The Check Writers Room
Sydney, Yasmin and Shalanda·16 episodes·Weekly
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exposes the unspoken rules of fundraising, and offers founders actionable guidance grounded in today’s realities—not outdated Silicon Valley playbooks.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.
Episodes
Latest Episode
July 23, 2026 · 45m
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 athletes The importance of understanding family history and heritage
More Episodes
Jul 16 · 41m
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.TakeawaysImportance 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
Jul 10 · 40m
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.TakeawaysCorporations as Startup PartnersLong-Term Vision for Startups
Jun 25 · 46m
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. TakeawaysUnprecedented 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
Jun 18 · 39m
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.TakeawaysVenture Capital ChallengesAdapting to Industry ChangesChapters00:00 Introduction and Background06:34 Navigating Downturns17:16 Challenges in the Industry24:57 Impact of Technology and Innovation35:12 Opportunities in Regulatory Technology
Jun 11 · 56m
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.TakeawaysAcquisition 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.Chapters00:00 Systematic Barriers and Biases in Evaluation51:02 The Limitations of AI in Contextual Understanding
Jun 4 · 9m
The episode features all three hosts in person and can be accessed by clicking the link here. The hosts speak about Venture Capitalism and founding a business with Angela Yee and Stacey Tisdale on their Wealth Wednesdays segment of Way Up with Angela Yee. The episode is a special one and promises a dynamic and enjoyable experience for the listeners.TakeawaysPodcast episode features all three hosts in personAccess the episode by clicking here. Sharable episode link: https://youtu.be/5lhPEMH3-qs?si=O3871cPaYFcSdfKnChapters00:00 Introduction to Special Episode01:14 Teaser 103:57 Teaser 205:44 Teaser 307:17 Teaser 4
May 21 · 32m
The conversation covers a range of topics including venture capital and fund management, investment in healthcare technology, discussion on health-tech companies, healthcare technology and hospital sales cycles, fund management and distribution challenges, and personal joy and inspiration.TakeawaysVenture Capital and Fund ManagementHealthcare Technology and AIInvestment Strategy and Fund LifecycleChapters0:00 Fund Management and Continuation Vehicles12:55 Would You Write the Check?: iCardio27:34 Personal Joy and Inspiration
May 14 · 35m
The conversation covers two primary themes: influencer marketing and go-to-market strategy, and the role of women in AI and technology. The first theme explores the impact of influencer marketing and the effectiveness of go-to-market strategies, while the second theme delves into the importance of women's involvement in AI and technology. The discussion provides valuable insights into these two key areas, shedding light on the evolving landscape of marketing and technology.TakeawaysInfluencer marketing and go-to-market strategyThe role of women in AI and technologyChapters00:00 Influencer Marketing and Go-to-Market Strategy11:38 Would You Write the Check?22:40 The Role of Women in AI and Technology
May 7 · 36m
The conversation delves into the topics of AI and automation resilience, as well as the emergence of tech-enabled services for the aging population. The discussion explores the need for downtime in AI systems and the importance of resilience in the face of automation. It also highlights the significance of tech-enabled services for the aging population, focusing on a specific company that addresses the needs of aging individuals.TakeawaysAI and Automation ResilienceTech-Enabled Services for Aging PopulationChapters00:00 AI and Automation Resilience23:40 Tech-Enabled Services for Aging Population