Founders Dilemma
One of the most important criteria we evaluate before investing and backing any startup, is the founders ability of resiliency and adaptability.
This article was inspired by one of our backed companies that is currently pivoting. The most critical decision an entrepreneur faces is determining when to stay the course versus when to change direction. Staying the course requires resilience and belief in the original vision, but can be risky if market conditions, customer needs, or technology evolves beyond the initial plan. Conversely, pivoting at the right moment can open new opportunities, but it demands sharp insight, humility, and a willingness to abandon prior investments (both time and money). Successful entrepreneurs are those who master the balance between perseverance and adaptability, recognizing when persistence will pay off and when changing direction is essential for growth or survival. The ability to make this decision is often what separates enduring businesses from those that fail.
The ability to make this decision and to navigate this crossroads, to listen deeply to your instincts and the market, is the defining moment in every entrepreneurial journey—the moment that transforms challenge into opportunity, failure into breakthrough.
Here’s a 40+ list of the many examples of great pivots.
- Shopify from online snowboarding store to global leader in online retail solutions
Shopify began as an online snowboarding store, but founders Tobias Lütke and Scott Lake faced challenges with existing e-commerce tools. They pivoted to develop an e-commerce platform, empowering other businesses to easily sell online. Despite early struggles with gaining traction, Shopify grew into a global leader in online retail solutions, helping millions of entrepreneurs. Today, Shopify has a market cap of $84.5 billion, supporting businesses around the world. Learn more at shopify.com.
2. Nintendo from playing card company
Nintendo, founded by Fusajiro Yamauchi , began as a playing card company in 1889. Despite early success, it faced setbacks when its arcade ventures struggled in the 1980s. However, Nintendo successfully pivoted to the home gaming market with the Nintendo Entertainment System (NES), and later iconic franchises like Super Mario and The Legend of Zelda. This transition made Nintendo a global leader in video games, with a current market cap of $50.3 billion. Learn more at nintendo.com.
3. Groupon from the Point, a platform for social activism,
Groupon initially started as The Point, a platform for social activism, but it struggled to gain traction. The founders, Andrew Mason , Eric Lefkofsky, and Brad Keywell, successfully pivoted the company into a daily deals platform, offering discounts to consumers. Despite setbacks like over-expansion and competition, Groupon became a leader in the local e-commerce space. While the company’s market cap is now down to $150 million, their pivot remains a notable story of adaptation. Learn more at groupon.com.
4. Netflix from DVD/CD rental to on-demand video streaming
Netflix began as a DVD rental service by mail but successfully pivoted to streaming in 2007, revolutionizing the entertainment industry. Recognizing the shift towards digital content consumption, Netflix invested heavily in streaming technology and, later, original programming. Hits like Stranger Things and The Crown propelled the company to global success. Today, Netflix is a leader in on-demand video streaming, with a market cap of approximately $179.2 billion. Visit them at Netflix.
5. Twitter from Odeo, a podcasting platform to the global platform for news, conversation, and social engagement
Twitter began as Odeo, a podcasting platform in 2005. When Apple launched iTunes, Odeo struggled to compete. In response, co-founder Jack Dorsey pivoted the company in 2006 to focus on a microblogging service where users could post short, real-time messages. This pivot resulted in the creation of Twitter, which quickly became a global platform for news, conversation, and social engagement. Despite multiple challenges, Twitter has remained influential, and in 2022, it was acquired by Elon Musk and is now private. For more details, visit Twitter.
6. PayPal from cryptography for mobile devices to global leader in digital payments
PayPal, founded by Elon Musk, Peter Thiel, and Max Levchin, initially struggled as Confinity, focusing on cryptography for mobile devices. After realizing the limitations of this market, they pivoted to become an online payment service. Despite early fraud concerns and legal challenges, PayPal gained massive success after being adopted as the preferred payment method on eBay. Today, PayPal has a market cap of around $67.3 billion, making it a global leader in digital payments. Learn more at paypal.com.
7. Slack from Tiny Speck’s communication tool to a leading solution for business messaging and productivity
Slack began as an internal communication tool for a video game company called Tiny Speck. When the game failed, the founders recognized the value of the chat tool they had developed and pivoted to turn it into a standalone workplace communication platform. This shift revolutionized team collaboration, making Slack a leading solution for business messaging and productivity. Acquired by Salesforce for $27.7 billion, Slack remains a key player in modern workplace communications. For more information, visit Slack.
