“You wonder if you made the right call.” Aaron Levie Box “Hubris certainly plays a role.” Jeremy Stoppelman Yelp “There are a million personal decisions involved.” Dan Porter Omgpop “That unknown is what excites me the most.” Maggie Nemser BlackboardEats Clockwise from top left, Peter DaSilva and Jennifer S. Altman for The New York Times, Greg Cohen, Richard Drew/Associated Press Clockwise from top left, Aaron Levie, chief executive of Box; Dan Porter, the former chief executive of Omgpop; Maggie Nemser, founder and editor in chief of BlackboardEats; and Jeremy Stoppelman, center, co-founder and chief of Yelp.

The reactions last week flowed like those to a Rorschach test. Were the young founders of Snapchat, a mobile-messaging start-up, delusional for turning down a multibillion-dollar buyout offer? Greedy to think they might get more later? Or courageous to chase their dreams? The decision they faced — to cash out or remain independent — is one that all successful technology entrepreneurs eventually confront. The founders face cold business considerations: pressure from investors and workers who want liquidity, and complex calculations about timing in a dynamic industry. But the choices also involve ambition and exhaustion, competition and loyalty, dreams and reality. The successes get the attention. But Silicon Valley is littered with stories of companies that gave up money by rejecting offers and of those that sold too early. “It’s never obvious whether to sell or hold,” said Ben Horowitz, of the venture capital firm Andreessen Horowitz, an early investor in Instagram, which was co-founded by Kevin Systrom and sold to Facebook for $1 billion. “When Kevin sold Instagram, people said he was a genius, and now they’re asking whether he did it too early, and they’re saying Snapchat is so bold,” he said. “Who was right? We don’t know yet.” When Snapchat’s founders rejected the buyout offer, it conjured memories among start-up founders who once faced a similar decision. Nine recounted their thoughts in that moment — when the money was on the table and the future was unpredictable. Claire Cain Miller

Max Levchin PayPal Damon Winter/The New York Times Mr. Levchin at the offices of Slide in 2007. EBay came calling many times before it wore down PayPal’s founders enough to agree to a sale. “They would say, ‘You need to sell to us because it’s a natural synergy — and if you don’t we will compete you out of the way and kill you,’ ” said Max Levchin, a co-founder of PayPal. Each time, Mr. Levchin asked employees to “look into your soul to ask yourself, ‘How tired are you? Are you still ready to fight?’ ” he said. In 2002, after PayPal had gone public and “the fight with eBay had gotten really, really bloody,” it sold to eBay for $1.5 billion. “I have to admit, eBay has been a fantastic steward of what we built,” he said. “It’s one of the few deals in Silicon Valley history when the acquirer didn’t choke the party.” His next company, Slide, was a different story. It made social apps and sold to Google for $228 million. Google shut it down a year later. “The honest truth about Slide was we were a five-year-old company that had wandered through the desert for a long time wondering what business to be in,” said Mr. Levchin, who later started a new software company, HVF. “I wanted to top PayPal and it didn’t work.” Claire Cain Miller

Oren Etzioni Netbot and Farecast Stuart Isett for The New York Times Mr. Etzioni in his Seattle office. Oren Etzioni caught the start-up bug so many times while working as a professor of computer science at the University of Washington that it seems he will never shake it. All four of the start-ups he has helped found have been acquired, the most recent ones by eBay and Microsoft. There are some consistencies in his motivations for selling. Netbot, an early comparison-shopping service that was sold to Excite in 1997 for $35 million, was more a technology than a business, he said, and it was crying out to live inside a bigger company. Similarly, Dr. Etzioni said he sold Farecast to Microsoft in 2008 for $115 million largely because he wanted to see the service, which helped travelers figure out how to time their airline ticket purchases, reach a bigger audience. Farecast became the basis for Microsoft’s Bing Travel service. He said he had avoided selling start-ups to companies that insisted on the start-ups’ employees relocating from the Seattle area. And getting the highest price for his companies, he said, has not been his top priority. “I don’t want to sound holier than thou,” said Dr. Etzioni, who now leads the Allen Institute of Artificial Intelligence, a nonprofit research group. “I’ve never been focused on maximizing money.” Nick Wingfield

Philippe Courtot cc:Mail Qualys Mr. Courtot and his engineers built cc:Mail in the late 1980's. In 1990, Philippe Courtot got a call from Microsoft. Would he fly to Redmond, Wash., to meet with Bill Gates? Two years earlier, Mr. Courtot had started a company with $2,000 and, together with 12 engineers, was building a new email product called cc:Mail. Mr. Gates offered to buy his company for $12 million. “I think he multiplied one million times 12 engineers — that was the formula they were using to acquire companies back in the day,” Mr. Courtot recalled. “I told him the price was not enough. But it wasn’t just the price, we were on the verge of building the dominant e-mail platform.” Mr. Gates, the chief then, didn’t take the rejection lightly. “He told me, ‘If you don’t sell to me, we will be a very fierce competitor.’ ” The advantage Mr. Courtot had, he said, was that cc:Mail worked on multiple operating systems — on Mac OS, Windows and Unix — while Microsoft’s product worked only on Windows. For the next year, cc:Mail dominated Mr. Gates’s Microsoft Mail product until Mr. Courtot received a second acquisition offer, this time from Lotus Development for $55 million in cash. Under Lotus, cc:Mail grew from four million users to 24 million, until IBM acquired Lotus in 1995 and shut down cc:Mail. Microsoft Mail eventually became Outlook. “I should not have sold,” said Mr. Courtot, who is now chairman and chief executive of Qualys, a security company that went public last year. “That was my biggest regret. We could have moved much, much faster and brought it to the cloud. But such is life.” Nicole Perlroth

