<![CDATA[The Check Writers Room]]>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exposes the unspoken rules of fundraising, and offers founders actionable guidance grounded in today’s realities—not outdated Silicon Valley playbooks.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.

]]>https://www.checkwritersroom.comRiverside.fm (https://riverside.com)Mon, 02 Nov 2026 17:29:38 GMTWed, 21 Jan 2026 00:19:37 GMT60Sydney, Yasmin and Shalanda<p><b><strong>The Check Writers Room</strong></b> is a groundbreaking podcast where the real power brokers of venture capital talk shop—unfiltered.</p><p><br /></p><p>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 <i><em>actually</em></i> 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.</p><p><br /></p><p>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.</p><p><br /></p><p>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.</p><p><br /></p><p>With biweekly episodes, an interactive “Ask a VC” segment driven by real founder questions, and appearances from trusted peers and ecosystem leaders, <b><strong>The Check Writers Room</strong></b> is more than a podcast—it’s a masterclass and a community for builders serious about building enduring companies.</p>episodicSydney, Yasmin and Shalandasydney@symphonic.vcno<![CDATA[The Room on the Vineyard]]>Welcome everybody to our season finale and thank you all very much for joining us on this ride so far. This conversation with The Melissa Bradley of 1863 Ventures delves into the changing landscape of Martha's Vineyard, the impact of the Black Economic Alliance (BEA), the dynamics of venture capital and philanthropy investing, the psychology of money and exit strategies, the role of AI, technology, and upskilling, and the significance of Black joy and community building. Come sit with us for a while in this place we all love as we round out what has been a great first season with one of the pioneers of Black women venture capitalists.


]]>3e0937a4-bf3f-431f-936f-e5bfbe96baedThu, 03 Sep 2026 11:00:00 GMT<p>Welcome everybody to our season finale and thank you all very much for joining us on this ride so far. This conversation with The Melissa Bradley of 1863 Ventures delves into the changing landscape of Martha's Vineyard, the impact of the Black Economic Alliance (BEA), the dynamics of venture capital and philanthropy investing, the psychology of money and exit strategies, the role of AI, technology, and upskilling, and the significance of Black joy and community building. Come sit with us for a while in this place we all love as we round out what has been a great first season with one of the pioneers of Black women venture capitalists.</p><p><br /></p>no00:39:13119The Room on the Vineyardfull<![CDATA[The Room with the State of the Market]]>Marlon Nichols from Mac Venture Capital joins the podcast to discuss the state of the market in VC and the investment landscape for physical AI and the real economy. The conversation delves into the shift from hardware to software and back to hardware, the challenges and opportunities of hardware coupled with services, the potential of AI in scaling services, the growth of venture dollars into hardware, the impact of government spending and defense on hard tech, the limitations of AI in enterprise, and the changing landscape of venture funding and round sizes.

Takeaways

  • Venture capital is experiencing a liquidity issue, but the market is healthy and will eventually recover.
  • The real economy, particularly the 80% that is not digital, presents opportunities for investment in physical AI and manufacturing companies. Hardware and software cycles: The conversation explores the cyclical nature of the tech industry, shifting from hardware to software and back to hardware.
  • AI and scaling services: The potential of AI in scaling services is discussed, highlighting the opportunities it presents for hardware coupled with services.
  • Venture funding and round sizes: The changing landscape of venture funding and round sizes is examined, with a focus on the impact of multi-billion dollar firms and the need for larger round sizes at the seed stage.
]]>dfefe253-a6ec-4218-af15-540f481f1bccThu, 27 Aug 2026 11:00:00 GMT<p>Marlon Nichols from Mac Venture Capital joins the podcast to discuss the state of the market in VC and the investment landscape for physical AI and the real economy. The conversation delves into the shift from hardware to software and back to hardware, the challenges and opportunities of hardware coupled with services, the potential of AI in scaling services, the growth of venture dollars into hardware, the impact of government spending and defense on hard tech, the limitations of AI in enterprise, and the changing landscape of venture funding and round sizes.</p><p></p><p>Takeaways</p><ul><li>Venture capital is experiencing a liquidity issue, but the market is healthy and will eventually recover.</li><li>The real economy, particularly the 80% that is not digital, presents opportunities for investment in physical AI and manufacturing companies. Hardware and software cycles: The conversation explores the cyclical nature of the tech industry, shifting from hardware to software and back to hardware.</li><li>AI and scaling services: The potential of AI in scaling services is discussed, highlighting the opportunities it presents for hardware coupled with services.</li><li>Venture funding and round sizes: The changing landscape of venture funding and round sizes is examined, with a focus on the impact of multi-billion dollar firms and the need for larger round sizes at the seed stage.</li></ul>no00:57:14118The Room with the State of the Marketfull<![CDATA[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.

