Back in 2011,
@jack shared some insights into his entrepreneurial journey, talking about what inspired him and the core philosophies that guide him.
His journey began in St. Louis, Missouri, where he developed an obsession with maps and visualizing cities. This passion led him to teach himself programming to draw maps on a computer screen and later track real-time data from police scanners and CB radios, visualizing ambulances, fire trucks, and police cars moving through the city. He learned this type of software was called dispatch. This early fascination with visualizing a “city living and breathing” became a foundational influence.
Dorsey initially considered political science but switched to computer science after realizing he could see the effects of policies instantly through simulations. He continued building his dispatch system and eventually found work at DMS, the largest dispatch firm in New York City, after identifying and fixing a security vulnerability on their website. This experience solidified his focus on visualizing real-time data.
The idea for Twitter emerged in 2000 from his desire to visualize people within the city, inspired by instant messenger away statuses and LiveJournal.
His first prototype, using email from his Blackberry, failed because “no one cared what I was doing” and “no one else had a Blackberry.” He shelved the idea until late 2005 or early 2006, when SMS technology had become widespread in the U.S.
He loved SMS for its constraints and simplicity. The concept was simple: use SMS to share what you’re doing in real time, broadcast it to interested people, and archive it on the web, device-agnostic.
This idea, developed within the podcasting company Odeo, quickly led to the creation of Twitter. Dorsey says Twitter is still driven by curiosity about what’s happening right now everywhere.
The inspiration for Square came during the 2008 market crash, which created an opening in the payments industry. Dorsey reconnected with his first boss, a glass artist named Jim McKelvey, who lost a $2,000 sale because he couldn’t accept credit cards. They decided to solve this problem by building a prototype of a credit card reader that plugs into an audio jack, along with server software.
Key philosophies behind Square’s development include:
- Payments as Communication: Dorsey sees payments as a form of communication and an exchange of value. He found the existing financial systems, especially receipts, poorly designed.
- Redesigning the Receipt: Square aimed to transform the paper receipt into a medium that could provide useful information like social media handles, menus, and business hours.
- Rich Data for Merchants: Square wanted to provide offline merchants with analytics similar to Google Analytics, helping them understand their sales beyond just revenue.
- Marketing through Product: Square relied on word-of-mouth and feedback, targeting influencers like taco trucks to distribute their free device. Dorsey believes a beautifully built product markets itself.
- Transparency and Simplicity: Square disrupted traditional merchant accounts with free hardware/software, no hidden fees, and clear pricing—without requiring a separate merchant account.
- Payment Device Agnostic: Although Square started with credit cards, the goal was to improve the entire payment experience, preparing for technologies like NFC.
- Building Utilities that Scale: Both Twitter and Square were designed to scale from individuals to enterprises, minimizing friction in using them and focusing on the value being delivered.
Dorsey sees himself as a storyteller, emphasizing the importance of writing or drawing ideas to get feedback. He compares product development to writing a play and looks to companies like Apple for inspiration, calling them a “theater company” with cohesive storytelling.
As CEO of Square, he sees his role as editorial: selecting the most important ideas to pursue.
His three main priorities are:
1. Building the best team and maintaining cohesion.
2. Ensuring strong communication both internally and externally.
3. Managing finances—keeping money in the bank.
He sums up his management philosophy as: “Make every single detail perfect and limit the number of details.” He finds inspiration in small moments, like discovering his father’s old pizza restaurant now uses Square.
One of his guiding quotes is: “Expect the unexpected and whenever possible be the unexpected.”
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