Jack Ma

"Today is difficult, tomorrow is more difficult, but the day after tomorrow is beautiful"

Most people know Jack Ma as the charismatic founder of Alibaba who became China's richest man, but few realize he was rejected from KFC—one of only three applicants turned down out of 24. This early rejection, along with failing his college entrance exam twice and being turned down for dozens of jobs, shaped his unconventional approach to business: embracing failure as education and seeing opportunity where others saw impossibility.

Timeline of Pivotal Moments

• 1988: Graduated from Hangzhou Normal University with English degree after two failed college entrance attempts
• 1995: First encountered the internet during a trip to Seattle; searched "beer" and found no Chinese results
• 1995: Founded China Pages, one of China's first internet companies, which ultimately failed
• 1999: Founded Alibaba in his Hangzhou apartment with 17 co-founders and $60,000
• 2003: Launched Taobao to compete directly with eBay's expansion into China
• 2004: Secured $82 million investment from SoftBank, giving up significant equity for growth capital
• 2008: Stepped down as CEO to focus on strategy during global financial crisis
• 2013: Launched Yu'e Bao money market fund, disrupting traditional banking in China
• 2014: Alibaba IPO raised $25 billion, largest in history at the time
• 2019: Stepped down as Alibaba chairman on his 55th birthday to focus on education and philanthropy
• 2020: Ant Group IPO was suspended after Ma's criticism of Chinese financial regulators

The Entrepreneurial Journey

The Unlikely Beginning

Jack Ma's path to becoming one of the world's most influential entrepreneurs began with a series of spectacular failures that would have crushed most people's ambitions. Born into a poor family in Hangzhou, he failed his college entrance exam twice before finally gaining admission to a local teachers' college. His early career was marked by rejection after rejection—he was turned down for numerous jobs, including a position at KFC where he was the only applicant rejected out of 24.

But these failures became his foundation. Ma developed an almost supernatural resilience and an ability to reframe setbacks as stepping stones. "I failed so many times, I became immune to failure," he would later reflect. This immunity would prove crucial when he encountered the internet in 1995 during a business trip to Seattle.

The Internet Revelation

When Ma first used the internet in 1995, he searched for "beer" and found results from Germany and the US, but nothing from China. He then searched for "China" and found virtually no information about his country online. In that moment, he saw not China's digital backwardness, but an enormous opportunity. While others saw the internet as a Western phenomenon, Ma envisioned it as the great equalizer that could connect Chinese businesses to the world.

His first internet venture, China Pages, failed spectacularly. But failure had become his teacher. He learned that in China, success required understanding both technology and the unique cultural and business dynamics of Chinese commerce. This insight would prove invaluable when he founded Alibaba.

Building Alibaba: The Apartment Revolution

In 1999, Ma gathered 17 friends and colleagues in his small Hangzhou apartment and pitched them his vision: create a platform where small Chinese manufacturers could sell to buyers worldwide. The presentation was passionate but the business model was unclear. Yet somehow, he convinced all 17 to quit their jobs and join him for $60,000 in startup capital.

Ma's approach was radically different from typical tech entrepreneurs. While others focused on technology first, Ma obsessed over solving real problems for real people. He spent countless hours talking to small business owners, understanding their struggles with international trade, language barriers, and trust issues. Alibaba wasn't built in a garage by programmers—it was built around kitchen tables by people who understood commerce.

The eBay War: David vs. Goliath

When eBay entered China in 2003 through its acquisition of EachNet, most observers assumed the American giant would crush local competition. eBay had unlimited resources, proven technology, and global expertise. Ma had none of these advantages, but he had something more valuable: deep understanding of Chinese consumer behavior.

While eBay charged listing fees and remained hands-off, Ma made Taobao free and built extensive customer service. When eBay prohibited direct communication between buyers and sellers, Taobao created instant messaging tools. Most crucially, when eBay relied on PayPal for payments, Ma recognized that Chinese consumers didn't trust online payments to strangers. He created Alipay, an escrow service that held payments until buyers confirmed satisfaction.

