Not a startup. No bankruptcy or anything. Wife & I liked this company Goth Gift Baskets that used to advertise in Gothic Beauty magazine. One issue had an ad saying they were selling the business. We bought the name, website, inventory, and customer list for around $5000, with the intent of starting a side business & maybe growing it into something larger. We expected higher-quality merchandise, but ended up with boxes of plastic spiders and cheap closeout Halloween jewelry. The boxes were piled up in our spare bedroom and were soon joined by boxes of higher-end merchandise so our baskets were more appealing.
We over-estimated the appeal of "goth" in the mid-2000s. There was still a good turnout at goth events in Chicago, but it was mostly adults who liked to dress up on the weekends for old-time's sake, but didn't identify as goths in everyday life anymore. We paid for tables at concerts, hearse shows, and fan conventions, and usually didn't make enough to cover the table. At least the music was good. At one point we pulled up the Seattle Goth site hoping to do a sponsorship deal with them, and their home page was just a picture of Fonzie on waterskis.
There was still a decent-sized market of younger goths & "emos", but they didn't have the money for a $25 gift basket of jewelry, incense, candles, and such…and THEN shipping on top of that. We were told to offer something closer to $10 shipped, but that barely covered the cost of an empty basket, shipping materials, and postage with a tiny profit.
Twilight was pretty big, but our vampires didn't sparkle. We put together a Browncoat basket with a complete set of Firefly action figures and assorted other stuff…even had custom marketing materials made to distribute at fan conventions for it. Didn't sell a single one.
Magazine advertising was expensive, and resulted in zero orders. Emailing our customer list a 20% discount code every couple months resulted in 2 orders in three years. We were flooded with emails from events & meetups wanting us to donate baskets for raffle prizes, which we could at least write-off on our taxes & get some publicity for. No sales ever came of these sponsorship deals, but we did get some sweet thank-you letters.
The last year we were in business, we were hit with a $200 chargeback. We asked Paypal if they could validate the address or something on that big of an order, and they said there was nothing they could do. We took the risk, and lost the money, merchandise, and shipping. That one incident cancelled out our entire profit for the year.
We donated all the remaining merchandise to charity & took a write-off just so we could get our spare bedroom back (it became my "man cave"/computer museum). Our time is better spent volunteering if we're not going to make any money anyway.
Again, no huge crisis, no health problems. But, a lot of extra stress, a couple thousand bucks wasted on top of what we paid for the company, and an entire room our our house tied up for 3 years and nothing to show for it.
Edit: Oh yeah, let's not forget the month I got a bill from my hosting company for extra bandwidth because a picture of me from the site ranked high for "goth" in Google Images and people were hot-linking it in forum posts all over the place going "goths are so stupid. look at this guy he thinks he's spooky ooooh".