The Capital Flex Podcast

Naseem Sayani
  • 5.0 (10)
  • 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.

  1. 6h ago

    S3EP4: Seriously, WTF with Cleo Escarez

    The pitch was going beautifully. The investor nodded through the whole deck and joked, "Where do I write a check?" Then Cleo Escarez asked if he had any other questions, and he asked why anyone wearing that much jewelry would be raising money for her company. When she recovered, he told her he knew exactly what her bracelet was worth because he had bought it for his ex-wife. In this episode of The Capital Flex, I sit down with Cleo Escarez. We met because of that story. She posted about it on LinkedIn on a Saturday night, I commented, and women across the ecosystem followed with their own versions of the same experience. Cleo is a TEDx speaker and the founder and CEO of Redyoos, an urban mine that refines precious metals from pre-loved jewelry and puts them back into the manufacturing of technology. Redyoos is a 2025 Earthshot Prize nominee. Before founding it, Cleo held leadership roles at Starbucks, Williams-Sonoma, Gap Inc., and Boma Jewelry. She describes her fundraising experience in three words: challenging, hilarious, and informative. We get into why she decided not to change how she shows up in pitch meetings, the investor feedback that she wasn’t spending enough time on herself on her team slide, and the questions about co-founders, marriage, and children that male founders are rarely asked. We also talk about pitching a circular model in clean tech, where the 2% of venture capital that reaches female founders shrinks even further, and how speaking about the problem took her to the TEDx stage without a dollar of paid marketing. Key Takeaways: How you can tune your language to each investor without changing how you show up.Why your team slide should lead with your own track record.How to prepare and rehearse answers to out-of-bounds questions so they don't pull you off the pitch.How to lead with the numbers when the room doubts the size of your market.Why thought leadership on the problem can build demand before you ever name your company.My Reflection & Challenge: Cleo called out a double standard every woman in her comments recognized. A male founder's watch reads as success. A female founder's bracelet becomes a diligence question. Her appearance was evaluated before her business was. She learned that what feels personal is the system doing what it was designed to do. The questions about a male technical co-founder, marriage, and children are predictable, which means they can be prepared for. The system isn't broken. It was built this way. She also learned that corporate success can work against a first-time founder. Years of having to be 10 times ahead taught her to wait for a certain ARR before claiming her accomplishments. One investor told her plainly to talk about her own brilliance. Now she leads with the numbers and stays in the game. This Week's Challenge: Rewrite your team slide so your own experience comes first, and give yourself as much time as anyone else on it.List the three out-of-bounds/prevention questions you dread most. Write a one-line answer/promotion pivot for each that returns the conversation to your market, and rehearse it out loud. A lot.Choose the one number that proves the size of your opportunity, and make it the first thing you say when someone questions the market. Stay in the game. It's not personal. Links and Resources: https://www.redyoos.com/ https://www.instagram.com/redyoos/ https://www.linkedin.com/in/cleoescarez/ Cleo's TEDx Talk 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 KNWN and Elevate Business Solutions.