]]>620437b2-6996-451d-8509-0324cfb44bd7Thu, 13 Aug 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Healthcare technology startups must understand the distinction between building a standalone product and a feature within a larger conglomerate.</li><li>Deep integration in the workflow and proprietary data are crucial for achieving a billion-dollar valuation in the healthcare technology space.</li><li>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.</li><li>Maintaining momentum, managing relationships, and aligning expectations are key factors in the acquisition process.</li></ul><p></p>no00:39:54117The Room with Standalones, Features, and Strategic Planningfull<![CDATA[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.
]]>38db48ee-db7a-4c09-91d1-121d94b19b9bThu, 06 Aug 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Investor relationships play a crucial role in the startup ecosystem.</li><li>Founder challenges often require a strong support system. Seed funding is shifting away from the traditional Silicon Valley model.</li><li>Building a company with an exit in mind requires careful consideration of valuation and potential acquirers.</li><li>PE-backed acquisitions in healthcare technology often involve different valuation metrics and considerations.</li></ul>no00:28:56116The Room with Premeditated Exits and PE Relationshipsfull<![CDATA[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 athletes
  • The importance of understanding family history and heritage
]]>6641462e-d194-4957-9f5b-7bae2824d252Thu, 23 Jul 2026 11:00:00 GMT<p>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. </p><p></p><p>Takeaways</p><ul><li>Women's health is gaining prominence and importance, driven by millennial attitudes towards healthcare.</li><li>Fraudulent activity in tech startups is a common practice, but founders need to be aware of the risks and consequences.</li><li>Famous parentage can impact a startup's success and public perception.</li><li>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</li><li>The importance of understanding family history and heritage</li></ul>no00:45:02115The Room with Women's Healthcare, Phia Shopping, and NCAA NILfull<![CDATA[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 capital
  • The Midas list and its impact on VC firms Venture Capital and Emerging Managers
  • Building Trust and Relationships in Venture Capital
  • Importance of Diversity and Inclusion in Venture Capital

]]>3354949f-8c54-49e2-9e96-2db1e2cccd45Thu, 16 Jul 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Importance of women in venture capital</li><li>The Midas list and its impact on VC firms Venture Capital and Emerging Managers</li><li>Building Trust and Relationships in Venture Capital</li><li>Importance of Diversity and Inclusion in Venture Capital</li></ul><p></p>no00:41:19114The Room with The Midas List, The State of the Market, and All Raisefull<![CDATA[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 Partners
  • Long-Term Vision for Startups

]]>709fa47d-6858-4543-bec4-ce62c6d4902aFri, 10 Jul 2026 16:11:44 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Corporations as Startup Partners</li><li>Long-Term Vision for Startups<p></p></li></ul>no00:40:22113The Room with Storytelling, Optimization, & Enterprisesfull<![CDATA[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 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

]]>7d5ed498-21bd-48ed-9d93-32e2b7dce382Thu, 25 Jun 2026 11:00:00 GMT<p>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. </p><p></p><p>Takeaways</p><ul><li>Unprecedented IPO valuations</li><li>Impact of DevOps and AI on the software sector The impact of technical debt on enterprise software and the need for sustainable solutions</li><li>The importance of agility, active learning, and trying, failing, and iterating in entrepreneurship</li></ul><p></p>no00:46:03112The Room with IPOs, DevOps, and Foundersfull<![CDATA[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 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
]]>caf963f1-0218-4451-86c6-dd5f31189fa9Thu, 18 Jun 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Venture Capital Challenges</li><li>Adapting to Industry Changes</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction and Background</li><li>06:34 Navigating Downturns</li><li>17:16 Challenges in the Industry</li><li>24:57 Impact of Technology and Innovation</li><li>35:12 Opportunities in Regulatory Technology</li></ul>no00:39:06111The Room with William Crowderfull<![CDATA[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 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
]]>0ee0061d-e2aa-4255-ae27-e13c0168e755Thu, 11 Jun 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Acquisition of Everlane by Shein</li><li>Impact of AI on venture investing</li><li>Challenges of evaluating startups and founders Structuring evaluation of potential can help address human evaluation biases in VC.</li><li>AI may be less biased than humans in evaluating gender and race, but its ability to predict outliers and contrarian thinking is uncertain.</li><li>The systemic aspects of venture capital require a shift in focus from resource seekers to changing the system.</li><li>The use of AI in evaluating potential and the investment process requires careful consideration and a one-step-ahead approach.</li></ul><p></p><p>Chapters</p><ul><li>00:00 Systematic Barriers and Biases in Evaluation</li><li>51:02 The Limitations of AI in Contextual Understanding</li></ul>no00:56:56110The Room with AI and Investor Strategyfull<![CDATA[The Room with Way Up]]>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.

