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What is a Startup Mafia?

Have you ever heard of the PayPal Mafia or the Xoogler Mafia? These are nicknames for groups of people who worked together at companies like PayPal and Google.

After leaving, many of them went on to start or invest in new companies together. This tight-knit network is called a “startup mafia.”

In this post, we’ll explore what a startup mafia is, why they form, and how they can benefit the startup ecosystem. We’ll also look at some famous examples and drawbacks to consider.

What is a Startup Mafia?

A startup mafia refers to a network of entrepreneurs, investors, and employees who previously worked together at the same company. After leaving that company, many of them go on to start new companies or become investors in each other’s ventures.

The term “mafia” is used lightheartedly to describe their tight-knit relationships, ability to leverage shared knowledge and experiences, and support for one another’s endeavors.

Origins of the Startup Mafia

The origins of the startup mafia can be traced back to the early days of Silicon Valley. In the 1970s and 1980s, employees of companies like Fairchild Semiconductor and Hewlett-Packard began leaving to start their own ventures, often with the support and backing of their former colleagues.

However, the concept truly took hold in the dot-com era of the late 1990s and early 2000s. As companies like Netscape, Yahoo, and Google experienced meteoric growth and success, their early employees and founders became wealthy and sought new opportunities to leverage their expertise and resources.

Why Do Startup Mafias Form?

There are a few key reasons why startup mafias tend to emerge:

  1. Shared Experiences: When people work closely together over many years, they develop strong bonds. They’ve been through intense challenges and major successes as a team. This shared history creates a lasting connection.
  2. Skills & Knowledge: Through their employment, members gain unique skills, insider knowledge of specific industries/technologies, and an understanding of what it takes to scale a successful startup.
  3. Financial Resources: Early employees at big startup successes often become wealthy from stock options/ownership. This gives them capital to start new ventures or invest in others.
  4. Motivation: After experiencing a big exit, many get the itch to replicate that success by either starting a new company themselves or backing others trying to do the same.

Benefits of a Startup Mafia

While the “mafia” term may sound nefarious, these networks can provide immense value:

Trusted Relationships

Startups live or die by the quality of their team and investors. Startup mafias allow founders to bring on people they already know and trust from prior work experience.

Knowledge Sharing

Members can share hard-won lessons, advice, and industry expertise from their past successes and failures. This knowledge transfer helps new companies avoid preventable mistakes.

Talent Pool

Need to hire great engineers or marketers? Startup mafias can tap into a pre-vetted pool of talent from their prior company.

Investor Network

Having a tight-knit group of former colleagues who are now wealthy angel investors creates a ready pipeline of funds for new startup ideas.

Top 10 Startup Mafias

Here are some of the top startup mafias:

  1. PayPal Mafia:  This is perhaps the most well-known startup mafia, comprising former employees of PayPal who went on to establish successful companies such as Tesla (Elon Musk), LinkedIn (Reid Hoffman), Palantir (Peter Thiel), and many others. The PayPal Mafia has been credited with creating over $180 billion in public company value.
  2. Google Mafia (Xooglers): The Google Mafia, also known as Xooglers, is another influential group consisting of former Google employees. This network has raised over $115 billion and founded over 2,400 companies, including Anthropic AI, Horizon Robotics, and Nuro.
  3. Apple Mafia: The Apple Mafia has produced notable companies like WhatsApp (Brian Acton), LinkedIn (Reid Hoffman), and Salesforce (Marc Benioff), among others.
  4. OpenAI Mafia: This relatively new mafia comprises former employees of OpenAI who have founded 21 companies, mostly in the AI sector, and raised close to $40 billion. Notable startups include Anthropic, Living Carbon, and Perplexity AI.
  5. eBay Mafia: The eBay Mafia has spawned companies like YouTube (Steve Chen), ZipRecruiter, and GrubMarket, with a total of 472 companies founded and $16.5 billion raised.
  6. Microsoft Mafia: With 2,474 companies founded and $69 billion raised, the Microsoft Mafia has produced companies like Airbnb (Nathan Blecharczyk), Zillow (Rich Barton, Lloyd Frink), and Glassdoor (Rich Barton, Robert Hohman).
  7. Twitter (X): Mafia Despite recent changes at Twitter, its alumni have founded 334 companies and raised $55 billion, including Compass (Ori Allon), Block, Inc. (Jack Dorsey), and Abnormal Security (Evan Reiser & Sanjay Jeyakumar).
  8. Tesla Mafia: This group has founded 140 companies and raised $48 billion, with notable startups like Substack (Hamish McKenzie), Sila Nanotechnologies (Gene Berdichevsky), and Swell Energy (Suleman Khan).
  9. Amazon Mafia: With 774 companies founded and $34 billion raised, the Amazon Mafia has produced companies like Instacart (Apoorva Mehta), Hulu (Jason Kilar), and Flipkart (Binny Bansal).
  10. Facebook Mafia: The Facebook Mafia has started 748 companies and raised $18 billion, including OpenAI (Wojciech Zaremba), Yugabyte, and Dada Group.

