Fail Better, Sell More: Five Entrepreneurs Who Made a Fortune Selling Their Own Disasters
The startup world has a complicated relationship with failure. On one hand, every pitch deck includes a slide about "learning from setbacks." On the other, actual public failure — the kind where the product bombs, the investors bail, and the press notices — is still treated like a communicable disease. Nobody wants to stand too close to it.
Except, it turns out, consumers. Consumers love a disaster. They love it with the same enthusiasm they bring to true crime podcasts and reality television train wrecks. And a handful of very smart, very unsentimental entrepreneurs have figured out how to weaponize that appetite.
Here are five people who stopped hiding their failures and started selling them.
1. The Energy Drink That Bragged About Tasting Terrible
In 2011, a small beverage startup in Austin launched what its founder, Derek Pulaski, genuinely believed would be the next Red Bull. It was caffeinated, vitamin-fortified, and aggressively marketed to the college market. It also tasted, by widespread consumer consensus, like someone had dissolved a multivitamin in flat ginger ale and left it in a warm car.
The initial run sold about 40% of its stock. The rest sat in a warehouse in Round Rock, Texas, accruing storage fees.
Pulaski's pivot was either genius or desperation — he's never been entirely clear which. He relabeled the remaining inventory "Dreadful" (tagline: We Know), redesigned the can to feature a grimacing cartoon face, and launched a social media campaign built entirely around negative reviews. He paid a local radio host to describe it as "the worst thing I've ever put in my body" on air. He sent cases to food bloggers with a note that read, "We're not asking you to like it. We're asking you to be honest."
Dreadful sold out in eleven days. A second run sold out in four. By 2013, it was stocked in 200 independent retailers across Texas, primarily purchased by college students who gave it as gag gifts and found, occasionally, that they'd developed a genuine affection for the taste. The brand eventually sold to a regional beverage distributor for a figure Pulaski describes only as "enough to make the warehouse fees feel like a rounding error."
2. The Cookbook That Celebrated Culinary Catastrophe
Jamila Osei spent three years developing a line of premium meal kits targeting the health-conscious urban professional. The branding was sleek. The ingredients were locally sourced. The instructions were, by the assessment of the food journalists she'd invited to a launch event, "catastrophically unclear."
Eight months after launch, with mounting losses and a customer return rate that defied actuarial logic, Osei shut down the meal kit company. Then she wrote a cookbook.
Dinner Is Ruined compiled the worst recipes from her failed line — dishes that consistently produced inedible results — alongside honest annotations explaining exactly why each one failed and what the experience of developing them felt like. It was part culinary memoir, part comedy, part genuine food science. A small press in Chicago took a chance on it.
The book sold 60,000 copies in its first year. It was featured in Bon Appétit. It spawned a YouTube series. Osei now runs a cooking school in Atlanta built around the philosophy that understanding failure is more instructive than replicating success — and charges premium rates for the privilege of learning from her mistakes.
3. The App Nobody Used That Became a Museum Exhibit
In 2015, a San Francisco developer named Tomas Eriksen launched a location-based social app called Nearbyish, which was designed to help strangers strike up conversations based on shared proximity. It found approximately 800 active users at its peak and was, by every conventional metric, a failure of notable proportions.
Eriksen's post-mortem was unusual. Instead of pivoting or quietly sunsetting the app, he archived every conversation that had ever taken place on Nearbyish and submitted the collection to a digital humanities project at UC Berkeley as a cultural artifact. He then wrote a widely-circulated essay titled "What 800 People Talked About When Nobody Was Watching," which detailed the surprisingly moving, frequently absurd, and occasionally profound exchanges that had occurred between strangers who'd downloaded a failing app.
The essay went viral. A gallery in Oakland exhibited printed transcripts of Nearbyish conversations as an art installation. A podcast about digital loneliness licensed the archive. Eriksen was invited to speak at SXSW — not about app development, but about what failed technology reveals about human connection. He has since built a consulting practice advising tech companies on user behavior, funded almost entirely by the afterlife of a product that 99.9% of the internet never knew existed.
4. The Startup Bankruptcy That Became a Bestselling Curriculum
When Rachel Ng's e-commerce startup filed for Chapter 7 bankruptcy in 2017, she owed $340,000 to creditors and had a business plan that, in hindsight, contained what she now calls "seventeen distinct and avoidable catastrophic errors."
She documented all seventeen in a self-published book called How to Lose $340,000 in Eighteen Months: A Practical Guide. She sold it for $27 on her personal website. She expected to sell a few hundred copies to people who found her story funny. She sold 12,000 copies in the first six months, primarily to MBA students, startup founders, and small business owners who found her forensic honesty about financial mismanagement more useful than any case study they'd encountered in school.
The book was eventually picked up by a business press, expanded with additional chapters, and is now used as a supplementary text in entrepreneurship courses at four American universities. Ng consults with early-stage startups on financial planning. Her primary credential, which she lists without irony on her website, is that she has made every mistake so her clients don't have to.
5. The Furniture Line That Sold Its Own Ugliness
Dave and Carla Whitmore launched a custom furniture business in Portland, Oregon, in 2016 with a design aesthetic they described as "industrial Scandinavian." Customers described it differently. Returns were high. Reviews mentioned words like "uncomfortable," "confusing," and, memorably, "aggressively beige."
Rather than redesign, the Whitmores leaned in. They rebranded as Objectively Ugly Furniture, updated their website with the most critical reviews they'd received (framed, literally, as endorsements), and started selling their pieces as "conversation starters for people who are tired of having the same conversation." They partnered with a Portland art collective that used their furniture in installations about consumer aesthetics. They started hosting "ugly furniture" pop-ups that drew crowds who came to laugh and frequently left having bought something.
Objectively Ugly now has a six-week production backlog and ships to thirty-two states. Their most popular piece is a chair that three separate reviewers described as looking like it was designed by someone who had never sat down.
The Pattern Behind the Pivots
These five stories don't share an industry, a demographic, or even a type of failure. What they share is a willingness to stop treating failure as something to overcome and start treating it as something to examine — and, eventually, to sell.
The market, it turns out, has an enormous appetite for honesty about how hard things actually are. In a culture saturated with highlight reels and success theater, a product that admits it's bad, a founder who documents every mistake, or a business built on the wreckage of a previous one carries a kind of credibility that no amount of polished branding can manufacture.
The lesson isn't that failure is secretly success. It's that failure, handled with enough self-awareness and a little bit of nerve, can become something people genuinely want to be part of.
Even if it tastes like a warm multivitamin dissolved in flat ginger ale.
