5 Startup Founders Who Bounced Back After Failure

From failure to success, see how entrepreneurs like Katrina Lake and Howard Schultz overcame setbacks. Find inspiration and lessons for your startup.
jessica pedraza
Jessica Pedraza
Legal Consultant
Published: June 25, 2024
enterpreneur 2

What do the founders of Twitter, Starbucks, Uber, Stitch Fix, and Netflix have in common? They all faced failure and multiple setbacks before achieving success.

This blog dives into their stories and discusses how each person navigated unique challenges and overcame massive hurdles. Read on to learn these valuable lessons and figure out the best way forward for your startup!

1. Evan Williams – Twitter 

In 2005, Evan Williams co-founded a podcasting company Odeo. The idea was to create a platform where users could create, share, and discover podcasts. It made all the business sense at the time seeing how the podcasting market was growing, and Evan was ambitious enough to be at the forefront of this change.

But as fate would have it, Apple announced that iTunes would start supporting podcasts just as Odeo began to make a name for itself. The company could not compete with Apple's vast resources and existing user base, making its business model obsolete. 

Facing a seemingly impossible challenge, Williams knew something had to be done. He gathered his team and brainstormed new ideas, one of which was a simple social networking service centered around short, real-time status updates.

The idea eventually evolved into what we now know as Twitter. Williams, along with Jack Dorsey, Biz Stone, and Noah Glass, co-founded the new platform in 2006. Twitter initially started as a side project but quickly gained popularity because of its unique format (users could share their thoughts, updates, and news in 140 characters or less).

Twitter's growth was explosive, and it quickly became essential for real-time communication. It played a critical role during major events, from political campaigns to natural disasters, making it one of the biggest social media platforms ever.

2. Howard Schultz – Starbucks

Howard Schultz's journey to Starbucks success was filled with challenges. Initially, he tried to introduce espresso bars to Starbucks (a small coffee bean retailer at the time), but the owners were uninterested. However, Schultz remained undeterred and launched his own coffee shop, Il Giornale, in 1985. 

Financial constraints prevented the new business from taking off. Investors were skeptical and didn't believe that Americans would welcome an upscale Italian coffee experience.

Despite these setbacks, Schultz acquired Starbucks in 1987 and merged it with Il Giornale by securing capital through loans and investments​. He wanted to transform Starbucks from a coffee bean retailer into a coffeehouse serving as a "third place" between home and work. 

Under Schultz's leadership, Starbucks expanded rapidly. He introduced high-quality espresso beverages in a warm and inviting atmosphere, a combination that consumers liked, fueled rapid growth, and eventually opened the doors to global expansion.

But it wasn't all smooth sailing from there on out; Starbucks faced some serious hurdles, including severe criticism and financial difficulties. Schultz stepped down as CEO in 2000 but returned in 2008 to help the company navigate its financial crisis. He made key changes, including closing underperforming stores and renewing the focus on quality and customer experience, that eventually revitalized the company.

3. Travis Kalanick – Uber

Travis Kalanick’s entrepreneurial journey began with Scour, a peer-to-peer file-sharing company he co-founded in the early 2000s. Despite its innovative concept, Scour went bankrupt after facing a $250 billion copyright infringement lawsuit from the entertainment industry.

But that wasn't enough to stop Travis, who then founded Red Swoosh, a content delivery network to optimize internet traffic. The new venture faced its own struggles, including funding challenges and technical issues, but eventually succeeded when it was acquired by Akamai Technologies in 2007.

Kalanick's most significant venture came in 2009 when he co-founded Uber, a ride-sharing platform that revolutionized the transportation industry. The idea was simple yet transformative: connect riders with drivers through a mobile app. Uber quickly gained traction, expanding globally and changing how people moved around cities.

Like Starbucks, Uber's journey wasn't without challenges. The company faced regulatory battles, safety concerns, and controversies over its corporate culture. Kalanick himself was at the center of several scandals, leading to his resignation as CEO in 2017. Despite these hurdles, Uber continued to grow, becoming the modern phenomenon we know today.

