Chip Sterling
Venture capitalist · The gilet. The pattern-matching. The term sheet.
Chip Sterling is the Sand Hill Road investor who funds whatever Chad has pivoted to this week. He has never given a straight answer to a question, but he has compared your company to a portfolio company in a way that sounded like an answer, and that is the service.
Chip wears the gilet indoors. He pattern-matches human beings. He is the reason Synthetica still has money, which makes him, technically, the villain.
The rest of the cast: Chad Vance · Wei Chen · Dev Kumar · Brooke · Sam. Or start at the latest strip.
Chip's strips
The Promotion
The board "promotes" Chad from CEO to Chairman and advisor
Product-Market Fit
Three VCs pass on Chad's pitch
Founding Relationship
Chip praises Chad's technical edge but says his only issue is that he loves founding teams who have known each other for years
The Gilet
Chip asks a fellow VC whether his gilet is wolf skin
Too Early
Chip passes on Chad because the company is too early
The Moat
A VC tells Chad his software has no moat, so two weeks later Chad builds a literal water moat around the office
Total Confidence
Chad has put the company's capital on a Polymarket bet that the USA will win the World Cup and swears he's certain
The Pass
A VC passes on Chad's round to put the money in the Anthropic IPO, admits he only took the meeting to look busy for his LPs, and cheerfully points out Chad won't be a founder much longer either