“Shit I’m Fucked” Live Events
The Story
Hampton runs a live event format where 10 entrepreneurs tell 5-minute stories of their worst business failures to an audience of 100 founders. The format originated from a Hampton Slack channel.
A NYC event featured someone who raised $100M and blew it in 2 years, a $30M/year company brought down by a lawsuit, and someone with 5 sandwich franchises who went bankrupt.
Sam describes it as “very cathartic to laugh at our miseries and feel less alone.” Plans to make it recurring.
Lesson for Creators
Failure content outperforms success content because it creates connection. Success stories inspire, but failure stories bond. People don’t pay $9,500/year to hear how great everyone is. They pay to hear someone say “I raised $100M and lost it all” and realize they’re not alone in struggling. If you’re building community, make space for vulnerability, not just victories.
Related
- Founder Loneliness - Hampton’s Origin Story — The broader loneliness problem that led Sam to create Hampton and this vulnerability-first event format
- Sydney - The Dog Who Changed His Life — Sam’s most emotional public writing proved that vulnerable content connects far deeper than business advice
- Self-Worth = Net Worth - The Vulnerable Moment — Sam’s own admission of the psychological cost of ambition, the kind of honesty these events are built around