The Capital Flex Podcast
We’re codifying the capital playbook—because no founder should have to learn the hard way.
Hosted by Naseem Sayani, VC and unapologetic truth-teller, The Capital Flex unpacks what really happens when female founders raise money inside systems not built for them. From bias in the room to predatory term sheets, these are the stories we usually hear in DMs not headlines.
Each episode offers unfiltered insight, real strategies, and a new playbook where we write the rules. Because the system won’t fix itself. But we will.
The Capital Flex Podcast
S1EP03 - Listening to Your Gut with Lisa Hillyard
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
MILO Human Care is Lisa Hillyard’s answer to a CPG industry built on overconsumption and late-stage capitalism. Drawing on her years in adtech and executive leadership, she’s rebuilding the category through regenerative values — starting with skincare and ultimately aiming to become a venture builder that can go toe-to-toe with today’s beauty giants. Alongside MILO, Lisa is a newly published author of On Behalf Of, a book on corporate dynamics told through the lens of the executive assistant, questioning who we choose as leaders and why.
In this conversation, Lisa is brutally honest about a fundraising journey she describes as disheartening, illuminating, and ultimately empowering — from a “gender-lens” investor who blurred business and boundary, to VCs who were happy to monetize her but not back her. What emerges is a roadmap for founders who want to protect their integrity, trust their instincts, and build outside the traditional VC playbook.
We dig into overconsumption in beauty, predatory “gender-lens” capital, trauma responses in fundraising, and what it means to walk away from misaligned VC money.
Key Takeaways
- Overconsumption drives late-stage capitalism. MILO offers a regenerative alternative.
- Expect a power dynamic in every VC meeting; hold your center and trust your expertise.
- Separate useful critique from misalignment; their thesis isn’t your truth.
- Recognize freeze/fawn responses so you stop blaming yourself for survival instincts.
- Catch red flags when “gender-lens” investors blur boundaries and can’t write real checks.
- Sometimes the aligned move is opting out of traditional VC to protect your model.
My Reflection & Challenge
This conversation with Lisa Hillyard is a stark reminder that not all capital is neutral and not all “gender lens” investing is safe, ethical, or real. What struck me most was how quickly professional boundaries blurred, how often red flags were disguised as normal business behavior, and how deeply conditioned many women are to tolerate it just to keep momentum alive. Lisa’s story isn’t about one bad actor—it’s about patterns, power dynamics, and a system that still asks women to absorb harm quietly in exchange for access. Her clarity came not from winning VC approval, but from reclaiming her own authority and deciding that certain money simply isn’t worth the cost.
This Week’s Challenge
Before your next investor meeting, decide your exit criteria—not just for the deal, but for the behavior. If your body flags discomfort, confusion, or boundary-crossing, treat that as real data. You’re allowed to walk away without overexplaining. Protecting yourself is protecting the company.
Connect with Lisa Hillyard:
https://www.instagram.com/milomultifunctional/
https://www.tiktok.com/@milomultifunctional
https://www.linkedin.com/in/lisahillyard/
If 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 Virtual Business Solutions.
.png){kind=avatar}