4. Katrina Lake – Stitch Fix

Katrina Lake founded Stitch Fix in 2011 while attending Harvard Business School. Her business idea was based on the belief that traditional shopping was outdated and inconvenient.

She started by using SurveyMonkey to track customer preferences and personally delivered clothing, which wasn't efficient or scalable. During this early phase, Lake had to deal with many logistical hurdles and financial strains, but she kept pressing forward.

Securing funding was the main challenge, as most investors doubted whether her business model worked (it combined personal styling with data science). However, she eventually found backers who shared her vision, allowing Stitch Fix to integrate data for personalized customer experiences.

Stitch Fix thrived under this innovative approach, going public in 2017. Despite the success, the company faced class action lawsuits in 2018 that accused it of misleading investors about growth prospects. 

The COVID-19 pandemic in 2020 brought further challenges, resulting in an 18% workforce layoff. However, the company adapted by introducing new services like a "direct-buy" program, aiding recovery as e-commerce demand surged.

Under Lake's leadership, Stitch Fix took giant strides. From initial logistical challenges to becoming a publicly traded company, Lake's vision and resilience positioned Stitch Fix as a leader in personalized online shopping, continually adapting to market changes and customer needs. 

5. Reed Hastings – Netflix 

Reed Hastings co-founded Netflix in 1997 with Marc Randolph, launching it as a mail-order DVD rental service. The idea was inspired by Hastings' frustration with a late fee for a rented copy of "Apollo 13." He envisioned a rental service without due dates or late fees. 

In 2007, Hastings recognized the potential of streaming and pivoted Netflix towards digital content. This transition was challenging for several reasons. 

First, it required negotiating new licensing agreements with content providers, who were initially reluctant to grant streaming rights. Many providers were concerned about cannibalizing their existing DVD sales and television syndication deals​​.

Secondly, developing a robust technology infrastructure to support streaming was complex and costly. Netflix needed to ensure high-quality video delivery across various devices and internet speeds, which involved significant investment in servers, data centers, and content delivery networks. 

This was followed by extensive marketing efforts that highlighted the convenience and benefits of streaming to convince users to switch from physical DVDs to digital streaming. Yet despite these hurdles, Hastings and his team successfully executed the transition. They introduced a streaming service alongside the DVD rental business, slowly shifting the focus to streaming as it gained popularity.

As the company continued to grow, they started to face stiff competition from Hulu, Amazon Prime Video, Disney+, and others. To stand out, Hastings invested heavily in original content like "House of Cards" and "Stranger Things," which attracted and retained a large subscriber base​.

Expanding globally, Netflix also had to navigate diverse regulatory and cultural landscapes. Hastings' strategic focus on innovation and customer experience helped Netflix thrive in over 190 countries and solidified the company as the leader in the streaming industry.

Frequently Asked Questions

Is It OK to Fail as an Entrepreneur?

Yes, it is OK to fail as an entrepreneur. Failure is a natural part of the entrepreneurial journey and offers valuable learning experiences. Many successful entrepreneurs – like the ones mentioned in this blog – failed multiple times before achieving success.

What Is the Biggest Mistake Entrepreneurs Make?

The biggest mistake entrepreneurs make is failing to adapt to market changes. For example, ignoring customer feedback and market trends can lead to stagnation and missed opportunities for growth and innovation.

What to Do After a Startup Failure?

After a startup business failure, assess what went wrong, learn from the experience, and plan your next steps. Consider pivoting to a new business idea, seeking mentorship, or gaining additional skills and knowledge to increase your chances of setting up a successful startup. 

Note: Check out this guide on how to bounce back from financial loss after startup failure.


The stories of highly successful founders like Evan Williams, Travis Kalanick, Katrina Lake, Howard Schultz, and Reed Hastings clearly show that failure is often a stepping stone to bigger things. 

If you’re a startup founder who's struggling to stay afloat, perhaps shutting down the business is the right way to go. SimpleClosure has helped dozens of startups shut down and seen firsthand how some of those founders went on to fulfill their personal and financial goals and build successful businesses. 

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