The Capital Flex Podcast

Naseem Sayani
  • 5.0 (6)
  • INVESTING

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.

Episodes

  1. S1EP11 - We Need More Magical Thinking with Alison Greenberg

    1D AGO

    S1EP11 - We Need More Magical Thinking with Alison Greenberg

    Every founder has encountered that “maybe investor”, the one who needs weeks to decide, asks endless questions, and quietly burns your timeline. In this episode of The Capital Flex, I sit down with Alison Greenberg, former CEO and co-founder of Ruth Health, and now Senior Director of Growth and Partnerships at Ember Health in New York City. Alison and I talk candidly about what it looks like to raise as a female founder in the early days of women’s health. We unpack her experience raising for Ruth Health, the pivots, the long pre-seed grind, and what shifted when Alison entered Y Combinator. She shares a story about an investor who stalled for months, demanded endless proof, and then erupted when the round closed – with seemingly no awareness of their own analysis paralysis.  We also dive into Alison’s observations about how men negotiate exits and pricing, how women can strengthen the same muscle, and why simply showing up is half of the game. Key Takeaways: Why women’s health founders often start without clean compsWhat she learned about long cycles and how to spot a ‘no’ fasterWhat changed after her Y Combinator experience, why network effects matter and the reunion story you will not forgetWhy there are critically important negotiation lessons women rarely get taughtWhy “showing up” is a necessary strategy, as important as the follow-up, the ask, and the repetitionMy Reflection & Challenge: Listening back to this conversation, what stayed with me was the timeline tax. The months of energy founders donate to “maybe,” the emotional energy spent proving what should be obvious, and the way women are still expected to stay gracious while someone else burns the clock. Alison’s story is not just about one investor, it is about the pattern. What also landed was the negotiation contrast. Men are often willing to name a number that feels slightly unreal, then let the room negotiate them down. Women tend to start with the most defensible number, then hope the ceiling rises. The lesson is to stop low-balling ourselves out of the gate. This Week’s Challenge: Before your next capital conversation, write a one-page “Move Faster” sheet. Include: Your close date and what happens if someone misses itYour minimum viable “yes” signalsThe first number you will anchor with and why you can defend itYour max number of meetings before you decide it is a ‘no’The phrases you will use to exit cleanly, quickly, and without guiltKeep it beside you during every pitch, your time is part of your valuation. Links and Resources: https://emberhealth.co/team/alison-greenberg/ https://www.linkedin.com/in/greenbergalison/ https://x.com/alis0nlaura/ https://emberhealth.co/ Email: allisonwith1l@emberhealth.co 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.

    39 min
  2. S1EP10 - Why Mess with My Maternity Leave with Sona Shah

    MAR 25

    S1EP10 - Why Mess with My Maternity Leave with Sona Shah

    What happens when the round is “closed” on paper, but your runway is still waiting on a wire? In this episode of The Capital Flex, I sit down with Sona Shah, CEO and co-founder of Neopenda, a med tech company building wearable vital sign monitors for newborns in hospitals across Eastern Africa. Sona’s path began in chemical engineering, took her to Western Kenya as a teacher, and ultimately led her to biomedical engineering at Columbia. It was there that Neopenda was born from a stark realization: most traditional medical equipment is not designed for the majority of the world’s population. Sona shares the unfiltered reality of fundraising when you are building hardware in a regulated category for emerging markets, and what it looks like when a “trusted” investor commitment quietly turns into months of delay. She shares the moment she realized, just days before giving birth, that a signed check was never coming, and how that realization unraveled her timeline, her plans, and her peace. We also go beyond the mechanics of capital and into the power dynamics that surface in the room. The blurred boundaries. The subtle tests. The decisions founders have to make when professionalism crosses the line. Sona names what happened, how she responded, and why she handled it with precision instead of panic. This conversation is about persistence, safeguards, and building a company that proves profitability and impact can scale together. Key Takeaways: Why regulated hardware fundraising requires different expectationsHow a “closed” round can still become a cash crisisWhat to change in your closing process so funds actually arriveHow to respond when investor behavior crosses professional linesWhy conversation is not enough and action is the only metricScaling Neopenda from thousands of patients to millionsMy Reflection & Challenge: Listening back, what stayed with me was Sona’s clarity. Fundraising is not only about conviction, it is about systems. The system you use to close and protect your time matters as well as how to decide who earns access to you. When people tell women to be “less intense,” what they are really saying is, leave gaps they can exploit. Sona’s story is the reminder that being meticulous is not a personality trait, it is a strategy. This Week’s Challenge: Before your next investor meeting, write your closing rules in advance. Ask yourself: Do I have a same-day wire expectation tied to signature?What are my non-negotiables if funds are delayed?Am I treating this like a relationship or a transaction?Who has earned the right to stay close when things get hard?Links and Resources: www.neopenda.com https://www.linkedin.com/company/neopenda/ https://www.instagram.com/neopendahealth/ https://www.facebook.com/Neopenda https://www.linkedin.com/in/sonarshah/ 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.

