One blustery afternoon in March, I meet Emma Weisberg for coffee near her apartment on Manhattan's Upper West Side, at a diner called Utopia. Weisberg is petite, energetic, and warm, with thick brown hair that falls to her shoulders. Three years ago, she gave up a secure job at Google to go all in with Blinkbuggy. It's a free online baby book, a digital vault for storing pictures and videos of your kids that Weisberg, 38, dreamed up when she became a mother. For a while, Blinkbuggy was her very own utopia. She raised a million dollars, built a beautiful product, won a coveted slot at a big-time  startup accelerator, nailed her presentation on demo day, and spent much of last summer in heady conversations with angels and VCs, fully expecting funding for the next stage of Blinkbuggy's growth.

That's as far as she got. Everybody loved Blinkbuggy--how could they not? It's cuteness to the nth degree. Several did their due diligence. But in the end, nobody else wrote a check. User growth stalled, revenue never materialized, the money ran out. She had to lay off everybody. Her husband, Liad Spiro, who had ditched his job to manage Blinkbuggy's finances around the same time Weisberg left hers, returned to salaried work. Now Weisberg's interviewing. She needs a paycheck. Anything to keep Blinkbuggy alive.

Weisberg's not giving up. "Maintenance mode" is how she describes Blinkbuggy's current status. Sometimes she cops to "sort of mid-fail," which is admirable but doesn't convey the full, hard truth: Weisberg launched a business into which she poured her heart and soul. And she  failed.

That's hardly shocking or even unusual. Most entrepreneurs do. Even Henry David Thoreau, who despised commerce, was sufficiently clued in to refer, in Walden, to what's "been said of the merchants, that a very large majority, even ninety-seven in a hundred, are sure to fail .... " An exaggeration, perhaps, but only a slight one. CB Insights, a venture capital database, recently looked at 1,027 tech companies that raised seed money in 2009 and 2010. By the end of 2015, 77 percent were either dead, presumed dead, or self-sustaining--that is, still in search of investors.

A success rate of 23 percent doesn't sound like bad odds. And even among the self-sustainers, a lucrative exit via a sale or an IPO is still possible. They could be anywhere on the spectrum from "between rounds" to "slowly dying," says CB Insights research director Marcelo Ballvé. Nevertheless, the flailing-not-yet-failing almost certainly count as major disappointments to their investors. "VCs are looking for outsize returns," says Ballvé, "and these are companies that have either withered away or stalled along the way. They are the exhaust of the VC process." And, more broadly, of capitalism.

VCs play this game willingly because the big capitalist engine belching exhaust and leaving behind piles of roadkill is the same one that occasionally produces mega-winners like Instagram, Uber, and  Slack--three companies among nine in the cohort of 1,027 (0.9 percent) that have emerged with billion-dollar valuations. Failure happens; otherwise there's no risk. Without risk, there can be no reward. That's just the way it works.

As a culture, we accept the stunning ubiquity of failure because we can see the upside. Failure as an opportunity for entrepreneurs to  learn. Failure as a character builder. Failure as an interest-earning deposit in the bank of experience. Failure is what has to happen, a lot, if we care about innovation and growth, which we absolutely do. Our legal system bends over backward to make failure survivable. Not all countries are like that. "Sweden has a safety net for everybody in society except the entrepreneurs who fail, which seems ironic," says Dean Shepherd, who teaches entrepreneurship at Indiana University's Kelley School of Business. "In the United States, we reward people who try. That has a substantial benefit for our economy."

But lately, we've made a bizarre leap from tolerating failure, which is reasonable, to fetishizing failure, which is absurd. Somehow we got to a place, says Cassie Phillipps, founder of FailCon--itself the emblem of failure's esteemed status--where "it's almost a badge of honor to fail the first time." Where choosing to fail fast marks you as highly evolved. Where we can attend an event called Fuckup Night in Mexico City, whose organizers discovered that "sharing stories of failure was liberating. It was fun and authentic." Or Fail Night in Kansas City, Missouri, a "somber, supportive, and celebratory meeting," hosted by the Kauffman Foundation. Where embarrassingly confessional startup postmortems are all the rage online, and the former NFL quarterback Fran Tarkenton, whose whole post-football shtick is motivational fireworks, can write a book called The Power of Failure. Where the May 2016 cover of Harvard Business Review promises to teach us "How to Really Learn From Failure." Really.

Can we take a deep breath, please? Failure is not what anybody wants. Redefining failure as a virtue ignores a basic lesson we've all been taught since we were kids: Don't give up. Indeed, "most successful companies go through ups and downs," says Jonathan Axelrod, managing director of Entrepreneurs Roundtable Accelerator in New York City. "Founders' being persistent is our No. 1 success factor."

