almighty TECH MAFIA, and why you should be keeping up with the tech giants from now on (hint: you can make money).

Quick lowdown:
The “PayPal Mafia” is a group of ex-PayPal employees who founded extremely successful and influential companies after working at PayPal in various roles. And even if you’re not a tech bro or tech sis, you’ll have heard of some of these companies.

We're talking about the likes of Tesla, YouTube, and LinkedIn (and a whole more), which were all started by people who used to work at PayPal. In fact, here’s the full story if you want to see exactly how many major companies were founded by previous PayPal employees, it’s phenomenal.

And what's more phenomenal is the incredible investment wins made by those who invested in their fellow employees' new startup ventures. In fact, if you're an aspiring angel investor or someone who wants to dip their toes in the high-end waters of VC funding, the best (and less riskier) way to start is by investing in the startups of those who you have worked with and those within your network.

Going back to the mafia stuff- the PayPal Mafia group might be the most famous one, but there’s a whole lot more you probably haven’t heard of. And that's how our Tech Mafia Series came to life. In this weekly series we’ll be covering the biggest tech giants and the entrepreneurial communities that have formed from them.

The Most Influential Founders & Companies from Ex-Twitter Employees.

Twitter is all the hype right now with Elon Musk's takeover - who knows what the future holds. But one thing that's for certain is that Twitter has had thousands of genius employees rotating through its doors since its birth in 2006. Let’s check out some of the biggest companies and a few rising stars to watch out for.

The Twitter Mafia

Companies Covered Below:

  • Compass
  • Square
  • Abnormal Security
  • Digits
  • Urban Company
  • CashApp
  • Color
  • D2iQ
  • Aura Frames
  • Envoy
  • Encantos
  • Savvy Wealth
  • Phantom Wallet
  • StreamNative


Founder: Ori Allon
Twitter Role:
Director of Engineering at Twitter
Investors: Thrive Capital, Founders Fund, IVP
Capital Raised:

Ori Allon co-founded Compass, one of the world’s proptech unicorns. The real estate technology company provides an online platform for buying, renting, and selling real estate assets. Compass became a publicly traded company in April 2021 with a valuation of $8.2 billion.

Since the start of 2018, Compass’s agent count has increased from roughly 2,000 to 10,000. Of those 8,000 new agents, around 51% came from acquired brokerages.

Block (prev. Square) and Cash App

Founder: Jack Dorsey
Twitter Role:
Founder & CEO
Investors: Sequoia Capital, GGV Capital, Tiger Global
Capital Raised: $500M+
Stage: Public

Probably the most popular startup with one of the most prolific founders, Jack Dorsey. Dorsey was the previous CEO of Twitter, before co-founding another two companies. Square, now called Block, Inc. helps all sizes and types of businesses to accept contactless payments, including all major credit and debit cards and mobile payments.

Cash App is owned by the Block and was also founded by Jack Dorsey. It is a mobile app-focused money transfer service which allows individuals to quickly receive and send money to other people from their mobile devices. It recently reported 70 million annual transacting users and US$1.8B in gross profit.

Abnormal Security

Founders: Evan Reiser & Sanjay Jeyakumar
Twitter Role: Product & Machine Learning, Systems Architect
Investors: Insight Partners, Greylock, Menlo Ventures
Capital Raised: $284M
Stage: Series C

Abnormal Security, a cybersecurity company that protects enterprises and organizations from targeted email attacks, was founded by Evan Reiser and Sanjay Jeyakumar. Before founding Abnormal Security in 2018, Evan led product and machine learning team at Twitter. His duties included large scale behavioral profiling and data security, privacy and strategy. Sanjay was the systems architect at Twitter responsible for the distributed data processing and machine learning systems that powered Twitter’s business.

Abnormal protects more than 5% of the Fortune 1000 and numerous notable companies including Xerox, Hitachi Vantara, Urban Outfitters, Groupon, Royal Caribbean International and Auto Club Group-AAA.


Founders: Jeff Seibert & Wayne Chang
Twitter Roles: Senior Director & Head of Consumer Product, Director of Product Marketing
Investors: Benchmark, GGV
Capital Raised: $97M
Stage: Series C

Digits is a fintech company building AI-powered accounting tools to help accountants automate their work and get deeper insights into crucial data. The founders of Digits, both ex-Twitter employees, have an impressive job history as well as impressive investment portfolios. Founder of Digits, Jeff Seibert, was a Senior Director and Head of Consumer Product for four years at Twitter, while co-founder Wayne Chang had four different Growth and Marketing positions in his four-year career there, including General Manager of Crashlytics, Global Head of Developer Experience, Director of Product Marketing, and Director of Product Strategy. He’s also a prominent angel investor in several successful companies.