    S3EP4: Seriously, WTF with Cleo Escarez

  2. Oct 28

    S3EP3: Mindset is Everything with Laura J. McDonald

    Before FLORA Fertility could raise its seed, a panel of A-rated reinsurers spent more than a year inside its actuarial models, deciding whether to put tens of millions of dollars in reserves behind every future claim. Laura J. McDonald says that diligence was harder than a Series B. It is also what unlocked the round. I'm a huge fan of what Laura and her co-founder, Dr. Christy Lane, have built. Laura is co-founder and co-CEO of FLORA Fertility, the first individually owned and underwritten fertility insurance policy. Her career sits at the intersection of women and financial security: she founded, scaled, and sold Canada's largest financial media company focused on women and wealth, and she has authored two bestselling personal finance books. She describes her fundraising experience in three words: lengthy, ongoing, but overall positive. We get into the two-plus years of behind-the-scenes work before the seed, from building net-new actuarial models to finding the broker who brought the reinsurers to the table. We talk about why FLORA needed an insurtech investor to lead the round before the rest of a $5M seed would say "we're in too," what it took to close a priced round with a long cap table, and how a Canadian parent company with a US subsidiary cost some smaller checks while keeping non-dilutive funding in reach. Key Takeaways: Why sequencing the hardest proof before the raise de-risks a category no investor has seen before.How to read a lead investor's LPs to see which doors the partnership can actually open.What a long tail of small checks and early option grants costs you when a priced round needs every signature.How your angel minimums shape who ends up on your cap table.Why a cross-border structure tends to cost the smaller strategic checks, but not the largest ones.My Reflection & Challenge: Laura called out how quickly a category gets labeled niche. Infertility affects one in six people, she notes, and the World Health Organization calls it a global health issue, yet fertility and women's health still get filed under "niche" in the room. She learned that when a category doesn't exist yet, the room needs someone who can underwrite the risk first. For FLORA, that was the reinsurers, and then a lead whose own expertise and LP base let every other investor commit. The system isn't broken. It was built this way. Laura's strategy was to sequence around it: prove the model, land the specialist, then raise. This mindset carried into every meeting. Laura and Christy never shied away from being moms with seven children between them and decades of experience. They walked in owning it. This Week's Challenge: Open your data room this week and add the three documents you would scramble for if an investor asked tomorrow. Then keep it current.Pull your cap table and list every holder whose signature a priced round would need. Confirm you have a current email for each one.Before your next investor meeting, look up who backs the fund. Ask where those LPs could open doors for you.Own it. Then walk in ready. Links and Resources: https://www.heyflora.com/ https://www.linkedin.com/in/laurajaynemcdonald/ https://ca.linkedin.com/in/christyclane https://www.linkedin.com/company/heyflora/ https://www.instagram.com/heyflorahealth 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 KNWN and Elevate Business Solutions.

    S3EP3: Mindset is Everything with Laura J. McDonald

  3. Oct 21

    S3EP2: Building Ahead of the Market with Melinda Wittstock

    She pitched one of the lead investors in Twitter on a mobile, AI-powered news platform with 500,000 people already creating content. He sat through the whole deck and then said, "Somebody's gonna do that." Then he explained that his firm invests on pattern recognition, and steered her to the door with a hand at the small of her back. In this episode of The Capital Flex, I sit down with my good friend Melinda Wittstock, a five-time serial entrepreneur and founder and CEO of Podopolo, an AI-powered podcast platform. She's also COO and co-founder of TailsTrails, and a venture partner and entrepreneur in residence at Zero Limits Capital, where we've worked together on a number of things. Melinda was named 2024's AI Pioneer of the Year by the California Investment Forum. Before building companies, she was an award-winning journalist, columnist, and TV host at The London Times, the Financial Times, the BBC, and others, and she hosts the Wings of Inspired Business podcast. She describes her fundraising experience in three words: frustrating, frustrating, and frustrating. We get into NewsiT, which had AI fact-checking and 500,000 content creators in 2011, back when investors still asked why she thought user-generated content, mobile, or the cloud would be big. We talk about the pitch competition where she spent 10 minutes talking about her customers, only to have an investor say he wished someone had talked about customers. And we get into Podopolo's $15 million seed, with term sheets in hand, that never closed because the VCs LP defaulted and the money never came through. Key Takeaways: Why “you’re trying to do too many things” often mistakes convergence for a lack of focus.Why asking every VC "Where are you in your fund?" is necessary before sharing a data room.What it costs when an investor with a term sheet tells you to go ahead and hire.How to turn prevention questions into promotion answers.Why a conservative model can cost you the round, and how to build bottom-up and still swing for the fences. My Reflection & Challenge: Melinda has been ahead of the market three times. Each time, the room told her the vision lacked focus. It didn't. It was built on convergence, and investors trained on pattern recognition read convergence as noise. Pattern recognition rewards whoever looks like the last success. Melinda saw it clearly when her 20-year-old son gave their chiropractor a 90-second pitch for his app and walked out with his first investor. In 25 years of building, that has never happened to her. Podopolo shows why a term sheet is not capital. When the LP money behind a fund stalls, the founder absorbs the delay: the hires, the burn, the months of "next week." The system isn't broken. It was built this way. Melinda's strategy now is to qualify every investor the way they qualify her, and to walk in knowing her value. This Week's Challenge: In every first investor meeting this week, ask "Where are you in your fund?" before you share a data room.Rebuild your model bottom-up, then build the version where you swing for the fences. Pitch that one, and state your ask as a sentence, not a question.If you're an investor or LP, ask one woman in your network who built her own wealth whether she's investing it or only giving it away. Then help her write her first check. Know your value. Then say it without a question mark. Links and Resources: https://linkedin.com/in/melindawittstock https://podopolo.com Wings of Inspired Business https://tailstrails.app (coming soon) 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 KNWN and Elevate Business Solutions.