    35 min
  3. S1EP09 - Sniffing Out Predatory Terms with Cecilia Tse

    MAR 18

    S1EP09 - Sniffing Out Predatory Terms with Cecilia Tse

    What happens when the hardest part of fundraising is not the pitch, but the structure behind the check? In this episode of The Capital Flex, I sit down with Cecilia Tse, CEO and co-founder of hey freya, a science-backed women’s health company helping women understand stress, biology, and decision-making through data, systems, and real-world usability. Cecilia is a former management consultant and wellbeing strategy leader at PwC who navigated her own IVF journey and is now one of the most analytically fluent founders operating in health and venture today. We talk about what fundraising looks like when you understand venture economics but still find yourself navigating a system driven by relationships, pattern recognition, and inefficiency. Cecilia names her fundraising experience in three words: ongoing, inefficient, and connection-driven and explains why those realities are not contradictions, but features of the system itself. Cecilia walks through a fast-moving term sheet that looked progressive on the surface, but quietly shifted risk entirely onto the founder. We talk about why speed is often used to limit scrutiny, how certain structures protect funds at the expense of companies, and why fluency matters more than optimism. This conversation is about discernment, power, and learning to read what is being offered before capital reshapes the company. Key Takeaways: Building hey freya while navigating her own IVF journey and fundraising Why founders are always fundraising even when no capital is movingThe inefficiency baked into venture capital matchingRelationship-driven decision making and its hidden tradeoffsHow fast term sheets can mask misaligned incentivesUnderstanding where risk truly lives in early-stage dealsWhy fluency in structures matters more than speedMy Reflection & Challenge: Listening back to this conversation, what stayed with me was how familiar Cecilia’s story felt. The confidence of the offer. The polish of the language. The pressure to move quickly. None of it was overtly wrong. That is what makes it dangerous. Fundraising does not just test your pitch, it tests your ability to see incentives clearly while someone else controls the pace. The founders who last are not the ones who raise the fastest, they are the ones who understand who a deal is designed to protect. Cecilia did not say no because the terms were confusing, she said no because she understood them. This Week’s Challenge: Before your next fundraising conversation, run a structure check. Ask yourself: Who is protected if things go sideways?Where does the risk sit?What assumptions are being made about my tolerance?Is speed being used to replace alignment?Remember, you are not here to take every check, you are here to build something that lasts. Links and Resources: https://www.getheyfreya.com/ https://www.instagram.com/getheyfreya/ https://www.linkedin.com/company/heyfreya/ https://www.linkedin.com/in/cecilia-tse/ 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.

    37 min
  4. S1EP08 - How's That for Masculine Energy with Jenni Ogden

    MAR 11

    S1EP08 - How's That for Masculine Energy with Jenni Ogden

    What happens when your company is strong, your tech is real, and the only thing “missing” is a man in the room? In this episode of The Capital Flex, I sit down with Jenni Ogden, founder of Eye Q Productions, a creative producer and immersive tech operator building at the intersection of spatial computing, AR, VR and live experience. Jenni is building a new platform that rewards activism through gaming, starting with eco-focused missions designed to turn awareness into real participation. Jenni shares a fundraising moment that still floors me, an investor told her the project was fully fundable – and then asked if she had a “masculine partner.” When she clarified the company was women-owned and women-led, he insisted she could not pitch to his fund as the CEO. She would need a male partner to present instead. We unpack why that one comment is not just a bad interaction, it is a blueprint for how the relationship would go after the check. We talk about the hidden cost of misaligned money, why founders must evaluate investors like long-term collaborators, and how early investor behavior is the most honest diligence you will ever get. We also get into the way women are socialized to lead with a story about mission, while men often lead with numbers, and why organizing your pitch money-first is not selling out, but a necessary strategy. Jenni closes with a simple filter that every founder needs: the lifeboat test. If you would not want them on your lifeboat when things get hard, do not take their money when things feel urgent. Key Takeaways: What “masculine partner” really signals in investor conversationsWhy investor behavior is data, not noiseHow misaligned money becomes a long-term drag on leadershipLeading with numbers first, then mission, in money-first roomsThe lifeboat test every founder should use before accepting capitalMy Reflection & Challenge: This conversation stayed with me because it shows how clearly the system tells on itself. Jenni did not need more traction. She did not need a different deck. She needed a room that was willing to see her as the CEO. The wrong capital does not just fund the company, it tries to rearrange who leads it. Your job is not to earn your place in every room. Your job is to notice which rooms don’t require you to shrink in order to play. This Week’s Challenge: Before your next investor meeting, write a one-page non-negotiables list: What you will not change to be “more fundable”What behavior signals misalignment immediatelyThe sentence you will use to end a meeting calmlyThe lifeboat test: would I want this person beside me long term?Capital is not just money. It is a relationship. Links and Resources: https://eyeqproductions.com https://www.linkedin.com/in/jenniogden/ https://www.instagram.com/eyeqproductions/ https://www.youtube.com/channel/UCqP2u4gES4g0wK8CdnPjfJA https://www.facebook.com/EyeQProductions/ h 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.

