Startups VCs wished they funded!
Behind every billion-dollar valuation lies a rejection story. Discover how these startups turned 'no' into unstoppable success.
Don't miss the infamous rejection emails Airbnb got in the end—it's a masterclass in perseverance that every founder can learn from! 👇
This newsletter dives into the untold stories behind some of the world’s most successful startups—stories that often hide the hard-hitting rejections that came before triumph.
Companies like Airbnb, Uber, and Shopify were all once overlooked by investors who failed to recognise their potential. Yet, these entrepreneurs turned rejection into a billion-dollar opportunity, rewriting the very rules of entrepreneurship.
Here’s a closer look at these iconic startups that didn’t let early rejection define their journey.
1. Uber: From Overlooked to Global Phenomenon
Founders: Travis Kalanick, Garrett Camp
Overlooked By: Multiple VCs in early rounds
Visionary Investor: First Round Capital (Rob Hayes)
Initial Bet: $510,000 in 2010
Now Worth: $57 billion market cap
Uber’s early pitches were often met with skepticism. Investors doubted the scalability of a ride-hailing service dependent on private drivers. But First Round Capital took a leap of faith, investing $510,000.
Today, Uber operates in over 70 countries, proving that sometimes, the riskiest bets yield the highest returns.
2. FedEx: Betting on Overnight Delivery
Founder: Frederick W. Smith
Dismissed As: "Unfeasible" by multiple VCs
Believed By: Smith himself and family
Self-Funded: $4 million of his own money in 1971
Today's Valuation: $41 billion market cap
When Fred Smith pitched FedEx as an overnight delivery service, investors scoffed at the logistics. Instead of giving up, Smith turned to his family and used $4 million of his own money to launch the company.
Today, FedEx moves over 15 million packages daily—a testament to the power of self-belief.
3. Snapchat: Redefining Communication
Founders: Evan Spiegel, Bobby Murphy
Initially Snubbed By: Sequoia Capital
Spotted By: Lightspeed Venture Partners (Barry Eggers)
Early Investment: $485,000 in 2012
Current Worth: $18 billion market cap
When Snapchat’s founders pitched their idea of disappearing messages, even top-tier VCs like Sequoia failed to see the appeal. Barry Eggers at Lightspeed Venture Partners took a chance, writing a $485,000 check.
Today, Snapchat has become a cultural phenomenon, especially among Gen Z, with over 350 million daily active users.
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4. Zoom: Winning in a Crowded Market
Founder: Eric Yuan
Rejected Due To: "Crowded market" by multiple VCs
Backed By: WebEx and Cisco colleagues
Friends & Family Round: $3 million
Pandemic Darling Value: $21 billion market cap
When Eric Yuan pitched Zoom, most investors felt the video conferencing market was saturated. But Yuan’s conviction in creating a simpler, more user-friendly product won over friends and former colleagues who helped him raise $3 million.
By 2020, Zoom became a household name, connecting millions during the pandemic.
5. Shopify: Empowering Ecommerce Entrepreneurs
Founder: Tobias Lütke
Overlooked As: Just another ecommerce platform
Early Believers: Lütke's family and angel investors
Initial Capital: $450,000 combined from family and angels
Today's Empire: $76 billion market cap
Shopify began as a side project for selling snowboarding gear online. Dismissed by VCs as "just another ecommerce site," Tobias Lütke turned to angel investors and family for support.
Today, Shopify powers millions of online stores worldwide, redefining the ecommerce landscape.
6. Dell: Building a Legacy from a Dorm Room
Founder: Michael Dell
Ignored By: Institutional investors early on
Supported By: Dell's family
Started With: $1,000 from Michael Dell at age 19
Current Valuation: $52 billion market cap
Michael Dell’s vision to sell customized computers directly to consumers was dismissed as unscalable. Instead of giving up, he bootstrapped his business with $1,000 in savings.
Decades later, Dell is one of the largest PC manufacturers in the world.
7. Airbnb: Turning Rejection into Revolution
Founders: Brian Chesky, Joe Gebbia, Nathan Blecharczyk
Rejected By: 7 of the top 10 VC firms
Savvy Backer: Y Combinator (Paul Graham)
Initial Stake: $20,000 in 2009
Current Value: Over $100 billion market cap
When Airbnb’s founders pitched their idea of renting spare rooms for temporary stays, most investors dismissed it as a "quirky couch-surfing idea." Rejected by numerous VCs, they finally found support in Paul Graham at Y Combinator, who invested a modest $20,000.
The journey was far from smooth. The founders even sold custom cereal boxes just to keep the business alive. Fast forward to today, Airbnb has transformed the hospitality industry, becoming a global success.
Airbnb CEO Brian Chesky recently shared five rejection emails in a Medium post. Back in 2008, the company was raising $150,000 at a $1.5 million valuation, offering a 10% stake. That stake is now worth an eye-popping $25 billion—one of the biggest missed opportunities in Silicon Valley.
Here are the rejection emails of Airbnb that show how even the most promising ideas can be overlooked:
Conclusion:
Rejection is part of every founder’s journey. But as these stories show, rejection doesn’t define you—your response to it does. The next time someone says "no," think of Airbnb, Uber, or Shopify, and remember: one "yes" can change everything.
💡 Share this newsletter with someone who needs a little inspiration today!
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