The Capital Flex Podcast

S2EP3: Next Time I'll Leave the Room with Dr. Somi Javaid

After two decades in practice, keeping her company profitable through COVID, and building a patient base that spanned 35 states, Dr. Somi Javaid still walked into investor meetings where people looked around the room asking where her boss was. In this episode of The Capital Flex, I sit down with Dr. Somi Javaid, board-certified OB-GYN, surgeon, and founder of HerMD, who raised nearly $30 million to build evidence-based care in menopause, sexual health, and gynecology, all well before the market believed women’s health was venture-backable. She landed her first term sheet in five weeks. She also sat through pitch meetings where investors told her menopause didn’t need treatment and low libido wasn’t real. Somi didn’t cry in the room. She waited for the sushi and sake bar after. We talk about what happens when founders mistake access for alignment, and how quickly leverage can disappear in venture-backed rooms. Somi shares the story of an investor who blocked a competing term sheet to force a lower valuation, the “troublemaker” reputation she earned for refusing to play the good girl, and why she walked away from a $65 million term sheet in her first round.  More than anything, this is a conversation about holding onto your conviction when the room keeps trying to make you second-guess it. Key Takeaways: * Why being called “difficult” is often the cost of protecting your leverage * Why titles in one room don’t always translate to respect in the next * What happens when an investor decides the very problem you’re solving for doesn’t exist * How founders quietly give away power the moment they assume the room knows better than they do * Why Somi walked away from a $65 million term sheet in her first round * The hidden tradeoff that comes with taking capital too early My Reflection & Challenge: Somi let herself get small in rooms that had no business making her feel that way  because she had been trained to defer. That is not a character flaw. It is what the system is designed to do. Naming it is the first move. Deciding it won't happen again is the second. This Week's Challenge: * Where in your business are you deferring to a title instead of your own expertise — not because they've earned it, but because the room made you feel like they had? * And the next time someone disrespects you and follows it with a business-as-usual email the next day, what are you going to do with that? Links and Resources: https://www.drsomi.com/ [https://www.drsomi.com/]https://www.instagram.com/somijavaidmd/ [https://www.instagram.com/somijavaidmd/]https://www.instagram.com/hermdhealth/ [https://www.instagram.com/hermdhealth/]https://www.linkedin.com/in/somi-javaid [https://www.linkedin.com/in/somi-javaid]https://www.youtube.com/playlist?list=PLAdtK-yQpKoFH0c-43qwTLPf3-Io4FfjS [https://www.youtube.com/playlist?list=PLAdtK-yQpKoFH0c-43qwTLPf3-Io4FfjS]This episode is brought to you by Phoenix Fund Services To learn more about Phoenix Fund Services and connect with them, visit: https://www.phx-fs.com/ [https://www.phx-fs.com/] and https://www.linkedin.com/company/phoenix-fund-services/ [https://www.linkedin.com/company/phoenix-fund-services/] 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 [https://www.smartpodcastsolutions.com/] and Elevate Virtual Business Solutions. [https://elevatevbsolutions.com/]

S2EP2: What Would Jack Do? with Denielle Finkelstein & Thyme Sullivan

100 meetings. One summer. Not a single dollar raised. In this episode of The Capital Flex, I sit down with Denielle Finkelstein and Thyme Sullivan — co-founders of Unicorn, the company putting period product dispensers in the bathrooms of JP Morgan Chase, American Express, PepsiCo, Toyota, Blackstone and more. They knew how to build. They knew how to sell. What they didn't know was that the rooms they were walking into were never going to fund them — not because the business was weak, but because the people across the table didn't understand the customer and didn't care to. We talk about why staying away from venture gave them the freedom to walk away from 3,000 retail doors and pivot into a blue ocean nobody else had touched. The full capital stack beyond VC — angels, grants, revenue-based funding, SBA loans — and why most founders never look for it. And Jack Collins, a fictional CFO Thyme created to recover a debt ignored for over a year. Jack got a reply in 10 minutes. A payment plan. A handwritten thank-you note. Thyme and Denielle got silence. That is not a one-off. That is a pattern with a name. Key Takeaways: * Why 100 pitch meetings with no capital raised was a signal about the room — not the business * The full capital stack most founders don't know to look for: angels, grants, revenue-based funding and zero-interest loans * How staying away from venture gave them the autonomy to execute a pivot that would have been impossible with outside investors * Why leading with social impact in a pitch is how you get told to become a nonprofit — and what to lead with instead * The Jack Collins story: what it reveals about the bias still operating inside business relationships * Why revenue is capital — and how driving it changes the valuation conversation before you ever raise again My Reflection & Challenge: Denielle and Thyme did not stumble into staying away from venture. They made a deliberate choice to protect their ability to move. That kind of optionality is not luck. It is a structural decision made early that pays off when everything changes. The Jack story is the part I keep thinking about. Every woman in this room has a version of it. Naming it out loud is where the playbook starts. This Week's Challenge: * Where are you still bending toward what a room wants instead of building what you know is right? * Who in your network has ignored your follow-up? What would Jack say? Links and Resources: https://www.everystall.com/ [https://www.everystall.com/] https://www.linkedin.com/company/unicorn-in-every-stall/ [https://www.linkedin.com/company/unicorn-in-every-stall/] https://www.linkedin.com/in/thyme-sullivan/ [https://www.linkedin.com/in/thyme-sullivan/] https://www.linkedin.com/in/denielle-finkelstein-5637baa/ [https://www.linkedin.com/in/denielle-finkelstein-5637baa/] https://www.instagram.com/everystall/ [https://www.instagram.com/everystall/] 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 [https://www.smartpodcastsolutions.com/] and Elevate Virtual Business Solutions. [https://elevatevbsolutions.com/]

