6 Founders Who Pivoted When the First Plan Failed

Joseph McVicker, Jeremy Stoppelman, Brian Chesky, Andrew Mason, Jason Goldberg and Jason Citron each rebuilt around one signal from a failing first plan.

founders who pivoted case study
Case 1

Airbnb's launch at SXSW produced two bookings. Groupon grew out of a collective-action website that struggled through its first year. Below are six founders who pivoted when their original plan was wrong: what they noticed, how they re-planned, and what the pivot cost.

Founders are told to commit to a plan and are then praised for abandoning it. The evidence suggests the useful behavior sits between the two. A large replication study by Arnaldo Camuffo and colleagues, published in the Strategic Management Journal in 2024, followed 759 firms through four randomized control trials. Firms trained in a scientific approach to decision-making "made a few strategic shifts, as opposed to either not changing or constantly changing their strategy," and were more willing to terminate ideas that did not hold up.

The six founders below each made one decisive shift of that kind. In almost every case the signal came from inside the failing product: users writing reviews nobody had asked for, a group-buying use on a site built for activism, a weekly deals feature on a social network, a chat system built into a game, a schoolteacher using a cleaning product as modeling clay. The cases are ordered by date, and each records what the founders noticed, how they rebuilt, and what it cost.

Case Study #1: Joseph McVicker and the Customer Pivot That Turned Wallpaper Cleaner Into Play-Doh

Kutol Products was founded in Cincinnati in 1912 and became, in the early 20th century, the world's largest manufacturer of wallpaper cleaner, a soft, pliable compound for wiping soot off walls. By the 1950s its product was no longer in demand, and Joseph McVicker was trying to turn the struggling company around.

Snapshot

Founder

Joseph McVicker, with the idea from Kay Zufall

Company

Rainbow Crafts Company, a Kutol subsidiary (Play-Doh launched as a toy in 1956)

Model

The same compound, sold as a children's modeling toy

Scale

More than 3 billion cans sold since 1956

Philosophy

Sell the product to the customer who still wants it

The Challenge

Kutol's plan had worked for decades until home heating changed. As households moved from coal to oil, gas and electricity, sooty buildup on wallpaper stopped being a problem. Manufacturing had already been scaled back, and Christopher Bensch, vice president of collections at The Strong National Museum of Play, later put the position bluntly: "Kutol was headed down the drain at that point."

The Breakthrough

  • McVicker's sister-in-law, Kay Zufall, was a nursery school teacher looking for something easier for small hands than modeling clay. She had read an article about using wallpaper cleaner for holiday decorations, tested the non-toxic material with her pupils, and found that they loved shaping it. McVicker formed a subsidiary, Rainbow Crafts Company, and began marketing the old product under a new name suggested by Zufall and her husband, Robert.

  • Woodward & Lothrop, a Washington, D.C. department store, was the first to carry Play-Doh, and other department stores soon followed.

  • Sales soared in 1958 after televised advertising on children's programs; the host of Captain Kangaroo earned 2 percent of sales under an arrangement that never had a contract.

  • The Fun Factory extruder, introduced in 1960, is still sold, and the brand has passed 3 billion cans.

The pivot kept the same formula and the same factory and only needed a new buyer for the compound.

Results

The insight that saved the product came from outside management; by Bensch's account, Zufall is the toy's mother. McVicker applied for a patent in 1956 and was granted it on January 26, 1965, the same year Rainbow Crafts was sold to General Mills. Hasbro acquired the brand in 1991, and it entered the National Toy Hall of Fame in 1998. The owner of the formula needed an outsider to see its worth, and most of the brand's life has been spent under other owners.

Lessons & Playbook

McVicker's case is the new-customer playbook.

Key takeaways:

  • A product can outlive the market it was designed for.

  • The person who spots the new use is often an ordinary user.

  • Marketing paid as a share of sales can fund a launch without cash up front.

  • Protection granted years after launch may come too late to shape the outcome.

Case 2

Case Study #2: Jeremy Stoppelman, the Pivot Based on User Data That Built Yelp

In 2004 Jeremy Stoppelman and Russel Simmons founded Yelp at a business incubator, MRL Ventures. Their first product asked people to email friends for recommendations of local businesses. In the words of NPR's summary of the story, "The launch was a flop."