Takeaways

Chapters

  • 00:00 Introduction to Special Episode
  • 01:14 Teaser 1
  • 03:57 Teaser 2
  • 05:44 Teaser 3
  • 07:17 Teaser 4
]]>6ec92818-12ae-40ba-bed0-c529e6adcfebThu, 04 Jun 2026 11:00:00 GMT<p>The episode features all three hosts in person and can be accessed by<a rel="noopener noreferrer nofollow" href="https://youtu.be/5lhPEMH3-qs?si=O3871cPaYFcSdfKn" target="_blank"> clicking the link here</a>. 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.</p><p></p><p>Takeaways</p><ul><li>Podcast episode features all three hosts in person</li><li>Access the episode <a rel="noopener noreferrer nofollow" href="https://youtu.be/5lhPEMH3-qs?si=O3871cPaYFcSdfKn" target="_blank">by clicking here</a>. </li><li>Sharable episode link: <a rel="noopener noreferrer nofollow" href="https://youtu.be/5lhPEMH3-qs?si=O3871cPaYFcSdfKn" target="_blank">https://youtu.be/5lhPEMH3-qs?si=O3871cPaYFcSdfKn</a></li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Special Episode</li><li>01:14 Teaser 1</li><li>03:57 Teaser 2</li><li>05:44 Teaser 3</li><li>07:17 Teaser 4</li></ul>no00:09:5819The Room with Way Upbonus<![CDATA[The Room with Continuation Vehicles and Echocardiograms]]>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.

Takeaways

  • Venture Capital and Fund Management
  • Healthcare Technology and AI
  • Investment Strategy and Fund Lifecycle

Chapters

  • 0:00 Fund Management and Continuation Vehicles
  • 12:55 Would You Write the Check?: iCardio
  • 27:34 Personal Joy and Inspiration
]]>82c86e0c-0bd6-4ea6-9bb9-73970fa4f353Thu, 21 May 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Venture Capital and Fund Management</li><li>Healthcare Technology and AI</li><li>Investment Strategy and Fund Lifecycle</li></ul><p></p><p>Chapters</p><ul><li>0:00 Fund Management and Continuation Vehicles</li><li>12:55 Would You Write the Check?: iCardio</li><li>27:34 Personal Joy and Inspiration</li></ul>no00:32:5318The Room with Continuation Vehicles and Echocardiogramsfull<![CDATA[The Room with Takedowns, Stealth Mode, & Women in AI]]>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.

Takeaways

  • Influencer marketing and go-to-market strategy
  • The role of women in AI and technology

Chapters

  • 00:00 Influencer Marketing and Go-to-Market Strategy
  • 11:38 Would You Write the Check?
  • 22:40 The Role of Women in AI and Technology
]]>a295e854-8878-4de9-a425-dae3f7babd98Thu, 14 May 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Influencer marketing and go-to-market strategy</li><li>The role of women in AI and technology</li></ul><p></p><p>Chapters</p><ul><li>00:00 Influencer Marketing and Go-to-Market Strategy</li><li>11:38 Would You Write the Check?</li><li>22:40 The Role of Women in AI and Technology</li></ul>no00:35:3817The Room with Takedowns, Stealth Mode, & Women in AIfull<![CDATA[The Room with Automation Resilience & Tech-Enabled Services]]>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.

Takeaways

  • AI and Automation Resilience
  • Tech-Enabled Services for Aging Population

Chapters

  • 00:00 AI and Automation Resilience
  • 23:40 Tech-Enabled Services for Aging Population
]]>aba377d1-c5f8-404d-b9a8-8eb17152f312Thu, 07 May 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>AI and Automation Resilience</li><li>Tech-Enabled Services for Aging Population</li></ul><p></p><p>Chapters</p><ul><li>00:00 AI and Automation Resilience</li><li>23:40 Tech-Enabled Services for Aging Population</li></ul>no00:36:0616The Room with Automation Resilience & Tech-Enabled Servicesfull<![CDATA[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.

Takeaways

  • Introspection and accountability in investing
  • Challenges and considerations in consumer deals
  • Real estate as an alternative asset class

Correction

  • Harry'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.

Chapters

  • 00:00 Introspection and Accountability in Investing
  • 09:30 Consumer-Deals
  • 14:34 Real Estate as an Alternative Asset Class
]]>deefd2d5-f8d7-486e-9047-2d45b08f4e30Thu, 30 Apr 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Introspection and accountability in investing</li><li>Challenges and considerations in consumer deals</li><li>Real estate as an alternative asset class</li></ul><p></p><p>Correction</p><ul><li>Harry'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.</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introspection and Accountability in Investing</li><li>09:30 Consumer-Deals</li><li>14:34 Real Estate as an Alternative Asset Class</li></ul>no00:34:5115The Room with Introspection, Consumer Deals & Real Estatefull<![CDATA[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.