Failure may be an option in Sunnyvale, California, or Palo Alto, where privilege protects against consequence and there's always money for the next deal, but "let's not confuse that with the way 99.5 percent of businesses operate," says Walter Simson, who consults for Midwest manufacturers. "You cannot tell me in Milwaukee that failure is a requirement for success." Failure burns capital, opportunity, and time. It can leave emotional scars that "obstruct our ability to learn and to move on," says Shepherd. And it really, really hurts. Just ask Emma Weisberg.

"You cannot tell me in Milwaukee that failure is a requirement for success." Walter Simson

Blinkbuggy's birth story coincides with another: that of Weisberg's first child, Ciela, in 2009. Weisberg set Ciela up with her own Gmail account and began filling her inbox with notes, pictures, and archival tidbits, tagged with key words for easy retrieval through the decades. All her new-mom pals thought that was pretty cool. Soon they were copying her. That got Weisberg thinking about a more elegant approach. A way for tech-savvy Millennials to create permanent keepsakes for their kids, without scissors and glue. Like Facebook but more focused, and without the privacy leaks.

Weisberg was cautious and disciplined. She released an early, outsourced version of the website in time for Mother's Day 2013, but she kept her day job, and she told Google's compliance department (if not her direct report) what she was doing in her spare time. "Initially it was just, 'Let's build it,'" Weisberg says. "Then, as I started doing that, and doing all the diligence and the market research, and pulling the numbers together, and considering a business plan, I started thinking, 'This can be a big deal. I can make a lot of money doing this.'"

The projections she shared with potential backers envisioned quickly gathering 100,000 users (15,000 paying) and reaching $2 million in revenue by 2015 and $6 million by 2016. (Profits later, of course.) One West Coast investor who participated in the initial friends-and-family round--and who no longer wants to be publicly identified with a loser--says he always thought Weisberg was underestimating how much capital she'd need to hit her targets, but no matter: "We felt conservatively they could get to a $5 million valuation, which was double the buy-in." He promised to match whatever Weisberg could gather elsewhere. Her parents stepped up, big time. Friends pitched in. Blinkbuggy raised $500,000; Weisberg gave notice.

With her Google pedigree, her intimate identification with the target market (Micah, her second child, was born in 2011), and her passion, Weisberg was very attractive to investors. Her husband, less so. He had no tech cred, no entrepreneurial bent. Before Blinkbuggy, he was working remotely in New York for a big life-sciences company based in North Carolina, and he wasn't happy with his work. Weisberg wanted him with her. "I would not have taken this step by myself," Spiro says. "It made me nervous. But I believed in the idea, I believed in Emma, and personally, I needed something new. I couldn't keep doing what I was doing."

Weisberg and Spiro spent the first few months working side by side with a team of software developers at Pivotal Labs. Not cheap, but the payoff was real: a much improved website and Blinkbuggy's first mobile app. In early 2014, they moved to a  WeWork in SoHo and began staffing up. "This is an incredible adventure!" Weisberg remembers feeling. "I love this! We're raising money, Liad's leaving his job. It was happening."

But there were disquieting early indicators. Blinkbuggy is internet priced: free. Absent subscription revenue, the only conceivable appeal it has to investors, partners, or buyers is if it's growing--that is, attracting lots of users willing to upload photos and videos and otherwise engage with the site. Finding those users was harder than Weisberg had thought it would be. Everybody liked the idea of Blinkbuggy. Some liked it enough to register. Not many stayed active. What Weisberg kept hearing from moms was, "Oh, I have to be better about it!"

The more Weisberg fretted about her user base, the less inclined she was to even consider asking people to pay for it. That spoke to doubts her father had voiced from the start. Jeffrey Weisberg is a physician turned entrepreneur who co-founded a successful chain of urgent care clinics. He says that when his daughter and son-in-law came to him with their idea, he thought it sounded "nice," sure, but he didn't understand how it was ever going to make money. "I did try to emphasize again and again, 'This is a business, not a hobby. It's not going to make it unless you make a profit,'" he says. "I kept hearing about all the wonderful things they were developing. Software and video and a mobile app. I just let that drift by. It didn't hit the area I thought was critical, the selling of it."

"Well, Dad," he heard more than once, "you don't know the digital world." After a while, Dad kept his thoughts to himself and agreed to sign some big checks. "For obvious reasons," he says, "not because I believed in the company. I wanted to support her, and I hoped I was wrong."

