The Check Writers Room

Sydney, Yasmin and Shalanda
  • 5.0 (6)
  • Entrepreneurship

The Check Writers Room is a groundbreaking podcast where the real power brokers of venture capital talk shop—unfiltered. Hosted by three Black female General Partners—Sydney Thomas (Symphonic Capital), Shalanda Armstrong (100KM Ventures), and Yasmin Cruz Ferrine (Visible Hands VC)—the show pulls back the curtain on how venture capital actually works. From how investment decisions get made to why deals get a yes or a no, The Check Writers Room delivers candid, practical insights founders rarely hear out loud. This isn’t aspirational advice. It’s lived experience from investors who have collectively raised and deployed over $50M, invested in hundreds of companies, and supported thousands of founders across tech, fintech, consumer, and enterprise. Each episode breaks down real market dynamics, exposes the unspoken rules of fundraising, and offers founders actionable guidance grounded in today’s realities—not outdated Silicon Valley playbooks. Designed for founders, operators, and ecosystem builders—especially the next generation of Gen Z and Millennial entrepreneurs—the show fills critical knowledge gaps by democratizing access to venture capital insight, networks, and decision-making frameworks that have traditionally been gatekept. With biweekly episodes, an interactive “Ask a VC” segment driven by real founder questions, and appearances from trusted peers and ecosystem leaders, The Check Writers Room is more than a podcast—it’s a masterclass and a community for builders serious about building enduring companies.

  1. Aug 13

    The Room with Standalones, Features, and Strategic Planning

    Part two of our conversation with Jessica Loché-Eggert delves into the challenges faced by healthcare technology startups, emphasizing the importance of understanding the distinction between building a standalone product and a feature within a larger conglomerate. It also explores the significance of deep integration in the workflow and the possession of proprietary data for achieving a billion-dollar valuation. Additionally, it provides insights into the sales component of healthcare and the strategic considerations for acquisition and exit. The conversation delves into the complexities of preparing for and navigating the acquisition process, emphasizing the need for strategic planning, negotiation skills, and a deep understanding of the acquisition landscape. It also highlights the importance of managing relationships, maintaining momentum, and aligning expectations with potential buyers. Takeaways Healthcare technology startups must understand the distinction between building a standalone product and a feature within a larger conglomerate.Deep integration in the workflow and proprietary data are crucial for achieving a billion-dollar valuation in the healthcare technology space.The sales component of healthcare, strategic considerations for acquisition and exit, and the importance of disassociating from potential acquirers are key factors for startup success in the healthcare technology sector. Strategic planning and negotiation are crucial for successful acquisitions.Maintaining momentum, managing relationships, and aligning expectations are key factors in the acquisition process.

  2. Aug 6

    The Room with Premeditated Exits and PE Relationships

    This weeks' episode is the beginning of a two part conversation with Jessica Loché-Eggert of Madison West Partners. Madison West is a healthcare market intelligence and corporate development firm. They track who is acquiring, what buyers value, and why deals happen, then help healthcare technology companies grow and get acquired. The conversation begins with a discussion on investor relationships and dynamics. It then delves into founder challenges and support, covering venture capital strategy, seed funding, building with exit in mind, and PE and healthcare technology exits. The discussion delves into the future of seed funding, the impact of venture capital strategy shifts, and the considerations for building a company with an exit in mind. Takeaways Investor relationships play a crucial role in the startup ecosystem.Founder challenges often require a strong support system. Seed funding is shifting away from the traditional Silicon Valley model.Building a company with an exit in mind requires careful consideration of valuation and potential acquirers.PE-backed acquisitions in healthcare technology often involve different valuation metrics and considerations.

  3. Jul 23

    The Room with Women's Healthcare, Phia Shopping, and NCAA NIL

    The conversation covers the rise of women's health as a cool and important topic, the prevalence of fraudulent activity in tech startups, the impact of famous parentage on startup success, and the Scout company's role in the NIL era for college athletes. Takeaways Women's health is gaining prominence and importance, driven by millennial attitudes towards healthcare.Fraudulent activity in tech startups is a common practice, but founders need to be aware of the risks and consequences.Famous parentage can impact a startup's success and public perception.The Scout company is making a significant impact in the NIL era for college athletes, providing financial infrastructure and compliance support. Scout's comprehensive support for student athletesThe importance of understanding family history and heritage

  4. Jul 16

    The Room with The Midas List, The State of the Market, and All Raise

    The conversation covers the importance of women in venture capital, and the impact of the Midas list on VC firms. It delves into the world of venture capital, focusing on the Midas List, fundraising challenges, ecosystem building, and the importance of supporting emerging managers and women in VC. It also explores the joy and personal reflections of the participants. Takeaways Importance of women in venture capitalThe Midas list and its impact on VC firms Venture Capital and Emerging ManagersBuilding Trust and Relationships in Venture CapitalImportance of Diversity and Inclusion in Venture Capital