8. Airbnb initially started to rent out air mattresses during a design conference
Airbnb was founded by Brian Chesky, Joe Gebbia, and Nathan Blecharczyk as a platform to rent out air mattresses during a design conference. Initially, the company faced significant setbacks, including low traction and failed products like Airbnb Experiences. However, they successfully pivoted into a global platform for short-term home rentals, overcoming challenges and growing into a hospitality giant with a current market cap of $74.5 billion. Despite setbacks, Airbnb transformed the travel industry. Learn more at airbnb.com. Connect with the founders: Brian Chesky, Joe Gebbia, and Nathan Blecharczyk.
9. Samsung initially sold rice and noodles and dried fish
Founded by Lee Byung-chul in 1938 as a trading company, Samsung initially sold rice and noodles and dried fish. Over the years, Samsung faced setbacks, including struggles in industries like textiles and retail. However, the company successfully pivoted into electronics in the 1960s, eventually becoming a global leader in smartphones, semiconductors, and home appliances. Despite challenges, Samsung’s innovation-driven approach now places its market cap at $337.8 billion. Learn more at samsung.com.
10. HubSpot started as SEO tool
HubSpot, founded by Brian Halligan and Dharmesh Shah, initially faced challenges as a SEO tool with limited market reach. Realizing the need for a more comprehensive marketing platform, they pivoted to create an inbound marketing and CRM suite that revolutionized digital marketing for small businesses. Despite early setbacks, HubSpot’s user-friendly tools led to massive growth, propelling its market cap to $25.2 billion. Today, HubSpot is a key player in the marketing technology space. Learn more at hubspot.com.
11. Flickr as online multiplayer game
Flickr began as part of an online multiplayer game created by founders Caterina Fake and Stewart Butterfield . After the game failed, they successfully pivoted Flickr into one of the first major photo-sharing platforms, redefining online photography. Despite setbacks, including acquisition and competition from Instagram, Flickr made its mark in digital media. Currently owned by SmugMug, Flickr no longer has a market cap as it is privately held. Learn more at flickr.com.
12. Fujifilm from photographic film into healthcare, cosmetics, and pharmaceuticals
Fujifilm, founded by Kazuo Shiraga in 1934, initially thrived in the photographic film industry but faced a massive setback with the digital photography revolution, which threatened its core business. Instead of succumbing to the decline, Fujifilm successfully pivoted into healthcare, cosmetics, and pharmaceuticals, leveraging its chemical expertise. Today, the company is a leader in these fields, with a market cap of $18.3 billion. Fujifilm’s adaptability and innovation turned potential failure into success. Learn more at fujifilm.com.
13. Nokia from making rubber and cables to telecommunications infrastructure and 5G technology
Nokia, founded in 1865 as a paper mill by Fredrik Idestam and Leo Mechelin , initially found success in manufacturing rubber and cables. The company later pivoted to become a global leader in telecommunications, dominating the mobile phone market. However, after failing to adapt to smartphones, Nokia faced significant setbacks. In recent years, Nokia successfully pivoted again, focusing on telecommunications infrastructure and 5G technology. Today, Nokia has a market cap of $25.4 billion, embracing its roots in technology and innovation. Learn more at nokia.com.
14. Western Union from Telegram Company global money transfers
Western Union, founded by Ezra Cornell and others, initially thrived as a telegram company but faced setbacks when the telephone industry overtook telegraph services. The company successfully pivoted by leveraging its extensive communication network to focus on global money transfers, becoming a leader in remittance services. Today, Western Union continues to dominate the cross-border payment space with a market cap of $6.2 billion. Despite its early challenges, Western Union adapted to stay relevant in a changing world. Learn more at westernunion.com.
15. Play-Doh from wallpaper cleaner company
Play-Doh originally began as a wallpaper cleaner in the 1930s but faced declining sales as homes transitioned from coal heating to gas. Recognizing an opportunity, the company pivoted its product to become a children’s modeling compound used in arts and crafts. This shift led to widespread success, and Play-Doh became a beloved household brand. Today, it is owned by Hasbro, with the parent company valued at $12 billion. Learn more at playdoh.hasbro.com.