    21 min
  5. S1EP07 - Bias Isn't Personal with Annie Brown

    MAR 4

    S1EP07 - Bias Isn't Personal with Annie Brown

    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 modelHow vice clauses and conservative LPs quietly restrict what gets fundedThe double bind for women building deep technical infrastructureHow to use “reflection questions” to disarm biased investor commentsWhy trusting your gut is data and not emotionWhy AI-based tools for VC sourcing and diligence risk reinforcing existing biasMy 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: What support you actually need from capitalWhat behavior would be a dealbreaker pre-check and post-checkOne sentence you’ll use to calmly redirect biased commentaryCapital 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 Virtual Business Solutions.

    45 min
  6. S1EP06 - Find the Excitement with Mical Jeanlys-White

    FEB 25

    S1EP06 - Find the Excitement with Mical Jeanlys-White

    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 raiseWhy brokered introductions accelerate trust and reduce frictionHow to read investor chemistry quickly and stop over-investing in the wrong roomsHow bias shapes the way diverse founders get framed, even when it is nowhere in the deckWhy writing your own investment memo reframes diligenceWhy building a consumer brand is a capital strategy, not a luxuryMy 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 Virtual Business Solutions.

    41 min
  7. S1EP05 - Let's Not Be Curled Up on the Floor with Kaitlin Christine

    FEB 18

    S1EP05 - Let's Not Be Curled Up on the Floor with Kaitlin Christine

    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 cureThe emotional reality of fundraising and the identity crisis that comes with repeated rejectionWhy women’s health founders lose time educating instead of pitchingThe diligence double standard facing technical women in venture rooms, and how to handle being questioned by investors with less expertiseHow to recognize unprepared investors and protect your timeHow to begin controlling the power dynamic instead of absorbing itThe truth about working with some female-led funds and why backchannel diligence mattersWhy a strong founder community is a survival tool, not a bonusMy 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 convictionNotice which rooms drain you and which ones come preparedBuild a trusted circle of founders and at least one investor who will review term sheets with youIf you’re an investor or ally: Notice when lived expertise is being treated as anecdotal instead of authoritativeAsk whether your questions are advancing understanding or reinforcing biasCome prepared before asking founders to prove the basicsLinks 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 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.

    39 min
  8. S1EP04 - Who You Take Advice From is Critical with Dr. Maria Uloko

    FEB 11

    S1EP04 - Who You Take Advice From is Critical with Dr. Maria Uloko

    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 pathBeing one of seven global experts and still not being believedThe emoji deck story and what it reveals about venture biasHow medical sexism shows up in fundraising roomsWhy women’s health is a trillion-dollar opportunity still underestimatedHow VC pattern recognition excludes category creatorsThe role of impact investing and non-dilutive capital in healthcareTrusting lived expertise as a strategy, not a riskWhy investing in women creates ecosystem-level returnsMy 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 representAsk whether the capital you’re pursuing supports incremental progress or real systemic changeIf you’re an investor or ally: Notice when you’re asking experts to prove what they’ve lived for decadesPractice trusting expertise that doesn’t fit familiar patternsLinks 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 Virtual Business Solutions.

    39 min
  9. S1EP03 - Listening to Your Gut with Lisa Hillyard

    FEB 4

    S1EP03 - Listening to Your Gut with Lisa Hillyard

    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 Virtual Business Solutions.

    42 min
  10. S1EP02 - Call Me a Charity One More Time with Kiki Freedman

    JAN 28

    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 Episode Building 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 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 Virtual Business Solutions.

    23 min
  11. S1EP01 - Don't Elizabeth Holmes Me with Somer Baburek

    JAN 21

    S1EP01 - Don't Elizabeth Holmes Me with Somer Baburek

    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 diagnosticsA corporate VC lowball offer and how her board backed herThe “Elizabeth Holmes” question and investor bias in biotechWhy many femtech funds overlook hard-science women’s healthSomer’s key fundraising advice for female foundersMy 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 logicBoard behavior you will not tolerateQuestions you will not answerSignals 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 Virtual Business Solutions.

    42 min

  12. TRAILER

    Coming Soon...The Capital Flex!

    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 Virtual Business Solutions.

    6 min

Trailer

Ratings & Reviews

5
out of 5
6 Ratings

About

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.

Information

  • Creator
    Naseem Sayani
  • Years Active
    2025 - 2026
  • Episodes
    12
  • Rating
    Explicit
  • Copyright
    © 2026 The Capital Flex Podcast
  • Show Website
    The Capital Flex Podcast

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