These startup mafias have played a significant role in the tech industry, leveraging their shared experiences, connections, and resources to launch successful ventures and drive innovation.

Potential Drawbacks

While incredibly powerful, startup mafias aren’t without potential risks:


Too much reliance on the same tight-knit group can lead to insular thinking and rejection of outside perspectives that could be valuable.

Conflicts of Interest

Investing in each other’s startups creates conflicts where objective advice may be hard to provide. Members may be biased towards each other.

Lack of Diversity

If everyone comes from the same background/company, it can hinder diversity of thought, perspectives, and talent pipelines.

Unfair Advantages

Some argue startup mafias create an unfair playing field by giving their members easier access to talent, advice, and capital versus outsiders.


  • A “startup mafia” refers to a network of founders, employees, and investors who previously worked together at the same successful tech company.
  • They form due to shared skills, experiences, wealth, motivation and trusted relationships from their prior company.
  • Benefits include knowledge sharing, talent pipelines, investor relationships, and being able to quickly build new teams from trusted individuals.
  • Well-known examples are the PayPal Mafia (Elon Musk, Peter Thiel), Xoogler Network (Google alumni), and Paypal Mafia in India.
  • Potential downsides are groupthink, conflicts, lack of diversity, and unfair advantages over outsiders.


Q: Can anyone join an existing startup mafia?

A: Not exactly. These networks are usually limited to people who directly worked at the original company that sparked the mafia’s formation. However, new members can be brought in over time through acquisitions, investments, or by proving themselves as exceptionally talented collaborators.

Q: Do all big tech companies spawn a “mafia”?

A: No, not every successful tech company leads to the rise of a powerful startup mafia. The companies that tend to produce mafias are those that had a lasting major impact, created immense wealth for employees through an IPO or acquisition, and employed people with the motivation to branch out into entrepreneurship.

Q: Why the term ‘mafia? Are startup mafias legal?

A: The term “mafia” originally stems from the Sicilian word for “family.” These tight-knit networks have a similar family-like structure of mentoring, backing each other, and passing down experiences across “generations.”

There is nothing inherently illegal about startup mafias as long as they operate ethically and comply with all investing regulations. The “mafia” term is more of a lighthearted way to refer to their tight-knit relationships and cross-investments.

Startup Mafia Quiz

Test your knowledge of startup mafias:

  1. What does the term “startup mafia” refer to? A) A network of criminal organizations targeting startups B) A group of friends who start companies together C) Former employees/founders of a successful tech company who go on to start new ventures together D) Venture capitalists who only invest in startups run by their former colleagues

Answer: C

  1. Which of the following is NOT a key reason startup mafias form? A) Shared knowledge and experiences from their previous company B) The wealth created through IPOs/acquisitions gives them capital C) Government incentive programs encouraging these networks D) Strong bonds and motivation stemming from their prior company’s success

Answer: C

  1. What is a potential downside of startup mafias? A) Lack of available funding sources B) Too much diversity in thought and backgrounds C) Conflicts of interest when investing in each other’s companies D) Inability to attract top talent

Answer: C

  1. Which of these groups is considered one of the most influential startup mafias? A) Apple Mafia B) PayPal Mafia C) Amazon Mafia
    D) Facebook Mafia

Answer: B

  1. True or False: Startup mafias provide unfair advantages compared to outsiders by making it easier to access talent, capital and advice.

Answer: True

Scoring: 5 Correct: You understand startup mafias extremely well! Consider becoming an investor or entrepreneur.

4 Correct: Great job, you have a very solid understanding of what startup mafias are.

3 Correct: Not bad, you grasp the main concepts around startup mafias.

2 or fewer: You may need to re-read the content to understand startup mafias fully.

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