The Check Writers Room
Sydney, Yasmin and Shalanda·12 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exposes the unspoken rules of fundraising, and offers founders actionable guidance grounded in today’s realities—not outdated Silicon Valley playbooks.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
June 18, 2026 · 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. 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
More Episodes
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
Apr 30 · 34m
The conversation delves into introspection and accountability in investing, highlighting the challenges and considerations in consumer deals, and discussing real estate as an alternative asset class. The speakers explore the impact of Mark Andreessen's perspective on introspection, mental models in evaluating consumer deals, and the dynamics of the rental market. They also touch on the significance of real estate as an alternative asset and the implications for investors.TakeawaysIntrospection and accountability in investingChallenges and considerations in consumer dealsReal estate as an alternative asset classCorrectionHarry's didn't sell to Unilever for $1B - Edgewell offered $1.37B in 2019, the FTC blocked the merger in 2020, and Harry's stayed independent. They've since become a CPG platform that's now acquiring other brands.Chapters00:00 Introspection and Accountability in Investing09:30 Consumer-Deals14:34 Real Estate as an Alternative Asset Class
Apr 23 · 36m
The conversation delves into the challenges and shifts in the tech and venture capital landscape, focusing on fund cycles, founder access to capital, the impact on software sectors, and the uncertainty in vertical SaaS companies. The discussion also explores the importance of building a brand, the scrutiny on enterprise revenue, and the investment strategy in uncertain times.TakeawaysChallenges in 12 to 18-month fund cyclesImpact on founders and investor circlesChapters00:00 The Hot Take: 12 to 18 Month Fund Cycles05:57 The Importance of Building a Brand11:17 Scrutiny on Pre-Seed, Seed, and Series A17:23 The Uncertainty in the Software Sector23:17 Transitioning to AI Tools and Friction33:14 Investment Strategy in Uncertain Times41:14 Finding Joy in Uncertain Times
Apr 16 · 38m
The conversation covers a range of topics, including investment in women's sports, challenges in broadcasting women's sports, Robin Hood Ventures and the democratization of venture, and investment in deep tech with a focus on Sumeria Space. The discussion delves into economic levers, opportunities for female athletes, profitability, revenue potential, lack of exposure, market capitalization, valuation, liquidity, tax implications, market sizing, business model, regulatory and policy considerations, and exit strategy.TakeawaysInvestment in women's sports requires consideration of economic levers and revenue potential.Broadcasting women's sports faces challenges related to exposure, market capitalization, and revenue potential.Robin Hood Ventures and the democratization of venture involve valuation, liquidity, and tax implications.Investment in deep tech, such as Sumeria Space, requires market sizing, regulatory and policy considerations, and an exit strategy.Chapters00:00 Investment in Women's Sports07:37 Challenges in Broadcasting Women's Sports16:05 Robin Hood Ventures and Democratization of Venture35:23 Investment in Deep Tech: Sumeria Space
Apr 9 · 35m
The conversation covers a range of topics including the importance of paternity leave, AI in healthcare, investment in maternal health, and personal reflections on joy. The discussion delves into the impact of paternity leave on workplace productivity, long-term career potential, and earnings. It also explores the challenges and opportunities in AI healthcare, the significance of value-based care contracts, and the impact of legislation on healthcare. Additionally, the conversation touches on the readiness of a maternal health company for Series A investment and the investment climate and opportunities in the industry. Personal reflections on joy and the impact of personal experiences on investment decisions are also discussed.TakeawaysPaternity LeaveMaternal HealthAI in HealthcareChapters00:00 Introduction to Jewel Burke Solomon09:13 Importance of Paternity Leave14:28 AI in Healthcare19:31 Interoperability of Medical Records26:18 Investment in Maternal Health Company32:56 Impact of Medicaid on Investment39:18 Investment Climate and Opportunities