The most disappointing YC-backed product I tried was Stypi.
I teach community college and sometimes I wonder about the thought processes behind some of my students' papers. Paul Graham linked an essay he wrote in Stypi, where you could watch him write it in real time. This was clearly the greatest computer-assisted tool for teaching writing ever, and I immediately incorporated Stypi into one of my writing assignments. I wanted to know how much my students proofread, how they structured essays, and what they struggled with as they wrote. I was so excited about it that I wrote the entire assignment in Stypi and linked my students to the replay in case they were interested.
It was a disaster. So many students lost essays in browser crashes or were flat out unable to use the software. I ultimately had to apologize to my class, give everyone an extension, and cut Stypi out of the project.
Apparently they were acquired though, so I guess they made someone happy.
> Fortunately, my cofounder and I were lucky enough to have had access to several other acquired founders who helped us ultimately navigate our first multimillion-dollar exit for a company barely a year old.
> DISCLAIMER: Every startup and founder group is unique so the data provided here may not apply in all cases. In particular, it is skewed towards < $25m acquisitions made by much larger companies.
access to several other acquired founders who helped us ultimately navigate
That's founder code for "we actually failed, but we know rich people, so our failure is really our success—suck it, everybody else who fails without millionaire friend safety nets."
You should check HomeJoy. They were a cleaning company (they subcontracted cleaners) that went through YC, had a huge growth and raised about $40M, but went on to fail. Look for them in HN search, it has been discussed a lot.
Exactly :) But that is why I wouldn't put it on the list of a "Most promising startup that failed". To me a promising startup that failed would be someone who invented a nanobot to go scrub cancer from your body that ended up killing people and going bankrupt. Someone that tried really hard for a really cool idea that failed.. not an app for house cleaning.
One simple way to evaluate this would be to look at press attention.
I did a quick check using Mattermark data of which YC companies got the most news since 2013 that are not still alive. It yielded (num articles / startup):
67 Homejoy
13 Tipjoy
13 Buttercoin
6 Tutorspree
Tipjoy's founder started another company, got into YC again, got funded again, and got lots of press again. A lot of that press mentions the founder, and names his previous startups, including Tipjoy.
I teach community college and sometimes I wonder about the thought processes behind some of my students' papers. Paul Graham linked an essay he wrote in Stypi, where you could watch him write it in real time. This was clearly the greatest computer-assisted tool for teaching writing ever, and I immediately incorporated Stypi into one of my writing assignments. I wanted to know how much my students proofread, how they structured essays, and what they struggled with as they wrote. I was so excited about it that I wrote the entire assignment in Stypi and linked my students to the replay in case they were interested.
It was a disaster. So many students lost essays in browser crashes or were flat out unable to use the software. I ultimately had to apologize to my class, give everyone an extension, and cut Stypi out of the project.
Apparently they were acquired though, so I guess they made someone happy.