16. Wrigley, from selling soap to chewing gum
Wrigley, founded by William Wrigley Jr. , initially sold soap and baking powder, but after noticing that customers preferred the chewing gum given as a promotional item, Wrigley pivoted entirely to selling gum. This pivot led to massive success, turning the brand into the world’s largest gum manufacturer. Despite early setbacks, the company’s focus on chewing gum created iconic products like Juicy Fruit and Doublemint. Wrigley, now part of Mars, Inc., continues to dominate the market, with Mars having an estimated valuation of $40 billion. Learn more at wrigley.com.
17. Avon from selling books to becoming the most popular names in makeup
Avon is one of the most popular names in makeup, founded by David H. McConnell, originally sold books door-to-door but struggled to generate significant interest. McConnell noticed that customers were more interested in the free perfume samples he offered alongside the books. He quickly pivoted the business to focus on selling beauty products directly to consumers through a network of sales representatives. This change propelled Avon into becoming one of the most recognizable brands in direct sales. Currently, Avon is part of Natura &Co, with a market cap of approximately $6.9 billion. Learn more at avonworldwide.com.
18. Suzuki started as a loom manufacturer to Automobile
Suzuki, founded by Michio Suzuki in 1909, initially started as a loom manufacturer for Japan’s silk industry. Facing setbacks as demand for looms declined, Suzuki successfully pivoted to producing motorcycles in the 1950s, and later expanded into automobiles, becoming a global brand known for its compact cars. This strategic pivot turned Suzuki into a major player in the global automotive industry. Today, Suzuki boasts a market cap of around $15 billion. Learn more at suzuki.com.
19. HP from audio oscillator personal computers and printers
HP, founded by Bill Hewlett and David Packard in a garage, initially struggled with their first product, an audio oscillator. Their breakthrough came when they pivoted to manufacturing test and measurement equipment, which gained traction in the engineering and defense sectors. Over time, HP successfully pivoted again into personal computers and printers, becoming a global tech leader. Today, HP Inc. has a market cap of around $33.2 billion. Learn more at hp.com.
20. Android initially started as a platform for digital cameras to the Android mobile operating system
Android, founded by Andy Rubin and his team, initially started as a platform for digital cameras, but faced early setbacks as the market for connected cameras didn’t take off. Recognizing this, they pivoted Android into a mobile operating system for smartphones, which caught the attention of Google. Google acquired Android in 2005, and it now powers the majority of the world’s smartphones. Today, Android is part of Alphabet Inc., with a market cap of $1.6 trillion. Learn more at android.com.
21. Brex originally launched as a virtual reality startup corporate credit cards for startups
Brex, founded by Henrique Dubugras and Pedro Franceschi, originally launched as a virtual reality startup but quickly faced setbacks in gaining traction. Realizing the challenges, they pivoted to creating corporate credit cards for startups, designed to provide businesses with easy access to credit. This pivot proved highly successful, making Brex a major player in fintech, now offering a full suite of financial services for companies. Brex is currently valued at around $12 billion. Learn more at brex.com.
22. Lambda Labs initially focused as facial recognition APIs to high-performance AI infrastructure and GPU cloud services
Lambda Labs, co-founded by Stephen Balaban, initially focused on facial recognition APIs and AI tools, but faced setbacks as the demand for their initial product didn’t scale. Recognizing the growing need for GPU infrastructure in AI and machine learning, Lambda Labs successfully pivoted to providing high-performance AI infrastructure and GPU cloud services. This pivot transformed them into a leading provider of AI hardware solutions. Lambda Labs is still privately held with an estimated valuation of $4 billion. Learn more at lambdalabs.com.
23. CoreWeave from cryptocurrency mining to a world leader in GPU-based cloud services for AI, VFX, and machine learning
CoreWeave, founded by Michael Intrator, Brian Venturo, and Brent Biscoe, initially focused on cryptocurrency mining using GPUs. As cryptocurrency mining became less profitable due to market volatility and hardware competition, they faced significant setbacks. Recognizing the potential in high-performance computing, CoreWeave pivoted to provide GPU-based cloud services for AI, VFX, and machine learning, becoming a leader in this specialized market. CoreWeave is now a major player in the GPU cloud space, valued at $2 billion. Learn more at coreweave.com.