By the late summer of 2014, Blinkbuggy was running out of money. After a year without any income, things were tight at home, too. "It was just bad all around," says Weisberg. "We thought we would have the growth metrics to raise the next round easily, and it was becoming clear to me that there was no way we were going to be able to hit those kinds of numbers." Weisberg thought maybe her husband should find a regular job again. That would buy her more time. Spiro wasn't ready yet. As long as there was still movement, he says, "it felt like a bad time to jump out."

Then, a minor miracle. A surprise phone call from Spiro's old boss at a company he'd worked for years earlier. "We sold the company," the boss told him. For $600 million. Spiro still owned stock. His share came to around $200,000. Enough to support the family for a while and keep Blinkbuggy alive.

"We decided we could go another year with no salary," Weisberg explains one evening at her apartment, while the nanny gets the kids ready for bed, "which, in retrospect--"

"I don't regret it," says Spiro, gently interrupting. "I don't regret it."

Weisberg says she was "sort of offended" the first time a VC suggested she consider applying to an  accelerator program. She thought Blinkbuggy was past that stage. Then again, the goalposts had moved. A reasonable target for Series A used to be $1 million. Now with tech stocks soaring and VCs on the hunt for unicorns, it was closer to five times that. Nobody was going to give Blinkbuggy $5 million.

ERA's Axelrod, however, was intrigued. Blinkbuggy had been around longer than most companies he'd seen and had raised more money, but was "still trying to achieve liftoff," he says, "trying to figure it out." He liked Weisberg--her experience, her vision, her smarts. And he liked the mom market, even if it was already crowded. What it came down to, he says, was a pretty simple question: "Could they get enough customers to break through the noise?"

Blinkbuggy was one of 10 companies chosen from about 1,000 ERA applicants in early 2015. They each got $40,000 (in exchange for 8 percent of the equity), a place to work for four months, cloud hosting, and lots of help figuring stuff out from mentors and alumni. Weisberg needed to build her user base. ERA pushed her to lock in a marketing partnership with Mom365, a company that photographs newborns in the hospital. ERA also got her thinking about ways to keep her users engaged without asking too much of them. That led to the development of TimeLapse, an automated feature that prompts you to upload a video clip once a week and makes a movie about your growing child.

"I started thinking, 'This can be a big deal. I can make a lot of money doing this.'"

By demo day in April, Weisberg had every reason to feel confident. Two funds with ERA ties and a Google bigwig, hoping to beat the buzz, had come in early with a total of $225,000. Weisberg had trained for weeks with her ERA mentors to get over her dread of public speaking. Standing before a room full of reporters and deep-pocketed investors, she did a good job. People applauded, and not just at the end. "All signs pointed to a positive outcome," says one of the new backers who got in on demo day eve--he's not saying who he is--"and then nothing happened."

Weisberg got plenty of first meetings, some follow-ups, and zero follow-through. "A total brick wall," she says, and now she knows why. Blinkbuggy was still spinning its wheels. Yes, the Mom365 partnership was a meaningful fix. In time, it would more than double the size of Blinkbuggy's online community. But it was expensive; plus, she signed that deal literally the day before demo day. All she could point to during her pitch were 20,000 beta users. TimeLapse was also meaningful and very cool. But also brand new. She had nothing to show for it yet.

Revenue remained a monumental challenge--Blinkbuggy still didn't have any. At least Weisberg was no longer in denial about that. Her inspired solution was  BlinkPix, a $10-per-month subscription service that makes prints from pictures on your phone and mails them to your parents and in-laws. But BlinkPix wouldn't be ready for another eight months, and by then there would be no money left to market it. Current subscribers: about 100.

All the VCs who introduced themselves to Weisberg on demo day ultimately passed. Same with all the angels she tried next. Almost worse than the outright refusals were the callbacks that turned out to be teases. "We would get the first affirmation," Weisberg says. "Like yes, OK, go to the next round. You'd do anything for it to come through. And then no one wants to be the first. People want to know if other people are investing, and it starts feeling like a downward spiral. You just know you're giving off a desperation vibe."

Now the poison was spreading to her personal life. Spiro's telling her there's no money left--she's got to cut the team and unwind the Mom365 partnership. Weisberg doesn't want to hear it. Then again, she knows he's right. "So we talk about it," she says, "but then it's like a not-good interaction, so I try to avoid the conversation. We're talking about the numbers, and then we're dropping it totally for two weeks. Until he feels obligated to say again, 'Emma, you really have to face this.'"

So here was Weisberg at the end of 2015. Beaten down and distressed, running out of money, up against a reality she's not yet willing to accept. If only she can bring herself to collect that first failure badge. She'll be stronger, smarter, more resilient than ever before. Wear it proudly and she may even find it easier to get funding for her next venture.