Snapshot

Founder

Jeremy Stoppelman, with Russel Simmons

Company

Yelp (founded 2004)

Model

Free crowd-sourced reviews funded by local advertising

Scale

Record 2025 net revenue of $1.46 billion

Philosophy

Follow what users actually do

The Challenge

The original design was an email-based referral network: a user asked friends for a recommendation and the answers were collected online. Fortune later called the system "convoluted." It was rejected by investors and attracted few users beyond the co-founders' friends and family. The plan assumed people would answer when asked. Most did not.

The Breakthrough

The usage data pointed elsewhere. Users ignored the requests for referrals and turned to a "Real Reviews" feature that let them write reviews nobody had requested. People, NPR summarized, "seemed to enjoy writing reviews not just for friends, but for the general public." The founders rebuilt the company around that behavior.

  • Yelp's stock began trading on the New York Stock Exchange on March 2, 2012.

  • In 2025 net revenue rose 4% to a record $1.46 billion, and net income rose 10% to $146 million.

  • Advertising revenue from services businesses rose 8% to a record $948 million.

The founders kept the audience and the data and discarded the mechanism they had planned around.

Results

In December 2009 Yelp was in the final stages of negotiations to be acquired by Google, at a price reported as about $500 million by one outlet and $550 million by another. The deal collapsed; TechCrunch later reported, citing two sources, that a Yahoo offer of $750 million had frozen the process. Google went on to build its own local reviews, and in August 2024 Yelp sued it. Stoppelman wrote that Google "manipulates its results to promote its own local search offerings above those of its rivals." In 2025 Yelp's advertising revenue from restaurants, retail and other businesses fell 6% to $444 million. A company built on reviews still depends on search traffic it does not control.

Lessons & Playbook

Stoppelman's case is the usage-data playbook.

Key takeaways:

  • Usage logs show which feature customers actually value.

  • A failed launch can still produce the asset the next plan needs.

  • A suitor that walks away may return as a competitor.

  • Dependence on another company's traffic is a risk the plan should name.

Case 3

Case Study #3: Brian Chesky, Airbnb's Pivot From a Failed Launch to Whole-Home Rentals

Brian Chesky and Joe Gebbia were designers struggling to pay rising San Francisco rents when a design conference came to town and hotels were booked solid. They advertised an empty room with an air mattress and found their first guests in October 2007. Nathan Blecharczyk, a software engineer, joined a few months later.

Snapshot

Founder

Brian Chesky, with Joe Gebbia and Nathan Blecharczyk

Company

Airbnb (first guests October 2007, San Francisco)

Model

Marketplace for stays in private homes

Scale

More than 5.5 million hosts and 2.5 billion guest arrivals

Philosophy

Widen the product until it matches what hosts offer

The Challenge

The first plan tied demand to events that filled the hotels. Airbed & Breakfast officially launched during SXSW in March 2008 and received just two bookings. The website launched again in time for the Democratic National Convention in August 2008 and took 80. Between events there was little to sell. As the company neared the end of its first year it was not making money, not growing and not attracting venture capital, and the founders kept sliding further into debt.

The Breakthrough

The rescue was a stunt. In the fall of 2008 the founders produced presidential cereals, Obama O's and Cap'n McCain's, and sold the boxes at $40 each, earning $30,000 that helped pay down their credit card debt. The publicity faded, but the stunt persuaded an accelerator that had doubted the idea to take them in. Hosts on the platform, too, began offering whole homes and unusual lodgings as well as spare rooms. In March 2009 the company changed its name to Airbnb and expanded to apartments, whole homes and vacation rentals.

  • An accelerator investment of $20,000 in January 2009 was followed within three months by a $615,000 seed round, and a year later by a $7 million Series A.

  • Airbnb became a publicly traded company in December 2020.

  • Hosts have earned more than $380 billion on the platform, according to the company's figures as of May 2026.

The product that worked was the one hosts had already started listing.