"eBay is a shark in the ocean, but I am a crocodile in the Yangtze River," Ma declared. "If we fight in the ocean, we lose, but if we fight in the river, we win." Within two years, Taobao had driven eBay out of China.

The Philosophy of Impossible

Ma's leadership style defied conventional business wisdom. He hired for attitude over aptitude, famously saying he preferred hiring people who were "simple and naive" because they would work harder to prove themselves. He banned PowerPoint presentations in meetings, insisting on handwritten proposals because "if you can't write it clearly by hand, your thinking isn't clear."

His decision-making process was equally unconventional. When advisors told him e-commerce wouldn't work in China because of poor logistics and low internet penetration, Ma saw these as temporary problems, not permanent barriers. When investors said Chinese consumers wouldn't shop online, Ma believed they simply hadn't been given the right platform.

"The very important thing you should have is patience," Ma explained. "Today is difficult, tomorrow is more difficult, but the day after tomorrow is beautiful. But most people die tomorrow evening."

Scaling Beyond Commerce

As Alibaba grew, Ma's vision expanded beyond simple e-commerce. He saw the platform as infrastructure for a new economy. Alipay evolved into Ant Financial, providing loans to small businesses that traditional banks ignored. Alibaba Cloud became China's dominant cloud computing platform. Cainiao revolutionized logistics across China.

Each expansion followed Ma's core philosophy: identify where the current system fails ordinary people, then build something better. When small businesses couldn't get loans, Ant Financial used transaction data to assess creditworthiness. When rural areas lacked delivery infrastructure, Cainiao created networks of local partners.

The Teacher's Heart

Despite his business success, Ma never abandoned his identity as a teacher. He approached business challenges like educational problems: How do you help people understand new possibilities? How do you build confidence in those who've been overlooked? His annual letters to employees read like lessons in entrepreneurship and life philosophy.

This teaching instinct shaped Alibaba's culture. The company's values weren't typical corporate speak but practical wisdom: "Customer first, employee second, shareholder third." When employees struggled with difficult decisions, Ma encouraged them to think like teachers: "What would help our customers learn and grow?"

Confronting Power

Ma's most controversial moment came in 2020 when he criticized Chinese financial regulators for stifling innovation. His speech led to the suspension of Ant Group's massive IPO and increased regulatory scrutiny of his businesses. Some saw this as Ma's downfall, but it revealed his core character: even facing enormous personal cost, he couldn't stay silent when he believed the system was wrong.

"If you want to be successful, learn from other people's mistakes, not their successes," Ma had often said. His own regulatory confrontation became a lesson in the delicate balance between entrepreneurial boldness and political reality in China.

Revealing Quotes

On embracing failure: "I failed so many times. When I failed, I said, 'This is good, I learned something.' When I succeeded, I was worried because I didn't learn anything from success."

On competition strategy: "Your competitor is not your enemy. Your competitor is your teacher. When you compete with others, you learn from them."

On hiring philosophy: "I hire people brighter than me, then I get out of their way. If you always hire people who are smaller than you, we shall become a company of dwarfs."

On long-term thinking: "We should never finish a book we're reading. If you finish it, you start to think you know everything. Always stay curious, always keep learning."

On his regulatory confrontation: "If we don't speak up for entrepreneurs today, our children will not forgive us. We cannot let fear guide our decisions when innovation is at stake."

Lessons for Today's Entrepreneurs

Jack Ma's journey offers several enduring insights for modern entrepreneurs. First, failure immunity is more valuable than early success—learning to extract lessons from setbacks while maintaining optimism creates unshakeable resilience. Second, deep customer empathy trumps technological sophistication—understanding real problems leads to solutions that people actually want to use.

His approach to competition—focusing on differentiation rather than direct confrontation—remains relevant in crowded markets. Rather than trying to beat competitors at their own game, Ma consistently changed the rules by serving underserved segments better.

Perhaps most importantly, Ma demonstrated that entrepreneurship is ultimately about expanding possibilities for others. The most sustainable businesses don't just capture value—they create new value for customers, employees, and society. His teacher's instinct to help others succeed became Alibaba's greatest competitive advantage and offers a blueprint for building businesses that matter beyond their financial returns.