S1EP02 - Call Me a Charity One More Time with Kiki Freedman

In this episode, I sit down with Kiki Freedman, co-founder and CEO of Hey Jane, a telehealth platform delivering safe, discreet, and accessible abortion care and broader sexual and reproductive health services. Kiki shares how Hey Jane has grown to serving over 85,000 patients across 23 states, why macro moments like the fall of Roe have shaped their fundraising strategy, and how they’ve raised capital without a traditional lead investor by leaning into mission-aligned angels, SPVs, and syndicated rounds.We also get into the realities of building in a politicized area of healthcare, from navigating vice clauses and LP conflicts to hearing investors question why Hey Jane is a business and not a non-profit. Kiki talks candidly about gendered experiences in venture, why some conversations just aren’t worth the time, and how founders can protect their energy by qualifying investors early. She closes with practical advice on structuring your raise, using your time wisely, and finding the right angels plus how listeners can plug into Hey Jane’s Unwhisper Network and support the broader reproductive health mission.Topics Discussed in This EpisodeBuilding Hey Jane’s accessible telehealth model for abortion careNavigating vice clauses, LP conflicts, and SPVs in fundraisingRaising “Roe round” capital without a traditional lead investorGendered dynamics in venture and bias in women’s health investingFundraising tips on screening investors and finding aligned angelsMy Reflection & Challenge What stayed with me from this conversation is how intentionally Kiki chose not to contort her company to fit a system that wasn’t built for it. Instead of chasing a traditional lead or spending months educating misaligned investors, she protected her time and built a fundraising strategy that matched reality—syndicated rounds, SPVs, and capital raised in direct response to demand. That kind of clarity isn’t a shortcut. It’s discipline. And it’s a reminder that creativity in fundraising isn’t a compromise—it’s often the most strategic path forward. This Week’s ChallengeBefore your next investor conversation, write down three deal-breakers (LP conflicts, risk tolerance, mission alignment). Name them in the first meeting. Let misalignment surface early and move on faster. Connect with Kiki Freedman and Hey Jane:https://www.heyjane.com/https://www.linkedin.com/company/hey-jane/https://www.instagram.com/heyjanehealth/https://tiktok.com/@heyjanehealthhttps://www.facebook.com/heyjanehealth/https://twitter.com/HeyJaneHealthhttps://bsky.app/profile/heyjanehealth.bsky.socialIf you enjoyed this conversation, follow The Capital Flex, leave a rating, and share this episode with a founder who needs it.And if you’re looking for a more candid space to talk fundraising, power, and building inside systems not designed for you, stay close. The conversation continues.Production and Administration work completed by Smart Podcast Solutions and Elevate Business Solutions.