S2EP11: The Behaviors I Can't Unsee with Karen Drexler

S2EP11: The Behaviors I Can't Unsee with Karen Drexler

She had already made this investor a lot of money. When she came back to pitch her own company, he told her he doesn't back founders who look like her, then asked how many kids she was planning to have. Making investors' money is supposed to earn you a real shot the next time around - maybe just not for women. In this episode of The Capital Flex, I sit down with Karen Drexler, a serial med tech founder, operator, and board director who has spent 25 years building, scaling, and selling healthcare companies. Karen worked with a team at LifeScan to make it possible for people with diabetes to test their own blood at home, before the company was sold to Johnson & Johnson. Then she built her own company and sold it to Roche, one of the biggest names in global healthcare. Now she sits on public and early-stage boards, advises founders through Springboard and Astia, and recently co-founded a new women's health company. We get into the moments nobody puts in a pitch deck. Karen had already sold companies to two of the biggest names in global healthcare and still had to bring a man into the room to close the deal. We talk about founders who scrubbed words like "breast" and "fallopian tubes" from their pitch decks because the male investors couldn't hear them without giggling. And we name the pattern underneath it all - women get asked what could go wrong, men get asked how big the opportunity could get. It turns out prevention versus promotion dynamics have been at play for quite a long time. Key Takeaways: * Creating exceptional returns should expand opportunity. For many women, it still doesn't.  * Sometimes the only thing standing between a woman and a ‘yes’ is a well-credentialed man sitting on her side of the table. We can take offense, or we can lean into strategy * Investors can often let immaturity get in the way of saving lives. How we respond matters. * Before you pitch, study what an investor has already backed. If nothing in their portfolio looks like your deal, they’re probably not your investor. Move on. * Your team and board are more than advisors—they're signal. Choose them like it matters. * Women’s health companies have been producing big wins for decades. Investors who keep overlooking it are not being cautious. They’re mispricing and underestimating it. * Improving your fundraising process starts with investor fit. Study what they've already backed. Their portfolio will tell you far more than their website ever will.  My Reflection & Challenge: What I keep coming back to is this: Karen is still giving advice to founders today that echoes her own experience 20+ years ago. That is how little has changed. She had the track record, the technology, and the exits. And she still had to bring on a board chair whose job was simply to be the man in the room. Her experience alone was not enough. Your job is to see the system for what it is and learn to navigate. Finding the rooms that will back your business on its own merits is critical. This Week's Challenge: Before your next raise, do the work before you walk in: 1. Research every investor you’re targeting. If nothing in their portfolio looks like your deal, take them off the list and redirect your energy where it can pay off. 2. Do not walk into a pitch without a champion already in the room. One believer who speaks before you do can shift the dynamic in the room before you say a word. 3. Look at your team and your board. Do their credentials reinforce your foundation and future potential? If not, make adjustments. Capital is not just money. It’s a long-term relationship. Choose wisely. Links and Resources:  https://sb.co/  [https://sb.co/ ] https://www.astia.org/  [https://www.astia.org/ ] https://www.linkedin.com/in/karendrexler/  [https://www.linkedin.com/in/karendrexler/ ] 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 Business Solutions. [https://elevatevbsolutions.com/]