Urban Company

Founder: Raghav Chandra
Twitter Role:
Software Engineer
Investors: Tiger Global, Dragoneer Investment Group, Wellington Management
Capital Raised: $446M
Stage: Series F

Raghav Chandra, co-founder of Urban Company, was a Software Engineer at Twitter (and Yelp). In 2014, Urban Company was born. The company's platform provides a marketplace to search for service professionals for different activities like salon and spa, photography, plumbing, servicing, and repairs, so clients can access affordable and quality services from the comfort of their homes.


Founder: Elad Gil
Twitter role: Vice President, Corp Strategy
Investors: General Catalyst, Initialized Capital, 8VC
Capital Raised: $482M
Stage: Series E

Color brings healthcare services to people, sidestepping the traditional healthcare infrastructure. Elad Gil, co-founder of Color, served as Vice President of Twitter between 2009 and 2012.


Founder: Florian Leibert
Twitter Role: Tech Lead
Investors: Andreessen Horowitz, Foundation Capital
Capital Raised: $247M
Stage: Series D

D2iQ was founded by Florian Leibert, and to say this guy has been around the block several times, would be an understatement. Florian was a Tech Lead for both Twitter and AirBnb, and has served as a Board Member and Investor in over ten companies. D2iQ develops software that simplifies Kubernetes lifecycle management, deployment to hybrid, multi-cloud, and edge environments and enables advanced application use cases.

Aura Frames

Founders: Abdur Chowdhury & Eric Jensen
Twitter Roles: Chief Scientist, Search Tech Lead
Investors: Spark Capital
Capital Raised: $40M
Stage: Series B

Aura Frames is a smart picture frame company founded by early Twitter employees Abdur Chowdhury and Eric Jensen. The company paved the way for digital photo frames which are Wi-Fi enabled and feature superior Ultra High-Definition (UHD) displays. Its WiFi-connected frames currently display more than one billion photos per day in total on the Aura app in more than 100 countries around the world.


Founder: Larry Gadea
Twitter Role: Infrastructure Engineer
Investors: Menlo Ventures, Initialized Capital, Andreessen Horowitz, Haystack
Capital Raised: $170M
Stage: Series C

Larry Gadea was an Infrastructure Engineer at Twitter before founding Envoy. Envoy offers products and solutions for enterprises to securely sign-in guests, manage deliveries, and organize meeting room bookings. Some of its biggest clients include Slack, Asana and Pinterest.

Rising Stars to Watch Out For


Founder: Nuria Santamaría Wolfe
Twitter Role: Head of Multicultural Market Strategy
Investors: Human Ventures
Capital Raised: $8.5M
Stage: Seed

Award-winning edtech platform Encantos was co-founded by Nuria Santamaría Wolfe, previously Head of Multicultural Market Strategy at Twitter. The platform helps connect kids with the world's best storyteachers to teach them 21st century skills. It has also been listed on Fast Company’s Annual List of the World’s Most Innovative Companies for 2021.

Encantos has received numerous industry awards and accolades from the AP, ASU GSV, CNN, Common Sense Media, Forbes, Kidscreen, Kirkus Reviews, NBC News, The New York Times, NPR, Parents Magazine, PublishersWeekly, Romper, School Library Journal, Univision and USA Today.

Savvy Wealth

Founder: Ritik Malhotra
Twitter role: Software Engineer
Investors: Index Ventures, Thrive Capital, Global Founders Capital
Capital Raised: $18M
Stage: Series A

Ritik Malhotra, co-founder of Savvy Wealth, was a Software Engineer at Twitter. He co-founded Savvy Wealth in 2021, adigital-first platform for financial advisors centered around modernizing human financial advice. Other new and existing investors include founders of Plaid, Instacart, Figma, Opendoor, Flexport and several other strategic partners.

Phantom Wallet

Founder: Brandon Millman
Twitter Role: Phantom Wallet
Investors: Andreessen Horowitz
Capital Raised: $118M
Stage: Series B

Brandon Millman, founder of the popular crypto wallet Phantom, worked for some of the biggest tech names before swiftly moving into the Web3 space. In addition to being a Senior Engineer at Twitter, he was also part of the Software Engineering teams at Zynga Mobile and Cisco Systems.


Founder: Sijie Guo
Twitter Role: Software Engineer
Investors: Sequoia Capital, Sequoia Capital China,
Capital Raised: $29M
Stage: Series A

Sijie Guo, founder of StreamNative, worked as a Software Engineer at Twitter for four years. In 2019 he started StreamNative, a cloud-native messaging and event-streaming platform.