S2EP1: We Need to Build Our Own Infrastructure with Cindy Gallop

The venture capital system is not broken. It is working exactly as designed. And that is precisely the problem. In this episode of The Capital Flex, I sit down with Cindy Gallop — founder of Make Love Not Porn, builder of the world's first sex tech fund, and one of the most consequential thinkers in any room she walks into.  Cindy has been building for nearly 17 years in a sector VC refuses to fund and one which the financial system actively blocks. But this conversation is not about her fundraising experience. It is about what it would take to tear down the existing venture ecosystem and rebuild it through a female lens. We talk about what core financial architectures would look like, including the supporting systems and vehicles; how fund timelines and fund constructions would change to deliver on opportunities beyond the profiles and systems we have today; and what new thesis statements would activate women to invest across private markets. Especially when the math would say there’s potentially $5B already in the room. This is where the new system starts.  Key Takeaways: * What a female-designed venture system actually looks like at the structural level: timelines, incentives, and a completely different definition of aspiration * How emotional levers can move capital that rational arguments never will * The two groups sitting on significant capital, yet who have never been given a real reason to deploy it towards women * Why community is the mechanism to move money faster than any fund pitch * The $5 billion already in the room and the math that makes it real * Why the stories we don't tell shrink what founders believe is possible My Reflection & Challenge: What struck me most was the specificity underneath the vision. Cindy does not just say women should build a new system, she names who has the capital, what would move them, and why the current approach isn't working. That level of clarity is rare and it made this feel less like a conversation about what could exist and more like the first meeting for something that should.  This Week's Challenge: * Who in your network is sitting on capital they have never been asked to deploy toward women? What is the one thing they have lived through that would move them? * What room could you create, a dinner, a salon, a conversation, where the right women in the same space starts to move capital because of what they have in common? Links and Resources: https://makelovenotporn.tv/ [https://makelovenotporn.tv/] https://www.makelovenotporn.academy/ [https://www.makelovenotporn.academy/] https://www.instagram.com/cindygallop [https://www.instagram.com/cindygallop] https://www.instagram.com/makelovenotporn [https://www.instagram.com/makelovenotporn] https://www.linkedin.com/in/cindygallop/ [https://www.linkedin.com/in/cindygallop/] This episode is brought to you by Phoenix Fund Services Learn more about Phoenix Fund Services aby visiting: https://www.phx-fs.com/ [https://www.phx-fs.com/] and https://www.linkedin.com/company/phoenix-fund-services/ [https://www.linkedin.com/company/phoenix-fund-services/] 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 [https://www.smartpodcastsolutions.com/] and Elevate Virtual Business Solutions. [https://elevatevbsolutions.com/]

S1EP12 - You're Building a Rocketship with Emily Maginn

What happens when you walk into a raise with receipts, relationships, and a real product, then realize the only thing slowing the deal is how polite you are being? In this episode of The Capital Flex, I sit down with Emily Maginn, founder and CEO of EXO Technologies, a technology company building the “women’s health lab of the future”.  Emily bootstrapped her company into an enterprise-level platform before raising a single dollar, which placed her in rooms most first-time founders usually never enter. She found herself navigating tier-one funds, “super seed” semantics, and a real-time lesson in what happens when you approach fundraising with pure logic versus keen  strategy. We talk about the difference between stating facts and understanding leverage, how momentum can quietly disappear in small bites, and why ‘playing the game’ is more true in fundraising than anywhere else. Emily explains why so much fundraising advice falls short because it’s built for the wrong vehicle – they offer you airplane parts, but what you’re building is a rocketship.   Key Takeaways: * The aha moment she had when she understood how men protect momentum while women often slow it down in the name of courtesy * How she learned the difference between over-engineering and the power of saying ‘yes’ first * How she’s learning to find investors with conviction, not curiosity * Why women need more private capital, not more encouragement My Reflection & Challenge: Listening back, what stood out was not the size of the raise, but how quickly politeness can become friction. The moment you have permission to be in the room, you need to move like you have always belonged there.  This Week’s Challenge: Before your next investor conversation, write your “rocket ship criteria.” Ask yourself: * Do they understand what I am actually building? * Do they respect my conviction or try to shrink it? * Do they move with urgency or slow everything down? * If I stopped explaining, would they still have belief? Links and Resources: http://www.weareexo.com [http://www.weareexo.com/]https://www.linkedin.com/in/emily-maginn/ [https://www.linkedin.com/in/emily-maginn/]https://www.linkedin.com/company/exo-tech-group/ [https://www.linkedin.com/company/exo-tech-group/] 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 [https://www.smartpodcastsolutions.com/] and Elevate Virtual Business Solutions. [https://elevatevbsolutions.com/]

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 comps * What she learned about long cycles and how to spot a ‘no’ faster * What changed after her Y Combinator experience, why network effects matter and the reunion story you will not forget * Why there are critically important negotiation lessons women rarely get taught * Why “showing up” is a necessary strategy, as important as the follow-up, the ask, and the repetition My 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 it * Your minimum viable “yes” signals * The first number you will anchor with and why you can defend it * Your max number of meetings before you decide it is a ‘no’ * The phrases you will use to exit cleanly, quickly, and without guilt Keep it beside you during every pitch, your time is part of your valuation. Links and Resources: https://emberhealth.co/team/alison-greenberg/ [https://emberhealth.co/team/alison-greenberg/] https://www.linkedin.com/in/greenbergalison/ [https://www.linkedin.com/in/greenbergalison/] https://x.com/alis0nlaura/ [https://x.com/alis0nlaura/] https://emberhealth.co/ [https://emberhealth.co/]Email: allisonwith1l@emberhealth.co [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 [https://www.smartpodcastsolutions.com/] and Elevate Virtual Business Solutions. [https://elevatevbsolutions.com/]