• 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
    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
    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
  • The Room with Way Up
    Jun 4 2026

    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

    • Podcast episode features all three hosts in person
    • Access the episode by clicking here.
    • Sharable episode link: https://youtu.be/5lhPEMH3-qs?si=O3871cPaYFcSdfKn

    Chapters

    • 00:00 Introduction to Special Episode
    • 01:14 Teaser 1
    • 03:57 Teaser 2
    • 05:44 Teaser 3
    • 07:17 Teaser 4
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    10 mins
  • The Room with Continuation Vehicles and Echocardiograms
    May 21 2026

    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
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    33 mins
  • The Room with Takedowns, Stealth Mode, & Women in AI
    May 14 2026

    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
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    36 mins
  • The Room with Automation Resilience & Tech-Enabled Services
    May 7 2026

    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
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    36 mins
  • The Room with Introspection, Consumer Deals & Real Estate
    Apr 30 2026

    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
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    35 mins