    S3EP2: Building Ahead of the Market with Melinda Wittstock

  4. Oct 14

    S3EP1: Raising Capital is Not a Trophy with Ashlee Wisdom

    A fund had her data room. They ran focus groups. Every meeting ended with one more question, and every answer brought one more meeting. The moment another investor committed, that same fund asked for the term sheet. That isn't diligence. That's waiting for signal. In this episode of The Capital Flex, I sit down with Ashlee Wisdom, founder and CEO of Health in Her HUE, a digital health platform connecting Black women and women of color with culturally responsive providers, health content, and community. Ashlee has raised more than $4 million in venture capital. She's an Echoing Green Fellow, an Aspen Institute Healthy Communities Fellow, and a Rock Health Top 50 in Digital Health honoree, and her work has been featured in Forbes, Vogue, and Good Morning America. We get into how a viral MVP brought investors to her before she was even raising, and why she ended up pitching Series A investors when what she needed was a pre-seed round. We talk about the feedback that she sounded "too much like a social activist" for a VC room, how she learned to make the moral case and the economic case in the same breath, and what it took to tell her board the market was pointing somewhere they hadn't planned. Key Takeaways: Why an extended maybe costs a founder more than a quick no.The three questions Ashlee asks before she shares a data room.How to tell a mission story in the language of value, so budget holders care.What it took to learn how to manage her board and remember she's still the CEO.My Reflection & Challenge: Ashlee called out a venture system that claims to be analytical and turns out to be deeply subjective in practice. The fund that kept her in diligence for months didn't learn anything new about Health in Her HUE when it finally delivered a term sheet - they only knew that someone else had moved first. When investors wait for signal instead of leading with conviction, the founder pays for their hesitation: months of meetings, questions answered twice, and a company that still has to run while she's out raising. She learned that extended diligence is often a signal problem dressed up as rigor, and her answer was to set the terms of the process herself, starting in the first meeting. This Week's Challenge: Before your next investor meeting, write down three questions and ask them at the start: What's your typical process and timeline? What are your ownership targets? What milestones do you need to see at this stage?Look at your pipeline. Any investor whose process has run longer than they described is a maybe. Decide this week whether to ask for a yes or a no.If you're writing early-stage checks, ask one portfolio founder what she needs from you beyond the capital this quarter. Then make the one intro that answers it.Capital is not just money. It's a long-term relationship. Choose wisely. Links and Resources: https://www.linkedin.com/in/ashlee-wisdom-7114a040/ https://www.ashleewisdom.com/ https://healthinherhue.com/ https://www.instagram.com/healthinherhue/ Forbes: Women's Health Founders Are Rebuilding How Patients Find Care 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 KNWN and Elevate Business Solutions.