Results

The pivot removed the dependence on events. The dependence on travel stayed. In May 2020 Chesky wrote that revenue that year was forecast to be less than half of 2019's. The company raised $2 billion and cut costs, then announced that nearly 1,900 of its 7,500 employees, around 25%, would leave. It paused work on transportation and Airbnb Studios and scaled back hotels and luxury. Twelve years after cereal money kept it alive, one shock cost a quarter of its people their jobs.

Lessons & Playbook

Chesky's case is the widen-the-market playbook.

Key takeaways:

  • An event-led model sells only as often as the events happen.

  • Personal credit card debt buys time and proves nothing about demand.

  • Investors may back resourcefulness before they back the model.

  • A focused core is what remains when a crisis forces cuts.

Case 4

Case Study #4: Andrew Mason, the Group Buying Business Model Groupon Found Inside an Activism Site

Andrew Mason, a Northwestern University music graduate, unveiled The Point in late 2007 as a collective action and fundraising website. It struggled in its opening year. His former employer, Eric Lefkofsky, had provided the seed money.

Snapshot

Founder

Andrew Mason, with Eric Lefkofsky and Brad Keywell

Company

Groupon (launched 2008, Chicago)

Model

Discounted local deals sold to subscribers

Scale

IPO valuation of $12.7 billion in November 2011

Philosophy

Find the one use that already works and build around it

The Challenge

The Point was built on the "tipping point" principle, using social media to bring people together to accomplish a goal. It was meant to organize people around almost any cause, and that breadth was the problem. The site gained only modest traction in Chicago.

The Breakthrough

One group of users decided their cause would be saving money, rounding up enough people to buy the same product at a group discount. Lefkofsky wanted the company to focus entirely on group buying. Mason and his team carried The Point's tipping-point mechanism into retail and launched Groupon in 2008.

  • By May 2012 Groupon had amassed 150 million subscribers in nearly 50 countries.

  • In December 2010 Groupon was reported to have walked away from an offer of $5 billion to $6 billion from Google.

  • It went public in November 2011 at $20 a share, at a valuation of $12.7 billion.

The pivot kept the mechanism and changed what it was used for.

Results

At the end of February 2013 Groupon ousted Mason, the same day its stock slid 24% after a weak quarterly report; it had lost three-quarters of its value since the listing. His memo to staff was unusually candid: "I was fired today. If you're wondering why... you haven't been paying attention." Twelve years later, in 2025, Groupon reported revenue of $498.4 million and a net loss from continuing operations of $81.1 million, and its chief executive described a return to growth in billings and revenue "for the first time in a decade."

Lessons & Playbook

Mason's case is the narrow-the-platform playbook.

Key takeaways:

  • A general-purpose platform often succeeds through one specific use.

  • An investor who reads the data can push a pivot the founder hesitates over.

  • Rejecting a multibillion-dollar offer is a bet that the growth rate will last.

  • Public markets judge the model after the novelty has worn off.

Case 5

Case Study #5: Jason Goldberg, Fab and the Flash Sale Business Model That Scaled Too Fast

Fabulis launched in 2010 as a social network for gay men and raised a little under $1 million, followed by $1.75 million more in December 2010. By February 2011 Jason Goldberg and his co-founder, Bradford Shellhammer, were deciding whether to shut it down and return the money to investors.Snapshot

Founder

Jason Goldberg, with Bradford Shellhammer

Company

Fab (launched June 9, 2011)

Model

Design-led flash sales, later conventional online retail

Scale

$150 million raised at a $1 billion valuation

Philosophy

Build the company around the one thing that is working

The Challenge

Fabulis kept adding features and nothing worked. "We built a beautiful product, but it was frustrating because no one was using it," Goldberg said. Shellhammer was at a breaking point after a year. The one feature that drew attention was a weekly deals offer he curated, covering everything from magazine subscriptions to furniture. About $2 million remained in the bank.

The Breakthrough

Over a dinner in Manhattan, Goldberg drew a circle with three slices on a napkin: what the pair were most passionate about, what they could be best in class at, and which market could still be disrupted. The answer was design. The deals that worked on Fabulis would be combined with Shellhammer's taste in handpicked, well-designed objects. Before launch, membership reached 175,000 in two months with no sales at all, and Fab opened on June 9, 2011.

