The Capital Flex Podcast

She drew the blueprint for the gig economy in 2008. Uber. Lyft. DoorDash. They all came later. In the moment, though, she navigated significant disbelief and had an investor call her “babe” mid-pitch. . She built it anyway. In this episode of The Capital Flex, I sit down with Leah Solivan, founding CEO of TaskRabbit, the company that built the gig economy before any of us were calling it that. Nin...

She had the science, the credentials, and a market that encompassed half the population. The people with the capital just didn't care enough about women's health to bet on it. So she stopped trying to convince them. In this episode of The Capital Flex, I sit down with Sabrina Martucci Johnson, founder and CEO of Daré Bioscience, the only publicly traded company on any exchange working so...

He was never interested in investing. He just liked feeling powerful. So he took Aagya Mathur to dinner, told her why her company would fail, and picked up the check because he was “older and richer.” Nobody warns you about those kinds of investors, the ones who treat your pitch as entertainment and your time as theirs to waste. Aagya sat through that dinner and then built a playbook so she’d neve...

The most dangerous part of fundraising is not the bad term sheet. It’s the room. And when you’re early-stage, with no HR, no legal shield, and no institutional backup, the only protection is you . In this episode of The Capital Flex, I talk with Sarah Kraft, founder and CEO of Koil AI, a platform helping teens figure out who they want to be and how to get there. Sarah, a world champion sailor with...

You have the product,  the paying users, and the proof. But the men with the money keep saying no. What then? In this episode of The Capital Flex, I sit down with Corinne Vargas, founder and CEO of SmartCHARTS, a healthtech company turning rehabilitation data into clear, decision-ready insights for patients and care teams. A former actuary turned speech-language pathologist, Corinne built SmartCHA...

She had a solid product that solved a real problem, plus unshakeable conviction. And yet, before she could get down to business, Meredith McAllister still had to prove she belonged in the room.  In this episode of The Capital Flex, I sit down with Meredith McAllister, two-time founder, advisor, and writer based in Kansas City. Meredith built and sold Compost Collective, then co-founded Marma Healt...

She had nine commercial partners, FDA clearance, and a 25-year medtech track record. Still an investor stopped her mid-pitch to ask whether breast cancer was “still a thing.” In this episode of The Capital Flex, I sit down with Marissa Fayer, engineer, operator, and CEO of Deep Look Medical , an FDA-cleared imaging software company helping radiologists visualize soft tumors in dense tissue with a...

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 t...

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 r...

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 t...

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 platf...

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 ra...

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 he...

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...

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 ga...

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 lay...

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 dec...

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 detecti...

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...

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 autho...

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 ca...

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 narrat...

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 unfiltere...