Side Hustle Graveyard: The Celebrity Business Ventures That Crashed So Hard They Left a Crater

There is a particular kind of hubris that only fame can produce. It's the moment when a person — talented, celebrated, surrounded by yes-people — looks at their Instagram following and thinks: I could also sell things. Not just one thing. Many things. Simultaneously. With a lifestyle brand aesthetic and a Goop-adjacent newsletter and maybe a docuseries about the journey of building the brand, which will air before the brand is actually built.

Sometimes this works. Rihanna's Fenty Beauty is a legitimate empire. Ryan Reynolds turned Aviation Gin into a masterclass in self-aware marketing and sold it for a reported $610 million. George Clooney's tequila exit made him richer than most of his movies did. These people correctly identified a lane, stayed in it, and let quality do the work.

This article is not about those people.

This article is about the other ones.

The Audacity-to-Quality Ratio: A Rubric

Before we begin the eulogy tour, it helps to establish a framework. Not all celebrity business failures are created equal. There is a spectrum — let's call it the Audacity-to-Quality Ratio — that measures how aggressively a celebrity believed in their venture versus how good the venture actually was. A high audacity score with a low quality score produces maximum carnage. Low audacity, low quality is just forgettable. High audacity, high quality is Fenty. We're here for the first category.

We're here for the scorched earth.

Gwyneth Paltrow and the Candle That Launched a Thousand Headlines

Goop is technically still alive, which makes it a survivor rather than a corpse, but it earns a place in this piece for the sheer audacity of its ongoing existence. Paltrow's lifestyle brand has been fined by the California Department of Public Health, mocked by doctors, dermatologists, and basically every scientist with a Twitter account, and has sold products with health claims so eyebrow-raising they prompted formal legal settlements.

And yet: Goop persists. It expanded. It launched a Netflix show. It sold a candle described as smelling like Paltrow's own anatomy for $75, which sold out immediately because we as a society made choices.

Goop's genius — and it is a twisted, chaotic genius — is that the controversy is the marketing. Every time a physician goes on television to explain why jade eggs are not medically advisable, Goop sells more jade eggs. This is not a business failure. This is a business model built entirely on the fuel of other people's outrage, and it is deeply, philosophically upsetting.

Audacity score: 11 out of 10. Quality score: debatable, legally speaking.

The Podcast Graveyard (Population: Everyone)

At some point between 2019 and 2022, a memo went out — apparently to every celebrity simultaneously — that they should start a podcast. Not because they had something to say. Not because they had expertise or a particular format in mind. But because podcasts were the thing, and being the thing was the point.

The resulting content landscape was extraordinary in its mediocrity. Actors interviewing other actors about the craft of acting. Musicians discussing the music industry with other musicians. Reality stars processing their reality television experience in real time, with their friends, for money. Some of these shows had enormous launch numbers — because a famous person's audience will show up once, out of loyalty and curiosity — and then fell off a cliff by episode four when listeners realized that fame does not automatically confer the ability to conduct an interesting interview.

The ones that quietly disappeared without announcement are too numerous to individually name. You know who you are. We know who you are. We just can't find the RSS feed anymore.

Kendall Jenner's Tequila and the Art of the Unapologetic Launch

In 2021, Kendall Jenner launched 818 Tequila. The name referenced her area code. The aesthetic was impeccable. The marketing was saturated and relentless. The problem was that tequila people — and tequila people are a specific, passionate, deeply opinionated group — immediately began raising questions about the brand's sourcing, its agave practices, and whether the product was meaningfully different from the generic spirits being repackaged under celebrity labels across the industry.

The other problem was a promotional video in which Jenner appeared to be harvesting agave herself, which the internet received approximately as well as you'd expect. The brand survived — it's still on shelves — but the launch became a case study in what happens when the aesthetic of authenticity isn't backed by the substance of it.

The lesson: tequila drinkers will fact-check you. They have time. They have strong opinions. And they have the internet.

The Cookbook Industrial Complex

Every celebrity has written a cookbook. This is not an exaggeration. Actors, musicians, athletes, influencers, the children of celebrities, and at least two Real Housewives have published cookbooks in the last decade. The majority of these books share certain qualities: beautiful photography, a personal essay in the introduction about the author's complicated relationship with food, and recipes that are either aggressively simple ("roast vegetables with olive oil and salt") or suspiciously specific ("my grandmother's Sardinian lentil stew, adapted for the modern kitchen").

Most of them are also quietly out of print within eighteen months. The celebrity cookbook is the literary equivalent of a gift shop impulse purchase — you grab it at the register, display it on your counter for a few weeks, and then it migrates to the shelf where books go to be looked at rather than opened.

The genre peaked and collapsed so quickly that publishers are now considerably more selective, which means the era of the celebrity cookbook is not quite over but is definitely entering its hospice phase.

The Quietly Deleted Evidence

The true measure of a failed celebrity venture is not the bankruptcy filing or the scathing review. It's the quiet deletion. The Instagram posts that disappear. The website that returns a 404 error. The YouTube channel where the brand launch video used to live, now replaced by a void.

Celebrities are exceptionally good at memory-holing their failures, and the internet is imperfect enough at preservation that many of them get away with it. The skincare line that lasted eight months. The app that launched to press coverage and died to silence. The wine label with the famous person's face on it that you can still occasionally find at TJ Maxx for $6.99, which is the true tombstone of any celebrity business venture.

We see you. We remember. We are not naming names only because the lawyers exist.

What It All Actually Means

The celebrity side hustle industrial complex tells us something real about the nature of fame in the attention economy. When your name is the asset, there's enormous pressure — from managers, from investors, from the culture itself — to monetize that asset in every possible direction before the window closes. The diversification isn't always greed. Sometimes it's fear. Fame is finite and everyone in it knows it.

The tragedy isn't that they tried. It's that so many of them tried without the infrastructure, the patience, or the genuine product quality to back the name up. Fame gets you the launch. It does not get you the second year.

The good news is that failure in this particular arena is rarely fatal. The celebrity usually survives. The candle brand, less so. The candle brand almost never makes it.