PODCAST · business
The Check Writers Room
by Sydney, Yasmin and Shalanda
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exposes the unspoken rules of fundraising, and offers founders actionable guidance grounded in today’s realities—not outdated Silicon Valley playbooks.
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8
The Room with Introspection, Consumer Deals & Real Estate
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 classChapters00:00 Introspection and Accountability in Investing14:34 Real Estate as an Alternative Asset Class
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The Room with Fund Cycles & the Future of SaaS
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
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The Room with Moonshot Moves in Sports, Space & Retail Investing
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
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5
The Room With Paternity Leave & Maternal Health Investments
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
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The Room With Bridge Rounds & Layoffs
The podcast episode features a discussion on bridge rounds and their impact, a review of a specific deal (Wiggle Room), and an exploration of the impact of layoffs in the tech industry. The hosts introduce their mission and purpose at the beginning of the episode, setting the stage for the subsequent discussions.TakeawaysBridge rounds as a trendImpact of layoffs in tech
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Welcome to the Check Writers Room!
The Check Writer's Room introduces a new voice in the VC industry, offering unique perspectives on the rapidly changing landscape.TakeawaysNew voice in VCRapid industry transformationChapters00:00 Introduction to CheckWriter's Room
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ABOUT THIS SHOW
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.
HOSTED BY
Sydney, Yasmin and Shalanda
CATEGORIES
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