S2EP10: We Launched the Category with Leah Solivan

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/]

S2EP6: Desperation Made Me the Grant Queen with Corinne Vargas

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 SmartCHARTS from a basement on Northwestern’s campus, and had 1,200 therapists onboarded in less than 48 hours.  Of the three founders in her accelerator cohort, Corinne was the only one to walk away without a check. The other two founders? A male founder with a napkin-based concept, and the other, also a male founder with only an MVP.  So she found another way. Today, SmartCHARTS is over 72% non-dilutive funded. Corinne maintains majority equity, and the company is advancing toward NSF SBIR Phase 2 review while securing enterprise pilots with major health systems. We discuss what it felt like to field the “where’s your male co-founder” question on repeat. We get into the language women use to disqualify themselves before anyone in the room can do it for them. And, most importantly, we talk about what it takes to find capital on your own terms when the system keeps shutting you out. Key Takeaways: * Comparable traction, credentials, and metrics do not guarantee comparable outcomes. The data lives in the pattern, and Corinne could point to it directly. * The “where’s your male co-founder” question is structural bias showing up in real time. Prepare for it and know how to redirect it. * Drop the self-disqualifying language. “Non-technical founder” and “early stage” are not always necessary to say, and male founders simply don’t say them. * Pitch competitions are a real, underused pathway to non-dilutive capital. LinkedIn is one of the most effective places to find them. * Federal grant applications reward factual rigor and honest risk assessment, which is the opposite of the investor-optimism playbook. Knowing the difference can unlock new capital options. * The investors who find you when you aren’t looking, and who believe before you ask, often end up being the most valuable people on your cap table. My Reflection & Challenge: There’s a moment in this conversation I keep coming back to: Corinne sitting at drinks with the two male founders who got the checks, and they tell her, “You did it right.” Not as pity, but as a genuine reckoning with what the system had just shown them. What Corinne built wasn’t a workaround. It was a masterclass in staying in the game when the game wasn’t designed for you. She didn’t lose equity chasing the wrong capital. She built a company surrounded by people who truly believed in the opportunity. This Week's Challenge: Before your next round, take stock: 1. Map where your current capital is coming from and ask yourself honestly if any of it came with strings that cost more than the check was worth. 2. Look up one federal grant program that applies to your sector. Open the application.  3. Remove “non-technical founder” and “early stage” from your pitch vocabulary, unless you’re in a room where those phrases serve you and you can say exactly why. Capital is not just money. It’s a long-term relationship. Choose wisely. Links and Resources:  https://www.mysmartcharts.com/ [https://www.mysmartcharts.com/]  https://www.linkedin.com/in/corinnevargas/ [https://www.linkedin.com/in/corinnevargas/]   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/]