Takeaways

  • Challenges in 12 to 18-month fund cycles
  • Impact on founders and investor circles

Chapters

  • 00:00 The Hot Take: 12 to 18 Month Fund Cycles
  • 05:57 The Importance of Building a Brand
  • 11:17 Scrutiny on Pre-Seed, Seed, and Series A
  • 17:23 The Uncertainty in the Software Sector
  • 23:17 Transitioning to AI Tools and Friction
  • 33:14 Investment Strategy in Uncertain Times
  • 41:14 Finding Joy in Uncertain Times
]]>4c895ebd-32c0-455c-865b-80c61867bdb4Thu, 23 Apr 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Challenges in 12 to 18-month fund cycles</li><li>Impact on founders and investor circles</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Hot Take: 12 to 18 Month Fund Cycles</li><li>05:57 The Importance of Building a Brand</li><li>11:17 Scrutiny on Pre-Seed, Seed, and Series A</li><li>17:23 The Uncertainty in the Software Sector</li><li>23:17 Transitioning to AI Tools and Friction</li><li>33:14 Investment Strategy in Uncertain Times</li><li>41:14 Finding Joy in Uncertain Times</li></ul>no00:36:3314The Room with Fund Cycles & the Future of SaaSfull<![CDATA[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.

Takeaways

  • Investment 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.

Chapters

  • 00:00 Investment in Women's Sports
  • 07:37 Challenges in Broadcasting Women's Sports
  • 16:05 Robin Hood Ventures and Democratization of Venture
  • 35:23 Investment in Deep Tech: Sumeria Space
]]>2b482d6a-e8c1-4bf0-b9c6-6ddbc3b2a60aThu, 16 Apr 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Investment in women's sports requires consideration of economic levers and revenue potential.</li><li>Broadcasting women's sports faces challenges related to exposure, market capitalization, and revenue potential.</li><li>Robin Hood Ventures and the democratization of venture involve valuation, liquidity, and tax implications.</li><li>Investment in deep tech, such as Sumeria Space, requires market sizing, regulatory and policy considerations, and an exit strategy.</li></ul><p></p><p>Chapters</p><ul><li>00:00 Investment in Women's Sports</li><li>07:37 Challenges in Broadcasting Women's Sports</li><li>16:05 Robin Hood Ventures and Democratization of Venture</li><li>35:23 Investment in Deep Tech: Sumeria Space</li></ul>no00:38:5713The Room with Moonshot Moves in Sports, Space & Retail Investingfull<![CDATA[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.

Takeaways

  • Paternity Leave
  • Maternal Health
  • AI in Healthcare

Chapters

  • 00:00 Introduction to Jewel Burke Solomon
  • 09:13 Importance of Paternity Leave
  • 14:28 AI in Healthcare
  • 19:31 Interoperability of Medical Records
  • 26:18 Investment in Maternal Health Company
  • 32:56 Impact of Medicaid on Investment
  • 39:18 Investment Climate and Opportunities
]]>a4401b8a-8511-4b40-a6ec-3f33cdf067d1Thu, 09 Apr 2026 11:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Paternity Leave</li><li>Maternal Health</li><li>AI in Healthcare</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Jewel Burke Solomon</li><li>09:13 Importance of Paternity Leave</li><li>14:28 AI in Healthcare</li><li>19:31 Interoperability of Medical Records</li><li>26:18 Investment in Maternal Health Company</li><li>32:56 Impact of Medicaid on Investment</li><li>39:18 Investment Climate and Opportunities</li></ul>no00:35:5711The Room With Paternity Leave & Maternal Health Investmentsfull<![CDATA[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.

Takeaways

  • Bridge rounds as a trend
  • Impact of layoffs in tech

]]>74aac0a1-5c81-4e53-8a02-c123b647bce9Wed, 01 Apr 2026 21:15:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Bridge rounds as a trend</li><li>Impact of layoffs in tech</li></ul><p></p>no00:38:0211The Room With Bridge Rounds & Layoffsfull<![CDATA[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.

Takeaways

  • New voice in VC
  • Rapid industry transformation

Chapters

  • 00:00 Introduction to CheckWriter's Room
]]>32bafd53-dec0-453d-b150-31c58a1374b8Wed, 01 Apr 2026 13:53:46 GMT<p>The Check Writer's Room introduces a new voice in the VC industry, offering unique perspectives on the rapidly changing landscape.</p><p></p><p>Takeaways</p><ul><li>New voice in VC</li><li>Rapid industry transformation</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to CheckWriter's Room</li></ul>no00:00:27Welcome to the Check Writers Room!full