The Capital Flex Podcast

What happens when your technology is solid, your traction is real, and the problem is not your company, but the system deciding whether to trust you?

In this episode of The Capital Flex, I sit down with Annie Brown, Founder and CEO of Reliabl, an AI infrastructure company helping companies improve accuracy and reduce bias in machine learning by fixing what most people ignore: the data labeling layer. Annie is a bias researcher, former UC San Diego AI scholar, and repeat founder whose work has been featured in Forbes and Fast Company.

Annie has built and scaled in public, from founding a creative platform for women and LGBTQIA+ creators to growing Reliabl to $600K ARR in 10 months. She shares what it felt like to raise for an LGBTQIA+ focused product, then raise again for an AI infrastructure product, only to get stuck in the middle, where highly technical funds question the founder and underrepresented funds struggle with technical diligence.

Together, we unpack the uncomfortable realities of raising capital at the intersection of deep tech, identity, and pattern recognition.

This conversation covers vice clauses, LP pressure, technical diligence gaps and why women founders are often forced to navigate both credibility and capital at the same time.

Key Takeaways:

• Why bias in AI starts at the data labeling layer, not just in the language model
• How vice clauses and conservative LPs quietly restrict what gets funded
• The double bind for women building deep technical infrastructure
• How to use “reflection questions” to disarm biased investor comments
• Why trusting your gut is data and not emotion
• Why AI-based tools for VC sourcing and diligence risk reinforcing existing bias

My Reflection & Challenge:
What struck me most in this conversation is how often women founders are asked to contort themselves or strip out the very value proposition of their business just to be considered fundable. Annie’s story is not about traction or capability, but about structural misalignment between belief, trust, and technical understanding. 

Too often, founders are told to edit themselves instead of being evaluated on the business, and scarcity makes bad opportunities look like lifelines. Your job is not to survive every room, it is to choose the ones that can fund you without rewriting you.

This Week’s Challenge:
Pay attention to the feeling in your body during meetings. If something feels off, don’t override it with scarcity thinking.

Before your next investor conversation, write down:

1. What support you actually need from capital
2. What behavior would be a dealbreaker pre-check and post-check
3. One sentence you’ll use to calmly redirect biased commentary

Capital is not just money, it’s a long-term relationship.

Links and Resources:
http://reliabl.ai
http:/linkedin.com/in/andreafrancesb

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. 

What happens when you stop trying to convince investors and start qualifying them instead?

In this episode of The Capital Flex, I sit down with Mical Jeanlys-White, CEO and founder of WealthMore, an AI-native wealth tech platform built to bring expert financial strategy to everyday investors who traditional wealth management overlooks. With more than 20 years in financial services, including a decade at JPMorgan Chase building category-defining products, Mical is now applying her institutional experience to a new model: an AI financial coach paired with human advisors, no account minimum and a flat fee structure designed for the upwardly mobile professional building real wealth.

We unpack what fundraising feels like when rooms are loaded with bias and pattern recognition. Mical shares the principle guiding her raise, “find the excitement”, and why she’s not looking for polite interest or a “circle back,” she wants real momentum. We talk about writing your own investment memo, reading body language as a signal and why building a consumer brand is not marketing fluff, but a capital strategy when you are operating without a champagne budget.

Key Topics Discussed:

• What “find the excitement” actually looks like in a raise
• Why brokered introductions accelerate trust and reduce friction
• How to read investor chemistry quickly and stop over-investing in the wrong rooms
• How bias shapes the way diverse founders get framed, even when it is nowhere in the deck
• Why writing your own investment memo reframes diligence
• Why building a consumer brand is a capital strategy, not a luxury

My Reflection:
What stayed with me wasn’t just the strategy, it was the discipline. Mical does not beg rooms to understand her. She does not over-explain to earn validation. She reads the room, names the signal and moves on.

Too many founders confuse effort with progress. We believe that if we refine the slide or explain it one more time, the investor will finally get there. Meanwhile, the right investor is already leaning in. The right customer is already waiting. The right momentum is already available.

Capital does not just fund your company. It shapes your nervous system. And if you are spending your most valuable resource, your attention, on people who are not excited, you are not fundraising. Discernment is the skill.

This Week’s Challenge:
If you’re a founder:

Before your next investor meeting, create a “find the excitement” filter. Write down three signals that mean real momentum. List three disqualifiers you will not rationalize. Draft one sentence you will use to close the loop when the excitement is not there.

If you’re an investor or ally:

Notice when interest is vague and diligence is slow. Ask yourself whether you are leaning in with conviction or staying in polite observation mode. Fundraising is not about convincing. It is about qualifying.

Links and Resources:
WealthMore: https://wealthmore.com/
Mical on LinkedIn: https://www.linkedin.com/in/mical-jeanlys-white-9126366/

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. 

What happens when you are building a life-saving women’s health company and most of the pitch is spent convincing investors the problem is real?

In this episode of The Capital Flex, I sit down with Kaitlin Christine, breast cancer survivor, ovarian cancer pre-viver and the founder and CEO of Gabbi, a digital health platform helping women understand their breast cancer risk and access early detection care faster.

Kaitlin built Gabbi after losing her mother to a delayed breast cancer diagnosis and then experiencing her own delay shortly after. What began as a deeply personal need has become a category-defining women’s health company partnering with health systems, employers and providers across the country. But the path to building it has required far more than a strong product and a massive market.

In this conversation, we unpack what it feels like to fundraise in women’s health. From hearing “no” more than 70 times, to spending 25 minutes of a pitch teaching biology and five minutes talking about the business, Kaitlin shares the emotional, psychological and strategic toll of raising capital inside systems not built to understand women’s bodies or women founders.

We talk about diligence double standards, technical female leaders being interrogated by underqualified skeptics, and how founders can start reclaiming power in rooms where credibility is routinely questioned.

Key Takeaways:

• Building Gabbi from lived experience and why early detection is the real cure
• The emotional reality of fundraising and the identity crisis that comes with repeated rejection
• Why women’s health founders lose time educating instead of pitching
• The diligence double standard facing technical women in venture rooms, and how to handle being questioned by investors with less expertise
• How to recognize unprepared investors and protect your time
• How to begin controlling the power dynamic instead of absorbing it
• The truth about working with some female-led funds and why backchannel diligence matters
• Why a strong founder community is a survival tool, not a bonus

My Reflection & Challenge:
What stayed with me wasn’t just how exhausting these stories are, it’s how familiar they sound. Women’s health founders are not failing to communicate value. They are operating inside a system that requires them to prove the problem before they are allowed to pitch the solution.

This isn’t imposter syndrome. It’s structural friction. The work is learning how the room operates, deciding when to educate and when to disengage and choosing capital partners who don’t need convincing to see what’s already obvious. 

If you’re a founder:

• Pay attention to how much of your pitch is spent educating versus building conviction
• Notice which rooms drain you and which ones come prepared
• Build a trusted circle of founders and at least one investor who will review term sheets with you

If you’re an investor or ally:

• Notice when lived expertise is being treated as anecdotal instead of authoritative
• Ask whether your questions are advancing understanding or reinforcing bias
• Come prepared before asking founders to prove the basics

Links and Resources

• https://www.gabbi.com/

If you enjoyed this conversation, follow @The Capital Flex, leave a rating and share this episode with a founder who is raising inside systems not designed for her.

And if you’re looking for a more honest conversation about capital, power and what really happens in the room, stay close. The conversation continues.

Production and Administration work completed by Smart Podcast Solutions and<&a

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. 

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.