24. Dropbox from basic storage to collaboration tools and business services
Dropbox, co-founded by Drew Houston and Arash Ferdowsi, initially started as a file synchronization service to solve Houston’s frustration with USB drives. Despite early success, Dropbox faced setbacks as tech giants like Google and Microsoft entered the cloud storage market with free offerings. Dropbox pivoted by expanding its focus from basic storage to collaboration tools and business services, differentiating itself in the crowded market. Today, Dropbox has a market cap of $9.6 billion. Learn more at dropbox.com.
25. Coca-Cola initially started as a medicinal tonic
Coca-Cola, created by Dr. John Stith Pemberton in 1886, initially started as a medicinal tonic but failed to gain traction as a health product. After realizing its potential as a refreshing beverage, Coca-Cola pivoted to focus solely on soft drinks, becoming one of the world’s most iconic brands. Despite early competition and challenges in expanding internationally, Coca-Cola thrived by diversifying its product line and marketing strategies. Today, Coca-Cola has a market cap of $265 billion. Learn more at coca-cola.com.
26.Pepsi originally started as a digestive aid called “Brad’s Drink.”
Pepsi, founded by Caleb Bradham in the 1890s, originally started as a digestive aid called “Brad’s Drink.” Despite initial success, the company faced setbacks during World War I due to sugar rationing, leading to bankruptcy in 1923. Pepsi pivoted in the 1930s by rebranding and focusing on affordable pricing, turning it into one of the world’s leading soft drink brands. Today, PepsiCo has diversified into snacks and beverages with a market cap of $246 billion. Learn more at pepsico.com and find Caleb Bradham’s LinkedIn here (if available).
27. Tesla from Roadster, an electric sports car to the mass-market electric vehicles with the Model S and Model 3
Tesla initially faced setbacks with the launch of its Roadster, an electric sports car that struggled with production delays and high costs. However, Tesla successfully pivoted to mass-market electric vehicles with the Model S and Model 3, revolutionizing the automotive industry. This shift, combined with innovations in energy storage and autonomous driving, propelled Tesla to a market cap of $746.4 billion. Despite early challenges, Tesla’s vision of sustainable transportation has become a reality. Learn more at tesla.com.
28. Instagram from Burbn, the location-based check-in app to global social media platform
Instagram, founded by Kevin Systrom and Mike Krieger, initially launched as Burbn, a location-based check-in app. After realizing users were primarily interested in its photo-sharing feature, the founders pivoted to focus solely on images, leading to Instagram’s success. Despite early challenges in a crowded social media space, this shift turned Instagram into a global platform, eventually acquired by Facebook for $1 billion. Today, Instagram is one of the most influential social media platforms, contributing to Meta’s market cap of $793.7 billion. Learn more at instagram.com.
29. IBM from Personal Computers to Global leader in IT services and cloud computing.
IBM, founded by Charles Ranlett Flint, initially dominated the hardware market with personal computers but faced setbacks in the 1990s as the PC market declined. The company successfully pivoted to become a leader in IT services and cloud computing, particularly through its Watson AI and enterprise solutions. Despite challenges, IBM’s focus on software and services revitalized its business, giving it a current market cap of $135.4 billion. IBM’s shift from hardware to services showcases its ability to adapt to changing markets. Learn more at IBM.com.
30. Honda from Bicycles
Honda began as a small company producing motorized bicycles in post-war Japan, but faced setbacks when its early motorcycle models struggled to gain traction in the U.S. market. The company, founded by Soichiro Honda , pivoted to target the off-road motorcycle market, where it found great success with the Super Cub. Honda later expanded into automobiles, becoming a global leader in both motorcycles and cars. Today, Honda’s market cap stands at $54.7 billion, symbolizing its resilience and innovation. Learn more at honda.com.
31. YouTube, from video dating platform
YouTube, originally created as a video dating platform by founders Chad Hurley, Steve Chen, and Jawed Karim, faced early setbacks as users uploaded general videos rather than dating content. Realizing the potential, YouTube pivoted to become a general video-sharing platform, revolutionizing online media. Acquired by Google in 2006, YouTube has grown into a global video giant with a current market cap under parent company Alphabet of $1.6 trillion. This pivot cemented YouTube as the world’s largest video platform. Learn more at youtube.com.