    S3EP1: Raising Capital is Not a Trophy with Ashlee Wisdom

  5. Sep 16

    BONUS - EP3: Let's Fill the Stadium

    One hundred thousand accredited women, each writing a $50,000 check, is $5 billion dollars. The Rose Bowl down the road from me holds ninety thousand people. We could fill it and change the system in an instant. In this third and final bonus episode of Season 2, I get into how founders navigate the system they were handed: non-dilutive funding, revenue before the raise, traction before the ask. I also make the case for one of the biggest unpulled levers in this ecosystem. Key Takeaways: Why proving revenue and traction before seeking for a venture check is a strong strategy.Why capital chasing mega later-stage AI deals is starving the early-stage pipeline, and potentially breaking the innovation flywheel on the way.Why we need to separate proving women can build businesses from closing the check.Why building strategic conviction is your secret sauce: know your customer better than anyone and stay flexible on how you raise.My Reflection + Challenge: Twelve conversations across Season 2 point to the same thing - the patterns and behaviors haven’t changed much, but our ability to flex new capital into the system is quite real. The question is what we’re doing about it and how quickly.  If you're an accredited investor, write down the number you could put into venture this year.Find one other woman in your network and ask her to do the same.If you're fundraising, cut any milestone you're chasing only to prove yourself, not the business.The system was built this way. It moves when the capital moves. Go move some. Links and Resources: Listen to Corinne's episode This episode is supported by IM8 — one scoop with 90+ essentials, co-founded by Beckham with advisors from Mayo Clinic, NASA, and Yale. Use code TheFlex10 for 10% off: https://www.im8health.com/TheFlex10 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 KNWN and Elevate Business Solutions.

    BONUS - EP3: Let's Fill the Stadium

  6. Sep 2

    BONUS - EP2: Mentors Give Advice. Allies Do The Work.

    Twelve conversations into Season 2, the same character kept showing up: not a co-founder, not an investor, but a man in the room whose only job was to point every question back to her. The clearest version of it came out of Karen's episode this season: her chairman sat in every fundraising meeting, said almost nothing about himself, and redirected every question straight back to her. That is the whole job in one move. This is the second wrap-up of Season 2, and the theme is allies. I trace what a real ally actually does versus what a polite one only says, the exact staging a first-time founder needs around her cap table and her board, and why an all-women fundraising network will only get you so far. Key Takeaways: The one-line test for what makes a real allyWhy "mentor" and "ally" are not the same job, and why founders who only collect the former stay capital-starvedThe exact staging a first-time founder needsWhy placing a male CFO at Series A can be a strategic hire and a strategic ally move at the same time The three moves that keep an investor relationship warm between raisesWhy an all-women fundraising network is wonderful – and also limiting My Reflection & Challenge: When enough founders build the same workaround independently, hiring the right CFO, seating the right chairman, staging the right mix of investors around them,  that is not twelve individual hacks. That is twelve founders understanding bias and navigating the system strategically. This Week's Challenge: Write down the two or three men in your network who have already opened a door for you without being asked. Reach out and ask for exactly one more specific thing: a warm intro, a seat at the table, a redirect in a meeting.  Activate their allyship. Links and Resources: Listen to Karen's episode This episode is supported by IM8 — one scoop with 90+ essentials, co-founded by Beckham with advisors from Mayo Clinic, NASA, and Yale. Use code TheFlex10 for 10% off: https://www.im8health.com/TheFlex10 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 KNWN and Elevate Business Solutions.

    BONUS - EP2: Mentors Give Advice. Allies Do The Work.