Or so the expansive and trendy literature of failure would have her believe. But it's not that simple. There is a personal cost to failure, commensurate with the initial investment. Founders like Weisberg bring tons of passion to their startups. It's what gets them up off the couch in the first place, and what makes them stand out to potential backers. Everybody who ever met Weisberg has observed that quality in her. It's what the Kelley School's Shepherd sees as "the emotional investment necessary to achieve success." But here's what Shepherd also sees: Those who make that big upfront investment may not be able to learn from failure, or otherwise reap its abstract rewards, at least not right away. Because failure can take a severe toll at the back end.

Shepherd knows this from personal experience, having suffered with his whole family through the collapse of his father's construction business. The anxiety was crippling; the recovery process was long, arduous. He likens it in extreme cases to Elisabeth Kübler-Ross's five stages of grief--from denial through anger, bargaining, and depression, arriving finally at acceptance. "If you analyze it at the firm level, the region level, the country level, failure's just part of the process," Shepherd says. "We have to accept it, and if we do, that's going to be a good thing. But at the personal, individual level, at that period of time, it's bloody hard."

E. Tory Higgins, a prominent Columbia University psychologist who also teaches at Columbia Business School, goes a step further. He understands why investors may be attracted to entrepreneurs who can boast about their failures. He just thinks those investors could be making a big mistake by backing losers.

Higgins formulated what's known as regulatory focus theory. RFT divides the world into two sets of traits that define what we want and how we pursue our goals. The first, pro­motion focus, is all about growth and striving. It's the hunger, Higgins has written, for "advancement from the status quo to better states." Promotion focus fears standing still. Among its defining qualities are optimism, a preference for speed over accuracy (fail fast, anyone?), and an appetite for risk.

Then there's prevention focus. People inclined that way are more concerned with "safety, security, and the maintenance of the status quo against falling to worse states." Prevention focus fears failure. It's not optimistic, but realistic. Not rash, but careful. Unwilling to take big risks without first staking out a fallback position.

Venture capitalists--surprise, surprise--are heavily in the promotion camp. "They want to use their money to get to a better state, to make more money," says Higgins. When it comes to placing bets on entrepreneurs, he thinks VCs may be projecting--assigning as likely indicators of success precisely those qualities they see in themselves. Walk in there promising great things, telegraphing impatience, and yes, wearing your failure badge, and that's as good as knowing the secret handshake.

But here's the problem with keying too much on promotion, says Higgins: "It has nothing to do with the likelihood of success. Promotion people are overeager. What they really should have is a prevention part to themselves. Or a prevention partner. If you're an entrepreneur who is consistently successful, prevention has to be part of what you do. You have to have a plan B."

"We have to accept it, and if we do, that's going to be a good thing. But at the personal, individual level, at that period of time, it's bloody hard."

When I meet Weisberg at the Utopia, she's already deep into executing her plan B: Secure a job, make some money, preserve Blinkbuggy on life support, and hope for one more miracle. Axelrod has tried to discourage her. He's never known a founder who has pulled that off. "Look," he says, "I know you don't like what I'm telling you, but I'm just telling you I've never seen it happen, all right?"

Others are advising her to sell Blinkbuggy immediately, to take what she can get. Maybe even pay some people back. "She might feel like a failure," one of her anonymous investors tells me, "but statistically, she would be top tier. Selling the business and recovering the capital is a huge win. Not returning money to investors is a huge fail. And the risk of ultimate failure grows the longer she holds out."

Weisberg hears what they're saying. Nobody wants to look an investor in the eye and say, "I lost your money." But if that were all there was to failing, maybe Weisberg wouldn't be taking this so hard. Thing is, it's so much more. It's telling all the talented people you brought on board you can't pay them anymore. It's admitting to thousands of moms that you won't be keeping your promise to hold their most precious memories forever. ("I understand because I've been building my accounts for my children over the past two and a half years," she says. "There's no value you can put on that.") It's abandoning a years-long project that felt more like a calling, that took your talent, your heart, your best self, and then crushed you.

In a couple of weeks, Weisberg will get that job. In marketing, at someone else's startup. I'll call her then to ask about her first day back at work. She'll tell me she was sad at first. But then she started meeting people, talking to people, going to meetings. "And it switched," she'll say. "I felt, 'This is right, this is a good thing,' and that positive feeling made me feel positive all around."

Weisberg is tough. Always cheerful, every time we get together. But this afternoon at the Utopia? I believe those are tears in her eyes.

What 'Shark Tank' Host Kevin O'Leary Learned From a $2.5 Million Failure
From the July/August 2016 issue of Inc. magazine