32. Qualcomm initially focused on satellite communications to global leader in mobile chipsets
Founded by Irwin Jacobs and Andrew Viterbi , Qualcomm initially focused on satellite communications but faced setbacks in gaining market traction. The company pivoted to mobile technology, developing the CDMA standard, which revolutionized cellular communications and established Qualcomm as a global leader in mobile chipsets. Despite competition and technological challenges, their innovations in 4G and 5G helped drive Qualcomm’s success. Today, Qualcomm boasts a market cap of $120.4 billion. Learn more at qualcomm.com.
33. NVIDIA initially focused on graphics chips for gaming to dominating the AI GPUs
Founded by Jensen Huang, Chris Malachowsky, and Curtis Priem in 1993, NVIDIA initially focused on graphics chips for gaming, facing early competition and challenges in the rapidly changing tech space. However, the company successfully pivoted by expanding its GPU technology beyond gaming into AI, data centers, and autonomous vehicles. This shift into high-performance computing propelled NVIDIA’s market cap to an impressive $2.6 trillion. Despite early setbacks, NVIDIA is now a leader in AI hardware. Learn more at nvidia.com and connect with the founders like Jensen Huang.
34. Reddit from aggregating links to global social media platform for communities
Reddit was founded by Steve Huffman and Alexis Ohanian as a social platform for aggregating links. Initially, it struggled to gain traction against competitors like Digg, but Reddit successfully pivoted by embracing user-generated content and community-driven discussions. This transformation helped Reddit become a leading social media platform for niche communities. Despite early challenges with monetization, Reddit is now valued at $10 billion. Explore more at reddit.com.
35. Pinterest from Tote to a leading social media platform
Pinterest, founded by Ben Silbermann , Evan Sharp , and Paul Sciarra, initially started as a mobile shopping app called Tote. The app struggled to gain traction, leading the founders to pivot toward creating a visual discovery platform focused on sharing ideas through images. This shift turned Pinterest into a global hub for inspiration, from home design to fashion, despite early setbacks. Today, Pinterest boasts a market cap of $14.5 billion, evolving into a leading social media platform. Learn more at pinterest.com.
36. Facebook from a social network exclusive to college students
Facebook, founded by Mark Zuckerberg, initially started as a social network exclusive to college students. After early setbacks like privacy issues and competition from MySpace, Facebook successfully pivoted by opening the platform to the general public and expanding into mobile. Over time, the company diversified through acquisitions like Instagram and WhatsApp, evolving into a social media giant. With its push into the Metaverse, Facebook (now Meta) continues to innovate, boasting a market cap of $793.7 billion. Learn more at meta.com.
37. Twitch from Justin.tv to global leader in eSports and gaming streaming
Twitch began as Justin.tv, a live streaming platform focused on general content, but faced challenges in attracting and retaining viewers. Founders Justin Kan and Emmett Shear pivoted the platform in 2011 to focus on video game streaming, leading to explosive growth in the gaming community. Despite early obstacles, this pivot transformed Twitch into a dominant force in the live-streaming industry, with a current valuation of $15 billion. Today, it’s a leader in eSports and gaming content. Learn more at twitch.tv.
38. Yelp from email-based recommendation service
Yelp, founded by Jeremy Stoppelman and Russel Simmons , began as an email-based recommendation service, which struggled to gain traction. However, they successfully pivoted to a user-generated business review platform, becoming a go-to source for restaurant and business recommendations. Despite competition from Google Reviews, Yelp thrived by focusing on local businesses and user interaction. Today, Yelp has a market cap of $2.3 billion, maintaining its relevance in the crowded review space. Learn more at yelp.com.
39. Marvel from Book Publisher
Marvel started as a comic book publisher in the 1930s, but by the 1990s, the company faced bankruptcy due to market oversaturation and poor financial management. However, under the leadership of founders Martin Goodman and later Stan Lee, Marvel pivoted to film production, launching the Marvel Cinematic Universe (MCU) with Iron Man in 2008. This shift transformed Marvel into a global entertainment powerhouse, with a market cap of $4 billion after being acquired by Disney. Despite early setbacks, Marvel’s cinematic pivot redefined the superhero genre. Learn more at marvel.com.
