Famous Quote
“Delighting customers is a cheat code to growing a business.”
Why #75
Cohen built Chewy into the largest online pet retailer and sold it for $3.35B, then triggered the most famous short squeeze in history at GameStop. His story bridges e-commerce entrepreneurship and the retail investor revolution.
The Story
Ryan Cohen co-founded Chewy in 2011 and built it into the largest online pet retailer in the United States, selling it to PetSmart for $3.35 billion in 2017 — the largest e-commerce acquisition at the time. He then became the most famous activist investor of his generation by buying a large stake in GameStop, joining the board, and becoming chairman — a move that triggered the most spectacular short squeeze in stock market history.
Chewy's success was built on fanatical customer service. Cohen sent handwritten birthday cards to customers' pets, offered 24/7 customer support, and created an emotional connection with pet owners that Amazon couldn't replicate. The company grew from zero to $3.5B in revenue in just six years.
The GameStop saga of January 2021 made Cohen a folk hero to retail investors on Reddit's WallStreetBets. His cryptic tweets, his confrontation with short sellers, and the resulting squeeze that sent GameStop's stock from $20 to $483 in days turned Cohen into a symbol of retail investor rebellion against Wall Street. As GameStop chairman, he has pivoted the company toward e-commerce and digital transformation.
Key Achievements
Co-founded Chewy (2011) — largest online pet retailer in the U.S.
Sold Chewy to PetSmart for $3.35B — largest e-commerce acquisition at the time
Became GameStop chairman — triggered the 2021 short squeeze
GameStop squeeze: stock went from $20 to $483 in days
Built Chewy to $3.5B revenue in 6 years
Became a folk hero to retail investors worldwide
By the Numbers
$3.35B
Chewy Exit
$483/share
GameStop Squeeze Peak
$3.5B
Chewy Revenue at Sale
Millions
Reddit/WSB Followers
Fun Facts
He started Chewy in his mid-20s with no prior experience in pet products — he just loved his dog.
He is known for posting cryptic tweets (including memes and emojis) that GameStop investors analyze obsessively.
The GameStop short squeeze of January 2021 caused several hedge funds to lose billions.
He reportedly hand-wrote thank-you cards to Chewy customers and sent paintings of their pets.
He dropped out of college and started Chewy from Dania Beach, Florida.
Frequently Asked Questions
Who are the greatest entrepreneurs of all time?
The greatest entrepreneurs include Steve Jobs (Apple), Elon Musk (Tesla/SpaceX), Jeff Bezos (Amazon), Bill Gates (Microsoft), and Mark Zuckerberg (Meta). Each built companies that fundamentally changed how the world works — from personal computing and smartphones to e-commerce, cloud computing, and social media.
What makes someone a successful entrepreneur?
Successful entrepreneurs share several traits: the ability to identify unmet needs, willingness to take calculated risks, relentless execution, and resilience in the face of failure. They combine vision with practical problem-solving and are willing to persist long after most people would quit. Capital and credentials matter far less than most people think — resourcefulness beats resources.
Can you become an entrepreneur without a business degree?
Absolutely. Many of the greatest entrepreneurs had no business education. Steve Jobs dropped out of college. Richard Branson left school at 16. Sara Blakely was selling fax machines. Henry Ford had no formal engineering training. Jack Ma was an English teacher. What matters is not the degree — it is the ability to see an opportunity, build something people want, and persist through failure.
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