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The Check Writers Room

The Check Writers Room

By: Sydney Yasmin and Shalanda
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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exposes the unspoken rules of fundraising, and offers founders actionable guidance grounded in today’s realities—not outdated Silicon Valley playbooks.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.

2026 Sydney, Yasmin and Shalanda Economics Leadership Management & Leadership
Episodes
  • The Room with IPOs, DevOps, and Founders

    The Room with IPOs, DevOps, and Founders
    Jun 25 2026

    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 valuations
    • Impact of DevOps and AI on the software sector The impact of technical debt on enterprise software and the need for sustainable solutions
    • The importance of agility, active learning, and trying, failing, and iterating in entrepreneurship
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    46 mins
  • The Room with William Crowder

    The Room with William Crowder
    Jun 18 2026

    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 Challenges
    • Adapting to Industry Changes

    Chapters

    • 00:00 Introduction and Background
    • 06:34 Navigating Downturns
    • 17:16 Challenges in the Industry
    • 24:57 Impact of Technology and Innovation
    • 35:12 Opportunities in Regulatory Technology
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    39 mins
  • The Room with AI and Investor Strategy

    The Room with AI and Investor Strategy
    Jun 11 2026

    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 Shein
    • Impact of AI on venture investing
    • Challenges 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 Evaluation
    • 51:02 The Limitations of AI in Contextual Understanding
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    57 mins
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