40. Apple from Personal Computers
Apple, founded by Steve Jobs and Steve Wozniak, initially gained success with personal computers like the Apple II but faced major setbacks in the 1990s as they struggled with innovation. The company’s successful pivot began with the release of the iPod in 2001, transforming the music industry and setting the stage for the revolutionary iPhone in 2007. Despite earlier challenges, Apple’s innovation in mobile devices and services has driven it to a market cap of $3.4 trillion. Apple’s shift from computers to consumer electronics reshaped its future. Learn more at apple.com.
41. Sony from Rice Cookers
Sony, founded by Masaru Ibuka and Akio Morita , started as an electronics company producing rice cookers, but faced setbacks with several failed products. The company pivoted successfully by entering the consumer electronics market with innovations like the Walkman, transforming how people listened to music. Despite facing stiff competition from Apple’s iPod, Sony remained a leader by leveraging its PlayStation and entertainment divisions. Today, Sony’s market cap stands at $111.6 billion. Learn more at sony.com.
42. Starbucks from selling coffee machines
Starbucks, founded by Gordon Bowker, Jerry Baldwin, and Zev Siegl in 1971, initially sold coffee beans and equipment. Under Howard Schultz’s leadership, Starbucks pivoted to focus on the coffeehouse experience, offering brewed coffee inspired by Italian cafés. Despite some failures, like the Unicorn Frappuccino and Starbucks Evenings, the company’s core pivot to in-store coffee sales led to global success. Today, Starbucks has a market cap of $109.3 billion. Learn more at starbucks.com and connect with Howard Schultz on LinkedIn.
43. Amazon from online Book Store
Amazon, founded by Jeff Bezos, started as an online bookstore, but quickly pivoted into e-commerce and later into cloud computing with Amazon Web Services (AWS), which now dominates the cloud market. Despite setbacks like the failed Fire Phone and Amazon Destinations, Amazon successfully expanded into diverse sectors, including streaming, AI, and logistics. These pivots helped Amazon achieve a market cap of $1.8 trillion. Their ability to innovate and adapt through failures drove long-term success. Learn more at amazon.com.
44. Uber initially launched as a black car service
Uber, founded by Travis Kalanick and Garrett Camp, initially launched as a black car service but successfully pivoted to a ride-sharing platform, revolutionizing urban transportation. Despite setbacks such as regulatory challenges and failed ventures like UberRush (same-day delivery) and UberElevate (air taxis), the company expanded into Uber Eats, a highly successful food delivery service. Today, Uber has a market cap of $92.3 billion and continues to evolve its services. Learn more at uber.com.
45. Google from a search engine
Founded by Larry Page and Sergey Brin, Google started as a search engine but successfully pivoted into a tech giant with products like Android and Google Cloud, transforming industries. However, it faced setbacks with failed products like Google Glass, Google+, and Google Wave. Despite these missteps, Google (now under Alphabet Inc.) boasts a market cap of $1.6 trillion. Today, Google dominates digital advertising, mobile operating systems, and cloud computing. Learn more at google.com.
46. Lyft initially started as Zimride, a long-distance carpooling platform
Lyft, founded by Logan Green and John Zimmer , initially started as Zimride, a long-distance carpooling platform. Facing slow growth, the founders pivoted to focus on ride-hailing with Lyft, offering shorter urban trips and a more user-friendly experience. Despite setbacks like the failed Lyft Shuttle and Lyft Bikes, the pivot to ride-sharing helped Lyft establish itself as a major player in the transportation industry. Today, Lyft has a market cap of around $4.5 billion. Learn more at lyft.com.
47. Microsoft, from BASIC programming language, to a OS Powerhouse
Microsoft’s first product, released in 1975, was a version of the programming language BASIC for the Altair 8800 microcomputer, developed by founders Bill Gates and Paul Allen. While starting as a software company focused on programming languages, Microsoft successfully pivoted into operating systems with the release of MS-DOS and later Windows, becoming a global tech giant. The company’s most significant pivot came with Azure, its cloud computing platform, transforming it into a leader in cloud infrastructure. Today, Microsoft has a market cap of approximately $3.0 trillion.