  5. Jul 10

    The Room with Storytelling, Optimization, & Enterprises

    The conversation delves into the involvement of corporations in the startup ecosystem and the ways in which startups can benefit from working with corporations. It emphasizes the importance of long-term vision and partnership building for startups, highlighting the need to look beyond short-term gains and focus on sustainable growth. Takeaways Corporations as Startup PartnersLong-Term Vision for Startups

  6. Jun 25

    The Room with IPOs, DevOps, and Founders

    The conversation covers a range of topics including IPO valuations, LP and private market impact, investment strategies, university endowments, and the impact of DevOps and AI on the software sector. It delves into the challenges and opportunities faced by investors, LPs, and organizations in the current market landscape. The conversation delves into the challenges of technical debt in enterprise software, the evolution of technology and software, the value of data and in-house development, advice for new founders, and personal growth and joy. It emphasizes the need for sustainable and scalable solutions, the importance of agility and active learning, and the necessity of knowing yourself deeply as a person and a founder. Takeaways Unprecedented IPO valuationsImpact of DevOps and AI on the software sector The impact of technical debt on enterprise software and the need for sustainable solutionsThe importance of agility, active learning, and trying, failing, and iterating in entrepreneurship

  7. Jun 18

    The Room with William Crowder

    The conversation with William Crowder delves into the challenges and opportunities in the venture capital industry. It explores the cyclical nature of venture capital, the impact of technology and innovation, and the opportunities in regulatory technology. William shares insights on navigating downturns, the importance of adapting to industry changes, and the need for a deeper understanding of the venture capital landscape. Takeaways Venture Capital ChallengesAdapting to Industry Changes Chapters 00:00 Introduction and Background06:34 Navigating Downturns17:16 Challenges in the Industry24:57 Impact of Technology and Innovation35:12 Opportunities in Regulatory Technology

  8. Jun 11

    The Room with AI and Investor Strategy

    The conversation covers the acquisition of Everlane by Shein, the impact of AI on venture investing, and the challenges of evaluating startups and founders. Dr. Amisha Miller provides insights on the use of AI in venture investing and its potential biases. The discussion also delves into the implications of systematic barriers and biases in the evaluation of startups and founders. The conversation delves into the use of AI in evaluating potential and the challenges of incorporating AI into the investment process. It also explores the systemic aspects of venture capital and the need for structural change. The discussion touches on the limitations of AI in predicting outliers and the importance of context in decision-making. Takeaways Acquisition of Everlane by SheinImpact of AI on venture investingChallenges of evaluating startups and founders Structuring evaluation of potential can help address human evaluation biases in VC.AI may be less biased than humans in evaluating gender and race, but its ability to predict outliers and contrarian thinking is uncertain.The systemic aspects of venture capital require a shift in focus from resource seekers to changing the system.The use of AI in evaluating potential and the investment process requires careful consideration and a one-step-ahead approach. Chapters 00:00 Systematic Barriers and Biases in Evaluation51:02 The Limitations of AI in Contextual Understanding

See All (18)

5
out of 5
6 Ratings

About

The Check Writers Room is a groundbreaking podcast where the real power brokers of venture capital talk shop—unfiltered. Hosted by three Black female General Partners—Sydney Thomas (Symphonic Capital), Shalanda Armstrong (100KM Ventures), and Yasmin Cruz Ferrine (Visible Hands VC)—the show pulls back the curtain on how venture capital actually works. From how investment decisions get made to why deals get a yes or a no, The Check Writers Room delivers candid, practical insights founders rarely hear out loud. This isn’t aspirational advice. It’s lived experience from investors who have collectively raised and deployed over $50M, invested in hundreds of companies, and supported thousands of founders across tech, fintech, consumer, and enterprise. Each episode breaks down real market dynamics, exposes the unspoken rules of fundraising, and offers founders actionable guidance grounded in today’s realities—not outdated Silicon Valley playbooks. Designed for founders, operators, and ecosystem builders—especially the next generation of Gen Z and Millennial entrepreneurs—the show fills critical knowledge gaps by democratizing access to venture capital insight, networks, and decision-making frameworks that have traditionally been gatekept. With biweekly episodes, an interactive “Ask a VC” segment driven by real founder questions, and appearances from trusted peers and ecosystem leaders, The Check Writers Room is more than a podcast—it’s a masterclass and a community for builders serious about building enduring companies.

Information

  • Creator
    Sydney, Yasmin and Shalanda
  • Years Active
    2026
  • Episodes
    18
  • Rating
    Clean
  • Copyright
    © 2026 Sydney, Yasmin and Shalanda

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