Forget PayPal, the real fintech mafia might be from Square

When people think about the most influential players in the startup world, names like Y Combinator, Sequoia Capital, or Andreessen Horowitz often dominate the conversation. These institutions have earned their reputations for nurturing talent, seeding transformative ideas, and building tomorrow's unicorns. However, one name that’s often overlooked in this context is Square. Quietly, but profoundly, Square has reshaped the startup ecosystem over the past 15 years—not just as a fintech juggernaut but as one of the most impactful, unofficial incubators of the modern era.

Founded in 2009 by Jack Dorsey and Jim McKelvey, Square began as a simple yet groundbreaking solution to democratize payment processing for small businesses. With its sleek card readers and software solutions, Square empowered entrepreneurs and independent vendors to compete on a level playing field with larger businesses. Yet, the company’s influence extends far beyond its initial mission of simplifying commerce. Square has fostered an ecosystem of talent and ideas that has given rise to an impressive “alumni network”—arguably on par with the legendary PayPal Mafia—that has seeded innovation across industries.

The Alumni Effect: A New “Square Mafia”

Just as PayPal’s alumni went on to create industry-defining companies like Tesla, LinkedIn, and YouTube, Square has quietly become the breeding ground for an elite cohort of entrepreneurs and leaders. The so-called “Square Mafia” has influenced a diverse range of industries, from logistics to real estate, education, and beyond. Here are just a few of the notable companies led or founded by Square alumni:

• DoorDash: Revolutionizing food delivery and last-mile logistics.
• Faire: Transforming wholesale commerce for small businesses.
• Opendoor: Disrupting real estate through instant home-buying.
• Anchorage Digital: A pioneer in institutional-grade cryptocurrency custody.
• Persona: Enhancing identity verification with a focus on privacy and security.
• Nextdoor: Building hyper-local social networks that connect neighborhoods.

This alumni effect underscores the cultural and intellectual capital Square has contributed to the broader startup ecosystem. Former employees have taken Square’s DNA of customer-centric design, rapid iteration, and operational scalability into their own ventures, fostering a ripple effect of innovation.

Square as an Experimental Playground

One of Square’s most unique contributions to the startup world is its willingness to experiment internally. Over the years, Square has incubated groundbreaking ideas that have spun off into standalone successes or inspired entire sectors.

• Cash App: Initially launched as a simple peer-to-peer payment platform, Cash App has evolved into a comprehensive financial services tool, redefining personal finance for millions of users. Its meteoric rise has paved the way for similar products and demonstrated the power of fintech to expand access to banking.
• Square Capital: Providing small businesses with loans based on transaction data, Square Capital not only showcased the potential of alternative lending models but also catalyzed a wave of fintech solutions targeting underserved businesses.

This experimental culture has established Square as more than just a company—it’s a breeding ground for transformative ideas and approaches that influence industries far beyond fintech.

A Cultural Legacy of Innovation

Square’s impact isn’t limited to the ventures it has directly or indirectly fostered. The company’s design-forward, accessibility-focused ethos has set a new standard for how startups approach product development and user experience. By emphasizing simplicity, scalability, and inclusivity, Square has influenced a generation of founders and operators who carry these principles into their own organizations.

Moreover, Square’s focus on empowering small businesses—arguably the backbone of the global economy—has inspired other startups to tackle similarly ambitious and impactful missions. This legacy of democratization and empowerment has left an indelible mark on the entrepreneurial landscape.

The “Unofficial Incubator” That Keeps Giving

While Square might not have the formal title of an incubator, its influence on the startup ecosystem is undeniable. From its role in nurturing top-tier talent to its culture of experimentation and innovation, Square has quietly positioned itself as one of the most important forces shaping the entrepreneurial world over the past 15 years. The companies and ideas born out of Square’s ecosystem continue to reshape industries and redefine what’s possible.

As we look to the future, Square’s fingerprints will likely remain on some of the most transformative ideas and ventures of the coming decades. Its contributions may be quiet, but their impact is anything but small. In the grand narrative of startup history, Square deserves recognition not just as a fintech giant but as one of the most significant, unofficial incubators of our time.

More Startups under the House of Square

DoorDash, Faire, Opendoor, OpenStore, Cockroach Labs, Persona, Nextdoor, Anchorage Digital, Divvy Homes, Found.com, Hummingbird, Lead, Nearside (Acquired by Plastiq), TruckSmarter, AngelList, Zeller, Cocoon, Ride Report, Capital, Meld, Patterns, Grid, Safara, Keeper, Graphite, Cable - Automate 2LOD Control Testing, Outschool, Diagram, Gumtap, Dada Group, 北京鳄梨科技有限公司(Avocado).