Jesse Draper (Halogen Ventures) on Betting on Companies Early, Founder Red Flags, and Why Investing in Women Is NOT a Charity

Jesse Draper has heard it all: “nepo baby,” “charity fund,” “too niche”—and she turned every jab into fuel. After getting laughed out of rooms while raising her first fund, Jesse built Halogen Ventures into one of the earliest venture capital funds explicitly focused on backing female founders, now with 85+ portfolio companies and multiple unicorns. In this episode, Jesse breaks down how she actually evaluates startups when they’re early (and sometimes barely making their first dollar), the metrics she thinks founders overhype, and the green flags that make her lean in, like radical transparency and founders who are obsessed enough to “check QuickBooks” mid-question. She also tells the wild story of why she’ll never invest off Zoom again, how social media has changed consumer investing, and what the DEI rollback is starting to look like inside venture. Follow Sammi Cohen on Instagram Subscribe to the Social Currency newsletter Jesse’s epic interview with Elon MuskFollow Jesse’s work at Halogen Ventures Here’s what Sammi covers with Jesse 00:00 Jesse Draper’s Social Currency 00:50 Meet Jesse Draper 03:00 The Reality of Being Fourth Generation VC 06:13 The Valley Girl Show and the Elon Musk Interview 16:36 From Entertainment to Entrepreneurship 18:25 Getting Laughed Out of Pitches and Championing Female Founders 25:36 Crazy Pitch Stories 27:25 The Wild Con Artist Story 30:29 Never Invest Based on Zoom Meetings 34:03 The Viral “Investing In Women Is Not a F*cking Charity” Essay 37:16 Data That Investing in Women Works 38:09 What Founders Should Know About Conversations with VCs 41:43 Red Flags and Green Flags 46:44 How Social Media Has Changed VCs 53:00 Future of Equity in VC 59:12 Investing in Alabama 01:07:56 Social Currency Corner 01:09:57 How to Show Social Currency Some Love Learn more about your ad choices. Visit megaphone.fm/adchoices