  • By November 2012 Fab was valued at around $600 million.

  • It went from nothing to $250 million in sales in two years.

  • It raised $150 million at a $1 billion valuation, taking its venture funding to $310 million.

The second plan reused the cash, the investors and the one feature that had traction.

Results

During its fastest growth Fab was burning $14 million a month. Shellhammer left a few months after the big raise. The company abandoned flash sales for conventional online retail, reportedly because it raised only half the $300 million it had sought. Staff fell from a peak of about 750 to around 30, and it was later set to be sold to PCH, an Irish manufacturer, in a deal that could be worth as little as $15 million. Goldberg moved on to a new venture, Hem. The first pivot was disciplined. The scaling that followed ran far ahead of the business.

Lessons & Playbook

Goldberg's case is the pivot-then-overreach playbook.

Key takeaways:

  • Investors who back a team will often stay through a first pivot.

  • One engaged feature can seed an entirely new company.

  • Rapid sales growth in discounting says nothing about margins.

  • A second change of model under cash pressure is harder than the first.

Case 6

Case Study #6: Jason Citron, the Gaming Startup Pivot That Turned a Game's Chat Into Discord

Jason Citron had sold his first company, OpenFeint, to Gree in 2011 for $104 million. In April 2012 he set up a new studio, Phoenix Guild, later renamed Hammer & Chisel, to build Fates Forever, a multiplayer online battle arena game designed for mobile.

Snapshot

Founder

Jason Citron, with Stanislav Vishnevskiy

Company

Discord (first version May 2015, from Hammer & Chisel)

Model

Free voice, video and text chat for groups

Scale

More than 200 million monthly active users

Philosophy

Build the tool the team needed for itself

The Challenge

Fates Forever launched in the summer of 2014 to critical acclaim. It won a lot of praise but did not get traction with players. Citron was frank about the outcome: "It was clear it wasn't going to be a big business." The studio had at least been careful with money. "We didn't burn a lot of money on marketing," he said.

The Breakthrough

The game included built-in voice chat, text chat and forums, and while building them the team noticed that voice and text chat for mobile had barely advanced in a decade. Citron shut the free-to-play game down. In May 2015 he and Vishnevskiy released the first version of a gaming-focused chat app for desktop and mobile called Discord.

  • By September 2015 the app was still in alpha testing and already drawing traction from players.

  • By 2025 Discord had more than 200 million monthly active users, who spend two billion hours playing games.

  • The company reported positive adjusted EBITDA for five consecutive quarters as of April 2025.

Careful spending on the failed game left enough money to build the product that worked.

Results

Three years separated the studio's founding from Discord's first release, and Citron described the end of the game as "a very emotionally difficult time." Nor did the second product settle the strategy: Discord expanded beyond gaming during the pandemic and afterward pivoted back to games. In April 2025 Citron stepped down as chief executive, handing the role to Humam Sakhnini while staying on the board. Asked about a public listing, he said there were "No specific plans."

Lessons & Playbook

Citron's case is the internal-tool playbook.

Key takeaways:

  • The tools a team builds for its own product can be the better business.

  • Spending carefully on a first product leaves runway for a second.

  • Critics can love a game that players skip.

  • A company that broadens during a boom may have to narrow again afterward.

Conclusion

The six cases share a mechanism. McVicker, Stoppelman, Mason, Goldberg and Citron each found the second business inside the first: a classroom use for a cleaning compound, an overlooked review feature, one popular cause on an activism site, a weekly deals offer, a chat system built for a game. Chesky's hosts widened the product before the company did. The first plan's real output was evidence of what customers would actually do, and the founders who pivoted well read that evidence and let the plan go.

The costs are as consistent. A pivot is paid for in time, cash and control: three years at Hammer & Chisel, credit card debt at Airbnb, a founder's job at Groupon, a company's independence at Fab and Rainbow Crafts. The replication study's finding fits the record: a few deliberate shifts beat both stubbornness and constant change. A plan written with its riskiest assumptions stated, and with the signal that would trigger a change named in advance, makes that first pivot cheaper and the second one less likely to be needed.