Jeremy Stoppelman Yelp Justin Lane/European Pressphoto Agency Mr. Stoppelman at the New York Stock Exchange after Yelp's initial public offering. The first time Yelp, the local reviews site, rebuffed an acquisition bid, an investor warned Jeremy Stoppelman, the company’s co-founder and chief executive, that he would now “have to build a real company.” “I was like, ‘Yes, yes, of course,’ ” Mr. Stoppelman said. “But I didn’t get the nuances of what that meant. It’s a lot of work.” He was 28, Yelp was almost two years old and without revenue, and the company making the bid, which he declined to name, offered $100 million. “Hubris certainly plays a role,” he said. Three years later, Google offered $500 million. The match seemed promising, but negotiations fell apart. “It ends up feeling a bit like brain damage to everyone involved,” he said, largely because people start dreaming about paying off mortgages. “Everyone had to shake off all those fantasies and get back to work, including myself.” “At that moment, I still viewed myself as young entrepreneur guy, not established public company C.E.O.,” he said. “When we chose that independent path, for me that was like, ‘All right, it’s go time, I’m going to have to be a real C.E.O.’ ” Yelp went public in March 2012. Its share price has since tripled, making it worth nearly $5 billion. Claire Cain Miller

Maggie Nemser BlackboardEats Greg Cohen Ms. Nemser In 2010, just a year after Maggie Nemser started BlackboardEats, which offers restaurant deals, she had a buyout offer from a bigger company. In the end, she decided not to sell. “It was like if you decided to marry the first person you went on a date with, you might wonder what else was out there,” she said. “There was a lot of me that was looking forward to someone else taking on the day-to-day headaches, like health benefits, and being able to focus on what I do best, which is the creative side,” she said. “But I didn’t want to look back and feel like there was so much more we wanted to do.” And the other company lacked her “creative spirit,” she said. “I would have been giving up a piece of the soul of the brand.” Now, though, she sees the advantages of having a bigger company’s resources. “That unknown is what excites me most,” she said. What about soul and creative spirit? “There are things founders should remain precious about because you know your audience better than anyone,” she said. “But I also think you have to be practical and run the business.” Claire Cain Miller

Ben Horowitz Opsware Peter DaSilva for The New York Times Mr. Horowitz at his Andreessen Horowitz office in Menlo Park, Calif. Ben Horowitz faced conflicting feelings in 2007 about selling Opsware, an enterprise software company that he co-founded. “There’s a logical piece and the emotional piece, and they’re very hard to untangle,” he said. His logic about selling the company remains solid, he said. The data center automation market was shifting and the economy was starting to tank. Also, Hewlett-Packard paid $1.6 billion. Yet even today, his emotions about selling are tumultuous. “I spent eight years, all day every day, trying to build this thing, and all of a sudden it’s gone, it’s just over,” he said. “It’s a little bit like something dies. “That decision was one of the most isolated and alone decisions you ever make,” said Mr. Horowitz, who now advises entrepreneurs as a venture capitalist at Andreessen Horowitz. “On the surface it looked good, but I tell you after I sold the company I had total seller’s remorse.” Claire Cain Miller

Dorothy McGivney Jauntsetter Robert Spychala Ms. McGivney outside her home. After leaving her job in Google’s advertising department in 2007, Dorothy McGivney started Jauntsetter, an online travel newsletter that highlighted the best things to do in New York. But Ms. McGivney, now 35, said she lacked the resources to expand into other markets. That was when she started searching for a company to buy her newsletter. “I wasn’t hitting the benchmarks I wanted to see,” she said. “So I realized it was time to find an acquirer and find a partner who can unlock the potential of this audience.” Finding the right suitor was difficult. Ms. McGivney said she did not want to offend Jauntsetter’s most valuable asset — its subscribers — by selling the newsletter to a company that would send unwanted messages. Eventually Ms. McGivney connected with Jake Dobkin, a founder of Gothamist, a popular news blog for New Yorkers, and felt it was the right fit. “Everyone I know reads Gothamist at least once a week,” Ms. McGivney said. “It felt really natural.” Gothamist acquired Jauntsetter this month for an undisclosed amount. Ms. McGivney is now searching for her next project. Brian X. Chen

Aaron Levie Box Peter DaSilva for The New York Times Mr. Levie at his company's headquarters in Los Altos, Calif., last year. “As life experiences go, turning down a lot of money is hard to replace,” said Aaron Levie, the co-founder and chief executive of Box, an online business data storage service. In 2011, Mr. Levie reportedly turned down hundreds of millions of dollars for his company. He was 26 years old, and the company was 6. Mr. Levie would not confirm the amount or the buyer, but said he went through negotiations with “a big tech company” for a price similar to what was reported. Selling would have made him phenomenally wealthy, he said, but he didn’t turn down the deal to make even more. “People in this situation are very, very rational about money, in an unusual way,” he said. “You don’t say no to a life-changing amount of money so that you might get a larger life-changing amount of money. I know it sounds untrue, but you think about it a lot, and you think more about the company and the mission than whether you should hang in there so you can someday afford two really big yachts, instead of one.” In his case, he said, “the mind-set was: Is this a once-in-a-lifetime opportunity to build something really new, create products and services that no one has had before? Are you better off doing that on your own, or can you do it better with the resources of a big company?” He chose to remain independent, he said, by studying companies that had been bought, and whether they seemed able to complete what they set out to do. Most of those companies didn’t complete what they wanted, he said, in part because the best talent is drawn to independent start-ups. After declining a big offer, “there’s two weeks that are pretty gut-wrenching, when you wonder if you made the right call,” Mr. Levie said. “You wonder if the phone will ring, if you’ll make a sale. Eventually you win more customers and grow, and you get conviction.” Quentin Hardy