S2EP10: We Launched the Category with Leah Solivan

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. Nine years later, she had raised $50 million and exited TaskRabbit to IKEA. Now, as founder of Precedent VC, a pre-seed and seed fund backing category-defining teams, she’s writing the checks. We get into what fundraising looks like when you're years ahead of the market, and the investors you meet can’t see around the corner as you can. We cover the product demo that built conviction faster than any pitch deck could and the sequencing strategy most founders don’t leverage enough. We also talk about the random Silicon Valley office tour that turned into one of the most talked-about acquisitions in gig-economy history. Key Takeaways: * If you're building ahead of the market, expect to pitch 50 to 100 investors per round. Early conviction is rare. That's what creates opportunity.  * When the room can't connect with a problem they've never had, stop explaining and start demonstrating. Live experiences can make the problem tangible and build conviction faster than a great pitch deck.  * Treat every fundraising conversation as mutual diligence. The way an investor engages today is often the best predictor of your partnership tomorrow.  * Most founders lead with their best investors and wonder why the pitch falls flat. Save your highest-leverage conversations until your story has reached its full potential.  * Conviction is a muscle, not a trait. Contradictory advice can come from the most brilliant of people. Listen carefully, absorb every perspective, then make the decisions only you can make.  My Reflection & Challenge: Leah sat across from an investor who called her "babe" mid-pitch. She finished the presentation and left. No drama, no confrontation, just a clean read on capital that would cost too much. Most founders override that instinct because the check feels too important. Leah didn't. That's a skill every founder can flex.  Knowing which rooms to walk away from is only half the equation. The better question is how to create conviction in the rooms worth staying in. Leah's live demo did what no pitch deck could: it allowed the room to experience the problem instead of simply hearing about it. She created the conditions for people in the room to see it for themselves.  This Week's Challenge: Before your next investor conversation, do these three things: 1. Find out if this investor has ever lived the problem you're solving. If they haven't, your job is to help them experience it.  2. Look at your investor list and sort it honestly. The names you most want to hear yes from should be the last ones you pitch. Protect them until your pitch has been sharpened by every earlier conversation.  3. Write one sentence that answers this question: Why are you the only founder who could build this specific company? Not your team. Not your traction. You. If you can write it in one sentence, you're ready to say it in the room.  Capital is not just money. It’s a long-term relationship. Choose wisely. Links and Resources:  https://www.linkedin.com/company/precedent-vc/   [https://www.linkedin.com/company/precedent-vc/ ] https://www.linkedin.com/in/leahsolivan/    [https://www.linkedin.com/in/leahsolivan/ ] 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 Business Solutions. [https://elevatevbsolutions.com/]

S2EP9: Going Public via a Reverse-Merger with Sabrina Johnson

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 solely in women's health. Daré builds science-backed solutions for women across contraception, menopause, arousal, fertility, and vaginal health, use cases that have been chronically underfunded because the people controlling the capital never personally needed them. We dig into the ‘relatability gap’, the structural reason investors fund problems they've lived and pass on problems they haven't,  how Sabrina used a reverse merger to secure capital and take her company public, and why Daré has created investment opportunities for the very women its products are built to serve.  Key Takeaways: * Venture isn't the only path to capital. A reverse merger is a legitimate alternate strategy, among others, and needs a depth of insight to be successful.  * Women are the largest consumers of healthcare. Investors see those numbers and think the market is served. They don’t see that most of the spending isn't for her. * For the first time, the women who actually need these products can invest in the company building them. Not hedge funds. Not institutions. The women the industry spent decades ignoring. * Investors are humans first and capital allocators second. If they can't feel the problem you're solving, no market-size number is going to convince them. Lead with the patient always. My Reflection & Challenge: Like so many others, Sabrina had the science and the market; she just didn't have anyone willing to invest in women's health. And after more than a year facing closed doors, she stopped knocking and pivoted. Instead of waiting, what I love is that she bet on what she already knew and took Daré public without them. It wasn't easy. But it was on her terms. And that made it worth it. This Week's Challenge: Before your next investor conversation, do three things: 1. Find out if these investors have ever personally faced the problem you’re solving. If they haven’t, figure out how you’ll make them feel it before asking them to fund it. 2. Map the room beyond your champion. The person across the table is not always the one making the final call. 3. Know your options outside venture. Every one of them. Before you’re in a position where you need them. Capital is not just money. It’s a long-term relationship. Choose wisely. Links and Resources:  https://darebioscience.com/   [https://darebioscience.com/ ] https://www.linkedin.com/in/sabrina-johnson-27799829/  [https://www.linkedin.com/in/sabrina-johnson-27799829/ ] https://www.linkedin.com/company/dare-bioscience/  [https://www.linkedin.com/company/dare-bioscience/ ] https://www.instagram.com/darebioscience   [https://www.instagram.com/darebioscience ] 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 Business Solutions. [https://elevatevbsolutions.com/]

