From Founder to Venture Partner: How Chief Co‑Founder Lindsay Kaplan Is Betting on “Weird” Consumer Startups

Lindsay Kaplan co-founded Chief, built one of the most talked-about communities in tech, and then left to go on a year of soul-searching (and like many founders, angel investing). Coming out of that walkabout was Lindsay joining up with our friends at Bullish as a Venture Partner. In her new role, she’s hunting for “weird” … Read more

Interview: Chieh Huang on Building the Bridge Between AI Job Destruction and Job Creation

Chieh Huang has seen disruption cycles before. As co-founder of Boxed (the bulk shopping app that went public via SPAC), he built a company that employed thousands of warehouse workers. Now he’s betting that AI will trigger the biggest workforce transition in a generation. And he just launched Pelgo to help people land on the … Read more

My Vibes On Vibe Coding

I spent an hour with vibe coding expert ​Saadiq Rodgers-King​ and now I feel like Superman. In the week since that crash course, I’ve shipped multiple internal tools tied to our CRM and email workflows. ​A year ago, these would have taken me weeks or never shipped at all.​ Observations so far: What kind of … Read more

Founder’s Feature (Electric)

This story starts on a Manhattan rooftop at the end of this past summer… This is a Sponsored Feature from Electric. I only write Sponsored Features where I have a genuine personal connection to the story and where there are real lessons for founders, funders, and operators. You can read our Sponsored Feature editorial guidelines … Read more

Venture5 2025 Recap

Thank you for the support this year, whether it was by reading our work, sharing it, or telling a friend about it. That’s why I thought it was important to show you what you contributed to building. So here’s how Venture5 did in 2025, by the numbers … along with some lessons learned! LinkedIn I … Read more

My Media x VC Thesis

I was at a holiday party on Thursday last week when I heard someone say that media is “the next big thing” in venture capital. Even though I run a media company focused entirely on venture capital … I’m skeptical. You see, the idea that VCs can use content to build an edge isn’t new. This is … Read more