What happens when you have world class credentials, real traction, undeniable market size and the room still reduces you to a “brand”?

In this episode of The Capital Flex, I sit down with @Dr. Maria Uloko, a board certified urologist, sexual health expert and the founder and CEO of VULVAi, a digital health platform building AI-powered diagnostics, education and treatment pathways for vulvovaginal and pelvic pain.

Dr. Uloko is one of only seven urologists worldwide trained in comprehensive sexual medicine for all genders, and she’s using that expertise to rebuild a system that has ignored vulvar health for decades. In this conversation, we unpack what happens when deep clinical credibility collides with a venture ecosystem that isn’t designed to recognize it.

From being told she would make a “great Gwyneth Paltrow” after pitching a trillion-dollar healthcare opportunity, to watching men raise half a million dollars with emoji decks, Maria shares the unfiltered reality of fundraising as a Black woman founder building at the intersection of medicine, technology and social impact. 

We talk about pattern recognition, power, medical sexism and why women’s health cannot be built on top of broken systems. This episode is about conviction, discernment and choosing capital that aligns with the future you’re actually building.

Key Topics Discussed:

• Leaving academia to build VULVAi and why tech felt like the only viable path
• Being one of seven global experts and still not being believed
• The emoji deck story and what it reveals about venture bias
• How medical sexism shows up in fundraising rooms
• Why women’s health is a trillion-dollar opportunity still underestimated
• How VC pattern recognition excludes category creators
• The role of impact investing and non-dilutive capital in healthcare
• Trusting lived expertise as a strategy, not a risk
• Why investing in women creates ecosystem-level returns

My Reflection:

What stayed with me wasn’t just how absurd these stories are, it’s how predictable they are. What’s striking is how easily dismissal shows up in venture, even when the data, credentials and lived experience are undeniable.

This isn’t imposter syndrome, it’s a system design that’s broken. The real work is learning how the room operates, deciding when to engage and choosing partners who don’t need convincing to see what’s already there. Discernment is the skill.

This Week’s Challenge:

If you’re a founder:

• Audit who you’re taking fundraising advice from and whose experience they represent
• Ask whether the capital you’re pursuing supports incremental progress or real systemic change

If you’re an investor or ally:

• Notice when you’re asking experts to prove what they’ve lived for decades
• Practice trusting expertise that doesn’t fit familiar patterns

Links and Resources:
https://vulvai.co
https://www.instagram.com/vulvai.co/
https://vulvai.co/blog
https://www.linkedin.com/in/maria-uloko-826092166/

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 Business Solutions. 

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:

milocares.com

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 Business Solutions. 

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 Episode

• Building Hey Jane’s accessible telehealth model for abortion care
• Navigating vice clauses, LP conflicts, and SPVs in fundraising
• Raising “Roe round” capital without a traditional lead investor
• Gendered dynamics in venture and bias in women’s health investing
• Fundraising tips on screening investors and finding aligned angels

My 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 Challenge

Before 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/@heyjanehealth

https://www.facebook.com/heyjanehealth/

https://twitter.com/HeyJaneHealth

https://bsky.app/profile/heyjanehealth.bsky.social

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 Business Solutions. 

In this episode of The Capital Flex, I sit down with Somer Baburek, President and CEO of Hera Biotech, a women’s health company building AI-powered diagnostic tests and devices to transform how conditions like endometriosis are identified and treated. Somer and I talk candidly about what it really looks like to fundraise as a female founder in hard-science women’s health—beyond the polished narratives and into the uncomfortable, often infuriating, realities of venture.

We get into the dynamics of corporate VC, the importance of having a board that truly has your back, and the subtle (and not-so-subtle) bias that shows up in both male and female investors. Somer also shares why she believes the real opportunity in women’s health lies in serious life science and B2B models, not just direct-to-consumer period apps—and why knowing your financials inside and out is non-negotiable for any founder heading into a raise.

Key Topics Discussed in the Episode:

• Founding Hera Biotech and developing AI-powered diagnostics
• A corporate VC lowball offer and how her board backed her
• The “Elizabeth Holmes” question and investor bias in biotech
• Why many femtech funds overlook hard-science women’s health
• Somer’s key fundraising advice for female founders

My Reflection & Challenge

Listening back to this conversation, what stayed with me wasn’t just the absurdity of the stories — it was how predictable they were. The napkin valuation. The “I like you” framing. The decision to bypass the CEO and go straight to the men on the board. The Elizabeth Holmes question that somehow still finds oxygen in rooms full of “smart” people. None of this is rare. What is rare is watching a founder hold the line without contorting herself to make others comfortable. Somer didn’t just survive these moments, she learned how to read them faster, name them sooner, and move on without apologizing. The throughline here isn’t outrage. It’s discernment. 

Fundraising doesn’t just reveal who will fund your company. It reveals who will try to control it, diminish it, or test your tolerance for nonsense. The real work is recognizing which is which and trusting yourself enough to act on it.

This Week’s Challenge

Before your next fundraising conversation, write a one-page non-negotiables list.

Include:

• Minimum acceptable valuation logic
• Board behavior you will not tolerate
• Questions you will not answer
• Signals that mean “this is not the check we want”

Review it before every pitch. Your job isn’t to endure every room, it’s to choose the right ones.

Connect with Somer Baburek and Hera Biotech:

www.herabiotech.com 

https://www.linkedin.com/in/somerbaburek/ 

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 Business Solutions. 

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.

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 Business Solutions.