  7. Aug 19

    BONUS - EP1: Women Have Learned How to Speak Men

    For every two women who write a venture check, ninety-eight men do. That’s not a pipeline problem, it’s math, and it’s the pattern I’ve watched play out on repeat across two full seasons of The Capital Flex. In this solo wrap-up, I step out from behind the interview chair to name what I’ve heard across dozens of founder conversations: underestimation, dressed up as due diligence. I revisit three stories that still sit with me and trace them back to the same root causes: network failures, semantics, and a system still built to treat women as the exception in the room. I also share two stories I’ve never told on the podcast before: an LP check derailed by an investor’s husband on a Zoom call, and a client dinner where staying quiet made me, by way of stunned silence, part of the problem. Key Takeaways: Why the quick no is worth more to a founder than a warm maybe, and why so few investors are willing to give it.How three stories from across two seasons all trace back to the same root cause.How a senior wealth manager’s husband was able to block her LP check,, and what it revealed about who actually holds the checkbook.Why staying composed and quietly stunned at a client dinner made me part of the problem instead of above it, and what I’d do differently now.This Week’s Challenge: Think of the last deal, hire, or relationship where you got a slow maybe instead of a fast no. What would you do differently next time?Write down one moment you stayed quiet when something felt off. What caused that silence? What happens differently next time?If you’re already making investments, ask the founders if anything has gotten weird and how they handled it; also ask the fund managers you have invested with, how they handle it internally when something surfaces.Capital is not just money. It’s a long-term relationship. Choose wisely. Links and Resources: Listen to Somer’s episode Listen to Annie’s episode Listen to Dr. Somi’s episode 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 KNWN and Elevate Business Solutions.

    BONUS - EP1: Women Have Learned How to Speak Men

  8. Jul 22

    S2EP12: Even Taboo Can Get Acquired with Maria Molland

    A New York City subway agency called Thinx’s period underwear ads too inappropriate. The same stations were running ads for erectile dysfunction pills. In this episode of The Capital Flex, I sit down with Maria Molland, former CEO of Thinx, who fought that double standard, still built a globally recognized health brand, and then sold the company to Kimberly-Clark in 2022. Maria spent 25 years scaling businesses across consumer tech and healthcare, including 15 years running divisions at eBay and Yahoo. Today she’s an executive-in-residence at Frazier Healthcare Partners and an advisor to funds like Overwater Ventures and Goddess Gaia Ventures, where she helps build the next generation of women’s health companies. We get into what it took to raise when investors have decided a market for half the planet was too small, how Maria turned a censorship fight into a trajectory-changing press moment, and the questions about kids that no male CEO ever fields. We talk about strategic money that hands one investor the right to block other buyers, building for profit when securing funding hits walls, and why hard numbers are the data even bias can't argue with. Key Takeaways: Why, when investors wouldn't fund the vision, Maria stopped selling it and instead built the organic revenue and margins they couldn't argue with.How Maria turned censorship and taboo into earned press, building Thinx’ brand and sales on outrage and word of mouth instead of an ad budget she didn't have.How she handled a board member who questioned whether Maria could run the company with a baby at home. Which leadership skills have been her anchor through scandal, a revenue collapse, and rebuilding the supply chain on a deadline, ensuring Maria remained steady and kept the team moving forward.My Reflection & Challenge: Maria ranked profitability as her number one value at Thinx. Above the mission. Above breaking taboos. Above everything, the brand stood for publicly. When you build in a space where the stakes are personal, the mission is the fuel. It's what makes the rejection bearable. So often being told to put profit first can feel like a betrayal of the reason you started. But Maria didn't see it that way - and it's a lesson every founder can learn. She understood that purpose without profit doesn’t secure longevity. Profit isn't the enemy of purpose. It's actually THE lever needed to keep it alive, no matter what. This Week's Challenge: If investors won't fund your vision, start building the proof. What is the one metric in your business that, if undeniable, would change the conversation?Write down your cultural values and rank them in order. Maria put profitability first, ahead of the mission, because she knew the mission needed profit to survive. If profitability isn't near the top of your list, ask yourself why.To ensure an M&A outcome, start learning how your ideal buyer operates right now. The founders who get acquired are the ones who build with their target buyer in mind.Capital is not just money. It’s a long-term relationship. Choose wisely. Links and Resources:  https://www.linkedin.com/in/mariamolland/  https://www.frazierhealthcare.com/  https://www.overwater.vc/  https://www.ggventuresgroup.com/  https://www.kimberly-clark.com/en-us/  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 KNWN and Elevate Business Solutions.

    S2EP12: Even Taboo Can Get Acquired with Maria Molland
See All (32)

Trailer

Ratings & Reviews

5
out of 5
10 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
    32
  • Rating
    Clean
  • Copyright
    © 2026 The Capital Flex Podcast
  • Show Website
    The Capital Flex Podcast

You Might Also Like