S2EP8: It Takes 99 Duds to Find Your Stud with Aagya Mathur

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 never have to do it again. In this episode of The Capital Flex, I sit down with Aagya Mathur, co-founder and CEO of Aavia, an app and data platform that unlocks insight into how hormones impact everything from sleep and energy to mental health and injury risk. With over 85 million longitudinal data points, Aavia can flag various conditions (e.g., PMOS, PMDD) that typically take 7-10 years to diagnose, decreasing downstream conditions and costs. It also helps inform daily personalized recommendations to optimize her lived experience. We get into two investor moves nobody talks about: stringing a founder along for months with no intention of closing, and signing commitment paperwork for a check that was never real.  We also discuss what actually moves the needle, knowing your numbers cold, building a cross-gender founder network, and why broadening your category on your own terms beats letting an investor do it for you.  Key Takeaways: * When an investor keeps moving the goalposts, that’s a no. Stop waiting for a different answer. * Male founders move through this ecosystem differently than female founders, which is why cross-gender networks are so important. Build those connections before you need them; it creates visibility into strategies that could help. * Female investors can carry the same biases as male investors. Shared gender is not shared experience. * Don't let a category label define your investor pool. If the framing isn't working, change it. It’s not compromise – it’s strategy. My Reflection: The restaurant story hit me the hardest. Aagya walked in prepared and polished. She was ready. But it didn’t matter, because there was no pitch. Just a man performing power over a subpar dinner. No amount of planning will prepare you for someone who shows up with no intention of investing. That's not a failure of preparation. That's the failure of a system that keeps letting the wrong kind of men into the room. But Aagya didn't let the dinner define her, or slow her down. She just recalibrated and kept showing up. Which is all any of us can do. This Week’s Challenge: 1. Before your next investor conversation, do your homework on the fund. When did they last write a check? How much of the fund has been deployed? Have they ever had to return capital? These are not aggressive questions. Don’t let anyone tell you otherwise. 2. Find one male founder in your network who has been through your current fundraising stage. Ask what their term sheets look like and what they flagged as predatory. That intel is free, so use it. 3. If an investor misses your agreed-upon timeline, give them one more date. Just one. If they miss that, move on. You don’t wait for anyone. Links and Resources: https://www.linkedin.com/in/aagyamathur/ [https://www.linkedin.com/in/aagyamathur/]  https://www.linkedin.com/company/aavia/ [https://www.linkedin.com/company/aavia/]  https://aavia.io/ [https://aavia.io/]  https://www.instagram.com/aavia.io/ [https://www.instagram.com/aavia.io/] 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 Business Solutions. [https://elevatevbsolutions.com/]

S2EP7: Women Have No Protection In This Ecosystem with Sarah Kraft

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 11 years of operations and growth experience scaling consumer and B2B2C startups from zero to $1M+ ARR, has grown Koil to more than 440,000 users and is actively raising her seed round. We get into the ugly reality of early-stage fundraising: why women founders are the most exposed people in the room, what it costs to hold a hard boundary, the fawn response,  and what a real vetting framework looks like in practice.  And we say out loud what many founders wish we wouldn’t: success doesn’t equal credibility in this ecosystem. For all the talk of open doors and equal opportunity, many women are still penalized for every single win. Key Takeaways: * Women founders walk into investor conversations with no protection. That gap is structural, not personal. * The fawn response is real. Women comply to stay safe rather than enforce a boundary. We have to call it out to start interrupting it. * Bad behavior in the room gets a pass. The woman who calls it out? Not so much. And that’s not an accident. * A personal vetting framework (daylight meetings, public spaces, limited duration, no alcohol) is not overcautious. It is a necessary infrastructure. * Cross-gender allies exist and matter. The best ones listen, say what they see, and get you in the room without asking you to make yourself smaller.  My Reflection We tell women to earn their way in. Build the traction. Prove the model. Sarah did all of it, but the momentum still didn’t keep her safe. It just altered what she was up against. This is the pre-pitch advice nobody gives you. A strong idea and solid traction should be enough, but for women, the pitch is never just the pitch. Women walk in selling a company. The people in the room decide whether they like her before they decide if they like the business. The idea was never the only thing on trial. The framework Sarah built to protect herself is just as strategic as the company she’s scaling. Every safeguard is necessary. And the system that created that necessity isn’t interested in fixing any of it. This Week's Challenge: Before your next round, take stock: 1. Set your boundaries before the next meeting: time of day, duration, and setting. Write them down and stick to them. 2. Find one person in your network who has met with your target investor. You want intel on how they treat founders, not just whether they write checks. 3. Notice the moment you’re about to override your gut. That’s scarcity talking. Stop for a moment and name what you’re agreeing to. Capital is not just money. It’s a long-term relationship. Choose wisely. Links and Resources:  https://koil.life/  [https://koil.life/ ] https://www.linkedin.com/in/kraftsarah/  [https://www.linkedin.com/in/kraftsarah/ ] https://www.instagram.com/koil.life/  [https://www.instagram.com/koil.life/ ] https://thecapitalflexpodcast.buzzsprout.com/  [https://thecapitalflexpodcast.buzzsprout.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 [https://www.smartpodcastsolutions.com/] and Elevate Business Solutions. [https://elevatevbsolutions.com/]